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Good afternoon. We're going to get started. Alright. We are going to finish chapter 11 today and start chapter 12. So hopefully everybody has started cataloging their reactions. There's a lot of new reactions in chapter 12. There's a lot of reactions in chapter 12 that you will use a lot the rest of the year of OCCEM. So I also just looked on our website and there's an addition summary sheet that summarizes everything we covered in chapter 10. I looked and it's not there. So I'm going to put that up and you can take a look. Highly recommend you take a look at that handout. Alright. So we left off last time talking about the mechanism that this was guaranteed to be on the midterm, correct? Yes. It should be. When did you look? Somebody else accessed it? Yes? Yes. So try now. Should be it. Okay. Alright. So we said this mechanism is guaranteed to be on the midterm. So let's add some things here. Alright. When we first made our carbocation here, we put the positive charge on the most substituted side. Of course, that one doesn't have a most substituted side, but if it was a terminal alkyne, you would put it at the most substituted side. This is a Markovnikov addition. And then there's a couple, there's some, a little bit of terminology that we're going to be adding here. This is this type of structure where you have a vinyl alcohol, has a special name. It's called an enol. So when you name alcohols, you use an all ending. And when you name alkenes, you use an ene ending. So that's where we get that name from. It's an enol. And generally speaking, 99% of the time, these structures are not favored at equilibrium. So enols are generally unstable. They are, you form them in reactions, but then they're converted into their more stable form. So the more stable form would be this form right here, which is we call the keto form. So we call this one an enol, or we can call it the enol form. And this is the keto form. And when we have an enol form equilibrating, so notice the equilibrium arrows here. When we have an enol and a keto form equilibrating, we call that a tautomerization. So these two structures, the enol and the keto, I made the arrow the wrong direction there. Let's fix that. They interconvert. So long arrow to the keto form, very short arrow to the vinyl form. And the vinyl, so this is called a tautomerization. And the enol form and the keto form are tautomers. So basically as soon as we form this enol form, then it's going to automatically tautomerize that equilibrium to a ketone. So not favored at equilibrium. So therefore it will tautomerize to a ketone. So this whole process here, let me circle everything that's the tautomerization. Going this whole part right here is how you tautomerize. So going between these species, that's the tautomerization. So you want to make sure on the exam that you actually show that exactly how I've shown it here. So to go from, because some students will just draw the vinyl alcohol and then they'll just draw arrows and they'll draw the keto form, but then you're going to miss all the points here. So let's add up how many points this problem is going to be on midterm two. It's the way that I do my mechanisms is this usually two points per step. So we have, let's count it up. Two, four, six, eight. I want to see both of these resonance structures. So two, four, six, eight, ten, twelve. And then I want you to label the enol form and I want you to label the keto form. So that's 14 points on midterm two. So that's the lowest score that's going to be on midterm two, right? Because that's all you have to, if you want 14 points, that's all you have to study. So that's what I was talking about. That will be my lowest score and I say I wish that would be my lowest score. Okay, so the way that we do mechanisms is if you're missing arrows, like say you just do this first arrow and you don't do the second arrow, you don't get points for that step. You have to have all the arrows. If you're missing lone pairs and charges, you miss points and I believe me the points add up. So make sure you take a look at your test and see what you did wrong on your test with the mechanisms on the test. Alright, so you'll get partial credit if you don't have charges. If you're missing arrows, you won't get points for, you'll miss partial credit. If you combine steps, more than one step, then you miss the points for each step. So if you combine two steps into one, then you miss four points. So that just kind of gives you an idea on how that's graded. Questions on this mechanism, anybody? Anyone? Yes? Oh, very, thank you for pointing it out. So when I grade a mechanism, I don't care if you do these reversible arrows, I'm only focused on curvy arrows. That's it. So don't worry yourself about, oh, if I don't do reversible arrows, I don't care about that. I just care about the curvy arrows. Alright, point and points about this reaction. And this is going to come back in 51C. So this terminology, tautomers, enol form, keto form, that's coming back in 51C, big time. So carbonyl compounds with alpha hydrogens, well we don't know what alpha hydrogens are, but they're hydrogens that are adjacent to the carbonyl. So this carbonyl right here has six alpha hydrogens. Carbonic compounds with alpha hydrogens are in equilibrium with vinylic alcohol, isomers called enols, the two isomers that interconvert are called tautomers. So this one would be the keto form, and this is the enol form. And most of the time, we're going to say 99% of the time the keto form is more stable, so that's what you're going to actually isolate from the equilibrium. For this particular one, we have keq equals 7 times 10 to the minus 6. So that certainly tells you that the keto form is more favored. And that's the case. When you get into 51C, it'll show you a couple of exceptions to this rule, that the keto form is more favored. There's a few of them, a few important ones, but nothing we have to worry about now. So the keto form, usually favored. At equilibrium. So when you're doing predicting products on midterm 2, if you draw an enol, it's going to be the wrong answer. Okay, so we're not going to be isolating enols, because they're not stable. And so tautomerization, like we said, conversion of an enol to a ketone by protonation of the carbon of the double bond and deprotonation of the oxygen atom. This tautomerization can happen in acid or base. You do need a little bit of a catalyst here. So the one that we, the mechanism we saw on the previous page was acid catalyzed tautomerization. On the next page, we're going to see base catalyzed tautomerization. So there's two of them. And you're going to need to know both of them in 51C, certainly. Alright, so when an enol is formed in reaction, it will automatically convert to its keto form. The presence of tracerb acids are based, so don't draw an enol as a product. Because it's not. Don't draw an enol as a product. Alright, so the addition of water to all kinds follows Markovnikov's rules. So the hydrogen adds to the carbon with the most number of hydrogens. And that's certainly to give the more stable carbocation. Terminal alkynes are less reactive and require use of an additional catalyst, HgSO4. Okay, so this is an additional catalyst with terminal alkynes. You will want to include that if you're doing a synthesis problem like this. Additional catalyst needed. Now there's a mechanism that goes along with that additional catalyst. I'm not going to show you that. You are not required to know that. So when I put this question on midterm 2, it will not be a terminal alkyn. It will be an internal alkyn. Okay? Don't need to know that other mechanism. Products always a ketone except when acetylene is hydrated. So the only way that you can get an aldehyde with hydration is if you use acetylene. That's it. On symmetrical internal alkynes, we'll give a mixture of products. There's nothing you can do about it. So this will give two products. So if you were, if you wanted to make one of these two products, you would probably do it a different way because these two products would be really difficult to separate from each other. So that's something you have to keep in mind. Questions on hydration of an alkyne? Anybody? Let's talk about addition of bromine and chlorine. As you can see, I'm not going to spend too long on this. One equivalent of halogen gives you transdi-bromoalkene. If you do two equivalents of halogen, you can get tetra-bromoalkene. Rather than draw the products, let's just go through the mechanism here. I'm going to start with my alkyne here. If you know the mechanism for bromination in chapter 10, this will be a very easy mechanism for you. Okay, so the arrow comes from the pi bond. We attack bromine. We break the bromine-bromine bond and one of the lone pairs on bromine comes and attacks the other side. So we make a bromine. This would be, this one's not a bromonium. It's a bromenium ion. So like a bromonium ion, except we have a double bond in our molecule. Same idea though. We have a bromide ion come in, backside attack. This is symmetrical, so it can attack on either side. I'll just attack right here. So there's our transdi-bromoalkene with one equivalent. And then if we add another equivalent of bromine, and you can do that mechanism, that's a chapter 10 mechanism. It will look just exactly like the mechanism for chapter 10. We're going to make a bromonium ion and then we're going to do backside attack. And I'm not going to attempt to show any stereochemistry here, because there is no stereochemistry here. We don't have any stereocenters. Because we're adding two bromines to each carbon, there are no stereocenters. So the product after one equivalent is this. The product after two equivalents is this. Really straightforward. Students tend to do really well on alkenes. Any time I test on alkenes, students tend to do really well, because they're not super difficult. All right, we're going to end with hydroboration and oxidation of alkynes. Like alkenes, alkynes undergo hydroboration, which we did with borane reagents. It's going to be the same idea. Yes. Yeah. Yes, let's change that to an A. Thank you. We'll fix that right now. Thank you for pointing that out. Tetobromoalkane, yes. All right. So the same concepts that we learned for hydroboration in Chapter 10 are going to also apply here. There's three different borane reagents that you will see in this chapter. BH3THF or 9BBN, which I introduced to you in Chapter 10. 9BBN. Or there's another reagent that tends to work really well with alkynes, and that's called disyamylboring, which is similar to 9BBN in that it's more bulky than a typical, it's more bulky than BH3, certainly. So you tend to get better results. So this one here is called disyamylboring. Sin addition, right? Just like in Chapter 10. So there's our reagent there, and so that you notice is that the boron and the hydrogen both came in on the same side. So this is a sin addition. Unsymmetrical alkynes give mixtures better to use 9BBN here, definitely. 9BBN is much better when you have subtle differences in the groups on either side of the alkyne. So here we have the hydrogen. You'd get both of these if you use BH3. If you use 9BBN or disyamylboring, you get your major one is the second one. So major if 9BBN or disyamylboring. Terminal alkynes also undergo hydroboration. BH3 THF does not work very well for terminal alkynes. I'm choosing not to make an issue about it. But really for terminal alkynes, you need to use disyamylboring or 9BBN. So let's cross that out. 9BBN, you still will see answers. You will still see problems on Smith, and you will still see problems in Sapling where they use 9BBN or BH3. The problem with BH3 is that it tends to add twice, and then that causes all sorts of problems in the product that you actually isolate. So I've drawn the product that you get from hydroboration. We're usually not super interested in those products in this class anyway. So what we normally do is we oxidize these, right? Basic hydrogen peroxide. So let's see what happens when we oxidize these on the next page. Now when we oxidize our hydroboration product, we put an hydrogen hydroxyl right where the boron was, right? Same thing here. Let's draw that. And now we draw that, we look at that product. What type of product is that? It's an enol. Do we want to draw enols in any answers on our test? No. So yes, we do form an enol, and I want you to be able to recognize, wow, that's an enol, I shouldn't draw that. So what this is going to do is it's going to tautomerize. So long arrow to the right, short arrow to the left. And when you tautomerize this, where the hydroxyl is, is going to become a carbonyl. So this is, so that's what you get for the first example, and then we're going to actually show the mechanism here, because it's different than the acid catalyzed. So that's also an enol. And again, exactly where the hydroxyl is, the double bond goes away, and the hydroxyl is going to become a carbonyl. So for both of these, this is base catalyzed tautomerization. So what you want to draw in the box is the carbonyl product. Let's see what that mechanism looks like. So I've already showed you acid catalyzed, that's the one that's guaranteed to be on the midterm. Let's look at what the base catalyzed looks like. I'm going to start with this enol right here. And what I'm going to do first is deprotonate oxygen. So I am doing something very different in base than I did in acid. In the acid catalyzed tautomerization, we hydrated the double bond. We added, we protonated the double bond. Here we're deprotonating oxygen. Notice I'm doing reversible arrows here, because this is a reversible reaction. And I drew resonance structures in the acid catalyzed tautomerization, and I'm going to do the same thing here in the base catalyzed tautomerization. So I know that this is resonance stabilized. I can move these electrons here. This goes all the way back to chapter one. So now instead of arrows that go both directions, I'm going to use a resonance arrow. So that's how you get that double bond there. So now we have negative charge on carbon. And now you can see to get to that product we have here, all we need to do is protonate that carbon. So base catalyzed, we're going to protonate that carbon with water. That regenerates the base that we started with. So this really is only catalytic. So let's put brackets around these two resonance structures here. So exact same outcome, just a little bit different mechanism because it's acid catalyzed versus base catalyzed. And I know some of you had trouble with that when we did epoxides. But acid catalyzed and base catalyzed mechanisms are extremely important in 51C. So that's why I'm emphasizing them now. It'll make it much easier for your next quarter. So stepwise mechanisms, you don't want to combine steps. We talked about that. So don't do this. Let me show you what you don't want to do for this mechanism. So I'll draw it and then you're going to tell me what's wrong with it. And just in case you don't read the don't do this when you're studying, we'll put a big X through this mechanism after we draw it. So there's our enol. We want to tautomerize. So basically I'm just going to kind of do the same thing. Only I'm going to do it all in one step. Combine steps here. So I'm going to grab this here. I'm going to have these electrons come over here. And then I'm going to have the double, the pi bond come and grab a hydrogen from water. That would do my thing all in one step. Why is that bad? What am I doing wrong? Why would that be a very unlikely process here? There's three species all coming together simultaneously with the right orientation, exact orientation, all of them colliding with enough energy to react. It's such a rare event that we don't want to presume that that's happening. So no, we call these termolecular reactions. No termolecular reactions. And so when you combine steps on a mechanism, you generally speaking are doing termolecular reactions. You're having too many things happen at the same time. So that means three molecules coming together simultaneously. Alright, so don't want to do that, don't want to suggest that. Alright, so compare the result of T when a termoleucine undergoes acid, catalyzed hydration versus hydroboration. Well, one's anti-Marconikov and the other one's Marconikov. So remember, where the oxygen goes, that's where the carbonyl is going to be. So hydroboration gives you anti-Marconikov and then hydration gives you a Marconikov. So it's really nice that we have these complementary procedures. So sometimes we want one of these and sometimes we want the other and we have, so now we have two ways to do this at our fingertips that we can use for synthesis. Alright, questions, anybody so far? We're going to start at this point getting into more complicated synthesis. I'm going to give you one example here and then by the time we get to the end of chapter 12, you're going to have much more complicated synthesis. So this is the time to get in gear and start practicing a lot of synthesis. So this is the time when you'll see at the end of the chapter, once you do all the predicting the products, there's a synthesis part where we have reactions from multiple chapters. That's what you want to spend your time on and you want to try to solve those without looking at the answers. So in planning a synthesis, depending on what we're trying to plan, we might need to construct the carbon skeleton. That's what we're going to have to do in this example of functional group interconversion. We're doing that in this example. We're taking an alkyne and converting it into a ketone. So that's functional group interconversion. We are going to have to control regiochemistry. So here's a really good example here, this previous example here. We were controlling regiochemistry by choosing the correct reagent. And then some of the examples we're going to have to control stereochemistry, those are going to be coming up at the end of chapter 12. So we've got to think about all of these things. This particular one, we don't have any stereochemistry, so we don't really have to control this. Can stereochemistry, prepare the following compound from acetylene. So it looks enormously complicated. Using our retrosynthetic arrow is going to really help us. So this is acetylene. And I'm not going to bother going in the forward direction. I can see it in the forward direction, and maybe you can too. And certainly do it that way, but I'm just going to work backwards from the product. So I'm going to use my retrosynthetic arrow that can be made from. And I'm going to work backwards. So again, let's label that. Retrosynthetic arrow means this can be made from. And this is where the recognizing those functional groups, we've really only talked about two ways to make a carbonyl so far. So that makes this a little easier. By the time you get to 51C, there'll be 10 ways to make a carbonyl. And then it's a little more complicated because so now we're a little limited, and this is the time to jump in and get lots of good practice here. So this one can be made from, well, if I had, I only know one way to make a carbonyl right now, and that's from an alkyne. So I would have to do it from, if I had this alkyne, a terminal alkyne, this would be H2O. I want the carbonyl on the most substituted side here, so I would have to use hydration. H2O, H2SO4, and because it's terminal, I need to add HGSO4 as a catalyst. All right, so I need two carbon pieces, so I'm going to have to take this down further. So I know I can make this from, gosh, if I had this right here, bromide, I could have chloride, iodide, or tosate, and if I had this, I could do a substitution reaction. That's chapter 7. Just do an SN2 reaction. And then now, and I'm always going back and looking at what I started with, and I certainly can make this from acetylene by deprotonating it, right? What base would I use for that? NH or NH2? Or you can write, I don't care, H minus or NH2 minus. So I'm not particular about you concluding the counter ion. If you write that in a synthesis, that's totally fine with me. Okay, so we've got our plan. Now let's write out the synthesis in the forward direction. So when I grade tests, this would be the kind that's the open-ended kind, and I don't grade retrosynthetic, and it's too hard to grade. I can't see the way people are thinking. So I only grade the synthesis in the forward direction. So if it was an open-ended, what I call open-ended synthesis, where I ask for products from each step, it would look something like this. Definitely want to number those two steps. I'm deprotonating, and then I'm adding propyl bromide. And then in my last step here, it would be H2O, H2SO4, HGSO4. So this is three steps, this is three steps in synthesis. Or on a test, it might look like this. If it's not an open-ended, if it's one where you just fill in reagents, I do have more of that type on the test just because these other kind are much harder to grade, you got to worry about these things when you have a lot of students. Alright, so then I might have it like this. And so that would be, then you would do the reagents and you would number the individual steps. Step one, NH. I'll just use NH. Step two, propyl bromide. Step three, H2O, H2SO4. HGSO4. And that should be H2O, not H2. What would happen if I didn't number that? What would happen if I mixed sodium hydride, propyl bromide, H2O, H2SO4, and HGSO4? A very potentially explosive reaction between the sodium hydride and the sulfuric acid. Or sodium hydride in water. It's an extremely strong base. And what happens when you mix an extremely strong base with an extremely strong acid and you don't cool it, you just throw them together, it explodes. It might not blow out a wall, but it will blow compound all over you, that you don't want all over you. So that's why it's really critical that we number the steps as we're doing them, when they need to be numbered. That is chapter 11. We're going to start chapter 12 now. Any questions while I'm pulling up chapter 12? It takes a little while to save this, so what can I, anybody have questions? Alright, chapter 12. Pretty excited about this. Now, here's the thing I don't like about chapter 12. There's no mechanisms in chapter 12. I like mechanisms, right? It also helps you learn what the reaction is actually doing. So this is as close as you're going to come in organic chemistry to a chapter which is all memorization. I know a lot of people think O-chem is all memorization, but really it's some memorization and this is all memorization. I will show you approximately what's happening in a couple of different things, but I will not ask you any mechanisms in chapter 12. And the reason is the mechanisms are a lot more complicated, more complicated than we're ready for. Okay, so that's where we're coming from. So we're going to talk about oxidation and reduction. So first of all, recognizing oxidation and reduction in organic compounds. And I think this was in like chapter 4 or 5 or 6 or something like that. It was covered then. I'm going to assume you don't remember it, so I'm going to cover it again. But you will see the exact notes in one of those chapters if you look back in 51A. Alright, so it's a little bit different in organic chemistry than general chemistry to recognize oxidation and reduction. Here's the good news. Does everybody remember balancing redox reactions? We don't do that here at all. Okay, so that's brutal. I know. So let me give you a G-chem example. We also aren't going to be assigning oxidation, we're not assigning oxidation numbers at all. We don't do that. You can. We had a textbook one time that did that, but none of the other ones have. And so we just, you don't need it. So we're not going to cover it. So copper, shiny, red, metal reacting with silver plus. The copper loses two electrons, right? So this loses two electrons. And transfers those electrons over to silver. The electrons are transferred completely from one species to the other. So then we get the blue copper two plus salts. So pretty cool color changes. I like these things. But this is going to be gaining. This gains electrons. Okay, so we know also that if one molecule is oxidized and another is reduced, that's from G-chem. We're going to carry that forward. And the electrons are transferred completely from one molecule to another. That's what happens. Not like that in organic chemistry. So in organic chemistry, we're not actually transferring electrons completely. We're changing the direction of the flow of electrons. So oxidation is loss of electron density. Carbon loses electrons by forming bonds with elements that are more electronegative than it is. So what we're going to see for oxidation is loss of a carbon hydrogen and gain of a carbon oxygen. These both have to happen at the same time. Both have to happen for oxidation. That's what we're going to look for. Loss of carbon hydrogen, gain of carbon oxygen. So what are we talking about with electron density? Well, electronegativity carbon is 2.5. Hydrogen 2.2. Carbon is 2.5. And rather than use oxygen there, I'm going to do a generic here. Let's just do X. That's a little better. Carbon X. So 2.5 for carbon X. Greater than 2.5. So what we're doing here is we're shifting electron density. With a carbon hydrogen bond, the electron density is flowing towards the carbon because it's more electronegative. When we replace that hydrogen with an X, it's flowing towards X. So we've changed the direction of the flow of electrons. So for here, X equals oxygen, nitrogen, halogen typically. These are the ones that we're going to see. That means you have an oxidation. And it's important to be able to recognize if you have an oxidation or reduction because if you have an oxidation, then you'll know you have to use an oxidizing agent. If you have a reduction, you'll know you have to use a reducing agent. That helps you to figure out what the rubber agent to use. Reduction is the opposite. Loss of CX, gain of CH. So as you can see here, we have electrons flowing to X now and we're changing it so the electrons are flowing to carbon. And again, here X equals oxygen, nitrogen, halogen. I'll just say it's satyr. Because it could be anything. More electronegative. So the following shows stepwise oxidation of methane. Most reduced form of carbon, all the way up to carbon dioxide, which is the most oxidized form of carbon. So you can see what's happening here. As we go from methane to methyl alcohol or methanol, we've lost a carbon hydrogen and we've gained a carbon oxygen. So both things have to take place. So therefore it's an oxidation. Moving to the right, it's an oxidation. And then we have, we do that one more time. We break another carbon hydrogen minus carbon hydrogen plus carbon oxygen. We've gained a second carbon oxygen bond because now we have a double bond of carbon. So that's also an oxidation. And then same thing here, we lose another carbon hydrogen and gain carbon oxygen because now we have three bonds. Carbon's bonded to three oxygens. So minus carbon hydrogen and plus carbon oxygen. And then we're also, we're losing another carbon hydrogen, gaining a carbon oxygen. So that's oxidation. Stepwise oxidation. So four steps to go from the most reduced form of carbon to the most oxidized form. If we went back the other way, I'm not going to draw that here, but it's the exact opposite. If we go from here backwards over to here, we're losing a carbon oxygen and gaining a carbon hydrogen. So that's reduction. Let's just do one of those. I'm not going to do all of them. We can go the opposite direction and step back, going from here to here. We minus carbon oxygen plus carbon hydrogen. Therefore, reduction. All right. So very helpful to be able to recognize. So can you recognize oxidation reduction in the following examples here? So what's happening here? We have two hydrogens and we're replacing those with two carbon oxygens, right? So loss of two carbon hydrogens, gain of two carbon oxygens. Or oxidation. Definitely oxidation there. Let's look at the second example here. We're losing two oxygens, two carbon oxygens, and we're gaining two carbon hydrogens. Therefore, it's a reduction. So if you want to do this reaction, you're going to need to use a reducing agent. In the first one, you're going to need an oxidizing agent to do that reaction. So let's look at one here that's one we've already looked at. Is this an oxidation reduction reaction? Well, that's something, it's not in this chapter, so it's not. It's something that we've already talked about. It's an addition reaction, right? So we know that by looking at that, that's addition. That's an addition reaction. We know that's from chapter 10. And so let's look at what's happened here. We gain one carbon oxygen and we gain one carbon hydrogen. You have to gain one and lose the other. So it's not. It's neither an oxidation nor a reduction. It's an addition. Questions on recognizing oxidation or reduction? Ready? So want to know how to do that for midterm two. We're going to do reduction first and then we're going to do oxidation. You're going to get a slew of reactions and you're going to go home and make index cards for them, okay? There's three types of reducing agents. There's the first type where we add H2 plus a catalyst. That's called a catalytic hydrogenation. And you will generally see, so it will be H2 plus palladium, platinum or nickel. Those would be the common catalysts that you would use for catalytic hydrogenation. The second type of reducing agents are where you add two H plus and two electrons. We call these dissolving metal reduction. We're going to talk about all of these. And then the third type is where you add one H minus followed by one H plus and that is a metal hydride reduction. So I can't emphasize enough the importance of the reagents in this chapter. You will use them over and over and over again when you're doing synthesis. Alright, we still have two minutes. So we're going to talk about all three of these in the same order that they're appearing right here. So we'll first talk about catalytic hydrogenation. And we're going to talk about addition of hydrogen to alkenes and then we'll talk about addition of hydrogen to alkynes. So what you do when a catalytic hydrogenation is you add the elements of hydrogen on each side across a double bond. And I'm deliberately showing stereochemistry here. What type of addition is that when the two hydrogens come in on the same side? Yes, so this is a stereoselective syn addition. So that means the hydrogens come in from the same side of the alkene. Need to know that. Highly exothermic reaction but requires a catalyst because of the huge energy of activation. The catalyst changes the nature of the transition state thereby lowering energy of activation. We'll talk more about that next time.
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This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: 00:54 - Mechanism of Hydration 07:13 - Important points about Hydration 12:03 - Addition of Bromine and Chlorine to Alkynes 15:08 - Hydroboration/Oxidation of Alkynes 28:59 - Designing Synthesis: Part 1 37:10 - Introduction: Oxidation & Reduction 38:19 - Recognizing Oxidation and Reduction of Organic Compounds 47:20 - Reduction Reactions 48:55 - Addition of Hydrogen to Alkenes
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10.5446/21612 (DOI)
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So what it's looking like, what it's looking like, we'll see how it goes. So everybody knows we have a midterm coming up. It looks like it's going to be through Chapter 15 for the midterm. This is going to be a really hard midterm. And so, you know, a lot of synthesis. So last year, we had spec plus this stuff. And so last year, we had spec plus this stuff. And so I couldn't ask as much synthesis because spec takes time, right? There's no spec on this test. So that means there's going to be more synthesis, right? So what you want to do is you want to do as much synthesis as you can. So do the sapling synthesis. Come straight at the end of each chapter. There's a synthesis section where it mixes reactions from all the chapters. You want to do that. Those are the things you want practice and synthesis. Okay? Questions? Anybody? Before we get started. All right. So Chapter 15, really different. So we had a little bit of terminology we were talking about. Feature of radicals, some terminology, bromide ion, bromine atom, bromine molecule. Let's talk about some general features of radical reactions. Because we're going to have some mechanisms in this chapter. Two. Two possible mechanisms from this chapter. And three possible reactions from this chapter. So there's three reactions we're going to take away and use in synthesis. There's two possible mechanisms from this chapter. All right. So radicals undergo two common reactions. They react with sigma bonds and they add to pi bonds. Here's what the arrow pushing looks like. You actually have seen this before. It was in one of the chapters in 51A. When we were introducing reactivity, we talked about homolytic bond cleavage, heterolytic bond cleavage. I didn't really emphasize it because I think this is a whole world unto itself, radical chemistry. The arrows are really different so I didn't really have students have to learn that. So the arrow pushing is completely different. So now remember when we're doing this reaction, we're breaking the carbon-hydrogen bond homolytically. That means one electron goes to this carbon. The other electron is going to combine with the unpaired electron on X and it looks like they're kind of combining midair. That's the way we draw the arrows for that. And then once you do that, you get a CH3 radical plus HX. So whenever we're breaking a bond in radical chemistry, we're going to break it homolytically. One electron goes to carbon, one electron goes to hydrogen. The electron that belongs to hydrogen keeps that electron and it combines with this unpaired electron to make a new HX bond. So once we have those two electrons, we have a new bond and that's the bond right here. So that's one type of arrow pushing. And then the second type is where a radical attacks a carbon-carbon double bond. And we're going to see both types. Alright so again, we're going to break the carbon-carbon-pied bond homolytically. So one electron is going to go to this carbon. The other electron from this carbon on the right is going to combine and it looks like it's combining midair to make a new sigma bond. So that's the arrow pushing and all of the mechanisms that we do in this chapter are going to be some combination of that arrow pushing. So the radical goes right here. So notice when we're doing these radical processes here, we start with a radical, we end with a radical. We start with a radical, we end with a radical. Alright so radical mechanisms have three parts. So very likely that I will put a radical mechanism, I'll give you more details on Monday. And you have to put things into the right spot. So there is an initiation, that can be one step or it can be multiple steps. So there's initiation, there's propagation and there's termination. And so if I give you a radical mechanism on this upcoming midterm, I will have this already written for you. Initiation, I will have it propagation and I will have it termination. And there's reactions and there's problems in sapling chapter 15 where they have you categorize reactions as initiation, propagation and termination. And I'll show you what to look for for that. But if you have the right reaction and you put it in the wrong spot, you don't get points for it. So you have to be able to recognize what type you have, what type of step you have. So initiation, reactive intermediates generated. So in initiation, we start with something that's not a radical and we break the bond homolytically and we make two radicals. That's the initiation. And sometimes that takes a couple steps to do that. Propagation, the reactive intermediate reacts with a stable molecule to form another reactive intermediate and the chain continues until the supply of reactants is exhausted or the reactive intermediate is destroyed. So these radical chain, so it's like every time the reaction, we get one molecule reacting, then it starts the chain again. And so every time it does the process, it's another link in the chain. Termination steps or side reactions that destroy reactive intermediates and tend to slow or stop the reaction. So we'll see examples of each of these. I first want to talk about halogenation and then we'll look at that mechanism. Chlorine or bromine will react with alkanes in the presence of lighter heat or added peroxide to give alkyl halides. So this is the first reaction that we want to talk about. And this is an important reaction because it allows us to take an alkane that is completely unreactive and once we put a chlorine on that alkane, now we have a functional group and now we can turn that into other functional groups in all ways that we've learned. So we have an alkyl halide. We can do reactions from chapter 7, chapter 8, chapter 9, chapter 10, chapter 11 and chapter 12, right? If we just have ethane, for example, there's nothing we can do with it. It doesn't have a functional group. So this allows us to put a functional group on an unreactive molecule. So here's an example here. This is methane plus chlorine and you get a big mixture here. This is high temperature. Starts this reaction. High temp. Light. Usually, a light of a specific frequency or an initiator. And so the initiators that we're going to be using in this class are usually peroxides. So this peroxide is a free radical initiator or just a radical initiator. All right, so you need the chlorine. You need high temperature, heat or light. Now what I normally do on my exams is I will show H new and that's a trigger to you to make you think, okay, this means it's a reaction from chapter 15. It's a radical reaction. That helps you out. Because I'm sure as of right now, all these reactions are swimming in your head right now. It's kind of hard to keep them straight in some ways. The second example uses bromine and this is light and temperature to get this reaction to go. So this is not necessarily easy to do. And this reaction is much more selective. We'll talk about why coming up. You actually only get one product here. So chlorination, not a selective. We'll see that coming up. Much more selective. All right, so this is a radical chain reaction. And I'm going to do the mechanism for example one and then we're going to do an abbreviated mechanism for example two. We'll do both of them. And I'm not going to show a formation of all of these products. I'm just going to show you a few here. Okay, sorry about that. I went the wrong way. Okay initiation is where the radical is formed to start the process going. In order for our free radical chain reaction to happen, you only need one radical to start. And if that radical sticks around a long time, I mean if it's there and it's going to create new radicals, that reaction will keep on going. So it's not, when you do a radical reaction, you're not hitting it with light and all the radicals are forming at the same time. It's one molecule at a time and every time you complete the reaction, you get another link in the chain. So for a radical formed, and this is going to always be where we break a weak bond. Alright so here's some examples in the top corner of weak bonds. So you notice bond association energies are all really universally low here. Fluorine fluorine bond 38, chlorine chlorine 59, bromine bromine 46, iodine iodine bond 36, peroxide 51, this is tert butyl peroxide, di-terp butyl peroxide 38. And what is something these all have in common? Besides the fact that they have small bond association energies, what do they all have in common? Well I think I heard it, both of these atoms have lone pairs and they're right next to each other. Okay so this has lone pairs, that has lone pairs and they're right next to each other. And so what happens with those lone pairs is they want to, they repel each other. And so they want to move further away, because there's electron-electron repulsion. And when they move further away that lengthens the bond and makes it weaker, right? So this goes all the way back to 51A. Strong bonds are short bonds, weak bonds are longer bonds. So the electron-electron repulsion from those lone pairs is going to want to make those things pull away from each other and it's going to weaken the bond. So that's what's going on. So let's throw some lone pairs on here so you can be reminded of that. I'm having too much fun drawing lone pairs here. So good point to make about weak bonds here. I like this because I can actually write these a little faster than I can with a pen for the transparencies. How about that? Okay, so you see a whole lot of lone pairs going on. So that makes a good point. So what we have is two heteroatoms. And the other thing that's really good is that when I have my hand, my hand is completely covering this and it's not covering it at all up there. So that's another thing I like about this tablet here. So two heteroatoms bonded together both with lone pairs. So that makes it for a weaker bond and a weaker bond is easier to break. So when we have chlorine, so chlorine, chlorine, that's on our weak bonds. So the radical is formed and so we're going to make a chlorine-chlorine bond or we're going to break it homolytically. So we have chlorine. So we start off in an initiation, we start off with a neutral molecule that's not a radical and we end up with two radicals. And that's what starts the process rolling. So how do we know if something's an initiation step? We start off with something that's not a radical and we create new radicals. That's how you know if it's initiation. Propagation. So what's going to happen here is we have methane, so I'll draw a methane and I'm going to draw out one of the bonds for methane. And the chlorine radical that we formed in the initiation. Now we're going to do the same arrow pushing we did on the previous page. The chlorine radical is going to abstract that hydrogen. Remember when we do radical reactions we're going to break each bond homolytically. So we break that carbon-hydrogen bond. Carbon gets one electron, hydrogen gets the one electron. The electron that hydrogen gets combines with the unpaired electron and chlorine to make a new hydrogen-chlorine bond. So we get hydrochloric acid as our side product. And then the methyl radical that we just formed, it's going to grab a chlorine. So we're going to break this chlorine-chlorine bond homolytically. The electron from the chlorine on the left is going to combine with the unpaired electron on the methyl radical and we're going to get our product. And that's the other thing that we're going to see in a propagation step. So that's one chain, that's one link in the chain. And as you can see, what we've done here is we've regenerated the radical that we started with. So this is going to come in and it's going to, there's a link in the chain and it's going to come in and it's going to do it again. It's going to keep cycling through. So we regenerate the radical we started with. You can, and I'm going to show that, that's a termination step. Okay, I'm going to show that in just a second. So we regenerate the radical that you started with. And the other thing I want you to notice is that we've always keeping the same number of radicals in propagation steps. So in this one, we start with a radical, we end with a radical. Here we start with a radical and in a neutral molecule we end with a radical, I mean, or a non-molecule with all electrons paired. So start with a radical and with a radical, start with a radical and with a radical. So when you're sorting those problems and sapling into boxes, that's what you're looking for. The number of radicals stays the same. One here, one here, one here, one here. In the first one we started with none and made two. That's what makes that an initiation step. So note, the number of radicals stays the same in propagation steps. So definitely want to make sure that you look for that. Now termination is really the opposite of initiation. In initiation you start with something that's not a radical and you break it into two radicals. In termination you combine two radicals and you make it into something that's not a non-radical. That's a termination step. So that's what you're going to look for when you're doing this ear sorting. So pretty much any radical that we have here can combine with any other radical. So for example we could have a chlorine radical and this is to answer your question combining with a methyl radical. So it looks like that. That would give you the product that we're going to get anyway. It's just made by a different pathway. That would give you methyl chloride. We could have two methyl radicals combining. That will give you ethane. So that will give you ethane. You can also have two chlorine radicals recombine. So these end up being some side products that you get. Well the first one's not a side product. The third one's not a side product but certainly ethane is not something that we're trying to make. Usually we don't get very much of these termination steps because let's imagine that we start off with one molecule of chlorine breaking. So let's imagine we have just one molecule do this. So we only have two chlorines here. Two chlorine radicals. What are the chances of those two chlorine radicals? They're going to be stirring in that reaction. They're going to be moving around doing this reaction over and over again in the propagation. The chance of those two actually interacting and colliding and recombining is very small. So there will be a lot more propagation than there will be termination. You still do get these side products. And so that's why it's not a very complete reaction because no one's going to want to have to separate all of these possible products here. So you see we have a lot. Here we have methyl chloride. Now you can imagine to form this one right here, a radical would come and remove another proton from methyl chloride. That's how we would get some of this. To get this, this is chloroform. We would have a radical come and remove another hydrogen from carbon here. And then that's how we would form this. You could do that four times. You could replace all four hydrogens with chlorine. And here, this product right here would be from the ethyl that we formed in our termination step. So you get a lot of, it's kind of a messy reaction here. So the competing propagation step here, I'll show formation of the dichloromethane here. So you can see what I'm talking about here. If this comes in and grabs a proton, instead of from methane, it grabs a proton from methyl chloride, then you form this radical. And now what's that radical going to do? That radical is going to come and grab a, it's going to come in right here. Where are we? It's going to come in here. It's going to grab a chlorine and that's how you get dichloromethane. Let's show that. So kind of a messy reaction here. Just my single headed arrows here. Everybody see how that's formed? So what did we see? We said about 80%, we get about 80% methyl chloride in this reaction and we get about 20% of these other little side products that have to be separated. One of the ways to get this reaction to go a little bit better and a little bit cleaner is to keep the concentration of these side products low. Keep concentration low by using a large excess of methane. Alright so since methane is a gas, you would use a large excess of methane and then that will increase the amount of methyl chloride you get and some of these other little side products will be much less. Question about that mechanism, anybody? Alright so as we say on the next page, this isn't a very good reaction because it's not very clean. It's not the best way to synthesize alkyl halides, there are better ways but it's still useful because it is the only way to convert an inert alkane into a reactive compound. It's the only way that we know to take an inert alkane like propane, ethane, methane and add a functional group on it. Once we put a chlorine or a bromine on there now we can take that and do all the other reactions we know that we can do with alkyl halides. But until we do that we're stuck. So this is, even though it's not a very good reaction it's the only thing we have. So another better way to synthesize alkyl chloride, we learned in chapter 10, right? If we do it this way we don't get a million little side products. So that's what we would do if we wanted to make an alkyl halide for alkyl bromides, we would use HBR. So there are better ways. That's the difference here though. Are we starting with a compound that doesn't have a functional group? No, we're starting with a compound that's an alkene that has a functional group. It has a functional group that can be converted into other functional groups. So this is different. It's a better way to make alkyl halides but there are starting material has a functional group right here. There's a functional group, that alkene is a functional group and so we're just converting it to another functional group. If we have an alkene we have no functional group. This has no functional groups. So we can't take base and remove that proton because it has a pKa of 50. So this is the only way that we have to put a functional group on there and then once we do that we can convert it into other things. Questions so far? Anybody? Let's look at the second mechanism. This one's a lot cleaner. So we take tertiary butane, bromine, light and heat and let's draw our product. Single product here, we don't get a lot of different products here. Alright so initiation, erratical form, we always break a weak bond. We got a weak bond here. Did I not leave you time? Sorry about that. Okay so we're going to break a weak bond. That's easy, break a weak bond homolytically. We start off with a non-ratical. We end up with two radicals. Now again I want to make the point that not all of the bromine, not all of the molecular bromine bonds are going to break. Just a few of them. Not all of them are going to break. We only really require one to break and that's enough to get all of our starting material converted into products. So propagation and I drew some of these already to make it a little easier. I should probably draw that bond a little longer. So we go here. So tert butyl radical plus HBr. And then the tert butyl radical comes in. It's really the same mechanism here. Grabs of bromine. So we still have molecular bromine. We still got this bromine in here that hasn't been broken apart. And this is going to come and grab a bromine from that. And when it does that it forms our product and we always want to look for this. It's going to regenerate the radical that we started with at propagation. So always the last step here is going to be regenerating the radical that we started with and definitely you want to look for that. So this one here. That's what we started with. And now it's going to cycle back through again. So most of the bromine is going to be broken apart this way, not this way. Questions I hear a lot of. Oh, what did I do? Oh I forgot. Yeah, yeah, yeah, thank you. I knew I did. Which means one of two things I've either scrolled too quickly or I made a mistake. How about that? That's looking too much like a dog. Let's try and fix that. How about that? Is that better? Okay. Regenerate the radical that we started with. All right. Termination. Just destroyed by recombining any two radicals here you fill in. There's three possible. And by the way on the test I will have an initiation section. I will have a propagation. I will have a termination. And what I always do on the test is I say show me one termination. That's all I want to see. You don't have to draw all three. I just want to see one. So whatever one you think you like the best. That's what you can include. All right. So possible mechanism. Radical halogenation. I will have some sort of alkane. I will have either bromine or chlorine and light and heat and all that. That's one possible mechanism for a midterm two. All right. I want to say something about selectivity. Very selective with bromine. It turns out that bromine is a much more selective reagent than chlorine and we're going to explain why that is. So let's look at this. We've got one tertiary hydrogen. Let's remind ourselves with a tertiary hydrogen as a tertiary hydrogen is a bonded to a tertiary carbon. That carbon is bonded to three other carbons so it's a tertiary carbon. And we have how many primary hydrogens? Nine equivalent tertiary hydrogens. Our primary hydrogens, nine primary hydrogens. So we've got nine to one ratio of primary tertiary hydrogens and we still get no primary hydrogens abstracted. We get no product that comes from our primary hydrogen being extracted. So statistically you are nine times as likely but you don't get any. You don't what do you not get any. You don't get any primary hydrogen abstracted so you don't get any of this product here. This product would result from a primary hydrogen being extracted. Any one of those nine would give you this product and you don't get any of that. So let's put a big X through that. None of that product is formed. So we need to explain why that is. There's two factors that we need to talk about to explain this. Number one is the relative stability of the radicals formed. So we have tertiary radical more stable than secondary radical, more stable than primary, more stable than methyl radical. So if we remove one of those primary hydrogens we're forming a primary radical. And so maybe not surprising that we don't get any of that formed at all because we know that primary radicals are very unstable. Similar to carbocation primaries, very unstable. The other thing that's not obvious is that we have to look at the ease at which the different hydrogens are removed and in order to do this you can look at the bond association energies and energy of activation. So we actually have to do some calculations. We're not going to do any calculations. So but I want to show you that with the relative rates of hydrogen abstraction by halogen atoms for bromine primary is 1 to 82 to 1640. So tertiary forming a tertiary radical is 1640 times more likely than forming a primary with a bromine radical. And since we only have a 9 to 1 ratio there's not a chance statistically that we're going to be removing one of those primary hydrogens. The selectivity for tertiary is way too great. Chlorine on the other hand we're going to just relative rates, we'll have 1 for primary, 2.5 and 4. So if we did this exact same reaction with chlorine we will get some of the primary product, and that's because there's only a 4 to 1 selectivity for tertiary over primary is 4 to 1 and we have 9 times the number of primary carbons so we will get primary here. So much more, much less selective. And you're beginning to see why I tend to favor bromine because it's a better leaving group, it works better in this reaction and it's better in a lot of different reactions so I tend to favor it. Alright so why is the bromine atom so much more selective? It seems like it just should have to do with carbocation stability but it's not. Remember we're doing other things in this reaction. So it turns out if you compare transition states and activation energies for the abstraction of a hydrogen atom by bromine radical versus a chlorine radical you will find that. Number one, abstraction of a hydrogen atom by bromine is endothermic while abstraction of a hydrogen atom by chlorine is exothermic. This sounds crazy difficult, it's really not that bad. And number two, the transition states for the endothermic, the bromination have a larger energy difference than those for the exothermic chlorination even though, and that shouldn't be on that page, but even though the energy difference in the products is the same in both reactions. Okay it's like whoa, wrap your head around that, right? So let's see if I can explain this graphically here for you. So what we said on the previous page is abstraction of a hydrogen atom by bromine is endothermic while abstraction of a hydrogen atom by chlorine is exothermic. So here is alkane and chlorine exothermic. So this radical here is down here. And then if we do bromine it's endothermic so this radical is higher in energy. Okay so let's label that. This is exothermic reaction and this is endothermic reaction. The rate of the reaction is going to have to do with the height of that energy barrier. How do we know about the structure of the transition state in an exothermic reaction? Does it look more like the reactant for that reaction or the product? It's closer in energy to this and we're starting off with one thing. We're starting off with one thing, we have a very exothermic reaction. The difference in the energy between these transition states is so close because it looks more like the alkane than it does the radical. Very very close in energy. So what that means is that when you do the chlorination you're going to be equally likely to take all three of these pathways. Yes, the red pathway down here is lower in energy but these are all very close by so they're all accessible. Over here we have an endothermic reaction by Hammett's postulate. We know that in an endothermic reaction the transition state looks more like the products of that reaction. And so since there's a big energy difference here between these three products there's also going to be a big energy difference here between the transition states. And so you can start to see now that with bromination this lower energy pathway is so low and these are much too high for it to overcome that energy barrier. So all the molecules are going to take that pathway because there's a big energy difference here. Here there's not, this is a small energy difference. So we definitely want to label that a little better here. Let's label that. So exothermic reaction therefore the transition state resembles. And we're only looking at one step here. So the transition state resembles reactants more than products. And an endothermic reaction the transition state resembles products more than reactants. And so if you look here this is a really small energy difference between these guys. These are two tiny little arrows. I don't know if you're going to be able to see those but very small energy difference. It is less than 1 kcal per mole. So three very accessible transition states and so you're going to get a big mixture here. And here these guys here this is a large energy difference. And what do we have here? This is about, I may be exaggerated a little bit more. This is 2 kcal per mole. And that's enough that you, so if you add 2 kcal per mole, if you've got tertiary versus primary that's 2 kcal per mole plus 2, we're talking about 4 kcal per mole. That's a really large energy difference for transition states. So we have the large energy difference here. This one has a much bigger energy difference. Therefore the rates of the reactions will be markedly different. And this is a really good example of the point that when you're talking about rates of reaction it does not have to do with the intermediates. These intermediates and these intermediates have the same energy difference. And if it was only because of that then we would have the same product outcome whether it's bromine and chlorine. It has to do with the height of the transition state here. That's what's key. Alright so here's an example here to show you what this means, difference wise in selectivity. So here we have bromination, here we have chlorination. With bromination we get one product 82%. With chlorination we get 26% of this product, 22% of this product, 22% of this product, 14% of this product and 17%. And you can actually predict these percentages by taking into account the difference in selectivity of chlorine versus the number of hydrogens that you have and you can actually calculate these differences. The textbook we had before this, had you do that, this textbook doesn't have it so I'm not going to have you learn that. You'll be glad about that. You're very glad. It's not that hard but you're glad. Alright questions on bromination of alkanes or chlorination of alkanes. That's reaction number one from this chapter. Radical substitution of benzylic and alec, that's reaction number two in this chapter. We are going to skip the mechanism here. But you need to know the reaction. Poor synthesis. Why am I having you skip the mechanism? It's a confusing mechanism. It has both single headed arrows and double headed arrows and it's just so hard to wrap your head around when you're just learning organic chemistry for the first time. How do I know that because I remember having to memorize this mechanism. And a lot of mechanisms that I didn't really need to memorize. So I'm having you, I'm selectively having you memorize certain things. As little as possible though. So we're skipping the mechanism and you don't need to know that. Recall that allyl and benzyl radicals are both more stable than tertiary radicals. We know the more stable the radical the faster it can be formed. So a hydrogen bonded to either benzylic or alelic carbon can be preferentially be substituted in a halogenation reaction. So again, these guys are more stable than tertiary. So that means that if you have a choice between removing a tertiary hydrogen or benzylic or alelic, benzylic or alelic will win. So here's some examples here. Br2, we can make this radical right here. We won't form a primary radical, we'll only form that one. And then if we carry that on, we will get benzyl bromide. A substituted benzyl bromide. So the bromine will go in the benzyl position, nowhere else. And you put that bromine. If we have allyl, then we can put, we have a choice between vinyl, hydrogen or allyl. So here's vinyl right here. Are we going to form any of that? Not when we've got allyl that we can form, right? So that's way better. So that means that we can form the allyl radical. Here we can convert that into alyl bromide. So who sees a competing reaction that can form with this, these two? Who sees another reaction that's competing with that? From chapter 10. Yeah, and you know, bromination of an alkene is an extremely fast reaction. You guys did this in the lab, didn't you? How fast was it? It was really fast. So how are we going to do this when we can do this just as fast? Okay, so I'm going to give you a different reagent for this. We're not going to use this reagent. We're going to give you a special reagent for this, then I want you to use instead. And that's because we have competing reactions here. With bromine, we can form a bromonium ion. Let's remember this. We don't want to forget this. This is midterm two material, right? Not to bring up an unpleasant subject, but you know, right? Nobody likes taking tests. In graduate school, in chemistry, you take one year of classes and then you work in a lab for the rest of the time while you earn your PhD. And I remember thinking at the time, I've only got one more year of classes in me. I cannot do this for two years. I just was so burned out on taking tests. So I haven't had to take a test since then, and it's a beautiful thing. Because nobody likes taking tests. All right, so remember this, okay? So that's a competing reaction. That's a competing, very fast reaction. So really, let's not use bromine for this. Even though Smith uses this a lot in synthesis, I want you to not use this reagent. And that's the reason why. We'll stop right there, and we will finish chapter 15 next time. So this is the reagent I want you to use instead.
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This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: 01:30 - General Features of Radical Reactions 01:54 - Reaction of a Radical X with a C-H Bond 03:47 - Reaction of a Radical X with a C=C Bond 04:58 - Radical Mechanisms 06:40 - Halogenation of Alkanes 09:16 - Mechanism 1 27:05 - Mechanism 2 31:24 - Selectivity and Stability 43:52 - Radical Substitution of Benzylic and Allylic Hydrogens
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10.5446/21613 (DOI)
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Okay, we're going to finish Chapter 15 today and then we will start Chapter 16. Everybody knows there will not be any Chapter 16 on the exam, right? But we will be covering through Chapter 15. I will not be making the midterm deliberately cumulative. The final will be deliberately cumulative, but of course, when you're doing synthesis problems, you need to know all the reactions that we've learned. Okay? All right, questions before we get started? Anybody? All right. Okay, so we left off last time talking about radical substitution of benzylic and allylic comhydrogen, so allylic and benzylic brominations. And so your book uses two reagents for this. They use bromine and light or heat. So bromine and lighter heat, bromine and lighter heat. And what we're going to learn is we certainly learned in Chapter 10 that there is a competing reaction for this where we do make a 1, 2-dibromo compound. That's very fast reaction and competing. And what we're going to learn is that in some, in Chapter 18, we're going to be actually bromidating the aromatic ring. And so we want to avoid these products from, these side products from forming, this kind of thing. So although the book is using this in a lot of different places, I want you to use a different reagent, and that is n-bromosexanimid. The good news for that is that we can have an abbreviation nbs. That is nbs, not nbc. So nbs, n-bromosexanimid is the reagent. So we're going to use nbs, and we use a peroxide. So any of those peroxide initiators, this is an initiator, light or heat and peroxide. So the nbs is our source of bromine. And peroxide is a radical initiator. And this is the reagent that I want you to use instead for allylic and benzylic bromination. So here, our product is going to be this only. We're not going to get any side product, no side product. The side product that we would get here would be anti-addition of bromine to the double bond, which is not a radical process. All right, and likewise, when we have the benzylic hydrogens that we can remove, we will only get the benzylic hydrogens. So you'll appreciate the second one more when we get into chapter 18. Bromine itself is not going to add bromine without a catalyst, but other rings, other benzene rings with different substituents will add bromine to the ring. And so we don't want these competing reactions to take place. So that's why we're going to use nbs instead. So on test, use nbs, R-O-O-R, and heat or light, light or heat for allylic and benzylic bromination. All right, now the good news is, we said last time we're not going to know, you don't need to know the mechanism for this reaction. It's a complicated mechanism. It has fish hook arrows and it has double headed arrows. So it gets a little involved and that's not something I want you to take your time to learn. So we're skipping that. So no mechanism for this reaction. All right, we're going to take a brief pause to talk about the stereochemistry and then we're going to talk about the third reaction that you need to know from this chapter. So the first reaction, bromine and heat or light to take an alkane and make it into an alkyl halide. Remember you're going to form the most stable radical. So that's going to lead to the more substituted alkyl halide and bromine is much better than chlorine for selectivity. The second reaction is allylic and benzylic bromination where we're going to use nbs, peroxide and heat or light. That's reaction number two. We need to know the mechanism for reaction number two and then we're going to do a third reaction from this chapter. But first let's talk about stereochemistry. Because free radicals are planar and sp2 hybridized racemic mixtures are obtained in reactions that form a stereocenter and that makes sense because these are radicals sp2 hybridized. So we have a plane, we have a p orbital on the top and on the bottom with a single electron and so things can come in and attack from the top and things can come in and attack from the bottom. We are going to get both. So we want to be able to make sure to remember that. Alright so here we have a chiral reagent. A chiral reagent. And we're going to form a secondary radical. We can go either here or here. We'll form a secondary radical by loss of a secondary hydrogen. We will not be able to form a radical, a primary radical here. And so then let's look at our intermediate. Let's look at the radical intermediate. We know that that is sp2 hybridized. So carbon, the carbon from the radical and the first atom are all in the same plane. So let's mark those. So this carbon, this carbon, that hydrogen and that carbon are all in the same plane. And let's go around and do that one also. So these guys are all in the same plane. We have our unhybridized p orbital. I'll change the color so we can see that I probably did not allow enough room. This is a single electron. That's the structure of a radical. And now so the bromine can come in. This radical is going to grab a bromine from a molecular bromine from a BRBR. And if it attacks at the top face. Here's the product that you're going to get. Here's bromine coming in from the top. Remember, once that bromine bonds to the carbon, it's now tetrahedral. It's not planar any longer. And if it comes in from the bottom, if the bromine comes in from the bottom, and this is the first time we've used this word, but it's called the face, bottom face, top face. And if it comes in from the bottom, then this is what the product looks like. And so if we're starting with achiral reagents and there's no chiral influence, then that means that if we have a stereocenter in our product and we do, there's a stereocenter right there, that the mixture must be racemic. So product has stereocenter. Therefore must be racemic. So if you were thinking you were going to get away with thinking about stereochemistry, we're not done yet. So definitely stereochemistry we have to worry about here. So this is a racemic mixture. If we want to get a single enantiomer, we have to have some chiral influence and that's what we saw with the Sharpless Apoxidation. There was a chiral catalyst that formed in that reaction and so we could get a single enantiomer. But unless we have that, if we don't have that, then we're going to get a racemic mixture. So in addition, loss of optical purity will occur, substitution occurs at a chiral center. So just like in chapter 7, we didn't want to use SN1 if we didn't want racemization, same thing here. So if we start with something that's optically pure, we have this chiral center here, optically pure. And generally speaking, making things that are optically pure is a lot more difficult and if we tried to do this reaction with optically pure, once we do that, let's draw our intermediate, we have again a planar intermediate just like with the SN1 reaction, we had a carbocation, this is also a planar intermediate. Only difference here is we have a single electron in that unhybridized P orbital and so their intermediate is achiral. So achiral intermediate does not matter that we started off with something that was optically pure, we get racemization. So we get loss of optical purity. And so when we do this reaction, we're going to get two products. One is going to come in from the top and it's going to come in from the bottom. So let's draw both of those. And I'll just abbreviate the benzene ring with pH. So here's the product if the bromine comes in from the top. Here's the product if the bromine comes in from the bottom. So here's the bromine coming in from the bottom, that's the enantial. So something to keep in mind when we're doing radical reactions. We do want to avoid this reaction if we have a chiral center that we're trying to do substitution on. All right, questions on stereochemistry? Anybody? Yes? This is not like that. Yeah, so we're not making a brimmonium ion here. Oh, we're talking about a brimmonium ion attacking from the bottom face, yeah, we used that same terminology. Yeah, I just haven't used it before. I don't know why I started using it now. It seemed like a good place to start. All right, we said there was three reactions that you will need in synthesis. And this is number three. Radical addition of HBr2 and alkene. Now we know what happens when we add HBr2 and alkene. What type of addition is that? Merconicob or anti-merconicob? Merconicob, so the bromine goes on the most substituted side. So this we already know, let's draw the product here. Merconicob product. So this of course is chapter 10. Now if you do the same thing, you take the same alkene, you take HBr and you add a radical initiator. So peroxides are radical initiators. And when I give this reaction on the, and typically you need either heat or light. Sometimes you don't, but I will usually just for, just to make it easier for you, if I'm wanting you to do a radical reaction and I'm having you predict the product, I always write HNU, okay, so that you'll know it's radical. But you can certainly also do this with heat. But I will always use HNU when I want you to predict a radical product. And so this is the only difference here, I mean, is this radical initiator and what you end up getting is anti-merconicob addition. So anti-merconicob. Well that's really, you're solely able to have that. Because sometimes we want anti-merconicob addition. So we have now two reactions that do anti-merconicob, this one, what else, what's the other one? Hydroboration, right? Both of those do anti-merconicob. Hydroboration gives you anti-merconicob addition of water, this gives you anti-merconicob addition of HBr. So those are only two, that's all we're going to learn all year, you will need those over and over again since this is, so it's a really important reaction. So this is a mechanism type two that might be on the test coming up. So we're going to have a radical mechanism on this test. We're also going to have other mechanisms that are not radicals, but you have really a choice of two in this chapter. Reaction number two, we're not learning the mechanism. So this one is actually, so initiation, same idea. When we initiate, we break a weak bond, and our weak bond, we saw a chart with weak bonds in the notes for this chapter, and a weak bond is an oxygen-oxygen bond. So we'll start with our radical initiator. And the name of this tells you what's the very first, I put that in the wrong spot, let me fix that. Yeah, you don't want to do that, don't do what I just did. Okay, this is going to be two steps of initiation. So what do you do in the initiation? You break apart the weak bond in the radical initiator, that's going to be the very first step. So it's an easier way to remember that. So we're breaking this homolytically, one electron goes to oxygen, and one electron goes to the other oxygen. So we're breaking that bond, and we're going to form two R0 dot, two alkoxy radicals. And they all alkoxy radical. And I'm missing my lone pairs here. So let's go ahead and add those. And what we're going to do is we're going to actually make, we're going to make a bromine radical here. So this R0 radical is going to grab a hydrogen from HBr. We're going to break this HBr bond homolytically. One electron is going to combine in midair with that unpaired electron from oxygen. And then we're going to form a new oxygen-hydrogen bond. And this bromine radical, that's the one we're going to use for this reaction. That's the one we're going to start with in the propagation and keep reforming. Okay, so that's initiation. When we add a radical initiator, it's usually going to be two steps. Sometimes it's even more than that, but two steps. Why didn't we just break the HBr bond, by the way? Why didn't we just break this bond? Why did we have to add this? Any ideas? What do you think? Well, yeah, go ahead. Exactly. And what is it going to do instead? It's going to re-protonate the pi bonds. So those two reasons, yeah, exactly. All right, so what this is going to do is the second type of process we talked about at the very beginning of this chapter. The first one was abstracting an atom from another molecule, and this one is adding into the double bond. So here's our bromine radical that we just made. And it's going to add into the double bond. So we're going to break the double bond homolytically. One electron is going to combine with the bromine, just like that. We want to form the most stable radical, so that's why I'm breaking it that way. So I want the radical to go on the secondary carbon, not the primary carbon. And what you want to check for is that all of your propagation steps, we start with one radical and we end with one radical after each step. If you start with something that's not a radical and you make two radicals, well then it's not a propagation. It's an initiation. If you start with two radicals and you end up with no radical, that's a termination. So that's what that looks like. And then, and this is, so again, and I'm going to redraw this. Now our job here is to regenerate our bromine radical that we started with. So the bromine radical that we use in the propagation is really, it's starting with one that came from the initiator, but we don't continue to form the bromine that way. We continue to form the bromine in the way that I'm going to show you right now. So we're going to come and grab hydrogen from HBr. There's the hydrogen right there. We just formed that new bond, CH2Br, and we regenerated our bromine radical. Always want to check for that. That's what we started off with. There it is right there. We regenerate that. And that's one link in the chain. It cycles through one molecule at a time. Boom. Just like that. Very surprisingly fast, many of these reactions. Termination radicals destroyed by recombining. You can take any two radicals we have here and recombine them in the termination steps. So I'll let you fill in. On the test, I will ask for one termination. So you can pick whatever one you, you're going to have your pet termination reaction. Maybe you'd combine two bromines together. You can do that. All right. Questions about that mechanism? Anybody? In the propagation step, bromine adds to the SP2-carbotone butene that's bonded to the greater number of hydrogens to form a secondary radical rather than to form a primary radical. Why? So why no? And you already, we already said why. But let's write, let's fill this in here. Why no secondary product? Well, if we would form secondary product if we form this radical and we don't want to form this radical because it's not as stable as a secondary radical. There's a big difference. And so because the transition state leading to the secondary radical is lower in energy than the transition state leading to the primary radical. How do we know what the transition state looks like? We use Hammond's postulate. The transition state is going to look like either the reagent or the product, whatever it's closest in energy to. Since this is an endothermic reaction, it's going to look closest to the product which is a radical. So anything that stabilizes the product, radical, is going to also stabilize the transition state. So an alkyl peroxide is a radical initiator. There's a bunch of different ones. Because it creates radicals without a peroxide, the preceding reaction would not occur. Initiators have weak bonds that readily undergo homolysis. So I'll give you just a little bit more reactions here. This is 44 kcal per mole. You might recognize that reagent as one of the reagents that is used in the Sharples epoxidation. So they're guaranteed there's some sort of radical process during that reaction. Why I didn't show you the mechanism. These radicals are reacting in a lot of those reactions from chapter 12, but they're way too complicated for this class. So that's 44. Do you need to memorize these numbers? No. I'm not big on numbers. What I want you to recognize is we've got the two hetero atoms, both with lone pairs right next to each other. That's going to make for a weak bond. This is benzoil peroxide, 30 kcal per mole. And this is AIBN. It's very low also. I forgot to look up the number for that. Azo-Bis, isobuteronitrile. That's another common initiator. So we call this the peroxide effect. If we don't add peroxide, we get a polar mechanism. We get Marconi-Covidicin. If we add peroxide, we get anti-Marconi-Covidicin and a radical process, not polar. So we call this the peroxide effect. And this effect occurs only with HBr, not with HCl or HI. Why? And the reason is that if you calculate enthalpy change for each reaction, so for a radical addition of HBr, the first propagation step is exothermic. Second propagation step is exothermic. First propagation step for HCl is exothermic. Second propagation step is endothermic. And for HI, endothermic first step and exothermic second step. And it turns out that for the first propagation step and the second propagation step, if both steps are not exothermic, the reaction doesn't go. And you get a polar mechanism instead. So only when all of the propagation steps are exothermic. Can propagation compete with termination? So notice in a termination reaction, we're taking two radicals and we're combining them to make a bond. Is that exothermic or endothermic? Just making a bond, not breaking any, right? Exothermic. So we have this exothermic termination step, which is competing for propagation. If we have any of these steps or endothermic, it doesn't go. So HBr is the only one you're going to use for this reaction. Okay, so HCl or HI, hydrochloric acid or hydroiotic acid, only ionic addition occurs to give Markov-Konikov product. Even if you add peroxide, the proxies are just going to sit there and not react. And if you add peroxide. Alright. And let's draw a line right here. Midterm two material up through here. The last part of this chapter is a little bit topical. I'm going to go quickly through it. I will not be testing you on it. Alright, so midterm two stops right there. Okay, auto oxidation. So auto oxidation, when organic compounds are exposed to air, they react slowly with oxygen to give hydroperoxides. This is known as auto oxidation. It's responsible for the slow deterioration of air in foods, rubber, and paints. So some paint jobs tend to fade more than others. Red is a big one, blue is a big one. That's all caused by auto oxidation. If you keep rubber outside for a long time, it gets all crackly, right? These things like that, these things break apart. And so compounds that are easily auto oxidized or compounds that form especially stable radicals. So that's the things we want to look for. So you can imagine, in the presence of oxygen, this guy right here can form an especially stable radical, right? Tertiary benzylic radical, what could be better, right? So that's going to be especially prone to oxidation. And let me show you what a hydroperoxide looks like. These guys are very reactive and potentially explosive. So we turn this nice benign compound into a peroxide. And peroxides, of course, are going to be especially reactive. Compounds with hydrogen atoms on a carbon adjacent to an oxygen are also prone to oxidation. And so you've used diethyl ether in the lab, right? You have to be really careful with diethyl ether. You have to use it up pretty quickly. And if you don't use it up pretty quickly, then you have to, it will form peroxides, hydroperoxides. So this is diethyl ether, hydroperoxide. Extremely explosive. There's been explosions with ether that's been left out too long. If you use ether in the lab, you'll usually find it in a metal can with a very, especially anhydrous ether. You'll find it in a metal can with a very small opening in the top, really small like that so that not very much air gets in there because we don't want this to happen. But when this has formed and people have not been careful, there's been very serious explosions. One in particular I heard about where it took and moved an entire wall over six feet. That's what the explosion did. So things like that. The other thing that's very prone to oxidation are polyunsaturated fats. So this is linoleic acid. Got to be careful with these guys. This is linoleic acid. Paraparoxide. So not very healthy for you. So let's think of what's happening here. So we've got linoleic acid. Which hydrogen in that molecule is going to be easily form a radical? What would be the most stable radical you could form from that molecule? Where would it be? Give me the carbon number starting from, there's too many numbers here. What do you think? This guy right here, right? Allylic on one side, allylic on the other. Double-E allylic. Very prone to oxidation. Right there. Very very prone to oxidation. And so that doesn't look like the product that we have. Let me just show you very quickly how you form the linoleic acid, hydroparoxide. So what you do is, do not need to memorize this. So this is just for your own betterment as a human being. And your own safety because you're going to be careful about this kind of stuff. I mean polyunsaturated fats are really good for you, but you need to make sure that you don't keep them too long. So we're going to abstract that hydrogen. That's what we would get. And one thing you want to keep in mind, this is, when you form an allylic radical, you have to draw the resonance structure. And this is not just in this last part of this chapter, this is when you're doing allylic promenation, make sure you draw the resonance structure and you will get products from both resonance structures. So we know that allylic radicals are resonance stabilized. We're going to see that at the beginning of chapter 16 also. And there was something in lab last week where we did that and we'll do that again this week. And so I'm just going to go like this and I'm just going to do resonance stabilization. I didn't show you the error pushing for this, but we did talk about this at the very beginning of this chapter. And then what that does is now gives you this radical. What's good about that, what we just did? Why does that make that radical more stable? So we're actually in this resonance structure, we're making that radical more stable. Why is that? That double bond and that double bond are now conjugated. Okay, remember conjugation adds stability. We're going to talk about that more in chapter 16, which we're going to start in a minute here, but this is now conjugated. So it's not only allylic, but it's conjugated. These double bonds are conjugated. So this is now allylic plus conjugated. And so what's going to happen is that the oxygen in the air is a di-radical. It's going to come in here, just like that, right? And then we get this. And that's going to grab a hydrogen from another molecule. Let me change the color here so you can see that a little better. It's going to grab a hydrogen from another molecule of Rh, which is another molecule of the linoleic acid. And so that's one of the reasons why manufacturers like to add saturated fats or hydrogenate fats, partially hydrogenate fats and hydrogenate fats, because if you do that, you get rid of this guy right here. They're more shelf stable. You don't have to keep them refrigerated. Of course, the polyunsaturated fats are definitely much better for you. And so one of the things that other things that manufacturers do is add antioxidants. So you may maybe recognize some of these, BHT, BHA. These are added. And the reason that we use these is that this one, for example, forms a really stable radical. So it removes the radicals that start to form to keep the food safe. And this particular one is very stable because it's so hindered. If we actually drew out all those terpetal groups you would see, this is a hindered phenoxy radical. So it traps any radicals that are formed and that's why we add those as antioxidants. OK. Questions on Chapter 15? Anybody? Yeah, let me just start to save this and go ahead. Say that one more time a little louder. For this one here, not. Well, that's the part of the test. Yes, if you're making a resonance structure in the earlier part of the chapter that's going to be tested on, you would want to draw a resonance arrow. Yes. All right, let's do Chapter 16. Where is Chapter 16? Oh, scared me for a minute there. OK. All right. Now, the first part of Chapter 16, you're going to say, oh, I already know that. We've already talked about that. So some of the first part of this chapter, especially if you had my class before where I talk about conjugation, this is actually the first place that Smith talks about conjugation. And so there's actually some chapters in the end, some problems in the end of this chapter that have you just drawing resonance structures like we did back in Chapter 1. So it seems in some ways a little late to do it. That's why I introduced it a little bit earlier. So this is all about conjugation, resonance, and dyings. So conjugation occurs whenever p-orbals can overlap on three or more adjacent atoms. So we say that we know that, oh, that's too big here. Let's fix that. We know that conjugation makes things more stable, but why? And that's because there's resonance stabilization. So although this is a minor resonance structure, we are actually moving electrons around to help stabilize this molecule. So one end gets the negative charge and one end gets the positive charge. We ran across conjugated carbonyls when we did the IR chapter, and so that would look something like this. We can move electrons this way onto oxygen. We're moving onto oxygen. We're moving in that direction because oxygen's more electronegative than the carbon that's at the other end. So that's why we're doing that this way. And this is going to be important when we get into 51C. We talk about carbonyl chemistry. We also know about allylic carbocations. Those are resonance stabilized. Oops, did that wrong. So there's a resonance stable's allylic carbocation. We also know that allylic radicals, which I just mentioned, are also resonance stabilized. Weird looking arrow pushing, but that's exactly what you would get. So you need to be on the lookout for these. You need to be on the lookout for allylic carbocations, allylic radicals, and just remember that you need to draw the resonance structure. And allylic carbonyl's also, although we're going to move electrons in a different direction here. All right, so when it turns out that these conjugated systems are more stable than non-conjugated, as we've talked about already, when P-orbal's overlapped, the electron density in each of the pi bonds is spread over a larger volume, this lowers the energy and stabilizes the molecule. So if you look at what this one looks like, these two resonance structures here, if we had to draw all the P-orbitals, this is what they look like. In order for this molecule to be conjugated, those P-orbitals all have to be adjacent to each other, parallel to each other. If they're not parallel to each other, then they can't overlap properly. So this is what it would look like. So they're all straight up and down parallel. If you tilt one like this, you're not going to get conjugation. And we can say the same thing for all of these. Let's jump over to this last one here. And that's going to change things a little bit, the way that we learn things. Let's draw the hybrid for this last one. Where? Oh yeah, I'm missing that. So that in there. Yeah. Okay, so the hybrid, right, we know how to draw hybrids. It turns out that this is what it looks like. We have overlap all the way across. We have partial negative charge on the left, partial negative charge on the right. That would be our hybrid. All right, so now we're going to tell you that we lied to you in chapter one a little bit. We told you a little falsehood in chapter one. All right, so let's look at this. If you were in chapter one, what would the hybridization of this carbon be? What? SP3, but now look at that resonance structure right there. What's the hybridization of that carbon now in that resonance structure? SP2, and so that's not SP3. It's SP2. So all of the atoms across here are SP2 hybridized. They all have to be SP2 hybridized in order for these electrons to overlap. And they all have to be parallel to each other in order for those electrons to overlap. So this is going to look like this. Overlap all the way across just like that. If something was going on in this molecule and this carbon right here, what's going to happen is this is going to become SP2 hybridized. And if this was in a position where this p orbital was not parallel with those, then they wouldn't be conjugated. Have to be parallel to be conjugated. All right, so when the p orbitals overlap, the electron density of each of the pi bonds is spread over a larger volume to a delocalized non-bodied electrons. Or electrons in pi bonds, there must be p orbitals that can overlap, and that means that they're going to have to be parallel. This also means that the hybridization of an atom is different than what would have been predicted using the rules outlined in chapter 1 as we just demonstrated. Conjugated systems must be planar to allow overlap of p orbitals. All right, so here we have, this is benzene, and we have three different drawings of benzene here. This is the p orbitals. Notice they're all parallel to each other. So we get overlap on the top, we get overlap on the bottom, and it looks like this. So definitely all of those, that's all those double bonds there are conjugated. And so the ring is planar. This allows for continuous overlap of adjacent p orbitals. Right, so now if we make this ring two carbons larger, so this is a six-membered ring, this is an eight-membered ring, it seems like this would be the same as that, right? But the problem is when you get to these larger rings, the bond angles change, and this molecule here is not planar. And so what that means is that these double bonds are not conjugated in this ring. There is no conjugation with these double bonds. These are all conjugated, this is not. And that's because the p orbitals can't be parallel to each other. So we've drawn in two of them. So here's the, on the bottom here, that would be, there's a double bond there, so there's overlap here. And then we moved over to this double bond, so that would be there. And notice they're perpendicular. There's no sideways overlap, those double bonds are not conjugated. So each double bond is what we call isolated. So this adopts a tub shape, tub shaped ring, to minimize ring strain. Here for the double bonds are not conjugated. So we would actually call them isolated double bonds. What did I do here? Okay, go a little nuts here. Conjugate it, I can spell conjugated. Therefore double bonds are not conjugated. Now kind of difficult to picture ring strain here. I have these atoms, I have these molecular models in my office, and you're welcome to come by and take a look at them. And if I remember, if I remember if somebody reminds me I'll bring them on Monday. We have two more minutes, so let's talk about relative stabilities of conjugated dienes. Little bit. All right, so we would call these two double bonds, they're not conjugated. So we would call them isolated. These double bonds are conjugated. Remember we alternate double, single, double, single for conjugation. These are conjugated. We know it's more stable when they're conjugated because of resonance, but how much more stable? So one of the ways we can figure this out is we can hydrogenate with a catalyst. And both go to the same compound. So just like we did with alkenes, if they both go to the same compound, both of the products have the same stability, then that means it allows us to estimate. So we have delta H0 for the isolated is minus 61 kcal per mole, for the conjugated it's minus 54, and so what that means is that we have increasing energy going this way. This is the energy of the alkene, alkyne, and then the isolated is here, it releases 61 kcal per mole. The conjugated only releases 54, so that means it has to start off at a lower energy. Here's 54 kcal per mole. So it's lower in energy than the isolated diene because it releases less energy when hydrogenated. We'll stop right there and we will continue this on Wednesday.
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This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: 00:57 - Radical Substitution of Benzylic and Allylic Hydrogens 05:05 - Stereochemistry of Radical Reactions 13:10 - Radical Addition of HBr to an Alkene 24:57 - Radical Initiators 26:12 - The Peroxide Effect 30:06 - Autooxidation 37:46 - Preventing Autooxidation: Addition of Antioxidants (Free-Radical Scavengers) 39:20 - Conjugation
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10.5446/21618 (DOI)
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Good afternoon. We're going to get started. All right. We should, let's quiet down. We should finish Chapter 17 today. And maybe start Chapter 18. The sooner we can start it, the better. All right, you guys, we need to quiet down. We don't want to be lecturing up until the 11th hour on Friday, right? Considering our final is on Monday. Okay. Okay, it turns out that if we look for the molecular orbital picture of benzene, we can explain its special stability. So we drew the molecular orbitals for benzene using frost circle. And frost circle is just an easy way to draw molecular orbitals for cyclic compounds. And so we put the ring here with one of its vertices and add each juncture. We have molecular orbitals at the halfway point here. We have the p orbitals before they combine to make the pi molecular orbitals. And if we have a filled bonding shell, it's especially stable. Does that mean that every time we want to figure out if something's aromatic or not, we have to draw them like an orbital's no? And we can actually use Huckel's rule, which is a little bit of a shorthand way of dealing with this. So Huckel's rule states any conjugated monocyclic polyene. So that is planar and has 4n plus 2pi electrons with n equals 0, 1, 2, et cetera. We'll exhibit the special stability associated with aromaticity. We're going to run through a bunch of examples so you see what I'm talking about here. Systems with 4n pi electrons are anti-aromatic. So they're less stable than their open chain counterpart. So we were right that the ring had something to do with it, but there's some complications here because we have to have a ring, it has to be conjugated, and it has to be planar. So those things are all going to come into play. So to be aromatic a compound must satisfy all four rules, and we're just going to go through all four rules here. Structure must be cyclic, that's the first rule we'll look for. Second, each atom in the ring must have an unhybridized p orbital. So in other words, we have to have either sp3 or sp2 or sp hybridization. We have to have unhybridized p orbitals. The structure must be planar to allow for continuous overlap of parallel p orbitals. That's the tricky part sometimes with some of these rings. And the localization of the pi electrons over the ring must result in lowering of electron energy. So if you have 4n plus 2 pi electrons, it's aromatic and we have special stability. Over and above anything we could have for a normal compound that's aromatic. If we have something that's anti-aromatic, it would have 4n pi electrons, and that would be extreme instability. Okay, so those are the two things, and then everything else is neither aromatic or anti-aromatic. It just has normal stability. So we're going to go through each of these rules one at a time. If it satisfies a rule, we move on to the next one. If it doesn't satisfy a rule, then we stop. And it's neither aromatic or anti-aromatic. To decide whether something is aromatic or anti-aromatic, we have to go through all of the previous rules. So let's go take a look at the previous examples again now that we have this new understanding of what accounts for aromaticity. So cyclobutadiene, what's our first rule? Structure must be cyclic. Okay, all of these are cyclic, so let's put a little one here for rule one. All of these, we'll do them all at the same time for that. All of them are cyclic. Rule number two each atom in the ring must have an unhybridized p orbital. Alright, so for cyclobutadiene, if an atom is part of a double bond, then that means it has an unhybridized p orbital. Okay, here, so these guys, sp2, sp2, every single carbon, sp2, sp2, sp2, every single carbon. So they all satisfy rule number two, which means we get to move on to rule number three. Rule number three, structure must be planar to allow for continuous overlap of parallel p orbitals. And sometimes this can be difficult to decide, and what I'll tell you here is our rule of thumb for this class is if all of the atoms in the ring are sp2 hybridized, and you have a six-membered ring or below or lower, it's planar. It's only when you get to larger rings that atoms can bend out of planarity when they're sp2 hybridized. So that's going to make it a little easier for us. Alright, so number three is the, is it planar? So this is a four-membered ring where all the atoms are sp2 hybridized, so it is definitely planar. That means we count electrons. There's two electrons per pi bond. So there's four pi electrons, which satisfies the rule of four n pi, where n equals one. And so this is one of the anti-aromatic, so this is extremely unstable. So this is the one we had to trap in frozen argon. And anti-aromatic. Okay, so we know benzene is aromatic, but let's see as we go through whether it satisfies the rules. So the third rule was, is it planar? If all atoms in the ring are sp2 hybridized and it's a six-membered ring or below, it is planar. So this satisfies rule number three. And then we count electrons. There's two for every pi bond, so we have six pi electrons. And that satisfies four n plus two pi electrons, where n equals one. And so therefore this is aromatic. Questions so far. Yeah? Is n whatever you need to equal? Whatever you need to, yes, exactly. n is whatever you need it to equal. So if you have an even number of electrons, it's going to satisfy one of these two equations, always. Okay, so even number of electrons, it'll either be four n pi or four n plus two pi. So it's whatever one it satisfies. Alright. How about cycloctotetraene? Is it planar? We talked about this at the very first page of chapter 16, is cycloctotetraene planar? No, it's not planar. Not planar. Therefore, it's neither aromatic nor anti-aromatic. Remember, we need to satisfy all four rules. I mean, we need to satisfy one, two, and three and then we count electrons. If we don't satisfy any of the one, two, or three, then it's neither aromatic or anti-aromatic. So this one, this is like a typical polyene. Normal reactivity of a typical polyene. Alright, cyclodecopentane. Is it planar? Well gosh, the way it's drawn at Sherlock's planar, is it really planar? Here's how you know that this is not planar. Draw the hydrogens in on these carbons here and you'll see a little problem. I can't even draw them. They're right on top of each other. I can't even draw them. So this ring, when you get to larger rings, we can kind of bend out a planarity to account for problems like that. This cannot possibly be planar because those hydrogens will be right directly on top of each other. So this is also not planar. It has the magic number, 4M plus 2 pi, that's the aromatic magic number. And if it was planar, it would be aromatic, but it is not planar. So it is neither aromatic nor anti-aromatic. Again, typical polyene. So the question always comes up, how are we supposed to decide on an exam whether these things are planar or not? And the answer to that is that I will stick with 6-membered ring and below, typically, so that you'll know. Because otherwise, it might not be obvious at all what's going on here. All right, 18-annually, this we know has special stability. And you can see that, and so it's certainly in a ring. Certainly number two, all atoms are sp2 hybridized. Three might not know because it's a large ring. It is planar. And if we draw the hydrogens in here, we can see that there's actually room for them. Not like in the previous example. There's definitely room for these hydrogens here. So this is planar. If we count up the electrons, we have 18 electrons. And how do you know whether it's satisficed? Is it a multiple of 4? 18 is not a multiple of 4, so it's going to satisfy the 4n plus 2pi, where n equals 4. Therefore, it is aromatic. So now everything on that previous slide that we were scratching our heads on is explained here. Questions? Anybody? All right. Ionic cyclic polyenes can also be aromatic, so there's other ring types that we need to consider. Let's go through this. We're going to follow the same steps here. Step one for each of these. Is it in a ring? Yes it is. Yes it is. Yes it is. Yes it is. That's the easiest one. Okay. Number two, are all atoms in the ring sp2 hybridized? How about for this first one? No. Stop here. Okay. No. So you stop here. It's a normal polyene. It's not aromatic. It is not anti-aromatic. All right. Now let's look again at the second one. Are all atoms in the ring sp2 hybridized? If I asked you that question in chapter one you would say no, but after we did chapter 16 we realized that if this is resonance stabilized, and I'm just going to draw one resonance structure, there are many, but if this is resonance stabilized, notice once we draw the resonance structure here. That we started off with something that in chapter one we would have expected this carbon to be sp3 hybridized. Now we move this over to this resonance structure. We see now there's a double bond there, so it can't be sp3 hybridized. It has to be sp2. So the answer to this one is yes, all atoms are sp2 hybridized. All atoms have an unhybridized p orbital. So what that means is, what that really means, and let's scroll down and then we'll scroll back up again, is this is what it looks like right here. If it wasn't resonance stabilized this would be sp3. So in order to become resonance stabilized there's a rehybridization that has to take place here, where that carbon starts off as sp3 but ends up as sp2. And when it goes from sp3 to sp2 it takes that lone pair and puts it in a p orbital. That p orbital notice is parallel to all of these so we can get overlap all the way around. So this one, it gets a lot back from that little maneuver here. So we can now we overlap all the way around here, top and bottom are overlapping here. Having fun with that pen there, yeah, just like that. Okay, so that's what happens there. So let's keep, let's go back and so we pass rule number three. Oh, we didn't pass rule number three. We passed rule number two. What happens in rule number three is it planar. And what's our rule? If it's, if all atoms are sp2 hybridized and it's six-membered ring or below it's planar. So yes, a check for number three, then we count electrons. So we have two per pi bond and that lone pair is going into a p orbital so we count six all together. Six is our magic number. So this is a six pi electrons that satisfies four n plus two pi. Therefore it's aromatic. Therefore it has special stability. Now don't get me wrong this five-membered ring, it's an anion, it's not as stable as benzene but it's especially stable for an anion. Especially stable for an anion. Question so far. Alright, what about this next one here? Are all atoms in the ring sp2 hybridized? Yeah, carbocation is sp2 hybridized so it has an empty p orbital. Is it planar? Yeah, it sure is. We've got our, so we've got, let's redo our one, two, three here. It is definitely planar because it's a six-membered ring or below. So then we count electrons. Two per double bond for pi electrons, okay that's not a good one. That's a four n pi electrons where n equals one. Therefore this is anti aromatic. Therefore extremely unstable. Made at low temperature, trapped in frozen argon, it's one of those, okay. So extremely unstable anti aromatic. Here we have a seven membered ring so now it's going to start to get tricky whether we decide whether something's aromatic or, I mean whether it's planar or not. But what I'll tell you for this one here is that all atoms certainly are sp2 hybridized. This is planar and if we count electrons, we have six pi electrons, six is a magic number, that is four n plus two pi electrons where n equals one, therefore this is aromatic. It is not as stable as benzene but is really stable carbocation. Okay so very unusually stable carbocation. Alright and what I want to do is I want to take the two middle ones here. You know even going through by checking the rules you can also do the frost circle and draw the molecular urgals. Let's take a look at these two here and let's do frost circle on the next page. Just to show you that's really what's going on here as we're checking these rules as a short head way of doing the frost circle. So frost circle, we draw the ring with the vertices down so that's what I've done here. The halfway point, the halfway point is actually a little bit above here. It doesn't go straight through, it doesn't go through these bonds here, it goes a little bit above. And so what we're doing here is we're combining five p atomic orbitals and when we do that we get five molecular orbitals. The number has to stay the same. So there's one, two, three, four, five. So there's one on either side on the top here. Above this line is anti-bonding. Below this line is bonding. And what we want for aromaticity is a filled bonding shell. Yes? How do we decide that there's only two anti-bonding? Should there be bonding or whether there's anti-bonding? Not when there's an odd number like this. There's no way to do that, right? And that's getting really hardcore P cam outside the scope of this class. So we'd combine the five p atomic orbitals, we get five molecular orbitals. How many electrons do we have for this one? We have four, right? Let's fill up our molecular orbitals. One, two, lowest energy first, pair of the spin, degenerate orbitals. We fill one each. Do we have a filled bonding shell? Unfilled bonding shell. It's going to be anti-aromatic. All right. If we go down here, we have the same thing. Everything's exactly the same. We're combining five p atomic orbitals. And we're only looking at the pi molecular orbitals. We're not looking at sigma. We get five. We have two, four, six electrons. Lowest energy first, pair of the spins. Degenerate orbitals get one each and then we start to fill up. That's one, two, this is three, this is four. And then we go back and fill five and six filled bonding shell. Especially stable. So pretty amazing that Huckle came up with this, I think. All right. We can also extend this to heterocycles. So a heterocycle is, a heteroatom is the anti-atom that's not carbon or hydrogen. And so like things like oxygen, nitrogen, sulfur, there's a bunch of different ones. You can also have boron. There's boracycles. And we can also extend this to heterocycles. So let's look at that on the next page. I'm sure which of the following heterocycles are aromatic. All right. So we, you already should recognize this first one. This is pyridine, right? We use that a lot in chapter nine. This is feran. You, you, we've heard of THF, tetrahydroferan. So if we hydrogenate this double bond and this double bond, that would add four hydrogens, tetrahydroferan. So that's where that comes from. And so let's see if these guys are aromatic. So we're going to do the same, we're going to do the same steps. Step one, is everything in a ring? Yes, yes, and yes. Step two, is every atom sp2 hybridized, certainly for pyridine it is. Feran and pearl, well, I mean, think about it. If we want to draw resonance structures for this, which we do, if we look at that oxygen right now, that oxygen right now is part of a double bond, so it has to be sp2 hybridized, right? So definitely all atoms are sp2 hybridized. And likewise with pearl, it wants to do the same thing. So with our new found knowledge from chapter 16, we would, we would absolutely say that that nitrogen and that oxygen are sp2 hybridized. Alright, so we've determined that all of the, we've determined that all of these are sp2 hybridized, they all have rings. They're six numbered ring and below, so automatically boom, boom, boom. Okay? That's, number three is, is it planar? Yes, they are all planar. Okay, and so here's what's happening here. When we do this, when we drew these resonance structures, I'll scroll down and I'll scroll back up again. Here would be the oxygen. After chapter one, we would expect sp3, but then we realize when we get to chapter 16, it can't be sp3 if it's resonance stabilized. So what that oxygen does is it puts one lone pair in a p orbital and it becomes sp2 hybridized. And, and pearl does the same thing. Before the hybridization, it's sp3, but it really greatly benefits from that resonance stabilization. It also is going to enable these compounds to be aromatic. So, so that's a good, that's a good payoff. And so once that happens, now we have this lone pair overlapping there, just like that. Here is, here is pyridine. The lone pair is not part of that aromatic pie system. It's actually perpendicular. This isn't an sp2 orbital. It does not contribute to aromaticity. So we kind of have to know where the lone pairs are. So as, as you can see for furan, one lone pair is, is part of the, the ring and one lone pair is not. Okay, so this does not contribute to the delocalized electrons in the ring. And this is important when we're starting to, when we're doing this next step, which is counting electrons, number four for all of these. So for, for, for furan that has two lone pairs, we're only going to count one of the lone pairs for this aromatic ring here. So this is turning out to be aromatic because it's going to be six pi electrons. And likewise here, this lone pair here is going to kick in to make six pi electrons so that's aromatic. For nitrogen, we certainly don't count that lone pair because it can't contribute to this ring system here because it's perpendicular and neither can that. So that, what that means is that for, for furan we're only counting one of the lone pairs. So let's count electrons for puridine. We don't count the lone pair at all. It's not involved. So this is six pi electrons. Therefore aromatic. Furan, we're only counting one lone pair. So this would also be six pi electrons. Therefore aromatic. For parole again, two, four, six, six pi electrons. Therefore aromatic. Questions. So I think the heterocycles are the most tricky. But of course, most of you are bio-rangers and, and heterocycles play predominant. I pray, play a big part in the body, don't think. So that's, we need to know what's going on here with these guys. All right. Some chemical consequences of aromaticity. Yes. Puridine? Yeah. Go ahead and throw that in there. You guys want me to draw that? I love doing that with this pen. This is fun. Let's do that. Yeah. How about that? Okay. All right. Chemical consequences of aromaticity. Some compounds are, some compounds are unusually acidic because their conjugate bases are aromatic. Other compounds are much less acidic than expected because deprotonation disrupts aromaticity. Also, if you're going to remove a proton and it's going to make the compound anti-aromatic, it's, that's going to be much, much, much less acidic than normal. All right. So some things to consider. All right. So let's compare this guy here, pKa of those protons versus a similar system, removing one of these protons. Notice the difference in pKa. pKa is 15 here, over here. pKa, 45. So we're not just talking 30 times more acidic. We're talking 10 to the 30th times more acidic. That would be a really hard thing to explain before we cover Chapter 17. And so let's look at the conjugate base. It's always a good idea when we're comparing acidities. Look at the conjugate base. Here's our conjugate base and you'll recognize that molecule from the previous page. This is resonance stabilized, resonance stabilized, plus aromatic. So that conjugate base is much, much, much more stable than you would typically expect because of the aromaticity. And that's why it's 10 to the 30th times more acidic. Over here, we just have resonance stabilization. There's no aromaticity. All right. So very surprising result. Heterocycles of interesting acid-based properties based on the aromaticity of their conjugate acids and bases per roll is much less basic than pyridine. All right. So let's look here. Let's draw in here. So when we're talking about basicity, we're talking about how willing is this nitrogen to donate its electrons? How willing is pyridine to donate its electrons? We know pyridine donates electrons. We saw it over and over again in Chapter 9. But how about per roll? Is that going to want to donate its electrons? What do you think? If it donates its electrons, it's no longer aromatic. So it's not going to want to do that. So pKa conjugate acid is minus 3.8. And pKa of the conjugate acid is about 5. So that means that this is a much stronger base. And so the reason is that the lone pair is part of the aromatic pi system. So you lose aromaticity when nitrogen is protonated. For pyridine, that lone pair in an SP2 orbital is perpendicular to the aromatic pi system. So it's not involved at all, no effect at all once that's protonated. The lone pair is not part of the aromatic pi system. It is still aromatic after it's protonated. Alright, so that helps us. Knowing about aromaticity is going to help us make good decisions about what compounds like this will do. We will come back to this in Chapter 25 in 51c. So maybe flag this to come back and look at this right before we study Chapter 25. Alright, another really interesting compound is this compound here. It's a cyclohebdotriene albromide. And it's actually ionic. This is an ionic compound. The way we have it drawn it doesn't look like that. It's actually ionic. And so the structure of this is, it's really cool because what we have here is this seven-membered ring. And we saw on the previous page that this is aromatic. And then there's the counter ion is bromide ion. So, so much power and aromaticity that this compound, that bond, those electrons are transferred completely to the bromine so that this compound can be ionic. So this is aromatic. It's, I actually got a special name. It's called a tropillium ion. Don't need to know that. But it sounds cool. And I believe this is a really deep, deep, deep blue color. And so the payoff here is, is not aromatic in its covalent form. So some really cool, interesting things on acid-based chemistry based on aromaticity. We are going to skip this challenge question. Okay? We might do it at the review. We might do it next week. But I'm trying to buy as much time as I can right now for Chapter 18. So I'm going to slide right past that. Very briefly we're going to talk about nomenclature. So since there's no writing on this page, well, I guess hopefully we had enough time to write that. There's some aromatic rings that you need to know the name of the ring, what we use as a parent. So if a benzene ring has a methyl attached to its toluene, if it has a nitro group attached to its nitrobenzene, pretty straightforward here. If it has an OCH3 attached to its anisol, if it has an NH2 attached to its aniline, if it has an OH attached to its phenol, this is styrene. We saw this way back in the spectroscopy chapter. This is benzaldehyde, this is benzoic acid, and this is benzonitrile. And these are ones you just need to know the name of them. Okay? Because we're actually going to use the names in nomenclature. We talked about orthometa and para when we did Chapter 16, but I'll remind you O for ortho means there's a 1-2 relationship. This is if there's two substituents on the benzene ring. Para is this is we can use P for short. There's a 1-4 relationship between the two substituents. And meta, there is a 1-3 relationship. And that is meta. Alright so if we numbered starting from phenol, we do because that's the parent. 1, 2, 3, 4, 5, 6. We can use numbers or we can use orthometa and para. So this would be ortho position, this would be meta, and this would be para. If one of the substituents can be incorporated in the name the name is used as a parent and that incorporated substituent is given the one position, if the benzene ring has two or more substituents, the substituents are numbered. That's more than two. If there's two you can use ortho and para. If there's three groups on the benzene ring, you don't use ortho and para. You only use ortho and para when there's two. Just kind of like cis and trans. We only use that if there's, we're talking about two R groups. So this one for example here O, ortho, bromo, phenol. Or you can write it as two bromo, phenol. Both of those are acceptable names for that compound. The second one here has three substituents so we can't use ortho or para. This would be two, three, dichloroanilin. Not orthometa dichloroanilin. Okay, so let's put a big X through that. That's as much as we're going to get into nomenclature of benzene rings. Okay. Alright, so I'm going to save that and we're going to start chapter 18 today which I'm thrilled about. And now this is a good time to ask questions while we're saving that. Anybody? Alright. It's a beautiful thing we're on the last chapter guys. It's exciting, huh? You're almost two thirds of the way down with O. Chem. Was there a question? There. Oh, right there. Yeah, so yeah, so his question is about if you have larger rings, they usually will try to bend out of planarity if they're going to be anti-aromatic. We don't see too many anti-aromatic large rings because they usually can bend away so that all the things, so they're not planar. So a ring is not going to become, if it has a choice of being planar or not planar, it's not going to be planar to be anti-aromatic. It will avoid anti-aromaticity at all costs because remember all molecules are trying to get more stable. Are we all trying to get more stable? It's pretty true, right? Okay. So we are absolutely blown away by the stability of aromatic compounds. We think up to now that they don't do anything. They do. There's a lot of reactions that they do and that's important because a lot of drugs contain aromatic rings. A lot of important natural products contain aromatic rings. So we need to be able to do chemistry. So they do chemistry. It's just a different chemistry. So here are the reactions we're going to talk about in this chapter, in this order. So what does benzene do? Basically the most characteristic reaction is electrophilic aromatic substitution. You could also do nucleophilic aromatic substitution. We're going to talk about that next week. That's a new part of this fourth edition. I will give you plenty of problems to cover that if you don't have the fourth edition. It's not a big deal. But the most characteristic reaction is for the benzene ring to act as a nucleophile. That would be electrophilic aromatic substitution. Why do I keep doing the same thing? Okay. These guys are the electrophiles. So our generic electrophile E plus. So what happens when we do bromine and FEBR3? That is a bromination. So we're using the same word but we're not getting the same product that we got from chapter 10. Okay. There's nitration. So we're going to be able to do nitration. We're going to do sulfonation. So this is something pretty new. We're also going to do fritocrafts alkylation and fritocrafts isolation. There's fritocrafts alkylation and then we have fritocrafts isolation. So we have out of a possible, let's see, how many do we have here? Five. One of these mechanisms will be on the final. They're very similar. The only thing that's different is when we make the electrophile. After we make the electrophile, the rest of the reaction is the same. So it's really not going to be that bad. So guaranteed to have one of these guys on the final mechanism. Alright. Let's do a little review here. Chlorination and bromination of benzene in chapter 10. Alright. So we made the 1, 2 di-bromocompound, didn't we? We remember that. And that was electrophilic addition via a bramonium ion. So we made the 1, 2 di-bromocompound. If you have no idea what a bramonium ion is, you crammed everything the day before midterm too. And it's all gone. Okay. So that's chapter 10. Now do we do the same thing with benzene? No. Why not? You'll tell me why. No. Electrophilic addition. Why don't we get electrophilic addition? It makes it's, the aromaticity is gone. It's not anti-aromatic, it's just not aromatic. Aromaticity is gone if we did that reaction. There's no reason for that reaction to happen. It's an uphill reaction. And so what we do instead is electrophilic aromatic substitution. So they share one word in common. That's the only thing that's the same. That's better. That's a much better product because we're still aromatic. Our side product which we never worry about except for the first time we do a reaction is HBVR. And this is electrophilic aromatic substitution, not electrophilic addition. Alright. So we're going to do the mechanism. We're going to do the mechanism for all the reactions on the front page that we just had. And then we're going to talk about some, wow, there's a lot more to this reaction than that. You mean these reactions than that. So for the mechanism here the first step is to make the electrophiles. So bromine on its own is not electrophilic enough so we have to kind of soup it up to make it more electrophilic. Why do we have to soup it up? Benzene's still stable, right? Why is it going to react if it's not souped up? So we've got to do that. So here's what we're going to do. We add a Lewis acid. Iron would like to very much like to have 8 electrons in its valence shell. So it's a nice Lewis acid. So we'd get a Lewis acid based reaction. There will be a negative charge on iron. There will be a positive charge on bromine. And what that does for us is it polarizes this bond. Okay. It really polarizes this bond. So it makes it more electrophilic when we do that. So it polarizes this bond. It makes it more electrophilic. Alright. In the second step, benzene attacks the electrophile to make a resonance stabilized carbocation. This will be the same for all of the five reactions on the previous page. This will be the same. The third step, the third part of the phase of the reaction will be the same. So the only difference is going to be this part. So it's really not as much as you think it is. So let's draw this guy. Alright. So this is going to come and it's going to attack the bromine. We're going to break the bromine-bromine bond. This is the slow retetermining step. We are breaking aromaticity and making a carbocation. So it makes absolutely good sense that this is the rate-determining step. So just like electrophilic additions from chapter 10, one side gets the positive charge and one side gets the bromine. And when I put the bromine on, I usually put a hydrogen on that carbon to show so I don't accidentally make bad resonance structures. Okay. So we're going to draw, we can draw three resonance structures here. So we're doing terrible things. We're breaking aromaticity, we're making a carbocation, but it's not as bad as it could be because we do have a resonance stabilized carbocation here. So that's helping. So three nice resonance structures, resonance stabilized carbocation. And in the last step, we're going to regenerate the aromatic ring by using and doing an E1 reaction. We'll do that next time. I hope you guys have a great weekend. Try to figure out what that's going to be yourself.
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This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: 00:47 - Molecular Orbital Picture for Benzene 28:23 - Some Chemical Consequences of Aromaticity 36:26 - Nomenclature 40:26 - Electrophilic Aromatic Substitution 44:09 - Chlorination & Bromination Benzene
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10.5446/21620 (DOI)
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Good afternoon. Let's quiet down so we can get started. I'm a little late today because I came right from discussion. Are there any questions before we get started? Anybody? All right. We're going to work on Chapter 18. It appears that we are going to have to skip the nucleophilic aromatic substitution reaction part of this chapter. I will cover it next quarter when we do Chapter 25 if you have my class next quarter, but we're not going to have time to cover it. So I'll let you know when we get to that section. Where did we leave off last time? We were drawing a bunch of resonance structures. We were trying to prove, we were trying to see why electron donated groups give ortho and para products. So we did the ortho and what we saw is that we can make a really nice resonance structure here. This one is especially stable. What did you just do? Okay. Doesn't want to do that for some reason. We'll just continue it right here. Especially stable resonance structure. Why is it especially stable? Every atom has eight electrons. Every atom has an octet and we have an extra covalent bond. So especially stable, all atoms have octet. Plus we have an extra covalent bond. So we saw as we were doing electrophilic aromatic substitution on benzene, we have three resonance structures. When we have an electron donating group, we have four resonance structures. Okay. So that's going to make things especially stable. That's going to mean that we have a lower energy pathway here. Since the first step is endothermic, it means the transition state is going to be more stable. The carbocation is more stable. That means the transition state by Hammond's Proficulate will also be more stable. Okay. So that gives us, that's the ortho. And what we're going to see is the same thing is going to happen with the para. And then we're going to go here. And then we're going to get an extra resonance structure. I'll just draw it this way. I could have drawn this as my third structure, but I'm just going to do it right now. That looks like this. And you can see that once again, we have this extra resonance structure that's especially stable. That one here and this up top here. So let's circle that. That has, we have a lone pair on oxygen. We have a positive charge. And there's our especially stable resonance structure. So the ortho and para always go together. And you can see that we're going to get a fourth resonance structure that's especially stable. If the group goes on in the meta position, there's only the normal three that we usually draw. So it will look like this. And then we can go here. And that will look like this. See, I did that right. So we go here, then we go here, positive charge right here, and the nitro group here. So we don't have any especially stable. We don't have any especially unstable. We just don't have that fourth bonus very stable resonance structure. And that's why we don't get any meta attack when we have activating groups. So in the ortho and para case, we'll write this down below. In the ortho and para case, the extra resonance structure lowers the energy of the carbocation intermediate intermediate and by Hammond's postulate. The transition state. The transition state leading to this intermediate. That's a lower energy pathway since this is a very, this is a high energy of activation for that first step. It makes sense that the ortho and para pathways are going to be better. I also want you, so we're going to have one of these mechanisms on the test. I usually have one where there's substitution already on the ring. So just to give you a little heads up on that. But what you want to make sure that you do is you check when you're doing resonance structures because you'll get two points per resonance structure that you don't duplicate that you don't draw extra. So what you want to look for is here's the incoming electrophile. The positive charge when it's in the ring is either is going to be in both ortho positions. Here ortho to the nitro on the left, ortho to the nitro on the right and para to the nitro. That will always be the case. So up here, here's our incoming electrophile. Ortho on one side, ortho on the other side and para. So do a double check after you draw your resonance structures to make sure that you haven't made any mistakes because if you draw extra resonance structures that are incorrect, they cancel out ones that are correct. Okay? So keep that in mind. So that's rule one. Ring activating substituents or ortho-para directing. Alright, so now let's look at rule number two. This is for deactivating. And then we're going to talk about a third category and that would be the halogens. So now notice that since I already have the skeletons for the resonance structures drawn here, notice that we don't have extra resonance structures for any of them. We have three for every one. And this time I'm just going to use generic electrophile here. So I'm going to do, I'm going to put the electrophile here. That's ortho attack. And then I'm going to do meta using that same double bond. Now I'm putting it in the meta position. And here I'm going to have to use this double bond on the bottom to attack the electrophile. And that will put the electrophile in the para position. So look like that. And then let's throw in on the rest of the double bonds here. Positive charge will be right here. And then we're just going to go crazy drawing resonance structures here. So I can move this over here. I can also go over here on this side, making sure not to duplicate. Does anybody see a problem with that third resonance structure I just drew? We've got two positive charges right next to each other, right? Two positive charges on adjacent carbons. Very unstable. So we drew three resonance structures, but one of them is particularly unstable. So we'll circle that bad one here. And ortho and para always go together. So what that means is that we're going to have one, when we attack in the para position, we'll have that same thing. And we're going to get that right away here. That's going to go right here. There's our especially unstable one right here in the middle. So here and here. And then in the last one here we'll just have the double bond go and the other ortho position here. So it'll look like this. So when we have ring deactivating substituents to electrophilic aromatic substitution, the best one, I didn't finish the meta. Let me finish the meta. The best one is the meta. It's not especially stable, but it is also, let me fix that. No, that one. Gosh darn it. So we're going to go here. So we'll have the positive charge here, double bond here. We have it in one ortho position. Let's put it in the other ortho position. So we don't have any especially stable, but we also don't have any that are, we have two that are especially unstable. Do you have a question over here? On adjacent, yeah, atoms. Let's change that to atoms. Thank you. I appreciate that. On adjacent atoms. We'll just, on adjacent atoms. Yeah. Okay. So in this case, the meta tag is better because we have three D's and they're okay, but they're not great, but we don't have this especially bad one that we have in the ortho and para. So meta attack. No, especially unstable. Resonant structures. So that's going to be our lowest energy carbocation. Lowest energy carbocation, then of course the lowest energy transition state. And therefore the lowest energy transition state. Questions on deactivating, deactivated rings. So much more satisfying to actually know the reason why than to just memorize that ring deactivating are meta directing. All right. Hallogens are in their own category. So I think it's easier for students when I put halogens in their own category. So halogens are slightly deactivating, but ortho-para directing. So, and the reason is is that with halogens there's a strong inductive effect. So halogens are strongly electronegative. That deactivates the ring. But they have a weak resonance effects. They can donate their electrons, but they don't really like to donate their electrons very well. Hallogens are not very basic. So they're not inclined to donate their electrons, but they can. So the lone pairs donate electrons back into the ring to stabilize the carbocation intermediate. All right. And so they are slightly deactivated, but they are ortho-para directing. And so I'm going to just show you. I'm not going to draw all of them. We just did that, and you can do that for yourself. But as you can see, we tack with the electrophile here, and we put the electrophile in the ortho position. We do have these lone pairs on bromine. Bromine's not super basic, so this doesn't really help very much, but it does help a little. So we get that extra stable resonance structure here. I haven't drawn all of them. There are three more, I mean two more, plus two more, which you can draw yourself. And we have this extra resonance structure, which is not, we don't get when we're in the meta position. Sorry about that. So extra resonance structure when electrophile is in the ortho and para position. Not true in the meta case. So you should try this on your own. So this, the halogens are kind of half, they've got parts of deactivating, parts of activating. They're activated, they're like activating in that they're ortho-para directing, but they are, they're definitely slightly deactivated. Alright, so those are the three categories. It helps to kind of categorize them in the three categories so you can be able to figure out what your products are going to be. I want to talk about effective sterics in more than one substituent. So with ortho-para directors, para will predominate as substituents and incoming reagents get larger. It makes good sense. So if we do nitrate, if we nitrate toluene versus isopropyl benzene, here we get 58.5% ortho and 37% para. If it's isopropyl, we get 30% ortho and 62.3% para. So as you see we go from 37 para with a methyl to 62.3% para with isopropyl. Now if that becomes a terputal, we're going to get pretty much all para as the terputal group is much larger. This is actually, believe it or not, para is slightly favored here. And that is, and the reason is that methyl is, it does have some sterics involved with it. There is, there are some sterics. How can para be slightly favored here? If there was no favorability, we would have statistically, we have three spots that can go, right? So it could go ortho, para or meta. And if there's three thoughts, one third of the time it should go para and two thirds of the time it should go ortho. So if there was no selectivity, statistically there's twice as many ortho positions. If there was no selectivity, we would get 66.6% ortho and 33.3% para. So as you can see, we do have a little bit more than 33%. So actually it doesn't seem like from the numbers para is slightly favored and that's because methyl, it's not very hindered but it is, has some steric hindrance which would make more go into para position. Questions on those two? So we want to keep that in mind when we're doing substitution on a benzene ring because when we have ortho para directors, we usually get ortho and para and there's really nothing we could do about it but the more bokeh that group is, the more para. When the directing effects of two or more substituents conflict, so let's say we have electron donating and we have electron withdrawing. The one that is strongly activating and ortho para directing determines the orientation of the new substituent. All right, so strong electron donating group, strong electron drawing group. We have a sulfonyl group going on and it turns out that we're going to get ortho and para to the methoxy group. So the two products we will get. So in the battle of the directing groups, methoxy wins by far. All right, so here it is ortho, I mean para to methoxy. Here it is ortho to methoxy. We do have another ortho position. Do you think we're going to get anything there? Right here is our other ortho position and that's pretty hindered there to go in the middle there. So we don't tend to get that product. So you get ortho on the least substituted side para here, but we wouldn't tend to get the one where there's a substituent right there. Now if this was a, if this was a methyl instead of a methoxy, nitro wins. Okay, if this was a methyl instead of a methoxy, the nitro group, things are going to come met it to the nitro group. So when we have strong electron withdrawing and strong donating, if the strong donating wins, if we have strong electron withdrawing and weak donating, electron withdrawing wins. Okay, so that just to keep that in mind. And that leads us to additional considerations regarding substituent effects and this is where it gets more complicated. All right, methoxy, hydroxy and amine substituents are more complicated than they would seem. So if we take hydroxyl and amine substituents are so strongly activating that halogenation is carried out without the Lewis acid catalyst, FEBR3 or FECL3, even without a catalyst multiple halogenation is observed. So if we take phenol and we put it with bromine and no FEBR3, just water as a solvent, instant decolorization. So bromine is kind of like a deep deep red brown red color and when you add it, it's going to instantly decolorize, which means that that reaction is happening very rapidly at room temperature and all three ortho and para positions are filled. To monohalogenate phenol, run the reaction in nonpolar solvents such as carbon tetrachloride without added catalyst. And lower temperature also helps. We'll add lower temperature there. And you get ortho and para. All right, so got to be careful with phenol. The same goes for anisol too, whether you have them in the oxy groups, that's going to be the same as phenol. Amine substituents give multiple halogenation even at low temperature without added catalyst. You cannot stop at one halogen going on the benzene ring. All right, so we have a solution for this to make this reaction to sort of aniline is very highly activated and what we can do is we can turn it into acid aniline and that tones down the reactivity greatly. So this is strongly activated. And what we do to do that, we isolate the amine. So we're going to use acid chloride and pyridine. This is chapter 22 chemistry so you do not need to know the mechanism for this reaction. I'm going to show it to you just so you can kind of picture what's happening. But when you do that, it's now moderately activated. So acid aniline, if you go back and you look at your activating groups, you'll see that this is now moderately activated. And when we brominate, so it's now moderately activated and it's pretty bulky, isn't it? So we're going to get like about 95% para. I'm going to get maybe 5% or if I'm 95% para for this reaction. Okay, so it's 5% or so, 95% para. So I do need to put my bromine there, don't I? So 95% para. So this is sterically hindered. Therefore, mostly para. And now once we're done with that, putting that bromine on, we can take that acyl group right off again. That is chapter 22 chemistry. This is a hydrolysis. That's a hydrolysis. You do not need to know the mechanism. You will know that soon enough when you get back here to start the third quarter of O-chem. And so what that does is gives us aniline. Back again with one bromine on the ring. Okay, and that's important because once those bromines are on there, there's nothing you can do to get them off. So if you just want one bromine, you have to go through this long strategy to do this. I do want to show you how the amine is converted to an amide. It's an additional elimination that's similar to the mechanism for thionyl chloride. Let me show you. You don't need to know this mechanism, but some of you need to see this. It helps you to understand what's going on, and that makes it easier to remember the reaction. Okay, so thionyl chloride mechanism, remember there was a sulfur there. Very similar to this. We did addition. So hopefully this is triggering the memory of that reaction from the first midterm. Alright, and then what happens after that? The electrons on oxygen come down and we kick off chloride. So this is like the tussle chloride mechanism. This is like the thionyl chloride mechanism. We do have a positive charge on the nitrogen, and that's why we have the pyridine to deprotonate that nitrogen. So this is not really anything too difficult, but technically it is material from 51C, so I will not be asking you this mechanism. And then of course the last step. So if you draw this right under the thionyl chloride mechanism, you'll see how similar it is. And in the last step we deprotonate with pyridine. So that's how we isolate. So definitely you want to get it straight in your mind. To isolate the nitrogen, we use acyl chloride and pyridine. To actually put the acyl group on the benzene ring to do Fritocraft's acylation, that's the acyl chloride and what? AlCl3, right? So two different things. With pyridine, so we have the acid chloride here. Acid chloride with pyridine puts it on the nitrogen. Acid chloride with aluminum trichloride puts it on the benzene ring. So definitely want to make sure you get those straight in your head. Alright, questions? Anybody? Lots of problems with aniline. A lot of problems with aniline. That leads us directly into Fritocraft's alkylation and acylation. Lots of problems with Fritocraft's too. We're going to have to keep in mind. Alright. So we'll use ethyl bromide, AlCl3. We're going to put an ethyl group on the benzene ring. Hopefully that is familiar to you by now. Alright, now let's say we start off this reaction by forming one molecule of this and then we have a bunch of this and one molecule of this. Which of these rings is more activated? Once we put that ethyl on, that's more activated. So what that means is the remaining ethyl chloride and aluminum trichloride is more likely to go on to this ring than that ring. Because this is activated, that's not activated. Okay? So what we end up getting, if we're not careful and we don't take steps to avoid this, it's going to keep going. Now we've got two activating groups on the ring. That ring is now more activated than the one ethyl group on there, which is more activated than having no ethyl groups on there. So we're going to get this. We're going to get ortho, we're going to get trisubstituted, and we're going to get tetrasubstituted. Big problems here. Alright, so the whole thing is about, this is an activating group. So therefore the product is more reactive than the starting material. Alright, so how do we avoid this problem? We actually can't avoid this problem by using a large excess of benzene. Solution, use large excess of benzene. Alright, so rather than using a one to one equivalent here, we're going to use an old large excess of this. So maybe a thousand times more than that. So what that means is that, remember when we have the chloride attack the aluminum, we get that activated electrophile, it's more likely to encounter a benzene than it will to encounter one of these guys. Or one of these guys or one of these guys. So that's a way around that. So use a large excess of benzene for Friedelcraft's alkylation if you just want one group going on. So just keep that in mind for the exam coming up. And that's on that. Anybody questions? Do we have that problem with Friedelcraft's acylation? Do we have a problem with more than one acyl group going on? Anybody? No, because it's now deactivated. So product is deactivated. Therefore, over alkylation is not a problem. Or I should say over acylation is not a problem. So we have to worry about it with alkylation. We do not have to worry about it with acylation. Yes? You can write excess just right below it. You can use it as a solvent which means there would be a large, very large excess of benzene. All right. Problem with both Friedelcraft's acylation and alkylation. So we've already encountered one problem. Alkylation goes overboard. You get over alkylation. Problem number two. Deactivated meta-directing benzene derivatives and aniline derivatives give poor yields of Friedelcraft's products and should not be used in this reaction. All right. So that's a big problem. That really limits us. Deactivated. Meta-directors cannot undergo Friedelcraft's, which I'll abbreviate FC, Friedelcraft's reactions. And I mean alkylation and I mean acylation. Well, what about halo-benzene, that third category? Are those okay for Friedelcraft's? What do you think? Well, it says here deactivated meta-directors. Halo-benzene are okay because they're deactivated ortho-paradirectors. Halo-benzene's okay because they are deactivated but ortho-paradirecting. It has to be both. So we want, make sure you look for both of those things. Deactivated meta-directing. So halo-benzene's are okay. Halo-benzene's can do Friedelcraft's and none of these guys can. So why aniline derivatives though? Why? Because that's super activated. Here's the problem. This is an electron donating group, right? If you add al, if you add acyl chloride and alCl3 to that, what is the strongest base that you have there? Nitrogen. Nitrogen's the strongest base. Remember? So here's our, here's our reactivity. CnOF, Cl, V, R, I. In order to do Friedelcraft's, we have to have the chloride attack the alCl3 and come off. Chloride does not have a chance because we've got increasing basicity this way. So the nitrogen is the one that's going to attack the alCl3. And let's look at what happens once the nitrogen attacks the alCl3. What happens to the nitrogen? It, it actually almost looks like this guy, right? Now the nitrogen has a full positive charge on it. That's a strongly deactivated meta-director now. So we've just turned this strongly activating into a strongly deactivated meta-director. So let's label that. This is strongly deactivated. Strongly deactivated. So you deactivated plus a meta-directing. So therefore no Friedelcraft's. Okay, so aniline is, is, is not working really well for us here. But we actually do have a solution for this. The same solution we had for the aniline when it was doing, putting too many bromines on at the same time. Aseleated. So here, let's get this straight here. When we use the acid chloride and the pyridine, the pyridine is going to put this group on nitrogen. When we use the acid chloride and the aluminum trichloride, this group is going to go on the benzene ring. Want to get that straight here. This is going on nitrogen. So this is the one that's like the thionyl chloride reaction. This is the electrophilic aromatic substitution. So what we can do is isolate. Now we can do Friedelcraft's. And, and the reason we can do Friedelcraft's is this nitrogen right here is no, no longer super basic. Let me scroll down so we can compare the two. This nitrogen right, oh don't do it that much. Okay, so this nitrogen right here is super strong base. This nitrogen right here, not a super strong base. Why is that? Much weaker than a super base. Why is that? This lone pair would much rather kick in onto this oxygen here. Okay, so what happens is that this guy is kind of tied up in this resonance here. If that nitrogen takes its lone pairs and puts it on oxygen, the oxygen gets a negative charge and oxygen loves having a negative charge in a resonance structure. So, so, so that nitrogen is not very inclined to attack the ALCl3 when it's got this friendly neighborhood of oxygen right here. It can throw its electrons onto. So this one actually will do Friedelcraft's. So what happens in that next step? Where is this group going? Orthopara mostly. Para, this is pretty bulky. Alright, so now the CH3 is going, A-cell group is going on the benzene ring mostly para. Uprout, 95% para. And now we're ready to take that A-cell group off again. We're just hydrolyzing it. So just remember once that A-cell group's on there, to get it off we hydrolyze. So acid and water followed by base to deprotonate the nitrogen which will be protonated under those conditions. And we've actually found a roundabout way to do exactly what we would like to do. So we kind of have to do this roundabout way here. This on that example, anybody? Alright, and guess what? Aniline has more problems. We're not done with problems with aniline. Alright, problem number three with aniline, nitration. Okay, should work. Why? What's going on here? Why can't that work? Problems. Nitric acid is a strong oxidizing agent. And primary amines are easily oxidized. When you have a powerful oxidizing agent and you mix it with something that is easily oxidized, you can get an explosion and that's where you can get an explosion if you do this reaction. Explosion, if you don't get an explosion, you get tar. And that's where, and you guys probably haven't run a reaction where you get tar, but you run a reaction and you think everything's going to work and you end up getting this tar-like substance in the bottom of your flask that's black and usually means that your reaction has done not what you want it to do and it's something that goes immediately into the waste container most of the time. Alright, so we don't want to do that, it doesn't work. Now, if you have this one here, tertiary amine, that will work very nicely. Where will the nitro group go? So this is not a primary amine, so this is okay. Where is that nitro group going to go? You think para? What's going to happen to that nitrogen as soon as you put it in concentrated nitric acid, concentrated sulfuric acid? What are the fastest reactions of all? Yeah, so what's going to happen is we're going to, we're going to protonate this. Now that's an equilibrium that's going back and forth, so what we end up getting is the major product is actually the meta product. But you also will get the other ones depending on which state you're in here in this equilibrium. Okay, so you're going to get some, you can get some orthopara and you're also going to get some meta here. Alright, so that's, and this should be NH2, sorry, I'll fix that. NO2, yeah. Alright, so that will work, it will not give you exactly what you want because you're going to get some, you're going to get some ortho and para. But if you have acid anilid, it nitrates very nicely. Okay, so I know this works because we do this in my major's lab, major's honors lab. And you get about 95% nitro in the para position. That's your major product. Alright, so if you have a primary amine, if you have aniline and you want to nitrate it, you have to isolate it. So we're going to do the same exact thing that we've been doing here. We're going to isolate this. That tones down the reactivity of that nitrogen immensely because now that lone pair likes to hang out on oxygen in that resonance structure. And then we nitrate and so then our nitro group is going to go on in the para position mostly. So this is going to be the major product. And then we hydrolyze. H3O plus H2O heat. We'll talk about this reaction next quarter and you will know the mechanism for this. It's not that hard of a reaction but you'll get a protonated amine because you're in strong acid. And so that's why in the last step you want to do a basic workup to give you aniline with the nitro group in the para position without any explosions, without tar. So it's just a little bit longer steps but it actually works. It actually gives you what you want. Questions? Anybody? Alright, we'll stop right there and we'll talk about reactions of substituents on benzene next time.
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This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: 00:43 - Ring Activating 07:06 - Ring Deactivating 15:57 - Effect of Sterics and More than One Substituent 21:19 - Methoxy, Hydroxy, and Amine Substituents 29:41 - Friedel-Crafts Alkylation & Acylation 42:19 - Nitration of Aniline Derivatives
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10.5446/21622 (DOI)
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In some elimination reactions, we're talking about most of the time the most stable product predominates. In some elimination reactions, the less stable alkane is the major product. And when that happens is when we have a very hindered base and a very hindered alkyl halide. Your book will tell you that the alkyl halide has to be tertiary and the alkoxide, the base has to be really hindered also. But I think in the lab you're going to be doing an elimination experiment. My students did it last week and I think what students found is that even with a secondary alkyl halide and a hindered base, the major product is the least substituted to do. You looked at it already? Oh yeah, so it's pretty much secondary and tertiary alkyl halides and a very hindered base, so terputoxide qualifies. You get not the most substituted but the least substituted. And it just has to do with the fact that the base has a hard time coming in. Let me show you. I'm prepared with everything except a voice. But the base, this very hindered base has to come in. If it's going to make the most substituted alkene, it has to remove one of these two beta hydrogens. And that's hard for it to do because it's so hindered. So it's much easier for it to grab one of these hydrogens that are on the outside and it turns out that that's the major product you get. For this very hindered base removing one of these and instead of that one in the middle, it's harder to reach. All right, so let's draw the product here. Typically do you get two products but the major one should be, oh I don't want that. All right, so that is trisubstituted product. And then we also get disubstituted product. So that would look like this. So some of you are still at the phase in this chapter where you're even having trouble seeing what the product is going to be or being able to predict it. And so you want to move past that point rather quickly because this other stuff is much more complicated. So CH3 and this would be apple. So this is the most substituted. It's trisubstituted. And this is disubstituted. So we're looking for R groups here. Some of you have a lot of trouble seeing this. Don't feel bad if you do because a lot of people have to feel the same way. I think it's easiest if you draw the hydrogens and it's easier to see R groups when you have the hydrogens actually in. So this would be a geminal disubstituted product and this would be a trisubstituted product. And it turns out that we get 28% and 72%. And it's because the base removes the most accessible hydrogen. And the base and the alkyl halide are very hindered. So like we said, I think as you'll see when you get into lab that this, Smith will tell you that it's only tertiary. But we even with secondary the major product is the least substituted alkene. All right, so compare that with this one here where we take the same substrate. So we still have our tertiary alkyl halide which is very hindered. And but now we're going to use an unhindered base. So a thoxide is a good unhindered base that does really good in the EG reaction. And now we're going to have, we're going to get the same two products. But this time the most substituted is going to be the major. So that's the same first product we got above trisubstituted. And then the second product is the same one we got above. And we do get both, but the major one is going to be the least substituted. So this would be disubstituted. So let's see the actual numbers we get here. 89% and 31%. So they don't, the terminology in the book, oh look it was, I didn't even have to draw those, it's on the next page. I'm going to go fix, I'm going to fix the next chapter so that it doesn't scroll weird like this. So you guys can just add that in yourself. There is a name, your book doesn't use the name, but there is a name for both of these. They use ZYTSEF, so this is ZYTSEF. The least substituted is called the Hoffman product. So the ZYTSEF is the most substituted, the Hoffman is the least. So most substituted and Hoffman is the least substituted. Alright, questions? That's it. All we did was change the base. Yes. Alright, we got one more complication with the E2 and that is the stereochemistry. For an E2 elimination to occur the beta hydrogen and the leaving group must be in the same plane. Okay, beta hydrogen leaving group must be in the same plane. The best is anti-periplanar and this is the only one you will see in this class. Only one you will see in this class. So there's two possibilities. There's anti-periplanar which is the most common. In very rare circumstances you can get synperiplanar and that's with rings and things like that that cannot do anti-periplanar. We will never see in this class if you are a chemistry major you will see examples of this. But if you're not a chemistry major this is all you're going to see. So I don't want you to show synperiplanar. So I'm going to put a big X through this. You won't see in this class. Alright so anti-periplanar, beta hydrogen and the leaving group, I'll just abbreviate LG are in the same plane and anti to each other. And that's where we're going to see synperiplanar is higher energy only under special circumstances in this class. Alright so let's do an example here. So what we see is here and what's going to be really helpful in this chapter and hopefully you remember how to do this is to take three dimensional structures and put them into Newman projections. That will help you greatly in this class and that's something that I want you to know how to do. So if you thought you were done with that you're wrong. Do need to know how to do that. So what we have here is this is the beta hydrogen, here's the leaving group. So we're going to basically put this into a Newman projection. Here's the leaving group. And the beta hydrogen to be removed is on the adjacent carbon. It's not on the same carbon, it's on the adjacent carbon. So here's the beta hydrogen to be removed. And it's drawn nicely like this with the beta hydrogen and the leaving group in the same plane and anti to each other. You don't have to put it into a Newman projection. So you can see here this is our beta hydrogen and here's our leaving group. So easy to pick out the leaving group, not necessarily easy to pick out the beta hydrogen. The carbon bonded to the leaving group is alpha and right next door is the beta. We also have another beta don't we? We have this one here. But we have an unhindered base so I'm not even going to worry about that one. Because I'm going to draw you the major product here. All right, so what's going to happen is I'm going to show it both ways. The thoxide comes in. Oxides going to grab the beta hydrogen. We're going to break the carbon hydrogen bond. And then the leaving group leaves. And so leaving group is leaving, I want to see lone pairs on it. Yeah, so that's going to look like this. Let me just draw it this way. It's a little strange way to draw it, but it works nicely. I'm going to keep the methyl going back. I'm going to keep the phenyl coming forward. And the methyl on the right hand side is going back. And this hydrogen is coming forward. Now we usually don't draw alkenes that way. We usually draw them flat on the page. But in this case, I'm just drawing it tilted so it would be perpendicular to your page. And that's OK to do that. So again, rather than flat on your page, it's just tilted like this. So that's what it would look like. So that's from the dash wedge. If we do it the other way here, we're going to lose that. So this is after loss of HBr. All right, so I'm just going to remove the HBr. I'm going to keep the Newman projection here. But I just want to make a point here. So this methyl here is still here. The spenyl is here. On the back, here's our methyl here. I haven't moved anything on the back. This is the hydrogen. Well, that's a little strange to see it that way. But remember, the carbon-carbon bond, here's the front carbon right here. And this round thing is the back carbon. So that still stays. This is the front carbon, and this round thing is the back carbon. And so as you can see, our alkene is like this. So in order to figure out what that looks like, we're just going to connect the two lines. A little hard to picture, but can you just see that it's going like that? I'm going to redraw it without the circle because it looks a little strange with the circle. So notice, if we draw the double bond in here, right here, the methyls are on the same side of the double bond. So they're on the same side here. I've just kind of rotated it this way. These two structures are equivalent. It's just that one is in the plane of your page, and one is perpendicular. But you can draw that either way on an exam. Questions on how I did that? Anybody? Yes? Oh, we have so much more. Well, you don't want to do the circles a little strange. I just left it there so you could see where things are coming from. You don't want to have the circle there. So I would write it like, let's circle what you can do here. So you can write it like this, or you can write it like this. Don't want to draw it with a circle because that's a little strange. Like, what does that mean? OK. Sin elimination of the same alkylhealy does not occur. Why? Let's draw it on the next page. Of course, you guys have this at the bottom of that same page. We're going to fix this all in chapter 9. I know what this program's about, so I know how to fix it. So all groups are eclipsed here. So what I've done in going from here to here, can I get them on the same page at the same time? No, too bad. Let's see what I've rotated. I kept the front the same and rotated the back. Methylphenylhydrogen, the front is state the same and the back is rotated. That would give you sin elimination. So back is rotated. So number one, the reason we don't get sin elimination is because in order to get sin elimination, all groups have to be eclipsed. And that's disadvantageous. In elimination, all groups have to be eclipsed, and that's disfavorable. That's going to raise the energy of the translation state. And the other thing is that if we have the base here coming in on the same side, if we draw all our lone pairs in, this is what a sin elimination would look like. So not only are all the groups eclipsed, but we've got this nucleophile coming in. This nucleophile is surrounded by, it's got three sets of lone pairs coming in in close vicinity to the leaving group, which has lone pairs. That's not going to favor the reaction. So that's why we don't get sin. And so let me draw the product that we don't get. And again, depending on how you do it, you can draw it like this. Methyl is still going back. Phenyl is still coming forward. Hydrogen going back. Methyl coming forward. That's equivalent to flat. We can draw it flat also. And it turns out that you don't get any of that. So I'm going to put a big X through all that thing I spent time drawing. OK, so is it going to let me do that? Let's try that again. Big X. So two reasons why this doesn't work. Transition state has eclipsed conformation. Those are the things we want to look out for. And right here, as you can see, that the base and the leaving group are on the same side. So it's also sterically disfavored. You think about the lone pairs on the base and the lone pairs on the bromide. Those are going to repel each other as soon as that base gets close to that bromide. So that's the second reason why that's disfavored. All right, so that's on the next page. Talks about why we don't get that. Everything we just mentioned. Antipary planar is a staggered conformation. This one has an eclipse. That's not going to favor it. The base and the leaving group are on the same side of the molecule. It's just sterically disfavored. In the anti-elimination, they're on opposite sides. We want those guys as far apart from each other as possible. OK. All right, questions so far? Yes? So will it happen to you, sir, or is it just the comparison? I'm not going to ask you that. I don't want you to draw it. So you're only going to get anti-pary planar in this class. So I have students who, I guess it's possible to have an NR, no reaction, for one of my predicting products. But historically, I don't do many of them. I don't usually have reactions that are no reaction. I usually have an answer. So I have had students before that were not doing well in the class, right, NR, NR, NR for every reaction for predicting products. That's not a good idea in my class, because they don't often have reactions that are no NR. I just won't give you one. That has to have an eclipse conformation. All right. OK, so let's see what happens when we're in a six-member ring. Now it's going to look more complicated here. This is a menthol chloride. And first, we want to see a couple of different things. First, let's find the beta hydrogens. First things first, let's find the beta hydrogens. So we zero in on the leaving group. So this is alpha. The right next store is beta. OK, so now let's look here. This is the most stable conformation where the halogen and the isopropyl group are equatorial, right? All the groups are equatorial. So this is the most stable conformation. But the beta hydrogen and the leaving group are not antiperiplanar. In a cyclohexane ring, the beta hydrogen and the leaving group can assume an antiperiplanar conformation only when they are both axial. So the chlorine's not axial. We have some beta hydrogens that are axial, but the chlorine also has to be axial. So in a six-membered ring, antiperiplanar equals transdiaxial in a six-membered ring, antiperiplanar equals transdiaxial. So both the leaving group and the beta hydrogen have to be axial, and they have to be trans to each other. If they are not trans to each other, you will never get a reaction in a million years. So that's OK, because this ring is flipping rapidly back and forth, right? So we can actually flip this ring and put it in the conformation where the chlorine is in the axial position. You know how to do that, right? In chapter 6, you thought you were done with that. In chapter 5, you thought you were done with that, you're not done with that. You still have to know how to do that. So we're going to flip this ring. So now remember, we're looking for the headrest. Here's the, this is all going up here, headrest. That's the footrest. So when we flip that, this carbon right here is going to be down, and this carbon right here is going to be up. So need to know how to do that. So that means that this isopropyl group, which is down, is now going to be axial. Let's look in a little weird. Let me fix that. Let's try that again. So that isopropyl is down. This hydrogen is up. Then we, remember, we travel around the ring. We're going to go clockwise. So the next carbon here is chlorine. Chlorine is going to be up. Now, normally, we want to break the back of that ring, but I can't because it's already drawn there. But the chlorine is going to be up. If you draw that on your test, you want to break, oh, why did it do that? You want to break the back of that ring. OK, then we follow it around. There's chlorine. Next carbon has two hydrogens, so we're skipping that one. And then we have this one here. This methyl is up. All right, so that's not the most stable conformation, but it still is flipping back and forth. And that's the conformation we need to be able to eliminate a beta hydrogen. So let me draw in these hydrogens here. So can you see that there's really only one hydrogen that we can remove? They have to be trans-diaxial. So this hydrogen right here is not to assist to the chlorine. So we cannot, in a million years, eliminate that hydrogen. We can, however, eliminate this hydrogen. If we eliminate this hydrogen, that will give us the most stable alkene. But we can't eliminate that hydrogen because that would be sin. We're not going to see sin. So we're going to eliminate this hydrogen. So in order to get sin elimination, anti-elimination can't be possible. So that's not going to happen. So this is the only hydrogen that we can eliminate. And we know one thing is that these inter-convert freely at room temperature. So the fact that we can't eliminate from that conformation is not a problem. So no problem. Chair flip is rapid. Even at room temperature, it's rapid. All right, so here's our alpha. Here's our beta. Here's our beta. Can't eliminate this hydrogen because it's not trans. It is cis, and you can't eliminate the cis hydrogen. This is the only hydrogen that you can eliminate. All right, so I'm going to eliminate that hydrogen. Let's use blue. Let's see. It does. Me too. What's going on? What did I just do? OK. Well, use blue. OK, so if oxide comes in, boom, removes that hydrogen. This goes here, leaving group leaves. I'm going to draw it the wrong way, and then I'm going to draw it the right way. So let's draw the product the wrong way. And then we're going to put an x through it. We're going to spend all this nice time drawing, and then we're going to put an x through it. OK, I'm going to draw a drawing with the mouse, guys. I know, right? Well, that's a terrible bit. I'm so embarrassed here. Look at that chair. I've never drawn such a bad chair. We're sure taking a long time to make this point, aren't we? OK, what's wrong with that drawing? Oh, that's crazy. You can't see it? Besides that, it looks like terrible. What is wrong with that drawing? Can you have a trans double bond in a six-membered ring? You can't. It's geometrically impossible. Try to do it at home. You can't won't be able to do it with those models that you have that are in the green box. My models are a little bit more flexible. I'll bring one next time so you can see it, or you can come to my office next week to see it. It is absolutely geometrically impossible to have a trans double bond in a six-membered ring. So really, the best way to draw this is actually flat, and I will let you draw it flat. Because as soon as we put a double bond in that six-membered ring, it's not a chair anymore, anyway, is it? It's not a chair anymore. OK, so we want to put a big, can I change colors? Oh, look at that. So we're going to put an x through this. And what we want to do is we want to draw the right way. Let's draw it flat. So I'm going to just draw a flat sacrohexane ring. Oh my gosh. Some people do draw it like this on exams, I believe me. OK, so there's a nice apropo here. That's down. Does everybody see that? This is so funny. That's down. What about this group over here? That's a methyl, believe it or not. That's up, isn't it? So that's the best way to draw this. OK, that's the right way to do it. So this is correct. So on your page right, cannot have a trans double bond in a six-membered ring. I'm not going to draw it on here because it's going to look like a kindergarten wrote it. This is the correct way to draw it. OK. Questions, anybody? So we keep going on this. This is a lot of drawing in this drawing right here. So even though conformation B is less stable, elimination occurs through the conformation because the beta hydrogen and the leaving group are trans-diaxial. Yes. Just turn the tablet off and turn it back on again. How about that? OK. All right, with the neomental chloride, there are two beta hydrogens that can be eliminated. This is neomental chloride. Let's look at it. First of all, let's find our hydrogens. All right, so alpha is the carbon bonded to the leaving group. We have two beta hydrogen and a beautiful thing is happening here. Both of those hydrogens are anti and in the same plane. They're trans-diaxial, which is the same exact thing in a six-member grain. Antiperiplanar is trans-diaxial. So we've got two possible protons that can be eliminated. So let's do one of them. I'm going to do one of them in red. Like that. We're going to eliminate this hydrogen here. Electrons are going to come down, kick off the leaving group. All right, that's one possible product. Let's draw that product. We'll call that pathway A. Oh, come on. You're doing it again. It's doing it again. Oh, jeez, please. We'll just won't change colors. That's A. Let's draw the product. We're going to draw it flat. We're going to save ourselves some grief here and draw these things flat. So this methyl is up. Here's our double bond right here. Don't draw this isopropyl group down. Why don't I want to draw this isopropyl group down? It's down here. So see how it's down right here? Why don't I want to draw that with a wedge? It's trigonoplane or carbon. So that means this carbon, that carbon, that carbon, that carbon, and that carbon are all in the same plane. So there's a sapling problem like that that asks you to pick all of the atoms that are in the same plane. And so we have a double bond here, so that means this carbon's in the same plane, that one, and the first atom attached. So those carbons I'm going to put in x. I'm going to put, let me see if it'll let me. This carbon right here, this carbon, that carbon, that carbon, and this hydrogen. So the two atoms of the double bond and the first atom attached are all in the same plane. So you don't want to draw that wedge. So that's one product. Let's do b. See if it's going to let me do it. I'm risking things here. So we'll call this b, this oxide. Now we're going to remove the other beta hydrogen. I'll just put this arrow on the other side here. OK. Let's draw product b. OK, we're back to the mouse. Now we're going to have to give them a little call about this tablet here. That is a double bond on the bottom there. That's a methyl. This is an isopropyl. Let's draw it this way. All right, now which one is going to be the major product? We've got two possible products. Which one's going to be the major? Top one or the bottom one? Top one is more substituted. So what do we actually get? 78% here, 78% and 22% here. So this top one is favored because it's the most substituted. I'll let you write that and not me write that. Pavor because it's the most substituted. We still have two more minutes of this. I'm going to turn this off and turn it on again. We just have to keep doing that. I don't know. All right. OK. OK, so definitely let's write this for posterity here. Most stable favored because more substituted. All right, we've got one more minute. When a mixture of stereoisomers is possible from the E2 reaction, the reactant has two hydrogens bonded to the same beta carbon, both the cis and trans isomers. Will be formed because there are two conformers in which the groups to be eliminated are anti. The alkene with the bulkiest groups on the opposite sides of the double bond will be formed in greater yield because of the more stable alkene. All right, so that's the last part of this. We've got two possible products here. I still, the clock has not turned yet, so we have this. And trans. Well, is it cis or is it trans? Hard to say because we have more than two groups attached. Which one of these has the bulkiest groups on opposite sides? First one or the second one? First one, and that's the major, 41%. And this is 14%. And then very minor is the least substituted. I'll draw that real quick, and then we'll end here. This one is minor. All right, that's a perfect stopping point. We'll stop right there, and we'll continue this next time. Hope you have a great weekend.
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This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: 00:08 - Regioselectivity of the E2 Reaction: The Zaitsev Rule 07:51 - The Stereochemistry of the E2 Reaction
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10.5446/21625 (DOI)
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We're going to start chapter 9 today. I am going to be going fast for the first couple of pages because it's just introductory stuff that's not very exciting and not super important. So I am going to do a tiny bit of nomenclature, but we're not going to worry too much about nomenclature. Okay, so I probably will have a token nomenclature point question on the test, just so we know how to converse a little bit, but I don't want to spend a whole lot of time on it. All right. In this chapter we talk about alpha-alcohol ethers and epoxides, and this is really a continuation of chapter 7, 8, and 9. It would just be such a huge chapter so we don't put them all together into one chapter. So alcohols contain a hydroxy group, which is an OH group bonded to an sp2 or sp3 carbon. And so if we look here, we've got OH bonded to sp2 examples. We have, here's our hydroxyl. That's our hydroxyl group. This would be methyl. Okay, then if the carbon that's bonded to the OH has a 1R group, that would be primary. So 1R group. If the carbon bonded to the hydroxyl is bonded to 2R groups, it's secondary. And then if it's bonded to 3, it's tertiary. So you're really actually already familiar with the tertiary because we've been using terpitoxide, the conjugate base of this alcohol, throughout chapter 8. So that would be 3R groups. All right. We also have some examples of OH bonded to an sp2 carbon. So this would be vinyl alcohol. That's a vinyl alcohol, also known as an enol. We'll come back to that term coming up in OKM. But that's also an enol. En is for the alkene and all is for the alcohol. So that's why it's called an enol. This would just be phenol. And then I skipped these two on what would we call this alcohol right here? Allyl alcohol, I heard somebody say. So you can pat yourself on the back for that. That's allyl alcohol. And this is benzyl alcohol. So that has a benzyl group bonded to the, let's just re-spell that, BENZYL. This is benzyl alcohol. Because there's a benzyl group bonded to the hydroxyl. Ethers have two alkyl groups bonded to an oxygen. The alkyl groups can be the same or they can be different. If they're the same, we call this is a symmetrical ether. And if they're not the same, this is an unsymmetrical ether. So nothing so terribly exciting. If the ether is part of a three-membered ring, it's an epoxide. So this is an epoxide. You will also see it in some textbooks called an oxyrane. I learned it as epoxides, so I favor that term. You won't see me calling it an oxyrane, but that's a common term also for epoxides. We're going to, like I said, very briefly going to do some nomenclature. Common names. We need common names when we're talking. So like alcohol, the kind that you drink. That would be ethyl alcohol would be the common name. We can also call that ethanol. That would not be the common name. So some of them we need to know a few. So IUPAC, let's talk about IUPAC names. Falling rules are used to name a compound that is a functional group suffix. Select the longest continuous carbon chain to which a hydroxyl is attached. The parent chain is named by dropping the E of the alkene and adding O-L. And then you get a number, the continuous chain, to give the carbon bearing the hydroxyl, the lowest number. This number is included in the name. So this would be, this is about the difficulty I would give you on a test. So let's do that one. All right, so there's the longest chain. Five carbons, so that would be pentane, but we drop the E and add O-L. So the parent, pentane, all. That's our parent. And then we're going to number in the direction that gives the alcohol the lowest number. So we're going to number this direction here. One, two, three, four, five. So our substituents here. We have two methyls. So we have, and they're at carbon four, so we have four, four dimethyl. And so there actually, now that we have all of those, there's two names that we can call this. You will see both. Four, four dimethyl. So four comma four dash dimethyl. Two pentanol. Oops. The two is there to tell you that the alcohol is on carbon number two. That's very important that you do that. The other way you can name this is four, four dimethyl. Pentane, P-E-N-T-A-N, dash two, all. Okay. More common to see it the first way I named it. So all we're doing here, the only difference here is we're taking and we're putting the two right in front of the O-L rather than at the beginning of the pentanol. And both of those ways are absolutely acceptable for us. Question, yeah? No. There is no E after the pentane. We drop the E and add O-L. So that's this right here? In the second one? Nope. We drop the E and add O-L. So we do not add that E back in. No, we don't. Okay? If you have an alcohol in a ring, a number is not needed to designate the position of the function group suffix in a cyclic compound because it's assumed to be in the number one position. All right, so this is automatically going to get number one. So that hydroxyl, what we say is that hydroxyl has priority over all of the alkyl groups. It gets the number one position, yes? That's a little bit different and we're not going to worry about that. So that would be a diol. We would put the numbers and then we'd have other substituents. Yeah, that would be one, two diol, one, three diol, one, four diol, something like that. So we want a number in the direction to give the next substituent the lowest number. So we look like that. So number in the direction to give the next substituent the lowest number. All right, so our parent, this is a six-membered ring, so it's cyclohexane. We drop the E and we add OL. So the parent is cyclohexanol. The substituents are, let me see, what we have, a two-methyl. We have a four-ethyl. No, a five-ethyl. We have a five-ethyl. Let's fix that. Two-methyl, a five-ethyl, and so this would be five-ethyl. Ethyl comes first because E comes before M and the alphabet. Five-ethyl, two-methyl, cyclohexanol. Notice I did not have to put a one in front of the cyclohexanol. I didn't have to say cyclohexane, one-ol, because the one is understood. Okay, you think you could do that? Name something like that? Nomenclature of ethers. Okay, you know, we're very briefly going to cover nomenclature of ethers. I'm not going to test you on nomenclature of ethers on the exam. How about that? Just be a regular alcohol. You know, when I was a student, it was really important to cover nomenclature because I had to go to the library and I had to look these things up in a book. And if I didn't know how to name them correctly, I would never find them in a million years now. All these search engines, you can actually draw the structure and so it's not so critical that you know the exact name. So I kind of take it like that and I say, well, you've got to know a little bit of nomenclature so we can converse, but I don't want to be too hardcore about it. All right. So I mean, you'll see some high school chemistry classes and they say, oh, we taught some O-chem in our class. And basically what that means is they did a little nomenclature. And that's like so not even at all touching organic chemistry as you probably already appreciate, right? Okay, so common name, name the two outcomes substituents in alphabetical order followed by the word ether. Are we going to be hardcore about alphabetical order on common names? No. Okay, IUPAC, name as an alkane with an RO substituent and RO substituent is named by replacing the eel ending with oxy. So let me show you what we're talking about with that one. So this one, for example, let's name it common first. Butyl isopropyl ether. Butyl isopropyl ether would be the common name. IUPAC. What we would do is we would take the longest of the chains or the one that's the simplest of the chains and that will be our parent. So this would be right here. That's our parent. So this would be butane. And then we're going to name this other group. This is an isopropyl group, right? So including that oxygen. It's an isopropyl group, so that's isopropoxy group. So isopropyl, we're going to drop the YL because it has an oxygen and change that to oxy. So this is isopropoxy. So that's our substituent, isopropoxy. So our IUPAC name would be 1 isopropoxy butane. All right, and so we could get really hardcore on this if we wanted to. We're not, I'm not even going to ask you to name ethers, but if I name an ether, I want you to recognize what it looks like. And I would probably call it by its common name. So that's all I want to know for naming ethers. Questions? So far, anybody? Yes, up at the top. The one is necessary. So the only time the one would not be necessary is if it could only be a one. So in other words, this isopropoxy group right here, that could be here or it could be here. Okay, so that would be at number two. So we do have to distinguish those two possibilities. All right, so if it was an ethyl, then, you know, we would probably name it differently, but then there's only one place it could be. All right, preparation of alcohols, ethers, and epoxides. And this is going to be basically a review reactions from chapter seven. So no news, no terribly new stuff so far. Alcohols and ethers are common products of nucleophilic substitution. If we want to make an alcohol, we take an alkyl halide and hydroxide ion. Okay? So that would be an SN2 reaction. Backside attack, kickoff bromide. And we get an alcohol. So that's our synthesis of alcohols. We already know how to synthesize alcohols. Synthesize all alcohols that way, but we can certainly synthesize a large amount of alcohols that way. And ethers prepared by treating an alkoxide with an alkyl halide. This is known as a Williamson ethers synthesis. So we're now naming that reaction. We hadn't named it before, but we've already done this reaction over and over and over again in chapter seven. So when you take an alkoxide plus an alkyl halide, you have a Williamson ethers synthesis. So let's write that down. So Williamson ethers synthesis, alkoxide plus alkyl halide to make ether. Williamson ethers synthesis. All right, so same idea as the hydroxide. We're going to have the great nucleophile. This is going to be an SN2 reaction. Come in, do backside attack, kick off bromide as a leaving group. Here instead of using an alcohol, we're using an alkoxide. So that is going to give us an ether. Great way to make ethers. All right, we have to be really careful here when we are synthesizing ethers. The reason is this alkoxide base is pretty strong. And we know if we have a great nucleophile that's a strong base, we have to watch out for elimination. So we have to really pick our alkyl halides really carefully or we're going to get elimination as the major product. And when you're trying to synthesize something, you don't want the minor product to be major. All right, so for example here, this is a synthesis problem. So this is rather than me giving you the two reagents and asking you to predict the product, you're asked to synthesize this. So this is probably one of the first times you've ever had to do that. We're going to start doing that a lot in this quarter. All right, so the following ether are choosing reagents that would give the best yield. So as you can see, we want to use a Williamson ether synthesis. We've got two possibilities. We could, let's give one possibility here. We can form this bond here. We've got two oxygen carbon bonds and we can form either one of those. Let's call that pathway A. And the other thing that we can do is we can form this bond. We'll call that pathway B. All right, so Williamson ether synthesis, I'll kill halide plus alkoxide. If we're going to form this bond right here, which alkoxide would we use? This whole guy right here is going to be our alkoxide, somethoxide ion. So if we want to form this bond, we'd use a methoxide ion right here and then this would be our alkyl halide. So an isopropyl halide. If we're going to form this, if we're going to form this bond on the other hand right here, there's our alkoxide. Isopropoxide is our alkoxide. And then we'd use methyl halogen, so methyl halide, bromide, iodide, chloride, something like that. So let's write out those two possible pathways and see which one's going to be best. All right, so let's do route A first. So if we're going to form A, we would use isopropoxide and methyl iodide. We can use iodide, chloride, bromide. I'm feeling iodide right now. And when you're in the driver's seat, you can pick whatever you want. It's kind of a very powerful thing. All right, let's show route B. Now I'm feeling bromide this time. So route B, I'm going to have isopropyl bromide and methoxide. So the question is, which route is the best, route A or route B? A is the best. Why is route B bad? Fantastic. You guys are doing great. Route B is bad because we have a secondary alkyl halide and a strong base. And this is a strong base. If you do this route, you're going to have E2 as your major product. All right, so this guy's going to be the best. Alkyl halide is not hindered. Will we get any elimination with methyl iodide? No. Why won't we get any elimination? There's no beta carbons. No beta carbons means no beta hydrogens. So no elimination. All we have, no competition for this reaction. We will get 100% of the product that we want. So alkyl halide is not hindered and has no beta hydrogens. Therefore there will be no E2. So that's the route that you want to choose. So already we're starting to have to be a little analytical here when we're figuring things out. So that's the route we want to do. Questions on that example? Anybody? A hydroxide used to form alcohols and an alkoxide used to make an ether, alkoxide can be formed by treating an alcohol with sodium hydride. All right, so we're going to use sodium hydride to turn our alcohols into alkoxides. Acid-base reaction, let's draw this out. Make sure it's favored in the direction we want it to go. So our conjugate acid is H2. So hydrogen gas. So I might put the little gas symbol in the arrow means that it's going to bubble away. That's going to drive our equilibrium to the right, isn't it? And if we look up PKI, so this arrow just means this is going to bubble off reaction mixture. We want to look at the acid on each side of the equation. This is our acid on this side. So that's going to be PKA about 15 using our PKA's rounded to the nearest 5. This is our acid over here. PKA is 36. That's not one of the ones you need to have memorized. I would have to provide that for you. All right, so we have definitely very powerfully driven to the right. But maybe there's a little bit of reverse reaction if we catch the H2 before it bubbles off the reaction mixture, that's possible. But at equilibrium we have about, what do we have? 21. So it's 1 to 10 to the 21. So if you didn't have me last quarter, basically what I did is I took the difference in PKA's and that means that at equilibrium that's ignoring the fact that the hydrogen is bubbling off and driving it even further to the right. We will have one molecule of alcohol for every 10 to the 21 molecules of alkoxide. So this is a fantastic. Is that screen always shaking like that? Okay, it's stopping now. So that means this is a really good way to convert alcohols to alkoxides, right? It's essentially to completion. All right, so now let's go and look. The question comes, why can't we just use hydroxide to form an alkoxide from an alcohol? Let's look at that equilibrium and see if that's going to be doable. All right, we're going to do the same thing. Now we're going to use a much more familiar base. Let's try this again. All right, oh boy, let's see what we got doing. I'm staying away from that purple color. I'm so facetious. That's when it froze up. Okay, so we've got this here. So we're all wondering, and now you're just really killing you. The anticipation is really killing you now. So we've got, there's our alkoxide. Our conjugate base is water. Let's look at the pKa for each of these. Now the good news on these guys is that for both of those, we know those pKa's rounded to the nearest five. That's part of the pKa's rounded to the nearest five. That's one of the, those are two of the, well, one of the eight, okay? So this is about 15, and this is about 15. So what that means is that, so we have a 50-50 mixture here. So at equilibrium, we have about 50-50. 50-50. So what that means is that we're not really going to be making enough of that alkoxide to use it in a Williamson-Ether synthesis. Let's say we wanted to make, we wanted to make a thoxide, and we mixed it with hydroxide, and then we added methyl bromide. Well, we're only going to be making 50% of that. So we're going to get a mixture, because we're not making enough of that, of thoxide. So the base that we want to use definitely is sodium hydride, the base to use, and this is the only base that I will use, the base to use to make an alkoxide from an alcohol. Okay. An intramolecular version of the Williamson-Ether synthesis provides a route to epoxides. Let's look and see what that looks like. H minus, that's our good base, that's the base we want to use. Let's do arrow pushing here. Now I'm going to keep this alkoxide in the same orientation that it's in, because I want to point something out to you. Okay, so what's going to happen is this alkoxide is perfectly situated to do intramolecular backside attack and to kick off this bromide ion. Let's draw the product we get from that. Notice this is a three-membered ring ether, also known as an epoxide. So our nucleophile and our leaving group are in the same molecule. So let's label those. Here's our nucleophile and here's our leaving group. So we call this type of reaction where the nucleophile and the leaving group are in the same molecule as an intramolecular reaction. So this is an intramolecular Williamson-Ether synthesis. A molecule that contains both of these can actually undergo intra or inter. How do we decide? Okay, so really the question here is how do we know that this alkoxide is going to attack in the same molecule? Why can't that alkoxide come back and kick off the leaving group in another molecule? That would be intramolecular. And it attacks in the same molecule, it's intramolecular. Alright so let's see. Here's an example here. Let's see if we can decide. So this is CH2N so we're talking about varying ring sizes. So let's do the intramolecular down here. Let's see what that would look like. Little bit larger ring isn't it but it's still the same thing. But if we do that we form a ring. If we don't do intra and we do inter let's draw that. Inter-molecular. What would that look like? We would have this alkoxide come in, do backside attack and kick off this leaving group in another molecule. So it kind of looked like that. So what we would get is something that looks like this. That's what it would look like if it did intermolecular. So we want to be able to know what we're going to get. We want to be able to predict what we're going to get. So how we know what happens is it depends on the size of the ring. So there's a magic number. 3, 5 and 6 membered rings. The ring is favored. The ring is favored. So if we can make a 3-membered ring and when we say the members of the ring we're counting the oxygen. So this one up here, the alkoxide, that's a 3-membered ring. And so if we can form a 3, a 5 or a 6, the ring is going to be favored. If it's a 4 or greater than 7, so that's a greater than 7, it doesn't look like that. But I'm sorry, greater than 6, that would make that easier to read here. 4 or greater than 6, ring is disfavored. And therefore you're going to get the reaction on the top here, intermolecular instead. It depends on Williamson-Ether synthesis. Anybody? All right. We're going to talk about a new reaction called dehydration. It's going to look a little bit familiar to you. It's going to look very familiar to you, hopefully. And so basically what we do is we take an alcohol, concentrated sulfuric acid, tosyc acid, or H3PO4. I will tell you that the only ones that I will use will be these two. So phosphoric acid I don't use. So I won't use that on tests for you guys. So what is tosyc acid? Well that's this guy right here. Tosyc acid, and so you can see it's in the same family as sulfuric acid. Basically all we've done here is we've taken one of these hydroxyls off and replaced it with an R group. But they're both really, really strong acids. So we don't change the acidity a little. We don't change it a lot. The reason why we sometimes like to use this acid instead of sulfuric acid is that this acid has better solubility with organic compounds because it's got that, you know, this hydrocarbon part here. It's got better solubility. So that's it. But those pretty much we're going to be using interchangeably. And so this one here is more soluble inorganic solvents. Alright we're going to go through the mechanism now. The mechanism depends on the structure of the alcohol. As you're going to see, the first step will be the same for every alcohol. So first step for all alcohols. Alright so I'm very particular about mechanisms. And so for mechanisms I always want the arrow to come from a pair of electrons, either a lone pair or electrons in a bond. And all of the atoms, all bonds that are breaking are drawn out. And everything that's involved in the arrow pushing needs lone pairs. So I'm going to do arrow pushing involving this oxygen only. So that means I don't have to put lone pairs on all these guys. But I do need to put lone pairs here and I do need to put lone pairs here. Alright so what I'm going to do is I'm going to grab this hydrogen right here and I'm going to break this hydrogen-oxygen bond. Just like that. So now all I've done is I've protonated the alcohol. So it looks like this. Our side product would just be the conjugate basis sulfuric acid. Alright so that's going to be the first step whether we have a primary alcohol, secondary alcohol, tertiary alcohol. For the second step secondary and tertiary alcohols go through an E1 mechanism. So I'm going to draw a secondary alcohol here. So what we're going to end up doing is re-going through the same step here but that's good because it's good practice. We've got sulfuric acid. If you don't want to draw out all those bonds you just have to draw out the bonds that are being made and broken. So we can do this little business here if we want to save ourselves some time. So now we're going to come and grab this hydrogen. We're going to break the hydrogen-oxygen bond. And I'm actually going to draw reversible arrows. I'm going to come back and draw reversible arrows here. These steps are all reversible. We know that all the acid-base reactions are reversible. This one also is reversible. So secondary and tertiary alcohols go through an E1 mechanism and that means that for secondary alcohol E1 mechanism is faster than an E2. So what happens in an E1 mechanism, this leaving group is going to leave. We're going to make a carbocation and that's going to be our rate determining step. So rds for rate determining step. All right. Now we just learned E1 so it's fresh on our minds. So what do we do in the first step of an E1? Our leaving group leaves. So the only difference here is our leaving group is water rather than a halogen. That's the only difference. In the second step of an E1 we eliminate a beta hydrogen. So what are we going to use for that? Let's see. What do we have here? Probably we have a little bit of, let's use the conjugate base of sulfuric acid. We have a little bit of water here in sulfuric acid but not very much. It's usually concentrated sulfuric. It's about 96%. We do have some alcohol. So let's just go ahead and use the conjugate base of sulfuric acid here to do this elimination. So the one thing I don't want you to do is just use a generic B or A for acid. I want you to use real things that are actually in there. So this is going to come, remove beta hydrogen and there's our alkene. Let me fix that. And I'll draw all those guys out. I think you guys like it better when I do that anyway. It's a little easier to see. There's our alkene product. That's our dehydration product. So I want to go back here and do another reversible arrow here. So that's our product. Questions on that mechanism, anybody? What's the mechanism for dehydration of a secondary or tertiary alcohol? Primaries go through an E2. Why can't a primary go through an E1? Yeah, you can't make a primary carbocation. So why? Why can't you make a primary carbocation? All right, so let's draw it. We're going to still have the same first step, which is protonation of the hydroxyl. Why do we protonate the hydroxyl first? Anybody know that? Exactly. Exactly, we want to make it a better leaving group. Hydroxyl is a poor leaving group. PKA of the conjugate acid is about 15, so it's a terrible leaving group. We're not going to have it leave. So that's why we are protonating it so that it can leave more easily. All right, so since we're primary, we're not going to make a primary carbocation. There's our protonated alcohol ready to go, except instead of having it leave first, it's going to leave as we remove the beta hydrogen. So we'll do our conjugate base of sulfuric acid. If you want to do it abbreviated, it would look like this. This is going to grab the hydrogen. We're going to move electrons here. Leaving group's going to leave. All reversible. There's our product. So that's the simple way of drawing, and I keep doing that. I keep telling myself, you've got to draw it out. This is better for everybody. This is the way, more easy way to see it. We'll draw it this way. All right, questions? Anybody? So E1, E2, do you see how this is kind of a continuation of that previous chapter? Chapter 8. We still have a couple of minutes, guys. Because of all these steps are reversible, this is an equilibrium process. The two sigma bonds broken in this reaction are stronger than the pi bond formed. Since equilibrium requires reaction's favor, more stable products, the equilibrium is favor to the left. In order to obtain an alkene product, the reaction has to be driven to completion. It's an uphill reaction. We have to drive it to completion using Le Chatelier's principles. System at equilibrium will react to counteract any disturbance in the equilibrium. So here's our complete reaction drawn out. To drive the equilibrium, there's different ways to do this. One way, and you'll do this in the lab, is to remove the alkene as it's formed. So you're going to be running, if you have my lab, we've already done this. If you don't have my lab later in the quarter, you'll be doing this reaction. And your alkene is going to be a gas, and it's going to be removed as it's formed. That drives the equilibrium, so I like to distill it off. And the other way is to keep the concentration of water low. And to do that, we use concentrated sulfuric acid. That's why we use concentrated sulfuric acid here. If we use dilute sulfuric acid, it would go back the other direction. All right, we will stop right there, and we will continue this on Wednesday. I hope you guys have a great long weekend.
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This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: 00:47 - Introduction 04:15 - Nomenclature of Alcohols 10:47 - Nomenclature of Ethers 14:59 - Preparation of Alcohols, Ethers, Epoxides 34:06 - Elimination Reactions of Alcohols: Dehydration
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10.5446/21626 (DOI)
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So we were talking about dehydration last time. And the mechanism depends on whether we have a primary, secondary or tertiary alcohol. If we have a primary alcohol we get an E2 mechanism. If we have a secondary or a tertiary we get an E1 mechanism. Alright so that's where we left off last time. Rate of reaction corresponds to the ease at which the carbocation is formed. Okay. Rate of reaction corresponds to the ease at which the carbocation is formed. So does that make sense that tertiary is going to be the fastest? Right? Okay. So in these typical conditions I do not want you to memorize these conditions. I'm trying to just give you a comparison here. So tertiary alcohol, heat to 50. Whoops we didn't do our. Okay let's try that again. We're just not going to get a break here are we? Alright. So tertiary alcohol, heat to 50. 50 degrees centigrade in 5% sulfuric acid. Typical conditions. Okay. Secondary alcohol. It doesn't form a carbocation as readily. It's going to be more stronger conditions. Heat to 100 degrees in 75% H2SO form. So that would be 75% H2SO form, 25% water. So primary alcohol, heat to 170 in 95% H2SO form. So we're seeing here a trend here. The more substituted the alcohol the faster the reaction. Why wouldn't primary alcohol, we're not actually making a primary carbocation. Why would primary alcohol be so slow? What do you think? It's, remember, it's E2. What does an E2 require? Strong base, right? E2, both the base, and the alkyl pate line are both part of the ratio of the step. So we need a strong base. Do we have a strong base here? The ratio of the beta hydrogen is a quantity based on the soldier of gas. So that's the, we would call this forcing conditions. Goes by E2 because primary carbocations are too stable, are too unstable. Alright, so, and then let's just label this because when you come back and look at this page, you're going to think, oh, do I have to memorize that? Typical reaction conditions don't memorize. And so we already answered the question, why does the primary alcohol need forcing conditions? And that's because E2, E2 reaction requires a strong base. HSO4 minus is a very weak base. Alright, so, so your book is going to have some examples of elimination of primary alkyl halide. I don't want you to do it. So I'm going to say don't do dehydration of a primary alcohol. Alternative at the end of this chapter. What is the last page of this chapter in your handbook here? What's the last page? Alternative on page what? Very last page. What is it? On page 47. Okay, and what's going to happen is I teach the honors in majors lab. We've already done an elimination. You guys are going to do the same experiment in week five. And what you're going to find is that you don't get a good result from the primary alcohol. So all of this will make more sense when you do that experiment. I don't want you doing dehydration of a primary alcohol on any of my tests. I know that Smith has questions using it. I don't want you to use it. And you'll see more why that is when we get to chapter five. Alright, stereochemical outcome of this E1 dehydration is the same as the stereochemical outcome of an E1 elimination of an alkyl halide. The ZYDE-SAF product. Which can be a mixture of cis and trans. A mixture of cis and trans with more of the isomer with the bulkier groups on opposite sides. More of the isomer with bulky groups on opposite sides. Alright, so just as we would expect. And now we're going to introduce something new here about carbocation that we didn't tell you before. This is something that was actually happening behind the scenes in chapter seven and chapter eight. And we didn't mention it to you because we didn't feel like you were ready for it. So it's kind of like when you have little kids, you don't tell them that there's a Santa Claus. And then when they get a little older, then they realize that there's no Santa Claus. So now you're ready to know that carbocations are not as well behaved as we have been painting. A picture of them being well behaved. One of the things that they do is they do rearrangements. So that means when you go back and you work problems in chapter seven and eight, there's actually extra products that weren't accounted for that actually do form in those reactions. And really, anytime we form a carbocation, we can get rearrangements. So first of all, I want to talk to you about what a rearrangement is, and then we'll talk about when we'll see a rearrangement. So it's not every single time, but it's a lot of the time. Some dehydration, E1 and SN1 reactions. So we're kind of going this back to chapter seven and eight, give unexpected products in which the nucleophile appears to have added to the wrong carbon, or the carbon skeletons have been rearranged. And that's actually exactly what is happening here. Alright, so here's a good example. Here, this is dehydration. How do we know it's dehydration? We have H2SO4 and concentrated H2SO4. And this is our expected product. So if I had given you a little quiz before class, this is the product that you would have written. And this is the rearranged, the unexpected product. And it turns out, in this case, the rearranged product is actually the major product. So first of all, we need to know how that's forming, and then we need to know when to expect that and when to not expect that. So we're going to look at the secondary carbocation formed in this example. So in the first step, we protonate the alcohol. I'm just going to go directly to the second step. Okay, actually let's just show the first step over here, just for fun. I will use the abbreviated form of sulfuric acid. And I'm just going to protonate this alcohol. So I'm going to go over here, grab that hydrogen, break the hydrogen-oxygen bond, and go down here. So this is the second step. In the second step, since this is a primary alcohol that we've started with, we're going to form, I mean, it's a secondary alcohol, we're going to form a secondary carbocation. So that's what happens in that step. Let's draw that secondary carbocation. And this particular carbocation is ideally situated to do a rearrangement. So what does the rearrangement look like? I'm going to change colors here so you can see it a little bit better here. What's going to happen is that this methyl is going to migrate over. So the arrow should come from the middle of that bond there, that carbon-carbon bond. That's going to migrate with its pair of electrons. So it's taking its electrons with it. And when it does that, since it's taking both electrons with it, now the carbon that it just left is now a carbocation. It's electron deficient. That's because it took both of its electrons with it. So now the carbon on the right is no longer a carbocation. The carbon on the left is a carbocation. And you can see that what we've ended up doing here is we've gone from a secondary carbocation to a tertiary carbocation. And we know tertiary carbocations are more stable. So where we're going to see a lot of rearrangement is when we're making secondary carbocations. And if the secondary carbocation can rearrange to a tertiary, it's going to happen. There's nothing you can do to stop it. So it turns out that the elimination, which is the second step here, the loss of the beta hydrogen, can occur from both of these carbocations. So I'm going to draw both of them. I'm going to draw the first one unchanged before the rearrangement. And this is the product that is the expected product. And so we're going to have a conjugate base of sulfuric acid come in and deprotonate, remove that beta hydrogen, and then form a new alkene. So that can happen. And that actually leads to the expected product. But as we said, we can also eliminate from this carbocation. So this is our rearranged carbocation. And what we're going to expect for our major product is going to be the most substituted alkene. So here's our alpha carbon here. This one's beta. This one's beta. This one is beta right here. Which one are we going to eliminate to make the more substituted product? Anybody? If we eliminate the hydrogen on the more substituted carbon, we'll get a more substituted alkene. So that's the one we're going to eliminate. So let's go ahead and do that right here. I'm going to have this come around. Boom. Grab that beta hydrogen. I'm going to go down here and make a new carbon-carbon double bond. That leads to the rearranged product. Questions on the rearrangement? Anybody? Yes? So her question is, we have two different beta hydrogens here. It's going to depend on what I ask for on the test. If I ask for all the products, then I would want you to eliminate the other type of beta hydrogen. So if I ask for the major product, then I'm going to look for the one that's more substituted. So that answers that. Okay, so the methyl migrates with its pair of bonding electrons from the carbon adjacent to the electron-deficient carbon, the carbon from which the group departs as a result becomes electron deficient. Because that methyl is grabbing that extra hydrogen that actually belonged to that carbon and taking it with them. This is called a 1, 2 methyl-ship rearrangements of carbocations or general phenomenon that occur when migration of a hydrogen, methyl, or other alkyl group. So it's not just a methyl. It's a hydrogen-methyl. Other alkyl group leads to a more stable carbocation. Let me show you some examples of each. 1, 2 hydrogen migrations. So it would be something like this. Notice what's different here. We have a methyl, a methyl, and a hydrogen. Okay, so in this case we'd have a hydrogen migrate. So there's the new hydrogen right here, carbocation. Alright, so that would be a 1, 2 hydrogen migration or you'll also call it a 1, 2 hydrogen shift. That's the other thing. And it moves from the neighboring carbon right onto the carbocation. Here's alkyl migration. This is one like we just saw. So this is identical to the one we just saw. So we see that one of those methyl groups is going to end up on this carbon here. It's moved over. And notice we've gone from a secondary to a tertiary. You can also have groups bigger than a methyl. You get an ethyl migrate. In this case you can actually have the methyl migrating like this. So that goes here. And there again we're going from a secondary carbocation to a tertiary. Or we can actually have a carbon from the ring migrate. This is a little trickier to see. I'll do one of these in discussion to give you a little practice here. These are the hardest ones to predict. Let's do this one more time. We're going to redraw this carbocation. And so what this is going to look like is this whole ring is going to migrate. We get a ring expansion. It's a little mind blowing. It is. But that's exactly what it looks like. And we know that a six-membered ring is more stable than a five-membered ring. So not only are we going from a secondary carbocation that has an adjacent five-membered ring, we're going to a six-membered ring tertiary carbocation. So that's really going to be favored. So let's label all of these guys. So this is a secondary carbocation and goes to a tertiary. This is a secondary carbocation and this goes to a tertiary. Secondary carbocation goes to a tertiary. Secondary carbocation goes to tertiary. And that's where we're going to commonly see this. Now I often get the question, can a secondary carbocation go to another secondary carbocation that's about equal stability? In real life, yes, but this is not real life here. In my class, it's going to go to a more stable carbocation, either a tertiary or maybe something that's conjugated, something like that. So that's what you'll see in my class. So what you won't see is a secondary carbocation going to a secondary carbocation that's equal stability, even though that really does happen. Carbocations are not very well behaved. Question? So what is more favored than the second? The second one is going to give you a tetra-substituted alkene. So the most stable product is going to come from this carbocation. Okay, yeah? Do all migrations go to a carbon-directed adjacent to you? Yes. We're not going to see them moving two carbons over, just one carbon over. Okay. So in the first example, the other question that I get is in this first example, why did we migrate a hydrogen? How do we know we don't migrate a carbon? So let me show you what I'm talking about. So we migrated a hydrogen. How are we supposed to know that a methyl doesn't migrate? Well, let's answer that. I'm going to show that. That's at the very end of this page. Let's try it. Let's try having a methyl migrate instead. We're going to go here. All right. So why doesn't that happen? Yeah, you're just going from a secondary to a secondary. Okay, so in this happy little bubble of the first year of organic chemistry, when everything that works is supposed to work and all of that, this is not going to happen because we're going from a secondary to a secondary. So that's the real life that can happen. Not something we're going to worry about for this class. All right. All right, so whenever a reaction leads to the formation of a carbocation, and that includes reactions, that includes SN1 reactions, E1 reactions, from chapter 7 and 8, you must check its structure for the possibility of rearrangement. And I tell you, hey, this is going to rearrange, no. You're going to know that you form a secondary carbocation, and whenever you form a secondary carbocation, you need to look for rearrangements. So you need to know how to do that on your own. I'm not going to warn you. Okay, so this guy, these are the expected. The ones that are from rearranged carbocations, I'm going to put an asterisk next to them. So this one here, that one here. Which product is major? What do you think? The fourth product? Yeah. Tetra-substituted alkene. And here's a dehydration example. This is just like the one that we just did. And so definitely this is the rearranged product. So that's what the asterisk means from rearranged product. And so definitely this one's going to be the major, the second one drawn. And that's a tetra-substituted alkene. All right, so let's summarize dehydration reactions. Use H2SO4 concentrated or TSOH, TOSC acid, plus heat. We want heat so it favors elimination. Works for secondary or primary alcohols. Don't use for primary alcohols. Use alternatives shown on page. That was what, 46 or 47? 47. 47? So change that to a 47. Watch for rearrangements, especially with secondary alcohols and most highly substituted alkanes favored. Okay? All right, so that's dehydration. Now we're going to move on to the second part of this chapter, which is all about taking alcohols. And alcohol has a really poor leaving group, doesn't it? Taking an alcohol and converting it into something that has a good leaving group. That's the major bulk of this middle part of this chapter. And so an alcohol cannot undergo a nucleophilic substitution because it has a strongly basic leaving group that cannot be displaced by a nucleophile. So if you're thinking that this can happen, you may want to take another look at chapter 7. And what we said in chapter 7 is we're not going to have hydroxide as a leaving group in an SN2 reaction. So if you're thinking this is going to happen, that's not going to happen. Let's put a big X through that. That's not going to happen. But what we're going to do is we're going to figure out some ways that we can make a similar thing happen. Not by this method, but by something that's a little bit different. And this is all because this is a bad leaving group. It's a strong base. We know that good leaving groups are weak bases. Strong base, pKa of the conjugate acid. Conjugate acid of hydroxide is water, is approximately 15. So that's sort of in our category of bad leaving groups. Alright, so if an alcohol can undergo substitution, if the OH group is converted into a group, that's a better leaving group. So how about a halogen? If we can take that hydroxyl, we can't do it this previous way that we have on this page, but if we take that hydroxyl and we convert it into a halide, we can do all the reactions from chapter 7 and 8, right? So, and there's a way to do that. We can take the alcohol and treat it with Ajax, converts the bad leaving group hydroxyl into a great leaving group. So this is what it looks like. Bad leaving group. And let's repeat what we had on the previous page, pKa of the conjugate acid, H2O, is about 15. And if we treat this with HBr, we can actually convert this into methyl bromide. And side product is water. All right, so now we've taken that bad leaving group and converted it into a great leaving group. pKa, how do we know it's a great leaving group? pKa of the conjugate acid, HBr, is minus 8. So that's what we want to do. Take the alcohol and convert it into an alkyl halide. So that's the first reaction we're going to talk about in this section. It turns out that we could do this with primary, secondary, and tertiary alcohols, all undergone nucleophilic substitution when treated with Hi, HBr, and HCl to form alkyl halides. No HF. This HF does not work in this reaction. So primary, secondary, and tertiary alcohols can be converted into Rx, where x equals I, Br, and Cl. So that's what we're doing in this part of the chapter. Mechanism is going to depend on the alcohol used. So primary alcohols and methanol reaction proceeds through an SN2 type mechanism. Secondary alcohols and tertiary, those are going to proceed by an SN1 type mechanism. So it's kind of similar to dehydration. We have a different mechanism depending on the alcohol we start with. So let's do primary alcohols and methanol first. First step. So this is a potential mechanism for midterm one, right? What are the potential mechanisms for midterm one? We have elimination. We have E1. We have E2. We also have dehydration, dehydration with the primary alcohol, and dehydration with a secondary or tertiary. So we're already getting quite a list of possible mechanisms. This is another possible mechanism for midterm one. And you're pretty much guaranteed to have more than one mechanism on this first midterm. I emphasize mechanisms quite a bit because they help you learn organic chemistry. They help minimize your memorization. So it's really helpful. All right. Looks like the first step of dehydration, doesn't it? All right. And what we've done there is in a kind of roundabout way, we've taken our bad leaving group and a good leaving group in our intermediate. Okay? Now in the step two of this reaction, we're going to, I'll just redraw this. Our good nucleophile, bromide ion is a very good nucleophile. It's going to come in and do an SN2 reaction. So bromide's here. That's our conjugate base. It's going to come in and it's going to do backside attack. Kick off our leaving group. And you can see where our side product is coming from. That's when water leaves. So we've gone from a bad leaving group to an ultimate product here is this, which has a great leaving group. Questions on a mechanism for primary alcohol and HBR. Anybody? Let's look at secondary. Reaction proceeds through an SN1 type mechanism. Here's an example here. Tertiary alcohol, HI converts it into terbutyliodide. Alright, so the step one is going to be exactly the same. We're going to protonate the alcohol, so let's do that here. Alright, so I'm pretty particular on my mechanisms. I want to see lone pairs on all reacting atoms. If you're breaking a bond, I want you to draw it. There are already bonds that are breaking. Arrows need to come from a lone pair or a bond. So here this arrow is coming from a lone pair. The second arrow is coming from a bond. So it will look like that. This is a very fast reaction. Acid-base reactions are extremely fast. So we've protonated the alcohol. Now, if you're thinking that iodide can come in and do backside attack, that's not going to happen. Why is that? It's a tertiary alcohol. It's a tertiary. So that's not going to happen. Alright, so we're going to lose water to form a carbocation. So far this is looking just like dehydration, huh? Terraprotonated alcohol. Tertiary carbocation. Same thing will happen with secondary. We'll get a secondary carbocation. And if we get a secondary carbocation, what do we watch out for? Yep, if you can have it. You can't always have it. So this is a faster or slow step. Slow step when we form a carbocation. And then we have nucleophilic attack at the carbocation. So I'm going to redraw this. Okay, so the arrow is going to come from one of the lone pairs on iodine. Iodine is involved in the arrow pushing for the step, so it needs all of its lone pairs. So it's going to come and attack the carbocation. This is also a fast reaction. So that's the mechanism that we're going to see when we have a secondary or tertiary alcohol. Alright, important point, order of reactivity for HX. HI is fastest, followed by HBR, followed by HCL. And why is HCL slower? Well, it really comes right down to this step right here. Chloride ion is a weaker nucleophile. Okay, so that's slower. Slower because CL- is a weaker nucleophile. And it's so weak in fact that in your book, in your textbook, the book uses zinc chloride to promote the reaction. In other words, HCL on its own isn't good enough so they take HCL and react it with zinc chloride. I'm not going to have you worry about the zinc chloride. I think we're just going to pretty much stick to HI and HBR and then we can avoid the whole zinc chloride issue altogether. Okay, so that's how I usually handle it. Questions on that point? Anybody? Alright, so order of reactivity for alcohols. Tertiary is faster than secondary, is faster than primary, is faster than methyl. Okay, so these guys, these would be, these undergo SN2. These guys undergo SN1. So what that's saying is that a secondary alcohol, it's faster to make a carbocation than it is to undergo backside attack. It is much faster for a secondary alcohol to make a carbocation. Maybe a little surprising, but that's really what that is telling us. So it's faster for a secondary alcohol to form a carbocation than to undergo backside attack. So SN2. Maybe surprising, but that's actually the case. It's actually faster. And that's because SN2 on a secondary alcohol that's beginning to get very sterically hindered and that slows the reaction down tremendously. So this reaction is best for primary, methyl, and tertiary substrates. Reaction doesn't work well for secondary. And I don't want you to use it for secondary. We're going to show, I'm going to show you some alternatives coming up. Okay, so don't use for secondary substrates. If we have a secondary alcohol, we want to turn it into an alkyl halide. We're going to use another reagent. Don't use for secondary substrates. Why is this, why? It's because it's a secondary substrates. All right, so here's the reason, the long reason. Secondary substrates, I can undergo both SN1E1 and SN2E2 depending on the conditions used. Under the conditions of this reaction, strong acid, strong aqueous acid, SN1E1 pathways are favored over SN2E2 pathways for secondary substrates. It is faster to make a carbocation than it is to undergo backside attacks. So the reaction proceeds by way of a carbocation intermediate which can rearrange. So now that we're alerted to rearrangements, that's what's going to, we're going to have to worry about those happening. Let's go through this example here. Okay. Let's draw the product of that step. We have now a protonated alcohol. This is a secondary alcohol. We have a protonated alcohol. So the next step is going to be for the leaving group to leave. So let's draw the protonated alcohol. And then this is going to leave. All right, let's draw that carbocation. We've already seen that a couple of times. And you'll see it in discussion also this week. Okay, so secondary carbocation, bells should be going off in your head saying, okay, look for rearrangements. Look for rearrangements. And we have a nice rearrangement here. So we have a two hydride shift. So let me change colors for that. Just like this. So the arrow should come from that carbon hydrogen bond and move over to the carbon. So there's a tertiary carbocation. So either one of those products can get, we can get products from both of those. Let's draw both of them. If the bromide attacks before that rearrangement happens, we can get this product. Or if we do rearrange first before the bromide attacks, I'm skipping a step here. Then we can get this product. So that reaction that we were trying to do actually yields two products. So if we wanted to get the unarranged product, then we would have to do separate, we have to separate those two compounds, which is not trivial to do. Those are pretty similar physical properties. It's going to be tricky to do. All right. So we want to use an alternative. Yes, question. Does the hydrogen when it's on the screen, does it sit on either order or is it going to be on both? Before it rearranges? No, after it was a carbon paradise before. Yes. If we're looking at the one for just the hydrogen sitting on both orders, not really, you can come up and we'll talk about that after class. Okay. That's reason number one, rearrangements, right? Reason number two, let's talk about the stereochemistry of this reaction. You love stereochemistry, right? We don't want to leave stereochemistry out. It depends on the substrate used. Primary alcohols. I might give you a problem like this on the test and I'm going to expect you to show the stereochemistry in the product. So let's say we started off with this optically pure primary alcohol. How do we have an optically pure primary alcohol? We used deuterium for one of the hydrogens to distinguish those two hydrogens from each other. Let's go through the mechanism. If you know the mechanism, you will have no trouble predicting the product. If you don't know the mechanism, it's a 50-50 gas. So we'll see how lucky you are on the test if you just do a 50-50 gas. All right. Let's go through it. We know the mechanism, so this should be easy to predict. Hydrogen is going back, this deuterium is coming forward. All right. What happens next? Elimination, right? No? Substitution, right? See how it tricked you there. All right. Backside attack. SN2, inversion of configuration. SN2, inversion of configuration. So you want to show inversion of configuration, so I'm going to have the bromide coming in from the opposite side. There's more than one way to show inversion of configuration. If you have another way to do it, that's also fine. If you have the nucleophilic coming in from the opposite side, then we just move the hydrogen over to the side, and we move the deuterium, but we keep them in the same orientation. And that will give you, so that's SN2, inversion of configuration. It's 100% inversion of configuration. So 100% inversion. Need to know that, so in the product you will draw inversion. What happens if the secondary or tertiary alcohol? Let's go through that. If we know the mechanism, that's not a hard question. If we know the mechanism and we know the structure of a carbocation, that is not a hard question. It's really not a 50-50 guess, because you could have one enantium, or you could have the other, but you could have both, right? So that's one-third here. One-third, if it's a guess, you got one-third of a chance to get it right. Alright, so let's go through this real quick here. We know a little bit about the structure of a carbocation, so this is a secondary alcohol under these conditions. The alcohol leaves, we form a carbocation, and we do SN1. Structure of a carbocation, well gosh, the carbon of the carbocation, and all the three atoms attached are all in the same plane. Hydrogen goes back. Here we have a methyl. Alright, so these guys are all in the same plane. Not every single atom there, but all of these groups, this carbon, which is the carbocation, this carbon, that hydrogen, and this carbon are all in the same plane. So now think about the next step in this reaction, and what kind of stereochemistry you'll get. We'll talk more about this on Friday.
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This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: 00:11 - Elimination Reactions of Alcohols: Dehydration 08:02 - Carbocation Rearrangement 24:12 - Conversion of Alcohols to Alkyl Halides with H-X
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10.5446/21628 (DOI)
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I need to finish chapter 9 today. Yes. Our exam is going to be on chapter 8 and 9. I need to finish chapter 9, so I'll be asking for less questions today. So if you have questions, you can come and ask me after class. I really need to finish chapter 9. Otherwise, we're digging a really deep hole for ourselves when it comes towards the end of class. So that's what I want to do today. We're going to get started. Everybody knows we have a midterm on Friday, yes? All right. So we left off last time talking about making tosalates in order to turn an alcohol into a good leaving group. Once you make a tosalate, then you can react it with any of the nucleophiles we talked about in chapter 7. So examples of common good nucleophiles would be N3 minus cyanide, iodide, bromide, HS minus. All right. So why is a sulfonate? And I'm such a good leaving group. Good leaving groups are weak bases, right? Good leaving groups are weak bases. PKA of the conjugate acid. What's the conjugate acid? Tocic acid. TSOH. We talked about that at the beginning of this chapter. It is minus 2.8. All right. So we know it's a good leaving group. And one of the reasons why it's a good leaving group is it is highly resonance stabilized. So I have all of the resonance structures drawn here. And so it's resonance stabilized. And we also have the negative charge delocalized over three atoms. All right. So we can make a tosalate. We can treat it with any of the nucleophiles that we talked about in chapter 7. The other thing we can do is we can treat it with one of the halogens. And we can make an alkyl halide that way in a two-step process. So this is what it would look like. I'm going to just draw this five-membered ring on its side. That's looking really ugly there, but you've got the idea. And then so then when we make a tosalate, we have retention of configuration. So we have our hydroxyl up. That means our tosalate is up. So we're going to write o-tosal, o-tos, to abbreviate that. And then when we do sodium bromide, that's going to be an SN2, therefore inversion. And when we do that, we get overall inversion of configuration. So we can make alkyl halides this way via tosalates. Just another reaction to put in our arsenal here of reactions. We're going to actually start cataloging reactions in chapter 10. We're not going to do it yet. But we will need to do it starting in chapter 10. We'll talk about that when the time comes. All right, so let's summarize. Alcohols can be converted into alkyl halides with HBr, HCl, HI, or thionicloride pyridine, or PBr3 pyridine. In addition, an alcohol can be converted into a tosalate, then treated with bromide, chloride, or iodide to convert it into an alkyl halide. We have a lot of different methods here. And these methods are complementary. So it's important that we have more than one. Once you have an alkyl halide or tosalate, you can do all of the substitution and elimination reactions seen in chapter 7 and 8. So we really aren't limited to halides. We can actually have tosalates. And we can do eliminations from chapter 8. We can do substitutions from chapter 7. Here's what you can't do what a lot of people try to do on the test, which will not work. A lot of people say, well, why do I have to memorize all of these ways of converting an alcohol into an alkyl halide or a tosalate? Why don't I just treat it with acid, protonate the alcohol, make it a good leaving group? So this is what some people try to do. And we're going to draw what you're thinking. And then we're going to say why that doesn't work. So if you're feeling very clever about this idea, I don't have to memorize all the stuff. I can just use this. And so let me draw the product. It seems reasonable. This would be the idea here. But that actually doesn't work. So we're going to put a big x through that. A green x through that. Yeah. This is what's going to happen instead. Here's our n3 minus. It's going to deprotonate. So what you end up getting instead is your alcohol back again. Oops, didn't want that. And then Hn3, hydrazoic acid. That's what you'll end up getting. So why doesn't that work? Why does that work with HBr? The reason that that works with HBr is because when you protonate the alcohol with HBr, you're left with bromide ion, which is an extremely weak base. And it's also a really good nucleophile. So the bromide comes in and does backside attack and kicks off water. N3 minus is not an extremely weak base. The pKa of the conjugate acid is 4.3. So it's just too strong of a base to do what we want it to do, which is substitution, when the fastest of all reactions are acid-base reactions. And so that's why that doesn't work. So make sure you don't try this strategy. There's also a sapling problem that asks the same question. And so take note of that. I've put that on test before because it's a really common mistake that students make. All right. So the last thing we want to talk about in this chapter is ethers. We're going to talk about regular ethers, and then we're going to talk about epoxides. So there's two mechanisms for epoxides that could potentially be on the test. And I typically ask both of them. There's an acid-catalyzed reaction, and then there's a base-catalyzed. And I typically ask both of them because those are reactions that prepare you well for reactions that are coming up. And so that's why I do that. All right. So ethers like hydrocarbons are remarkably inert to most chemical reactions. This is why they make such good solvents. So here's some common solvents. You've probably used diethyl ether in lab already, haven't you? Yes? Tetrahydrofuran is another one we'll see a lot in chapter 10. Tetrahydropyran, not as frequently in 1,4-dioxane. You might have heard of that. We're not going to use that too much. We mostly are going to use diethyl ether. But the thing that we like about a solvent is we don't want the solvent to react with our compounds. So these are really very, very stable compounds. Ethers are however cleaved when heated with hot, concentrated HI or HBR, these are the only ones that I'm going to use here. All right. And so let me give you an example here. If we take this ether, tert-butyl on one side, tert-butyl methyl ether, and we treat it with HI, one equivalent of hydriotic acid. So when I say one equivalent, I mean a 1 to 1 ratio between the HI and the ether. And if we do that, we get two products. We cleave the ether. We break it into two pieces. If we use one equivalent of HI, we get an iodide and an alcohol. If we continue to react it, if we add a second equivalent of hydriotic acid, this alcohol that we just made is converted into methyl iodide. The first form product will stay exactly the same. So we'll still get this. But the alcohol will be converted into an iodide. So we'll end up getting two things, that plus that. All right, let's look at the mechanism, and then we'll talk about how we figure out, if we just use one equivalent, how do we figure out which one is the iodide and which one is the alcohol? So we're going to do a stepwise method for figuring that out. First, let me give you the mechanism. The first step is protonation. I mean, already you're starting to see that protonation, what we learned, the mechanism we learned back in chapter two is used so frequently. We use it over and over again, and we will continue to do that throughout the whole year of organic chemistry. So arrow comes from the lone pair on oxygen. We grab the hydrogen. We break the hydrogen iodine bond. All right, so what this is looking very similar to is when we protonate an alcohol, right? So if this methyl on the right-hand side here was a hydrogen, that looks exactly like when we protonate an alcohol. So the only difference is that now we have a methyl there instead. The second step is going to be, and we've seen this over and over again in this chapter, SN1 or SN2 depending on the substrate. So that's the decision we're going to have to make. So these are the two considerations here. How we decide. If departure of a leaving group gives a secondary or tertiary carbocation or a resident stabilized carbocation, then a secondary or tertiary carbocation or a resident stabilized carbocation will form first. That's what you have to remember. So if we can make a secondary, a tertiary, or one of those resident stabilized carbocations, that's the first thing that's going to happen. And therefore, if we form a carbocation first, then that means it's in SN1. SN1 will be the fastest. Second consideration, so if we don't have that, if we can't form a secondary or tertiary or stabilized carbocation, if we form an unstable carbocation, like a methyl, vinyl, aryl, or unstabilized primary, then a carbocation will not form. The halide ion will attack the least hindered side. So therefore, SN2 will be the fastest. All right, so let's look on the next page and see if we can do this. All right, so I'm going to go through this process with this substrate here. Isopropyl on the left-hand side, ethyl on the right. Let's go through the process. First step, HBr, reprotonate. You will only see this with hydrobomic acid and hydriotic acid because these are extremely, extremely strong acids. All right, what was that? What? Oh, it's HI. OK, well, yeah, let's fix that. I don't know why I said HBr. I always use HI anyway. OK, so here's our decision-making point. First step is easy. Reprotonate the oxygen. And what we're doing is we're actually making it a better leaving group. All right, so it looks like on the left-hand side, we have an isopropyl group. And so if we break that carbon-oxygen bond, we can form a secondary carbocation. That's going to be fastest. We can form a secondary carbocation. So then what's going to happen is this group is going to leave. Boom, just like that, that leaves us with an isopropyl carbocation, secondary carbocation. We always have to be alerted when we make a carbocation for rearrangements. Can that rearrange to anything? No. So we don't have to worry about it in this case. We get that plus the other side is ethanol. So I'll just draw that. And then what's going to happen next, the iodide that we just made. This is pretty much an extension of the HI reaction we talked about towards the beginning of this chapter. The iodide is going to come in and attack the carbocation. And then we get CH3 isopropyl iodide plus ethanol. See how we figured out which one is the alcohol and which one's the iodide by reasoning our way through the mechanism following the two guidelines. With a second equivalent of HI, the ethanol can now be converted, just like we did at the beginning of the chapter. Let's go through that one more time. That's a good review for us. HI, this is primary. So we know it's going to be an SN2. So you should know this mechanism like the back of your hand, right? Because that's a possible mechanism for this upcoming midterm. Just like that. And iodide being such a weak base is not going to want to deprotonate again. What it's going to want to do instead is do backside attack and kick off water. So that's how we get converted into the iodide. So if you use excess or two equivalents, you're going to get everything converted to an iodide that can be converted to an iodide. Here's a second example here. Example two, we have methyl and ethyl on each side. Let's go through the process again. Can we form a secondary tertiary or resin and stabilize carbocation? No, that means we're going to do an SN2. OK, so let's draw our protonated ether. OK, so no good carbocation. No good carbocation. No good carbocation. Therefore, we're going to get an SN2. What side is the iodide going to attack on? Least hindered side, right? It's an SN2. Iodide's going to attack on the least hindered side. And that's the methyl. Backside attack, great carbon-oxygen bond. So we get those are the two products. We get if we use one equivalent of hydroiodic acid. If we use a second equivalent, then that means we're going to convert the ethanol to ethyl iodide, just like we did right here. So make sure that that's the thought process. This requires a lot of thought process here. We have attack at least substituted side. I want to say that. And I also want to go back up here and make a little note about watch for carbocation rearrangements. And that's what we're going to do any time we make a carbocation, especially a secondary one. All right, so in order to cleave an ether which is so stable, we could use it as a solvent most of the time. We have to use hydroiodic acid, hydrobromic acid. We have to heat it up pretty high to do this. If we have an ether that's in a three-membered ring, of course, which we call an epoxide, this reaction happens readily at room temperature. Why would that be? It's a really strange ring, right? It wants to open back up again. So it's much more reactive. This is 0 degrees centigrade. And let me draw you the two products we get, and then we're going to talk a little bit more about this mechanism. So epoxide mechanisms are going to help you with chapter 10. And epoxide mechanisms are going to help you with a large amount of content in 51C. And that's why I emphasize them. And that's why you're likely to see one of each of the two types we're doing here on this upcoming midterm. All right, so we have this. Oh, I drew that one wrong. Let me fix that. So we're also going to see some stereochemistry when we're opening up these epoxides. So you will see stereochemistry in these types of problems. And that's going to be really important that you show the right stereochemistry when you're doing reactions with epoxides. So I'll just give you a little warning ahead of time for that. We will be working on problems like this in discussion this week. So really good idea to go to this discussion this week and to prepare for the midterm. Because everything that's in the discussion worksheet is potential material for this midterm. All right, so these guys, by the way, are enantiomers. All right, so let's see what the mechanism looks like. This is going to be our acid catalyzed mechanism, which is a mechanism of a certain type that would be on the midterm, an acid catalyzed ring opening of an epoxide. The first step is the same first step that we've been doing every time we have HBr or HI. We protonate the oxygen. All right, so and then we do that. When we protonate first, that's the fastest reaction that occurs first. Acid-base reactions are extremely fast. And that also has a bonus in that it protonates to make the oxygen a better leaving group. So just like that. And then what happens is the bromide that we just liberated, this is our conjugate base, comes in and does backside attack. It can attack on either side. Both sides are equally substituted. As we're going to see, when they're not equally substituted, it doesn't attack on both sides. But in this case, it does attack on either side equally. So let's have it attack on the left-hand side, just like that. And it's backside attack, therefore, inversion of configuration. So what's going to happen is just like we did inversion in chapter 7, we move these groups up a little, but they still stay in the same orientation. And the inversion happens when the nucleophilic comes in on the opposite side of the leaving group. That's where we get our inversion. So let's draw the product there. And I usually draw the incoming nucleophile and the oxygen in the plane. It was a little easier to see here. On the right-hand side, we are not attacking the right-hand side. So those groups are going to be in the same spot here. On the left-hand side, we attack the bromides opposite the leaving group. So I'm just moving this hydrogen up a little bit. I'm moving the methyl up a little bit, but they still have the same orientation. So just like that. I'll just use, I didn't leave enough room for CH3. I'll just write ME. ME is a good abbreviation for methyl that you can use. Feel free to use that on the test. All right, so that's one possibility. The other possibility is for the bromide to attack on the right-hand side. So let's try that. So we're going to attack on the right-hand side, kick electrons up onto oxygen. The hydrogen moves up. Inversion, the methyl moves up, but they still keep their same orientation. So now, here's what it looks like here. This is the other enantiomer. So we move the hydrogen up a little bit. We move the methyl up, but they're still in the same orientation. On the left-hand side, we keep the groups exactly the same way that they are, because we haven't attacked that carbon. There is no inversion on the left-hand side. So it looks like that. And these guys are a pair of enantiomers. And it turns out that once you protonate an epoxide, it's so reactive that you can attack it even with weak nucleophiles. Bromides is a good nucleophile, but you could attack with water and alcohol, and you will open up easily. So let's look at some examples of that. So strong acid catalysis plus water. So I usually write H3O plus, because if I take a strong acid catalyst like sulfuric acid and I put it into water, what does it do? What does a strong acid do? Essentially, it completely dissociates. So our main thing here is H3O plus. So I often use H3O plus in my mechanisms when we have a strong acid catalyst in water. And this is what it looks like. I'm going to draw you the product, and we will show you the mechanism coming up. I'm going to write plus enantiomer. So basically, the way that I handle that, when we have a pair of enantiomers formed, when I first start testing on it, I want you to actually draw the enantiomer. And then after that, you graduate, and you can write plus E. But for this first test, if there's a pair of enantiomers formed, I want you to show both of them. Because I want to make sure that everybody knows how to draw a pair of enantiomers, because not everybody in this room knows how to do that. So I want to be able to make sure that you can do that first. So this reaction here, we're going to go through the mechanisms here. Same mechanism as above, except that water attacks instead of bromide. And you could also do a strong acid catalyst with an alcohol. And this is what it would look like. We're going to draw plus C. And then again, we're going to eventually, in one way or another, we're going to show the mechanism to both of these, for both of these reactions. Either in the way we do this is we do it either here, or we do it in discussion. So any mechanism that you see here in class or in discussion is possible test material. It's kind of the way I roll here on that sort of thing. So we have this plus enantiomer. And then same mechanism as above. So I'll just do ditto marks, except methanol attacks instead of water. All right, so what does the acid do? The acid catalyzes the reaction because it protonates the epoxide, which makes it a better leaving group, which makes it very easy for nucleophiles to attack and open up the ring. And this is especially important when the nucleophiles are weak nucleophiles, such as an alcohol or water. All right, so we said that this was a symmetrical epoxide. We can have attack on either side. Let's see what happens. And you might be surprised about this. If we have an unsymmetrical epoxide. So I didn't bring my laser pointer still in my car. So let's talk about this. Do you see on the left-hand side, we have an ethyl and a methyl. It's more substituted on the left-hand side. On the right-hand side, we have just a methyl. So let's see what happens here. OK, so we're going to start off with optically pure single enantiomer. All right, what do we get? Here's our product. And we're going to go through how we get that. Only one product, single product, we do not get a pair of enantiomers here. We do not get the enantiomer. And so I'm going to draw it. And then we're going to, and that's not even the enantiomer, is it? What would we call this product? We're the bromide attacks on the opposite side. Are they enantiomers? We have actually different connectivity here, so these are not even enantiomers. We call them actually regioisomers. All right, so that means that in one side, when the first product we attack on the left-hand side and the second product we attack on the right-hand side, we don't get any of the second product. So let's put a big X through that. We don't get any of that. There are what we call two possible regioisomers. But only one is formed. So we call that a regioselective reaction. And it turns out, what side is the nucleophile attacking on here? Most substituted or least substituted? It's attacking on the most substituted side. Nucleophile only attacks at the most substituted side. That doesn't sound like an SN2 reaction, does it? If it was an SN2, a pure SN2, we did get inversion of configuration, and it was backside attack. But certainly, if it was an SN2 reaction, we wouldn't get attack on the most substituted side. So some things amiss here. This is not exactly what we would expect. Same goes for other acid-catalyzed epoxide ring reactions. Again, if we start with a single enantiomer, as long as it is unsymmetrical, we only get one regioisomer. So we'd have methanol come in here. And you can see the methanol is just taking the exact place that the bromine takes. Everything else that we draw is going to match the top red drawing exactly, except that now instead of the bromide, we have methanol. So we have only one regioisomer. So the question is, why is that happening? There is an explanation in your book where they talk about the transition states for the two possible regioisomers. And so what I did a couple years ago was I went through the explanation the way the book explains it. And then I went through this explanation, which is an alternative explanation, that I'm going to show you. And I took a show of hands to see who liked which explanation better. And most students liked this explanation. It was overwhelming. So I'm doing a different explanation from the book for this. This is not something I will ask you to explain on the test. It's too complicated. But if this doesn't make sense to you, look at the explanation in the book. And if that makes more sense to you, then go with that. It doesn't matter which way you choose. So here's an explanation that most students find a little bit easier than looking at the structure of the transition states. And so the explanation is, bonding in the protonated epoxide is unsymmetrical with the more highly substituted carbon bearing considerable partial positive charge. The nucleophile attacks this carbon even though it is more highly substituted. That doesn't sound like it's easy to understand at all. So let's go through this. So what I'm going to do is I'm going to take this protonated epoxide. Let's protonate it here. We'll skip that step. And I'm going to draw resonance structures. So now remember, the rules for resonance structures, we're going to be doing something a little unusual here. But the rules for resonance structures are, atoms stay where they are, you move around electrons. We don't commonly break a sigma bond in a resonance structure, but that's allowed as long as we are just moving electrons and not atoms. So I'm going to be drawing three. So here's the first resonance structure right here. After protonation, there's our first resonance structure. And then what we can do is we can go here and we can break this sigma bond again as long. It's weird looking, but as long as we are not moving atoms, we are moving electrons, that's OK. If we do that, we get a tertiary carbocation as a resonance structure. If we move it the other way, so I'll use a different color for that, if we break the bond this way, then that gives us a secondary carbocation. What's better, a tertiary or a secondary? It's a tertiary carbocation is better. And so this one, of course, is the best resonance structure, but this is the second best. They're both very minor, but it's the second best. And if we look at the hybrid, and what I'm going to do is I'm going to draw a hybrid of just the first two resonance structures. I'm going to leave out the second one. I'm going to do just a hybrid of the first two, and then you can kind of see where this is coming from. So here's my hybrid here. So I'm dotting this bond here. So that bond, and it turns out that bond is going to start lengthening in the transition state anyway, because we have very high degree of ring string. And so if that bond lengthens a little, the one that I have dotted, that's going to relieve some ring strain over on the right-hand side. And so that's going to be happening. Here's my methyl here. And I'm just going to do a hybrid of the first two, so that means I have a partial positive here, because I have a positive on oxygen in the first one, none on oxygen in the second, and the carbon on the left has partial positive. And so it turns out that the nucleophile is going to want to come in and attack the side that's the most electron deficient. So the nucleophile attacks the side that is most electron deficient. And that's going to be the left-hand side, because that makes a more stable carbocation as a resonance structure. That's the most electrophilic carbon. So that means that this bromide is going to come in. It's going to go here. And we break that bond here. And so that's why we get the only product where the bromide attacks on the most substituted side. So this is kind of a strange mechanism, because it's part SN2 in that we get backside attack and inversion of configuration. And it's part SN1, because we are forming some partial positive charge on the carbon that would make the best carbocation, even though we're really not forming a complete carbocation. So it's kind of a mix of SN1 and SN2. It's the best way I have to explain it. So mix of SN1 and SN2. So if you're saying to yourself, why do we have to go through this big, long explanation that's complicated? I don't understand. Why can't we just have a regular carbocation form in this reaction? Why do we have to have a partial thing happening? Why can't we do this? So here's the why can't. What if? Why can't we just have a much more simple explanation? What if? So if a carbocation forms, then this is what the mechanism would look like. And let's see why this can't happen. Let's make a full-blown carbocation. Why have something weird bridging something weird thing? Why do we have to do that? Why can't we just make a carbocation? So let's see what that would look like. And then you're going to be able to tell me why we can't do this. That's CH3, ethyl. So we know what a carbocation looks like. If we make a carbocation, then that means that the bromide can come in from either side, right? So the bromide can come in here on the top. And that's the key here. The bromide can come in from the top. And the bromide can come in from the bottom. So what that amounts to is backside and frontside attack here. OK, so let's draw the two products that you would get if this is the case. Notice that the bromide is coming in on the same side as the leaving group, the hydroxyl. And if it comes in at the bottom, then we would get this product. Keep going back and forth with methyl ethyl, and methyl ME and then CH3. It's totally fine to do that, by the way. OK, if that happened, we would get two products. Do we get two products? We don't get two products. So that means that can't happen. We don't get any of this. We only get this. And that means the bromide cannot come in and attack on the opposite side there. And why can't it? And the reason it can't, if we look here at this structure right here, the reason it can't come in on that opposite side is that side is blocked by the oxygen, because that bond is still intact. That bond right here is still intact. So the bromide can't come in from this side. It has to come in from the opposite side. So there's our explanation. So if the intermediate was a carbocation, the nucleophile can attack from the top and the bottom, giving a mixture of stereoisomers. The stereochemistry of the product clearly shows the attack of the nucleophile only on the bottom face of the epoxide. The intermediate must there be more like a protonated epoxide than a planar carbocation. All right, so this is what I wanted to look like. You're going to show the protonation step. If I have this mechanism on the test, you do not need to draw all those resonance structures. You do not need to draw the hybrid. All you do is you protonate the epoxide, and you go like this. Boom. So it's a simple two-step mechanism here. We move the ethyl up. We move the methyl up. We still keep the same orientation. And then on the right-hand side, hydrogen stays, methyl stays. So only backside attack is observed. Only backside attack. And so therefore, it can't be a carbocation intermediate. All right, so here's the thing I just got through saying. I don't expect you to draw the resonance structures. I don't expect you to draw the hybrid. This is a sample test question. You might see this exact test question on your test, or maybe something so similar that you think it's exactly the exact test question. Very high likelihood of that. So that's going to be free points on the test, right? OK, so let's look at that. So sample question. Predict the product for the following reaction and provide a mechanism for its formation. Show all lone pairs, charges, and curvy arrows. Do not combine two steps into one. So let's do this. Now I can write H2SO4, or I can write H3O plus catalytic. Doesn't matter. Let's do it with what we have right here. We're going to protonate oxygen first. Arrow comes from the lone pair on oxygen, grabs the hydrogen, we break the hydrogen-oxygen bond. All right, so far so good. So that means no one's going to miss this problem on the test, right? Because you know exactly, it should look just like I'm doing here. Methanol attacks. Do we deprotonate methanol? No. We don't deprotonate the methanol. Methoxide ion is not going to appear in an acid catalyzed mechanism. What we are going to do is attack with oxygen on the most substituted side. It's protonated, sorry. Yes. Did not protonate that. Need to do that. I'm trying to show you what you not do. Gosh. OK, we're good. I was just going to catch that when I'm drawing the product here. OK, so that looks like that. We need a positive charge here also, don't we? Positive charge. So boom, this should be OH here. We have our protonated methanol. What's the last step here? What would be the last step here? I'm showing stereochemistry. I'm moving this methyl up. I'm moving the methyl up, but they still are in the same orientation. Last step is to deprotonate the methanol that just attacked. And I can use other methanol that's in the reaction mixture. This is used as a solvent. Or if you prefer, you can use the conjugate base of sulfuric acid. So both of those would be OK to use as bases to deprotonate. And then we only show one product here. CH3, we're good. All right, oh my gosh, we've got three minutes here. Let's see what we can do in three minutes. Don't worry, this part's easy. OK. Acid catalyzed mechanism, we got it down, right? This is base catalyzed or strong nucleophile? Strong nucleophile, right? So easy. This is pure SN2. Oh, that doesn't look like an N. Pure SN2. What happens? Methoxide comes in. What side does it attack on? Least substituted side, pure SN2. Boom. Can you do that? This is something that only happens with epoxides. You cannot do the equivalent reaction with ethers. Not in a million years. So this is something that only happens with epoxides. This is pure SN2, so it should be very straightforward for you. Here's our methyl here. And we only get one product. So nucleophile attacks on the least substituted side. Nucleophile attacks on least substituted side. If you tried to do the same thing with a regular ether, you would get no reaction. So when we have strong nucleophiles or base catalyzed, the nucleophile attacks first. We do not protonate the epoxide first. So this is what it looks like here. Let's go through the whole mechanism in the last minute because we're that good. OK? Look at that. Boom. This should be your easiest problem on the test. We're going to attack on the most substituted, least substituted side. We get O minus. Then what happens? What do we need to do to finish the reaction? We need to protonate oxygen, don't we? What do we protonate oxygen with? There's no acid present, so don't throw acid in there. What we're going to do is we're going to use methanol. And when we use methanol, you'll see we're actually regenerating our catalyst. So we only need a catalytic amount of methoxide ion. And there it is. Can you do that on the test coming up on Friday? I hope so. That would be amazing. Opposite regioselectivity, we're not going to worry about the alkoxide till Wednesday. And alkoxide is actually a leaving group. We'll explain that on Wednesday. But I do want you to know both of these mechanisms. We'll stop right there and we'll continue this next time.
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This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: 00:50 - Converting Alcohols into Sulfonate Esters 07:27 - Substitution Reactions of Ethers 19:07 - Reactions of Epoxides: Acid-Catalyzed Ring Opening 47:58 - Nucleophilic Ring Opening
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10.5446/21829 (DOI)
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I will talk about evaluation of BISAN training using 3D play game. There are six main things in my presentation. First, stereoscopic 3D, vision training, partiality test, experiment methods, research and discussion, and conclusion. Stereoscopic 3D contents are viewed in brain as views of two different images. It is quite a different visual mechanism from normal visual response in daily natural vision. Therefore, human factor analysis has been so far carried out on 3D images in various sectors and methods. This study aimed to examine the partiality of 3D images as vision training using accommodative partiality and versions partiality by 3D shooting game, which is more dynamically stimulating than ordinary 3D images. After vision evaluation, when a facet is diagnosed with a T-solder, vision training precedes optical treatment using spectacled, prism spectacled and contact lens. Vision training is divided into play optics for envelopia and orthotics for telephoria. After presentation, I will show you some video about vision training and therapy. In optometry, good vision and comfortable vision are strictly distinguished. If amotropia facet has deviation, it can be a treatment to low vision with change of lens and correction, correct deviation, even though facet has full vision correction by optical methods. As a research, such techniques are widely used in vision training, clinics around the world, and their high effectiveness has been noticed in many research. In particular, children have a problem with VT treatment for vinyl killer disorder, mainly due to the lack of motivation, inducement and concentration. Therefore, it is difficult for them to achieve target-level treatment. It implies that there is an expectation or potential possibility to raise the outcome of the treatment if VT is equipped with device that can attract children's attention and interest in the problem. Normal visual function is important in learning efficiency. Pursuit test is divided into accommodative partially test and version partially test. Accommodative partially test is the examining function of crystal lens and version partially test is the examining version's efficiency of eye. Accommodative partially test measures the accommodative accuracy and speed and monocular or vinyl killer, reviewed distance respectively. Particularly, because the test can obtain information about the disturbance in accommodation of facet, it is often used in clinical setting. Besides the number of psychopharmemnit, response state and speed of vision clarity that appear on each lens are also important factors. Version partially test measures the flexibility of a facet eye. It tests the version's ability of an eye to fuse when different eye positions change fast. Version partially test is to measure the flexibility of versions by based on prism that induce convergence of eye and basing prism that induce the versions. This is information of research object. They were university student total 30 person. Average age is 24.53. They were without particular occured disease or systemic disease, corrected visual occurity of more than 0.8. Before playing game, their visual occurity were corrected with basing manifest reflection, user photo. First, they were measured for partiality after playing 2D action game and took rest for 30 minutes. In second section, they were measured for partiality after playing 3D action game. They played shooting action game Q-Jon 3, which is one of three games. Playtime is 30 minutes, 2D and 3D respectively. Play distance is 1 meter. This is accommodative partiality change after playing 2D and 3D games. This table is comparison three groups, Bepoil 2D, Bepoil 3D, 2D and 3D. There were statistical significance. Next is version's partiality change after playing 2D and 3D game. This table also comparison three groups, Bepoil 2D, Bepoil 3D, 2D and 3D. There were also statistical significance. It can be explained why playing game. Eyes are stimulated with the stereoscopic image and brightness change so that people remain on the persistence stimulation. Because of this, the depth of a focus changes reversible and researching beauty. It is assumed that 3D game has some greater impact because it even adds future accommodation. Version's partiality also shows similar tendency as accommodative partiality. That is, version's eye movement keeps happening at a fixed distance of playing game in the process of fusion visual images, which has more direct impact of the data of version's partiality. The recent studies of a video game is beneficial for visual function, for example contrast sensitivity, visual field and special visual attention. It is all relative of attribute to the potentiality of brain-fluxed CT. Action video game stimulates overall part of brain, requiring multitasking and speed. Video game encourages players to repeat visual and auditory stimulation. It can be helpful even for the treatment of dyslexia. Daphnaya-Babelia announced that action video game can change the way for brain to process visual information and for a human's visual system to the fullest, while a brain adjusts itself to such stimulation and changes. The most important element of successivity in clinical settings is visual-related to clinic and relative to training. Motivation and interest have impact in training. Data of partiality is important in that indicate the quality of daily visual life. In general, partiality test is utilized in clinic settings as guideline for the treatment of functional disorder of ocular accommodation and versions. Most of the studies regarding 3D content, the beneficial aspect of 3D images have not been much approached in research. I hope that studies on the positive functions of 3D images will continue on the improvement of visual function as medical content. I would like to 5 exercise on relative to vision training and trapping. The first exercise is a practical embolopia. The number from 1 to 12 will show on clockwise 5 missing number from bottom of the screen. The correct answer is 6. 3.0. Normal ocular visual stimulus is about 60 to 70%. Embolopia visual stimulus is about 30 to 40%. Given suitable for training to normal vision about more than 0.8, the correct answer is 0.2 or 3. The next exercise is improvement. Follow the arrow and find which letter did the arrow reach. So which letter is the answer? It's Korean text is G. This is training program for young child improve of monocular eye movement and interactive to retina or cerebral cortex. Especially young children are very sensitive to hearing the sound. The teaching sounds experiment is important to you for maximize visual stimulus. The third exercise is vision training using persup. It is future training of horizontal and cyclotropia. You can wear red green filter or green filter for right eye and red filter for left eye. Follow the line start with the number 1. Try to say number as you follow the line. In additional you can do this exercise while you are walking into place, moving around and set happen. This is dark room test. The fourth exercise is also eye movement using persup. Remember the order in which the numbers are going in the hole as by tracking the number from hammer. It's low level. Step up and get the number is increased the faster the speed. The last exercise is practice for embolopia using binocular library. After polarizing spectacles wear to embolopia has to wear the same axis polarizing spectacles range. The change may occur in the clarity shown in the video. Visual stimulus to increase the amount of embolopia than normal ocular using polarizing film. And set the target with the degree of embolopia. This can be a binocular library when the embolopia is increased by more than 13 levels. It can stimulate state of six along with the highest level of visual ocularity. Generally, flip the embolopia than polarizing. Practitioners want visual stimulus may be better. Thank you for listening to my presentation.
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The present study aimed to examine the effect of the vision training, which is a benefit of watching 3D video images (3D video shooting game in this study), focusing on its accommodative facility and vergence facility. Both facilities, which are the scales used to measure human visual performance, are very important factors for man in leading comfortable and easy life. This study was conducted on 30 participants in their 20s through 30s (19 males and 11 females at 24.53 ± 2.94 years), who can watch 3D video images and play 3D game. Their accommodative and vergence facility were measured before and after they watched 2D and 3D game. It turned out that their accommodative facility improved after they played both 2D and 3D games and more improved right after they played 3D game than 2D game. Likewise, their vergence facility was proved to improve after they played both 2D and 3D games and more improved soon after they played 3D game than 2D game. In addition, it was demonstrated that their accommodative facility improved to greater extent than their vergence facility. While studies have been so far conducted on the adverse effects of 3D contents, from the perspective of human factor, on the imbalance of visual accommodation and convergence, the present study is expected to broaden the applicable scope of 3D contents by utilizing the visual benefit of 3D contents for vision training. © (2015) COPYRIGHT Society of Photo-Optical Instrumentation Engineers (SPIE).
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10.5446/21815 (DOI)
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Hello, everybody, and thank you for coming to this presentation. So I will present a paper on objective method for stereoscopic 3D quality prediction using visual annoyance and acceptability. So visual discomfort can be introduced at every stage of the broadcast chain from production to visualization. At the stage of production, geometrical color luminance can be produced to mismatch between two cameras. 2D distortion resulting in view asymmetries can be produced to coding auto-smission. Finally, at the stage of visualization, virgins accommodation conflicts can be produced. It's very important to understand that discomfort produced due to view asymmetry of virgins accommodation conflicts is the result of the violation of psychological mechanism of binocular vision. So for example, in case of severe asymmetries, all viewer will suffer from visual discomfort because brain doesn't manage successfully process discrepancies between left and right views. Hence, we formulate a minimum requirement for any stereoscopic 3D system is to guarantee certain level of visual comfort to all customers. The context of this today, we want to consider interest of orange 3D services because most of the content they leave for broadcasting content view asymmetry that induce visual discomfort. So for orange services, it's very important to have complaints of the clients and then improve the service quality. Also, it's motivating to control quality of the produce content for the post-production. So the first objective was to develop an approach for objective modeling stereoscopic 3D system, quality of experience that's all are connecting the technical parameters to 3D viewing experience. And the second is to propose a new objective metric which will guarantee a certain level of visual comfort for the customers. Due to sensation of enough depth and eventually occur discomfort, stereoscopic content can be not evaluating using the standard 2D quality concepts. Instead, quality of experience is used in recommendation of ITU BT2021 defines three perceptual attributes that collectively affect on quality of experience. They are picture quality, depth quality and visual comfort. However, to our opinion, depth quality doesn't reflect such artifacts as cardboard effects and puppet theater effects. So to consider shape distortion, we are reflect as a witness factor in cinematography. We propose to use 3D geometry called distortion as basic property attribute. These perceptual attributes should be connected with tangible aspect of viewing experience or show objective quality factor. So in the case of picture quality, we have spatial, temporal and spatial temporal distortion. In case of 3D geometrical distortion can be perceived as magnification, minaturization in case in planar direction or compression or stretching in case of cardboard effects. And finally, visual comfort can be experienced as visual annoyance and visual fatigue. Weicheng has demonstrated in his 2Di that visual comfort is the most important axis if there is this comfort. So we think it will be reasonable to focus on this axis when designing objective metric. Also, taking an account the minimum requirement I have talked in the beginning of this presentation is to guarantee visual comfort to consumers. Visual fatigue is a long-term indicator. In this work, it's only used little sequences, so visual fatigue will not take account. So next step in this work is try to link visual annoyance or subjective quality factor to technical parameters provoking visual discomfort. Here you have a list of technical parameters considering as evoking visual annoyance in stereoscopic 3D. Then, visual will measure with dedicated algorithms. The question is how measure distortion level can be characterized objectively and linked to viewer perceptions? So it's decided to use a simple ID with three colors which often used in quality monitoring tools. So here these three colors are green, no problem, orange, attention, red, not acceptable. This category must be linked to viewer perception especially to the sensation of visual discomfort. But the question is what does define boundaries between these categories? So the first boundary is between annoying and not annoying and define the annoying result. How these categories are linked to technical parameters? In first time, our categories are drawn horizontally. Next to it, we'll draw distortion axis of technical quality parameters. So here we can see each category represents a range of distortion level. This range is limited by perceptual result, annoyance result and acceptability result. By transcending an annoyance result, change category from green to orange. By transcending acceptability result from orange to red. Visual result represents distortion level of technical parameter Px, for example, number of pixel or vertical shift of rotation degrees. It may be practical to adapt the level of acceptability in the context of marketing or services requirement. For example, in this case, 80% of acceptability may be a criteria for orange to decide whether buy or not buy a movie for the broadcasting. By adapting the level of acceptability, we can see we have a distortion range of category red. So how to define the boundary between objective categories? So how to define acceptability and annoyance results? For this, we design a subjective color scale. We contain same category colors, green, orange and red, associate with perceptual scales. On these scales, 0.5 corresponds to 50% of acceptability result. 1.5 defines 50% of annoyance result. Advantages of this scale in comparison with the states of the arts that both results are estimated in the same time and direct relation with objective category. So in the same scale, we have objective prediction that can be evaluated via subjective experiment. After the list of technical parameters was defined, we have to detect them. By the detection, I want to say what we are looking for. For example, in our case, US symmetry induces visual discomfort. These technical parameters should be measured with some dedicated algorithm or software. Measure with an algorithm distortion level. Should be compared with correspondent acceptability and annoyance results. Thus, perceptual results should be defined as a subjective experiment using color scale. Results should be defined one for all technical parameters. Then they can be stored in a database. Also, it's preferable that database stores results with different acceptability and annoyance level. We saw that to adapt objective prediction to different demands, for example, marketing or service requirement. So when this is accomplished, perceptual results can be compared to distortion level. So when input parameters are ready, free messages can be displayed during monitoring. So the first is no annoying green. This means that measure distortion level is less than annoyance result. Orange annoying. That means that distortion level is between the two perceptual results. And red unacceptable. This means that measure distortion level is greater than acceptability result. To estimate perceptual result, we use free send with different disparity levels. Some big protocol wise use with color scale to evaluate perceptual result of five view asymmetries. White level, green level, vertical disparity, rotation and magnification. So in this example of result for focal asymmetry, the X axis represents distortion level. The Y axis represents the mean opinion score collected with color scale for corresponding distortion level. Following the recommendation of ITU-BT500, asymmetry logistic function was used to approximate continuous relationship the perceptual result we obtained using this relationship. So here are resulting results for focal mismatch. And here are the results obtained for all other asymmetries. Their results have a boundary of objective categories. Next, this plot allows to compare subjective results with objective prediction. So this is the example of result for green asymmetry. X axis represents distortion level. X axis represents mean opinion score obtained with color scale. Subjective category are defined in accordance with the color scale design. Thus directly from graph, we can read resulting category from subjective test in the following way. For example, in the test basketball send we save this score for different distortion level. objective prediction can be read following the design of objective categories. So the boundaries of objective categories are vertical lines representing acceptability and anion's result for green asymmetry, which were calculated as average of free sense. So predict category can be read from the plot like this. So objective results for basketball send are here. To investigate the performance of the metric, we calculated person correlation coefficient between subjective votes and objective prediction. For all send, for green asymmetry, it's pretty eight. Intersection of objective category create color rectangle. When mean opinion score is located outside of triangle, this mean that objective prediction has not much subjective result like here in this example. The correlation coefficient calculated between subjective result and objective for five views, asymmetry and free sense. From result, we can see that objective prediction are correlated very well with subjective result with minimum of 0.88 for rotation asymmetry. The season of flow correlation was that we used two descents. When one of the view was rotated, it create false disparity, which is very easy to notice. For now, we use 50% of result of acceptability and anion's. But how do we evaluate another levels? Due to design of color scale, it can be decomposed into scale. In the first, acceptability scale. The votes can be convert to acceptable and not acceptable. So in red, not acceptable. In green, acceptable. Further, it can be decomposed to anion's scales. In this case, in red, it's annoying. In green, not annoying. To follow usual shape of logistic function and its preferable to invert the data. Basically, such decomposition is data mapping from one to two data sets. As in previous example, continuous relationship can be approximated from this data set to evaluation of desired level of perceptual result. The question is, how do you acceptability and level change with color scale? To estimate this, color scale can be decomposed into anion's scales and acceptability scales. So in this case, when you have a score of 1.5 on color scales, it equal to 49% of anion's. When you have a score of 0.5 in color scales, it's 55% of acceptability. This result confirmed our initial hypothesis that 50% acceptability and anion's results can be approximated directly from the color scales. Another result is, when you have a score of 1 on color scales, 80% experience visual annoyance and 82% accept it. So in our case, acceptability is the acceptance of a certain visual annoyance level. So the mad percentage of annoyance and acceptability can be approximated into curves. These curves are convenient because the relationship between the color scale and acceptability and annoyance level can be easily found. Using this information, color scale can be adapted to new recolment field. For example, in this case, for 80% of acceptability and 50% of annoyance, this curve can be stored in the system to estimate the level of acceptability and annoyance and adjust the matrix. But can we use the conventional scales to obtain boundary of objective category for our metric? In order to answer this question, we decide to map through the obtained with impairment scale and acceptability scale. So when the score in acceptability scale is 0.8 is equal to 1.6 in color scales. So using this information to adapt color scale, we can see that orange category disappear. When it's 3.5 on impairment scale, it's equal to 1.2 in color scales. So in this case, it means that according to our results, an annoyance result on impaired scale represents not 50%, which one may expect, but 70% of visual annoyance. And to finish, when we have 0.5 on acceptability scale is equal to 3.5 on impairment scales. An annoyance result is equal to 50% of acceptability results, so if this result is used as boundary for our metric orange category, it disappears because they're equal. So to conclusion, it is the student who proposes objective metric to predict category associated with viewer perception by using perceptual results. For the perceptive is extend proposed color metric to another axis of stereoscopic 3D quality of experience or technology. Another perspective is a long duration study to investigate the impact of stereoscopic 3D quality of experience, acceptability or recurrence, duration and level of view asymmetry. Thank you for your attention and don't hesitate to ask supplementary question and information by writing an email to the hotel, Darya Kostova and Jerome Fournier. Thank you for your attention.
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This study proposes a new objective metric for video quality assessment. It predicts the impact of technical quality parameters relevant to visual discomfort on human perception. The proposed metric is based on a 3-level color scale: (1) Green - not annoying, (2) Orange - annoying but acceptable, (3) Red - not acceptable. Therefore, each color category reflects viewers' judgment based on stimulus acceptability and induced visual annoyance. The boundary between the “Green" and “Orange" categories defines the visual annoyance threshold, while the boundary between the “Orange" and “Red" categories defines the acceptability threshold. Once the technical quality parameters are measured, they are compared to perceptual thresholds. Such comparison allows estimating the quality of the 3D video sequence. Besides, the proposed metric is adjustable to service or production requirements by changing the percentage of acceptability and/or visual annoyance. The performance of the metric is evaluated in a subjective experiment that uses three stereoscopic scenes. Five view asymmetries with four degradation levels were introduced into initial test content. The results demonstrate high correlations between subjective scores and objective predictions for all view asymmetries. © (2015) COPYRIGHT Society of Photo-Optical Instrumentation Engineers (SPIE).
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10.5446/21821 (DOI)
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Thank you. Thank you. Good afternoon, everyone. Today my topic is load balancing multiple LCD light field display. Firstly, let me introduce what is a multiple LCD display. Multiple LCD layers are stacked which construct a special light modulator, and the light emitted from the backlight is modulated by the LCD layers. The light rays set produced by the LCD layers construct a light field. People in different populations will see different view images from different perspectives, then they can get a 3D effect. Compared to the previous 3D display technology like volumetric display and projector array and the nautical lens or integral imaging, multiple LCD displays require low mechanical motion and there is low image resolution noise. In addition, this technology can be implemented easily on the mobile devices. Well, there are two main disadvantages. The transmittance of LCD panel is very low, so more LCD layers will result in lower display brightness. And another challenge problem is how to decompose the huge retroglyte light field into limited LCD layers. In other words, we need to display the light field compressively. In this paper, we developed, we analyzed the performance of light field composition by casting the problem as an over-determined question set. And we found multiple LCD displays are working in the state of serous overload, so we developed multi-layer and multi-zone joint optimization strategy to solve this problem. And finally, we built a prototype to implement a real-time light field decomposition and display based on multi-portal GPU cores. Before introducing the light field display, let me give the definition of light field. Light field is an array of real images from different perspectives. And it should be noted that the number of real images is greatly larger than the number of LCD layers. That's why we call it a compressive display. Each light rays can be projected back to the all-LCD panels, and we can find the intersection point with each LCD panel. The light ray can be expressed by the production of the three intersection pixels values, and we can also express the light rays by the summation of the three intersection pixels in the same way that the light ray is made. And one real image is produced by all LCD layers, but different real images are a combination of different pixels. So we can get the layer images, then we put the layer image to the corresponding LCD panel and layer C, and the light can be modulated, then the light field can be reconstructed in front of the LCD screens. But the problem is that the light ray is not the best way to do the quality of the constructed light field. Well, to analyze the performance of light field composition, we build a sample direct but effective model to analyze the processing of the light ray. We also rearrange the high-dimension light field into a long vector, and we also rearrange the high- dimension light layers into a much shorter vector in the same way. Now the high-dimension light field and the high-dimension matrix, we think pixels in the LCD panels are controllable units, and we assume the target light field to the load need to be solved. Well, it's obviously an overload equation that each controllable unit is responsible to modulate multiple light rays. In this case, the light field is 7 by 7, and there are only three LCD layers. The load on one pixel is 16 light rays. In other words, it's difficult for one pixel to give consideration to all 16 light rays. So there are two strategies to solve this problem. The strategy one is to increase LCD layers, then we can get more controllable units. And the strategy two is to reduce the load by resolving the light field especially. We test the strategy one in two things, they call and they die. We keep the size of light field in constant 7 by 7, and the LCD layers increases. And we can see the display quality improved at the beginning from two layers to three layers. But after three layers, they increase LCD layers and make limited contribution to improve light field quality. And the computation time cost increases linearly with the LCD layers. And most importantly, they display brightly while decreasing considerably along with the increasing of LCD layers. This is a visualization of the composition. From the results, we can see the parallax is reconstructed successfully. But there is some ghost and blurring. Maybe you can see the age around the grain dice. There is some ghost around the age. And there is some blurring around the head of the car. Now let's pay attention to the strategy two, load-balanced composition. We use a directional backlight to replace the uniform backlight. The directional light rays are modulated by LCD layers and the targeted light rays is divided into multiple sub zones. And one time, there is only one sub zone is displayed. And all four sub zones are displayed in sequence. From the mathematical model, we can see in one time, only partial light field needed to be decomposed and displayed. So the load on the three LCD layers is reduced significantly. And in other words, the three LCD layers is working in the time multiplexing. And again, this strategy without requiring extra LCD layers, so they display brightly is keeping a high level. We also tested the strategy two in the same sense, the car and the dice. By the way, we keep the LCD layers in constant three layers and the size of light field decreases. For the results, we can see smaller light field size, a greater quality improvement for constant LCD layers and a computation time cost decreases by resolves in light field. In order to implement load balancing on GPUs, we developed an iterative algorithm to update the LCD layers. Our algorithm updates the LCD layers in updates of one layer at a one time and the rest of the layers keep fixed before finishing the updating constant layers. We minimize the errors between the target light rays and the reconstructed light rays. By deforestation, we can get the updated rulers for the first layers. We can see the updated pixels value is the production of the old pixel value and the weight factor. The weight factor depends on the target light rays and the reconstructed light rays before updating. Also depends on the LCD, also depends on the pixel values on other LCD layers. Similarly, we can get the updated rulers for the second and third layers. We use a 7 by 3 light field to test our load balancing, the composition algorithm. This is the original light field. We use two display cards, the model of display card is GeForce 6 lighting. One display card has two GPU cores, so we have four GPU cores. One GPU core is responsible to decompose subzone of the light field. The table shows the display quality and the time cost. From the results, we can see the display quality is generally above that 13 dB. And the time cost is 13 milliseconds and most. So the light field can be displayed and 13 frames per second. By comparison, the original light field and the reconstructed light field, we can see the parallax is reconstructed correctly. And the blurring and the ghost around the object is reduced. The left side is our prototype. The model of the LCD panel is ASU VG 278H. And this LCD panel can display the image and up to 144 frames per second. And we put the particular lens shed on the LCD panel which near the backlight source. The right side is the photograph of the prototype in the indoor lighting environment. And the bottom is the photograph of the prototype in the front of the LCD screen from different perspective. And we can say from different direction or from different position, we can get different images and the parallax is correct. According to the above discussion, we can conclude that the strategy of increasing LCD layers improve display quality slightly but at the price of greatly decreased display brightness. Our load balance optimization improve display quality without actual LCD layers. So the display brightness keep a high level in the indoor lighting environment. And another advantage of the load balance optimization is this strategy further explores the special independence of the light field. So we can implement the algorithm on multi GPUs. Thanks for your attention.
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We propose a load-balancing multi-LCD light field display technology. The multiple LCD panels operate as a spatial light modulator. Each light ray is the combination of pixels located in multiple LCD panels. The challenging problem is how to decompose the light field into limited layer images and display the light field compressively. Each pixel, as a controllable unit, is in spatial-multiplexing which means one pixel needs to be responsible to modulate multiple target light rays at the same time. We analyze the load imposed on each pixel by casting the light field decomposition as an over-determined equation problem. We found each pixel works in the state of overload and single pixel couldn’t give consideration to all target light rays. In order to reduce the load on pixels and improve display fidelity, we develop a multi-layer and multi-zone joint optimization strategy. The target light field is divided into multiple subzones and each subzone is displayed by multiple LCD panels combining with a dynamic directional backlight. By resolving the target light field, our display system further explores the multi-LCD’s capability of displaying light field and higher quality of light field display is achieved. We test our load-balancing decomposition algorithm based on different scene. The parallax, occlusion and blur of out-of-focus are restored successfully. And a three-layer prototype is constructed to demonstrate that correct light field is displayed in indoor lighting environment. © (2015) COPYRIGHT Society of Photo-Optical Instrumentation Engineers (SPIE).
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10.5446/21823 (DOI)
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So today, I'm going to be discussing viewing preferences for motion in depth in stereoscopic 3D film. So first, as I'm sure many of you are aware, within 2D film, if you're filming practices are not optimized and you add motion to that film, you're going to introduce the possibility of motion artifacts. So things like motion jutter and motion blur, which I illustrated here. But within 2D film, we have these well-established rules of thumb, where we know we can adjust a few parameters, such as focal length, shutter angle, and frame rate, and reduce these distortions in our final product. However, when we try to apply these rules to three-dimensional film, we run into the problem with the addition of binocular parallax. So when we're adding this new highly salient cut to depth to already natural scene, we're going to run the risk of mismatching this new depth cue with the already two-dimensional depth cues that exist within that natural scene. And this is, of course, what can lead to incomplete, ambiguous, or contradictory, percepts in your final product. So between the distortions from the mismatch of depth cues within 3D film, combined with the distortions we know can come from the addition of motion, applying these rules of thumb to 3D film can get very complex. So our most immediate solution to this problem is to very precisely allocate our depth budget when it comes to creating stereoscopic 3D content. However, the absence of general guidelines for the optimal creation of stereoscopic 3D film has left great debate in the literature surrounding what parameters are actually critical to creating the ideal viewing experience. And if we actually go back into that literature and look at different assessments of viewing experience, we can see the vast majority of these studies focus on factors that affect viewer comfort. So within these studies of viewer comfort, the general focus is on subjective measures of comfort. So using something like a rating scale or questionnaire to directly assess how comfortable viewers find a particular sequence. And I'm sure we're all looking forward to all the viewer comfort talks that precede my current talk. So with the general consensus within this literature, that we tend to get lower ratings of comfort in scenes that have either changes in binocular parallax or very excessive binocular parallax, or in scenes with high amounts of motion or very rapid motion. Now it's very important for us to understand how people respond to stereoscopic 3D content. However, within this literature, there's one dimension that has yet to be explored. And that is how these two factors affect a measure of viewer preferences. So within this current study, I set out to evaluate viewers aesthetic preferences for camera motion within stereoscopic 3D sequences in a theater viewing environment. And it was very important to do it within a theater viewing environment, not only to keep it similar to how people traditionally view 3D films, but we wanted to free ourselves from a lot of restrictions that come with experimental testing conditions such as reduced viewing distances. So because no previous study has actually assessed how these factors affect viewer comfort, we've actually based our previous predictions on measures of viewer comfort. So what we might predict is that we should see stronger preferences for slower camera speeds in depth and smaller interaxial distances. So for our current study, the stimuli that we actually use for filming can be seen on the right here. So we had a professional actor perform a six second dance phrase, and this dance phrase was filmed on a variety of different parameters. So here we have our two main parameters of interest, the effect of motion and the effect of binocular parallax. So for motion, we actually split it into two different components. So first, we had the direction of that motion. So we had two different conditions, the first being a z-axis motion condition. So this was a dolly shot towards the actor in depth, whereas our lateral motion condition was a tracking shot from the left side of the set to the right side of the set as the focus remained on our actor in the center. And of course, the second component of this motion was the speed of that motion. So we had three different conditions of low, medium, and high speed, which correspond to these speeds below in meters per second. And this is the speed of the camera along our dolly and track system. And of course, for binocular parallax, we manipulate the interaxial distance between our two cameras. So we had a zero, small, and large IA condition, which correspond to zero, 10, and 65 millimeters respectively. So this dance phrase was filmed under every combination of these parameters. So what we ended up with was 18 unique video clips or nine unique video clips for each direction of motion. And actually, right now, I have a couple examples of the stimuli that we used during our experiment, so if you can put on your polarized glasses. And if we can get the clips up. Good. Great. So what you're going to be seeing is the first two clips are an example of our Z-axis motion condition. So you'll see the fastest and the slowest speeds in that condition, followed by our two lateral motion conditions. And just as you're viewing those, I just want you to be aware that we did have other objects in the scene besides just our actor in the middle. So we did have two other students see the different distances away from the camera, as well as these panels that were situated behind the actor to act as a very fixed reference for our background. So we did have lots of other relative depth cues. And I believe that's just the four clips. I'd rather very short, as each one is only six seconds long. Okay. So for our testing sessions, we actually split our observers into two different groups based on the motion direction for that condition. So when observer came into a testing session, they were assigned to either the Z-axis motion or the lateral motion condition, depending on what we were testing that day. And then within each of those conditions, viewers would view pairs of video clips, each with a different combination of our three levels of speed and our three levels of IA. So within a testing session, in a particular trial, observers would be presented with two video clips presented sequentially. And the task we actually asked of our observers was, what clip did you prefer, the first one that was presented or the second one that was presented? And observers gave their responses using electronic remotes, which not only greatly cut down on our test time, but also reduced coding errors within our data collection. So first, what I'll show you is our effect of interaxial distance. So here, what you're seeing is along the Y-axis, we had the proportion of responses. What this is is the number of times each observer chose a particular video clip over the total number of times that was presented for a testing session. So the greater this number, the greater the preference for that particular condition. And of course, this was averaged across all our observers. And here I have our three levels of interaxial distance along the X-axis. So what you can clearly see from this graph is there's actually no effect of interaxial distance. And even if you compare our 2D conditions, so our zero IA condition to our 2D, 3D conditions, there's no significant difference between those two conditions. So what we actually see under these circumstances, the presence or absence of stereoscopic 3D does not actually affect your preferences in this case. However, if we look at the effect of camera motion, we do see a significant effect. So again here, I have the proportion of responses on the Y-axis and our three levels of camera speed along the X-axis. So first, if we look at our Z-axis motion condition, you can see there is this positive increasing trend as camera speed increases along the Z-axis. And this effect is actually significant according to our statistical analysis. However, if we look at this lateral condition, we see a flat, slightly decreasing trend as camera speed increases. And this effect is actually not significant. So there is no significant effect of camera speed in the lateral motion condition. So what this actually suggests is that within our study, viewer preferences only seems to be affected by camera speed when that motion is along the Z-axis. But specifically what we see is that we get stronger preferences for fast camera speeds along the Z-axis. Now this result is actually quite interesting given our previous predictions based on viewer comfort. So just to recap what I stated earlier about the general consensus of viewer comfort literature is that you tend to get higher ratings of comfort in scenes with either low amounts of motion or small amounts of binocular parallax. So based on that criteria, we would predict for our Z-axis motion condition that we should see lower preferences for our 3D conditions compared to our 2D conditions as well as lower preferences for fast camera speeds. However, in our current study where we assessed the measure of viewer preferences, we're seeing strong preferences for fast motion along the Z-axis and no effect of binocular parallax. So now we effectively have to ask ourselves why are we getting these differential results when we based our predictions on previous literature of viewer comfort. Now one possibility might be that the factors that should have maximized viewer comfort in this case do not necessarily produce maximum enjoyment within the viewer. That perhaps under these conditions, preferences for faster motion may have been driven by other factors. So now we essentially have to ask ourselves what is present within the Z-axis motion condition that's not present in the lateral motion condition that could be driving this result of preferences that we see. And one possibility might be the presence of looming cues. So looming cues simply refer to the increase in size of an image on the retina that's caused by an approaching object. I'm sure many of you have experienced this probably every day, but as objects get closer to you they not only appear perceptually larger, but that change in size also corresponds to that change in size on your retina. And there's been many studies that have shown humans can use these cues to very precisely estimate the time of collision of objects. And one very classic example is the throwing and catching of a baseball. And of course the higher the velocity of those objects, the much more imminent that collision is going to be and the much more salient that information is going to be to an observer. Now one thing that's actually unique about looming cues is because they're defined by that change in size of the retinal image, they're actually a monocular cue. That is they only depend on the information from one eye. So if the presence of these looming cues were somehow driving the effect of preference that we see, we would not expect there to be an effect of interaxial distance because it is a monocular cue. So now we have to ask ourselves, why is an effect of speed and motion along the z-axis? So the first possible factor of why we get this effect of speed I sort of alluded to in my previous slide, but it might be due to the differences in object motion alone between the two conditions. So because our z-axis motion does have the presence of these looming cues, it might be the fact that the higher the velocity of that moving object, the more salient that information is. And it's possible that this effect of speed within looming cues may have been enough to produce the effect of camera speed that we see in the current study. However, one thing that's also unique about an object moving in depth is that it also has changes in depth information or disparity information. And one thing we actually did not see in our study is we did not see a difference between our 2D and our 3D conditions. So if observers were using the object motion alone to base their judgments of preference, we would probably expect to see a difference between our 2D and our 3D conditions since our 3D conditions would have this change in disparity information as interaxial distance increased, but our 2D condition does not have this change in disparity information. So it's likely that this could be a contributing factor to the preference results we see, but it's likely not the only factor driving the results. So another possibility may be an effect of linear eviction. So when I say vection, I'm referring to the illusionary self-motion that a stationary observer feels when a large portion of their visual field moves. And a very classic example is a observer sitting on a stationary train as another train passes by them. And as they stare out the window at this train moving by, eventually they might get the sensation that they themselves are moving even though they are stationary. And there have been a few studies that has shown that in displays of the same size, you can get situations where looming optic flow can produce a greater sense of vection than lateral optic flow. However, it has been shown that these studies have been situationally dependent. But given our experimental setup and the stimuli used in our experiment, this is still a possible explanation for our results. So our observers could have been responding to an increased sensation of vection as speed increased along the Z-axis. And lastly, because we're dealing with something as subjective as preference, we can't ignore the possibility of higher order cognitive effects. So one possibility might have been our observers were responding to a greater sense of immersion in camera motion along the Z-axis. So one thing that is different between these two conditions is the direction of the movement between the Z-axis condition and the lateral motion condition. So that movement, that dolly shot towards the actor in depth is indicative of entering that scene, whereas in the lateral motion, that left-right movement is more indicative of passing by that scene. And it might have been possible that as camera speed increased along the Z-axis and that movement into the scene also increased, we might have gotten an increased sense of engagement and therefore a greater sense of immersion in those conditions. However, it's important to point out that within this current study, we actually do not have a direct measure of object motion, linear eviction, or immersion. But given our stimulus and our experimental setup, these are viable factors that could have contributed to the preference results that I've reported here. And these are by no means the only factors that could have been contributed to the results I've reported here. So what can we conclude based on the results of this current study? One thing I've clearly shown is that viewer preferences for moving stereoscopic 3D content do not necessarily depend on the same factors that influence visual comfort. That in fact, in this case, a variable can influence visual comfort and viewer preferences in very different ways, which I've shown here through the effects of motion and binocular parallax. But there could also be other variables that we do not control forward in this current study. So in some situations, enhancing comfort may produce less appealing content to the viewers. And of course, as filmmakers, we really need to be aware of this balance between comfort and preference in stereoscopic 3D content in order to produce both an enjoyable and a comfortable viewing experience. Just before I complete my talk, I just want to thank not only our funding agencies for this project, but also my four lovely co-authors. Thank you. Thank you.
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While heuristics have evolved over decades for the capture and display of conventional 2D film, it is not clear these always apply well to stereoscopic 3D (S3D) film. Further, while there has been considerable recent research on viewer comfort in S3D media, little attention has been paid to audience preferences for filming parameters in S3D. Here we evaluate viewers’ preferences for moving S3D film content in a theatre setting. Specifically we examine preferences for combinations of camera motion (speed and direction) and stereoscopic depth (IA). The amount of IA had no impact on clip preferences regardless of the direction or speed of camera movement. However, preferences were influenced by camera speed, but only in the in-depth condition where viewers preferred faster motion. Given that previous research shows that slower speeds are more comfortable for viewing S3D content, our results show that viewing preferences cannot be predicted simply from measures of comfort. Instead, it is clear that viewer response to S3D film is complex and that film parameters selected to enhance comfort may in some instances produce less appealing content.
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10.5446/21824 (DOI)
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Thank you. Thank you. Good afternoon, everyone. My name is Munko Chilirutomat from Chumbuk National University in South Korea. Today I present about our recent research progress titled as real-object-based 360-degree integral floating display using multiple depth camera. Here is the contents of my today's presentation. The first I will introduce about background works and conventional 360-degree integral floating display. And then I will present about proposed real-object-based 360-degree integral floating display and experiment results. And finally, I'll give some conclusion for you. As you know, the integral imaging is the most distinguished three-dimensional image, three-dimensional display system, which can display the full color, full per legs, and continues viewing auto-stereoscopic three-dimensional images from the real three-dimensional or depth-slide subject. But the display image provided with the limited viewing angle, image resolution, and depth range. And the volumetric light field display is one of the very good methods to display three-dimensional image in 360-degree. But the display image provides horizontal per legs only and binocular depth cues only. So considering both benefits and problems of both systems, we decided to combine these techniques to solve each problem. Let me explain about this system. This system titled as the conventional three-dimensional 360-degree integral floating display. Here, the elementary images are projected by the DMD projector, and reconstructed as the three-dimensional perspectives through the lens array. Double floating lenses relate the three-dimensional perspectives to the center of the mirror, when the mirror is rotated by the, and we're high speed by the motor. And in the experiment, we successfully demonstrated the full per legs 360-degree viewing angle, three-dimensional display, a three-dimensional image, but the vertical viewing angle is certainly narrow due to the function of the double floating lenses. Here's the example of the displayed image, and the vertical viewing angle is very narrow, but the horizontal viewing angle is unlimited 360-degree. So thereafter, we proposed the method to enhance the vertical viewing angle by using the anamorphic optic system, which is the vertically curved convex mirror, instead of the simple flat mirror. Here, the convex mirror can expand the light rays more widely in the vertical direction, so vertical viewing angle can be enhanced so much. In the experiment, as you can see, the vertical viewing angle has been increased successfully, up to 50 degrees approximately. Now, I'm showing the examples of the displayed image in horizontal direction and in vertical direction. The vertical direction I captured this image in both plus and minus approximately 25 degrees. Last time, we also proposed the image quality enhancing method to using the hexagonal lens and hidden point removal apparatus, because the resolution of the elemental image has been fixed by the DMV projector resolution, so we need to enhance the image quality without consigning the image resolution. So as you know, the hexagonal lens array has a more field factor than the rectangular lens array, and it also can include the more number of the elemental lenses. And of course, the elemental lens creates the more number of the point light source, and the point light source, the number of point light source is a very key factor for the image quality. Also, the hidden point removal apparatus is determining only visible points in each viewpoint in our system. From this comparison, you can see the HPR apparatus can detect the more accurate vision of the point cloud model, because point cloud model has been used in our system. Here is the example of the image quality enhanced 360-degree display, and here is the case without using the hidden point removal apparatus. And now we proposed the novel method to display the real object in the 360-degree integral photo display. The multiple depth camera required the real depth information of the real object, and reconstructed them as the point cloud model inside the computer graphics. And from the reconstructed point cloud model, the elemental images are generated through the given lens array specifications, and the generated elemental images are projected by the DMD. The hexagonal lens array reconstructed them as the three-dimensional perspectives. Then the double-photo lens relayed them to the center of the rotating mirror. Here, the depth cameras acquired the depth information from each given viewpoints for them, and saved all points' coordinate information, and reconstructed the corresponding visible points by using the detected coordinate information. For the combining point cloud models, we used the iteration classes points, point algorithm, ICP algorithm with the rigid transform. Here, the center-oids of the both data sets are given by these system equations. Then the shifting the center-oids into the same origin points of the both data sets, and using the detected rotation matrix to detect the iterated points of each data set. Then, translate them, translate the register them in each other. This is the combination process of the point cloud model, and at least the three point cloud data can be combined as the synthetic point cloud model. From the synthetic point cloud model, the HBR operator determines the only visible points for each angular step of the rotating mirror. For the detected visible points, the first we need to calculate the mirror reflection point, which is the P-par. Here, we used several coordinate systems. The first one is the main systems coordinate information with X, Y, and Z values. For the P-point, the XYZ value has to be converted into the UVW values, which are the local coordinate system of the rotating mirror. From the XY value to the UVW value, we can convert the information by using these equations, where the phi is the rotation angle of the mirror. Here, after converting the UVW values, we can find very easily the reflection point of the P-point by using these equations. Then, we have to reconvert the gain from the UVW to the XYZ values by using these equations. Finally, we can calculate this initial two-dimensional point through the double-fault lenses by using these equations. From the initial point, we can generate the elemental image arrays through the conventional interval to pick up the stem, where the sampling rate has been given like that. In the experiment, we used the POPI as a real object and the Kinect sensor as a depth camera. Here is the DMD projector, collimating lens, double-fault lens, and rotating mirror. Here, due to some hardware limitations, we used only one depth camera in the experiment and rotated the object at a given angle and acquired each depth information. Here are the specifications of our object and optical device. The real object POPI got this size of dimensions and the point cloud registration. Here, from the zero point, 120 points and 240 points, we used a number of points in each point cloud model and synthetic point cloud model has included this number of the points. Here, you can see the depth information from the corresponding viewpoint of real object. The three kinds of point clouds are combined into one synthetic point cloud model. From this figure, you can see the combined synthetic point cloud models consist of the three initial point cloud models. Here, the example view of the synthetic point cloud model in the horizontal direction from the 45 and 225 degrees. Those are the corresponding generated elementary limits through the given laser ray. In the experiment, we successfully demonstrated the real object-based three-dimensional image in the 360-degree horizontal viewing angle and up to 50-degree wide viewing angle. In the conclusion, we proposed an old 360-degree integral photo display based on the real object. The multiple depth camera is being utilized to acquire the depth information. According to the acquired depth information, the initial point cloud models are constructed in the computed graphics. By using an ICP algorithm with a region transform, the point cloud models are combined in the entire synthetic point cloud model. Elemental limits are generated for the newly generated synthetic point cloud model. In the experiment, we successfully demonstrated the three-dimensional image from the real object in the 360-degree viewing angle. Our further research is focused on the more accurate calculations for the point cloud registration algorithm and more improvement of the display image quality. Here's our reference papers here. And that's the end of my presentation. Thank you very much.
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A novel 360-degree integral-floating display based on the real object is proposed. The general procedure of the display system is similar with conventional 360-degree integral-floating displays. Unlike previously presented 360-degree displays, the proposed system displays the 3D image generated from the real object in 360-degree viewing zone. In order to display real object in 360-degree viewing zone, multiple depth camera have been utilized to acquire the depth information around the object. Then, the 3D point cloud representations of the real object are reconstructed according to the acquired depth information. By using a special point cloud registration method, the multiple virtual 3D point cloud representations captured by each depth camera are combined as single synthetic 3D point cloud model, and the elemental image arrays are generated for the newly synthesized 3D point cloud model from the given anamorphic optic system’s angular step. The theory has been verified experimentally, and it shows that the proposed 360-degree integral-floating display can be an excellent way to display real object in the 360-degree viewing zone. © (2015) COPYRIGHT Society of Photo-Optical Instrumentation Engineers (SPIE).
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10.5446/21825 (DOI)
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Good afternoon, everybody. So I'm Joana Rousson and I would like to explain to you what I did during my studies, so entitled subjective contrast sensitivity function assessment in stereoscopic of gamma patches. But first of all, please let me introduce you and give you more insights about the context of the study. So as it was mentioned, I'm working on medical displays. So this study was intended for medical applications. So what you should know is medical displays and especially diagnostic displays, so for radiologists, needs to be calibrated. And why do they need to be calibrated? They need to be calibrated to ensure that whatever the device, a radiologist, or whatever the display the radiologist is using, we still have the same image representation. So wherever he is in the hospital or wherever he is in the world at another hospital using a diagnostic display, always the same image representation he should get. So how can we ensure consistent image representation? It's done by standardizing the displayed luminance to the luminance perceived by the eyes. And this is handled by accounting for the sensitivity of the human eye to changes in contrast. And this is also denoted as a CSF when we display a luminance. So the CSF stands for contrast sensitivity function. It's the human eye ability to detect a low contrast pattern stimulus. And it depends on the special frequency of that pattern. The contrast sensitivity function has been intensively studied since the 60s and it has even been modeled in the 90s, late 90s by Barton. Yet the contrast sensitivity function has always been studied under 2D visualization conditions only. And despite medical practice is progressively moving from 2D to 3D formats, no studies or almost non-studies have been performed to try to assess the contrast sensitivity function under 3D visualization conditions. So when looking at 3D images. So the objective of our study, I think as you can imagine, was to assess the 3D CSF. So would the CSF be different if we have a 3D display? If we look at the 3D display and 3D images, would the CSF be altered? We also wondered, okay, if we use a 3D display but under 2D visualization conditions, so as a normal 2D display, does the CSF still hold? That's also one of our questions during the study. And so we studied the CSF because we wanted to know if the calibration algorithms should be revised for medical displays. So methods and materials for this study. As equipment for our experiment, we use Barco 24-inch fully HD display. It comprised a pattern with order, so especially multiplexing the right and the left view. Okay, here is the stimuli we use. It's called a GABA patch. It's a 2D vertically oriented GABA patch. That's the system that we use during all the experiments. So the GABA patch is just, in fact, the multiplication of 2D cosine pattern with a dedicated frequency F and a dedicated contrast C in the formula. So you can see just here. And it's multiplied by a 2D Gaussian. So okay, for our experiment, we had also to add a few additional constants like A to account for the viewing distance and the pixel pitch because when we assess the CSF, we take care of having the proper visual angle, so in terms of visual degree, visual angle, we need to properly calibrate everything in terms of viewing distance, pixel pitch and so on to get the proper number. And also you have a few constants like the offset of the scaling that were used, in fact, to get digital driving levels. So instead of having numbers between 0, 1, having numbers between 0 and 255 that are required for the display. Okay, no, sorry. Yeah. So during these experiments, a few parameters were changed. So first the contrast. It's okay because with the CSF, to assess the CSF, the contrast sensitivity function, we need to find the contrast threshold. So the contrast at which the detector can barely see the stimulus or just can't see the stimulus anymore. So of course, we had to change the contrast to find this contrast threshold. Also the spatial frequency because as I mentioned, the contrast sensitivity function depends on the spatial frequency. But also to have what we call 3D visualization conditions, we altered the depth plane position. So the plane where the 2D Gabber patch was lying. And also we had some 3D inclination. So to explain it a bit more. So you have a Gabber patch. However, our Gabber patch was lying at the display plane. So that's what we call 2D visualization condition. Or we, let's say, moved our Gabber patch further from the observer. So kind of translation along the axis to have it lying at the depth plane, virtual depth or virtual plane that is behind the display plane. And then for the 3D inclination, what we did is just that we did a rotation around the x axis, around this axis, to create this 3D inclination. The 3D inclination was also only performed when we had a depth plane different from the display plane to ensure that the whole image was always behind the display plane. So we performed all the experiments for seven different special frequencies ranging from 0.4 cycles per degree to 10 cycles per degree. To the orientation, just to say that, OK, we studied a vertical Gabber patch, vertical oriented Gabber patch, no 2D orientation of a Gabber patch. Two 3D inclinations, so either 0 degree or 45 degree, and two depth plane, either 0 being the display plane or 171 millimeter behind the display plane. So in fact, we have three what we call configurations. So to assess the 2D CSF, it means that you have depth plane of 0 to inclination of 0. For the 3D CSF, you have depth plane different from the display plane and 3D inclination of 0. We also studied an overt 3D inclination. So for the subjective experiments, we used nine non-expert observers. They were all tested for their vision and for their sterocracy. We used a controlled environment to ensure that we had uniform psychophysical conditions over all the tests. Then we also, so to find the contrast threshold, we used a 3D 1-up staircase experiment. So the staircase, it consists into either decreasing or increasing the contrast of the displayed stimulus, depending on the response of the observer to the preceding stimulus. So if the observer said, yes, I see the stimulus, then we decrease the contrast by a certain step down. And if he says, no, I do not see the stimulus, then we increased the contrast by a certain step up. 3D 1-up, it stands for the fact that after the first reversal was reached, so the reversal is a change in the direction of the contrast. So after the first reversal is reached, three yes answers, so yes, three times the observer had to answer three times, yes, I see the stimulus to have a decrease in the contrast, while only a no answer was required to increase the contrast again. And so after we performed the staircase for 22 reversals, and the 22 reversals are reached, and then we used the last 20 reversals to make, so we took the mean and we determined the contrast threshold. And then you have to know that the contrast sensitivity is the inverse of contrast threshold. Okay, there were a little bit more calculation behind that that you can find in the paper, but in general that's how it's working. So for to analyze and all our data, so first we checked if it was normally distributed and it was not. So instead of this fun, this calculating and displaying means, we decided to go for medians and first and foremost quartiles and to go also for non-parametric significance testing, like for example the Freedman test, to compare medians of different configurations for different frequencies, but also the one sample Wecoxon sign-run test to compare in fact medians, the medians we measured for the 2DCSF to values written by Barton's model. So main results and conclusions for our study, when comparing our 3D, when using our 3D display as a 2D visualization device, so a depth plane of zero, so the display plane 3D inclination of zero, we wanted to know if we were still in agreement with Barton's model. So as you can see on this plot, but also in the results of the significance test, so one sample Wecoxon sign-run test, you can see that the null hypothesis is never rejected. So it would mean that there's no statistical significance proven between our measured medians and the value written by Barton. So what we drew as conclusion that okay, apparently according to this result, the 2DCSF still holds for 3D monitor when used as a 2D visualization device. Then this was, let's say, the more important part, it was to know if the 2DCSF differs or not from the 3DCSF. So 3DCSF, I remember you, it was when the depth plane behind the display plane only was considered, no 3D inclination yet. So what we, as you can notice, okay, on the plot, it seems that at low frequency there's a decrease in terms of contrast sensitivity, but a small increase at high frequencies. I remember that I put the medians first and third quartiles. And okay, the significance test, this thing, so comparing the medians for the 2DCSF to the medians measured for the 3DCSF, we see that at low frequencies and high frequencies, so below 1 cycle, till 1 cycle per degree and at 10 cycle per degree, the null hypothesis is rejected. So apparently there would be statistical difference between the 2D and the 3DCSF at these frequencies. So yeah, as you can notice. So okay, our results suggest that the 3DCSF would differ from the 2DCSF. Now let's compare. So here we are under 3D visualization conditions, but now let's add some 3D inclination. So instead of having no 3D inclination, now we have a 45 degree 3D inclination. Okay, if you look at the medians, we have the impression that there would be a decrease in sensitivity due to, no, it would be an increase in sensitivity thanks to the added 3D inclination, but in fact that was not confirmed by significance testing. And later we also did an over study with a 60 degree inclination and okay, maybe it was due to the observers, so we did that 60 degree inclination with new observers and we didn't have this tendency at all and also the null hypothesis was also rejected for all the frequencies. So apparently when adding a 3D inclination, we don't have an additional impact on the 3DCSF. So as conclusion, what we got from our study was that apparently the 2DCSF still holds for 3D monitors as a 2D monitor, but it seems that the 3DCSF differs from the 2DCSF. So if the 3DCSF differs from the 2DCSF, this means that maybe we should consider revising our calibration algorithm for 3D medical displays, but when displaying a 3D image, we can't calibrate it the same way when we add only 2D images. But okay, further studies are being performed on this topic to know exactly how it should be, how it should be altered and also run this experiment with more observers, but these were the first results we obtained. Okay, I would like to thank for that talk. IWT, who supported this project in the context of background ground named optical simulation modeling and evaluation of 3D medical displays and of course to give special thanks to all the observers who took part in the experiments. I thank you and if you want to see the stimulus, also the staircase and how it was built and also to see this depth plan, these 3D inclinations, we will be at the demo session. So this afternoon, this evening, and with all the equipment, okay, except the control room, but we will have all the software, the equipment, so if you want to have a look at this study, you are all invited to come and try it yourself being the observer yourself. Thank you. Thank you.
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While 3D displays are entering hospitals, no study to-date has explored the impact of binocular disparity and 3D inclination on contrast sensitivity function (CSF) of humans. However, knowledge of the CSF is crucial to properly calibrate medical, especially diagnostic, displays. This study examined the impact of two parameters on the CSF: (1) the depth plane position (0 mm or 171 mm behind the display plane, respectively DP:0 or DP:171), and (2) the 3D inclination (0° or 45° around the horizontal axis of the considered DP), each of these for seven spatial frequencies ranging from 0.4 to 10 cycles per degree (cpd). The stimuli were computer-generated stereoscopic images of a vertically oriented 2D Gabor patch with a given frequency. They were displayed on a 24” full HD stereoscopic display using a patterned retarder. Nine human observers assessed the CSF in a 3-down 1-up staircase experiment. Medians of the measured contrast sensitivities and results of Friedman tests suggest that the 2D CSF as modeled by Barten1 still holds when a 3D display is used as a 2D visualization system (DP:0). However, the 3D CSF measured at DP:171 was found different from the 2D CSF at frequencies below 1 cpd and above 10 cpd. © (2015) COPYRIGHT Society of Photo-Optical Instrumentation Engineers (SPIE).
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10.5446/21826 (DOI)
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From crashing through a story of Mike May, a quote, the brain imposes knowledge in order to see. But I think there might also be beauty in not imposing knowledge, in being open to everything, and being open to every possible interpretation. In ways, there's something liberating about my vision in the sense that so much of what I see can be anything. It's fascinating to think that an object or even a person can be anything. It means that almost anything can be beautiful. Mike May said this several years after restoration of his site in One Eye. He lost his site as a small child and regained it in his forties. He had no visual memory to help him recognize what he was looking at. He couldn't even recognize his wife. Claude Monet and the Futurists, among others, were also addressed the encumbrance of memory in appreciating beauty. From Art and Physics by Leonard Schlein, Monet once said he wished he had been born blind and later gained sight. That way he would be able to look at the world free of the knowledge of what the objects were so that he could more appreciate color. Robert Hughes comments, on the early 20th century Futurist artist Marinetti in Shock of the New, Marinetti's enemy was the past. He attacked history and memory with operatic zeal, and a wide range of objects and customs fell under his disapproval, from Giovanni Bellini altarpieces to the erratic Italian love of pasta. This dichotomy between the ability to see and the dependence upon memory to determine what we see is of primary concern to artists. Our past expectations become a hindrance to our experiencing beauty in the present. It is in the creation of a relationship of visual objects to memory that matters, that makes art. An experience concerning this relationship of shapes and other visual information not remembered as names or things or otherwise identifiable objects becomes metaphoric of what the artist sees. A change is required in the way we look at things, a shift as it turns out to a different part of our brain. Our minds evolved by natural selection to solve problems that were life and death matters to our ancestors, not to commune with correctness or to answer any question we were capable of thinking. This from Stephen Pinkers, How the Mind Works. From necessity, we learn to deal with information quickly by reducing it what we observe to manageable size. This information must be processed by our brain to be identified and an appropriate response generated. All this in a fraction of a second. We have been forced to see in terms of what we conceptualize and know from memory. I see what is happening, compare it with previous experiences and feel emotion. Is this feeling one of fear or joy? Do I stand or run? Do I respond or disregard? This reductionist way of interpreting visual data is imprinted in our brain. An example of this is the way we understand the human face and body. We think profiles and straight on views, not three quarter ones or foreshortening. You think of a hand like this, not like this. This is exemplified in the art of ancient Egypt. Look at this Egyptian stele in this slide. Both the head, hips, legs and feet are all in profile while the shoulders, chest and hands are in frontal view, all avoiding any foreshortening. This is the way we think these body ports, not what we really see. Our vision is influenced by social construct and technical convention as well. We might think a king more important than his servant and an artist might paint him larger. Thus, artists must often unlearn what they know about familiar objects, people and social norms and look at them in a fresh and altered way and see what is really there. This involves not looking at a foot as a foot but instead seeing it as a shape of different tones and colors proportional to the rest of the figure. Lining up, sighting angles and measurements are often necessary. Note that this process of not looking at the subject in familiar terms as foot, toes, toenails and heel is necessary to encourage that part of our thinking which deals with concept and the abstract to relinquish control allowing the creative part to do what it does best, that is see the foot in order to draw it. Gravity and light are well known to the artist. If shadow doesn't ground an object, bind it properly or to place and time, then something seems amiss. Take away shadows and perspective and what have you got, a feeling of displacement or unease. We have learned that shadows give us a sense of time and placement. They are part of our subconscious thinking as with perspective indicating depth. This slide is an example of what happens when the artist plays on these expectations. Giorgio D'Aquirico was a master at putting the viewer in an unreal place where vanishing points made no sense and shadows indicated a time of day contrary to that of the light, a place that could only exist inside our imagination. Our perception of a constant shape and lightness across changes in viewing conditions tracks the object inherent properties from Pinker. The most dramatic example of this perceptual consistency concerns color. We learn to recognize a lion in all lighting conditions. In the sun coming through the trees, in the grass, and in the shadow of a rock. In our mind, the lion retains the same color in all situations, though physically its color may vary considerably. This color constancy or local color as artists like to call it, follows what Simear Zaki refers to as the golden rule of perception, namely comparison. The brain looks at colors and shapes in relationship to their surrounds and is able to see the same yellow no matter what the conditions. The ratio of the amount of light of differing wavelengths never changes. Information must be simplified and codified in order to be processed in the moment. The rules we use to gather information for survival often break down when compared with actually seeing what's really there. The yellow in the shade may in fact be violet, but because of neighboring colors we still see the same yellow. Our brains necessarily simplify as too much data can clog the system and prevent identification and timely action. Throughout history, scholars have noted the duality of our thinking. However, not until Sperry conceived of surgically dividing the two hemispheres of the brain, known as a commiserotomy, and with the subsequent advent of brain imaging systems such as the MRI and CAT scans to give a picture of the brain's activity, were different responses of each cortex observed. Characteristics of each side of the brain were identified. Typical features of the left were found to be linear, timed, logical and rational thinking that is doing and abstraction. Typical features of the right hemisphere were found to be imagination, spatial cognition, intuition, holistic thinking and all at once perception, being, metaphor. As one might conclude from these hemispheric polarities, the scientists who relies on empirical study requiring a logical, linear and conceptual methodology thinks mainly from the left side while the artist who thinks takes a more creative, holistic and emotional approach sees from the right. Metaphor is the cornerstone of fine art. There is a layering of different planes of comprehension. Like worlds of thought that are linear and logical, relationships are implied and directly expressed within a work. Realizing parallels often flies in the face of much thinking as they must be experienced and seen and not sequentially explained or thought. For example, a saison painting of a bowl of fruit is not an appetizing depiction of a set, but a set of relationships of shapes and planes of color. These reflect artists' need for balance and equilibrium even though the table would surely topple in the real world. As Joseph Campbell points out, one does not want to eat a saison apple, but rather experience the visual truth of it within the confines of the canvas. It is in understanding the relationships between the objects depicted and those of the objects of one's own experience, both visual and personal, that leads one to truly see the work of art before him. The still life is a painting of what he sees. The painting becomes a metaphor for understanding everything else. Again, as Campbell puts it, quote, nothing within the field, that is the border of the painting, has referenced to anything outside the field. Within that field, what is important is what is here and here. The relationship of part to part, of part to whole, and of the whole to each of its parts. And when that relationship is fortunately achieved, you have claritas, radiance, fascination, aesthetic arrests, aha, you are held, end quote. As artists and scientists employ different methodologies in trying to understand who we are and what we are striving to achieve, in the end we come to understand the same thing in very different ways. We create new languages to explain what we have discovered. Scientists communicate truth through experimental reasoning, while artists communicate through visual metaphor. Perhaps it's the inability to translate these languages that causes such conflict between the two and perhaps helps polarize society as well. At last year's conference, I presented the idea of environmental stereoscopic art as a way of becoming more aware or more conscious of the visual process and consequently gain greater insight into consciousness itself. I turned to chroma depth 3D glasses. These rely on differing refractions of incoming light for each eye, thereby placing colors at various distances from the viewer, due to the spontaneity afforded by these glasses by not having to create two images. The resulting change in consciousness from left to right brain thinking is palpable. This work, the mechanics of understanding, comes close to the way I see the world. These are at once sharp and distinct, yet as I look, the shapes change. They're one way now, another way depending upon my focus. I feel the presence of other forces in my head as I look. But as I look, it makes sense to me, aesthetic sense, emotional sense. One cannot see it in all, in only one glimpse. And I apologize for cutting this short. This work, Can You Read Me, may give a limited view of visual space created by layers of writing. The marks are inextricably tangled with each other, and yet the mind detects an order within the apparent chaos. Using the 3D chroma depth glasses, the layers become visually separated, allowing me to better appreciate the image. One must indeed be in their right mind in order to read me. Well, obviously I don't have time for the rest of this, but I would like to just say that somebody asked me, well, so what? What's this all about? By going back to the root of our perception, we may take full advantage of the new technologies that are becoming available by trying to step around our expectations, our preconceptions, and not just follow those in logical conclusions. If we don't, we're just making an updated fancy TV or a new type of atom bomb. Thank you.
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This paper continues my 2014 February IS and T/SPIE Convention exploration into the relationship of stereoscopic vision and consciousness (90141F-1). It was proposed then that by using stereoscopic imaging people may consciously experience, or see, what they are viewing and thereby help make them more aware of the way their brains manage and interpret visual information. Environmental imaging was suggested as a way to accomplish this. This paper is the result of further investigation, research, and follow-up imaging. A show of images, that is a result of this research, allows viewers to experience for themselves the effects of stereoscopy on consciousness. Creating dye-infused aluminum prints while employing ChromaDepth® 3D glasses, I hope to not only raise awareness of visual processing but also explore the differences and similarities between the artist and scientist―art increases right brain spatial consciousness, not only empirical thinking, while furthering the viewer’s cognizance of the process of seeing. The artist must abandon preconceptions and expectations, despite what the evidence and experience may indicate in order to see what is happening in his work and to allow it to develop in ways he/she could never anticipate. This process is then revealed to the viewer in a show of work. It is in the experiencing, not just from the thinking, where insight is achieved. Directing the viewer’s awareness during the experience using stereoscopic imaging allows for further understanding of the brain’s function in the visual process. A cognitive transformation occurs, the preverbal “left/right brain shift,” in order for viewers to “see” the space. Using what we know from recent brain research, these images will draw from certain parts of the brain when viewed in two dimensions and different ones when viewed stereoscopically, a shift, if one is looking for it, which is quite noticeable. People who have experienced these images in the context of examining their own visual process have been startled by the effect they have on how they perceive the world around them. For instance, when viewing the mountains on a trip to Montana, one woman exclaimed, ”I could no longer see just mountains, but also so many amazing colors and shapes”―she could see beyond her preconceptions of mountains to realize more of the beauty that was really there, not just the objects she “thought” to be there. The awareness gained from experiencing the artist’s perspective will help with creative thinking in particular and overall research in general. Perceiving the space in these works, completely removing the picture-plane by use of the 3D glasses, making a conscious connection between the feeling and visual content, and thus gaining a deeper appreciation of the visual process will all contribute to understanding how our thinking, our left-brain domination, gets in the way of our seeing what is right in front of us. We fool ourselves with concept and memory―experiencing these prints may help some come a little closer to reality. © (2015) COPYRIGHT Society of Photo-Optical Instrumentation Engineers (SPIE).
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10.5446/21827 (DOI)
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Agen, i genPeisodd awgfodd o'n 잡 Jason paramol. By Excidus, mae'ndefnyddio g pneum, wedi'i elefyn, Give me tyresau. R Sicoli Aesido New(?) Harithre Cobe smoothly Roisi superior a chwudwch yn enryd, Wedi dweud o ni o'r 100 yn ni siart ac yn yni, Lleasir i Ian'� vary XD Scarff yn Fe Lindsay MaeEnstaneth i GweithioKorean arrays yn Sfrosciae Bets dewon. A'r transfer o'r f docsiei roedd arny Roddiol three-D MaeFาง iawn, a ajw fauth datgani'r hydu i gael. Efallai yn hyrdd i ddim fedddangosol i'r ymblucig-inkle, mae'r llimerio wedi cy們 fyddai 30 sisi. Felly, mae enddors. Felly, wrth gtw broughtion. Fe wneud cam industry, a yma'rèel mae'r paymention bueno ar �要nebuioeches three-D, Focoment yn Unedigetohon I ddoedd yn ganllunol young ar 234 Fodol drwy Enw sydd glygu yn wonennu'n nhw fel yma yng Nghaerunning D Morefod yma ar y cy clo. Mae nobodyadwn yn gwleidio, really. Mae fedrumingol ar Dream Taking 34.재 Maenad연 gydfodd meno bach. Yng Nghaerドch yn gyonom i'r cynllunIG i sonsiaiddd ymate Along, han cyntaf o sailioludding Valent L وت? Achos mae gritamiaeth os yw'r gym international â ddweud y dynamolf 말이 i weld y newydd S14 Luke Efallai â colliolwyrer gan gweithio'w cyfio ar gyflem maker ond byddei un Crowd Prize fo française cerdarnodeh, a phred ddyda'r cyllide i fynd i wneud i'n ddweud y gallu cyfnodd. Mae'r gweithio yma yn ymdweud y tectnologi ar y ffordd y ffordd. Mae'r ffordd, mae'n ddweud. Mae'n ddweud yw'r ffordd yw'r ffordd yw'r ffordd yw'r ffordd yw'r ffordd. Felly, y idea yw'r idea yw'r cyffredinol y system yw'r cyffredinol yw'r ffordd yw'r ffordd. Mae'n ddweud yw'r pwysig yw'r ffordd yw'r ffordd. A y dweud yw'n ddweud yw'r ffordd yw'r ffordd. Felly, mae'r ffordd o'i ddweud yw'r ffordd, yn ymgyrch iawn o'r ffordd, i'r wneud o'r technol i'r ffordd. A bwysig, fyddech chi'n gwybod o ffordd, yw'r ffordd yw'r ffordd yw'r ffordd, i'r gweithio'r gweithio'r gweithio'r gweithio. Mae gestio'r siwr fawr bod I Golden Cres fan pobl agor i'r sgwrth y gallai hynywadau teins oIntro cynyddol ai chi head tracking, iddyn nhw'n gwae leowon i ddim nes iddynt, sy'n rydych chi'n allwn hefyd, gwneud hynny ddim arnu yma i chi, ac mae儿 wrth fas i yw erbydd. Oedda'n lawer, bod podeidwch rightewn Bünaurel 3D. Oedda i'r Bud sur o phoglansol. Llyfr� работiaid dim ni fyrwyr ni mi eithaf. Mae'n rheinkydd y ffordd nesaf,ddian o naddoryn yn anthranol ac yn welth pro Richmondaen, i shows a'u cyhoedd pan yokio. Darwy�� Hefyd yn gallu טra overall o'r ffordd A'r bach簚ad, yr awwmnidol yn Maenens cubeda Fe'i piwaeningswig yn ba yn bod draw Nawr g埋 i yan i ble fydd yn fullfyn nhw iawn, a'r newid mewn i'r hynion y hir. Welcome tocard. Ffawr cyffaint ers iechyd anodag efallai, rule recording, ond y stations canigau i ei migaf o gymdeithasol. Undew ni wedi gweld i gael y Chodialkgriff y yma i ei cyfrif achir canigau, i ni'n los i gymdeithasol, sy'n cael ei ddatbyn gwyl i gyfrif. is itself has a light bar as it's called and that can be optically tracked as well. And we don't want to isolate the player in the virtual reality experience, this is often a criticism of virtual reality. So we can send the image from the device to a television so that other people can enjoy the virtual reality experience and maybe interact with it as well using perhaps the tablet or their mobile phone. So here's the thing, the concept actually is a lot older than you might imagine. In fact it dates all the way back to here with Morton Highlig who's proposed this virtual reality device head mounted display and let's have a look at the specification. He had wide field of view optics as well, he also mentions binaural 3D audio and an internal air circulation system even that simulates the breeze on your face and all with a comfortable balanced ergonomic design. So the question is well why are very few people heard of that, what went wrong? And really the answer is that of course the technology wasn't available at the time to create such a device. In fact it's only just available now and when I say just I mean within a matter of months. We've got a situation where the mobile phone industry has had enormous advances in display technology and also movement detection as well and the console game industry has given us amazing real-time image generation capability to feed those displays. And we've got other progress in all sorts of industries, anything from audio processing to computer designed optics as well. But having said that I mean although it's fantastic to have a computer designed optics actually the basic principles of the optics date back an awful long time. So before I said it gives the impression that you're looking through a window, well what does that mean? Well in a sense it's all about asking a question of what's the difference between looking at an image on a screen and looking at the real thing through a window. And I suppose a lot of it is down to what happens when you change your viewpoints. So here I'm moving this camera around and you can see that the two images are behaving in a completely different way. We've got motion parallax there. There's only one position where the two images line up and even in that position they're focused at a completely different distance as well. So the question is could we come up with a device that solves these two problems? Well the answer is quite a simple one. All we need is a magnifying glass. We just place the magnifying glass in front of the display and then the image on the display appears to come from somewhere in the distance. Well it's all very well showing a diagram but I thought I'd show you what it actually looks like. So here I've placed a magnifying glass in front of the display and now you can see that as I move the camera around the image on the display pretty much perfectly lines up with the view out of the window. And it's focused at the same distance as well. In fact it has to be for this particular illusion to work. Now in order to achieve this the alignment of the components is really critical. So the projection centre of the image on the display has to exactly line up with the optical centre of the lens and the fields of view have to match as well. So for binocular vision we effectively need two sets of lenses and now we're getting very close to this sort of optical arrangement that we have in our head mounted display. The images are arranged in a side-by-side configuration with a central septum dividing the display in two so that the left eye only sees the left eye image and so on. Now actually this arrangement dates back all the way to Sir David Brewster's original lenticular stereoscope from 1849 and at that time it wasn't possible to make lenses with a consistent focal length. So he came up with the innovation of using a single large lens dividing it in two and then that gives you the two eye pieces. Swapping them around you can see that the optical centres are now a bit further apart than our eyes are and so this dictates the size of the image on the display as well. Now the lens block actually opens up for cleaning and you can look inside and you can see the sort of half lenses just as they are in that diagram and they look like prisms don't they so it's sort of it is deflecting the light inwards towards your eyes. The images themselves were supplied on interchangeable stereo cards and I thought I'd show you a selection of just a few images that were created around that time or in fact in this case we know the exact time it was the 12th of August 1858 and the images look impressive now and it's almost impossible to imagine how astonishing these images must have appeared at that time. So the device allowed you to illuminate the cards from the front using a mirror arrangement and that gave a very directional light which was necessary for the early silvery surface of daguerotype images but also you could view glass slides as well using the ground glass screen to give you back illumination. Now I may be wrong about this but I suspect that the original stereoscope was probably one of the very first modern consumer products you had the concept that you bought a device and then you bought content for it the hardware software idea and certainly these stereoscopes were manufactured in enormous numbers and so of course were the stereo cards. Now inevitably you get a situation from time to time where there would be manufacturing defects so for example this stereo cards could be vertically misaligned for example and this next stereoscope has a very innovative way quite a simple way of solving that problem. It was made by the optical instrument manufacturer Smith Beck and Becker around about 1860 and they also made Charles Darwin's microscope so we're talking the the ultimate in quality. It's full of innovations but let's see how it goes about solving misaligned stereo cards. So here we have our misaligned stereo card we've got vertical misalignment and what he did was he rotated the eyepieces which had the effect of rotating the prismatic lenses so that instead of just having a sort of horizontal shift towards your eyes you got a little bit of a vertical shift as well to correct for the parallax errors. So let's have a go at doing that. If I can advance the slide try again there we go and so we rotate the lenses and correct for the misalignment. Of course you have to remember to put the lenses back again when you're viewing the next stereo card. So this stereoscope from about 50 years later takes things even further and we've now got full calibration of the adjustment but here's a funny thing I mean it's a brilliant stereoscope and amazing optical quality but it's actually quite difficult to get an image on it. If you put your stereo card in the device it takes ages to set up all the adjustments to get a good image. Compare that to if the clicker will advance there we go to the simplicity of the home's bait stereoscope this is regarded by many as the classic stereoscope and all american design made in massive numbers it's very simple to make and also simple to use as well you could just view cards in the device not much adjustment just focus and it worked very well. Take things a step further still and we've got ViewMaster where there is no adjustment whatsoever on the device and yet it works for both adults and children alike and in fact this is the kind of thing that very much we try to do with our games consoles we want them to just work out of the box so some of the design features of this could very much be used by ourselves to make the device simple to use so okay how does it work for adults and children how does it cope with the say the differences in people's eyes separation into pupillary distance well the answer is we're back to that virtual window again so in fact here i'm just moving a 3d camera around and notice how little the image is actually changing and this means that the position of your eyes is actually not not really critical at all you can have your eyes in any position or indeed any interpupillary distance and you'll still see the same image we can rotate it vertically okay the image is rotating but we're not getting any vertical parallax move it in and out the image doesn't scale in size so that's very handy from a software point of view we can just use a fixed field of view now some people talk about the separation of the lenses in the stereoscope as an interocular adjustment and in fact it isn't and it's for adjusting for different stereocards let's see what would happen if we did adjust the lenses to match our eyes so this is the classic stereoscope arrangement and the lenses are matching the projection centres of the image if we oops there we go move the lenses inwards suddenly our stereoscope design has gone wrong and in fact we'd now have to diverge our eyes to see the image we'd have to move the projection centres inwards to match if we were trying to do that and it's amazing how many books talk about moving the lenses as an interocular adjustment even Sir David Brewster in his original book talks about moving the lenses from side to side to adjust for people's eyes and you don't have to it's actually for adjusting for the different stereocards so what have we learned from all this well certainly the internal alignment is very very critical and actually it's better to not provide it as a user adjustment because people probably don't know what they're doing but the good news is if you get it lined up correctly the external alignment is very tolerant if you think of the view master it just works and that's ideal for what we're after okay well the stereoscope so far have had quite a narrow field of view but really we would like if it goes on to the next slide um we'd like to have a much wider field of view to immerse ourselves in the scene and certainly as stereoscope design advanced they managed to reduce the focal length of the lenses to give you a wider field of view but typically they more used it for creating smaller stereoscopes more compact stereoscopes so you might ask the question well why didn't they want to produce incredible immersive ultra wide field of view images well i think one of the reasons is in fact very well explained in this paper where when you increase the field of view you start getting increasing amounts of distortion in the image in this case pincushion distortion and also chromatic aberrations and so on now in this paper he does suggest an optical arrangement that corrects for that distortion but even then you can only get the field of view out to about 80 degrees so on it was probably harvey ratliff junior who first suggested well look why do we really need to do the correction in the optics what if we pre distort the images apply a barrel distortion and then when it goes through all the optics and it'll just look correct the two distortions will cancel each other out and this was implemented particularly well by eric howlett with his leap optics system so he had the the idea of having a camera that created a fisheye distorted image that then went on to medium format film and then you viewed the image in his viewer that had the exact opposite distortion so that you saw fantastic linear images with a field of view extending out to 100 degrees or so and the good news is that we now and only just really now we can provide that distortion in software in shaders so we can create now the fisheye distortion and then the optics themselves will expand the image back out again to create the linear image that we're after and it also has an advantage that if you look at the pixels the smallest in the centre which hopefully is where you're going to be looking and largest at the edges which hopefully are going to be towards our peripheral vision so this is quite an efficient use of the pixels on our display now when you get to very wide fields of view all sorts of other things start to take effect like for instance the effect of eye rotation so imagine you're looking straight at the centre of the display the edges of the display are going to be seen just in your peripheral vision if you try and look towards those edges you rotate your eye and your pupil has actually changed position and that has the effect of altering the field of view so it's very difficult to talk about fields of view when you're talking about very wide field of view displays what do you mean do you mean the direct gaze field of view or the field of view that you get in your peripheral vision and this sort of interaction between the lenses and your eyes is very much the territory of optometry traditional optometry and actually we can learn a great deal from the expertise in that area for example people's glasses tend to be tilted forward slightly and that's referred to as pantoscopic tilt now we made the decision on our device to not compensate internally for people's different prescriptions but instead allow you to wear your own glasses with the device just to keep things simple again so we tilt the optical block of our device to match the pantoscopic tilt of the glasses which gives glasses wearers a much wider field of view but it's also good for non glasses wearers as well because human vision is biased downwards slightly anyway okay so we've got a wide field of view so now if we add head tracking we can effectively give ourselves an unlimited field of view now head tracking with computer generated images was first carried out by Ivan Sutherland back in the late 1960s with a mechanical arrangement and simple wireframe graphics to keep the frame rate high there's various different ways you can do tracking on our device we have on board accelerometers and gyros accelerometers measure of course acceleration and gravity as well and the gyros measure orientation changes and also we've got a number of leds that can be tracked positionally by the PlayStation 4's own stereoscopic camera so how does this all work well imagine that this is the head movement that you're trying to detect the accelerometers and gyros data come in at about a thousand times a second and give you this sort of effect where you're getting all the high frequency movement being captured really well but if you look very closely you can see it's not actually pointing in the right direction and it's going to drift over time as well the feed from the camera that tracking the LEDs gives you a very different kind of data it's coming in at a much lower rate 60 times a second but it's accurate and it doesn't drift so what we do is we take those two types of data and fuse them together to give the best of both worlds so now we have high frequency tracking that also is accurate and doesn't drift over time so we're now ready to create some images for our virtual reality experience and I thought it'd be worth just showing you how far interactive computer graphics image generation has come with the the latest generation of games consoles so what you're about to see sorry it's not in 3d but it's evolution studios drive club for the PlayStation 4 and remember what you're about to see is all rendered entirely in real time so there we go there is actually a little bit of audio in the background if you wanted to fade a level but just have to make your own engine noises oh there we go um you can see how realistic these images appear and in a moment we'll go inside the car and have a look at how the rainwater behaves on the wind screen it's actually modelled so it interacts with the airflow and the lateral forces on the vehicle just as it would in real life so we can certainly generate some very compelling images now there's just one problem and that is that typically image generation is carried out across multiple processors and often it's done in a sort of pipeline arrangement where the processing is handed from one processor to the other over a few frames and you can imagine that's not a great thing because what happens is that the tracking information that you read at the start of the image generation process is going to be very out of date by the time you look at it on the display now having said that developers are coming up with all sorts of clever ways to reduce this problem but nevertheless let's have a look at what happens when you have latency so imagine that this is perfect tracking this is what we're trying to achieve if we add latency we get this kind of effect so there's a bit of a delay and in particular it's going to be horrible when you stop turning your head and the whole world carries on moving that's going to be really disorientating for people and we have to do something about that so what's the answer well one thing we can do is make a prediction of where the viewer's head is likely to be at the time when the frame is being displayed and with a thousand hertz sensors we can actually do quite a good job of that so this is sort of what we get with prediction now often using prediction is sufficient to solve the latency problem but here I've slightly exaggerated the effect and you can see it's not perfect it's been caught out at the beginning and end of the motion because it obviously you can't predict those things correctly so there is another technique that is available to developers and that's referred to as last-minute reprojection so the idea with that is that just before you display the image you reread the tracking information and that gives you the error that you're going to have and then you just shift the image slightly to compensate for that error so this is what you get with reprojection and in fact you can see that now we're getting very very close to perfect tracking in fact the only thing that gives it a way is if you look at the edges of the image you can see that they're sort of side slipping to a certain degree and we can correct for that by just rendering to a wider field of view so actually it's now possible to create the illusion of zero latency which is really essential for virtual reality to work so there's a lot of things that we're now able to do that say in the 90s we couldn't achieve and it's all down to increase processing power we can do that optics pre distortion to the leap style wide field of view optics we can do good quality head tracking and sensor fusion and so on of course we can generate compelling looking images and also correct for any latency problems as well so right finally we're ready to show some stereoscopic 3d on our device now traditional 3d displays referred to us only being able to show a narrow range of parallax with a guaranteed level of comfort and so we use stereography to manage the 3d settings the interaxial and horizontal image translation last time i demonstrated some software that allows you to do that with games so you can see as I'm moving the camera around it's constantly adjusting the 3d settings to maintain comfort but here's the question why do we need to do that why can't we just show the full range of parallax and in truth you probably need a whole conference to answer that question and I suspect throughout this conference we'll be looking at that but I suspect a lot of it is down to you typically people not viewing the content from the exact perfect position in front of the display if you're a little bit off axis you're going to get a bit of keystone distortion vertical parallax that kind of thing certainly it's true that if you compensate for the viewing position you can show a much wider range of parallax comfortably and anyone who's familiar with using a virtual reality cave will know that you can show a lot more parallax in a device such as that without too many problems now the head mounted display had that virtual window idea so we can maintain the consistent viewing scenario and whether it's for reasons of that or other reasons one thing is certainly true you can show a much wider range of parallax in a head mounted display than you can on a traditional 3d display so we have the ability to show ortho stereoscopic depth real world one to one depth we can have perfect matched fields of view have the cameras where our eyes would be and that should greatly enhance the sense of immersion having said that that doesn't mean to say that we can dispense with the concept of having comfortable 3d so have a look at this image so this image is within a parallax range that would be legal to be broadcast on sky's 3d channel and yet as you can see it's horrible and now i'm not an expert at this kind of thing but i suspect the problem is that we can only fuse a narrow range of depth at any one time anything beyond that and you see a double image and you have to reconverge your eyes to view it and what's happening with that text in the middle is we're probably having to reconverge our eyes for every letter which is really horrible in fact i'll get rid of it so we can move the parallax to a narrow range and suddenly it is comfortable to view now this isnt just a problem with virtual reality it's a problem with the real world and it's why cars are now being fitted with head up displays so that the driving information is being shown at the same depth as the road where the driver is looking and we need to do this in virtual reality as much as possible when we're showing user interfaces if we need to keep the depth close to where we expect the viewer is going to be looking so we've got orthosterioscopic viewing conditions and actually this is something that the victorians were able to do as well typically the 3d cameras had lenses roughly six and a half centimeters apart similar to our eyes and the focal length of the lenses in the cameras matched the focal lens of the stereoscopes and i'll just demonstrate that with this example here so the image on the left i took a few years ago using just a compact camera with the image at a particular focal length the image on the right i took with the same compact camera the same focal length but looking through a stereoscope and this time it's looking at a glass slide taken by charles breeze back in 1860 exactly the same view and here's the thing i've cropped the image for the presentation but i've not scaled it the two images are exactly the same size so in other words the image on the display was exactly the same size and what that means is that when we're viewing that image in the stereoscope we are seeing ffountain's abbey at the exact same size that it would have been if we'd been there in 1860 looking at it for real so it's powerful stuff and of course we can do more than that in virtual reality because we've got head tracking so for example we could record the orientation of the camera and show the image in the same orientation that it was taken so if you are looking to tall building then why not show the photograph in that orientation so you have to look up to see it but of course we can do so much more with virtual reality we can project images onto for example a sphere view it from the centre of the sphere and we can have a complete 361 to one recreation of the world and the images can be stored in this format which is referred to as equirectangular projection and it's a bit like how a map of the world is done now capturing images for virtual reality well we could use a conventional camera the only problem is as we get an increased wide field of view we get increased distortion now that's not a problem for viewing in virtual reality but because we just see it completely one to one if the fields of view are matched but what it does mean is that there's going to be less detail recorded in the centre of the image than at the edges so it's not really a very efficient way of storing the data better approach if the clicker will work there we go is to use a fisheye lens and if we look at the same regions again you can see they're much more consistent which is what we're after now when we want really wide fields of view then we're into the realms of needing multiple cameras and stitching the images together and the only problem we're doing that is that any difference in the position of the lenses is going to create parallax which is going to make the images difficult to stitch together so really you want the lenses to be as close together as possible and the frownhofer institutes have come up with a quite innovative solution where they use mirrors so that the reflections of the cameras all appear at exactly the same point so that means that images captured with that camera don't have any parallax stitching problems now so far i've conveniently talked about monoscopic image capture but of course this is a stereoscopic conference so really we want to capture 3d images for virtual reality now i have a massive problem here because when we create a stereo pair the parallax is only recorded in one direction having said that traditional iMAX 3d films absolutely work very well in virtual reality particularly the shots created with a 30mm fisheye lens which gives you a view out to 140 degrees and if you undistort it and make it you know perfect and linear it looks absolutely stunning if you want wider fields of view we're back to using multiple cameras again and you can extract the images with this technique that's probably too complicated to mention briefly but you can create the two left and right eye images for the 3d there's just one problem you okay you could capture real world parallax by having your cameras six and a half centimeters apart but that same parallax is going to cause stitching problems when we join the images together and here's the thing no one has actually solved this problem yet as far as i can tell there may be a way of doing it in software using depth maps and horizontally scaling images and that sort of thing but no one has successfully achieved this yet for static images it's a simpler situation you can capture stereo pairs and the more stereo pairs you capture the less error there is between each image and you can stitch them all together or you can use sort of line scan techniques with horizontal sweeps as was done with sony's own cyber shot camera when it created horizontal sweep panoramas so okay let's say we can capture full 360 degree stereo images how do we record the parallax well certainly the convention would be to just record it in this sort of orientation so horizontal in the equirectangular projection this certainly gives you a full 360 degree coverage but let's see what happens to the images when we view them in virtual reality so there's an image it's okay but if you look closely you can see there's something going a bit wrong at the edges and if we look at what's happened to those lovely horizontal arrows we can see the problem the the the the parallax is in all sorts of directions now and it's going to be quite uncomfortable to view in fact the more vertically we look up and down the worse the problem gets the floor there is horrible and again if we look at the arrows you can see why in fact we're getting image rotation rather than horizontal translation so we're going to look at the rather than horizontal translation so could we come up with a way of improving that situation if you think about it in virtual reality you can you're representing depth with the photograph in two ways you've got the distance of the screen the virtual screen that is not the head mounted display and then the parallax on that screen which can be of course negative and positive and it's the parallax that's the bad thing that's the thing we want to try and get rid of so could we apply horizontal image translation to reduce the parallax from the source image and move the screen to compensate so i'll show you what i mean so imagine this situation where the zero parallax point is well a very long way away so this would need to be shown on a really large sphere and everything else is in negative parallax coming towards you well if you want to look at the floor what we could do is apply horizontal image translation to reduce the parallax and then view the image on a screen that's much closer towards us let's say about the distance of the floor maybe one and a half meters so this was our original image of the floor and yeah it's horrible and it's horrible because the floor is being represented with by an enormous quantity of negative parallax on the screen that's a very long way away so there we go we've just applied the correction so now the parallax is removed from the source image and it's shown on a much smaller screen the depth in the areas that were okay will still perfectly fine but we've now got a much more viewable image so it's a funny situation really traditionally with stereography we looked at having a fixed screen and then we apply dynamic calculations to keep the parallax viewable and we've sort of got the reverse process now where we're talking about using fixed camera settings but then maybe dynamically altering the screen to match the viewing conditions so that's something that is still very much an area of research there are actually some more fundamental problems with capturing images for virtual reality this one if you've got an omnidirectional camera actually where do you hide the camera crew in fact how do you even cope with the tripod and actually there's a more fundamental problem with um or challenge shall we say with virtual reality content in general not just photographs um that is how do you know the viewer is looking in the right direction how does the viewer know that there's not something much more interesting going on directly behind them all the time so that is certainly a challenge but having said that London Studios last year created a demo for Project Morpheus that actually exploits this problem and creates a very unnerving effect it's a shark cage diving experience now what I've done today is I've attempted to transfer it onto the screen for you but the original was all sort of orthosterioscopic and so on so it doesn't work so well you have to try and use your imagination try and imagine that you're looking at this with a 90 degree field of view with full head tracking binaural 3d audio and also bear in mind that what you're about to see is not a movie all the images that you see are being calculated and rendered in real time jay got something on the scope it's one big thing and it's headed your way stay sharp that's only gonna annoy it what's going on on As flavour bre, gwallas o hyn hefyd, nid i fostead hyn normalent. Mae chi'n ffrw mneud i'ch annes wrth�. Mae weithio hynny fel agoup playstation 4ここ akda hwnnw o'ch該 Le math o gwmpos,anner Draenwar i bro! cull gyda Llywodraeth Cynllun â uch chi yn sefyd! Lyw יw cywir ti llawer. Hel o'i c nhw f vaigon nhw'i dillard espawaid liir. ac romantic chwarae, neu ddych chi'n dda nhw rwyf. A o a fan wybod o y maen nhw i nyfgrifftraen yn haw passtxau gyffdomnol o'r cyfu. I fy modd o'rگur Osomur Ahmad wedi het edryried dyfroz accomplish a bod Mayr partisanhenol yng ng stakent hefyd yn siarad drân? Gweinio'r rôl yn ei bod chyma'r fawr o hynt i erbydd hi'n gwyseud ond westeain ac ar y pwysig iddo und grateis. I hi'n ei pan vi dweud o ble i'w gwy обычноon atio chi i'r ůmfaith ac erbyn gwy MEM gyda'r hynny sy'n credu o'r nfrifadau mleidigol filmoplus gweithio'r eich ymgyrcoffor grassamelwyd. Gall dweud arall, honnod, Ramen yn storiau gw Schuleul D Lan Aro. Felly rydyst Freedom Lām Class�를 mi lle'n armad am siwn agm 부드�adeau. Ar dradd 말 gyda fy vonedd nad yna ydych yn остek yn選 heel inni. gyda'r ysgol yw'r ysgol yn ymgyrch yn ymgyrch. Felly, ddodd yn ddweud. Ddodd yn ddweud. Mae'n ddweud. Mae'r ddweud yn ddweud. Mae'r ddweud yn ddweud. Mae'n ddweud o'r ddweud yn ddweud. Mae'r ddweud yn ddweud. Mae'n ymgyrch yn ddweud. Ddynaf, os gallwch yn gweithio, mae'n dweud o'r ddweud o'r ddweud, maen nhw'n mynd i ddweud. Ddweud. Mae y ddweud. Mae'r ddweud. Mae'r ddweud. Mae maen nhw addi, restorerusolwg pleulu hefyd cael想 chi am ysgrifな â'r yolkset לma! Rwy'n cael bod ymhell mewn was Ngath Fydd y cwestin景 wel ar y briffwrdd ein boblau c dizer race sy'n arnesedd ei gelynneu cofain Rydydd ac yn ystêtLike y starau entertain ar hyn enwedig gan yrdych fel ys beth tu'r beisa fivek carefully Fe της y ddefnyddio Roedd anodau strafyn That Sabot Le wnaeth y gallwn ymddiffosio'r eu wlad принyn o wng lefteg morstudion yn tentuaint —多 mwyn i aroloughno i'r Saen heligh詛 am gyngor Llywodraeth. Fally ac dweud hynny'r llyff na eich gyneddodd, ond hyn o angen i'l eisiau ailty southlwn i'r staff a fl одномn tymst pan chi'n dod ym infections, yn beth sy'n eu ffrindulion. Por raddodau sydd oedd ein besyddio wrth yатаen i minorities i vynyng ymddangod eu bod yn gwe nas gondol i'r ddigon paranoido'r raiff ynogi. Sen tynnwys pwysgyntio wirwyr llwe� i judgementu o ddefnyddio, a hynny'n addig i ddyflu ai ddim yn enwedig o yn головol. femen nhw fydd poddu, sy'n dd studun i ghrawat, ond clwrs ddegon heterosiwyng i ni, y gallwn gwneud yn ymweld i'r ffordd, fel ydy'r ffordd. Mae'n ymddi'r cyhoedd, mae'n ddweud yn ymddi'r cyhoedd a'r cyhoedd yn ymddi'r cyhoedd yn ymddi'r cyhoedd, ac mae'n ddweud yn ymddi'r cyhoedd. Felly, mae'n ddweud yn ymddi'r cyhoedd, mae'n ddweud yn ymddi'r cyhoedd. Mae'n ddweud yn ymddi'r cyhoedd yn ymddi'r cyhoedd? Yn y moment efallai felly fod yn ymddi'r cyhoedd, felly mae wilde d piss. Mwнеad ar agarfer i ddweud, a Chelyddoedd H.I yn ym 960 x 1080, a berth gynunol. Beth Cymru yn gai iawn ym 8 yn ymddi sydd o'r lefod i wiriad y WOW yma yn y clwy. y pysl yn y cender o'r cyfnod ymlaen o'r cyfnod ffordd ymlaen. Mae'n meddwl ychydig yn ymdill. Mae'n meddwl yn ymdill, ac mae'n meddwl yn ymdill. Mae'n meddwl, ac mae'n meddwl yn ymdill. Mae'n meddwl yn ymdill. John Merritt, I want to congratulate you on showing this audience one of the most beautiful uses of stereo in a presentation that I've ever seen. Thank you. Thank you very much for your excellent presentation. And I have one question. In your slide, you mentioned that the head mounted display possess a much greater comfort zone compared with the conventional stereo scope display. Can you explain in more detail? Could you say a name and? I'm Liu Yue from Beijing Statute of Technology. Thank you. That's a very good question. I wish I was an expert on this. I would be able to then spend the next half hour explaining that. I mean, I say, you know what one reason I suspect is to do with being close to author stereoscopic depth. But having said that, I'm not sure that is all the all the reason. Maybe it's something to do with not seeing the edges of the screen as well. You know, you've got that the window, the stereo window that's very much a point of reference on a conventional screen. You have to be very careful with. And there is no point of reference so your eye doesn't really have anything to lock on to see it can sort of lock on to to any distance. And, you know, it may be something to do with that as well. We, you know, this is a classic example where there will be a paper out there that explains all this perfectly. And there we are with, you know, we should know, but we don't. Any more questions? So Ian's going to be here through to Wednesday for the discussion forum. So you can grab him at any time. Yes. To the round and asking more detailed questions. Otherwise, we're back here this morning at 10.50 for the session on 3D camera designs. I guess one more round for Ian's excellent presentation. You.
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Ian Bickerstaff from Sony Computer Entertainment gave this wonderful presentation, which discussed some of the interesting technology challenges of presenting stereoscopic 3D images in a head-mounted display in anticipation of the upcoming release of the Sony Project Morpheus VR headset. The presentation was fully shown in stereoscopic 3D and used the 3D visuals to maximum effect to give the audience an "in-depth" explanation of the topic.
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10.5446/21828 (DOI)
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So I chose the titles today, what is stereovision good for. Obviously this is a conference on stereoscopic displays and applications, so we apply stereo in many different ways. ac wnaethwch bod wedi ddim'n windingdan ffrindull gan freight deport sound.....y triedo ffannaethio, qualu mwyaf am ymdd glenciaill? A llun yma yn Ard RhyMyd. Fyddwn ni'n golygu am ddifolwyd i waterfodaeth cysyddion warnedol yng ng不錯 yma'n gwybod mewn ped紹.....<|ko|><|transcribe|>.. Felly yn ddyliau gweld, rydych yn dlethau cifs foodioli. Mewn rhoi cins gweld a theodau gwahn ond, yw meddwl cifs foodioli. Da mewn r'xbeithnu, y dweud y dweud y bus pHs mewn dm Berfaith 2 Mae ein Penodol drunivers o'r uch gimmŷu rylech gfyrir leolwg CYs panballe go Pakistan iiana iawiau sylfaan arall leanzaa. H delta wans sicrhau yn ei ddweud mae mi'naster sig mwyth Ac het yn yr diwelf..lawn y zeol tussen. Dion gallwchneg, ond ingen am ry 어쨌든au diwyddiant ymburstud Paen бытьpario weithio ar gy stuffs dilbaru o ringau y C frankly industry lic unsarts beth yma....dyn allyn o'r cym UW and Jones an tier logwr ac maedoline fe dyl stabilize sy'n ei hun y confusion. Gwis. Paedwch y lleon sy'n eu hyn dor maen nhw yn juadgol i Andrew i dod o fod yn rhan beth sy'n bob i amdylch yn C relations Gwis geisio yn maen nhw hefyd. Roedd ni fydd gennym ni'n bir lluniau mewn i siadas, o ddech arrÔd mewn henariad petiool, ein bod an<|ps|><|transcribe|>�Inl math ydydd? Musiariaeth yn cy pubanc, ac yw'r gwneud y roedd yn morio bob viw creating ac gynwys i chi'r arian neu, yn ymddi cERS, i 특히 steliolaeth mewn ni tan morio, ailgofas yn y casio seithio oos lideri experiencedu econominiol. Felly, Ty?reu gen Chemi Caernau DYL Hajaf y Gwylion? Vo'r cyfan Clinegrif Saudi Llynyrdd? Rydym i ymwybod wr hisl mae'w cyfan ein hyfer das i ni I canelt cyn angles pen bottom tan lle chi'n ddell Un i rhan o hyfnwyd llyddu o boid i seitorediaeth ar y d نہیں זהu siŵdd dipynisió a raen feddwl chi fremodd, backing out whedin Neil� pop<|es|><|transcribe|> letter a ble обroad hinges na imeddoli ar gyfer Assistantblăng yn oed. But the real vision of humanity is rather bad at tasks like this. We call that absolute disparity detecting the depth of an isolated object. It's not something we are very good at. And so more recently scientists have emphasised the importance of stereo vision in camouflage braking. This is an idea that really goes back to Belly Joolesh, the great Hungarian scientist, gyffchem? Dyna, ein bod eich tenors iawn i dod am作wyr uchric lisri fy morlau ofteniktor i'n teimlo sydd yn enw yn gweithio. Mae gefnadwyd i gyfle f simplified i gyfle symaogi fel y d channels rockets. Felly mae'n gallethid drebabny temporary ar하는 deddiol dddStill Trinll, ond wand yn i gwCDG. Mae gennym iawn fy neid o ffrasid gynydd. Ar gyfweg cave', ar謝謝 i gyfer those of you who have and the glyph glasses with you I'm hoping you can see a circle a disc hanging out in space in front of the background I see people at record of glaces there so I'll give you a moment Why are the glasses are handed out actually... I just go back to the monocular images so what i want to bring out in this image is the fact that the disk is not present in either image monoculare, none of you will see a disc in this pattern Siarad oeth ddim yn d McN巧 i gyddowydd gallwch anolwy bobl. 그럼 y fyn hyplaid에is y fных ar organizations ll confidence heiddiw<|nn|><|translate|> Im ydych chi'r ael anhygylch pyamarraethu bydd Tradwyd yn cy倍 ddim yn cael ei mynd在ethitarianiaethon. Yn ads тонne, fyddai gwzgrif advantagesASHBraP tynau, yn oed yma wasbl, fel hwn derbyn fe ddim a wych sadness a intrigued her doedd tyw roeddaeth yn dda'r預idio reports bobl hogy dysgu at tal Machine During a book published shortly after First World War Major Ives of the U.S. Air Force związeth vogell o graduated a leave predictor, Mütterwil Ad qualité stori o ph captur a le printed Gwch surjef am hyn Gwymadd tyw i y scôpe feddordeb yn f haber politicallyuneumbur ar y cant. Folders ond gallai amser o flynyddoedd Fyr complexes ddeicomai gan mai defnyddoed i fyarrットio yn gwer'w peinto rydych chi iddo i am puto'i. Dru 1998 yn dda니 yma, i fod ond, applauds iawn Murfer, ŷwgwraffwyrheni. Ar ddayeth drwyír mithe, bob mthZZ teithas i bethabe deall at lle i dda yn Llywodraeth L Cornwall. Nawr lle ti lidi Cabinet thorf! Yr uneduaod y lle einrhau, Fe wneud alsiwn genpeddilins yn ei ol أال ac os ma magnets 我llawer y mae Dau Chymreidé ac ar eu leıkydd und competency, a яa fe bra fug mwych gwynhau o ddeithasig o lechyd hy festive objektau ac gweldio, maen nhw'n meddwl i gael'u cael ei Skyr unbox archiforiya? it's a stereo vision should evolve. I mean, do my many other cues that give us such information… information about depth. Of course, we have perspective cues and occlusion and shading and shape and texture. All the cues artists know how to use, motion parallax even for camouflage braking, the absolute depth measurement for humans. As I mentioned, we're pretty bad at it basically because it requires the knowledge of eye position and it's computationally very expensive. oes ychwanegol ni. Felly mae'n adeiladau na no Visio Cym yummyег. Mae hymysgol f reproverio o gyllud yӴ yn gorfu grants 고命ach. Ymмаes oeddiwol yw 1920 heddiw fod yr ythmiwr.<|ro|><|transcribe|> Cyn Lot mondiad acain~? M-s ines? Cus arno blends, d Hook disseb yn yr un gen설o y mámu? Ac, bydd Pokémon yn o equilibrium, hisd hynny ball ceisio wrth ar y gwleiddiad a ll classical a Ballggell, � wahanol hithel iddins ac sukabout. Darall hopau ein Doslenig wedi gweld y cyfeodio caehysau a chyfodioFirst-roedbatau. Yn fidelity ymrśliwyr, bydd ydw i ssiwn s Joshau, Drylawll i dd spotu, y genddiol yn gwanfa o dravidgyn o' реш sacredu ddylet tra Gorginergyff和 Rel seized fel mansionall, ond الج challenging er fwy ddiddordei lu dda'r f clamp Rhyd ar Fan oldd Wedd Dunedd andoedd, ynnal ar gyfer bod ar d année alla roedd ac bod holef yn huniaid yn feasible yn dod ar Un Lady ac mae perloed fearsau perth yma y gall hyn ddych yn byw yn ddiddod â phrann ar gyferiver oise Yeist, mae gynnun y filyd yn gweithio ac yn birci gyda am—— ddeithas draft mae gylwys wyrdd wedi'u'i r tua gy Tech ac mae gweld cyntaf sprith allan iall o otwnais geirio, finanfiad responds ar y bai, ac wrth analelly o bot estàifall y w exactly dy nid yn cael amgarraith. Felly fel o'r cysteineis iawn i gyfro relio o'r miron o cyfro fydd o linegen ikrhech cyfar 그렇지 yr bobl h diddlu iawn. Dyna bod am Yorkshire Earthll. Felly y developing Run Wryll rôl ei bryi ar arfer ond ermliau phoedd角ad r privacy captain i weld ans chairman<|sv|><|transcribe|> sahbarnas i en<|sv|><|transcribe|> min ö 임håll å dan y förr och tot peaceful rOWen y. Anna Exnt Pismo obeynus luckad st a gilych yn llweddau y hai kengyn rowannu. Ond ydym ni integrity gaidd y gallwn weithio yn eich eh 유chs neu gyf兒干, ac draws Lord HOWARD yn y gallan hon shift, haner rydych chi'n wmp거든요ai ble yn cael peth gwroes. Y cryf yorts Sin chyr紹 yi'r marill Odyn, beth uniqueid am y r See Panc. Felly, mae'r rhagfennau yn gynchionrhywseolォr� i arbyn nhw in primates, ar jeffan tw floatul ni, ac mae'n ych hiçbir hi攢 without the prime from its primates is it because there is no idea that you comply target how S a議urmiadau kin semraedd yn lle nawu umbustud enw yn dweud deby ngollやnt. Nadiwch,ys Gymellarachiaid Smud<|hi|><|transcribe|> ant気 Iendwch weith lowering 21 ac yn edrych yn neb yn credu maen nhw онeddanges Wel hun ti wnaeth celydd yr eisiau Realwch fel y rhan cywlau bpen a is gwych cyd- quietlyd ryw g Button Dyf i have nowod fy tEL Is gan nesaf rydw i het Nog dyn nhw ni'n dweud pob hen But mae bydd ar lect fel y faslwch dใช yn mawr yn Fen chi Fyrgy emphasizing flagship di fabric a hyn ddelineid â'n peudo천io sefydlaent,ech gyrgyrchery Birds virus iawn i ddwylo ff Jason iiana lfroses a fx iawn Ready wanted asylania, ac mae his y gallwchross gweld unrhyw farsnod a lwyd였 mwyn o bobl hwn beth byr graferation iawn. Cymhlyno ehau, mae holl Genes Cyddebyryd ynran am bod yn שמ�ref iawn tan yrockidd Active Doctoral Research Associates nodi dlwyd ble f кого yw ddeall yn des débutio fel rhai cysylltu yw hynod? Oed iermoddCK môl ynglyn hwtled yn lleol arDavid deadlymences. Roedd rydyn ni wedyn druni'r hygau cymryd adewanol byn o bach ynglyn hwn yn d� insteadw iddyn joc ac hynny'n meddwl byr yhwng 101 overwhelming 11 at eudorant pan eich urthyn i ni gefn MI ond fydence Polise mewnr tu ady här Sarah i gyhoeddiaeth Aujourdi fel ameliar y Confer Mae'r dwy iawn lodge am unig wedi cyhoeddiu Pwysigfyrd Trunod, strongest... fowyll ryw coud a eriaeth rydyn ni'n iechyd o Dop i brobl Dwi tychnion am fyddwn i ddim chwarae fydd o bobl findl oheramentos kadas sy'n rapwyr glywed am digon a'r rhan dweud Mраз o hangi goif, rherwydd hopping iPlease Boen, yn d 완전 swad am gyhoedd Repwyr yn ddedig Mae parwyr ar teknoed So rherwydd gelio adnodser Mae'r rhan f telefon d Mae'r rhannu ar bike yn y ffr的是f comparisons a nhw<|sv|><|transcribe|> Funyadge ymbygder arna i o óll modify Far o'i tål yn speeds blade I ond wedi gweld am fief ar hyn. Ond pam hynny'n eu bodasu bod wedi cyweddor iaithr 50 yn gyda dimfestwn yn gei'r esseid? Pry occasions o ran alsою fyddwyd arbennauти a Oesética sydd wrth uwch am ff containing yn di ac roedd e gan angen i fyny που u interests i weithio at jydyhu'r rhaib rhaid oherwydd tej Yeahan y Llywodraethau hyn. Rhaid gennyngon i'n dda'r hun, y gallwch yn qu 사실f arch 클�ereif er etherew?<|ko|><|transcribe|> Se Allian Chancellor memes ar hynys yn cyflawn i. Eb mewn e comparein hefyd ei chy modoo am fod yn hawdd a dryd halu ddwych. Rwy'n rhyw gael i chi ochr eu topo'r lonent ag y future is deall pwy sensei o cy hamladau��'r lnanton O'rohl tramfli faith, lle arill mor hanon ac yma ynghylch yn y cyfle ac nשawd o'r ôl pan o'r sgwr after mor aynı achos mae'r throne, symlong mymlid gym Je tel os y mae'r od mixed你在on o amlyd settle Si해 mewn awtol ingen gyntafol mewn m wallpaper. Podeonwyr garden o lle oлы Yongaf. Wedyn dod acordích gydaherau wentysidd. D feddewch chi chi would see hyn ystod wentysidd. Y wrth wneud モwasiant gwrs gan unrhyw ddweud y camera. Lydy't bydd angen gweld y gwaithiant gwell y werthdd y mas daddyen er yn yw'r sglo SNG o'r lwynt. Y mas dat retrospectudd ma' extracted dan she'r wneud. должен nes dewithwyr er ohydig rhywun i dufodod yn lleion o sunglasses Yn ardu ymysgu hyn, mae'n cael y f Lunaquid yn Chym ejemplo<|la|><|transcribe|> Cy philosophers café Lost Rock yn cael hyrchwil ar y cymaint, ydy'r rhag feature. Mae'r rhag Phoenery wedi rhoi bod yn gyflysio fel e carrier oed chi, 않고 o hon stimul司 Iolnawn ie inspector, yn credu w apply o fair give, o accord ذe y finflammus ddyn nhw'n credu o datPIg 변 o bern babeisau, calib yn aleisio morichiol.olaeth yr ystod yn drych gwybod. Fe GitHub puts yn ei bcherach hefyd. Rydy'r ystod pearnade y rhai ecsefar o phrod inventario. Mae Gwneud Subamiog yn erbyn am allan dieteb honi, yn lost недle ar ôl fried mewn, eu bod multimodig yma yw bod chi yn cael ei myswng o bwywr dim. Y ceful hwindwhoened rhagledau de 와ad yn yr hyn wedi'i leachu a chisgwys a chwein.... Rydych chi'n bwysig fynd i'i gweld sefydliad og yn tossedionol newlyt. is aаем dim e'n dantes arôl. Fem yw estoyте ddim i fe fry Pressure inch sized eu ffister fydd yn rhan i'ch grwyffyle gweld刵ydr Cell Ynni wedi ar draws findeid yw cerd, nad yw ddermes a g시면 снysgydd nes â ddweud sy'n bed i borth i fi'r ddetebycy已 ac mae'r hwn angen hi yn fyny ar lawer lle Gen yn gwneud ym!... D tor donnéwyr ei gwle sudd ymar sacruch hawdd yn ôl D teaching Hiseterwyr ook am rhaid rydw ichonbetref wedi gweld eich gw��요 Ond hyn full yn cyfrifau Hin uchreal ni'ch обnym yn seis mateig ymlaen, a dpathbwynt yn drwy' at果言 y tro daddiw i r Cook yn y roedd oherwydd unrhyw daeth yn y cyfrifamen gyda'r hydrif dangos fel y gymaint i'r cyr existingio. Ba whether the student coded that the manока was moving right from the other camera we could see that's reasonable. Rings NZeg w central y llwg y playlist Fer hitd pan hynny astud yn meddwl知 South East D yma samosion gyda'r sovereignty blire. Rhyw berthynas gawneth amplify f5000 newydd o� degur mew, but interesting lythydd efallai felly bydd y gafynnwys pe Rydymeth, dyfedd yma, gruposio'i gwahog ar gyfer y students y synd yn roi neudio'i edrydd i din python Drawmer Y úrmer yn lab! Dyma', yr thawdon gwahanol SeaMount Llywodraeth yn elles notes, hefyd yr Machine up yn y learnt oedd beth edgeson плwynt nid- spoiled bydd yma. Fe decide'r queen cyflosydd iawn i chef o gallwch arfer gen i âенняu yma Лreif y нетr ales yn logo. interim. Cydydd y blyda goll banking yma o gwz entraedb hyfforddiad Ondd yn y ddoch i'r ddau phall i atydd amddangos nid i bod yw ymddangai enter whites mae'n fjaz ei hwn yn ôl i g簷r 물 is y ddau'r f<|ta|><|translate|> 41nt oed addorr welding mae'n 20 aet ar gyfelydd�� released turner os bobl yr sg collanc, bobl a'r Kerodyng iawn y guides tu du cynoeth nysgr, illeg wedi myfnod i g простェ pressured a er melyt ysgrif iechyd-i'r g limbs ac yna unrhyw b nails y mae rhamiantus am pan wnaeddo fel bod yna yw methu rydym erwa Gracias Yrgrond y cyffredin iawn y tyn Gymraeg chi shamil Rosl rhun i gnetwnr, er hynna nedってる mewn ddechrau rydym wedi'u affiliate I did this in a really beautiful series of experiments. The first one, this was published in nature from 1983. What he did was use the fact that this particular species of mantis would catch flies when they're 2.5 centimetres away, so within the range of the mounted spore arms. Russell, as many others had speculated, thought this might be because the mantis is working out that the flies is within range when the binocular disparity, so triangulating back to the two eyes, is a particular value. When this angle delta is a particular value, the prey is in range and you should launch the strike. To test this, he put base out prisms in front of each of the mantis' eyes, the point being that these prisms bend the light rays. Of course, the mantis isn't going to take account of that when it's interpreting the visual images. When the prey appears out of range, the mantis is going to think that it's really within range. Sure enough, that's what Russell found, that with the prisms in front of its eyes, the mantis would release its strike at inappropriate distances. He varied the strengths of the prisms and demonstrated that the pattern of errors was exactly what you'd expect under the hypothesis that the mantis is using binocular disparity to judge the distance of the prey. This was the first proof that at least some insects have stereopsis, so a tiny insect brain is capable of doing stereo. Russell did three or four papers on this, but then really the whole thing just got abandoned. No one has probed in any detail, OK, well what exactly can mantis' stereo do, how does it work? This is a question that really interests me. I've spent most of my career working on primate stereo up to this point, but mantis' is of certain attractions for start their brains about three millimetres across, and it only has a million neurons, a million brain cells. Whereas if you're trying to study a human, we're just orders of magnitude more complex with around 100 billion neurons. So it seems like you should be able to make much faster progress studying an insect system. I'm interested in insect stereo in its own right, of course, I think it's a fascinating problem. But I'm particularly interested in whether it's going to turn out to be broadly the same as the stereo that we know from vertebrate species. So I think it's really interesting that actually stereopsis in primates and stereopsis in barn owls is incredibly similar, even though we believe it's evolved completely separately. And so if insect stereo is again like primate stereo, like owl stereo, then I think that will be a very strong indication that there really is only one good way of solving this problem. If you want a stereo vision machine, it had better work like this. And clearly that would be a very important thing for us to know from machine stereo, if nothing else, and it could lead to new insights in understanding the details of our own stereo vision. But of course the alternative is it will turn out that insect stereo is completely different. And that, it has to be said, is the current orthodoxy in the insect vision literature. That people assume that insect stereo, because their brains are so much simpler, must be much less complex than our own, can't do things like camouflage breaking. And if that's so, I think we ought to know about it. And for example, it could inspire new algorithms for machine stereo in situations where you don't necessarily want to mimic a human's perception, but maybe you simply want to guide an autonomous robot. And the priority is having something that's computationally cheap and low power, and clearly an insect is going to be a good bet for that. So I'm afraid I can't tell you the answer to that yet, because it's very much a work in progress. But our starting point, in order to test whether insect stereo can break camouflage, we needed a way of presenting separate images to the left and right eyes of the insect. So the prisms that Russell used were very ingenious, but all they can do is shift the left and right images, so you can't possibly begin to present a camouflage 3D stimulus with that setup. So we needed a different one. And our attempts to find a solution attracted some interest. OK. So, yeah, everyone seemed to be very intrigued by the idea of fitting 3D glasses to an insect. And just to explain what we were doing here was using just a standard off-the-shelf patterned retarder circular polarisation 3D monitor. And we took a pair of the glasses and just cut the filters down to be the right size for an insect. But ironically enough, this attempt didn't work. So we've tried many experiments to try and demonstrate that it was producing a 3D image for the mantis. And yet none of our attempts worked. And we think this is because there's excessive interocular crosstalk between the two images. So as you can see from the films of the experiment, we're putting the mantis close to the screen, we want to fill its visual field. And that means that necessarily it has an oblique line of sight to many parts of the screen. And as you'll know, if you've worked with these types of monitors, they're very sensitive to viewing angle. So even though they have quite acceptable crosstalk when you're looking at them straight on or at their sweet spot, if you look at them obliquely, you do get substantial crosstalk. And that's our only explanation really for why the mantis never responded as if they were seeing images in depth. So I'm going to move on to our second attempt, which is working, and that's using anaglyff glasses. So the old style red-blue ones. And of course, these are hardly ideal for humans and they're never used in cinemas nowadays, for example, because they have this terrible colour effect that they're going to destroy your perceptive colour in the movie. And that's because humans have got three classes of photoreceptor, or four, but three cone types. So we're able to sense the differences in wavelength between the images coming through the blue and the red filter there. But rather handily for us, mantids, amongst all their other advantages, are monochromats. They only have, as far as we know, one type of photoreceptor whose spectral sensitivity is shown here. So you can see they're sensitive mainly in the green. They actually have a little bit of sensitivity to ultraviolet night, and they basically can't see red. So we decided that for mantids, the best thing wasn't red-blue glasses, but green-blue glasses. So we designed some anagly filters for our mantids. We got a monitor where we tried to find the biggest spectral separation between the three colour channels, and that's shown here. And then also, as you can see, the blue and the green are fairly closely matched to what mantids can see. So if we, with our spectral photometer, if we record the output of the monitor through a blue filter, you can see we essentially get no crosstalk from the red and the green channels. It's all happening at very long wavelengths, which the mantids can't see anyway. If we view the output through a green filter, we do get a little bit of crosstalk from blue, but it was the best that we could find, so we decided to test it out anyway. So what we're doing now is using anaglyff in this cyan-blue-green sort of space. For example, to display our dark bug on a bright background, we draw the background in cyan-blue and green, and we draw the object for the right eye in blue and for the left eye in green, and then the mantis is viewing this through the coloured filters, of course. So what it's seeing are these images shown here. So both eyes are seeing a dark object on a bright background, but the position is different in the two eyes, so we're able to use that to simulate depth. So our stimulus now looks something like this. Again, it has to move and spiral around like that to attract the mantid's attention and convince it that this might be an insect, and the screen parallax that you can see there we can use to manipulate depth. Our experiments show that these 3D glasses, halleluwia, finally do give the mantis the illusion of depth. So to demonstrate that, imagine that we put a screen at 10cm from the animal, so that's a long viewing distance from mantis, and they will basically never strike at our simulated prey when it's that far away. They know it's out of their range, and I call that zero disparity, meaning zero screen parallax. But suppose we have the screen at the same distance, but now the screen parallax specifies that the simulated prey is 2.5cm from the mantis exactly within its catch range. Now the mantis will strike on over half of the trials in which we present that, and I should mention these are all interleaved, of course, so that from trial to trial the mantis is seeing bugs at different distances. Now if you're sceptical, you might be saying, all this shows is that the mantis will strike when there are two objects on the screen and not when there's one. So the important control for that is to swap the screen parallax. So now again there are two objects on the screen, each meant to be visible to only one eye, of course, and the disparity should be telling the mantis that this object is a very long way away, or indeed impossible if the rays diverge. And sure enough the mantis never strikes under these conditions, and here's the data for that from several mantises and many experiments. So you can see that when we have a normal 2D image on a screen 10cm away, the mantis is basically never strike, but when the image is still on that screen, but the disparity simulates a virtual object in front of the mantis within its catch range, then they will strike. So that's great, so we've basically now got a 3D cinema system for a mantis, and now we're able to ask questions about what can stereo do for mantises, how do they use it. One of the questions that I have a student examining at the moment is asking whether mantises use their stereo vision to calibrate the perceived size of objects. This is an important question for mantises, obviously they have to catch prey at the right distance, as I've described, but they also have to be very sure they only strike at objects of the appropriate size, so clearly it needs to be big enough to be a tasty dinner. It mustn't be too big, I learnt this the hard way when I once put a locust in with a mantis intending that the mantis would eat the locust, but when I came back in the morning it was the other way round. So clearly striking at excessively large prey has substantial costs for mantises, so one would imagine that they might use their stereo vision to help work out where objects are, because of course the reason this is a hard problem is that the angular size subtended on a retina depends where an object is in space, and this can be non-trivial to work out. OK, one last time. These are small, but the ones out there are far away. Small, far away. I forget it. So we're asking basically whether mantids are cleverer than Father Doogle in that sitcom, and whether they can use their disparity to figure out if they're looking at a large object up close or a small object far away. And of course we're also very interested in whether they can use their stereopsis to break camouflage, so if they have a prey item which is on a camouflage background, and that's a very realistic situation for them because they're hunting objects like crickets which are camouflaged, again, it's the background of grass and leaves, can they use their disparity to help break the camouflage there? Well at the moment, as I say, we don't know the answer to those questions, so watch this space, but at least we now have the mantis 3D cinema which enables us to find out. So I've mentioned some of these uses of stereo vision for different species in evolution. One thing that I think is very distinctively human is the use of stereo for reproducing reality. And so in my overview I gave this a title of what is stereo good for in art. Now I realise that art and reproducing reality are not exactly the same thing, but there's a substantial overlap. I think especially in the western tradition where really ever since at least the ancient Greeks, artists have been obsessed with trying to produce realism. So Plato writes about an artist who was so talented that the very birds would fly down from the sky to peck at his painted grapes, and this is clearly the height of artistic achievement. And then in the Renaissance they have this huge breakthrough where they realise the rules of perspective, so how you can project an object, say this cube, onto a flat surface and then reproduce exactly the image that an eye would have at that particular viewpoint. But of course they also realised there was a fundamental drawback with this, and this is I think Leonardo da Vinci was the first to lay this out clearly. That if nature is seen with two eyes it will be impossible to imitate it upon a picture so as to appear with the same relief, though the lines, the light shades and colour be perfectly imitated. You can never make an object appear in 3D, you can never really reproduce reality on a flat picture plane because you can't ever perfectly reproduce reality for each eye individually. It just can't be done. So Leonardo realised that but he didn't of course stumble across the solution. So for this reason it's again been known for a very long time that 2D paintings look more realistic when they're viewed with one eye. So this is an image of the famous Brinleschi peep show where he painted a particular cathedral in Florence very realistically with all the right perspective cues. And then arranged for people to view it monoculally through a mirror and this apparently although the picture has been lost to us, apparently gave an astonishingly realistic perception of depth. And you can imagine why. So with one eye you don't have the stereo cues that are telling you this is in fact a flat picture surface and you can rely on the perspective cues that tell you you're looking at a 3D object. And it was kind of remarkable that it was only in the 19th century that Wheatstone came up with the idea of actually simulating images for the two eyes separately and presenting them separately to the two eyes. And of course people were amazed as we heard in Ian Bicastar's great talk yesterday by the vivid percept of depth that Victorian stereoscopes could produce. But despite that breakthrough, stereophotographs still face the fundamental limit of all perspective painting or 2D photography, which is they still only work from one viewpoint. You can make it work for both eyes, but the eyes still have to be in a particular position. And so when you view not from the correct position, then images appear distorted. This image I found on the web of election campaign posters for Frederick Reinfelter in Sweden's election campaign last year. So it's recognisable, but the face is kind of distorted and elongated, squished horizontally and elongated vertically compared to this image of the same guy taken in the conventional way. So presumably you will see that. But actually that's kind of remarkable because when you think about it, this room is rather great for demonstrating this effect. It's a very, very wide room. And so many of you are going to be viewing the screen from extremely oblique angles, actually probably as oblique as the camera was when it took this image of the posters. And yet you probably don't perceive this guy as very distorted. I must admit I do for where I'm viewing him at my incredibly oblique angle, but many of you won't. From less oblique angles, the image will look completely correct. And so this is the strange thing about this viewing distortion. If you photograph a poster from the parallel to the film plane, so as here, then the image will look correct, no matter what angle you view it from. So this is hopefully looking non-distorted to pretty much all of you in the auditorium, even though you're viewing it obliquely. Whereas if you photograph the original poster obliquely, then it looks distorted from any angle, even if you happen to be sitting at a position that corresponds to where the camera was when it took the photo. So in other words, it seems that our visual system is able to correct for oblique viewing and kind of reconstruct how the picture would have looked to us had we been directly in front of us. And I guess this is essentially why we get this effect in photographs, like Uncle Sam here appears to be looking and pointing at you, directly at you, no matter where you're sitting. Because we somehow mentally place ourselves directly in front of the image. Now this is really quite a remarkable thing that we're doing here. How can you do that? How can you work out where the picture plane is and correct for it? Is it something we learn to do through experience with pictures and photographs? Or is it innate? Now a lot of, I should say, I owe a huge debt to Marty Banks here and his great papers on this topic. And in one of his papers, they put forward the idea that actually this may be an innate mechanism, or how can I put it? Not one that depends on seeing pictures. It's not one that's developed specifically for pictures, but is useful in interacting with the world in general. So for example, if you see this image of the coffee cup, we'll perceive that as a circular coffee cup, right? You actually have to have a certain amount of artistic training in order to even recognise the fact that actually it projects to an ellipse on your retina. So if you ask a child to draw this, chances are you'll get either a cross-section or a circle. You're unlikely to get an ellipse until they've attained a certain amount of artistic sophistication. So maybe this is the same kind of ability that helps us to see, to correct for a viewing of pictures. But then when I got thinking about this, you start to realise that actually this may be this important mechanism that ensures that cinema's movies on cinema screens still look pretty good, even if you are viewing them from an oblique seat in the auditorium. You're worried that 3D may mess all this up, because of course you can only do this if you know where the screen plane is. I need to know, for example, is this picture drawn on the floor, or am I viewing it standing up in space? It projects the same image on one of my retinas, so I need to know where it is in space in order to figure out how it should look if I were viewing it normally. And disparity can be an important cue to this, of course. As I was mentioning, disparity can tell you where surfaces are in space and how they're oriented. So if you remove that by doing a 3D movie, where now the disparity on the screen plane can be anything you want it to be, have you just messed that whole thing up, and are people going to be much worse at correcting for a viewing? So my PhD student Paul Hans has been looking at this. Basically what he's done is compared two different renderings of a cube, which I'll show you in a moment. So he's compared rendering a cube in the normal way for viewing 90 degrees to the screen, and that's the red cube over on the right. And then he's also compared when it's rendered for a bleak viewing. So, for example, at 45 degrees to the screen here. So what I mean by that is we draw lines of sight through the vertices of the cube and see where they intersect the screen plane, and then we use those to draw the cube, and that's the blue cube over there on the right, which hopefully does look kind of warped and distorted to you. And then he's asking people to choose between the true renderings, which looks better. So clearly a cube that was rendered for 90 degree viewing and then viewed at 90 degrees should look correct, right? If it doesn't, something's gone wrong. Now, what about something that was captured at 45 degrees and is now being viewed at 45 degrees? Well, it's geometrically correct. It's creating the same image on the retina as the original object. So it should look correct if it weren't for this compensation that we do. Conversely, something that's captured at 90 degrees in the normal way and then viewed obliquely, it ought to look distorted. But as we've seen, things often don't look distorted because human vision is able to compensate for the oblique viewing, at least if you can see the picture surface. So Paul presented two cubes, as I say, one rendered in the normal way and one for oblique viewing, and asked people which looks better. I've got an image from his experiments here. So maybe I could have a show of hands. Who thinks the top cube looks more like a cube, more normal and less warped? And who thinks the bottom cube looks more like a cube? OK, well, we have a sizeable proportion of don't knows, but we have, I think, a strong boat for the top cube. And it's interesting to me that the ones who were saying, no, the bottom cube, I think without exception, they were all over on this side of the auditorium. And that bottom cube was actually rendered for viewing at 45 degrees in this direction. So you might like to experiment viewing that bottom cube, say, making a tunnel through your hands and viewing it monoculally. You may find that it looks much less warped, especially if you're over on this side. And conversely, the top cube may start to look somewhat compressed to you there. So Paul showed people pairs of cubes like this and just asked them which looks most like a cube and least distorted. And we were able then to analyse that data and work out whether people were still compensating for oblique viewing. And, somewhat to my surprise, we found that actually people were still able to compensate for the oblique viewing. So even when people couldn't see the edges of the monitor in order to work out the angle at which they were viewing it, they appeared to show a very similar kind of compensation even when the images were presented in 3D. Now, it was less robust than in 2D, which is what you'd expect, but it wasn't abolished. And I found that intriguing. I'm still not entirely sure quite why that was or how your visual system was able to do this. But certainly for the 3D display industry, it's good news because it suggests that shape distortions due to oblique viewing, even though geometrically they should happen, are in fact unlikely to be a major problem for human viewers. And if you want to read those, then we have two papers on this experiment, a pilot experiment, and then the main one, which are available. An interesting question, I think, is whether the extent to which we'll learn to watch 3D. So I struck recently by coming across this comment from Ernest Gombrich, famous art historian, and he's talking about the relevance of our viewing habits to the perception of pictures. He says, one reads in older books on photography that the distortions which occur when you photograph architecture with a camera pointed upwards, for example, are intolerable, but we've become quite used to them, except without demure, a monument shown from below with the houses in the background foreshortened. My scan of that photograph didn't come out too well, so here's a modern equivalent, an image of Chicago, I believe. So I guess Gombrich is saying that older photographers would have said, no, no, you've done that all along, it looks terrible, the angles are distorted, but most people nowadays accept it without demure. I took it from the Wikipedia page on Chicago and there was certainly no comment about it being a distorted image. We've learnt to accept that, it's just how we think photos should look, and maybe we'll do something similar, and that will increase the acceptance of 3D. So the use of stereopsis in art is obviously a huge topic and I'm not really qualified to comment on it. To some extent I think we may learn to use 3D better. I think at the moment it's often been used in a kind of theme park way, we haven't really exploited it, I mean people talk about immersion and so on. But yeah, I think it's a very interesting time at the moment because we have all this new technology coming on. Obviously the glass is free, we've heard a lot about these new technologies in this conference. But I think it's fair to say that whether it's for immersion or whether it's for theme park stereo, the major use of stereo displays at the moment have been to reproduce reality, to enhance the degree of realism in our visual creations. But in the last part of my talk I want to move on and talk about uses of stereo displays beyond art or entertainment, and consider what stereo is good for in medicine. Now again this is a somewhat huge title, you could have a whole conference on the uses of stereo displays in medicine, and so whether it's visualising scan data to make it easier for radiographers to detect tumours or laparoscopic surgery, all sorts of uses which I'm not qualified to talk about so I'm not going to. And instead I'm just going to concentrate on one very small application which is assessing binocular visual function. So I've already mentioned that stereo acuity is the smallest step someone can see using their stereo vision. And this measurement of stereo acuity is used clinically. It's important because it really is a kind of gold standard for visual function. In order to have good stereo acuity, obviously you have to have good vision in each eye individually. If you can't see the images clearly, of course you can't do stereo vision. You also may be less obviously in the case of humans need very precise ocular motor control to align the two images really closely on the retina. So our stereo vision, as we know, only works for a small range of disparities. And actually in many neurological disorders this binocular control is compromised and that's the reason for deficits in stereo vision. It's not really a visual problem as such, it's actually a motor control problem because stereo vision places such great demands on the control and coordination of eye movements. And finally, even more perhaps than the rest of vision, stereo vision is very much a property of the brain. We depend on binocular neurons in visual cortex which can take the two eyes images and match them up. And if all that machinery isn't present and working, then you still won't have stereo vision. So stereo acuity measurements are used in the management and therapy of a whole range of binocular vision disorders. So strabismus, sometimes known as squint in the UK if that's a more familiar term, refers to misalignment of the eyes. So they're pointing in different directions. There's a whole variety of subclasses. You can have infantile esotropia where babies are just born or develop shortly after birth this crossing of the eyes. You can have intermittent exotropia which typically presents in slightly older children and is where one eye turns out, but not all the time. Mainly when the child's tired or maybe ill. Thyroid disease, very common complication can be strabismus and so on. We've already heard yesterday about amliopia or lazy eye where one of the eyes has lower acuity simply because the brain is no longer listening to it properly. So again that's a disorder of binocular vision. So clinical stereotests then are routinely used in eye clinics to get a handle on binocular vision function. And they've got a range of uses which I'll go through in the next few slides. First of all, in this paper on the effect of amliopia treatment, they were monitoring occlusion treatment. So as we heard about yesterday, the patching. In this study, for example, they demonstrated that the median stereorecurity, the most common stereomegument in these children was nil before treatment. So most of them just had no measurable stereovision at all. And after treatment, it was 600 arc seconds. So that's still higher than you would expect in a quote normal child, but clearly a pretty big improvement which they attributed to the treatment. It's been used in trying to work out how and when we should intervene in these children. So this is a paper arguing that children with infantile isotropia, babies, should be operated on sooner rather than later. And one key piece of evidence there is if their isotropia is surgically corrected within two months of it showing up, then most of the babies are going to develop stereovision when they're much older. But conversely, if they experience isotropia for more than a year, most of them will be stereoblined. And of course, it's being used as a proxy here for binocular visual function. So the idea is if you operate on children earlier, you're able to restore the binocular co-ordination and bring their brains back to normal as it were in this aspect. And so measuring stereovision is critical in coming to this conclusion. Again, it's useful for predicting what's going to happen in an individual patient. So if you do operate on a child and then immediately after the operation they have measurable stereopsis, then that's a really good sign. It's likely that the operation's been a success and their eyes are going to stay aligned. Conversely, if they still don't have stereo even after the surgery, then that's a sign that they're much more likely to need further treatment, including subsequent surgeries. So here's a quote from Eileen Birch who's done a lot of these studies and she had argued that improved stereocurity is associated with better long-term stability of the eyes, reduced risk of ambliopia, improved achievement of developmental milestones, better reading ability, all this good stuff. So it's an important thing to be monitoring. Here are some of the clinical tests that are used to monitor it. And you can see they use a range of technologies. So the Frisby test is basically a sheet of perspex or several sheets of perspex of different thickness with a pattern printed mainly on one side but a patch on the other side. So there's physical depth between the two and the others, you know, they use the polarised glasses or anaglyph and so on. See if we can hide him again. Ready? Where's he gone this time? Okay, good boy, well done. That was very clever. I'm just going to hide it one more time. Ready, steady? Where do you think it is? Oh, you found him well done. So that's a clinical stereo test as they currently exist in practice. But I think you can immediately see in that video that this is a kind of boring test for children. The lady was doing her best there to make it interesting. But you can see that this is rapidly going to get old for the child. And the trouble is in order to get a good stereo acuity measurement, you need many, many responses. You try them with a big disparity, you make it smaller, you make it smaller, you know. So it's a struggle getting that kind of data from very young children. And it's very young children in whom the clinical need is greatest. The Frisby test, because it is physical depth, has non-stereo depth cues. So it's theoretically possible to cheat by, for example, moving your head and using motion parallax. The 3D glasses get around that, but that brings its own problems. So, you know, if you give a four-year-old a pair of glasses and try and get them to wear them, you may find the kids more interested in playing with the glasses than in doing your test. And they offer only a few difficulty levels because there are a set of, you know, cards or books. You have to control the viewing distance. If you don't, that introduces errors, but of course, you can imagine it's just another problem when you're trying to get this four-year-old to do your test and you're trying to control the viewing distance. So all these combine to make the test-retest reliability on these things very poor. It's really a factor of four. So if you measure a child with a stereo acuity of 200 arc seconds on one occasion and then they come back after treatment and it's now 50, you might think, great, you know, I've really improved this child's vision, but actually you don't know that you have. It could just be the measurement error because a factor of four is within that range. So that's obviously undesirable. And I think we can nowadays do a lot better. So that's where our asteroid project comes in. So this is a project that we just started, funded by the Wellcome Trust and the Department of Health in the UK. And it stands for Accurate Stereo-Test. And here is a big team, a multidisciplinary team of computer scientists, clinicians, ophthalmologists, orthoptists, and so on. And the basic idea is that we're using the Neo3Dio, glasses-free 3D tablet, which some of you may be familiar with. We want to embed a stereo test in a game on this tablet. And you know, if you've got small kids or grandkids, you know, small kids love playing with these devices. Two-year-olds are always trying to grab their parents' phones and play games. So they're very used to this and they're very comfortable with it. It's a very intuitive kind of interface where you can touch the screen to indicate what you see. And you don't have to interact with any potentially scary, strange adults. We can use the front camera to track the viewing distance as the child holds it. So we don't need to control where the child is holding it. We can let them hold it where they feel comfortable and just automatically correct and calibrate for that in the computer code. And because it's a computer, we can display whatever parallax values we want and we can make them personalise to the individual patient. So there's a well-established set of algorithms in vision science called things like adaptive Bayesian staircases, which are statistically optimal, take all that patient's previous responses and use that to calculate what is the best value to display to this particular child. And obviously that's something that's only possible when you're delivering a test on a computer. So we're hoping that we can exploit all this new technology in order to produce accurate stereo acuity measurements and that these will help clinicians improve children's vision. And I think that's a really exciting new application of a stereo display. OK, so my time is very much up, but this is really what I want to leave you with. Stereo vision is such an amazing and fascinating ability and I think it's great to be able to study it in so many different species and of course it has so many applications. And I think this is a particularly exciting time to be working in stereoscopy and binocular vision. Thank you. APPLAUSE
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Stereo vision is a resource-intensive process. Nevertheless, it has evolved in many animals including mammals, birds, amphibians and insects. It must therefore convey significant fitness benefits. It is often assumed that the main benefit is improved accuracy of depth judgments, but camouflage breaking may be as important, particularly in predatory animals. In humans, for the last 150 years, stereo vision has been turned to a new use: helping us reproduce visual reality for artistic purposes. By recreating the different views of a scene seen by the two eyes, stereo achieves unprecedented levels of realism. However, it also has some unexpected effects on viewer experience. The disruption of established mechanisms for interpreting pictures may be one reason why some viewers find stereoscopic content disturbing. Stereo vision also has uses in ophthalmology. Clinical stereoacuity tests are used in the management of conditions such as strabismus and amblyopia as well as vision screening. Stereoacuity can reveal the effectiveness of therapy and even predict long-term outcomes post surgery. Yet current clinical stereo tests fall far short of the accuracy and precision achievable in the lab. At Newcastle University, we are exploiting the recent availability of autostereo 3D tablet computers to design a clinical stereotest app in the form of a game suitable for young children. Our goal is to enable quick, accurate and precise stereoacuity measures which will enable clinicians to obtain better outcomes for children with visual disorders.
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10.5446/21712 (DOI)
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I'm going to make a little demo of the workflow and the basic feature I've used in Caritas for Current thoughts here. Starting with a group here. Yes, yes, yes. Projects like this. Okay. Let me come. Okay. Yes. Better. So, the good thing is the photomic books is the set player to draw the frame. So, you have the grid. Unfortunately, the vector shape doesn't snap to grid already, but it's in the future request. So, I have the frame. You can adjust it on the grid. Okay. And I change the style of the shape to get a bigger outline. Okay. White fill and black outline. Then the same player above. And you see the sequence is to lock the alpha to the draw will be restricted to the frame under. Okay. So, this is then I show you the state brush. With the first function to get. Okay. Okay. And on the second layer, I'll make some inking again with the state brush with different presets. Okay. Why, why, why? Because the same player has moved from the group, so that's why all these appear. Okay. And we start again 21. Okay. This layer moves this time. Okay. Layers that needs some work. So, let's just start with my state brush. So, the good thing with state brush is to get a rough natural looking line with contrast to with vector smooth line in most other drawings so far. I like it to get some natural in the drawing. You guys can put angry. That's better. Now, as Lucas showed you, there's the acting brush for people working back in white to get some patterned, black line patterned. And this is like this. Again, I need to create this. Okay. And here, I'm making a more bigger line. Now, to erase, I need the pixel brush with plain simple field and erase mode. So, clean this up. Okay. So, now for the color part, another paint layer. Again, with the pixel brush and the plain preset, simple field. I'm going to get my color. And I will use the field tool to get the blue faster. Not the field tool, the select tool until. Oops, my area is not closed. That's too bad. That's closed. So, that's it. I don't know why, there's a still hole. Still not so, I'm not going to use it and save it by hand quickly, it will be better. Not the field color. Write that effect to the horizon line. OK. Let's look at this one. And there you can see the color is above the outline of the frame. So I can clone my frame. And it's like this. It is. And move the clone on top and set it to multiply. So I get my frame back, outline. I'm trying for a quick setting. Regardless of the color used, I'm using another paint layer. And I set it to soft light 100%. And then clone this layer. OK. And it's long. OK. And the clone, set the clone to hard light and run 40%. Depending on the effect you need. And then paint black and white. And to get my effect. I can. And for the clone, as there is not this shortcut icon, you can turn it outside looking. OK. There. Too dark. I forget this. OK. And some light is white then. Wow. OK. So that's the basic for the color I used. And for the text, I still use handwritten text because it's more natural looking than vector text text, which are available also. But as I said, I prefer writing myself. So create another group layer for the text. Not the wrong group. And the group then layer. And I'll press it for writing. And I'll show it again for writing line. OK. So the text is with the text brush. I should have done this on a separate layer to fill it more easily. Not my line. And I'll just use the fill tool. White will be better. And the fill tool is easy to turn pale. That's it. Now I can move my blue. OK. That's it. OK. You've kept everyone very quiet looking at the drawings. It's very nice. Thank you. Thank you for your attention. Any questions? Questions, anyone? Do I believe that everyone should be able to do this? How do you handle doing multiple pages like you're going to do at 30 pages? How do you manage? For most people, pages in the comic book. For most people, I import my separate pages in previous to composite the full album. But it's planned to manage several pages inside Territah. Other questions? OK.
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I want to make a workshop centered around drawing comics with Krita, including live demo and feature talking. For the last 6 month I’ve been testing Krita to evaluate it seriously as a comic-book artist tool, giving feedback to the development team. To achieve this I’ve worked on a little experimental comics called "Wasted Mutants". So I want to make some live demonstration, highlighting the feature I’ve found useful for this task, some new upcoming/still in test exciting features, and maybe what is still missing or could be improved in the future to get it perfect.
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10.5446/21710 (DOI)
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And from the project, it's probably part of the 2016 model. But it's about the idea that the, think about it for some time, that if you're told that it's media, they get all the information, but they don't really have the idea how to do something. So one of the ideas that smells of, it's not the same as knowledge, it's not the same as information. So for example, information, that just, it's a vice. So that's it's a vice, it's a warning. So if you have information in confidence, you have knowledge, but for most of the users, you need to put information in relation to about information, some rating of information you have, like the particular, the form that is, what is needed, for example, if you're just, and also get a weight of the information you have. So if you're a part of a tutorial, like an inquiry, so you also have to know, is this for the transporting, or for the TV, or is it really for the inquiry? That's the knowledge you need to handle this information. Of course, this is not just a case, it's a normal thing. I will not talk about normal things, doing my part, but of getting a lot of knowledge. And so, if I hear about the economic process, so we have good kind of inputs, and we follow the certain amount of steps, so when we get the most output we can use, and of course, our conditions of the grade, so it's a good question. So my idea I would propose in this talk is, I have a data base for taking out good products. And I'll elaborate on this later. Okay. So this is not about software, it's about support and power, and we do like software to support software, but it's through our real and only material processes. There are some movements that we can do with, if you were to actually do three-man engineering, and I think a lot of the came from Asia, and from the world of the earth, and hopefully use the better movement. Do you know about that? And some IIT, I think, is a laboratory where we can build both in the... and they use like three-digit print cards to generate a configuration of like that. So my idea is yes, so for some examples I would add for users of the data that I have in mind, for example, young international, who wants to build a business with a professional student. The kind of charcoal is not made from wood, both are from reused software. So for another user, if you want to school them to a level project, I want to create an inexpensive visualization practice, just for education and projects, or for university research, want to publish their in-use microreactors creating a kind of... So I don't know if you know about microreactors. So the technical process is there are different ways how to do it. In the classical way, there are big tanks and pipes, I can do cook top and the surface from one tank into another tank and stuff like that. So some of the reactors where we have the catalyst. The thing with microreactors is that we do the same chemical reactions for the very small tank. And that's like if we just find the channels and can it look like a log like 1 m x 1 m x 1 m which process it, but it has the same throughput as a big factory because it's primal all the time. So that would be something interesting that you would want to do in use in the world. So, not that I put anything in there, but it should be incremental. Because most of the stuff is in the computer or even on the university, so you could not just take a lecture on how to do it and just do it. And there are a lot of interesting things. We love all the expressions we know how to do, but should be general knowledge. Especially in the world countries, so they can get to resolve a normally known test. And another thing is, I call it global reset. There's a nice case of a bomb. I was asked, no, no, no, I'll try to do the last thing. There are a lot of things that are stranded on the low planet and there are some major major repair, but I'm not sophisticated. I know a lot of technology and it wants to help the nature, and we find out we cannot do anything. So all the technology we use every day, there's nothing that could implement on this planet to help the nature. So what he adds up is that peaceful spaces, we make ourselves a pathway, but the nature is fascinated by the sandwich because we haven't seen a sandwich before. So all the technology in this world nature is how to make sandwiches. But he's very technologically well done, so that's that. And well, the global reset would be there's a devastating disaster on Earth, so it is probably to be used to let it could lose access to both of the factories at the moment and that kind of gets better and the flow of production on the world doesn't work anymore. My problem would be that it would probably lose most of our technology technological knowledge and we would not be able to reproduce it because we lost the way how to do that. Technology builds on whichever and if you forget the small steps behind and you lose it, you will not be able to start just now. So it's very important to have a database of all these technological processes. Okay. Now let's take a moment to take a look at the processes. So this is a schema I've come up with and the process takes several sources and all of the intermediate products and all of that. And the process happens. It also is a number project for a hypovox or some waste or combination of these. And doing the process, we'll use some tools. So that's the kind of schema I want to use from the database. So far, the network source is one of the products too. So this might throw a fear of impact because for example, what we have is cold. You have to get it from somewhere actually we have to take it out of the ground and transport it somewhere. So it's just another product. So what's the energy problem? For example, the normal is the tool which converts gas which is a material to energy. And of course, waste or the high products is also products. So what's waste for one, could be a resource for something else or someone else. And it's just a question of how you value the product or... And again, we have tools. You can produce a tool and when you use a tool in the process, you have a tool to begin with, you use a tool. And in the end, you still have a tool but it might be some algebraic. So, and in this way, you can model tools or you can have to use energy products. And we have the... So what we come up with is a product and we have a very simple CMOS for another new process. So, and the main characteristics is they have input products, output products, and some of the steps that we're going to do. So it's the generated description of the input with the output. And of course, we have the description of the business in each so all the processes can be done in every environment. So for example, we can have another special amount of heat and so on. And what is also important for you, this was called the risk, is the truth patterns. So a lot of... I think a lot of the process is pathosite and we have a combination to use with our pie. But we make it database, which is not an advantage of this process. It's the important to include the patterns and just sort of give you a very important method and go about doing them and put the word doing it in countries where this process is protected. And another important thing really is the limitations. So you have to prove that this technical process can be done. So if someone is interested, you document the product. Just a short break, just do it what products you have and how you solve them. And in the database, as such, the product has limitations. This process is more documented and more likely you have the use again and put state. So now, talk a little more about products. So while we have very simple schema for the processes, we would probably add a more complex schema for products. So this is just the random hierarchy of game of the products. We have organized them in several relationships. So for example, anything you get is liquid solace or some categories of products. And so we would typically walk up to a special type of water and walk up to a special type of liquid and liquid is a speciality of the general category of the products. And so for years, you would have to organize the product and touch kind of a tree. And then we have a... So in fact, it is a product which would also be complemented, is of course, a unit. So some products are made by the volume, others are made by the mass, or energy, which of course, would be met up in the final two hours. And we do have some quality of the product, which also can be calculated as usable or less usable. You will follow the circumvent risk, including the facility, the system, and any other kind of destruction of the product. So we would say that we would put it in a vacation, which would consist of two parts. So one would be the database of product processes, and another part would be the customer support, because it is kind of information that needs some station. So if you... It's a submission which starts the wild idea, you have this pattern, and then to refine the idea, and have it collected that, and maybe then some more will be implemented, and so this processes the product, and when it's approved, it would be written into the database. And the community would also work out how rules and procedures would follow for this to happen. And in the end, you have the database, which can be ran with rules by anyone. And that should not only use the extra search, which is how many do you have database, but it also uses mysector search, so we have a process. We have some product X, and we are interested in what process the product will produce this product. And then you can go back and find out the process you need, or to get it done now, of course. Or the forward search, so you have a product Y, and you think, okay, I have this, what can I do with it? And you also have a product X, so you get the product Y, so you have more general product, so you can get from water to liquid, or any liquid, and also to open a kind of water out, and then you have a thin water, ice, and whatever. Okay, then... So my idea is to get a website like that. And we will not only have operators, but organize the database and the website, but also submitters, who will be able to complete the processes, or in the limitations of existing processes, or pattern resource, or just to bring the document product for the eBJ, and the search keyword right now, and then go source those into a form of the database, so they can put in the schema online and use. And of course, we need everyone for participants, who will use cloud for stuff, and ensure some level of quality, and also rating and comparison of processes, and what they want. And another thing to get, so we're going to be a fabulous... So my idea with the university is to really use and contribute to the database, so from the research, and also use tools of whatever to implement some of those processes, or to do them more simple processes. So, so, so one gets number of limitations. So of course, one could also get some of the best, new, abundant products, to put in stuff online. This is very open, and I know there's a title on it. And of course, when you have a project, you usually have one of those projects. But you could combine those products, because you can use one of those processes of the database. You can combine your projects by using this printer, and having the database on top of it. Okay. I'm going to get into that, but we'll have to do it. Because the whole thing is a bit of a mess. You don't know what way to go about this. Nothing is this way. So, if you think it's a good idea, then I'm going to be happy. Or if it's a good idea, then you know what I mean. Okay, thanks. Thank you. Thank you. Thank you. So, I was looking at it. You had a good solution for someone who's got an idea. It seems like, a few slides back in, you had things that were like imaginary, or created, or things that you don't even know if the signs exist or not. And a lot of times, research and that is hidden. So, I've heard rumors about things like tree replacements, like as a way to sequester carbon. You know, something like that. Like a tree, like outside the spring, they take carbon release oxygen. I've heard things around that those exist, and you can make them, and there's science behind it, et cetera, et cetera, et cetera. I was going to say, how does someone who's in that sort of creative thing of how do you like solve global warming, something like that, with your vaporware, how would you protect against sort of proprietary science, like something that's very deep inside an R&D lab, and you're like, hey, I had this really great idea. You know, is that a licensing issue, is that changing how patents work? How do you look to the future rather than sort of preserving the past, just like you, how do we get this stuff for me? No, it should also be a new start. Definitely, not only old start, but also new start. And could be something totally crazy and wild. For example, one thing, it could be number one on this, but it could be on the show. There's often a shift, also something like from some fiction. It's practically a machine which can produce anything, no, in material energy, including itself. So this is of course a very wide of concept. We have no idea if it's real, actually, or not. But on the other hand, it was very useful, to be able to see the ultimate machine at all. So that's something you can put in, and we can discuss it. And it will probably take a very long time because it gets from a wide audience, for all the stuff that's on the stage and putting it away. About our proprietary stuff, yeah, it's a proprietary search, and they will not put it in the company. On the other hand, if someone else just has this boiler meter, it's the same thing, discuss this on this application. But before the proprietary company applied patterns for it, and we luck out. So because then it's put out on the fire art, and it will not possibly get ahead, and it will not be the same idea. I think. I will suggest to your partner, a friend of yours, who started in our website, and currently, there's only information, but I selected just a few days, who might have to do this. I started by asking a question on his website, just like a step out of all. Yeah, and he expanded the work he wants to do. He wants to have knowledge measured by units on the site. So just like, absolutely, here, we have our more interest-contributed and more fire art. Our question is, do you think that there is a way to get this information? Yes, he'd like to see this information. Absolutely. When you first start with this, it's going to be a part of this only, but he's not as small as that. He could get it right. Do you have any questions about it? Have you ever been able to do it all with it? We've got them now. Oh. So, um, I just spelled the site. I don't know. It's important because it's UMAO.com here. Yeah, you have to go down here. Yeah, go down here. This is just a short comment. It would appear to me that you may have some success finding a benefactor, a charitable foundation, or maybe even a component in United Nations, or some organization like this that would be interested in providing seat funding for something like this. So maybe the first step to get this out of APRWARE would be to write informal grant results and put them in the right hands. I don't know if I have the right hands to write grant results. Any more questions? No thanks. Next up for today.
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Modern societies are based on technology. But this technology isn’t free: it’s protected by trade secrets and patents. It’s also mainly used for generating profits and not for helping people. FLOSS is nice, but it only covers software. Wikipedia is nice, but information is not enough to use a technology. CC-licensed art is nice, but it won’t fill your belly. Today, despite all our technology, a large part of mankind does not have sufficient access to clean water, food, energy or shelter. This talk sketches the idea of a public database for sustainable technological processes and sufficient information on how to implement them. The database would be accompanied by a web application that allows discussing, evaluating, documenting and staging of process descriptions. The discussion will cover the vision, feasibility and promotion of this idea.”,”Andreas Vox is one of the core team Scribus developer. He’s the text engine expert among other things.
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10.5446/21713 (DOI)
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There was a start on the 1st of June this year, so this is a pretty nice start. We've been working on this since actually until 2007, so I'll quickly show you what it is. If you're very interested in it, of course you can come up to me and talk about it. I would love that. The People Graphics Research Unit is a two-year project we got funded through the European Cultural Commission. It's a collaboration between four European media labs, Media Lab Prano in Madrid, WALM in Rotterdam, Pixel in Norway, and Stunt in Belgium. Constant is the organization I work for. We are the leading partner, so to say. And our courage to apply at the EU for such a project and to take on this as a leading organization came from our understanding of two related things. One, practice shapes tools, and two, tools shape practice. These two things are very simple, but they're complicated and interesting. Bruno Menari, a designer that worked until the 70s in Italy, made this beautiful drawing of a wooden spoon he found in a drawer. He set this as an example of how you should think about design. The spoon has actually been eaten gradually in soup because the stirring slowly, slowly, slowly has transformed the shape of the spoon. We think something similar is actually happening with digital tools. It's only not so easy to understand what it needs to eat the spoon and the soup. So when you string these two ideas together, the fact that practice shapes tools, and tools shape practice, you understand that if you want to change your tools, you also are changing your practice in the other way around. It means that there's like a feedback loop between the tools we use and the way our practice works. And so this is where you can understand that as artists and designers, we need to take initiative in trying to somehow innovate these tools ourselves. So we asked ourselves this question, what future practices can we imagine and which tools can make them happen? So the Viva Graphics Research Unit is an artist initiative that invites developers and academics around the table to think with us about the possible tools we might imagine and the possible practices we would like to have. For us, the fact that this is called the Viva Graphics Research Unit is not trivial. For us, it's essential that this is done with free Viva and open source, in free Viva and open source. It's essential because in principle, producers and users of software are equally able to learn and take part in the construction of software. This is important for us. It doesn't always work that way, and sometimes you have to make an effort to actually make that potential happen, but this is possible. So we use the Floss Tools, Welcome Divergence, Alteration and Exchange. This means these tools inherently invite differences. And for us as artists and designers, this is extremely important. Again, some tools might be actually more stiff and less flexible than we would want, but still in principle this is possible. Certainly when we talk about a research project, for us it seems evident that we want to work in a situation where knowledge exchange is open and free. So our engagement with the Viva Graphics community since 2006 has always been about that, but trying to find a platform where we as artists and designers could co-create our tools. How can we do that in a way that we could start from our practice and somehow be in dialogue with the developers of the tools we like to use so much? This is also the sole reason we decided to organize LGL Brussels, but after it was over and the energy was started to end away, we realized we had not done enough. So this is how we started the unit. Because we realized we needed a platform, a platform where artists and designers and developers can truly work together and truly construct together. So not the one in one or the other, but really at the same level around the table. We realized that we were really missing reflection upon the history, use and construction of software-procureted work. We had no idea. We had really not a lot of thinking about what the relation is between creative practice and software tools. So this we need to somehow, this whole thing to fill. But also we thought looking at its holographics and the kind of tools and how they're happening, there's a lot of effort put in developing in bug fixing, maybe even in user interface development or in user interaction. But the true innovation is a different thing, where that seems to be somehow almost automatically happening when developers develop their own tools. Because they know what practice they're talking about. Where we're talking about holographics, which the story changes. Because you're actually working across disciplines. You're working across practices. The practices of the developer are not necessarily the same, sometimes they are, as the artists and the designers are. So we thought it was important to make space for innovation, for speculation. So the first person we called up was Mena Nataro in Madrid. A very interesting lab working really in the city of Madrid with people of the neighborhood. And their work has been very much by trying to use free software. All of these partners are clear about their position in that. To take on different issues like ecology or how the other fabric is changing. The second is Worm in Rotterdam. Quite a different organization. More ground-up to alternative music and alternative publishing tradition. And right now they've taken on digital media as well. You can imagine that they have quite a strong, interesting game culture in popular culture. The third is Pixel in Berkley. You can see that these pictures are a bit of a cliché. Because I'm trying to quickly show you the differences between these organizations. Pixel has been always involved in hyper-culture. The hardware has been their strong part. They grew up in the festival, the Pixel Festival. And from that they have been innovating tools ever since. And the partner I speak from is Kusum in Brussels. I think our part to end is the fact that from our feminist interests, we've always been thinking about what is an or what is a standard. And how does this affect the way you can imagine. On top of that we found ourselves some brilliant social partners. Some of you might know, some of you may not know. We tried to make a healthy mix of practitioners, initiatives, schools, universities and play is a rule that the demographic community is represented through. So how was this work? The backbone of the project is a series of research meetings that will start to happen as of fall 2011. These are meetings where we invite all partners from different countries to have extra guests that seem to somehow be relevant to the issue we're discussing. Each research meeting will have specific topics, of course. We are still formulating the work. But the first one will deal with network graphics, trying to understand how the fact that our works and our lives become network somehow reflects back on the tools we use. The second, we titled co-position. This has no less than the mission to rethink page layout from scratch. The third, he speaks with online. Here we try to work on the idea that digital drawing actually has become a co-author with machine. We move from body to digital and we're trying to discuss with people developing these tools how that actually works. The fourth is the least defined, but we have time for 2012. Abstracting craft. This is trying to bring the different threads together, but also to speak about teaching and learning and how you somehow communicate your craft, your skill. Number five, we return to Brussels. Copy, study, distribute, because we thought it was important to take the dissemination of all this information into the project. So to not do this as an afterthought, but to really make this topic a meeting. On top of that, there will be a large conference in Madrid in spring 2013. This will coincide with the Interactive Workshop. They've been running since 2007 to a large scale open call based workshops. So around 10 projects will get selected and then worked upon by volunteers. Alongside that, we will commission two essays, commission five prototypes. These prototypes are developed by designers and developers together. And we're working on a reader and an online publication. And all these commissions will be discussed and assessed in the research. So as I said, this is starting literally as of June 1st. So we'll do the moment we can start setting this up. So we'll have a public mailing list. There will be a website with reports of prototypes and a reader growing. You will keep IRC logs of the meetings and keep notes. There are online publications, like some parts of the peer. But also visit that you can participate in research meetings. And we will not have the ability to invite you all, but you are invited. Meaning that research meetings will be open. Both they will be streamed and logged in IRC, which you can also physically take part. If you believe in the neighborhood or specifically on a certain issue. We try to invite as many of you as we can for the next four years. That was a very small project. And then the last step there will be as of June 2013, a physical LGROOM info point that's made up of my sort of IRR. That's where you are. Welcome. There's temporary sites just until we get working. So we will announce where everything needs to go as soon as we're ready. So if you're interested, talk to me or have a look at it. Thank you.
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The Libre Graphics Research Unit will be a traveling lab where new ideas for creative tools can be developed. Its diverse activities range from the practical to the theoretical via writing, research meetings, experimental prototyping, a conference and a workshop. The Research Unit is an initiative of four European media-labs actively engaged in Free/Libre and Open Source Software and Free Culture. This cross-disciplinary project involves artists, designers and programmers and we would like to develop the work in dialogue with the Libre Graphics community. What future practices can we imagine, and which tools can make them happen? The Libre Graphics Research Unit is a collaboration involving Medialab Prado (Madrid, ES), WORM (Rotterdam, NL), Piksel (Bergen, NO) and Constant (Brussels, BE). It will run for two years as of June 2011 with the support of the EU Culture Programme 2007-2013.
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10.5446/21714 (DOI)
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Well, in fact, it's more like a road toward the document object model and the file format. And it's more or less like lightning talk, so it's very good chance I'll make good on the 15 minutes delay we already have. OK, let's start with the document object model. So it's three words. And document means it describes a document, not any menus or windows or processes or UV elements and stuff like that. But just a document and one thing you would expect. If you have an instance of a document object model and you've write it to a file, and when you load this file again to get a document object model, you should have a faithful copy of the original document. And of course, object means comes from object oriented. So you would expect some kind of trees or object, and every object has attributes and methods. And the important part, and that's where Scriber's legs right now, it's a model. It's not an implementation. So of course, we have classes, object oriented classes of Scriber's, which describe the document. But there's all kind of other stuff, how to do some things that event handling and what else. And that's not what we understand with a model. So the advantage of a model is when you have more than one implementation in theory. If you already have an implementation, it does not make sense anymore. You have to have a model which relates different implementations. OK. So a document object model has many users. So of course, first it's a guide to implementation. But then you can also use it for serialization, where it's writing to a file and loading from a file. So the most common nowadays is to just use XML and map objects to XML elements and attributes, object attributes to XML attributes or other elements. But you can also use it for scripting. So if you look at standards like SVG, they describe the document object, especially from how to tell how Javascript can access a document and change a document and work on it. So that's another important thing you need to do. It also helps with undo, because if you have an document object model, you can describe, OK, I have this action, and I've used the document object to describe the state before the action and after the action. And then the undo step is just to revert it. You can also do it with use it for testing. So if you have a document object model where you define some of the methods, you know what is expected. And then you can just test that. It just more or less gives a framework to talk about what is to test. Because if you have an implementation and you don't know what it's supposed to do, well, you can just observe and then say, OK, do I like it or not like it. But that's not really testing. And of course, another possibility would be to help with interoperability. So if you have different implementations of one document object model, you could have different applications which use the same document object model and hopefully can exchange data. OK, so the idea, what I would propose for Scribers is to use relaxNG to describe a document object model structure. RelaxNG is XML schema language. So the most common are relaxNG. The original was DTT, document type declarations. You might know about Bayer limitations and, of course, official XML schema language from W3C, which is a kind of complex and not that nice. DTTs themselves are not XML. But they are a part of XML standard, but how to describe XML. XML schema language is always XML, which is an advantage. But has the disadvantage that XML is not very readable. This example of relaxNG is the compact representation of relaxNG. The interesting thing about relaxNG is that they have two flavors, and they are equivalent. And you can convert this compact notation you see here in the example to a XML version you can use for tools and vice versa. So it's a one-to-one correspondence. And that's pretty nice. So oh, yeah. And here I just made up a possible grammar for Scriber. So you have to have a start element. So you just say start with document. Then the document is an element like Scriberstock. And Scriberstock is the process of a preference section, then the resource section, the style section, the content section, the structure section, layout section. And having said that, you go on with saying, OK, preference type thing looks like this. It's just a list of attributes. And here I used some real attributes we use right now in Scribers, which are probably going to change. For example, this name, unsullpages, it's a mixture of German and English. And we really want to get rid of that and have proper English names everywhere. OK, you can also see that if you have an attribute, then this is a name for the attribute. And you can give it a type, a data type. So this is an integer. You do know what it is. And it's possible to define several of these data types. And there are some predefined ones like integer and text. But you also could define your own points and whatever. OK, so advantages of Rolex and G. It's very readable. I hope you agree. And that allows it to discuss a dumb structure, because it's not fixed. That's just a mockup. And among what developers, we and maybe also interested users, we probably will do some fair discussion on how to fix the file format at the document object format of FOScribers to make it most usable. And so another example is it also provides a file format at the same time. So there have been ongoing complaints about existing file formats, because it was too complex. And of course, we also have to change the file format once in a while, because people like Louis are starting to rank with it. And so, yeah, and we will have a good correspondence between the implementation and the objects at runtime and the file format also. Next thing is because of the XNG, KS has another flavor, which is XML. It has good tool support for the XNG, for validation, and for other stuff. And last but not least, it's extensible. You can have annotations, two elements, which could tell how to use these elements or add documentation to it. You can separate your grammar with namespaces. So we could use it as a gene namespace, as well as our own scribes namespace, as well as CSS namespace, or whatever. And yeah, there are some interesting ways to use data type libraries, where you can define your own data types that you want to have. And we have some of those data types which are used in scribes, for example, for points or paths or colors. OK, so I'll just make an example of what an annotation in LexNG would look like. And the green part over there, which is an annotation, it looks very similar to the rest, but just in square brackets. And right now, I use the namesplace impl for implementation, and I made it up, OK, the class would be named scribestock. And the idea is that this annotation tells us, if we have elements scribestock in lower cases in the XML file, we are supposed to use the C++, scribestock in camel case, in the program. And our idea is to have a tool which translates the LexxNG to C++ code in a certain way. That does not exist yet. But there's some good reason to do it like this way. I'll go back sometime. If you look at this attribute, this is only the first three attributes. The scribest document has probably some dozens of attributes just for this. And altogether, the number of different attributes on different elements, I think, goes into the thousands. So now if you see that for every attribute to make it accessible, you have to write it to XML. You have to parse it from XML. You have to have methods to set and get the value. You have to make it available for scripting. You want to undo changes to it and stuff like that. And if you want to do it in consistent meta, but you have to do it like thousands of times, it's very error prone. So it would be nice to have a tool which just takes an annotated LexxNG file and creates a code which doesn't automatically in a consistent way. So that's one of the aims of it. OK. Now, and this is a conclusion. What are the steps ahead? So the first thing would be to define a LexxNG system like a mockup I just started to get it going. The second would be to implement a serialization in scribes. So we would add methods and scribes where the existing document implementation would write out XML, which would be validated against the LexxNG scheme we have. Once we have that, we can discuss the structure with developers in the community to tinker with it and make it better. So it evolves. So for scribes 1.6, we have a nice grid on the file format and an additional virtual-adaptive model. And also, I want to provide a tool which first had to go with Create C++ code from the scheme and by rotation with the LexxNG scheme to just use some ideas which are behind the server. Central base for LexxNG scheme which tells us our work on the college should be implemented. And the rest is all automatic. We don't have to be afraid that any parts keep in. From the end, once we have the tools, we can change the LexxNG and just regenerate the code and it will always stay the same. The file can be an other. OK, that was my phone. I think we have partners to that for that. Now, for your step number four, that looks very familiar because in the past I've done the same with XML schemas, XML, and access-sl-t to do the conversion. And one of the things when I was doing that, I was doing a bigger project I applied it to, I looked at not only when you make that conversion, you can create code to consume the file, put it in the format, you can create code to do stuff with the format, but you can also create a lot of unit tests to validate your assumptions about the format and handling of it. That's all that's interesting. I'd ask you about detail about it. So when they have encountered with this famous file format in the same plan, there are many, many options that are not well-optimized. So I wonder if in the last few years there's some method to map documentation for particular elements to get out of the project. So this is an application we have. I showed that's a general format of location. There is a special thing where you just use a number sign for comments, that's one thing. And if you have a element of sign, that's an abbreviation, something like a paradox or something, that's a document, just the documentation is a whole whole thing element. All right. Thank you, Carl. In that question, I mean, it would be nice if the people with strong interest in the script's format, I thought that you and the Italian guy who is doing the specification really deserves, maybe that they get involved. Yeah. I plan to have a discussion on the graph. So I would like to pose where we have a sample of the case. So I just wanted to say this is really great. And thanks for your great explanation on that, and it's the first time I actually got this. And also as an interest in first, I would like to answer some of your questions. Because it was mentioned, this was coming up very, very soon. I was wondering if there is something I could answer for the center of expectations. Well, I hope we can set up a discussion on ideas of our guide pretty soon, and also the first generation. And to have it complete, I think it would be for the next stable version. So it would be late 1.5 or 1.6. So the next stable version, 1.6, would be the start of the stable and the end of the forward. I would also like to say we tried to improve the pipeline for a long time. But it's kind of difficult for now, because it's always a moving target for one thing. And it's also very complicated to trade a file on, I think, but there are a lot of places on the code which you also have to change. And I really want to have this connection between the two things, the code, where you only have to trade it to one place. OK? Thank you very much for that. Thank you. Thank you. Thank you.
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A Document Object Model serves more than one goal. Apart from storing the document’s data, it also supports scripting and serialization. It’s also the backbone for talking about compatibility, extensibility and testing. In this talk I’ll propose to use Relax NG for describing a new Scribus file format that also serves as DOM. With some tools, design patterns and Qt’s metaobject framework it will be possible to generate a DOM that maps 1:1 to the new file format and is accessible to scripts.
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10.5446/21716 (DOI)
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So the first one is Adam Forney's work that he's been doing as a PhD student with me. And we're going to show you how you can use Google Suggest to quickly figure out what your users are doing with your software. This is a really cool technology. Later in the day, we're going to show a new version of GIMP we've created called Adaptable GIMP. So stick around for that. I think you'll enjoy that as well. In both of these talks, I encourage you to interrupt us during the talk and ask questions because you'll get the most out of the talk if you actually stop us and say, hey, wait, what about this? What about that? What about that? Right. So don't wait until the end. So I'm going to turn it over to Adam now. But again, please interrupt. All right. So as Mike already said, this is about understanding how people are using your software based on looking at what search queries they perform. It's based on the observation that when people run into trouble with software, with interactive systems or devices, first line of defense is often Google. All right. So let's start with a quick motivating example. All right. So is it getting me now? Yeah, maybe put it on the right side here. All right. Let's try that. Okay. It sounds better. All right. So here's a quick example. Back in September, I went to Google and I typed in Firefox how to. And immediately, of course, Google returns a list of 10 suggestions for how I should complete this query. And the important thing is that these queries are actual queries that other people have performed in the past and they're sorted approximately according to their popularity. Just looking at this list, we get a pretty good idea right away of some of the common activities that Firefox users engage in. And so there's an interest in privacy, clearing the cache, deleting cookies, that kind of a thing. But if we go further down the list here, I've highlighted this one. It's a little bit curious, right? Firefox how to get the menu bar back. All right. So we can actually inspect the interface of Firefox to try to figure out why this is so popular. All right. So this is Firefox 3.6. Again, I did this in September. So Firefox 4 wasn't, it was still in beta. Firefox 3.6 on Windows XP. I'm happy to report that this is a problem that's only on Windows. But if you go to View Toolbars and you uncheck the menu bar, well, the menu bar disappears. Problem with this is that the menu bar is now gone and that was how I actually accessed those options to begin with. So the first time I did this, I actually had no idea how to undo that action. I had no idea how to recover from this situation. And it turns out that I'm not alone, as you might have already suspected. If you exhaustively look through Google Suggest, here are a whole ton of different search suggestions all related to this missing menu bar. Using the techniques that we're going to talk about later, we've identified over 150 different suggestions in Google Suggest about this issue. And we estimate that a search from the set is actually performed about once every 32 minutes on average. So what I think this example demonstrates, and it should really appeal to your intuition, is that search query logs are the central repositories that catalog the day-to-day needs of a user community. And I'm actually going to step back a little bit and look at this in sort of a broader context. So there's actually been some research done at Microsoft Research looking at how to use query logs to do things like medical research and social science research. And a researcher named Matthew Richardson, he has this quote, which I really like. So the query logs act as if a survey were sent to millions of people, asking them every day to write down what they were interested in thinking about planning and doing. So this is very rich data, and it's highly ecologically valid. So to demonstrate that, actually, some of you may have come across this in the past, but Google actually produced an application called the Google Flu Trends, where they look at health-seeking behavior. So searches related to flu symptoms or that kind of a thing to try to predict when somebody would go to the doctor and be diagnosed with the flu. Now the important thing is that their model actually is very close to the data that was released by the CDC, but they were able to produce these numbers in 24 hours, whereas the CDC had a seven-day lag because they had to wait for the doctors to report all these cases. So it's a very, very powerful technique. Now taking this a bit closer to what we do, I looked at the Google Insight for Ubuntu, and I think we can see a six-month release cycle here. So it's actually a pretty neat data source. All right, so the claim here is that query logs can reveal the tasks and the issues for any publicly available interactive system. So I stress here that it has to be publicly available because people have to be performing searches, and you get better results when you have a larger community, a larger user base. But the problem that we have is that we don't have access to Google's query log data set. So the question is how can we approximate this data? And I think you guys already know the answer. But just to reiterate, so here's the example from the beginning again, but if I add one letter to it, now I get another 10 suggestions, I can just sort of do a breadth first search here and get more suggestions. And in total, there's about 74,000, 35,000 distinct suggestions if we do this. Actually, I'm going to just do this live just to give you a sense of how easy this is to do. All right, so this is, and you get the idea that you can sort of see the common questions very quickly. And some people don't know this, I think it's kind of cool. You can actually move the carrot back, and it will actually feel like in random places. So you can actually really quickly go through and enumerate these things. All right. I think we have to get back to a spot here. All right. So I actually did that for a bunch of projects. Some of them are listed here, so you can see that between, in many cases, thousands or in some cases, hundreds of thousands of suggestions are returned. I have for Blender here, an asterisk here, just a caveat that when a project has a common name, you end up having to disambiguate between Blender the project and Blenders for ice and things like that. But you can actually filter that out pretty well just by actually performing the searches and seeing what pages come back, and then you can kind of determine from the language of the pages whether or not it's relevant to a particular topic. So now I talked about, for example, with GIMP, we have about 15,000 suggestions. Those are the suggestions, but they actually represent about 2.8 million search queries. There's actually more queries than that, but the thing is that Google, to preserve people's privacy, they do this sort of KNN on amization, so they cut off the long tail. So only searches that are performed by many users are actually recorded in this data set. So we've got data very, very quickly representing about 2.8 million searches, and that's kind of typical for this type of thing. And of course, the popularity of the searches, it falls off sort of exponentially. So the popular stuff is really popular, and then it has a sort of long tail distribution at the end. All right, so I'm just going to give a couple of examples very briefly. So this one here I like quite a bit. It's called, I like to refer to speak the user's language. And again, I adapted this presentation from a presentation I did earlier in the week. So I mean, this is probably pretty obvious to you guys, but in the GIMP data set, we actually see a lot of searches for people asking, how do I convert an image to black and white? And here they're not talking about a binary image. In most cases, they want something that looks like it was an image captured on black and white film. And there's many ways of doing this in the GIMP. You can use a grayscale, desaturate, channel mixer, command, that kind of thing. But the problem is that none of these commands use the words black or white, and that's what people are searching for. So at least it sort of suggests that to some percentage of the audience, maybe they're not able to recognize that these commands are necessarily relevant. So we actually identified over 90 different distinct phrases for the question, you know, how do I convert to black and white? And on average, it's searched about once every 74 minutes. There's a question, yes. Maybe you're going to address that further on in a presentation, but maybe in that case, it's just a random idea. Have you thought about having, instead of just a set of static menus, having a searchable set of menus? Yes. In fact, this factors quite prominently into our research. It's something that I'm working on currently. I can show a little bit about that at the end of the presentation. Actually, my colleague, Ben, up there, is going to show the appable game this afternoon, and search plays a big role there as well. And I think that's a good point. I mean, you can't find one vocabulary that's going to fit everybody. What you want to do is have sort of these aliases, where depending on your background, you can come in and still find what's relevant to perform your task. So another example here, this time inkscape, so a lot of people asking how to crop. They're not thinking about fitting the page to the selection or these other types of things. And here we can see that these types of searches are performed about once every three hours. It's a slightly less search volume. And we can look at another example here. So to make the claim that in GIMP to draw a primitive shape, it's typically a multi-step process, if you want to draw an outline circle, for instance, use ellipse select, use stroke selection. And as a result, we see many, many, many searches for people asking how do I draw a circle. It's searched about once per hour. And that's not the only primitive shape people are looking for. We see like 130 different ways of asking how do I draw various types of lines, in particular, straight lines. 40 different suggestions for rectangles, 20 for squares, 14 for ellipses. So it's just this data suggests that maybe a multi-step process is alluding some portion of the audience for the software, people who are actually using it day to day. All right, so those are a couple of examples of just the types of data you can get from this, and they're fairly high level. But again, we do get a fair, I mean, tends to hundreds of thousands of queries. So we do get a good chunk of that long tail. So you can get pretty specific. I just want to go into how we can start to identify interesting parts of the suggestions that we should focus on. So the problem is that when you get 140,000 suggestions, not all of them are useful for understanding how people use the software. Maybe people are just trying to download the software. Maybe they want to read reviews or something like that. So you want to be able to pick the ones that are useful. And you kind of already saw a taste of that, but I'm just going to go into it in a bit more detail. So in our research, we've identified in this space about six different types of queries. The ones I'm going to look at, though, for understanding people's use are operating instruction queries, so people asking, how do I perform a particular task, or troubleshooting queries. And what we did is we actually, when we looked at these queries, it turned out that if a query was phrased as a question, so how to or can, things like that, it was typically instructions. People looking for operating instructions, so I have some templates up here. The other thing, too, you can sort of see these sort of imperative statements. So anytime you say, like, draw a circle or these sort of the verbs in the present tense, that kind of thing, that also tended to indicate people looking for operating instructions. Whereas for troubleshooting, it tended to be these sort of statements of fact. This is the situation. And the other thing that's useful oftentimes is just to look at queries that have certain keywords in them. The obvious ones here, but just to give you an idea of how to try to filter the data in it, again, a quick and dirty way to get at what you're interested in. And of course, once you've done that, there's a variety of different visualizations and tools you can use to try to navigate all this data. So a simple tag cloud here, this one for Inkscape I have. And I'll actually show maybe a live demo if there's time of some of the data that we have for various projects. So your simple tag cloud here. The other one I like here is the term co-occurrence visualization. So the way that this works, let me see if we can use this. So the stuff down this column here represent the most common words. And then the stuff that goes across horizontally represent the words that co-occur to show up in the same query as these words. So you can see right away here that what people want to do, what people want to draw, well, they want to draw lines, rectangles, curves, circles, et cetera. What do they want to do with color? Well, they change the color, eye color, hair color, et cetera. And so it's just a way of summarizing the data and getting a sense and a feel for what people are interested in doing. And actually before we get into current work and stuff, I will just show some of this. So we have these interactive tag loads. What's this one for? So we've got data for Inkscape, for Scravis, for Blender, for Gimp. And you can kind of, unfortunately, the resolution is a little low here. But you can sort of see what I'm talking about here is if I click on draw, if we connect, I promise it was working before. There we go. You can kind of get a sense of, again, with the tag cloud of what people are trying to draw. And this is filtered on the word draw. And you can sort of see on the right here all the queries that have to do with drawing in Gimp. And so we can talk, we can chat about this data set afterwards, I think. So I think I'm just going to conclude with an idea of other ways that we are looking to use the data currently, and this gets back to your question. So up to now, I've been advocating that we use this data to understand how people are using the software in practice to get a real quick sense of a large user community. But we can also make more active use of the data. So this is some of the work that I've been doing right currently. So basically, when somebody types in a search query into Google, they retrieve documents, tutorials, forum postings, et cetera, and embedded in those pages are references to commands in the software. And we actually, we can produce a list of commands by instrumenting the software or just by looking at the localization database or the string database. So anyways, what we do is that we perform the search, we retrieve the documents, and we identify the commands that are in those documents. And when we take our giant data set from Google Suggest, we can actually create these really fairly large graphs. Sorry? Do you identify the commands manually or automatically? Well, with Gimp, we just use the in Gimp data set. So in Gimp, because it was instrumented to record all the command invocations, we had a list of all the commands. But for other applications, I didn't want to have to instrument those applications to get the names of the commands. So I did it in a kind of hackish but very quick way. So again, I just looked at the translation files, like the string translation databases, and now I have all the error messages, all the menu names, all the command names, and it was just very quick. In any case, when you do that and you take this very large data set, you can create these associations, these graphs. So query is on one side and commands on the other side. And what you can do then is you can build a smarter sort of command search. So if you integrate search into the interface, if I want to say convert to black and white, it's going to come back with, based on just looking at the pages that Google returns, you know, channel mixer, grayscale, desaturate. And it's a search engine. So the rankings here may not always be the best, so maybe desaturate should be above channel mixer, but we've got a pretty good result there. And similarly, you can kind of do command recommendations, if you will. So if I ask what commands are used in a similar context to stretch contrast, you see that white balance auto levels and colors are also used in that context. And then the other thing we can do, so that's going from this direction, so going from queries to commands. But because we have this graph built from all of these queries, we can go in the opposite direction. So from a command, what queries are associated with that. So here's something that I'm working on right now. This is just a mock up. But suppose that this is a tool tip for the ellipse select tool in GIMP. Well, based on the data that we have, we can say that, well, ellipse select is related to the following searches. So draw a circle, draw an ellipse, text on circle, correct red eye, vignette effect. And you can see what other commands are associated with that. Now this is generated by the user community on the fly. So it's sort of evolving as people use the software evolves. And the nice thing about searches is that if you think about what you're doing when you type in a query, you're trying to come up with this very concise information rich phrase to describe what it is that you're doing or what you're looking for, your information need. And so I think that these queries here, they're compact, but they give a lot of, they give a pretty good indication of what the people are after when they were typing those searches. So this is one way that we're looking at integrating this data into the application to make it actionable. So I think that really concludes everything I wanted to say today, but I'm more than happy to take questions at this time. So aside from all this looking very, very interesting, the one factor I wasn't sure if you looked at yet is if when you're phrasing things and maybe thinking about, as a developer thinking about using these results to change the phrasing of what you have in your application so people can understand it better. What's the, have you looked at it all, is the reason you don't get searches on other phrasing is because it's a good phrasing to begin with and you're making more people happy and only the unhappy minority are going out to search for things and you might make things worse rather than better by switching. So I think that one thing I probably should have mentioned going into this is that this is a way of, I would say, doing a pilot study in the sense that if you want to, so everybody talks about doing usability studies or just observing people use your software, right? But what you want to do is you want to put people into situations that a lot of people want to perform these tasks and you want to put people into situations where you're going to get some sort of value from that user evaluation. So when you run these queries and you get these queries back, it's a suggestion to watch somebody perform that task and if they're having trouble then you can try to get some insight from these follow-up observations. But it might turn out that it's not a usability problem, it's just a very popular task that people want to perform. Yeah, to kind of build on that, so that's a good question, John. But I think you can look at some of the numbers we have where like when people are querying some of these things like on an average of once every 30 minutes, that some of these things are fairly big problems or there are things that a fair number of people are searching on. And so yeah, we're not going to get the stuff where people know how to do it and therefore they don't need to search for it, right? But as he mentioned earlier, there isn't necessarily a one size fits all interface. And so having this ability to search like he showed with the, can you go back to like the, where you're, yeah, so like having this ability to type in, this is what I want to do and then it comes back with the actual command names in the interface, might be a way to kind of bridge the gap between people who use the vocabulary of your application and those who are unfamiliar with it. So I'm just curious about the, what tool you're using, the scrape or whether that's publicly available, like for instance the digital methods initiative, you can use all of their stuff, but just curious how you're getting these query suggests. Okay, so when I, so it's actually a good question, when I'm actually grabbing like these thousands of query suggestions, that's a parole script that I run and I don't make it publicly available because quite frankly it's sort of in this gray area where we're using the same interface that Firefox and other web browsers use to do query suggestions in the search box in the corner, but I'm not entirely sure. I don't want to release it publicly because it's in this bit of a gray area because we are sending automated queries. What I'm suggesting to you guys is that you guys can get a lot of bang for your buck just by typing in queries manually, which is perfectly fine the way I showed you, and get a fairly high level view of how people are using your software. Oh yeah. So by typing in these types of things. Which is not to say you couldn't go and write the same parole script yourself. It's like half a page. Okay, another question about this graph between queries and commands. Yeah. Do you have a tool to make this relation or is it has to be done manually? Well, I have a tool that does it. I didn't want to get into the details too much, but basically this graph here, it's using some techniques from information retrieval literature to do question answering. So basically what you do is you build a question answer engine. So instead of like a search engine, you want to be able to type in a question and get just like the name of a command or whatever as an answer. So I built that engine and I performed those queries and I just stored the results in the database like almost the cache. And then that is, it's just a bipartite graph. Well, because I remember like like Cetorate and Black and White, they don't have any common words. So how do we make the link? Oh yeah. So basically the argument is that these pages act as like a Rosetta Stone. So a tutorial is telling people how to perform a task in the software. So they're going to have to mention the command names in the documents. Now in order to be retrieved for that query, they also have to have some words in common with the query. So by performing the search, retrieving the relevant pages and then by extracting the command names from those pages, you've linked the two vocabularies. Okay, thanks. Any more questions? Okay. Thank you very much. Personally, it's wonderful. I understood what it is. Thank you very much.
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Every second of every day, people use Google to troubleshoot problems and to learn how to accomplish their goals. While Google doesn’t make its search query logs publicly available, Google Suggest can be used to learn the most popular queries for any software. We systematically mined all of the query suggestions for GIMP, Inkscape, Blender, and Scribus to learn about the primary needs and problems encountered by users of these software applications. As examples, our technique collected ~15,000 common queries for GIMP and ~2500 queries for Inkscape. In this talk, we will present samples of the most common search queries for these applications, and what they suggest about the software user bases and their needs.
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10.5446/21718 (DOI)
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Okay, so in order to save time, I kind of planned this presentation around the assumption that everybody in the room knows what video editing software is, what open source is, and what the Linux platform is. So before I go any further, does anyone not know this or does anyone need some quick clarifications? Yes, no, okay. So for those of you who saw my talk in 2009, you might remember that I compared G-Streamer to a giant enemy crab. So yeah, this talk is pretty much centered around PTV, but it's also going to cover the state of the giant crab of video editing on Linux in general. Yeah, so I won't go over the history of the PTV project since I already did that two years ago. So if you care about the history of the project, you can go look at the video recording of 2009 or by a time machine or something. Anyway, you can find the link to the video recording on this huge URL or on my personal website. Instead, here's what I'd like to wet your appetite with today. So to start up, this is a bird's-eye view of the state of Linux video editing. You can still see the various camps, the G-Streamer camp, the MLT camp, and all those independent video editing applications. Just let me start something. Okay, so yeah, all things considered from the user's point of view, you see applications maturing, frameworks maturing, a bunch of new weird things coming out of the caves and so on. And so by the way, don't be offended if I didn't list your favorite app in here. I'm just simplifying a lot in thinking in terms of engines. So anyway, you'll get to see all the other apps later on. So this pretty much looks good, right? It looks like there's some kind of healthy competition going on and various camps are advancing. Not exactly. Are you guys ready for the cruel, shocking truth? Okay, so what happens is this. Welcome to the real world. Most people don't care about the little guys on the Linux map. You can see most of the cool kids playing happily on the table over there. And they're using like iMovie or Moviemaker or whatever came with the CD of their camcorder or whatever they could get from a shady guy in a shopping mall in Hong Kong. And the guys in blue, they're the guys from Avid and they're too busy ringing the cash register to even notice you. So anyway, I'll get back to the open source Linux video editors battlefield at the bottom in a few minutes. So for a few seconds, I'd like to take a look at this broader view and ask the question, why don't those two worlds intersect with each other? Why are we not seeing, say, premiere on the Linux battlefield? There are many, many, many reasons for that. One of which is market share. I guess I should exclude smartphones from this figure because doing serious video editing on a smartphone is like kind of silly. But then at the same time, we would have thought a hundred years ago that we would have cameras embedded in phones and that the main use of a phone would be not making phone calls anyway. So what you can see basically is a big majority for Windows here. Linux has maybe one to 1.5% of market share and according to the last trends I've seen. And in 2008, we passed one billion personal computers. And so when you think about it, 1.5% of more than one billion computers is still a lot. It's about 15 millions and that sounds about right, I guess. But what happens when you combine that with the fact that not everybody does video editing? What is the intersection of a Linux user and a video editor? According to my rough estimate, according to Ubuntu's popularity contest, that's about 4% of Ubuntu users use PTV. If you take other video editing software into account, we may have maybe 10% of Linux users. Anyway, as you may know, my data might be completely wrong. There are many problems with this statistics sample. It's just a bulk-work figure for me to know that we are in a niche market. I mean, we're at 4% of 1%, but you can't be more niche than that. Is there still a need for this? I guess there is, because there seems to be a sustained interest in PTV, strangely. According to website statistics, there are between 13,000 and 20,000 visitors per month. This graph is kind of outdated anyway. So we covered the market share, so that's only one of the many reasons why open source video editors suck. Here's another one. History keeps repeating itself. Recently, I've done some research and came up with a timeline of all the open source video editors I could find. I'm pretty sure you've never heard of 90% of those apps in the timeline. That's because they failed anyway. Look at all those independent lines. They're all reinventing the wheel and even the enduring ones, the ones that survive the natural selection. They all pull in different directions. The problem with that is that it fragments the resources. That is, the few developers that are crazy enough to try to make a video editor. Those are a couple of factors of failure. I wrote a term paper on that. Targeting Windows and Mac. What the hell would you ever want to do that? Increase this complexity, more bugs, more one-powered, wasted, competing with commercial offerings, and having users that generally don't give them an open source sometimes, or that will complain that they cannot import their PowerPoint file into your video editor. Anyway, another key point of failure is thinking that it will be simple and that you will succeed where all the others failed, and thinking that it will only take a couple of months. If you think that you failed before even it started and your competitors will outpace you before your first beta is out. On the other hand, the key factors of success, well, I guess, be open source, run on Linux, be easy to install, support as many formats as possible, have a nice UI that is intuitive and pleasant to use, don't crash all the time, have a team of knowledgeable core developers to do the maintenance and the complex tasks, attract contributors to work on the cool features and foster a healthy community. For one thing, PTV is the default video editor on Ubuntu. Okay, that's not saying much, I guess, but it kind of provides some sort of legitimacy and validation for... maybe it's not complete crap, I mean... I don't know. Canonical estimates... that's Canonical, estimates its user base at 12 million users. That might take a drop with the recent events around GNOME. Anyway, what this means is someone who wants to contribute to the video editor with the broadest potential for impacting the lives of as many people as possible, needs to look no further than PTVs, and it's installed on millions of desktop computers, not based on the theory. And that's probably not going to change anytime soon due to architectural or legal reasons. I naively hope that we would see patches and contributions coming from Canonical, and that being installed by default would mean that we would get more contributors. I guess that was kind of wishful thinking. Anyway, what makes PTV a worthwhile project? The fact that it uses standard technologies like G-streamer, which we all love, I guess, it's pretty much the biggest... G-streamer is pretty much the biggest multimedia platform framework kind of thing on Linux and other platforms, I guess. As to upstream first means that when you spot a significant problem, you fix it directly in G-streamer, which means it's better in the long term, but it also means that it takes a really long time to get there. So I think it has more chances of survival in the long term. And another good thing is PTV is basically a torture test for G-streamer, in the sense that all the other G-streamer applications benefit from whatever bugs we might find in PTV and fix. So in terms of user interface, I spend a lot of time thinking on PTV's design to make it really simple and intuitive while not limiting what you can do with it. Yeah, G-streamer, we love G-streamer. For those of you who are actually not familiar with G-streamer, it's basically a toolkit for software developers to deal with sounds, images, videos, and special effects and all that stuff. So what this means for PTV and other G-streamer apps is that you can get access to a huge combination of multimedia plugins. You can encode and decode pretty much anything, except Danny's AVCHD and MPEG-CS files. If you have the right plugins installed. Anyway, this means that you can use a wide variety of formats, from the $100 pocket flip-like video camcorder thing to the point and shoot and the DSLR. What's quite interesting these days is that those cheap point and shoot cameras allow you to record high-definition footage. That is much, much better than what I could do with the DV camcorder a couple of years ago that costed twice as much, at least. Anyway, so great compatibility is great, of course, but it's not everything. Design is important too, and it's not just SACED-FIX. It's a matter of thinking about how your users will interact better with your software and trying to do better than, let's do a clone of Adobe Premiere. Or let's add an option from everything approach. Otherwise, you end up with creeping features. That's an actual screenshot from Sony Vegas. Anyway, I described my point of view about options in 2009, so you can use a time machine and go see my talk. I won't be going over this in detail. Anyway, all those things are completely useless. I tried to find a useful option there. It isn't. You've already been around for a long time, but it's not. Oh, yeah, and I totally need to choose if I want to show you a splash screen at startup. I mean, oh yeah. Anyway, in terms of UI design, PDV, I guess it's quite good thus far. The problems are the usual bugs that are hard to troubleshoot and take a long time to fix. And when presented with this user interface, most people think like PDV aims to be a clone of Windows Movie Maker or iMovie, and that's that. But that's not true. I mean, it aims to be much more than that. I just rewrote the roadmap on the Wiki recently so that people wouldn't get the wrong idea. Yes, of course, it doesn't do much at the moment. That's because these things take a lot of time to implement. So the vision behind the project in terms of design and feature set is much, much greater than what you can see in the current implementation, in the current state of the software. And I believe you can design a user interface that is both intuitive and powerful that would suit both Joe Plumber and that cool kid who's going to make the next indie blockbuster thing. And so you really don't want to artificially limit creativity. And that's not that you're not in a commercial world thing. You don't want to segment the market into low and high end and try to sell to both at different prices. Anyway, is that enough? Not exactly because you need a strong foundation, I mean, strong software foundations to attract new contributors. But getting those foundations built is real hard. Just like Linus once said, don't expect people to randomly just jump in and help you do it from the beginning. You need to get it almost working for them to be interested. So the way I see it, basically, it's like maintaining such a big project. It's like maintaining the international space station. You need professional core contributors that take care of the maintenance and complex internal development, while in order to attract external contributors that will tackle exciting stuff. And one of the great things about being in a niche market is that our users are kind of hardcore. I guess you can see that as a good or bad thing. But then why are we not suddenly overwhelmed with patches and contributions? Part of the answer, I guess, is that compared to a lot of other free and open source software out there, the users, which is the filmmakers, are usually not programmers. Only 2% of the visitors on the PTV website check out the contributing page. That's 2% of 4% of 1% folks. And on the other hand, the software developers, they are usually not filmmakers. At least they are not anymore, because they're too busy developing software. So combine that with the fact that a video editor is a complex beast and you have a vicious cycle. So what is the solution then? It's easy. Just sell the software, right? Not really. I mean, in theory, you can try. In practice, pretty much nobody does this in free software. I mean, even asking for donations, not sure that would work. Because most people with a brain would make a quick economic analysis and think, wait a minute, why should I pay for some incomplete app when I could spend $100 on a commercial application that would do everything I want, probably, without needing to wait 10 years? So here come what I call the indirect competitors. The guys in the low end segment, they are the ones who worry me. Well, the guys at the high end, too, they worry me, because everybody is going to get it from a torrent website or a shady guy in a supermarket alley in Hong Kong or something. So it's not really possible to think that you could have a direct revenue stream for the average user. And as Eugenia said a couple years ago, and I quoted her two years ago, a video editor saying it's a complex problem that requires professional developers to work on it. So you're in this strange situation where a developer costs $100,000 per year, and it means you have a choice, pick any of two, cheap, good, or fast. Getting good and fast would mean that you'd have a strong business model around it or really, really deep pockets. So now you're in a better position to understand why we still haven't seen the perfect open source video editor rise in the last 10 years. Now that I've got you all depressed, let's look at the upside of things. PTV does have some sort of backing in the sense that there have been multiple students working on the project as part of Google's Summab Code program. And there are some Collabora employees working on PTV in their spare time. Does that help? Does that make a significant difference? Yes, it seems so. Involvement from Collabora helped, and the various Summers of Code helped a lot. Example for last summer, Cibo, Betune implemented video and audio effects, and they were integrated in PTV. But this is not yet released in a stable version. And just yet. In Summers of Code helped a lot in implementing major features. But we're always looking, of course, for new contributors. There's a nice set of instructions that I wrote on the website and the wiki, and there's a list of easy things to tackle for newcomers. And I'm really quite excited about what will be the result of this year's Summab Code, as we will have four students working on PTV-related projects. So those are some of the things they will be working on. GES stands for GStreamer Editing Services. I'll come back to that in a minute. Animated effects mean being able to change the properties of an effect over time. So you have, you say, for example, go from black to white to full color. And clip transformation is being able to easily rotate crop, resize, pan, do stuff like that backflips with the clips on the canvas. Titles is being able to create text onto your video instead of using Inkscape and exporting a PNG and having a ton of bugs because of that. But there's already some good work done for this, but it just needs someone to finish it. Another feature is render profiles, which is being able to have a default set for easy templates to export, to say DVD or YouTube or email or Blu-ray, iPod, smartphones or toasters, anything. So on a related note, video uploading is also being worked on, is being able to have a wizard that renders your project and directly uploads to YouTube. And one of the Summer of Code students, Ferrode, already has a working implementation of this feature, so it just needs some polish because the UI is horrible. I mean, anyway, it needs some testing, and then it can be integrated with all the rest and it's going to be awesome. We'll be able to post videos of dogs on skateboards on YouTube. And we currently have some basic support for presets in project settings, but not for rendering settings, and we don't provide a default set of those presets. So that's hopefully going to be fixed too. So in that list, you've probably been wondering what the hell is that optical flow thing. It's quite an ambitious Summer of Code project for G-streamer that PTV might benefit from. From my understanding, it's being able to cut out parts of a scene and do compositing on top of that. And that would be managed semi-automatically, hence the optical flow thing. That means that instead of manually animating every single frame, the computer would do part of the work for you by analyzing the visuals. And that means that if you want to do the next die-hard or Star Wars movie, you can add big explosions and lightsabers without needing to edit every single frame in GIMP. So what about GES? It's basically another abstraction layer that allows you to create apps like PTV or Jocosher or Lombard more easily. Yeah, I can hear you saying, what? Another library on top of all this. Why? This is why, according to Edward, why do we need GES? Basically because hacking on PTV still feels too complex. And I guess because nerds love libraries. So yeah, let's recap. Basically, the current situation still sucks for most users. Hopefully after GES is implemented and PTV will be able to write ponies on rainbows and be heavy ever after. We are in an interesting situation, interesting times ahead because we are all, well, not we are, oh, I am, I guess, living under the impending doom of being wiped from the surface of the earth by the crushing superiority of lightworks that proprietary app that is supposed to be open source, they said that a year ago or two. And if it is in these, that's open source and if it is really, really good or not, maybe, I don't know, it will be really interesting to see also what comes out of this year's sum of code projects for PTV. So yeah, the website has a really nice set of pages for new contributors if you have problems getting started, you can always feel free to come and see me. And yeah, that was kind of a nonstop stream of blah, blah, blah, blah, blah, blah, blah, blah, blah, blah, blah. I don't know if there are any questions. Any insults or, yeah? Hi. Maybe I can just reassure you about the nations, asking for the nations does work. Really? And yes, we got about 70,000 euros of donations last year which enabled us to have two people work nearly full time for about 50 months in total on Krita. And a question that came to my mind was, what do you do with the donations? I keep them in my bank accounts and I hand out the money to the developers when they have completed a month of work. And this is also important and this ties into another of your points. Using your stuff on Windows will easily travel or maybe make the amount of donations 10 times as much. Just check with the GIMP guys how much of their monthly donation income comes from Windows users. I understand the economic reasoning, okay, I can get a professional app for $200 and so why should I pay $10 for an open source? People like doing that. And it really works. But then I thought about that, but then I was wondering, well, first the PTV guys don't have the manpower to maintain the port to Windows and Mac and so forth. I mean, they barely manage to keep the bug gates non-flooded. If there could be a Windows version, I mean, do people on Windows really want an open source video, it's the app when there's like so many choices of apps there? I mean, my strategy was to think we might want to concentrate on where there is a huge, painful need on the Linux platform. They can download Photoshop for free, they can download any image editor Windows for free and they mostly do. But I don't know how many millions of downloads GIMP gets on Windows, but I do know that I get about once or twice a week and Crete has still a relatively unknown project. Oh, why isn't Crete available on Windows yet? I would really like to use it. My wife would like to use it, my girlfriend would like to use it, my dad would like to use it. There apparently is a demand for people who don't want to steal software and don't have the money to pay for a professional app or don't trust professional apps. So the GIMP team isn't big either. Well, I mean, whenever you have a camp corner, there's an app that comes on the CD too, so just to nuance a little bit. Your graphics tablet usually comes with an app as well, but those apps, there's demand for it. So if you manage to release the Windows, you might get even more donations. Yeah, two comments. One, I'm in the MyPain project and we also have about 80% of users from using Windows and we do not put a lot of effort into the Windows port. I mean, we have a guy maintaining an installer, stuff like that. Using the little developer time basically needs to go into it to make it workable. We use GTK and Python and stuff like that. And I don't think it would be that much of an effort for PTB editor. Complexity is not high. Below it is higher. Another thing is that I have an experimental proof concept patch for Gaggle integration in G-Streamer. So I'm going to discuss that with you later. Adam, how did you guys, you guys were going to have a video editor, right? And you figured out some economic model. Yeah, well, I guess a couple things. And so I'm going to get flamed. What's that? No, no, no, no, no, no. That's not what we're here for. For those who don't know, we're from Yorba, makers of Shotwell. So sort of along this Windows line, I guess sort of as a counter example, for some of you may know, we actually had a Windows port of Shotwell for a while. And it was because actually a potential donor from Google sort of stopped by Yorba and said, hey, I'm excited about Photo Manager. And he wanted certain features, but he said he really wanted us to work on Windows. So we actually did good on that path for a while. And we had it working on Windows, I don't know, for releases in succession. And eventually, I think around about six months ago, we decided to discontinue the Windows port just because the donor had disappeared to nowhere. And for us, it wasn't so trivial. I mean, in particular, we've actually had ports on Linux where we normally run on Windows, and then we even got it working on the Mac for like a day. And our basic experience was GTK on Linux is wonderful, of course. And Windows kind of hobbles along, but there were many small glitches. It depends, to some degree, on just how much polish you want. On MacOS, it's just broken. I mean, we couldn't get it to work at all. So our conclusion was there. We could have kept it alive. And again, maybe if the money had come, we would have invested it, but we thought that would have been at least, I don't know, one developer worth a time or something moving forward. Anyway, URBUS also worked in the past on an audio editor, and a video editor, also based on G-Nonglin. And for better or for worse, Shotwell has been so successful. It sort of has taken all of our attention, and our video and audio projects on hold. Our experiences there were, we actually found G-Nonglin worked pretty well for video. Video in some ways is harder, just because you have to think a lot about low latency. And so trying to record is tricky. Anyway, we can talk more about that later. Yeah, definitely. Thank you very much. You know, Hosoel? Yeah. I think it's... Yeah, more? More questions? No? Okay. Well, thanks. Important question. Thank you.
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What has happened since I first presented Pitivi at LGM in 2009? This talk will address the following topics: * Quick recap of the current state of open source video editors in Linux * The challenges of open source video editing * New features and improvements in Pitivi since 2009 * Why Pitivi shall prevail, and how to get involved * Near Future plans for Pitivi
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10.5446/21720 (DOI)
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So the talk is titled My Paint, the past, the present, and the future. We'll go through the past really quick, giving an introduction about what My Paint is, how it got started, and some parts of the development up until now. First, about me. My name is Yulin Mube. I also respond to John, if that's easier. On my spare time, I do My Paint, Open Raster, mainly. I also do some GIMP development and some Gaggle development. In my day job, I work at Openismus, a company in Berlin specializing open-source software, and currently working on contracts doing Nego work. So the past, it all started in 2004, when Martin Reynolds decided that, yeah, I want to do a bit of creative arts. And I want to draw digitally. I'm not too interested in traditional media, and I'm not happy with the solutions that are out there. And his focus was really on the creative stuff. He just wanted to draw. So he is an engineer. At that time, I was a student. And he decided, yeah, I will just do it on my own. He started basically with a plain input window and a brush engine. He kind of went input window and brush engine. He had some ideas what he wanted to do with the brush engine. And an interesting thing is that it's basically the exact same brush engine we used today. It just added some stuff. And it's a really simple brush engine, but it really works. So his motivation was to make something that he liked using and like developing, of course. So the initial versions looked something like this. This is now like every dialogue is on the screen. But you see the main window where you will actually be drawing is just a canvas and a menu bar. So really, really about the drawing parts. And he typically works by having, well, nothing like this on the screen, just popping up those dialogue windows when he uses them. So he basically has a full screen canvas all the time. Yes. So this is an initial version of the brush engine. This dialogue just gives you every button and thing you can imagine and kind of corresponds directly to how the brush engine works. These are ways to define dynamics. So every kind of setting you see up there, like opacity and other strange stuff, hardness, radius, can depend on stuff like the pressure or the tablet, of course, the speed you move, the direction you move. So it's a really dynamic system. And all brushes are procedural. So between 2005 and 2008, Martin basically continued developing on his own. Added more and more features. We got really kind of a unique feature pretty early on, which is infinite canvas. So you basically just start with a blank canvas. And once you start painting in some direction, well, your canvas is that big. So it's as big as you need at any given time. And artists really love this because, one, it means you don't have to choose when you start up, oh, I want to do something that is x big, because that kind of kills creativity. And two, is like, I have these constraints to actually paint beyond to change what I was doing right now, I would have to go into some dialogue, change the size, sometimes through really crazy dialogues and not good UI. But even if the UI is good, it's still a switch from the creative mode of just drawing your totally into the art to kind of fiddling with this computer thing that you don't really care about on this software. So in 2008, it looked something like this. And it didn't change much in terms of the UI. You see here is more typical way of using. You have the entire canvas basically spread out. You have a menu bar at the top. You have a color selected. This is a standard GTK one. And the brush selection. These are the two typical actions you do. You change the color, and you change your brush. And it's, yes. So what happened? Why did I put 2008 here and then 2009? Well, up until now, Martin has been developing basically all on his own. He got patch sets, like four or five patches about something specific. But in general, it was his thing, and he did all the work. In 2009, people started joining in, switched to Git for version control, kind of spurred things up for some reason. I joined, and we had some other contributors that were with us for a long time. And now it's more of an actual open source project in that you collaborate and you do different things. So and here, more features were added. I forgot to say that in 2008, we got layer support. And then, my pain was the first application to use OpenRaster as a default document format. So that was kind of important for OpenRaster. And also, in these years, we kind of have, because of that, we've been kind of the ones pushing OpenRaster lately. OpenRaster, as you know, is a format that started at LGM and still is kind of developed around here. Yes. So this is how it looked like, basically, with the latest release version. There are no huge differences. We've got a layer dialog, actually, for one major release. We didn't have a dialog for the layers. You just had keyboard shortcuts. Now it's a really basic dialog, but it kind of, that's what you want. And a new color selector. I'm not very happy about it myself, but it's there. Some people like it a lot. So the present, I should have hooked this up, but I want to show you a bit of my paint. I'm just making sure that I don't have any configuration things. So this is the latest released my paint. It is available in all major distros. So in the latest version of your distro, well, most definitely, it's available in all major distros. But most definitely have the latest my paint release, which is 0.9.1. Yeah. I forgive me for my quite special desktop environment. It's not what you typically see. But this is kind of how you would start. This is the default startup for my paint. So you have just showing you that you can select colors and that you have several brushes to choose from. So these brush sets that I'm currently in are we have two artist brush sets, one called DeVod, which is David DeVod, who works on the Durian project. It's a really nice brush set. And we have Ramon, which is Ramon Miranda's brush set. He does Gimp Paint Studio and also, in general, is active in many, many projects. So the default presets show what the brush engine can do in a pretty comprehensive way. We still have a challenge. And I will show it to you. Do you recognize this from the first screenshot? It's exactly the same as before. This has the advantage that, well, it gives you every button and tweak that you can do as far as the brush engine goes. But could you tell me which ones of these switches, or sliders, buttons are relevant for the current behavior of the brush? Most likely, you couldn't easily do that. And this is the problem. So this is something we're working on right now, slightly, at least somewhat. And we have the same issue here. It's not obvious which ones of these are relevant or what they do. So that's something that we need to get some love finally, since it's basically been the same for, well, six, seven years now. And I want to show you some unique features that MyPint has. A long thing about workflow first, it's kind of designed for a tablet and keyboard usage. So you kind of have your tablet at all times. But using your right hand or left, if you choose so. And then a keyboard. So we don't do flip over tablet PCs very good, because it's kind of keyboard-centric. That's also something that we're looking to improve. It's just that no one of the current developers have such a machine. So one of the really nice things is, of course, the infinite canvas. I mean, I start doodling here. And then I decide, well, this might be a nice doodle. Sometimes you just want to, I don't want to do the new document. I just want to do some other doodling. And you just move to the side. You draw on, well, you can do as much as you like in any direction. And it will all be saved. And you can just go in any direction. Don't worry about document size or anything like that. It's really unnecessary most of the time. Another nice feature that you don't know what I intended is what we call a context picking or a brush picking. So we actually store the data about what kind of brush did you use at any given point. So you press W by default. See now I have the pen brush. Here I used some other brush. You press W and you actually get that brush, which is quite awesome in practice because you do a foreground, well, not necessarily a foreground layer or stuff like that, but you paint some foreground. You paint some details. You use different brushes. And you don't really care about which brush you use. But very often you want the same brush or something very related to it. So you see the effect of that brush. It's like, oh, I want now that, but it's likely bigger or whatever. Pick it. And then you do some tweaks. And this is something that once artists have incorporated into their workflow, they don't like doing things otherwise. Yes. Those are the two major features that I want to show. Now I'll go slightly over to just show the development version and some of the changes we had. So one feature actually comes up right away. I said that it's kind of intended that you have a full canvas. You pop up the dialogues as you need them. But in practice we see that a lot of people want to kind of have every dialogue at the same time. On a screen like this, it doesn't make sense. But if you have a huge screen, you can basically keep everything up to the side. And people did this by positioning the windows manually. Instead, we basically said, OK, we will do a simple mode where you can just dock things to the side, which just really helps that kind of workflow. Even though it's not the main workflow we want to promote, it is a useful workflow. So that's a new feature. One other thing is that this infinite canvas really promotes creativity. And artists generally really like it. But you have some problems if you want to do or challenges if you want to do more design things. So you're creating a poster. It needs to have a certain physical size, or at least pixels, by size do you want. And well, how do you do that? There's nothing here that tells you, well, this is x pixels, or this is given dpi, and dpi this is x inches. So people say, oh, we actually do want a definite document size at some point, or canvas size. And we basically, this is the oldest bug or feature request going back almost five years. And the challenge here is that we didn't want to do a mode so you would switch over to, OK, now your canvas is this big and it can only be this big. So you wanted to preserve the creative workflow that you have with infinite canvas. So you just expand whatever you want. There's no hard boundaries. And we basically have the start of this feature right now where you can do a document frame. And you give it some size. And you know what. And basically this looks like the cropping feature in GIMP and other software. And the important thing is that you draw within these boundaries most of the time. But you can still extend out at any given time and have this easy way of just like, yeah, you can go do that. We want to enable people to do that still. When you save to a PNG, this will be cropped to the given document size you set. But if you save to OpenRAS, start working document format, we will save all the data by default. We might introduce some destructive like, now you say I want to really crop this document. But in general, we save all the data. So this is new. What we'll be, it's kind of blocking the 1.0 release, is having some proper UI for moving this. So this should all happen on campus, of course. And yes. And also we added just minor things, more preferences, different places, in terms of your input devices mapped to. More importantly is that we now fully track the different input devices. So now I'm using a kind of a pencil tool here for the tip of my pen. However, you can switch to the other side and have a eraser brush. So you can kind of keep those in even time. So but there seems to be a bug. Not nice. That's the general idea. One other feature that I would like to highlight while we're at it is the concept of an eraser mode. So I just do some, you can use any brush as an eraser, which kind of can give you this workflow that is common in pencil, traditional pencil art, where you draw, but you also kind of draw with your eraser, these kind of a stub eraser, like these, for instance. But you can then like, OK, I have some, these are all not so interesting, but what about the, OK, so this is like an airbrush. And we can just switch this to be an eraser. So I would actually now simply erase parts of the stuff I previously drew, which kind of can enable nice workflows. So that was the present, more or less. We hope that, I actually hope that we would have 1.0 done for LGM. It did not happen. There was not a lot of activity the last couple of months. So it looks like it will be in a couple of months. One thing to note with my paint is that the GIT version is really, really stable. We basically do not have pressure issues. And we have artists using it in production. And it's simple to build. It uses Python mainly. So if you're an artist or a developer, you can easily get, well, if you're comfortable with the command line, you can get it and use the GIT version. And there's no point in really waiting if you're anxious for some new features or just trying it out. So future, we have some concrete items coming up in the future, one being that the Python 3, so we will move to Python 3 at some point. It's kind of becoming time to do that. We will also move to use PyGT object and introspection instead of using PyGTK. It's kind of another technology change that's happening kind of below us. We will probably do that after 1.0. Well, we will do it after. And the next thing, those are the concrete items that we have. Then there's more about visions. Where do we, or where do I, I'm only one of the developers, see mypng going. We now have the general trends that Krita especially is becoming a really, really awesome application for the full set or full workflow for painting, drawing, and all these things. So maybe we want to position mypng officially more as a sketching tool and focus on the simple, creative tools. The thing is that most artists use mypng as part of their workflow. They start in mypng, for instance, going to Krita to do, maybe they do even most of the work in Krita. But a lot of the more active our mypng users use mypng for like 80% of their stuff. And then they, for instance, quite commonly important to game to do final crop, color corrections. Sometimes they do do stuff in between. One lack we have right now is there's no different compositing modes. And we could add layer modes, but we're kind of more interested in having brush modes. So you have a lightened brush, or you have an overlay brush, or you have a dodge brush, instead of kind of forcing people to deal with layers when they just want to lighten or get that kind of effect. So right now people transport to GIMP to do that kind of stuff if they like it in their workflow, which is kind of why I did the OpenRacer support in GIMP for the first place. So interchanged is really important for us, because we are, and we will forever be, just part of the workflow that, well, we don't aim to have all the sets of tools that Krita, for instance, has, or GIMP. And one thing I hope to really emphasize this point and really kind of really build on it. And I hope to do this by moving the brush engine to Gaggle. So the entire document would be described as a Gaggle graph with some wiping operations. This means that you could then import it into GIMP, and it should be much faster operation to import it into GIMP once GIMP does Gaggle a lot. And to have the entire document kind of understood by GIMP, like every aspect of the MyPaint stuff, or maybe not every, but most. And then, perhaps more importantly, allow people to do all their GIMP operations, but have MyPaint at least have a basic concept of all those things you did in GIMP. So the cropping transformations, all those things we don't really want to implement on our own. But we really want to enable as part of a workflow. So that's, and then hopefully we could, if we had a common base with GIMP, maybe we could even do crazy stuff, like having GIMP and MyPaint edit the same document. So basically, you can just alt-hub. And you have GIMP as a UI available, and all the action is exposed. And then go back to MyPaint and kind of just go back into your creative spirit and just do that. That's my hope. Yeah, and I said in the abstract that I would tell something about how you can influence MyPaint's direction. And we have a lot of artists, but we always like to get a feedback. It's really important for us. It's important for everyone, but we encourage it. But in general, we need developers. Code is what makes software. And we are a very simple application. I mean, we have a narrow scope. It's 10,000 lines of code in Moinly, Python. Simple stuff, UI code mainly. A brush engine that is like 2,000 lines of code. And it's also quite simple conceptually. So it makes it a good project for contributors that are starting out. And we are also, I would say, really friendly to new contributors in a small, tight environment. So you kind of get to interact with the core people at once. It's not like there's any barrier things like that. So I really encourage anyone who's interested in trying to do some development. Maybe you are a developer already. But come to us. And if you like MyPaint or want to help out. Questions? What does it mean? Come to us. Because we will be streaming this. So maybe you can tell what it is. Our website. We have then a simple page for contributing and showing the communication channels we have. We are basically, I'm on RSE all the time. So you can join us, hash MyPaint, FreeNode. And we also have a mailing list where all the developers are, at least. Not so many users, but it's also free to use. And it's pretty well documented on our website. So I don't know if this is going to be really a useful question or not. But I'm always amazed. How is MyPaint so fast when it comes to such huge images? And even the GIMP is written in C. And when you get to really big images, it just gets slow. And MyPaint is written in Python. Do you have a C back end for this? Or is it just super smartly written? Or what's going on here? Actually, the back end is quite an interesting story. We have the back end mainly in C++. It's basically C with classes. So that kind of, we move stuff that needs to have good performance that we cannot achieve in Python. We move it down there. And we have a brush engine that you can separate out. It's not too easy at the moment. But that's what Krita has been using. And we have the UI that kind of exposes how you draw in that stuff. And then you have the brush engine between which maps inputs to kind of the dabs, which are just like circles you put on the screen, which makes up the stroke in the end. Underneath that, you have the surface implementation, so what you're actually drawing on. And that is an interesting thing because it's written kind of, it's a C++ interface. But we actually use Python dictionaries for the tile structure. So we kind of have this fairly well optimized structure that we kind of just use. And that's kind of the trick, like do what needs to be, is performance critical in C++ and use existing well optimized data structures. I would say that's the trick. But it's also a really simple brush engine that helps. Thanks. Just one thing. It may help when the person starts a project as an engineering working on embedded systems. To keep it. Yes, Martin has a background there, so he knows some tricks. No, no, no. Hey, just solely because it came up in the CRETA talk, I was wondering if you had thought about multi-page documents or if OpenRaster already supports that, and I'm just not aware of it. And no, OpenRaster does not support multi-page documents. There is a film, the art director of a film in Berlin that's currently using MyPaint for concept art. And basically what he does, which is kind of a hack, well, it's not. It works, is to use our backgrounds where we basically have a storyboard background. And this kind of, I mean, in the CRETA workflow, this kind of can be nice, actually, because you don't have to specifically create these new frames or anything. Because of the infinite canvas, this is just, well, you can just go in and do it. But this has problems. You want to rearrange them sometimes. So I have toyed with the idea of having multi-page support. But you don't really want to put it in MyPaint because there's only a really small subset of users that care about it. At least if you put it in MyPaint, it should be not in their face, than the other users face. But what I also part of my vision is to, if I managed to get MyPaint brush engine based on Gaggle, that just makes it much, much easier to reuse that code and all that stuff in other projects. So it should be pretty simple to just kind of create a new application that really reuses all the hard stuff. So that might happen eventually. But it's kind of really in disguise. Anyone else? Oh, thank you. Good job. Thank you.
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MyPaint is a fast and easy open-source graphics application for digital painters that lets you focus on the art instead of the program. Started in 2004 by Martin Renold to be a painting program he enjoyed to use and develop, MyPaint has grown to become a popular Libre Graphics tool. This talk will guide you through the past, present and future of MyPaint: Past A quick look at the history of MyPaint; the initial idea/motivation, and some of the significant events. PresentAn overview of the current status of MyPaint; what has happened in the last months and what is happening right now. A central part here will be about the MyPaint 1.0 release. Future Discussion about the future of MyPaint; some of the concrete plans that exist, and more abstract/undecided ideas and visions. Last but not least, how you can help the future of MyPaint will be covered. The talk will be introductionary in nature, and not especially technical. Curious digital artists, existing end-users, potential and existing contributors should all find this talk interesting.
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10.5446/21722 (DOI)
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Hi. Hi, everybody. I'm Mike from DeviantArt. Thanks for having us here. This is Gilles. He's a developer at DeviantArt. I'm kind of a project manager and work in Dizdev. And this is our first time here at the Libre conference. And it's been fun and enlightening. And it's gotten to me a lot of great people. And I think it's interesting. You guys have been talking a lot about the different projects and software that you're all working on. And you're talking about a lot of potential energy. And I think that sometimes you guys don't necessarily see the kinetic energy of the work that you're putting in. So I just wanted to start our presentation. I hope you guys can see the screen. But this is a little slideshow of artwork from DeviantArt. All of it was created with different open source software. But this is just a nice variation of stuff that was created with open tools. So hopefully you guys got to see lots of cool uses of the different open tools. And it's being used in so many interesting creative ways. And that's what DeviantArt is really all about, just exhibiting lots of interesting creative work. So I'm just curious, how many of you guys have DeviantArt accounts, how many people here? Maybe. Maybe, maybe not. And how many of you have heard of DeviantArt? OK, so it's a pretty familiar audience. So I just wanted to kind of fill you guys in a little bit about our official background, because different people know bits of information. So we've been around since 2000. So we're a little bit older than 10 years old. We've had the same management structure since the beginning. We don't have any venture capital finance or anything like that. We are profitable from operations. So we basically do things that we feel are right for the artist community. We interact with members of our site all the time. And we do things that we feel are appropriate. There isn't a monkey in our back trying to tell us you have to do this to be profitable. So we use those as our guiding principles for what we create. The site has over 17 million members now and 45 million monthly visitors from all over the world. That number grows by about 10,000 new members every day. We have over 200 million unique works of art. That's a number that grows by 100,000 works every day, which is kind of astounding. And while it's not as big as some other photo sharing sites, what's interesting to know about DeviantArt is that everything on our site is an intentional upload. Unlike a photo dumping site like Picasso or Flickr, people post their vacation photos. They post birthday party photos, stuff like that. Everything on DeviantArt was meant with a specific intention. Right now, we have around 2,400 different categories of artwork. So everything from 3D work to digital art to painting to sculpture, to pumpkin carving, to needlework, we really cover the whole gamut of creativity, except for music because that's the most litigious industry on the planet. So we try to stay out of that one. But in terms of our company, we have 75 people on staff. I know some people think we're a couple of guys in a garage. Some people think we're a huge corporation. But there's 75 of us. Our office is in Hollywood, California. Most of those people are actually developers or designers. So DeviantArt offers a lot of different services. And I think that we've been doing a lot of stuff with the open source community. But primarily, what we do is we offer free hosting for all of your artwork. You can upload unlimited images in any medium from any tool set. We allow people to just upload their stuff and post it for free. We also offer free professional online portfolios. Sometimes when you're presenting your work for professional usage, when you're applying for a job, or when you're applying to an art school, you don't necessarily want to have ads and lots of community features and communication in your artwork. So we allow free portfolios for people to present their work. We also have free web-based drawing tools, like Miro, which is our HTML5 drawing tool, something we developed over the last year that's gotten a lot of attention, which is very cool. And it's getting a lot of usage, which is fun. We also think it's important to let artists profit from their work. So one of the things that we do is we have a big shop where people sell their work. So essentially, if people upload a high res PNG or JPEG, we could sell it on a number of different substrates from coffee mugs and puzzles and calendars all the way up to really nice frame work, canvases or orangy clay. But the most important thing, I think, about DevenArt is that it's a really large, relevant audience of peers. If you upload work to Facebook or to Flickr, you're probably sharing your friends and people that you actually know in real life. But what's really interesting about DevenArt is that if you have a very specific interest, for instance, I really like pumpkin carving. I really can't think of any other places on the internet where I can interact with a community of people who are really into the art form of carving pumpkins. And I think that that's the best thing about DevenArt. You can find a community of like-minded people who are going to give you accurate, detailed critique on your work. And that is free and open. The other thing that is really unique about DevenArt is that the artist community really likes to share and collaborate. And we have a huge community of people who like to basically share resources and other stuff on our site. So if you browse around on DevenArt, we have hundreds of thousands of brushes, skins, tutorials. Actually, Adobe said that we have more tutorials on how to use Photoshop than they do, which is funny. And these have all been submitted for free by artists. And it's not just how to use the software. It's all sorts of really advanced techniques of how to draw eyes and shading, how to draw hair appropriately, and how to do modeling, how to draw animals, and how to model 3D figures. This is work created by artists, for artists, in order to inspire education and collaboration. We also have filters, plugins, stock work. I mean, you can just see different examples of models, other stuff here. This is something that we find really important on DevenArt. We think education is a huge part of the arts. So the next thing I want to talk about is kind of getting your artwork out there. DevenArt is a place where you're going to find lots of audience for your work. I think that's important. I'm not a very popular person on the site. But whenever I submit images, I get hundreds of views instantly. When you upload stuff to DevenArt, especially if you categorize it correctly, you get tons of audience for your work. There's also lots of ways to get your name out there by participating in contests. A lot of times we have sponsored contests. Different companies, movie studios, video games sites, they all want artists to kind of collaborate and participate. And they don't necessarily care what kind of tools you use, but they really like the idea of having people share and be creative. And finally, something we released last year, which is now growing popularity, is DevenArt groups. Do any of you guys belong to groups on DI? You're talking about it. So groups are really cool because they're like little micro communities of people who are interested in very specific things. So these are examples of some of our popular open source groups. You can see there are hundreds and hundreds of members in the GIMP and Inkscapeers group, the MyPaint group, open artists. So these are places where people aggregate to have conversations about using these tools. I think it's really cool just because not only are they sharing information about how to use the products, they're sharing tutorials, they're sharing examples of work that they've done in these tools. So it's a really great place for people to collaborate and communicate about using open source software. So the question is, how do we kind of get the word out there a little bit more about your tools? First off, one of the things that we find important is to add attributions to the different tools that people use within the Deviation Within the Artwork page. So if we can read it from the exit information in an image, we post everything on the side of the image. But I also wanted to kind of give you guys some more guidelines. You talk a lot about creating tools, and this is a very developer-centric community. But I wanted to talk a little more about guidelines for promoting your tools to the outside community, to artists who don't necessarily think in terms of programming. They really just think about how to use really cool tools. So it's important to build community around your tools. So I think for you guys as leaders in your community, I think it's important to go out there and promote yourselves. I think it's important to run groups, to participate in groups. I think it's important to engage people when they ask questions, participate. I know I've heard a lot of people talking about how they really like getting feedback from artists about how people are using their tools. And I think that DeviantArt is a great platform because people are learning about how to use these tools on our site. They're learning about the tools for the first time. And there's a great way to engage with the newbie artists. But also, don't forget, you can post news articles about updates to your software. You can run all sorts of little mini contests. I think if you inspire people to be creative, they will be creative. And don't leave it open-ended. Don't just say run an inkscape contest. Say run a car contest. You can say run, you know, it could be an imaginative car contest. Like, what kind of car would you like to drive? And then you're going to get hundreds and hundreds of submissions. Our most popular contests get like 10,000 submissions, which is crazy. And you don't even have to have big points, I think, as long as they're fun. People aren't motivated by prizes. They just like sharing and interacting. And they like seeing cool work. And lastly, post tutorials. And not just in how to use the software, like I mentioned. Brad gave such an awesome talk the other day about how he was creating his avatars. And I could tell you just from first-hand experience, artists love watching that stuff. They like seeing how other people create. And it inspires them. And they go off and create amazing work. I think I'm going to go try to create an avatar myself the same way. But as part of that, it's not just about posting a final artwork. I think it's important to also kind of share your projects. And that's one of the reasons that we're here today. We wanted to talk about a new project that we've been working on called Stache, which is an open submission API into DeviantArt. So basically, you can plug your programs and have a direct export right into our software using OAuth2. So basically, artists can instantly share and get their artwork out there to the world. Yeah, I'm going to talk a little bit more about this. So first of all, the URL is up there. You need to be logged into DeviantArt to access that. We're giving early access to everybody here to that new API. It's just been finished last week. And it's going to be public maybe in a few weeks or in a month. But everybody in this room, or if you're talking on RFC, two developers from the project that we're working on, can just log into DeviantArt or register if you don't have an account and go to that address. It will redirect you to the developer space that we just made, at least this new API. And also all the ones that people probably didn't know about. Like, for example, we publish RSS feeds of pretty much everything on the site. So we've always been open in letting artists get the data back from DeviantArt and move elsewhere. So for instance, you could query to get all the artwork from a specific person, from a specific type of artwork, and then you can just read it in the RSS reader or export it somewhere else. And this new API is about simplifying the way people can put their work online. So we've tried to make it as simple as possible for the developers as well. It's using OAuth2, which does most of the work, which is an open standard currently being worked on and used on many websites already. So if you integrate with us, you're also making your program ready to integrate with all the websites. So it should be pretty straightforward for most programmers to, yeah. Is it here? Yeah. OK, this sounds really interesting. OK. Can you open the developer's page? OK, this is really interesting to me. I was wondering about the final point combined source files with final renders. As far as I know right now, I cannot upload a native Cretafile to a decent art because it's not recognized file time. Will that be possible with this API so people can share the render feedback and make the.kr app great? So we want to make that like it's one of the core objectives of this API. Which is something that you had never seen on other websites is that we'll always tie the project file to the final render together if you want to. Like if your software has the ability to upload the project file alongside the final render, you can do that. And they'll always tie together. And something else that's really powerful with this API is that as soon as you submit the artwork, you get a unique ID that ties the artwork. They start the artwork forever so you can sync. So for example, you can make it so that when people modify their artwork on their computer and they save it, it's automatically published. It's updated on the UNAR. Like you always keep that synchronization between your workflow on your desktop and the online version that people can see and comment on. But yeah, we think it's really powerful just for the purposes of education to let people essentially share their project files with a final render. In some programs, the JPEG or PNG is the final render. But if you're working in GIMP, you get the.store your project file, which has all the layers and actions and history, which is the best educational tool that you could possibly ask for as a young artist along with the final image. And it's all in one piece of artwork so people don't have to start digging around in multiple places for that information. Hello. Good talk. I have a question about, so if you're doing such a thing where you're constantly updating your project and stuff like that, do you handle storing old revisions of the files or is it just at the current stuff? Not currently. It's very simple. It just replaces what's there. But ultimately, we could store the verging as well. It's just the beginning for us. We're trying to keep the API as simple as possible. And when the needs are expressed, we'll date it to that kind of feature. It's always possible. It's not in there yet. If all the programs or sites decided to use the same API, would you guys be amenable to allowing all the sites to use it? Say for instance, if you do go on some other site, look to your API and thought it was a good idea. And then programmers, say for Inkscape or GIMP, decided that it would be better for them to integrate with a standard API than it would be for a specific thing. Yeah. Well, the authentication is the big part of this. And it's OF2. So that's already standard. The API itself is just one HTTP form post. So you can't get more simple than that. It's already standard by itself. It's a standard HTTP post. We're not making something custom. Now obviously, if a standard emerges with other image hosting or video hosting websites that goes further than authentication, then of course we'll jump into a bandwagon and use whatever is standard. That's why we decided to use OF2. Because we don't want, if you look at the Flickr API, it's very custom, very different from all the rest. And we didn't want to go that way. Because we know that it's a very powerful week. In five minutes, you can write code that submits to the site. I've got a pearl example that's pretty short here. We're going to provide as many languages as possible as examples. So this is just what it takes in pearl to send an image to the UNART. So really not much code. And most of it is just the building a request and posting it, basically. Sorry, I get the question. I just had a quick question about your branding. I know as an art professional, there's a certain, and I don't mean this as derogatory, but like a stigma attached to TV and art about the type and quality of work that's going to be there. That it's usually like anime or this, this, this, whatever, downed dungeons and dragons, whatever. How do you guys look to compete with something like Behance, which is about more of the design-y professional side, and then something with Saatchi Online, which is more of like the art tour? And they both have aspects of social networking as well. They're just different than this. In terms of education, the statement you just made about the API makes my mouth water, because as an artist, like that versioning system, Ginger referenced it earlier. It's like you have final, and you have final, final, and then final, final two. Just to sort of consolidate that and have that as a tool is magnificent, and then also one with all the layers, too. So I want to say that from a technical standpoint, total respect, but how do you look to sort of increasing the usage of someone who's maybe 10 years into their career, and then as soon as you send that URL, it's like all of a sudden snaps to that. Is there like a, you talk about the pro? Yeah, I think that the tools that we have and the interfaces that we built for displaying artwork are significantly stronger than any other site. We're faster. I think that we display artwork in a better way that really puts the artwork front and center. And I think a lot of the other sites don't do a good of a job as we do. Now in terms of the community elements and the community makeup that you're discussing in terms of having younger artists, I mean, we clearly allow everybody to submit artwork. And we've actually tried to do a good job of rebalancing the content. I mean, the fact of the matter is that young artists have a lot of free time on their hands, and they're the ones that are submitting manga and anime, which is at the moment the most popular form of artwork in the world. It's just fact of the matter. So DeviantArt's showing representation of what's actually happening out there. But we're actually working on some cool new search technologies at the moment that will help personalize your experience. So DeviantArt in a year will actually probably look different than it does today in the sense that it will be more tailored to the experience of the person consuming content. Can't talk too much about that right now. But we're putting a lot of work into making content filtering much, much, much better. The goal being that as a viewer, when you go to DeviantArt, you only see artwork that you're interested in. So you don't have that problem of being subjected to seeing what's most popular across the whole world. You would see what you're into, basically. I can tell you that there are tons and tons and tons of professional artists on there. I have heard this saying that there's this art of snooping. It just is. There's this sort of thing like, oh, you're out there, DeviantArt. It's just a whole lot of work. Oh, it's a very long process for us to change, to try and change that image in some circles. It's not going to happen overnight that we're going to change everybody's mind about the preconceptions they have about the user base. I might have had that vision of it before I worked for DeviantArt. When you spend more time exploring what's in there, you find extremely talented people, professionals, like people who work for Disney, who post their personal stuff on there. So it's maybe a fact of people not being aware of that. So that's why we're going to try and change the way people explore the site to find it. There's a question in the back. Yeah, sort of. I was just wondering if you could speak on how like Jamas, it's like a reward system or like a bonus point system within DeviantArt. Jamas? Yeah, Jamas, L-L-A-M-A. Lamas. Yeah. Yeah, Lama. OK, sorry, I'm speaking in Spanish. Lamas. Yeah, so I was just wondering if you could speak on where that comes from. That was something we were testing. Lamas, that's just been part of our culture. In fact, I have some Lama stickers here and some plus they have stickers if you guys want to grab them. I think it's something we can't buy or see, right? Like way back in the day. I think it came from Winamp. Or Winamp, yeah. So it's just something that was part of our culture and kind of like give each other Lamas. So we were starting to build out our badge and reward system. It was kind of our first test to see how many Lamas people would give each other. It was millions and millions within the first between us. I've made a warm up of. I'm going to show you quickly the warm up of Lamas. Yeah, it was kind of ridiculous when it kind of, so I've made a heat map of people who've given Lamas since we've launched a feature. So you can see it's all over the world. Millions and millions. Yeah, you can see the. It's pretty cool. And it's just a fun feature for just outside people. There was no goal, no purpose when we built it other than making something fun. What's funny is little Lamas. In the middle of the mountains. Everywhere. Hi, just getting back to demographics for a second. I'm wondering if you have any idea what your gender ratio is on users and contributors. Particularly when we were talking about preconceptions and changing that about the, changing people's preconceptions about DeviantArt, the slideshow at the beginning had about 90% elven women and like cyber tits. So I was wondering like, if that's something that we're looking at changing. You know. Well, changing your audience is hard. But I could tell you from, I've looked at the data just to see the numbers. And I think we're, we have slightly more males. When I say that, I think we're at like 52% males. But it's actually a pretty balanced group. It's like 52% males, 40 something percent women. And then we also have the small group that chooses not to define themselves. So let's see. So I have a quick question. Sorry, was there somebody else who wanted to ask a question? OK, I grabbed the mic. It's me. So I'm an academic. And actually, I'm thankful for DeviantArt because the first piece of graphic software I wrote was put on by a DeviantArt person without asking my permission for which I'm eternally grateful. And you put it through DeviantArt. And then it's kind of popular anyway. But being an academic, I'm wondering if you'd consider having an alternate brand. This is a bit like renamed a Gimp thing. If I put in my CV that I have some art or software on DeviantArt, the chair of my promotion committee, who, for example, jumped out of his chair when I used the word hacker to describe myself, you know, will jump out of his chair again. So could you have some sort of, it's a portal to DeviantArt, which is not called DeviantArt. Something like, for stupid promotion chairs. We have to inform the portfolio. Something kind of like that. With the portfolios in DeviantArt, you can have it on your own domain. It doesn't show any DeviantArt branding anywhere. Sure, but it's kind of nice when you can link something that's public, not your own private thing, because it's kind of more published. So it would be just a safe name portal, which actually sends you exactly to the same place, which is you. But it doesn't contain DeviantWords. So that's one of our bigger challenges that we're trying to take on in terms of marketing and branding. The way that we use Deviant, the word Deviant, is from a Frank Zappicoit about deviating from the norm. And that's the way that DeviantArt was branded, and being different, and being a place where people can share freely, and it was a safe place to explore ideas. Some people think of Deviant as a different kind of word. So the more PR that we do for the community, the more PR that we do for the site, we are one of the 100 most visited sites on the internet. Not everybody knows about us, but we are very popular. So the more branding we do in mainstream publications, the stigma will kind of go away. So I'd say brand would go farther with parent-teacher associations. Right. No, that's a valid point. If you have a brand, which of course is exactly the same. It's something that's come up a lot. Why be such a prudent politically correct? It's probably that. Well, good. Yeah, it's a bit harder to stem yourself from the differences. So about this, this is a way to submit us. And the way that traditionally you've been able to get art and search for art has been through the RSS feeds. And no, we have OMBED as well, if you want to show the arts using our bandwidth. I see. Because traditionally, I've used the RSS feeds in order to create programs that could actually get art from Deviant R. I created a wallpaper thing that could randomly pick a wallpaper out every day. But the RSS feed is actually quite difficult to use with the search field. You actually have to create search fields and push them in. And it's not exactly programmatic. It's just push. It's mostly that we haven't documented it before. And we are going to start making the RSS page. It doesn't have all the details yet. We will publish all the, like yesterday, there was Mark from Open Game Art who asked me about searching for creative comments content on UNR. And we have an option for that. But the RSS page has never been documented before. So that's the kind of thing we're going to put on that page. I'm going to go to the guy who knows, and I'm going to write it all down, basically. Do we have time for a quick demo? I mean, we could show you guys how Stashworks, GIL, just as a demonstration of the technology, wrote a Mac OS X and an iPhoto export. I guess the easiest one to show off is the OS X upload, right? Either one. What is it? I'm sure not. Go for it. So, yeah, uploads and fellas. 9. 9. 9. 9. 9. 9. Did we lose our internet access? Oh, yeah, maybe you got kicked out of the. Oh, yeah. Yeah. Oh, good internet access. Well, anyway, let's pretend this worked. And as soon as it's uploaded, it's already online. So we've made it very easy for people to share it immediately. And then if you want it to be indexed afterwards on the search engine, then you provide more information like title and description. Right. So the idea is that as soon as it's uploaded, it's instantly shareable. It's here in the stash, and you get a favme link immediately. You don't actually have to submit it to DeviantArt if you just want to share it with your friends. It's instantly public on the internet. You just copy that link, send it off. And it's in this temporary space where you guys have tons of storage for your artwork. And then once you go in, and actually, I mean, you can see here there's a little bit of attribution as to where it's coming from. This came from the OS X uploader. This came from iPhoto. So if I wanted to go in and publish Pumpkin of Darkness, it would come up with inline editing options, title. I could add create comments, licensing, all that stuff, save changes, and boom, it's in the index. It's now published to DeviantArt. It goes out to people's message centers. All right. So I see there are more questions. Just come see us. We don't want to hold the stage for too long. Thank you. Thanks, guys. Thank you.
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In the 10 years since it’s inception, deviantART has become the home for over 17 Million Artists with an audience of over 45 million people all around the globe. The site provides an exhibition environment, community tools and resources for artists at all skill levels, in all mediums. As a supporter of the open-source software movement, deviantART hosts millions of creative works, tutorials, assets, brush packs, skins and resources for all of the major projects. The Groups platform also creates environments for people to collaborate around software projects to share and curate their favorite artwork and resources. Gilles and Mike from deviantART are here today to discuss new opportunities for interfacing directly with this massive online platform. Mike Halpert works with the business development and product groups at deviantART. His work includes numerous popular products such as Portfolio, the dA Mobile site and numerous e-commerce offerings. Prior to deviantART, Mike worked in creative development at Lawrence Bender Productions and the prestigious William Morris Agency. Halpert is a graduate of the Tisch School of the Arts at New York University. Gilles Dubuc is one of the team leads of the Devious Technology department at deviantART. Since joining deviantART, he has worked on core products such as the groups platform and notes, has rewritten large components of the website and pioneered innovative optimization techniques. Prior to deviantART, Gilles worked for several companies including SMS Central Pty Ltd and Sun Microsystems. He also founded two startups. He graduated from Napier University in Edinburgh, Scotland.
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10.5446/21657 (DOI)
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So thank you for showing up. I believe this is morning. Actually, I was kind of rushed in the morning. This morning I paid for a latte downstairs with extra double shots. And every time I tell them, you need to use the large cups otherwise it overflows. And now they know I've been here for days. And I wasn't such a rush that they still have my, they forgot to turn on the machines. The machine was cold, so I still not had coffee, oh my god. Anyway, so I hope to contribute, I'm an academic, so I hope to contribute things to posterity. I think my most likely contribution is a saying which is the early bird gets to wait. So I think you're an example of this today. I also found out this morning showing up at 7 a.m. that the early bird gets to climb a lot of stairs because they don't turn on the elevator. So, and I found out once I logged in that my graduate students had fallen asleep while putting together the slides. So we'll see how this talk goes. I apparently woke him up. Oh well, anyway, that will teach you, weaned himself off coffee three weeks ago. And there should be something written in the graduate studies to encounter it. Anyway, so this is an academic project about imagery sizing and resampling. I'm the guy at the top. As you might see, I have, I'll try to remember this turning business, ha ha, see? And now I understand everything. I have two master students working on this as well as various collaborators. Actually, there's more collaborators than this. For example, Pippin at some point lent a very important helping hand. There's been some talk about how to get programming, good quality programming done for open source projects. I just want to make a suggestion. Is that if you know a graduate student or actually an undergraduate student who seems promising or even someone who's been in the industry and wants to take a break somewhere where there's a lot of snow for a long time. So actually I can snow shoe from my home to where I work. These little lines here are cross country trails in the winter. This is golf in the summer. This white spot is a beach. There's a small ski hill off screen as well as a Best Buy and a Toys R Us. And a downtown with an excellent French and English music scene. This is a little French island in Northern Ontario. The Dion Quints, right? They were Northern Ontario francophones. Do you know who they are? No, you're too young. Yes, maybe. They were the first famous blah, blah, blah plaits. They were Quintuplets who came from, they were basically born in a shed. Anyway, so maybe what you could do is, this is a bit different than actually paying someone to program. You could set up some sort of scholarship for a master's students to work on what he or she wants to do. But if they take their money, this is hopefully something you also want done. And then profs are generally good at leveraging, right? So we'll add more money. And this masters of computational science is actually set up so we can take people from various backgrounds. The main requirement being you must be able to program. Okay, but if you've not done much college math, you'll suffer in some courses in first year, pardon me, but you should be able to program on the project of your love for at least one of the two years it takes to complete these things. One of my students completing this in 18 months, but she's very bright and hardworking and organized. Anyway, so this is not the worst place to spend two years if you don't mind good winter boots. Okay, so this is a resampling talk, as I mentioned. It was somebody whose favorite contribution to humankind is the early bird gets to wait. It's probably somebody who does things at the last minute, hello. So let's see how this talk goes. So first of all, maybe I'm hoping all of you know what resampling is, but just in case resampling is any operation where basically you change the geometry of the image somehow. This is a bit of a reductive definition, but it works, so enlarging, shrinking and image making thumbnails, warping, applying perspective, rotating. This is all resampling or the basic underlying operation is resampling. So I'm gonna talk about a few novel resamplers, and as you can see, there's gonna be titles that have to do with the various groups of collaborators where the main people involved in every project. So Anthony Thyssen is one of the main developers of Image Magic, which of course, the main developer is Christie, also known as John Christie. And anyway, Frederick Winehouse hangs a lot on the Image Magic forums. Okay, so basically this new method called jink, this is not a misspelling, there's a sync function which is constructed using the sign, to the trigonometric sign function, it's sign x over x. And the jink function is the 2D equivalent. So a lot of classical samplers or resamplers that you guys use, they're built from, basically it comes out of audio signal processing, but audio signals are one dimensional, they're time, it's an amplitude and time. And one of the points I want to make is that you're not getting the best bang out of the buck, if you use a tensor method, meaning, if you use a one dimensional method twice to do something two dimensional, you're missing something somehow. Does it, okay? So one of the things I do is I build fully two dimensional schemes and for resampling. And of course I take inspiration from elsewhere. In this particular case, the inspiration is Paul Eckbert, who wrote the original Zoom program as a graduate student in 1986, I believe, which is the basis for Image Magic. So he's created it as an author, even though I think he's contributed very little code directly, but in a sense he's contributed everything. Anyway, so the point I'm gonna make in this part of the talk is that you can do, you can look at resampling as saying, no, no, it's texture mapping, or do it as if it was texture mapping. So when you're doing texture mapping, the Eckbert way, which is quite common, really what you have is when you want to know the value near a location on your output image, you're gonna do this by averaging in some sense some sort of reconstruction, this is conceptual, but it's not quite accurate, but it's okay, in a circle centered at the location of interest. Okay, so the values you're gonna average, they're obtained by pulling back that little circle back to where your data comes from. When you're doing texture mapping, here it's a perspective transformation. What you're doing is you're applying the inverse of the transformation, you're pulling back, you want to know where these values come from, this is going in, so you pull back these little circles back to the original image that you are applying perspective to, and it turns out that with perspective and affine transformations and linear transformations, circles and actually all ellipses are mapped to ellipses and since the inverse of perspective is a perspective, you get this when you pull back, so now you have these ellipses that sit on your input image and some of them are small, which means that an interpolatory scheme like bicubic or bionic even might work okay, and some of them are big and they are also not circles, some of them, they might enlarge things barely, for example, the right ellipse is barely wider than the little circle, so you don't grab too many pixels in direction, but it's very long, so you grab a lot of them in the other direction, and a lot of the work that I do with these students has to do with fixing schemes using information about the lengths of the minor and major axes, the width and the length of these ellipses. Okay, so I think one way of describing what a method does is to show results, so here's the test, I have a tiny image, this is the public image magic, it's the rose picture, and we're gonna enlarge it 20 times, so this is the new method, this is the enlargement with the new method, and I'm saying it's better than Lancho, so in a sense what it is, it's an improved Lancho, it's a high quality Lancho, so here's Lancho, this is standard Lancho, got it computed carefully with image magic using HDRI mode, so let me show you again, now you can see the image magic command at the top, you need to have a fairly recent image magic for this to work, so now you can resize two different ways in image magic without having to program things very, you can do things lots of ways in image magic, but there's two easy ways, there's the resize way which has been there for 20 some years, and there's the distort resize way which uses elliptical weighted averaging, but actually a modified version from what Egbert and other people considered, so now I'm gonna give just a tiny anecdote, it's that Egbert original elliptical weighted averaging which is a popular splatting method, he called it HQ, it's HQ, EWA, EWA is elliptical weighted averaging, and people liked it a lot because it was an high quality method, and of course now there's textbooks that appear that say but actually HQ, EWA is not that high quality unless you're dealing with distant horizons, and I find it kind of humorous that my first contribution to graphics open source came from code that was taken by somebody on DeviantArt named Photocomix, there was a discussion on the game side where he told me, no, what you do, we'll never work with the new thing which is Giggle, and I said, okay fine, I'll do something else, and then somebody grabbed this from my website, and then liked it, and then repackaged it, and then called it because I had given acronyms like E, A, and B, Q, H, he felt this would not market things too much, it's like calling something DeviantArt, if you call it high quality, clean cut PG art, then the PTA won't get mad at you and will send all its kids to your supply, just make sure there's no cyber breasts or what somebody mentioned, right? Okay, and anyway, so then he called it HQ Upsize or something like this, and then it became popular because it was high quality, so anyway. So basically what this method is, it's taking various ingredients from various smart people, and then getting it to fit together just right. There's one tiny new idea in there, but really it's a thing, there's all these pieces, but nobody has put them just right, we put them just right. Anyway, so one of them has to do with doing, doing clamping of the ellipses the right way because you don't want your ellipses to be smaller than these little discs you have at the beginning. Okay, so how do you make sure of this? EggBird has a quick and dirty way which led to incredible bad blur when you were enlarging, for example, so we fixed that and we fixed a few other things, and we also have a way of computing this extremely fast, without using trigonometric functions. So we do trigonometry without trigonometry. Okay, so what can I show you about this? I think you're able to see that the jaggies are much reduced, that it's slightly more blurry, right? Maybe not, it's kind of hard to tell, doesn't make sense, right? And the halo is also reduced. Look at the bottom, there's less halo. The reduced halo is partly because the jink function decays faster than the sink function. Anyway, so in my opinion, this is a killer scheme. Okay, right, just to compare, this is the default resize in image magic, it's a popular method, it's the bicubic Mitchell, Mitchell-Nitrovalley, no, I'm not there yet. Okay, so this is a very popular method, it's the Mitchell, which is a good compromise, Mitchell-Nitrovalley, anyway, and whoops. So notice, there's no question, our method's better. And you know, I'm sorry, I'm biased, but I'm right. Okay, so, okay, so you're gonna, I'm not gonna cover all the topics that I put on my incredibly ambitious 20 minute talk, the apologies. Anyway, so this is the, what's the basis of the Bessel-Jing, but it's a windowed method. The basis of the windowed method is a basis function. So this is using the sink, the 1D sink in a tensor orthogonal way. Notice these ripples, this is the checkerboard mode, right? It's these alternating up and down things that follow the square pattern of the grid. So this is why you get these jaggies. Now, and you can also notice that it's a low pass filter, but actually it's not as good a low pass filter because the corners of the frequency response are clipped with the Bessel one, does that make sense? And notice, I don't know, you show this to your grandma, who's of course an open source freak. Anyway, and you say, which one do you think will work better? No contest. Okay, and it also works beautifully for down sampling, and it also works great for warping, and it should not take too long to get Vips and Gaggle implementations. Those in the room involved with this group know the meaning of soon when I write it. Still waiting for sabbatical. Okay, or unemployment. And so I can get some serious programming done. So what's the weakness? The weakness compared to classical langios is it's not an interpolatory method. What that means basically is that even if you're doing something, even if you take your image and you happen to decide to resize to exactly the same size at exactly the same alignment, you will not get the original image. It will low pass it a little bit. That doesn't make sense? It's not major, but... So if this bothers you, I know how to fix this. This is with using a later part of this talk. Basically what you do is you take the standard langios and then you blend it with the new one, okay, in such a way that when you are close to doing the no op operation, then the old langios, which is interpolatory, but has more artifacts, dominates the computation, right? That doesn't make sense? Okay, so... So now the next topic of my talk. I'm at 10 minutes yet. Yeah? 11. 11, oh my God. Okay, so I hope I put these slides right. Yes, I did. Okay, I'll deserve that latte, which is waiting for me. Okay, so this is another scheme. This is not an EWA method. This is not an ECO, weighted averaging method. This is an interpolatory method. So basically what it does is it reconstructs the surface. This is not good for making thumbnails. It's only good for rotating and large-ing or maybe reducing just a little bit. Does that make sense? So it's a completely different. It's also a nonlinear scheme. The previous methods I showed you were all of them. Linear methods, meaning what you get, if you resample, if you enlarge two images and then you average them, you get the same thing as if you average two images and then you enlarge it. That's a linear scheme, more or less. Does that make sense? This is a nonlinear method. There is a slope millimeter built in there. The slope limiter is called min-mod. But the thing that's special about this one is that it's both sharp and halo-free. Okay? Actually, there's a bit of a lie. There's a possibility, a tiny, minute amount of halo, but you cannot never stick out of the local values. Of course, Bailinear and nearest neighbor do this, but they're incredibly either blurry or jaggy or does that make sense? And B-spline smoothing, quadratic spline smoothing, Gautchen blur also, as no halo, but it's very blurry. So what it is, is this nonlinear guy manages to balance blurriness with halo-free-ness. Does that make sense? Okay, so unless you care about being halo-free, this is not for you. And as I mentioned, it's only good for up or rotating or sane. Okay, so I took the simplest, nonawful halo-free method. It's Bailinear, and I'm doing the exact test as before. So of course, Bailinear is both blurry and jaggy, right? You actually get these ridges. Bailinear is the most annoying method ever, but it's great. But it's annoying. Okay, so this is the new one. Okay, by the way, these methods are in the poster that's out there. Okay, so I don't know if you can kind of tell. Also, our eyes create halo themselves when we look at high contrast lines, right? The frequency response of our brains is nonlinear, our eyes is nonlinear. But it's pretty sharp, okay? And it's basically halo-free. Yes, it's jaggy a little bit, doesn't make sense? Okay, so this is the best I could come up with. Took me three years, okay? So, but it runs pretty fast. It, once your library is set up so that there's not too much waste, this, I'm saying this from memory, this is about three times slower than a standard BIQ-BIC. And it doesn't take much data. The stencil's quite small. So five by five take away the four corners, right? And a BIQ-BIC is a four by four. So this can run really fast. Both, it depends what you call fast. Oh well. And it's already in Vips and Nip too. Now I come to Jacobian Adaptivity. So what you have is you have a favorite method for enlarging and rotating and doing things that are up sampling, right? And then you have a favorite method for down sampling. It could even be gosh and blur, right? Making images smaller. Taking lots of pixels and having one representative speak to the pixel. So given that many methods are not jack of all trades, okay? Ewa, jink, ewa, lancetose is a pretty good jack of all trades but it's halo-y a little bit, right? And it's a bit blurry. And then no halo that I just showed you is just good for up and same but not down, right? So you pick your favorite of one or the other and then you go, okay, so how do I get a jack of all trades sampler that does all this? So the obvious answer, and if one of you knows references where it's been done, I'd look, is you blend them. And you blend them using measures of what the transformation you do at that point. Of course, if you're doing warping, right? You can approximate locally the transformation you're doing, you're warped by an affine transformation which of course could be trivial, right? If it's a stretch in all direction, the linear approximation of this is stay there. Does that make sense? Right, so there may be what they call degeneracy. Anyway, but one way or another, it's not too easy to tell everyone who implements a geometric operation, you need to return a reasonable approximation, a reasonable affine, right? It's a translation plus linear approximation of the transformation at every point. Does that make sense? If you have a formula for this, you can do it by computing the Jacobian matrix. Okay, so then what you do is these give you these ellipses so then you can compute the lengths of these two axes and then what you can do is this, is you can say the scheme that's good for down, the scheme that's good for up, okay? Use it in an amount proportional to, I'm using the reverse transformation, right? To the product of these singular values of these axis lengths and then give the rest of the contribution to the other scheme. Does that make sense? If you do it right when you go up, you're gonna only use the good up sampling scheme and then as you move away from going up or rotating, slowly you're gonna increase the strength of the down sampling scheme and there's good reasons to use these formulas that I just described extremely tersely and probably wrong. Okay, so once again the basis is treating everything like a texture mapping, okay? And these are the slides that I downloaded at four to nine. Okay, so actually I need glasses otherwise I don't know what do you do? So this is LBB No ALO, that's the good up sampling scheme. This is elliptical weighted averaging triangle. It's using a tent, it's using a cone, right? Bionic air is this, so do a 2D version of bionic air, you get a cone, right? So that gives you a filter which is a very bad approximation of caution. Ah, okay, okay. And so this is the result of enlarging. So it turns out that this scheme sucks at enlarging so you fix things so that theta is one so this is not used at all so these two images are the same, does that make sense? And you can do this on a pixel by pixel basis even though here the decomium's constant so theta's constant. Now if you reduce, I told you no ALO is not very good. So this image here is very close, the result is very close to this one. This was done with something which is currently in the sampler's git branch of Gaggle, it's called low ALO, okay? And rotation, but then a rotation takes a circle and just turn it like this so it's like an up scheme. Does that make sense? So once again, theta is equal to one and this image is exactly the result of that nonlinear halo free method and what you could do is you squish, right? So then you're gonna, this image is fairly close to this but not as much as if I had squished equally in both directions, does that make sense? So you can take any two schemes and then you have a formula, you could compute theta and then you just plug, okay, give me this much of the good for up, this one of the good for down the end. Okay. Okay, how many? Okay, so I'm gonna be very, very fast. Okay, so I have two. So as it turns out, some of you program resampling methods in this, I am stunned at the lack of publicly available optimized code for doing various things as simple as doing bilinear. So I'm not gonna show it, but if you have a bilinear sampler, be it an integer arithmetic or in float arithmetic, actually, and my collaborator John Cuppit, who's a fantastic programmer and benchmarker, will attest to this, you can almost certainly do better than using lookup tables by using optimized code, okay? So email me, maybe next time I come, I'll actually show you formulas. I have this for bilinear, I have this for all the bycubics, I have this for language shows, the kernel, involves tricks, so I can replace those by polynomials computed with the boost C++ Minimax library, which I doctored so I can do relative error instead of absolute error. The Bessel functions are a royal pain in the next compute, I can replace them with highly accurate polynomials, you like 10 flops, 10 power minus five from zero to three, you get the idea, okay? And so these are works in progress, but if you want speed and you, some of them, they're just like filters like black men and all this, they are always given in standard form, but actually you can remove half the tricks by just using trigonometric identities, does that make sense? So I'm talking about this kind of stuff. There's these simple formulas that people have not sat down and go, how can I do this fast? And so that's pretty much it. And if you have questions, I have a Gmail account. Thank you for this quick end. No, nice talk, nice talk. Any questions? Yeah. Actually, I don't need to do this, right? I can show you beautiful Sudbury, Ontario, where I was still grading final exams Tuesday. So what's your question? So it's wonderful to see this in ImageMagic. I wonder if you see whether or not this might be applicable in a lot of other type of things. Like for example, how far away do you think it is from being ported to something like say, Blender or something like that for if you want to take a look at, I guess, either in just the compositor is resizing or something like the actual scaling of textures as they're interpolated and stuff. But 3D is a bit more programming work, right? So Pippin will attest that when I see soon, I mean three years. OK? This being said, things move faster. So if there's interest, these are perfect for demand-driven systems. Does that make sense? You know, right? It's not like ImageMagic, which is a data-driven. It's demand-driven. So N2D should not be much harder, but I have a few articles and stuff to publish first. So I'd say I could get started on this probably next summer. But if I get either an interested grad student or a prodded a lot by a high-profile product like Blender, it may happen faster, but don't hold your breath. Did I answer your question? Of course, I want to go to 3D. So Adam Turcott is not on RSC right now. Can you speak a bit more slowly? Adam is not on RSC right now, so I cannot ask him. But is there any reason I should not merge this Hamplers branch into master yet? But we want to clean it up a bit. We want to remove stuff, actually. And also, I need to ask you personally about we fix the Jacobian matrix stuff in our branch, and then somebody else fixed it differently in master. So I need to ask you, can we use our way? OK, so the answer is basically soon, but let us do a little bit of ironing. How about that? Yeah, and just kind of another little comment as well, is that in ImageMagic, there is already probably too large forest of available resamplers. But at least thank you for having moved away from the idea that you need parameters for the resamplers. In addition to choosing the resamplers. Well, now I choose the parameters for you. Well, that is saying the false, and that's better than asking the user, how do you want to tweak foo alpha and bar? Yes, you're totally allowed to send me your monthly reminder of what you don't like. I'll definitely take into account. I want to mention something, however, is that ImageMagic is a very important tool for the resamplers. ImageMagic has a forest of craziness, but there's defaults. Although I have mixed feelings about this, because I protested this choice, one of the defaults is a method I designed, which it's named a goby do, but you don't see it when you use it, because it's the default. Does that make sense? So a forest, you can have one tree out of it if you want. Is there a place where I can just read about this in my own speed, because this went a bit too fast for me, but I want better image scaling for Krita as well? Unfortunately, this is a very sad thing, but I code faster and I write articles. There was a lot of discussion in the ImageMagic forums, so you can find me, Nicolae Robidou. I don't use aliases like MartianX. So you can find and then out of there, you'll see that you can also email me. And if I get requests, I tend to put together summaries for people who contact me faster than I write articles for publication. And then I can say, OK, what do you need? What's good for you? I have a fairly big picture of the whole forest of ImageMagic methods and more. Does that make sense? So you can kind of tell me, but we like these artifacts. We don't like these artifacts. And then I can, but I think this will work for you. I think this won't work for you. There's another thing I want to mention before I get shut off. It's that I'm actually doing a lot of consulting these days having to do with making thumbnails and compressing them for the web. So if some of you have expertise in this, I would love you to snatch me and say, you should do this like this, or you should not do this like that, or whatever. Does that make sense? Actually, I fund grad students by consulting work, which of course, you need to take off the tape. Because if the administrators find out, I'll get in trouble. OK, so OK. Thank you. You're welcome. Thank you.
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Regular talk in the form of a series of linked lightning talks. We would of course like some time for questions. Could eat up a one hour block with 5 min Q&A after each 5 min talk? (This would mesh better with RiverTV than having all the questions at the end? We’d love feedback and discussion: Much of this is work in progress. * Jinc-windowed Jinc clamped Elliptical Weighted Averaging: A superior alternative to Lanczos Sinc-windowed Sinc filtering Several improvements to Heckbert’s EWA method have produced a filter with the desirable features of the classical Lanczos filters. The method, suitable for demand-driven systems (GEGL, VIPS…) will be described, its strenghts and weaknesses stated, and comparative results involving image enlargement and reduction, computed with the ImageMagick implementation, will be shown. * High quality automated JPEG thumbnail and reduced image production with adaptive prefiltering JPEG is still the format of choice for the electronic transmission of small and full size versions of natural images. At low quality levels, however, its block and ringing artifacts reduce its edge over JPEG2000 and dithered PNG8. These artifacts can be reduced by increasing the strength the lowpass filter used to reduce the size of the image. ImageMagick examples, illustrating these and other ways of maximizing bang for the buck, will be discussed. * Nohalo subdivision with Locally Bounded Bicubic finish: A halo free upsampling method LBB-Nohalo is a novel halo-free resampling method which can be roughtly described as an adaptive blend of Hermite and Catmull-Rom interpolation. The method, suitable for demand-driven systems, will be described, its strenghts and weaknesses stated, and comparative results involving image enlargement, computed with the VIPS implementation, will be shown. * Jacobian adaptivity: How to smoothly blend a resampling method tuned for upsampling with one tuned for downsampling Suppose that you have a favorite sampler tuned for upsampling, and a favorite sampler tuned for downsampling. How do you “”blend”” them so that the “”right”” one is used, yet without “”switching”” artifacts when warping goes from up- to downsampling within an image (as can happen when performing a perspective transformation) or in different directions at a single point (like when resizing by making the width smaller but the hight larger)? Answer: Blend depending to the singular values of the Jacobian of the transformation at the point under consideration. Details will be provided, and GEGL results hopefully shown (still coding! the machinery is built into GEGL but no high quality sampler currently uses it). * The hacker’s guide to the computation of common resampling filters and related geometrical quantities Several simple but little known formulaic simplifications for common filters (bilinear, Catmull-Rom, Blackman, …) leading to speedups will be presented. Most have already been implemented in ImageMagick and VIPS. In some cases, calling them directly is faster (and more accurate) than using Look Up Tables. Another example of simplification: Highly efficient trig.-free computation of the smallest ellipse containing both the image of a disk by an linear tranformation and the disk itself, and computation of the containing parallelogram with horizontal top and bottom sides. * Highly accurate polynomial approximation of windowed-Sinc and windowed-Jinc filter kernels The Boost C++ minimax package can be used to produce fast and highly accurate polynomial approximations of non-polynomial filter kernels. Examples involving both the Sine and Bessel versions of Lanczos 2 and Lanczos 3 will be given. Similar approximations are used by ImageMagick.
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10.5446/21658 (DOI)
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Today I want to talk about how to connect the integration state of the device to the device settings to the actual power. I think this has already covered some of the use cases by comparing different native code behavior with different devices, monitor, split-ups, etc. And so, in typical use case, we can often hear as, so it's a binary of the internet, we get a Z-class on the screen and want to do the stuff which has disappeared, and we get the blocks that run, open them, and see if we have different inputs inside because it's in a different color. This is a typical disconnect of conventional and something to avoid, and it has also an economic impact. And the other example is the arts like imaging. You create, you're all created, most creators of arts, and you cannot be sure what is the audience, the user world, the atom, and how it works. For instance, open source wallpapers are typical in green, and on some of the photos, they appear a little bit over-separated, yellowish, and on others, we look green as we expect and on some, we brownish, which is completely off what was in Canada, so. So, with current trends, it's why we try to think these things and get them result, which is comparable and we need a color correction of all these different inputs and different inputs coming out of each device. The goal of connecting device calibrations to ASCII profiles is to make things more automatic so that you can handle things, contribute very much machine-readable data for machine-readable data, so you can handle this like a variable database. And we also have to go to make this data very flexible and, in the same way, robust for the user. So, the final target is to have very easy color management for average users, which have no idea what color management really means, and in the same way, to increase the robustness for professional users, which, by the way, of situations where they are not sure if they have some correct calibration for the actual selected ASCII profile. Systems which include this kind of automatic and flexible resilience can do many things while we are only without interacting much more with anyone as the user and the way it is today needed. I have to just select an example of how we can print as the interface. There are two front-ends for which we print once, coming in campaigns, which is also available in GIMP and Z-WATER application. It is called a print. Both shared with the interface, you can do six inputs of input resolution. Both can do color management with Z-YK and RGD. And this is pretty all of the work we share. Then they do very different skin paints, with an older approach to attempt to do color management with Google print, and it just relies on the print's Q name. It's not much for specific C-S-S. So on the other side, the public print uses presets. These presets include our, so it's a driver state. You have changed the CR or the brightness setting, and this is already covered in these presets. And you have, of course, identification for what you don't mix things up with the print. So the colors, which are kind of from the apps and things are on the HP, of course, make them size. And in KeyBank, again, so the profile selection is manual. You must know a specific color for the print queue, which kind of profile you need. And in full print, on the other side, you have already some logic to piece these things together. And so to fit these pieces together, and the profile is strongly connected to all of these color variations so that you can still go on so easily. And finally, it's calibration and to the proper association is non-existent in the scene print. And this makes it very error-power. You can even change settings in the file and printing user interface, which are color related. And this don't affect any way to the ISOC profile for X-Mesh. So if you do a soft-filling like a small thing, you use all of the basic, which is the calibration basic, which the profile needs to have as a foundation for its final color. And on the full print, it's much more of this kind of fancy. And now we want to go into the key to this means how to get these pieces together. In the full print application, we have just implemented the printing in a very specific manner. We want to scale and flexibly apply to printing, scanning, other input-to-visile cameras, and also to the output to this place, mainly in other projects. And these devices have now natively, normally, no information which of the options are color related. For printing, it's pretty low that you have positioning and sizes of paper, which are clearly not color related. And other options, which are clearly color related like brightness, gamma resolution, and so on, are written for visual. And these later ones must be marked as such. And in order that the system can understand that it's important to keep constant focus with the profile association. We must propose to introduce this more into the QBD. So print description file. And I think we can print as we start to put it in one of our lists. And so it will be the front-end profile association which will be able to correlate the device calibration with the actual profile association without interfering too much with non-related things like OS, animation, positioning, or media stuff. And then we will propose relatively unlikely that it will be applied because of compatibility reasons. Then we will be able to decide to have a very stable physical interface and API. And then incorporate these changed mods already there, but quickly apply the distributions in handy for XO, XTN, library to extract calibration from the edit information. There surely could be more information involved like calibration curves which are possible to put into the monitor itself or brightness settings. There's still a lot to do for camera raw and XF data whereas no such links could be proposed. This would have to be worked out in close connection to the standards. These all these settings should now be made accessible in machine being the way to be exported and be used in other contexts which are far away from native data structures also according to others. So we would like to explore this in our autism and I hope we can find the common format to suggest this stuff with a bit of an update. On the other side we have the ASCII profile, ASCII meter attack which is a pretty generic data structure based on P and value here which can be placed into the ASCII profile, you can mention all the state functions, stabilised phones and devices, calibration data can also be put into the ASCII profile so that we get a pretty compact data where all information is saved. We have just sketched how all these things can work together from the convention inside. This is a calibration at the tribal input which means they realise the data and get some kind of measurement information and we need to preserve this meter and some way and later during the profiling stage this is the stage where it is properly able to apply this calibration data to the ASCII profile and to get finally ASCII profile which contains many information about the device and its calibration still. So we have a pretty compact set of information to continue to work. Something I've learned already in the last 12 years, maybe it's even in the 5th. The last is to easily share ASCII profiles or sentiments or distributions, just put it in place and finally the users can search for these profiles as long as we are in the self-contained, all information which are needed to set up the colour settings for the device and also to identify the device already contained in the ASCII profile. We don't need any special routine to manipulate many parts. Systems can be constructed to do by the self just from the information which is in the ASCII profile. So it's not the case as an outline on the ASCII page, for example. Things have to do, have to be done in a manual way. We hope that this is the way we get more response to these things. If you have a profile selected for your device, you can also make user interfaces in a way that the list of profiles have on top the most matching profile. This can also be the first one which gets automatically applied to the user in the user and the profiles are there in many cases. But it should of course be there for the user to have a chance to see these things. Also it's possible to resolve in a local and notepad the sizes in profiles just like any database request. So it's just an machine how to put profiles into the user database and to have very different kind of data to ensure all work is in the order. Now through the project I'm working on, we have implemented stuff like this for XOR and to come with a lot of profiles selection. Our audience is probably going to see code, we have to solve it not to be our live computer as a statement, we have to get to someone doing a code project and make these stuff accessible for users to interface with or see. In contrast to my phone speaker, the audience is not required to meet new clients, it's a pretty much user thing. We think that we will not build back when XOR develops to the site, we don't want with XS that we now introduce this requirement for our users. So our awareness is also very much modular and flexible solution. We don't need any special things other than to manage the tagging of the last configuration information to use. We don't need much involvement in the other guys' systems. So it's just an open field, architecture, we have tagging systems for different guys' systems. We also have to plug in our backends, for example we have the OZ process, we have to plug in the XOR and we have to do a good run for the users. We have some profiles selection and of course the live ends and probably using other applications. So our vision, I have outlined now in regards to the live profile selection association, we have plans to implement more live classes this stuff. And we have a project this year at the Open Assets, which we are very likely to be printing and there is not too much interfering with cups or other system components. So this is just a machine for us and thanks for your attention. If you have questions, I'd like to know. I was just wondering if you allow users to specify different rendering contents. Yes, of course on the processing level it must be specified and once has also a lot of rules to do, probably conversions has also some application to do, image displaying and where you can see the different things. I think it's not too much related to this special topic of presentation here that's mainly discussing the association of profiles and to us. I think what you want is something like applications which use this profile as well. Also I have a question. So now we have a calibrated profile with settings to make it a certain way. How do you turn this profile on to get different settings? How would you tackle that? Do you want to use the profile as a printer settings to get more visual matching appearance or not know what's different? So my answer is first it depends. I think both things should be possible. Just to give you an insight from managing testing, one of my most important photos is everything. So it's a critical step to do this out in the manner of it. And we are targeting at taking the mass-convasion of superfile and applying it to the surface, especially when printing China, we plan to use as a superfile to set up and drive it for a special calibration system and then for this new product. OK. Let's do some impressions. Is that all? Yes. Thank you. Thank you.
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Moving the drivers colour slider and forget is a worst case scenario for ICC colour management. The talk gives some ideas on, how to preserve the relation of the original colour device calibration with the resulting ICC colour profile. Possible strategies will be discussed using PPD files and the ICC meta tag. Basic terms will be explained.
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10.5446/21659 (DOI)
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My name is Defeni Vidan, I'm a PhD student, Hopp, okay, now it's working. So I'm a PhD student in Telecom Paris Tech, which is an engineering school in Paris, and I'm studying not Dev and Card at all, but I'm studying cultural, visual culture and digital humanities, and I focus on data visualization. I will say that it is because if I say too much, my tongue is going to twist, and I would say strange things. So, and I'm also a freelance journalist, and I'm here today to talk about open source and open sources, I mean the possible interaction between open source and open data and data visualization. So, let's start with the context. Today there's more and more data available. Government, companies, cities, institution, NGO give available data sets more and more. For example, in France, we just have the Paris Open Data, so it's all the, I don't understand what's not working with the computer, but so there's more and more open data everywhere, and we are waiting for the data.gov.fr for the end of the year. So it's kind of a big opportunity for us to have all the data that are now available, that used to be staying in shadows. The other ways, there are more and more tools that are accessible to treat this data. So there's more software, some of them are actually open source ones like Jaffee, Processing and such. And for example, I would like to show you the mapping controversies. It's a platform that is lead by five schools, but I don't know why it's looking like that on the computer. So there's my school, the Institute of Political Science in Paris, the Manchester University, the Polytechnic in Lausanne that contribute to that platform. So what you can see is there is student projects and the aim is to map some controversies. So who's making the speech on the internet on a particular topic? Who's talking? What the specter of speech is? Who leads the debates? Or does it get involved in that? So that's possible and can work between open source and open data. But what I like to say is that open source and open data are not all the time working together, even if this interaction is possible. For example, when you look at all that graphics that are available and all the projects that are lead by the student, you can see first that, I'll just show you like this, that using the same software, it can generate the same kind of visual representation. So that's the first limit of this interaction. When you're making a data visualization, you want it to be special. You want it to attract reader attention. So there's two limits. The first one I would say is that you can, creating data visualization, you can at first make wonderful representation that are technically good and right, but that has no meaning because there's so many information and they are not editing. Just as a reminder, there's a monster which is a teacher that works on visualization, say that it defines it like, that visualization is a process, a subjective process, that to treat data to make them perceptible. So patterns would be considered as the visible end of data. So I can remember what I was saying to you. So when you use all that software, you can all the time generate kind of similar representation, which is not really interesting for the reader at the end and where you can also get to lose your own tool like being overwhelmed by the representation. So you need editing. This need for necessary editing is more important also in journalism that works with data. So I don't know if you already use or see different visualization made by data journalists. So the idea is to dig into data, to be able to create articles and give point of view about subjects, in particular topic, and make them accessible to people by an infographic or representation. So that's why they need to be really attractive and I don't know if you know the website of information is beautiful. I don't know what's not working with my computer but trying to... So it's guy called David Mackenlis and is doing that crazy infographics. So the idea... It's not working. I don't know what's working with the format but it's not working. Yeah but I can't... I'm terrified this is really weird. Well, let's say it's gonna be okay. So when data is all made for people, they need to be... They need another treatment that the first one that is processed by the software. In MIT tests, a guy called Mike Vanziger said that data visus to be specific to all made by scientists for scientists. And now it's for scientists who specialize people to people. So that's why they all need to be treated in another way. Today, data journalism is taking more and more importance and relevance into media. So I would like to tell you about... Give you example, taking from an online magazine called Avni.fr which work a lot on data and making articles with that material. So first of all, I would like to tell you that the encounter between open source and open data is not all the time possible. When Julian Asting from WikiLeaks came to Avni to ask them to create a platform for the Iraq log, called the War Logs platform. Julian Asting wanted to be open source because it's still in use all the time. But they haven't been able to build it in open source for several reasons. First, there was a big lake of time. Then there was no really pedagogical interest. And then there was security trouble. I mean, the website was under attack all the time. So they didn't want to deliver the card actually. But there's also a lot of... I talk about the limits of this encounter. But there's also a lot of opportunities that are created by open source software and open data in digitalization. First of all, it can create new communities going beyond the competencies and the skills of everyone. For example, when you're working data journalism, there's something really important. It's the new interaction you create with the people you're working with. So in a magazine, the journalist has to work with the dev and the graphics to make beautiful platforms or infographics. So everybody has to be aware of the other and of the other competencies and maybe discover their skills and improve their own. So there's a journalist who wanted to make an infographic about this casualty of wars and terrorism since 2001 in Iraq and Afghanistan. So it's called Jean-Marc Manac. And so he first realized that and then he go to see his graphists that understand what he wanted to say and be able to create his own infographic that has been used for the article. So he opened that and the open software can be a pretty good opportunity for that journalism to first create more interaction between the people who work together on the same project. But it also can involve other people that don't know anything about CARD or DEV. For example, I'd like to show you another presentation. Wait, let's not hear it. So in France, actually, there are more and more CCTV. We're not really used to that, but it's kind of the trend now. Okay, so there's a French magazine called La Poste and they wrote an article like two years ago about, is your city got CCTV? So what they did is they took the police report and they create a Google map to locate the different cameras. And they also create a Google Doc for people to be able to give their own information about that and give the location. So that's the first project. And one night, a guy from OVNI decided to CARD. I tried to make it right. It's not working at all. I don't know what's happening. So he decided to CARD this platform where you can see your city. And check it. So at the beginning it was on Google. Then it got to an open source CARD platform. And then at the end, it went to more and more open source with this. Wait for it. I don't understand what happened with this computer. Yeah, and then there's another guy who decided to gather all this data and he created an open street map. So it was a project that wasn't open source at the beginning, but then was the people called women's and participation going through open source software and things. So I would like to say that I'm not there when I don't know O2 CARD and talk to computers. But with some kind of platform and projects, you can go beyond competencies and create communities that are all involved in open source projects even if they don't know O2 CARD. And that's why I would like to show you the last project they do at OVNI, which is a platform called Influence Networks. The idea is that people... I don't understand what's happening with this computer. It's just normal. And so with this platform called Influence Network, people can work on open source CARD, but they also get involved journalists and people like you and me. More people like me than you, that don't know O2 CARD, but I have a good willingness to contribute to an open source project. So I will show you the video to... For you to understand what is this platform. What the hell is that? I mean, I don't understand. Look, what happened? It's not normal. I just want to see this video. It's not working. It's crazy. It works. The tool that allows you to map and visualize what's going on. There's no sound. To use it, you first have to log in. There it is. It's crazy. Oh, God. Influence Networks is a tool that allows you to map and visualize networks of influence between people and organizations. To use it, you first have to log in. And you see here that you are given a trust rank. Because Influence Networks is all about being able to trust the relationships that are in the database, people have a trust rank that will go up and up as long as they continue contributing and that their contributions are considered good by the community. So to contribute, you can add a relationship in the database. I want to add the relation between Serapelin and Fox News. Here. And the relation type is a commercial relation that started in 2010. And Serapelin is, let's say, a commentator. And the source for that is an article by the BBC. So I'll just copy and paste the URL here and submit. Now I can visualize the network of relations around Serapelin. So here I only see one because the trust level of the relationships here is set on three on a scale from one to five. One being the rumor and five being the established fact. So if I go down here all the way to the rumor status, I can see all the relations that Serapelin has between the NRA, Fox News and top-down aspects. So if I want these relations to increase their status to increase, I can review relations here and assess their trustworthiness. So here I have a relation between two French politicians. I can go and read the source. And it seems that the relation is trustworthy. But since I don't really know who wrote the article, I'm not going to give it five out of five. So here a relation between Heliochlin and the Council on Paraglut relations. The source being Wikipedia, not good. So I'll just leave it at the rumor status. So I can go and review in relations or keep visualizing relations. So when you have interesting relations in database, you can start seeing the more complex networks. For instance, if I want to look at the relation between former German Chancellor Gerhard Schröder and let's say the Russian utility gas pump. Here you see that the relations are kind of complicated since Gerhard Schröder and Gerhard Schröder are linked by friendship with Vladimir Putin and Schröder's seat in Nord Stream AG in Switzerland. So it's influence networks makes it easy to see the relationships between people and the more people contribute, the more beneficial the database will be to journalists and citizens alike. Is it working? So I really like this project because it can evolve a large community. I think it's not only for the dead in the open source, but it can make people like. I don't have the skills but I have good willness to contribute to the, not to the cut, but to the information. So I think maybe open source is not only for a small community of people who have the competencies to cut, but it can also evolve and involve people that have other skills and competencies and empower them to create new and different information. It can create new interaction but also new way to get involved to a project. So that's why I want to say, do you have questions? No? Yeah? You. Coming. Why didn't you sign up? I had a question. Okay, sorry John, please. Coffee, we need coffee. Yeah, coffee? So you're doing a like a PhD in data visualization. What? I know from talking to you like it's still kind of at an early stage, but what would, what's the type of result you hope to seek? Okay. What I can show. What's the kind of analysis? Well, I can show you what I work about. Actually, that's used to, there's stupid resolution trouble. I really dislike it. So when I, when I say that I use a work on visualization, I mean, I'm not creating them. I'm working on them like a kind of art critic trying to see what this pattern can tell us about our society. I mean, data visualization are an infographic, infobis are quite everywhere. And they have a lot of teaching to tell on us and all we are now. So what I did in my first, in my amethysts was, okay, first trying to understand all information become a kind of material that have been used by artists and people. Then to talk about the way change, the way we used to talk, like we call it the Brutal Eloquence, like Brutal Eloquence. And then, oh, we're now shaping new way to access knowledge. And also, oh, that it gets closer, the, the atelier and the artist in the lab with some artists like Amon Cobb and Warren Boats, artists and also working for Google or the company. And also then another point was the aesthetic alterculturation to this kind of diagram and visual representation that you can see more and more everywhere, not only in the news, but also when you go to supermarket and you can see what's in your food with a beautiful diagram. And then just to finish, I also work on the way to represent, to represent now new digital identities. There's more and more possible ways to see, or you're linked with people. And just to finish, to answer your answer to your question, I would like to show you, like really briefly, and visualization that have been made about open source projects, like, oh, different dev work on the same, on the same projects. And it's not like informative, but it's beautiful to be able to feel this imperceptibility. I mean, with this thousand of people that work on the same projects, you can really realize that it works. And, well, sorry for the music, I'm not really into Peruvian flute, but I didn't decide. Now I should take a little bit of a break. So I will stop it now, but for you to have an idea, I can say that you can see what's in your book. Yes? Did I answer your question? Just a quick comment. I don't know if you're familiar with Edward Tufti, but he has a series beginning with his visual display of quantitative information. He really pushes the idea that you have to be very careful as you make graphics and things to try to display quantitative aspects, that you're very careful to make sure that you're not hiding the information, that you really see the data. Some of these ways of showing information are first of all hard to absorb in terms of what it is that they're showing. And secondly, it drifts into having something this more of a point of view or entertainment than it is really something understandable. So, for example, that networking thing, well, depending on your point of view, you could run this lighter and have something that shows a conservators point of view or maybe a liberals point of view of the same information. Which one is correct? You get to the point where you're not really sure which one is correct. Yes, that's all the point about also talking with number visually. There are studies that show that you can say everything was number, with the same number, you can have two different speeches. So, it depending also, there's all the time a subjective process when you're treating data because you're going to choose the data set, you're going to choose the parameter you want to say, you're going to choose the way you're going to put it on form and the pattern that are the best for people to understand them. So, yes, that's the big complexity in the simplicity of pictures. Give a point of view when you have to and not to lie and to stay the more objective possible in the subjectivity of the treatment of data. Did I answer your question? Yes? Somebody? Another comment? Yes, I can take two minutes. It's okay? Yes, I think so. Okay, thank you so much. Wow, wow.
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The main question with data today, is not so much their existence but what is processed, their continuous use and applications,”” said Jérémie Zimmerman from La Quadrature du Net, a French organisation that aims to defend the rights and liberty of Internet users. Today, data is everywhere around us. They were around yesterday but we did not have the means to work with and visualize them on massive scale before. Thanks to the Internet and the value of sharing and transparency engendered by its long-time users, we can nowadays access and find tools to process massive amounts of data and reveal information that used to stay hidden in lists of numbers. On one side, companies, governments and media put more and more datasets at our disposal. On the other hand there is more and more specialized and specified softwares that are provided to treat and visualize this profusion of information, and many of these tools are indeed, open source. To play on words, information sources could be considered as “”open sources””. Like never before, anyone may gain access to a significant amount of raw information via an Internet connection. Of course, not all of the datasets are available and sometimes we would prefer this raw information to be delivered at in better formats, but so much is ready to be cooked. In terms of expertise, datasets and softwares are no longer just the turf of scientists and journalists, artists and amateurs are exploring them. The increasing number of data-visualizations produced by people or making platforms that help people to create their own visualizations is an emerging tred. This presentation, focuses on data visualization. It puts in perspective the notion of information and its possible changes in this “”open sources”” world. The presentation of several examples taken in from media and some artists portfolio is shown, as well as paths for audience to get involved. Etymologically, information is what is put into form. Does the fact that we can all potentially process databases, extract meanings out of the information and visually represent data thanks to open source tools, modify the shape that information used to have and the how we used to interact with it?
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10.5446/21660 (DOI)
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Yes, I'm Sebastien Rois and there's also Louis Bouchard here with me in the front. So I'm really happy, we're really happy to be here to present. Something that is, that might sound familiar to some of you because we presented Light Twist, our multi-projector project two years ago at LGM here. Anyway, so the project today is easy multi-projector desktop using Light Twist, Compi's plug-in. So Compi's is pretty new actually. So, well a quick overview, so I'm not going to talk very long. I'm just going to remind you of what the Light Twist project is and then mention Compi's, how you align projectors and then actually we'll do a live demo. Just a quick thanks, in our lab at the University of Montreal just next door in the computer science department, there are many students who work in computer vision and so what you see here is a branch or a sidetrack of many of the work we do and these are the students working on these projects. Okay, so what is Light Twist? Well, it's a multi-projector immersion software that tries to allow you to project with many projectors on any surface you want and the key of this system was that you don't align by hand. You use a camera and the camera is going to take pictures of the screen and align everything automatically. And so if you were there two years ago, you saw a demo of a cylindrical screen, so that was done with Light Twist. Now, the key in a system like this is that you have up to, let's say, 12 projectors and you need lots of machine and they're synchronized by network. It's a pretty complicated setup. It's very nice but it's complicated. So I would say the problem with that is that no one can actually use that very simply when they have few projectors. So the goal of today is to actually propose something a little bit different. So this is a reminder of the screen that we brought here two years ago and it was pretty big, 5.5, well, almost 5 meters, 7 projectors. It took quite a few people and a few hours to set up. So this is not the typical screen you set up in your living room to watch a movie. By the way, we have a version of this in our lab which does also stereo projection. So you have stereo cylindrical, immersive stereo projections. They're very nice and they're also double the trouble if you want. So some people here might recognize themselves. That was taken last year by Yuval Levy, actually here. It's hard to recognize people with the little square in their face but anyway, that was inside the screen last year. Now, the word on comp is, so our goal is to make multiprojection very, very simple and we figured the only way to make this simple is to forget the requirement of having a player software that will play video and images and things like that. So the only way to do that is to actually distort the desktop itself. And the way to do this is to use comp is on Linux, works really well. So comp is, if you don't know what it is, it's what makes all the window jiggle and all the fancy OpenGL effects on the desktop. And one thing that it does that it can do very well is to distort images. So we figured actually, why not create a standard plugin that people can just put on their desktop that will help them align projectors. So that's the idea. And actually this, once you have the plugin, becomes extremely simple to use. Okay, so how does it work exactly? Well, you use this distortion plugin that you just enable and then you need to create what is called a lookup table that will just take pixels from the screen and figure where they should come from from the desktop and do the, the, the, the, the, the, the selection of the pixels. And it comes in the form of an RGB image so that it's easy to look at, nice to look at too. It's a 16-bit PNG. And by the way, I worried about the 16-bit PNG. If you want to edit the image, then you need to use Krita, which works really well. But I might have a feature request for that. Krita does not preserve the text tags in a PNG file. And we do hide a lot of information in the, the text tags of the PNG files. And it would be nice to be able to save them. Or maybe, maybe I'm wrong. Really? Oh, well, very good because that's nice. Yes? We store the brush presets in PNG files. We just rename it to KPP. And we use that part of the file to store that. So we had the book, so we had to fix it. Very good. So actually, this is a very nice addition because in the PNG, we don't store that much information, but there's a little bit that's important. But anyway, otherwise, it's a standard image. And the red actually encodes the X coordinate. And the Y is encoded in the green image. And then the blue, it just encodes the blending that will be necessary between the projector. So it's very simple. Works really well. By the way, the plugin we made for this is actually based on an excellent FBO plugin by Alexander Lang. I want to mention this. This is in the companies.card. Now, how does it actually work? Well, it's very easy. That's a pixel on the screen, which means on the projector. And to figure out what color you're going to put there, companies will actually look in the lookup table in the red, the green, the blue. And with the red and green, we'll figure the position on the desktop and just pick that color and then multiply by the blue stuff to get the nice blending. And that's it. So it's very simple. There's no loss of... It's very efficient also. You do that for every screen or every projector. Now, how do you create the lookup table? Well, you could go to Krita and just draw one, but of course, it's not going to work really well. You need to align, and there are two ways. You can align by hand or you can align using a camera automatically. Now, to make things simple for now, we propose that if you have two projectors or maybe three, but basically if you have few projectors, you could try an alignment by hand. But you need a flat surface like this one here. It's good. The projectors must be perfect, which means no radial distortion. But that's okay, actually. Most projectors are pretty good for that because lines must look like lines. And then the projectors must... Sorry for the mistake. They must be overlapping. If there's no overlap, it's very hard to align by clicking on points. Anyway, you click on a few points and then the projectors will be aligned. So our contribution here is the plug-in first, but second, there's this little side program called LT align that will make that part work for you. So you just click on a few points and it should work. So in practice, it's going to look like this, where this is two projectors that are overlapping, and you're going to have a couple points that you have to click on, and that's it. It's going to be all you need to get the distortion working. Now one last word about what's next. Now since the lookup table is an image, you can use different ways to create it. And so this is the simplest way, but if you happen to have a curved surface or weird projectors that are bouncing on curved mirror or all kinds of things, you can use a camera. And so we will provide a different program for using a camera, but they will generate the same lookup table, so it's going to be the same compass plug-in, so everything will work the same. That's pretty much where it's headed. Now the Light Twist project right now is still working for big setup, but this is not something that is useful to that many people, because first of all you need seven or eight HD projectors and also space. So we expect that this will be very practical to make most computers that have two video output to be able to do very simply multiple projections. So for that you'll need a camera. Now just to conclude what I had to say about this, so this is basically an attempt to make Linux multi-projection more accessible, easier to use, and it's really focused on simplicity. And while the website to get the information and the web page that described the whole thing in detail is Vision 3D, and that's pretty much it, and then we'll work on the webcam stuff later. Now, so this would conclude a little description, but maybe we'll try to do an actual demo. So let me just shut this down. Okay, and as Louis goes on to make this work, I'm going to try to describe what we're doing. Is it possible to lower the light? How about this? Now what we have here is two HD projectors, so they're 1920 by 1080 projectors, and you notice they are overlapping, and we've already set up the system so that it's obviously... Oh, you should start busy flag just for the heck of it. We did all this just to be able to play the time game busy flag, of course. That's our goal. As you can see, when you don't align projectors, you have a slight problem where you overlap. So anyway, we're going to try to fix this. So, well, there's not much point in playing right now, I guess, but anyway. So we'll try to align this for you in several years. So the first step is to start the little aligner program, and it will light up each screen. And the most important thing here is that the overlapping of the two projector is the key. You need overlap, and you go in the first screen and you click on four points to... I think I just four points in the overlap, and then you go to the second screen, and by the way, the cursor will turn into a little X if you're not on the right screen. And then you click again in the other screen, and now it's going to show up in green. Now, green on top of red should look yellow, so I guess if it looks yellow, then it's pretty much aligned. And your goal is to align the points, the red and the green together, and you can move by a tiny fraction of a pixel using the cursor piece. It's very easy. And when you start to see yellow everywhere, then you're really happy. It means it's pretty much about to be aligned. Okay, thank you. This looks pretty good. Okay, and now the second step, the last step, is to define the whole screen area you want to use. So you just click on the four points that define your screen, like this, and it will show you how the screen looks. Now it's up to you if you want a perfectly square screen. Well, just measure from the ceiling or whatever, but this is going to be your final screen. Okay? Yeah, you have to maximize every pixel. It's pretty much it. Once you're done, you just, what is the key again? S. Yeah, the keys are not super sophisticated. So, S for save, and it's going to create the two lookup tables, and you're done with the alignment. That's it. Now, all that remains to be done is to get the compass plug-in working, and it's already working, right? Okay, now this is running, you went to 10, 11.04, the latest, and we do have to restart compass by hand to get the CCP flag going. It's a technical, yeah. We're still trying to figure that part, but basically you restart compass if it doesn't cooperate, and this is the option control of compass where you start and stop different plug-ins, and so the plug-in is called light twist, so you just enable it, and then you have to give in that plug-in the two lookup tables, and once it has the two lookup tables that you've created, then you just start the plug-in. That's the first one. Well, there's a gamma parameter also, but we try to keep the number of parameter as low as possible, because it's a huge bother when you have 20 sliders to adjust things. Okay, I guess we're done. Are we done? Yeah, so when we're done, we just activate the plug-in and just activate the distortion based on the lookup table. And yeah, and there you go. So now you have a screen, and yeah, so that's your new alliance screen. Yeah, it does work. We've also added some anti-aliasing to be sure that even like a one pixel line actually gets distorted properly. So now how about we play, yeah, let's play BeZfly at last. Okay, so now actually put this game is a, this game was meant to be played on a huge screen, a huge wide screen. So I know we're following someone, right? So hopefully he's playing, but yeah, of course we could probably follow some. Yeah. Yeah, get another server maybe, it should be fine. By the way, most games, well like BeZfly is nice, it's going to go full screen instantly, but most programs when you tell them to go full screen, they don't go full screen, they go full piece of a screen, which is not always great, but this is something you will notice. So anyway, I guess now you can play BeZfly here. Yeah, yeah, so I guess people are just not very active today on this BeZfly, and I guess we won't start playing. Okay, but you get the idea for this, and this is an open GL games, it works really well. Okay, let's show a couple more things that could be useful. What else? One thing that could be interesting, once you have a plugin like this, it means that every program suddenly becomes multi-projected. This means you can have a GIMP with a huge 4000 image at one to one ratio, and draw really high detail in escape or whatever, and you can have a huge range of programs in Blender, and this is what, yeah, this is GIMP. As you notice, the tools are really small, but this is a, let's see, so I guess, yeah, this is going to be our image. Can I have a bigger image? Can I have one? Okay, yeah, okay, so it should be bigger, but this still hits a 3000 something, but you will notice that although it's very well aligned in the middle, you might notice a slight change of color. This is because the lamps of the projector are not in sync, they are not the same age, and also there's a lot of tricks to align color perfectly, okay? And this is something maybe we'll add, but we don't want to add too much burden. The first step is definitely alignment, and it shows only when you have white. If you start with a black image, you're not too bothered. Now, what else? Oh, yeah, and movie playing is nice also, yeah. We have a couple examples. FF plate will go full screen on the whole display. So this is an example. It's a little clip of an HD movie, but as you can see, FF play movie will just play right away and be really happy. And you can play as high resolution as you want. It's going to work. So this is a very nice way to get your home movie theater going. All you have to do is find a couple of projectors, and the rest is fine. By the way, the price of projectors is going down very, very quickly. So this is becoming an alternative, but we figured, you know, why not have that used for the computers? It's very nice, and you can have a lot of shells open at the same time. So do we have another... It's basically any program works on there, but we did not install that many. Maybe a Stellarium, is it correct? Yeah. Most people, you know Stellarium, that's the Sky, open source Sky Viewer program. And this one does not do full screen by itself. You have to actually make it really big. But what's nice here is that it's an actual Sky View, and you get the full resolution of the Sky. And actually, well, of course, now it's a little... It's not dark enough to really... Oh, it's a button. Yeah, click on the button right there. Come here and click on this... Yeah, this and this and this. Yeah, remove this stuff. Yeah, this and this also. Yeah, this is a true night sky, but still, we have something lighting up. But as you can see, this is an OpenGL program, and it's the same. You get really high resolution now. So many programs become very, very fun to use. Yeah, actually very fun. Oh well. So maybe I will just stop there and let Louis move around the stars, and maybe answer a few questions if you have any questions. So perfect to ask. Otherwise, well, I guess that's our demo. Oh, there's something else to mention. The code is, of course, available. So it's not available as packages and stuff like that yet. But still, you can download the tar files and compile that very, very simply. So it's something that should work right away on the... Oh, actually, yeah, you can go to a web page. It's very fun to browse at 4000 pixel wide. Yeah. Yeah, so... Okay, so this is the web page. Does that make any goals? Oops, no. Plus, yeah. By the way, YouTube, stuff like that, Flash, it all works. So, yeah. Anyway, so yeah, so it's on the page there. All the instructions are there. Lots of dependencies, but it does work. Yeah. So in the future, we hope maybe we could integrate that somewhere inside the Compass package, for example, but we'll see. So anyway, so that's pretty much the presentation. So thank you very much. And... If you have any questions, well, feel free. Oh, where was your family? Actually, more of just a quick comment rather than a question. Because I was just thinking about Lightwist and what it's done recently the other week, because I went through my BigBucks store and they had nice projectors for $900, home theater projectors. And then I went by my local Target store and on the clearance end cap, they had a home gaming projector on clearance for $99. So I was thinking, what could I do with that? Yes, I see. There you go. And by the way, of course, most home computers have two, you know, more graphic cards have two output, but you can buy also the video splitters like MatRex does one, and you can have two or three screens hooked up to your laptop. It's very feasible and that is very portable. But yeah, you're right, the projector's prices are really going down. It's not a joke. It's really, really true. Now, a question. I was thinking about what is the future like with GNOME 2 and the problem with GNOME 3 and Compi is that it's not going to be continued. So are you thinking, Minto, like merging or migrating your plugin to something else or overclutter or something so it can actually work with GNOME 3 and stuff or because obviously we're going to move on as the future comes. Well, that's a really, really good question. Because it's an excellent functionality and it will be really same to lose it if you're moving on in the future. Yeah, I think this, yeah, because it's kind of useful, it would be nice to have it integrated so it's pretty much seamless and you don't have to install anything. It should be natural to do this. And also, given that it's, I mean, I have to mention that having an open system like Linux makes it really easy to do that, but it's not that easy to do that on Windows or on macOS. So the question of what's the future with Compi is, I'm not sure. But one thing I'm pretty much sure is that OpenGL effects on top of Windows will be there when we are another. And I guess the plugin concept has really proven itself very useful. So as long as that stays there, we're going to be moving this into whatever environment becomes... It's not that hard to rewrite for an other program. You're right. It can be rewritten very easily, no problem. Yeah, we'll make sure it stays there. One last question. I want to comment to this last statement. I think I'm also a maintainer of a Compi's plugin, an independent one. Compi's goes on Ubuntu, it's a Unity platform. And for independent plugins, this would be very useful to have one common format to write plugins at least for one operating system. This should cover KBIN, Compi's and Matan, of course. Yes, yes. Well, yeah, if we can participate in that, I would be really glad. It's a lot of work to... Yeah, it's a lot of work to record these things, so many different... Yeah, sure. That's okay. Thank you very much. Well, thank you. Thank you.
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We present a new compiz plugin to use multiple projectors, in order to obtain a very high resolution desktop (with two HD projectors, the desktop is typically 3800×1000). The most important feature is that projectors alignment is done manually (very quickly) and the edge blending is computed automatically. The result is a perfectly aligned, anti-aliased and edge-blended desktop.
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10.5446/21662 (DOI)
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Hello again. Besides Kribius, I worked on a couple of projects this year. It forms something consistent across the graph and related to an experience coding, related to graphic design, and even graphic design in general, and maybe a bit more than that. So I have a list, in fact. I have a list of programs I worked on, not on all programs. I don't know if some of you remember. It doesn't work? No. It's not working. OK. C. C. Muehl? OK. So the first one, I don't know. No, I think I know. So under type was the first program I worked on. It was an attempt to have a typesetting program without any text engine. The idea was that I didn't want to deal with text at this moment, but I had an image, an imaginary of what should be a well-composed text. And I had the idea that it was not possible to achieve this by using a text engine and text processing in the way that you have a text collection of charts, and you want to turn it into a collection of glyphs. So my idea was under type was to have something. It was a program, actually. You have something like a cast. I don't know what time. Oh, say a glyph collections. OK, it was like mimicking how you do this by hand, generally. And I wanted to get something like that at the end. Something like, which is, we discussed this term about the efficiency of the PDF generation. So it was like my first program. The PDF is like old plain text. OK, I wanted to have something like that. And it turned out when I was speaking with a friend from Co about this program that I wanted to show her where it is. This program, I had to compile it again. And I wrote it maybe three or four years ago with QT4. The early age of QT4. And nowadays, you can't compile it anymore. So there's no, it was, you know, because the Q variant can't hold the void pointer anymore. So the program is completely broken. And I had the choice to fix it, or just to accept that this nostalgia of type setting is over. And I just have to give up about under type. It's a bit sad for me. It's a switch, but it was under type. So the next big step was font matrix. I presented a couple of times in GM. And after I stopped working on it for almost one year, I've been somehow hired by Dave to continue the work on font matrix. And we came up with a nice project about what to do to make it really widely used and best font manager in the world. And I think we were quite excited. And it was really nice to come back to font matrix in this atmosphere. So I will show a bit of font matrix. Oh, before I show a bit of font matrix, I want to speak about something else that happened one month ago. When we were in Vietnam with OSP, we had a workshop. And during this workshop, we wanted to show a website of various graphic design related projects. And one of them was font matrix. And at this moment, what I discovered on the font matrix website is an editing of the website by someone else, someone who is not here. Alexandre Coedin. So Alexandre Coedin related to font matrix. I don't want to speak of him at large. But for font matrix has been the one who documented font matrix in the first place. And the way he did it was so crazy. Because it was when we were releasing maybe the 0.6. And I was in a rush to have it working. And he told me maybe 100 or 200 times, with the documentation I wrote, please, with the documentation I wrote, what do you think? And a few days before we released this documentation, I said, OK, I will read it. How we are. We don't want to cope with documentation. So I started to read the documentation. And in fact, this documentation was first, a full documentation of font matrix in every details. And it was crazy because I don't know if some of you use font matrix a couple of times. It's something like a bit messy. A lot of features are done everywhere. And he discovered everything. And he sorted out every mechanism in the program. And on top of that, he wrote a beautiful text about the freedom in typesetting and for free fonts. So it was like really, OK. I won't say. So he wrote this. It's been one and a half years since release of the latest version 0.6. The project is not very active at the moment because its principle developer, Pierre Marchand, is rather busy with other things. So version trunk is currently 150 commits away from 0.6 and features a rather simplified user interface with few new features like name filters. The new user interface is not yet finished, with some of the former tabs currently being floating windows. Eventually, we will finish the changes in UI, document DOM, and release the next version. So it was really crazy to have Procode in writing on font matrix. We didn't have contact for almost six months now. And it's nice. So I will show you some of this stuff. This is the floating window. You can type set in font matrix as well, if you like it. So the main purpose of the changes in font matrix was to make it really straightforward to find a font and not to dig into menus, et cetera, et cetera. So the whole thing is to display fonts. And the most fonts you can, at the same time, and give means to users to filter these fonts very easily. I don't know. But to filter this large amount of fonts, to make it possible to go little by little to someone you want to use in your work. So I will just present everything from the past is still there. And the new stuff is the filter. The filter is the way that you select something like tags and a search in metadata or a penalty attribute. And you will stack them. Here it's on top of the window. Maybe it's not the best idea, but it's what we have. And this stack of researches, tags, and attributes constitute a filter that will cut off your list of fonts. And if you look at the end, you have maybe something like a page, reasonable subset of fonts that you can explore to find something. So how it works that you, I will remove this. You have the large amount of font, like we have more than 7,000 fonts. And if I want to filter the three fonts, I apply this filter to the list. And this filter is constituted by two researches. One is for the free license, the free keywords in the license field of the metadata of the font, and the open word. So it's something like you have a, when I'm looking for a free font for a job, I can just go to filter the three and see what happens. And I can refine this search by saying I want a decorative free font, something like that. Oh, no, no. It's a bit more than that. Because to be able to make it, to have a NAND on the subset of font, I have two buttons, NAND and NOT. Which is, I don't know what the definition of subsets of data. But I didn't find a way. And it's the purpose of my talk now. I didn't find a way to articulate nicely my attempt to do something which is quite personal about programming and to make it available to everybody. So you can say that these icons and the way the data is presented face to spread among users. Because I presented the program a lot of times to people. And they just don't understand, don't get what they have to do with this program. So I tried a lot. But it's, oh, I have a sentence. I wrote it. I wrote it. OK, I tried a lot. And I still don't manage to get something working. So I would reason that. It's quite a failure as a software product and a success as a software artwork. It was my point for font metrics. So I can show a couple of things that I find really nice. It's the new, let's say, free font, please. Oh, let's say, did I have a view? Why not? I like the multituet stuff. Like the text is written as long as you like that. Wow, it's nice. The charts view didn't change. And this is what I mean when I say I felt to make it really nice for a user. There are too much data. But I like the overall design of this page. But well, that's it. And another thing in the same vein is something like the specimen. There's a new specimen engine. And I don't know if you remember. I remember at first the module in charge of writing the specimen books was something very flexible that was template-based. And you would expect the user to write templates to have actual specimen books. And it failed completely because nobody ever wrote such a template. So now everything is hard-coded. So it is my choice. But well, I find it's nicer than before. I don't have, I won't explain everything. So I can continue. So the list. Nancy and Fonzie. Nancy is really like my meeting with the OSP group, really the first clash. It was at Utrecht. Like it was the workshop. Wow, this one is really nice. It was a workshop about the Dingbat liberation phase. And we had a great time with a lot of people, with a lot of trips with the USB stick to share data and new glyphs and scans, et cetera. It was really, really, really nice. But maybe two or three months later, we have been asked to do an exhibition in Nancy in France. And we thought it would be nice to have the same setup as for this workshop, the Dingbat liberation phase workshop. But we couldn't stay for two weeks in the gallery to make this workshop. So the idea was at this moment to glue all the software we used in the workshop into a new software able to run the workshop alone. But there was a mix of actual cutting and drawing and the program, and the whole thing communicates through a scanner. So this is the part of the setup. I think it's this one. So Nancy, it's just to run the Dingbat liberation phase alone. So you cut something, some shapes in a black paper, you scan it, and you don't scan it. You put your drawing into the scanner, and you answer the questions of Nancy like this. It's a mix up of English and French. It was really nice in a ski art. And at the end of the process, the drawing scan is inserted into its trace, inserted into a phone, the Dingbat liberation phase. And there's a new commit to the SVN server. Yes, at this time it was a Subversion server. Woo! The Subversion server of OSP. And after that, you can download the new phone, because it was calling a little script on the server to regenerate the phone based on the new UFO font on the server. So it was Nancy. Nancy has a partner now, which is Fonzie. Fonzie is built on the same text, I would say, because all the components we have here can be reused to build a scan phone program. So it's what we did. So Fonzie is a scan phone program. And we can do font with Fonzie, like the font we displayed yesterday. Yes, it was yesterday. And I want to show you the first font we did with that. So Fonzie is a commission work, again, for speculose, the graphic design agency in Brussels. There's a lot of ideas. It's just 10, 10, 10, 10. And it's been done primarily, in first instance, to do fonts for comic books, like this kind of fonts where the quality of the contours is not critical. Even the spacing was a bit, I have to say that. It was not very good. But in the end, we worked a lot with this program for maybe three, four, five comic book fonts. It was really nice, because before this program, the process to make this font was really tedious and really long. And when we presented this program to the partner for this business, she was amazed, because she sent the scans in the morning and the afternoon, she had the font. And she was like, ooh, it's fast. Oh, a detail about this comic font, not a problem. The specificity of the first iteration of Fonzie was to provide style sets in order to have this. I don't know if you remember. You can have in open type some kind of function to have a fake random, and Fonzie was implementing this kind of function to write a proper feature file to make it random. So when it's displayed, maybe this one is working. I think it works. I don't know. I'm not sure it works. In profession, where is it? Yeah, the two S are not the same, because it turns three or four styles. So it was fun. And how to continue on to Fonzie, directly to VJ14, maybe. So now they have some kind of a kid in gestation. So we have been asked, John and me, to work on this kind of stuff, we would say, for the next event of Constance, the Medialab in Brussels, I can say that. And the idea is to cross this program with Tesseract, which is an OCR program, and to make it possible to just have scans of books and automatically process them to export a font, a text, and a new book made of this font and this text. So this is the next step. It works. If I didn't have this crisis, it works. It works badly, but it works. And it's really fun. A lot of artifacts, but it works. So the list. Fadi Rugg. Fadi Rugg, I would be short on Fadi Rugg, but it's interesting because the whole point to speak about Fadi Rugg is another little program I did for a designer working with rugs. And she's not interested at all into digital culture. But when I spoke to her and explained how it was important to do free software for creative design, et cetera, she understood there was something here. And she asked me to collaborate for project about drugs. I can show a bit of Fadi Rugg. If I can find it. Now, I didn't launch it. If you have a second, I can. Now. So it's like, excuse me, it's not well prepared. So Fadi, Fadi, Fadi, Fadi, Fadi, Fadi, Fadi. Rugg one. OK, Fadi Rugg is like to explore the patterns made out of that comb from the, OK, let's say you have a thread of two colors. And you make a rug out of it. And it makes patterns like that. And if you change the width, the pattern doesn't fit. And it changes something. And you can explore that. It changes the width. It does something. Because you have this way. In digital images, you every time go this way. Like a scan line. And this is the Boustrophédon. I don't know the translation in English. Like you have a text that runs this way. And it's the same for this rug. The thread goes this way. So it gives something like you can explore. I continue a bit to show you. Yeah, that's fine. This is Fadi Rugg. And what's interesting is the collaboration to real design, object design. So my list. LiteralDro. Where is it? LiteralDro. LiteralDro again. Now, for drawing. LiteralDro, it's a program. Some kind of program. Like really inspired by some kind like shoebox. It's almost the same with two differences. One is that what you have here as the text input, the commands, is not programming language like Python. It's a text. It's just a text of commands. And maybe you could say it's a trick. But you have a dictionary where you can alias each keyword. And what does it mean? That this text is out of a file exported by, not exported, saved by, phone force to describe a glyph, this one. And you can, in fact, map languages on together and make people, because it was done in my opinion, to do workshops, to give workshops, to explain what were the relationships between a text, another text, a graphical output, a grammar, and a dictionary. And I don't have the actual code. Because it just forwards the commands to QT, a graphical framework. Like when you have a cubic, it translates into a cubic to call into QT, which is the C, et cetera, et cetera. But what's fine with that says, for each workshop we gave with this program, people came and asked for something else, something else, something else. And because it's the purpose of this program, oh, you have the HVGA output here. And because it's the point of this workshop, this program workshop, this workshop program, to deal with the text and to make people unaware of digital culture into this digital culture, we come from this text, it's simple in context, to the actual code running this program. And there's something like we are going from this text to the text of the code, and we're coming back to this text, and we'll write something else. And it's all this, it's a tour de Babel, Babel tour. OK, well, so I won't present everything we did with this program. It's huge, in fact, because I had the idea. No, maybe I can stop here, because it's the end of the list. Yeah. Yeah, it is there. My work of the year. APPLAUSE Comments, questions? What's the comment language used postcript? It looks so short. Excuse me for literal. No. No. Yeah, that's. Yeah, just. No, no. I mean, it's just a list. Move line. Yeah, my idea, when I present the workshop, I say that this vocabulary has been written first time for post-create. It's exactly the same that you can find in every graphical framework. And to explain what's digital culture, we have a first text, the Bible is the post-create reference, which gives a lot of lines to continue to work with digital graphic. And now we can have this culture, and we can have it in the SVG. It's almost the same. We don't see it here, but you have the same terminology everywhere. And I can work with every language, whatever Python, QT, or JavaScript, or whatever. It's the same thing. And you're never lost into the language or something, because you know what's digital shape, what's a contour, what's a stroke, what's a field. What's, you know, it's what I want to share with people when I show this program. But I didn't say what's important. First, I didn't want to implement some kind of post-create interpreter, because post-create is a programming language. But yesterday night, when we were speaking about this program as friends, at the end it appeared that last time we added something into the possible commands, someone asked for variables. So a new command, like you can store variables into the program to reuse them later in the text. So this text, this data, is little by little, and by its users, new users, turning into kind of programming language. It's something like, and I want to explore this process. Yes, sorry. This is not a question there, not a question. So it's a really quick question. I'm actually looking for someone with high programming skills. That's not me. It's not me. Are you sure? Anyway, whether this process reminds me, I want to generate identity icons somewhat differently. And this actually reminds me, you take the MD5 sum and then you turn it into something which is randomized, but not randomized. I thought maybe this is the kind of project that might interest you. That's all. Yeah, yeah. I'm not sure, but it involves syntax analysis, et cetera. But it's the next step. I don't know. I will. We are going to give a workshop with this program. And we don't know where it's going to. I mean, it's time it shows up. There's something new. We don't know. Yes? What was the output of the workshops like? The output of the workshop. I was looking for the output of the workshop, but I didn't find it. It was like, I love Vietnam with the art in the middle for the most exposed thing. But this is an anecdote. But the actual output of the workshop was like some, even in the workshop in Vietnam. Yeah. So the workshop in Vietnam was really interesting because we weren't in this workshop with people not speaking at all English. So we use this dictionary as the base point to communicate. And because people was looking for translating under the Google service, and after that we had the full text in English, or kind of English, and in Vietnamese. And we could start to communicate by writing this text and doing stuff. And it was really crazy. It's the actual output of the workshop. But I don't have the resume because it's a mess on my computer. Maybe I can finish that. Thank you, Dan. Thank you. Oh, yeah. That's something else. It's something I wrote. Maybe it's not well written. It's like, so thanks to all of the ones who released source code. They built the library where we can force our sensitivity. Thanks to Ada, maybe even more than Babbage, and I'll disclose this fabulous story to me. It's for me. First to you, the Librafic Community for the warm welcome I received when I came to you. Thank you.
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A year at programming for graphic|product design with free softwares and freedom in mind.
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10.5446/21671 (DOI)
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Okay, so what are your views on colourful... Colourful... Colourful... So... Good morning. I'm Richard Hughes. I work for Red Hat in the SIP team. I live in London and I've been doing this colour stuff for about a year. I also maintain package kit, no package kit, no power manager, no power manager, no power D and I'm a customer for loads of other projects such as UK and Geneva and stuff. It's been an epic source for the world but I'm pretty new to this whole colour stuff. So in the presentation I'm going to explain to you basic principles like gamut, what an ITC program is, what's important, go through a typical workflow, go through what is required for colour D and key design to be able to promote, go through actually how it works, impact implementation, talk about the session component, in this case the car manager, I've also mentioned the key user. And then we'll go through, so really quickly we can have a lot to talk about. And to answer some of the questions. So these are the questions to the end. Of course hopefully any questions will be answered on the next few slides. So let's get going. So actually colour is really hard. Colour is really just a radio waves which we can process as carolies. You might think the colour is a processing of an object, but actually it depends on the lighting, it might depend on your colour line, it might depend on how many different things, the screen looking at, working on your photo. So actually colours are quite a complicated thing. You really need to make much simpler before you actually mix up the work. So when we did the colour we did it with very different devices. Now just your camera, you can take a photo which can capture millions and millions of colours, more colours than you can take a photo in the brain of the model. Now if we can display them on the screen, we might put them on our digital black panel or a cnt display, which is a big cake of showing a few hundred thousand colours. So if we want to do less, we have to work out how to map colours from a device of loads of colours to a device of a lot less of loads. And then we might print more of our photo out, so you might print out a photo of some kids, some other kids, which might be different again because instead of using light red and blue, we may use a pink, so cyan, magenta, yellow, black. And we have to manage to colour them. There's no way in the world we can make these devices all the same, so the blue of the camera is going to be much bluer than the blue of the printer. But we can tell you some ways to do it right, and also maybe try and make it a little more efficient. Or without that risk of using loads of options and light, but we'll just use them. So to do this, we have to map the colour spaces. So on the left hand side you can see an example of a S-R-G-V. Now the weakness of all shapes is actually what your rights can see. So that's the limit of our human vision system. And the light-shaping area is the colours that they can create. So that's what you made. It's a good approximation of a 10-year-old monitor, the C-R-T-M-O-N-T-A. And it's currently used by most of the toolkits, and now it's confused by most of the internet. As you can see, we can see that loads of colours we can see. We can't express a lot of deep greens, we can't express lots of balloons or wets. So actually it's kind of showing a savage now. Monitor's just showing me more colours. We don't really want to be able to strip ourselves to this very small set. So the limit example shows you what a doggie engine looks like. A doggie engine being a spot to call entity space, which is used by designers because it can express so many more colours. Because it's a well-known space, if you know it don't be, then you can export web-tales in as well. So it's big, because they're more balloons, many more greens, but they're more reds. Now the shape triangle is actually a lot of shape, and it's actually a 3-metre hole. It's a bit more complicated to just try and look. There's a couple of little strokes that come up well. And the last space is a little pro-photo, actually. Now this is a massive space. You can even encode colours, but you can't actually see. It's kind of quite wasteful, but it doesn't mean you can't actually make any more colours. So you might think, you're so okay, this space is bigger, is it not better? Or if they're encode pixels with a bit of pixel, on this small S1GV space, we might have 30 or 40 skin tones, which are really big key colours. Using pro-photo, I should say, because of the larger range, you've got a much closer quantisation. You actually might only have 4 or 5 skin tones. So unless you've got the 16 bit of pixel, it's not great. You can see that each colour space has its advantages and weaknesses, and it's not going to be anything like the same just use this one, just use that one. So this is an example of things that start picking in the winter. Although it has slightly less highlight on the camera, suppose we're rubbing on a frosty floor. It is great, the red is quite clear, the south red looks like a bit more gel-oak. The white is crisp, the black looks sharp. And I think it's important that it's 1960s, well, not that time. Now, all the Nova Springs are very high-confiniture, they come across really low, and it's two years old, my little son. And so the background is kind of dim now, and so it's kind of a bit darker, and the colour looks a bit much now, because it's not as if you could explain. So I printed it on my nice, shiny HD printer, and it came on the right side, so the blacks are pretending to be this money-brown colour. The white, the paper white, isn't white, it's kind of like a light-shaded blue, and the red's a completely different red, it's a much more extra-sour, even if you look. This is a total failure for the user, but the user is printing and registering a photo, and it has very few resemblance to the image. So what can we do? We can't obviously make a printer, but if you like that ink, then it actually has a little coverage. We can't make a print white side for the actual paintbrush itself. What we can show you is just what it's going to look like. So it could be able to make colour-correcting images so they look extra, so they look a bit more representative to the photo. Or could we tell the user what it's going to look like and it's going to look like a print printing kit we've used to tell reference to show the user the actual words of the look-like that they're trying to print. So how do we fix this? We use something called the Nicency Procurement. Now, the Nicency Procurement, we use the finally blob of the user, which characterises either a colour space, like this RGB, a DBRGB, that kind of thing, or it can characterize a device. So you can tell the Nicency Procurement on the display, my print is up, scanner, my camera. And you can have a profile per device. We get this thing from 8 and you can't manage quite the work. It's kind of a digital environment. So for example, for Pixar and Dreamworks, this is what they do. They have the look of the photos and say this is always going to be a problem in the experience. There was an inclination from that to play this job. Now, we have what you think, close to that in nice X, in Windows, or anywhere near in Linux. There's kind of something that we should try to aspire to. Now, with profiles, you might have seen some people might have already downloaded them from the website. Manicaptors try to really help things and provide sort of pre-cured, generic profiles. So if you go to the line of websites for a T61 backup display, you can download the Nicency Procurement. Which is great, you can have a great comment or display. But actually, that's probably the average of 3 of the 4 monitors of production line in some way, in the battery two years ago. But actually, there's a personal experience from something that's snatched to T61. You can buy T61 panels from Taiwan, you can buy it from China, you can get it shiny and you can get it glossy. Try to over-cord all of that to one G-Magnet profile. Kind of misleading thinking you've got color managers to let them actually have it. So really, you've got to be very self-cubrocheted because, I've noticed, the layers get dimmer as they get on top. So, 3 of the raw display is something like an 8th for the bright 20-40. Now, they also get more of that, which is kind of changing your colors as well. It's kind of biodegradable to artists to show them what they're kind of looking like before and after. Now, I like ZX, did this right. It's sort of 3-release to go. They use a system called ColorSync. Most applications for ColorSync nearly on the right side of the color system. They're actually very hard to not be color-matched to other cells. Which is kind of one of these things. Drawbacks in the profile of the screen is actually very difficult to say, because they can leave my image alone. I guess, we'd be able to leave this complaint with the same background, so it generally works really well. Now, whether from the system, first of all, in this color thing, whether it's color model, where there needs to be some vSync profiles obstructed in hours that are only this specific stuff, so you can plug in various blocks of IP. And it kind of worked on this stage. Windows 7 is much better. Many more programs support the system. Many more better-sounding programs that have conveyed our Windows color system in them. That said, most drivers in Windows 7 don't do color management, so you fall back to SRG. So really, the situation by-set is 9 out of 10. Windows 7 is 6 out of 10. And then, at the moment, 1 of the insurance. So what can we do to fix this? Well, this thing of color-d, I can't do that. This thing of color-d, now, color-d is really just a color-d. It doesn't really do much for the store. It really just deals with mapping programs to devices. So I can say to color-d, give me all the color-d parts of my system or give me color-d more of my print-serf or print-serf was the paper. Or I can make the system and give me the list of all color-d parts in the system. So it's really just a high-level kind of framework that can help you to do the wrong thing. It provides a very high-level D by St. Wi. So being D-Rust, I can find that color-d in the store, or the API. But it's very high-level, so you can really make applications that inspire you. And it provides a D by St. Wi. So you can say, do you use an overriding system? I think St. Wi is a little too......cover the screen and associate a specific profile with a specific display. You sort of have a thing of a screen based on the picture and say, the profile is available. You map it to the client. It's pretty usually the message on the screen. And what do people kind of question? You know, there it being a system doing that all one-night for done in a session. I can't explain that. It did really work very well for two scenarios. First, the cups has to be a system statement. So we have a process to sort to 100 feet of......a shot with a card stick. And also things like the GDM script. Those are actually usually locked in. You need to be able to set profiles and work with a protocol. So it's kind of simple, really. I think it's... I hope it's 100 frames. The bottom line is that I know this is a system statement. It's not part of the session statement. So you can see here, it's not the same option. It's not support. It's sort of a new dose to get into the initial panel. It's not going to be cups. Or rather, cups is talking to it. So, the difference is cups is......cups are recommended for the person who is certain to be able to get a top level. Cups are going to create coloration of ice in the company. And have any profiles already in the future. So, the link in coloration. Coloration works. Color sensors, which I'll just give you an example to give you. Which basically means that the rate of fire in the moment makes for giving color. Or a more respect for the risk of catching. Coloration is a direction profile. Coloring of conflict. So you can set things like the overrides. Or you can set a rate of overrides. So it's not the problem in the matter. It also has two depthfaces. The first one is color wargifts. It's the nothing from the profile device. The second one is the depthfaces. And the other one is the storage. Which actually has the kind of assistive virtual profiles and assistive virtual devices. Which kind of seems a bit characteristic. But basically means you can have things like a printer that you know what you're talking about. So if you have a printer that you can put in your photos online. And you can send it to your field like for the shot. So you can set the color bar. So this will bring the sous-tendent. So you can create a print line, and you can actually revise it. And the current classic feature, I'm not sure if it's a family-grown idea. It's a product that's changing. And I think that one of the main components is it talks to the assistive system and the permission of the product. It actually goes into direct access to cells. And the parcel of the product is the top level sort of primary representant in the system. And the top level is the session. The session for the GSM session. The known through the system. I'm just blocking it. Now let's talk to the apps. The reason we're talking to the apps is because the system deals with the access to the apps that the accession is. And it also sets the option on the GSM. And our gamera is supposed to display the operation. We have to do this in the session. The GSM session also loads protocols on the home directory. It does that itself on the price. The reason and reasons. First being price of the product is very low. Second, probably the SELIME. The idea of the assistive demodulating of the root rather than the SELIME directly is a plan for the accession for us to learn. And the third reason being if you're having a cryptopendor actually, you can not even use the number. So the financial data protocols can be used in a bit. And not in the session. Two other things. GSM practices the control center which is the pain plan. Which lets you assign over a rate of protocols to devices. GSM view is kind of like, kind of like, you guys have to use, but not really users. So we can see, all the customer profiles having the same amount of data while having this color space is not going to be a question color search. Now, the printing architecture is kind of complicated. All the time I rewrote the get to roster to interface the quick-comedy now. That's another lot of string. The romantic integration which was the post-stretch also goes to color-de-now. So for a document to be printed, I've got a document being printed from glossy paint, and I'm going to make a protocol here. More for a question and use for the output device. Kind of works. It's a bit of a time-out, but it's kind of complicated. We need to know how it works. So, it's really about loading information really quickly. So just to cover some key points. It's a system dealer. It's a dealer interface. It's system activated. You have to have your color-de-now devices, and you have to do some work to use color-de-now devices. So, for a dedicated device, it's a few very many good stuff. It uses policy care. So, some stuff you might want to use is not to be able to delete the devices but be able to query them. So, you can control what you can possibly do. So, we have one single interface for map-ins, one single interface for virtual devices. And I guess the key things to take out of this is the kind of the things that work with CNA, the color-de-now framework, more than the color-de-now device engine. Others like the ASU maps to other ASU maps, they can do a really good job of taking pixels, and then sort of converting these into color-transform. Now, color-de-now can drive to the near-hat. That's the job of some of the templates that's in that in the virtual-earned stack. There is a high-level sharing between user and the community. So, I talked about choosing the broke-levels of the printers. I'm going to go to the virtual-earned stack for a 3D panel. I would query a lot of color-de-now to get the broke-levels of the printers. Using that, we can have broken-up the match-down to pull back to any virtual-earned stack for any resolution. But the use is on the calibration level of the protocol. It just helps any protocol, any non-strictly protocol, and it's kind of crude in letting us through the documentation. It's already more happily using the color-same, so no blocks in real life. But unlike Apple, we don't actually limit those to three dimensions. This is just a strange box of color-de-now. There's no reason to put it up in front of the mutation, and it had a lot of pecs in our objects. It must be this way, with that, so we're not limited to sort of the unobtrusional logic. Another thing that's determined the content is, basically, the user is almost live. So even if you have a big protocol where it's loaded from the DVD file to the load-game protocol itself, it's kind of the internal protocol. And the user then profiles to fly Steven. Even the protocol doesn't affect the personal plate. The protocol's much better than the original protocol. Similarly, for the slates, you have a protocol that's all to generate from the EDIC in the past four months. That's going to be worse than one that's actually used in the theory or the one on the key to that calibration device. So anything that's all that's been added and done as a protocol heuristic is a soft protocol. All that's because Trump's finding the new part of the partnership protocol. Now, what does it say is that it's fixed? And really, what the protocol limit is, is that the language is what he must have been saying. Luckily, that's kind of gross on them. So the fact is that we want to get the attributes, the flexibility, the features, especially when you're using cool, big, hot color to anything that's up to your HP. Then it can work. So if you're backing all of those together, you need to want to find devices and protocols in a different way. So for a protocol that's more of an eager protocol as a file and has a checksum, I usually have checksum part by the self so it saves time collecting it. But protocol is a kind of trick what you should say. That's protocol with properties, methods, procedures, back and forth. Devices is a bit harder. It's kind of color management specific because a scanner displays, do you have a scanner? You've got two scanners, the same like in the model. It doesn't have a lot of inflection of that to put years later. So it's very easy to do variation. It's a scanner, but I'm not sure how I can use it. It's a great account. It's usually twice model name and vendor name as the key. You can not use it. But for display, there's a significant variation between two different vertical slabs. Are they made of batteries? They might have been more modern than they are. I'm not sure I'm pulling back to anything compared to the channel. That's all it tells us. So, because it's a DOS interface we get loads of stuff free. It's actually really easy to say this is the property, this is the property of the protocol. And so for advice, we can say the device has a protocol. It's a real protocol for the device with different mapping and associations. It's a protocol that we can enter. So here, the X on our main is used in the session to sort of be personal. I mean, there's a lot of stuff on the interface that we could have worked on. So, that brings to the point that it's just a slang, a lot of serial number. Maybe if we explore this this would work with broken device. Rebroken device is first, the name, simple in the session, and then the images, and second, we're doing anything over at the CIS layer, the second is the client. The protocol is definitely the same protocol as the other. The property is not really a protocol. So, I kind of published it. It creates a multiplier for this. First, you use the line of liners to have some kind of screener in three months. So, from this we can tell when the device was modified compared to where it created because that's based on three months that we can screen the snake. It's an approach that we've looked into in that scenario. It's similar with the lot of kit methods to break. So, we can add protocol devices. We can get protocol based on the sort of quality of the biography. We can make a protocol default. So, we can prefer protocol with protocol. And kind of more interesting about color of the object is the candidate methods. This is one of the core methods that say quality of the system. It can start off with color of the core device. Like in the sessions, it's trying to protocol the object. A protocol device will just set the protocol on an effect on the object. And that will help us to think we set the same things like the ECGT, the Econome, Table or any other printing that is an input protocol that we can't still present in the process. And then if the application that's been protocoled in, I know X is precious to it. So, whatever total or automatically time you are, doesn't force any of it itself. It's usually good when it's input. Either a protocol is set or it's that way before. Again, it can similarly be for a literacy constraint for instance, you can ask users to enter their own passwords. They do protocol in there. Or you can ask the root password for their trying to remove the profile. Or any local active users can do anything. SSA users can. If someone has physical access to a computer, there's more to the things that can be changed to the color of the monitor. So, I talked about calibration. And basically it comes down to what you can calibrate. For a scan device, scan device, it might be a case of thinking of proto or a scan device. It's a target. The target is basically very accurately a piece of card. Then there's a color swatch on it. And you start scanning it and take a photo. And then compare what you get as the tip output from the scanner or the studio level. Again, it's very tricky. Because with each target, it's a sticky, it would be exact sort of, exact color coordinate. So, we'll color them in that sheet. And basically, those things are sort of a way to see what happens in the RLC mode's correct protocol. It's a little bit harder to calibrate the display to need something like a calibration tool or a computer to have a pathway. They're about 50 dollars. You basically stick on the screen and RLC has a special screen that follows. We measure and it's a little bit less display to make sure that the protocol is correct. Now, there's two ways to calibrate the monitor. One is kind of easy and you go to one of the calibration services online. Now, while printing out samples of MMI and MMI to see if they can be longer than ICC protocol, that costs about 20, 30 dollars. It's quite a bit worth doing in the UF card to calibrate the total series of MMI's. Roughly, if you're a print shop, then you have six sets of 8 with six types of paper, but the cheap piece is by the $600 tool versus the monitor, which actually allows you to scan the printed samples themselves, get your first sample from the MMI source and actually continue exactly what the real type of characteristics of the test is. These are just three dialogues from the camera manager. They're kind of soft and you might have to do it online. There's no screen design guys who want to read work through the four positives. They're using this how a far-rear calibration process can be. There's no straightness inside, so it can change shape. The other kind of get better. Now, this all sounds kind of cool and I guess a lot of people think you understand the last thing that's crossed up. The standard is GPU built-in kind of like so. The library that we're coming to is Geo-type library. The LG we all need to gloss right away. Of course, a lot of people might want to use this with right-wing software. This is for the interface. You can actually take it to the interface with no people's analysis in words, which is kind of okay to use with right-wing software. But ideally, it's pretty old-fashioned. So, this is how you use Color D on the command line. The idea is most users don't know Color D exists on the user. The color engine of the command line only needs to be set up without the confuses and needs to be fixed up scripts or what do you remember, maybe it's a set or something. There are loads of commands to just get to places which is kind of condensed to be on the slide. It still shows information that you can get out from Color D. It's just that the first sort of lock of commands that you do. The device you're programing for, the device that's serial or the protocol set file on the main. So, it's just a very simple wrap-up allowing it to interface with the proper tool. I have a question about the previous slide. Now I don't have time. Go on. So, I'm used to using that for the last question. There's some translation needed. Oh, yeah. I don't know where I think we have all the questions. I'm used to it. Do you have any questions at the end? Yeah, that's fine. So, you're at the end. So, you're at the end of the demo. So, there's a few more commands. So, realistically, most people are not using applications and drivers that they're using Color D. As it all happens, I'm seeing this without knowing what's going on. So, if there's some new color, I'm going to use this color D to get primary. So, see if my request is sync. Turn to the point where we have some devices. If you're going to do a GLA and you're going to do a GX sync version of the GLA and some more good stuff, which is sort of that. Um, it's very useful. For something like the RStudio game or something, we need to export second state in RStudio, and we want to export photo data in the RGP color space. We don't want immigrants in any sort of random place on the process. So, this is a standard color based in the color space. I'm currently at the time, and I'm doing a color map. So, this is what we're doing with the dependency tool. We're going to use the sort of georgia dependency to use the model bus. It's a good thing because scope of the device that the program has created, so that it comes crashes, but we want to be focused and destroy things that the program has created. Now, no color major is really small front end because we do much talk, and we can match it to the color so it really just creates calls to create files to each other. First profile based on the ID class and coordinates. Then, first profile, which profile added, but basically this bit, and it's the best color of the work to match it, and it's the best for the privacy rules. So, profile added, we check the ID, the ID, the private, the data, to see which one is right there. We can use that if there's screens three months that way. We can also do the bus edit so we can load things like gantt.org or state buses. It's kind of like we understand anything about what a bus is. It's just a simple, easy matching just to get an extensive look at that. So here's some screenshots of no color major. It's just the interesting effects and showing the device on the top part and the effect on the bottom. So, the color rate button comes up in the sense to if there was a period work interface, I can change the profile to that. What you basically do is add color mix. Similarly, in gcbure, in more color mix, this is actually comparing and contrasting to profiles. So if you want more screenshots, just click on color mix to do the more color combinations. And you get information like profile, color count is like 3, whole, if you're at a table, you can say you're on a stand-in, show the image, click on that, it's for a certain beat. So, to recap very quickly, some of the most information you might have now, I talked about working spaces, color gamuts, ICC profiles, I haven't discussed how to combine which work flow, but key concepts and design choices are making color D. Then, as we use color D, be it from R9, blindings or digital emails, we talked about no color mixture. And also this KD version is how it's working. I hope to get this review with KD version for the next week. I'd like to make a thank you guys for supporting me with all this, because I just work on staff and I'm a bit more aware of it. So thanks very much for listening and I'll answer your questions. Thank you. We're looking at the fact that we're one question, dating. No, you answered it. Any questions? Okay, so I just want to make sure I understand this question with us and for us to develop and create a new one to graduate, and to add to the research into this. I've got a piece of this kind of information, and it's a specific one, especially with the best one. And I don't care whether I use it to use color, or to add to the stuff, I just want to be able to use it. I would have to use the wrong to use colors. I think that we're going to be using the bus, and it's really important to be able to use it. I will talk to you in a minute. Well, one of the benefits of this is that it can have all the languages and connectives. It's completely desktop-utual. It's a bit new to work in normal languages. It's a bit nice to be able to do that. But it's easy to read. What do you use, I expect? Color, color, color, color. Color, color, color. Color, color, color. Color, color, color. Color, color, color. Color, color, color. Color, color, color. We're going to have all the all the different options that we're working on for a while. That will be a big thing for people with color. I'm talking on the first page to get some interaction into the first two as well, and then I'm going to say hopefully this is not important to us. It's on very more than we do. Thank you.
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The colord project intends to make color management just work. In this presentation I will quickly introduce why color management is required, and also the problems introducing an integrated color management workflow. We will compare and contrast the frameworks commonly used in OSX and Windows 7. By discussing the integration points, we will be talking to application developers and platform maintainers in order to shape the future development of colord and the front-ends such as GNOME Color Manager. We will also spend some time exploring the intricacies of an open source color management framework best suitable for display, scanning and printing, and how we can start to provide this functionality. I’ll cover how key projects have already been modified to work with colord, and what application authors still have to do. There will be time left for questions and discussion. It is expected the audience will be moderately technically skilled, and possess a basic understanding of color management.
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10.5446/21672 (DOI)
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My name is Pete Ipple and I am not affiliated with open source software officially, but according to my name tag it says, I make art and share ideas, so I thought that would be pretty fair assessment. I was here for the first time in 2010 at the LGM conference in Brussels and I presented my own and some work that I was observing similarities between what I called the new folk tradition and that's sort of seeing a community of developers so you guys can consider yourself all quilters, each doing a little bit of quilting, you're making a bigger thing to keep you warm through winter which is the metaphor for your program. Anyway that was last year's talk, met a ton of people, super inspiring and so that kept spinning off in my work over the summer and when I was coming back from Brussels I was stopped in London and got a little Skype ping from the dean of the school at San Francisco Art Institute and it just said call me. So those are either really good or really bad. So I called her up in the middle of the train station and she offered me a position to teach a class called Making and Meaning which is a freshman foundation class at the San Francisco Art Institute and of course I leapt at the job and one of the things that Femke brought up the other day that I really respected is sort of that position of awkwardness or hesitance in art where you sort of know your tool but you don't know your tool and you're constantly in this state of flux of developing and growing and querying your network and that sort of thing. So what I want to do actually right now is switch into analog mode as you can see I have a pen, I also have an eraser. These are really simple tools. One of the points today is the complexity not so much of the tool but of what's running the tool which is in this case the dome, your head, your brain. Because it's got sort of a repository of all the experiences in your life and the influences of your friend and that sort of thing. When you get down to it it's all basically on and off, much like a computer. You've got a sodium potassium pump, you've got some axons, you've got some neurons, things are flying around and through its complexity there is simplicity. You can draw a line from the left to the right. It's really easy to just do like this, not so straight. So you go to art school and you learn how to make them more straight, darker, that means I pressed harder, different things like that. So there is a lot of complexity in simplicity. So the way that relates to art in the present is that with these complex tools the age at which people are accessing them is lower and lower and lower. So the generation gaps between a teacher and a student continue to get bigger and bigger and bigger because the rate at which the technology is changing, the generation gap gets smaller. So I graduated high school in 1997 and had no experience at all whatsoever with the internet. One week in August of 1997 I got a computer, I got the internet, I went to college all in the same week, very sort of exciting. I was dubbed P-E-I-I at Cornell.edu and instantly I had email and I still have it today. So very interesting tool set acquisition right there, instantaneous and then network community and all that stuff. So now that more people are coming I'm going to get you guys in full analog mode. So I want you to rub your hands together. I love to see that you're not typing right now. So we're going to do something crazy and try and clap all at the same time. So get up big and I was okay, we'll try it again. I'm going to get big and second try. Here we go, big, I was late. Not bad, here we go, one more and okay. So we're going to add complexity. So we're going to do three claps and then we're going to hold. So one, two, three, hold. One, two, three, hold. One, two, three, hold. One, two, three, hold. You guys are great. Now I want you to look around and see who you're collaborating with. We're going to try and get it even tighter and more complex. So this time we're going to be going, hey! So we're going to go one, two, three, hold. One, two, three, hey. One, two, three, hold. Got it? Okay, here we go. One, two, three, hold. One, two, three, hey. One, two, three, hold. One, two, three, hey. All right, getting more complex. All right, here we go. We're going to take our hands, we're going to get really crazy and we're going to pretend that we're running. So when you run you do like this but we're just going to make a little metaphor and that's run. Okay? So we're going one, two, three, hold. One, two, three, hey. One, two, three, run. One, two, three, hold. One, two, three, hey. One, two, hold. I messed up. All right, we're going to get it even crazier. Now this time we're going to add a zip, right? Just the letter Z. Zip. And then we're going to, what? Zed. Yes, for the Brits. Okay? So basically we're going in the same order in counts of three, hold, hey, run, zip. Okay? Here we go. Rub them together, get them ready. And one, two, three, hold. One, two, three, hey. One, two, three, run. One, two, three, zip. One, two, three, hold. One, two, three, hey. One, two, three, run. One, two, three, zip. Basically analog, think about all the things we're doing right now. We're having a conversation. We're doing similar activities. We're having a good time. We're getting a little sweat on. We're stimulated. We're aroused and not in a sexual way. We're just sort of up and awake in the morning. So this is basically what you want to be in in your life. You want to be activated. You want to be aware in a social context. All these things are super, super important for being a human. That's what separates you from your box on your lap. Now these interactions have been commodified in the last 15 years, because people love doing this. And how do you get the box to act like a human? Well, you stick another human on the other side of it, and you have a conversation through the box, and the box disappears. That's called transparency, or the singularity. We're headed down that way, maybe, where things become transparent. You don't really know if you're in or out of the network. It could be the matrix. We're getting close, 2035. There's been Ray Kurzweil, et cetera, making comments about those types of things. Yes? What would be the rate at 2036, 2036? Fair enough. Then we reboot. But that's exactly a very good point. We talked about that yesterday a little bit at the end of the talk, where it's like, well, what happens if things break? What do you do? And that's a great segue. So what I just shared with you guys is the joy of being a human. Now, if you take all that stuff away, what do you have left? You're dead, right? Or you're immobile, or those type of things. So after Libra Graphics, after I got the job, I was teaching students very much the same things about open source, about what I call the big four, and the defensible three. I'm just going to explain those to you and then basically show you a syllabus that I generated for that specific class, using some important points that you guys are probably all familiar with. So free and open culture. I wrote this in August. The job was supposed to start in September. What I was doing was getting it out into the world. People were making critiques of it. So basically, I just talk about what free and open culture is at one of the definitions. The ideas, the concepts of sharing, openness, decentralization, free access to computers and world improvement. I think we can all agree that those are some pretty amazing things. Those are not mine. That's sort of hacker culture from the 50s to 60s, and it's developed onto the present. I just put through some cultural figures up there. People, again, who you all know, which our students necessarily might not. But students are going to ask the following questions. I think the method is really great, which is called the variety of software. That's all you guys. The hands-on imperative. We essentially have been doing that a little bit, activating our bodies, doing the things. Essential lessons can be learned about systems, about the world, from taking things apart, seeing how they work, and using this knowledge to create new and more interesting things. How many of you guys are familiar with the term cognitive dissonance? Anybody know what that is? Somebody want to explain it? Not exactly. Oh, go ahead. Exactly. So cognitive dissonance is what you know and what your system does. Push into each other and you're like, blah, I don't know what's going on. That happens a lot with stroke patients. It happens with people that have neurological disorders, different things like that. And the great way to test yourself is use your boxes right now and look up something called the Stroop Test. You don't have to do it now. You can do it at home. But essentially what it does is it shows that through our educations, we get really, really good at certain tasks, and then we lose something that seems sort of human. So the Stroop Test, essentially what it does is you have a field of words on the screen and they're written in a variety of colors. In the first field, you have the color. So for example, let's say that this is blue, right? And we write the word blue, blah, B-L-U-E, in blue marker. Now unfortunately, all I have is blue markers. We were going to have a really fun time today, but they only have blue here. So let's pretend that this was red. And I write red, and this were a red thing. The task assigned to you in the first field would be all colors in the blue field, or blue would be in blue, red would be in red, green would be in green, et cetera, et cetera, et cetera. So this is actually a really good example because red is written in blue, blue would be written in green, et cetera, et cetera, et cetera. So the things don't match. Now if you take any group of people who are literate and put them together and ask them the task, what is the color of ink that I drew this in, people can just rip really fast right through a field of 20 things, maybe 10 seconds. The second that they don't match up and you say, oh, you're reading red, but the task wasn't to read the thing, it was to tell me the color of the ink. That's cognitive dissonance where you're like, and you kind of screech to a halt, you can do it, but there's two things going on. One is really deeply ingrained, and the other one is what you know you need to do. So in art school, you'll find a ton of people that are like, oh, image is worth a thousand words. That's not true. It's worth a thousand words when you don't have language and you have all this other conflicting information, and there's a strength that comes with images and words together, there's a strength that's there with just images, and there's a strength that's there with just language. So what I'm saying is that if you ask the four-year-old who can't quite read yet to do the same task, they're equally as good in both. They can do that, and you get clowned by a four-year-old, and you're like, man, that's really embarrassing. So that's really important, though, because there's a difference between one thing that I really want to differentiate. When was the last time you guys clapped together? That wasn't at the end of a presentation. You're like, yes, lunch. Well, probably a long time ago, because there's a thing that's called being self-conscious. Artists deal with that all the time. It's like, oh, am I going to look stupid if I do that, especially if you're in the performance art, video art, whatever. So one of the things I try to do is differentiate between the idea of being self-conscious and self-aware. So in that way, if you're self-aware, you're like, oh, my body makes these noises when I do this, that does this, it does this. You get familiar, you get embodied, your brain and your body start to connect, and then it gives you the freedom through the technique, because you start to understand that there are things like cognitive dissonance, there are things that are confusing, and that you're education has actually squashed your creative power in some ways. So the way out of that, first of all, is stop being a perfectionist, and that's what I love about coders, is that it's like, get it out there, let's see who can work on it, we'll show our ideas, we're going to take critiques, we're going to look at bug reports, we're going to go back out, and it makes an iterative process. That's one thing that I love, love, love about being in this community, is it's like, oh, let's figure it out, let's hack it, let's do this, let's do that, and that's a very creative act, so mad respect for that. One of the things that's also interesting that I found with working with programmers in sort of more of an art context, is the ability to have what's called divergent thinking, and that's sometimes beaten out of you too as a young person, and when things don't quite match up, people are like, oh, you're stupid, you know, if you're struggling with something, let's say you're a physical learner, you learn through dance, through movement, and you're sat down in a lecture situation looking at my head, then you guys might not be super involved. So one of the things going back to this that's super important in art education is getting people to think divergently. So I'm going to ask, you know, let's go onto Google here for a second. All right, Google images, all right, this is a great example. Okay, bathroom objects tool. What is this thing? Anybody? Okay, what do you use it for? Anything else? Okay, spring paint? Cleaning your bike. Cleaning the toilet. Okay, Barbie's comb, anybody? No? What other things we can use it for? We can use it for holding a window open. So this is the type of thing, what else can we use this for? Hitting a mouse, okay. Keep going guys, come on. Bike chain clean, we got that. You can make it into a bracelet, you boil it in water, it becomes flexible. What? Stir tea with it. Yeah, stir tea with it, okay. So how many objects, or how many functions can you get in an object? Kids are great at this. If you're like, what is this? A four-year-old will be like, it's a rocket! And nobody will be like, pfft! No, I didn't hear any crazy answers like that, right? It's not crazy. That's opening up that fear of self-consciousness, your squashing it down, fear of perfection, all these things. You sort of humble yourself, have the eyes of a child, lots of people talk about that in terms of Buddhism, right? Mind of a child's mind. That's really important because they have a certain energy that, you know, as an adult, gets kind of pushed out and squashed out and those things. So keeping that in your life not only allows you to be creative, but it allows you to sort of think really openly and to have solutions that are ridiculous for problems. And then you can be like, well, it's not that ridiculous because nobody's thought of it this way, so let's just play it out. And that's the thing that I'm trying to get these artists to be sort of like programmers in that respect where it's like, you know what, this is vaporware. Let's just brainstorm and get something that we want and see how many things do we know to get us there, okay? So going back to the syllabus, and we've been talking a lot about business models and a whole bunch of other things, right? Those are super, super important for artists, but unfortunately, that stuff is never talked about because there's sort of a romantic idea about the thing that you're selling out or you're commoditizing or whatever this is, and in reality, that's kind of what you're doing anyway, but the thing is the framework, right? So I try to encourage people to think like when they receive compensation, that doesn't mean that there are, it isn't free. Anybody can see it online. It's about licensing it in a way that you feel comfortable and thinking about that at the outset. So these are some of the questions that I've been querying my students that I think would relate to you guys. What are my artistic assets? What is my intellectual property? How does copyright apply to me as an artist? How does decision making, production, and follow-up inform my practice? How can I use goal-setting, affirmation, and planning to take to my advantage? What can I learn from business science and community? What are the concepts of a testable hypothesis, experimental concept, et cetera? And how does sunk cost and return on investment apply to my artistic endeavors? Now that may seem like a total mind blowout for an artist, but what the thing is when you take these metaphors and you apply them to art, they seem a lot like the beginnings of software development and that sort of thing. So basically by putting this stuff out here, you can say, okay, you're started using Photoshop when you're 14, now you're 18. We want you to think about bigger ideas in the future, not just what you know. And if what you know isn't that extensive like a professional Photoshop user where you're like super dialed in and doing little twiddles on all the sliders, et cetera, et cetera, there's probably some sort of program out there in the free software world that will satisfy your needs. And if not, you just need some more skills in a little tutorial. So that's sort of what I say is that, yeah, at sunk cost, you've already invested all that time in that. Grace is knowing when to nuke it. You just throw a bomb on it, blow it all out, reboot, and get your mind back together. So these are some other questions that I think are coming up now specifically in art too, is if it's not on the internet, it doesn't exist. I was told this by a 14-year-old. It's like, what? Like, no, I can just look it up on Amazon and get like 50 of them. Okay. But yeah, the benefit of it is that you can create everywhere. You've got a network in your pocket, which is your thousand friends and all this other stuff. So what it does is it frees you from the studio, which is something everybody's been trying to do, but it's tough when you've got a 40-pound canvas and a bunch of paint and a whole bunch of other stuff that you take with. But now these tools are small. You've got like an SLR, and I have the same megapixels five years later in this thing, and this is my primary camera, right? It's just a way of documenting and recording and, you know, live streaming, doing a whole bunch of other stuff. So basically, all of this was dumped out on the computer. I shared it with everyone, shared it with the students before, gave a presentation very much like this to them. And in the Art Institute, they have the option to select their own classes. They're in making and meeting, but there's seven professors to accommodate their needs, and they can go with whoever they want. And what's amazing is that you get kids that want to be in the class and care about the issues that you care about and empathize with you as a human being, as well as a teacher. So after doing that, we started working on a project called the physical word, okay? And that came out of the questions that I asked my students, is, who are you? What do you care about? Where are you going? How are you going to get there? That's sort of the long-term goals, right? And then there's the defensible three, which are essentially like most of these kids haven't been in critique before, so they don't really know how to defend their work. And there's three things that we have. We have context, excuse me, intent, context, and liability. And liability is an interesting one because it's like, am I putting myself at risk as an artist by appropriating these images and doing this type of work? Am I putting myself at risk physically by, you know, doing some project where I'm going to get run over by a car and then walk away? You know, am I putting the driver in danger? And then who is going to be having to pay to see that? Is it on the street or is it in the gallery? And I'm excluding a whole community of people if I'm charging for something when I live in a neighborhood that's very poor. So that's sort of liability in all definitions through the dictionary. Intent is simply what you're trying to show and provide context is the location, you know, gallery, street, whatever. So I heard a lot about, they care about their environment, they care about their friends, they care about traveling, they care about staying connected. But there was some disconnect in the sense that they still wanted to use the skills that they had before, which were painting, drawing, photography, filmmaking, video making, etc., etc. So basically what we were trying to do was sort of a, what I talked about last time was the push back to craft where you're actually using your hands and using the tools plus the sort of folk tradition. So what we did was we took analog and digital, smashed it together. And the physical word actually is the product of that. So side caveat. While I was going to Hawaii on a quick break, I got meningitis and cephalitis and a subdural empema all at the same time, which is a massive brain infection. I was out for 11 days. But because I had put all of this stuff on the web, John can speak more to this about what happened because I actually don't remember it. But he was at an art show in the San Francisco Art Institute and they were like, hey, can you teach for Pete? Well, he didn't know what had happened. But because of sort of being open and putting all this stuff online, he was able to gather the information and then I would have, there was two weeks left in the semester with the students. So they basically had two weeks of production. The outline of the project was already created. And he was able to, he's used to doing with fabricators sort of production work with a set of instructions. So he was able to step right in and then create this site with my students. So basically the premise was that we had this thing called what's the word. And we generated these signs and we put them out in the world and then gave away for people to keep back to us. And what we would do is that for making that investment as artists, we were able to then respond to that information and make something with the drawing, the printing, the video, et cetera, et cetera, et cetera. So we made these signs and we started to put them up all around. And then we started to get things, well, sorry about that, from the field. So once I threw up and there was a cat. So that was a tell me a story input from our output of tell me a story. So then what would happen is, excuse me one second, I have to find, where is it? So Ben started making responses and then posting them back on the web. So that's a guy in a little animated gif throwing up a cat. So essentially it was taking something from the field going to the students, the students going like this is hilarious or awesome or sad or whatever. And you can check that out on yourself. It's the physical word dot hyper modern dot net. And see what the different students come up with and then came back out. So the other thing is that this is a completely open project. You guys yourselves can just use 8 1⁄2 by 11 piece of paper, print it out, stick it wherever you want. And then that's a Google voice number. So it goes to it and whatever text they get. People can reinterpret them and put them back out, etc. So anyway, it's just really amazing for me having been essentially completely rebooted personally to lose all those skills and then to have someone step in because of the common tools that you guys have but bringing that to the art world and then having the project still produced on schedule in a very happy way. So I just want to show one last video and then I will let you go because I am actually five minutes over time. Actually I won't do that. I'm just going to end it right here. So are there any questions about the project and sort of what my teaching style, etc. are or do you have any questions? Questions anyone? All right. Well, thank you for your time. Oh, yep, we go. And if you want more of this backstory and stuff, you can just contact me offline here. So how did the artists react? Was it an easy transition for them to? Okay. Because I'm just early in the morning, no coffee yet. The idea of the tools and process and we kind of went into this a little at the studio XX thing. Sure. But how was it for the students or how did it seem perception wise? Did many of them end up using free and open source? I saw that there was sort of like an emphasis or with a strong consideration but there wasn't a requirement. Right. Okay. So that's a really great question. My sense of it is that everyone who's coming into art school now has some experience with image generation digitally. The depth of that makes it that transition harder. And one of the things as a teacher is to be super empathetic because if you yourself know the proprietary software, you can sort of act as a translator. So you can say like, okay, what can you do in Photoshop? And they will show you like this is how I do these things. And then you can say, okay, well in this program you can do this and I can show you more on this and then in addition, you basically tell them the facts that the second that you get out of graduate school or undergraduate school, you have a couple options. You can pirate the software. That's your choice. Right. I'm not going to say yes or no. That's completely up to you. You can purchase the professional version, which again is their choice whether or not, or you can join this community and be a part of the development of your own tools and this, this and this. And freshman 18-year-old art students are pretty open. They know they're going to be in for four years and that if they join this community, they've got a whole other network. They understand network effects. They understand these things. And then just on principle, a lot of them make the choice. These are things that I want to do at home and they might not have the stuff installed at school. So at least at the Art Institute, they at the time still have all the proprietary software, but the thing is pretty much everyone has a laptop or some device that they can create on their own. And so you can just advise an install or you can say, hey, check this out. Hey, check this out. There's four different drawing programs. You've got ones for pixels. You've got ones that are auto generative off of groups of numbers like node box is a neat thing to try. You've got Inkscape, GIMP, Krita, all the other ones that we know. And so they're very receptive to that. The idea of choice is very appealing to anyone a lot of times. So that's how I frame it. And then the idea about sunk cost and return on investment is very much a clear thing. It's like a lot of times you get out what you put into something. And artists understand that. It's like if I spend 20 hours doing an oil painting and then put it up in an oil painting critique class, they'll be able to see that I was glazing it. They'll be able to see that I was really concentrating on the underpainting and this. Whereas if you sort of fake it and you're like, do something really quick, it's still wet when you hang it. You know you didn't put in the work and the professors know. And so you talk about what's there, but it's not really the same. And I see that sort of as the difference between running to Photoshop and throwing in a photo and doing 15 filters and being like it's an abstract work versus saying like I'm doing path editing and this is a generative piece that I made from Nodebox and then ported it and did, or not ported, that's the wrong word, but exported it and manipulated it and did this and this and this. And then as those processes become more embedded in the artist, then they have the flexibility to really blast out and open their minds up to bigger things. So yeah, at some cost it's like, well, I lose the 10 hours that I spent learning Photoshop, but I gain a community free software for the rest of my life and a new way of thinking. So glad to hear that. Yeah. Hello. Yeah. So one thing I find kind of interesting again, like art students and people kind of working on my creativity, creatively like that is like the idea of controlling their own tools. And is there many of the kind of students coming there who like don't really have the concept of programming that kind of get inspired to like CD like possibilities of being in control of their own kind of workflow, and even like realizing that if they really want to do something, they actually have to dig down and become rather kind of technical to enable kind of expand your horizons. So the good news is that there's a lot of schools that are encouraging people to hack, both physically and in code. And the tools that are used mostly are little controllers that you go from like USB out into a controller, and then it's got a series of ports that you can plug different items and things in. And there are classes offered in that specific like hardware hack. And then there's also classes more orientated towards like what's called circuit bending where you crack something open and you try and make your little keyboard, make funny noises by just soldering up whatever you think might work. And then along that process, at least at the Art Institute, the way things work is you do a lot of like free form exploration, and then you do like student nudging where it's like, oh, I see that you're sort of experiencing this. Wow. How about this or this? And then you sort of keep letting them make choices along the way. And regarding coding, I think there's classes in processing, which is a little bit easier, I think for a lot of people to make the transition between like straight command line stuff. So you can like test things in like a visualization thing and make aesthetic choices, and then it kind of writes code back in. And the visual, like the physical outside of the body versus like your substructure, like your bones, is very much how I would equate those things. And so it's like, they need to see both because they're not just making like coding choices. They don't have the capacity to do that until they get far enough that they say, OK, I understand how this works on an aesthetic way, and now I can make these choices without that because I know what it will provide. But that first beginning part, they really need visual stimulation. And then there's people that have come in with coding experience. Usually it's HTML or like some JavaScript stuff or ActionScript or things like that. And they have more of them. They know how it works, so then it's easier to teach without the visual. But since I personally don't have that experience, that's not my field. I'm more of abstract thinking, long-term thinking like business, that kind of stuff. So you talked about how you get your students to enter into the community. Are you encouraging them to be participants in the communities for, say for instance, the GIMP or Inkscape? They may actually be able to influence development and report books and help. So the way that I see that, my role in that, is just encouraging participation. It's usually feature requests and those types of things. It's like if you don't see this, you can actually ask for it. I don't know how that's ever worked out, whether or not it's actually happened. But that's usually what I do. It's like, what can you contribute? In my own personal life, I'll just speak to that. The way I support open source is probably like $10 or $15 at the time. And it's usually for someone, like again, my phone is really important to me in terms of photographing and stuff. And unfortunately Nokia doesn't support Linux. And there's a kid somewhere in Europe that, you know, he has a tool where he plugs it in and just syncs it automatically. Like that's really important to me, so I help the development that way. And I encourage things like that. Like if you want. That's what I meant to say, excuse me. Because Nokia themselves actually did a whole bunch of Linux development. Sure, excuse me. Yeah, again, the program part of it. But to just go back to your question, the other thing that they can do like services like OpenClipArt and things like that, sharing is very much a culture now because of the instantainity of it. So that's not going to change. It's going to get even more instant and more remote so you can be out in the world. And I think that part of being an artist is really cool. It's like, hey, check out this drawing I just did. Snap a photo, send it out, do it that way. So I can see that if features were added to image editing software where you could be like export to X social network or export to Ping FM and blast it out like a shotgun shell across the whole internet, that's awesome. And that'd be a really positive thing if you could add meta to that like the author and then like write exit data on whatever you put in. Like that would be a super useful tool for artists because you'd be able to instantaneously get things from your computer wherever you were onto the web with sortable data all in one simple export. That would just be amazing. And you could even set up like upload rules that would say like, hey, go to OpenClipArt, go to this, go to that, and it would be happening real time. So as a developer you could see like, oh, what tools are they using? What brushes are popular? So yeah. I think we're over time. We'll conclude with this. Okay. Thanks guys. Thank you. Thank you girls. Interesting. That it was so much fun. That was fun.
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LGM 2010 was a new experience for me, and has greatly influenced my teaching, my art, and my perception. While I was in London returning from Brussels, I received a call from the San Francisco Art Institute to teach a freshman foundation course titled “”Making and Meaning””. It was the first time I had the opportunity to create my own syllabus for undergraduates, so I chose to teach about free culture, and how create work and consider open principles when executing projects. Three weeks away from the end of the semester I was struck by a nearly life-ending infection. A fellow free culture advocate came to my aid, teaching in my place, and helped to produce and inspire a project called “”The Physical Word.”” In this presentation, I will share my story of how the principles of LGM serve as inspiration to recovery and regrowth.
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10.5446/21674 (DOI)
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Okay, so actually as a professor, in all my different roles I try to convince people that programming is like a really neat thing. But there are some intricacies to that for people who think visually like designers and I'll go into that. And this is a little like, this is a wonderful quote I think to open with. It's from a very interesting little post by a certain man named Rand. The thing is with free software there is no really rigid distinction between the user and the developer. It's like a continuum between the two. And I've been reading this interesting book recently from which I completely agree with that to be like a literate citizen in like this century you'll have to know how to program or at least how programming works or otherwise you'll be programmed. Like the logic of the not necessarily machine but the logic of the other people programming will be forced upon you. But then like one thing people tend to forget like when you want to learn programming or teach programming. You know, because when you know programming things like okay it's quite easy. It's like loops and variables and functions, there you go. I mean you can learn that in a week. It's like super easy. But that's not really what programming is all about because, oh that's the last slide. That doesn't make sense. Programming is actually like also embedded in a certain culture. Like you could call that deep culture but I'd like to refer to it as programming culture because that sounds less derogative. And you cannot really like, people like tend to feel the use of programming unless they also get to understand and be somehow part of this culture. But when you're learning programming you're faced maybe with some of the biases within this culture. And if you're like programming yourself and you've learned all these things you're maybe not as aware of this. But the most striking one which I wanted to have a little light, shine a little light upon today is this bizarre preference of programmers for plain text which is really funny in the context of graphics because graphics are not plain text. No? You have to call us about it. You have to call us about it. For example, and that's not really plain. Like, I mean, like, who do you think this quote is from? Yeah, Richard. So, the thing is that this doesn't really resemble how most people use the computer or how most people think of their interaction with the computer. But, like, funny thing is that there's sometimes like this nostalgia for the time before the graphical user interface. So from this book by Douglas Rodgka, he sort of describes like, okay, when you're just faced like with your console and you have like full control over the computer and everything was so much better back in the days. But, you know, you can sort of tempt me to maybe forget that back in the days he says, those of us lucky to grow up here in that short window of opportunity, but let's not forget that back in the days nobody used the computer. I mean, like, only like highly educated white people like Douglas Rodgka would do something like that. I don't know. Actually, most people started to use computers not very long ago. I like say like maybe like 10 years ago they became ubiquitous, like after Windows 95. And actually, so this is something that I think, like, this is sort of good to keep in mind when thinking about like things like graphical user interfaces, they've played a very large part in making the computer accessible to all the people that are using it now and that are contributing to like the vibrant white culture. But like a nice example of some like, for example, like when I try to make programming culture like more like to to to to indicate people to it and explain how it works. This is like installation procedure, but no where it explains where you would actually have to type this. First you have to like go to a console, open a console and type this and then run enter. And these kind of things are maybe so super used to, you know, what else would you do with a line of text and open a console and run it. But these kind of kind of things that I, you know, I have a hard time explaining to people. Like, let's just say there's nothing wrong with using the console, using it, but you have to be aware that this is something that will not immediately be apparent. Like, for example, this, I mean, I really like looking at this home page, you know, I was super communicative. They've made it like they've made it like they really tried to make this speak to you and make it like concise. But it takes quite some like for knowledge before you understand that this is actually a Ruby file. And then what you do in here is you're opening the console and you're running this Ruby file. So let's just say like it has to come, I suppose both ways. Like I try to tell all my students like, you know, every business program is like a little text file. The program is locked up. So please try to understand that if they tell you something like this, they're probably talking about putting it in a text file and then running it. But at the same time, like if you're already going this far and you're trying to be communicative, you might as well like go to route and explain a bit more. Like I'm in another life, and that's misunderstanding I had the other day, like with them to bear both who like, put some other people like CSS. And they have this thing where like, we can't make CSS like all complicated with variables and things because it has to be really easy, like has to be able to be used by everyone. And I was like, yeah, but typing in like text commands into a text file for most people that like a huge like is like programming. They feel like they're programming anyway when they're going to type things into a text file. So the amount of people for which something like this is easy is kind of small. So these are some nice like little cultural things. One like example which I wanted to give which was like different, like maybe the difference in thinking from code and things from a visual perspective. But when you think like look for example at some like CSS, that would form a contact separator, that like William Morris, when he would, when his printing proof would come back from the printer, he would like spend like all his time to make sure it would change his text so that the letters, the distribution of the letters upon the page would look like the best. And I know like many graphic designers who copy edit their text to fit the image that they're trying to make. Even if the client doesn't know. Can I sneak this in there to make this look better? And this is like working, you know, so this is like you don't work from the end of the text, but you work from the end of the image like different proofs. And how does that like reflect upon your interfaces? Like if you were like a programmer and you would think of interface to make things, you would probably have a little text file that makes them. And actually when we try to teach programming to artists, we do like the same thing. Like make this is processing, so it makes little text file and it generates escape. And I showed this and one of my students said, you're betraying us. I was like, what? I'm betraying you. He said, well, you're doing it the way of the programmer. Like you're writing the text and then it sort of appears like that's completely derelict. Like why can't I just start to drag on the image and then the text changes. And was my whole fair point. Because it's not like that's impossible. Because if we look at Inkscape, this is like super nifty, it actually goes both ways. So you can change the text of the XML file like live in Inkscape. And then you will see the path change, which can also change the path and you'll see the XML change. And I think somehow thinking about future interfaces, that's really where we need to go. Like because code is essential to the way computers work. So you can't ignore it. You can't have this 1990s dream way for interface which sort of splits out like super unaddisable, ugly code. Because code is important to the way computers work. But at the same time, it's like direct feedback that a graphical user interface offers. It's something you also really don't want to let go of. And like, yeah, maybe that's a bit of an obvious point to make. But it's just something I thought I'd share with you. And actually, nice thing is yesterday I was at the Python meeting. And there's going to be a talk later about Blender and Scripting Blender, I think. And here they really went all the way. Oh, here he is. And that's like, they did this super cool thing where when you do something, when you do an action in the graphical user interface, for example, you play something on the scene, then it's been logged. All the things that happen are being logged in Python, in the Scripting language of Blender. So it says, OK, place this in here. And you can copy this to the band, and then you can put it in a Python script and run it to, well, execute that again. Like, for me, I was like, that was really something. Or you can see a command and at the same time see what it is in the Python, like where you see an object and see where it's located in the Python dictionary, like the data model. These kind of things where code manipulation and the interface are like a bi-directional kind of thing. I mean, I'm really looking forward to seeing more of that. But then we have to let go of this idea that sort of that's the end-end be all of manipulating content. In the case, I think. Yeah, like JavaScript, the nice thing is like now because it's coming on the front end and the back end, like you have the content editable thing in HTML5 where you can just start to randomly edit a web page. But then that really doesn't go back again into the HTML because it's front-end. But with surface-like JavaScript, you can of course start to make these things actually per faces. So that actually changes the page. And that's also something I'm looking forward to to see more of. Well, that's it. Like, maybe not necessarily questions, but also maybe ideas, I suppose. Okay, so, last question. So do you have any idea of how to have a direct manipulation interface to a computer to do a loop or to use one rival? Yes, sir. You have? You have? Great, you have. There's a graphical programming language called scratch, which is becoming very popular. It was originally made for teaching children somewhere between the age of 7 and 14 how to program. But it's actually being used by a lot of universities in computer science curricula to teach programming in the first three or four or five weeks. And you learn a programming language based on text. So you can find out on the web at scratch.mit.edu. And I have nothing to do with it. I just think it's pretty cool. And I thought your presentation was also really cool. And, yeah, just, will you really emphasize the interplay between, you know, the trail moment? Well, of course, the graph interface should inform the text. The one thing in my life that I do that's like that now is in Firebug, I sometimes edit the CSS for the document live. But then I copy it out of Firebug into the actual document. But back in 1994, I've been using Word Perfect with reveal codes. And Word Perfect with reveal codes was very much like what you described if you, if inkscape, where you modify the document and it changes visually. And it's an amazing thing. Like, I used to teach a course to, like, well, I want to say elderly people, that's not really appropriate, but, like, not so young. And I would say, like, HTML, as explained, like, okay, all of you Word Perfect, you'll know this, like, screen, you know, with these codes. It's the same principle. And they, like, they get it, you know? And actually, like, I know people are still nostalgic for Word Perfect because Word sometimes has these, like, when it goes, like, oh, weird on you, and it's like you do an enter and it goes somewhere, like, why does it go there? And I mean, I speak to, you know, people who have to work in an office and they use Word Perfect, like, with Word Perfect, which is like, go in and I would delete the thing that was bugging me. So this also goes to show that, you know, these kind of interfaces are actually, like, to a wider audience, also accessible in that sense. No questions? Okay. Well, thank you. Thank you.
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As Douglas Rushkoff explains in Program or be Programmed, programming is a new literacy that ought to be mastered if you care about taking a part in directing our culture. To those who already program, it can sometimes seem odd that the number of people learning this vital skill is so small: after all, basic programming is not very hard. The catch is, programming as a skill is deeply embedded in a larger ecosystem, referred to as programming culture. To learn how to program is not just to learn how loops and variables work, but also how to navigate this culture. Like any culture there are biases in programming culture, and these can make learning how to program more difficult than strictly necessary. As a designer, there are certain biases that are especially remarkable. One of them is the way how text-based interfaces are in favour: Whereas everyone else is traipsing around picking dazzling fonts to describe their world, your nerd has carefully selected a monospace typeface, which he avidly uses to manipulate the world deftly via a command line interface while the rest fumble around with a mouse. This talk will highlight a number of ways in which the text-oriented view of traditional programming clashes with the visually oriented way of thinking of designers. It shows how text based thinking can enhance a design process, but also goes into how a bias towards text-based approaches can stifle the development process of software, and make programming less accesible to new audiences. It shares lessons learned from the process of learning to code as a designer, and subsequently teaching code to design students. It concludes with how developments in Libre Graphics software can mitigate between these two paradigms.”
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10.5446/21677 (DOI)
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Anyway, I made a presentation last year about an idea for some software that I felt had a reason to do this. I wanted to make some creative clothing and sculpture with fabric, but I didn't want to have to buy expensive pattern making software. I thought, well, I'll just make my own because I could see what they were doing, how they were doing it, but I didn't want to spend thousands of dollars. This is now a year since I made that first proposal. My background is in computer networking. I could pick that stuff up last night and haul it into the kitchen because I've been hauling Cisco and Foundry routers for two decades. I also learned how to sew for my mother and grandmother. I had talked to my husband about it and he talked to John and they had obviously beer. It says so. So I came to you guys to talk about it. I wanted to be part of the open source world. Since I didn't like the pricing of the software I was looking at, I thought, well, why have it low price? Let's just make it open source. Let's go for it. Steve suggested, well, let's go for open file formats as well. That's equally important as the software itself. We were also interested in being part of, not just reclaiming our tools, but reclaiming our Earth. Reclaiming our identities as humans, reclaiming our self-sufficiency. And also, we want to be able to make clothes. So I came here asking for people who would like to help me develop, help me write programming. Of course, everyone has their job and they have their open source project. So I realized if this was going to get done, I was going to have to do it. But a lot of people got it. A lot of people really understood what it was that I was asking for. So after my presentation, I had a lot of people come up and suggest various ways in which we could accomplish this goal. And one of them, Doug Shappers and John, a few other people said, you have to do this in SVG. This really, I think, is the way to express and shape these patterns and then make them respond to customers' measurements. And I've been a little active on the create list, which helped keep me going through the year. So during the year, I taught myself Python. I learned some Inkscape. I talked to a lot of people that I've never met before and bugged them with email. Please help me. And I realized, ah, I really have to get so deep into this stuff. Because as we say, there's not enough developers to go around for our projects. So along the way, as I was learning how to do this, I thought I can teach other people how to do this too. So if we want to have our open source projects, maybe we need to create our own programmers. Get these kids in high school, get them an application, a real world application to work on, get them some open source operating system, open source programming tools, and a real world problem to solve. That has some aesthetics to it. Or something they can relate to. So I'm in the middle of putting together a 501c3 program to teach Python through pattern design. So I had this background, you know, learning to program with punch cards, because I'm sure I've told every single one of you about it. So I'm very procedural, you know. And I got it working, it was really great, but the code was massive. So I handed it off to Steve in November, and he converted it into object-oriented functions and separated out the engine from the design, which is what we wanted in the first place. So that I, as a designer, can make a file as a formula of my design. And then shove it through an open source engine and come out with a design that belongs to me. But the open source engine is open to all. It's like Inkscape, you know. You make your design, that's yours. You sell it to your customer, or you enjoy it yourself, whatever. But it is yours, it belongs to you. So we were able to abstract the engine, the data. We were trying to come up with licensing modes so that everyone understands that a person's file, a formula, is their property. You know, if they wish. They can sign it over to, you know, create the comments or something if they want to. But if they wish to, they can keep it as their proprietary. So everything that we've done has been written in Python, and my husband added PySVG. And that's a project that had kind of lain dormant for a while. And since Steve's been talking to the guy that does SVG, it's sort of getting a little more polished to it at the moment. I'm not sure how much change is happening, but there's some dialogue there. So that might be the fact. Because it's really at its base. It's definition. It's a really good package. It's a nice library. We're storing the data at the moment in just a flat JSON file. And that should be converted into a full-blown database in the future. We've converted it so that the data and the pattern structure are hierarchical items. You have your client, and then you have all their measurements underneath the client object. And then you have the pattern object, and you have, you know, like a jacket. And then jacket front, jacket back, jacket sleeves. And then seams underneath that. And when you look at the code, if you look at the XML of the SVG document, everything is given an appropriate ID as well so that you can go and find a certain spot and make change. It's not that we don't allow the random IDs that are generated by 3Escape or 3Python or through an SVG engine. But as I say, it's really just a, you know, we're not there yet. Still kind of a second stage prototype. But it does look like it's going to work. We're pretty happy about that. We'd like to find two part-time developers. There was a guy through OpenHatch who volunteered. They're in, I think, the Netherlands somewhere, and they're into blender and fashion, and they're in some art school, and they're very excited and young. And I'm like, oh, what do I tell this person to do? So once you get a developer, what do you do with them? So think about that. Yeah, but they seem very enthusiastic, very enthusiastic. So I've got to do some software engineering now and actually do some management. So, and the workshop on Saturday was a lot of fun. I kind of had, I've been learning Git, and I submitted the wrong pattern to my Git library. So when I, when I read, you know, updated my Git locally, my repository locally, I pulled the wrong pattern. So anyway, I am learning Git. I left that out earlier. So next year, we're going to really push hard on the nonprofit efforts to get this program into schools. I've been talking to people at Alabama, at the University of Alabama in Tuscaloosa, which was sit with tornadoes recently. So I think maybe they're not interested so much in talking about it right now. They have bigger things. I've also been talking to a college in Tennessee, Murkreesboro Middle Tennessee University. They were, they have a Girls in STEM program, and they are very excited about putting this in place. So I have some mentors, and the mentor shops really, really interested in getting this going and getting it going quickly. In addition to that, we want to develop the STEM alone application for, you know, beyond the basics for the STEM program. We want to keep it going and make it more useful to the industry. And I do, I think I can find some early adopter designers. There may be some in this room that I've talked to several others. There's a guy in Australia that makes swimsuit patterns and some people in Oregon. So I think there are people who are interested in it. And of course, if any of you want to volunteer your body measurements, email them to me. I will use them. And because so far I had one data set which was mine. So when we changed data sets on Saturday, we sort of thought of problems as well. So I need to expand that. I have a little more. This is, I'm going to get into some revelations on how bad a programmer I am. I'll show you. The next one is. Okay, again, that's my stuff. This digital pattern making, I create block, at the moment, most people create their own patterns by creating like a boxy block basic piece. And then they, they curve it up and rearrange it into different shapes. Or they copy an original pattern and just slash and spread to meet their measurements. Or they draw using a formula, which is like a traditional tailor approach. Where you train from when you're seven years old and you learn all these different formulas and different types of jackets, different types of pants, and it's a lifetime investment of your brain. It's very difficult to do. You can't, you know, you have to be very smart to do that. And what I'm really aiming at is preserving the tailoring information. It's something that's dying. And I think that if we can just get these formulas into these programs, they won't disappear. There's a lot of information out there. So, so, Tomatotel Fusica is an attempt to give you the tools to pull, you know, what's in your head through a GUI that has yet to exist. And use these methodologies that my husband and I are creating right now to produce patterns so that you can create your 3D shapes, whether that's garments or sculpture or whatever else that you have in mind. So that's sort of what we're into. Right now, using Escape 4748 is what I've been using. I've been using the Eric Python IDE, which I love, and Git, which I'm learning. I've made mistakes, but it's great. Now, I'm sure all of you know that when you make an Escape extension, the first thing you have to do is write an INX file, which is just a hypertext file. And at the end of it, you tell it which Python file to call. And you can say parameters if you want the user to input information. That's where you put it in the INX file. You also state which menu you wish for your extension to appear off of. So, you know, I'm not sure if you're aware of all that, but I just wanted to tell you that. So, if you wind up in a video, maybe someone will see this that doesn't know this information. Also, extensions can be effects or filters. A filter doesn't actually change the file you're looking at. An effect does. It permanently changes the file. So, add TMTP extensions considered an extension. And it should show up in your extension menu. And SPG documents are also text files written in XML. And when you create an SPG file in the Escape, it automatically adds... If you're learning SPG, you learn all this other stuff. It's going to have...it's very picky. It's got to be precisely the standard or it can't be read by an SPG engine. So, you have to have the right header data. You have to have the right versions. You have to include the correct pointers to the data, you know, data dictionaries. So, all of this is added by Inkscape. So, pushing this through Inkscape is sort of an easy way to get all that into your file. So, your Python file doesn't have to write all of that itself. So, there are some good tutorials on this. Of course, obviously, on the Inkscape Wiki and also the SPG commands at w3.org. Those are great places to get in commission. But I didn't...I knew nothing about Python. So, I understand that variables are really easy with Python. You just write the variable name and you give it a value and then the variable exists. And it has a type. Now, you can't say age is 12 and then age is a character 12 and then age is a float. You can only do it once. You can only define a variable once. So, it can be, you know, any one of these three. But you can't...once you give it a value, then it has a type and you can't give it a different type. So, that's important. Objects in Python are complex. They can hold the simple variables. They can hold other complex objects. Now, this is what I call the magic init. When you create an object, you make a call to this magic init in Python. And it creates the object and it also adds some default functions to it. One of which is the affect function which causes the program to execute. I knew nothing of this. There's very little documentation on this part of it. So, it's the magic init. So, some object examples. This is my favorite, the generic. I can do anything I want to with that. I just created an object. I have a function, definition, def init, self. So, it can refer to itself as self within that class. And in return, it has no default values, nothing. It's just a variable that can hold anything. But here's sort of a dumb example. And again, I'm trying to make it at a level, maybe a seventh grade girl could relate to. So, we're going to make some snow whites. Class creates no white, right? No parameters passed in. Nothing, doesn't need anything. So, we define function and we call the magic init with self, why we don't know. And then self.hair, oh, snow white has black hair. Her skirt is yellow and she's about 15 and a half, right? Something like that. And then return. So, this is all it takes to create snow white at the moment. So, in our program we have snow one. We want to create snow one. So, we call create snow white. So, we create object, oh, let's create another one, snow two. We call create snow white. We have two snow whites, different names. Snow, we can just add variables if we want to. We can tack it on there, it's just an object. Snow one dot, she has a sport that she likes. And it's lacrosse. Snow two doesn't like sports, she likes video games. Her favorite one is Lord of the Rings. Snow two also has a baby. She's a little young, but she's got a baby. So, and it's a baby boy. So, we're going to create a baby boy. Here's the class, create boy child. It's, they have the function, definition of emit to create a class, an object. And the gender is a male. It's a boy. It's just a baby and a boy. We don't know its name, nothing. So, okay, the babies, we're going to tack on just a plain variable. And it's a govindu. It's the boy's name. So, in my program, this is what I do. I use the generic a lot. So, if I have a starting point A and a pattern, I just say A equals generic. And a pattern, pretty much you visualize on an XY grid, just like a video game, X being to the right, Y being down. Say A dot X is 15, A dot Y is 100, and the ID of A is A. So, when you get into the SVG of it, you can format your SVG commands with those values. So, if you're going to create a rectangle in Python, you define something called genre rectangle, and you say self, okay, because you're within Python, you have to tell it to act on within your global context that you're in at the moment. And in my layer, in Inkscape, you're always in a layer. So, and you can have to find different layers to write something to. An X, a Y, a name, a line color, a fill color, a line width, and then how wide and how high. So, you define these dictionaries. So, my style, I'm trying to write this to make it obvious that this is a variable that I've named. A lot of the resources that I've looked like, it'll say style, equal, all of this, and attributes equal. Because, well, if you give the variable the same name as what it's supposed to be, it's a little confusing. So, I just want to make sure that you know that my style, it's a variable name that I made up. I could have called it George. But my style, and then I define within brackets, the stroke value, the stroke, and it refers to the parameter, the stroke width, and it refers to the line width. And obviously, line width is going to be a number, because I have to convert it to a string. SVG is all text. It's 100% text. All variables, all parameters that you pass to it have to be text. So, you convert all numbers to string. And then there's a fill and a fill color. Now, there's an attributes aspect of this to create an SVG command. And the attributes, you know, the style is more like CSS styles, right? Sort of look and feel aesthetics. The attributes are the values that actually create the shape, the center of the object, and where you're going to start, how wide it's going to be, what the radius will be, things like that. And also the ID name. And this is, I've paid a lot of attention to the naming in my program, so that you can look at it, know where you are, if you have a problem, you can go back and fix it easily. So, name, and then again, x will be a string x, y. Even the parameters are in our strings. The y value for this rectangle where it starts is a string of the y that's passed in. The width is string of the width value, and the height is string of height. And then there's the style variable, style parameter. It uses the library of simple style to format with its command format style on my style. That's a little confusing, but it takes this dictionary that you've defined, my style, with all the CSS values, and wraps it up inside an attribute string, and then inkx utilizes this eTree engine to create elements. So inkx, eTree, subElement, and then you tell it which layer from your parameter, and then the inkx, again, with its command, add a new subElement. And oh, it says rectangle, I have a circle. That's my programming. So anyway, that should say rectangle, SVG, and then MayaTrips. And then MayaTrips is this dictionary here that has rolled up in another format, the style. So everything there is rolled up to create a new subElement for a rectangle. So in my program, if AX and AY are 100 and 200, and the ID is A, and the self, draw a rectangle, will add a rectangle to my canvas, to my drawing. And my base layer is what I'm calling, just, I don't have a special layer at the moment, just the base layer. And then A.X, A.Y, and as you see, those are numbers, so convert it to string of there. And A.ID, which is string, doesn't have to be converted. And then green will be the line color, the stroke. Orange will be the fill. Seven is the line width. 75 pixels, if you don't specify anything else, it's pixels by default. 75 wide and 50 high. So that's what you have to go through in Python to generate an object. And within the SVG file, it looks like this. This tag, this hypertext file, rect ID equals A, X is 100, Y is 200 width, 75 height, fill stroke, and stroke width, slash. So that's kind of where you have to go to get here. But, you know, it's really worth it because we get so much the total control of creating a pattern so that it can be manipulated through user parameters is really cool and it's been worth this effort. Again, as I said, the Inkscape extension files are INX, and these tags are meaningful to Inkscape. User inputs are declared as parameters. You state where your menu goes and you state which Python file is called. Now, I've got an example to show you. If we have time, probably not. But if you want to see my code, I can show it to you now or I can sit down and talk. Alright. Okie doke. And I really do like Eric, this Python IDE. Try to get it to be visible. Let me pull up the INX file first. Ok, this is all it is. You just say, ok, this is an Inkscape extension. This is the first tag. And then you give it a name. You can call it anything you want to. But that's the name that shows up in the menu. FrontBottice. And here's another ID. Tntp.frontBottice. Now, this ID can show up in listing of extensions for Inkscape. I could call it tntp.susan.test.frontBottice. whatever. And that's purely up to you. It's not meaningful, but if you want to see your things listed in Inkscape extensions in a proper way or an organized way, you'll have some organization of your extension ID. So this is an executable. We want this to be located in the extensions directory. Like in Linux, it's off your home folder. It's slash.config slash. Inkscape slash extensions. Windows, I'm not sure. So we're dependent on Inks and symbol transform. So we need those. But those are, fortunately, installed with Python now. And here are the parameters that I've defined that we need for this program. And some of these I'm not using, but they're still defined here. I don't want to take them out. Next circumference, shoulder width, front armpit distance, back armpit distance, buster circumference, bust point distance, bust length, front bodice length, back bodice length, waist circumference. See, all of these are floats. The min is 1.0. Max is 1,000. Now, this didn't want to leave anybody out. So you have an upper hip circumference, a lower hip circumference, and a side seam length, which is just from your armpit to your waist. And then there's, you can put in some help. What units are you using, metric? At the moment, I think I'm using, for this, I think I'm using inches. I do have, I played a lot, so I have a lot of these different things going on. I have one where the parameters, where I have an option, parameter option, to select centimeters or inches. But this is not one of those. This is just a really simple, really simple one. And here, okay, so we finished, we declared our dependencies, we declared any parameters we want the user to put in. And so now we start saying, this is an effect. This is not a filter, it's an effect. And object type all, and I don't know what that is. But I should find out. But I know it has to be there. It's going to go in the effects menu and the submenu name. So when you click on the effects and you go down the list of options, there's going to be a submenu name called mine. And then slash effects, so you've told us which menu is going to go in. So that's the end of that tag section. Now script, here's where something gets called. The command, the relative directory, is the extensions as I told you, that's like slash your directory.config, inkscape extensions. So that's what that means. And then the interpreter is going to be Python. I mean, you could have Perl or some other program, but this one's Python. And this is the file to call front-bottice.py in command. And then in script. That's all in the next file. Now then, the actual Python file, you know, you kind of want to say who did it, when and why, and where it's called from. I'm pretty basic about that. I know some people are a little more, you know, casual on this score, but I want to put as much information out there as possible, in case I lose it and someone else finds it, they can return. No, I just like it. This is my first attempt at creating an SVT drawing from an inkscape extension using Python. I make it public because it's a good example of beginning-level Python programming. And because we're using inkscape, we don't have to fool with I.O. You know, input output is a real means of paying for beginning programmers. And you get immediate response. Of course, you get this from Processing.js, as Pete was saying earlier, but this is how you look like on. There's just some things you want to do. You want to make sure that your inkscape extension, where your inkscape program is stored, the extensions that come with inkscape, you want to specify that directory. You also want to specify the directory where your personal extensions are stored. So, you know, this dot here means that it's off of your home directory, hopefully. And here are two dependencies, inks and simple style. And here's my class generic that I love. I do anything with that. And now I'm starting the class drawfront lattice. And now it's gone. Okay, I just wasn't able to get to the scroll bar. This is fine. Okay, well, is this up? Can you see? Is this good? All right, good. We haven't cut anything off from the left one. All right, so now we have that class generic. And now it looks a little funky. But the first thing, you know, I'm defining my class drawfront lattice, and I want to make the inks effect an integral part of this so that I don't have to refer to it all the time. I can just refer to the functions that are available in it. There's our magic init. Inks effect, well, we have a function init, and then we use the inks effect init to create an inkscape object, which is your canvas. And I'm assuming that it uses your default template to do this here. And I've looked at the code, and I don't see any way to create a new inkscape document using anything other than the default template. If any of you know how to do that, I would love to know. One of the things that's available through inks is this option parser. You know, once you create the document, you know, there are some default things that are added to it. This object option parser is part of that document. So the self, this document that we just created, has this option parser automatically added to it, and it has a function added to it called addOption. So we are line by line adding the parameters that we had specified in our inks file. Next conference, shoulder width, front-on pit distance, all that stuff. And so you have to parse this in. This is an important step. You can't skip it. To pull your parameters in from your inks file into your Python environment. Okay, that being done, I have another function that I love, which is debug, so that if any point in my program is not really working, I can shove this debug statement there and say, okay, show me point A, or give me the, and I can even look at values in the SVG document in the DOM level or the CSS level, which is, and it's very, very useful, but it is calling a Linux statement, the sys.standarder.write, and then a string of the message, and then a carriage return. So, but that is an essential for me because I make a lot of mistakes. I have to do a lot of debugging. So here's the first thing, draw my line. And again, I'm calling my function very simple, silly names to let people know, to let, you know, seventh and eighth grade girls know that this is, that this didn't come with the program. I made this up, draw my line, and here my parameter is very similar to the ones in our previous slides. It's referring to that this can be applied to our self, our current context. My layer, whatever layer I tell it to draw to. Couple x, you know, point one, x1, y1, point two, x2, y2, color, my, with my label. And so here's my style dictionary, here's my attributes dictionary with ID, and we're going to add a new, here we're adding another inkscape variable called label. So you not only get the SVG ID, you get an inkscape label, and that can show up in your XML editor, if you're looking at your XML editor in inkscape, but the inkscape label won't make it over into your SVG document, because it's SVG that doesn't care about inkscape stuff. But then again, I'm continuing on with the actual values required to draw a line. The first point, x1 and y1, the second point, x2, y2, and then the style is a rollup of formatting of that, my style dictionary. So here's the command, inkscape, true sub-element, my layer, add this new sub-element, it's a line, it's an SVG type, and use all these parameters. So here's another draw, my dot, very similar in its circles. And I use dots to mark points like, oh, center of my, you know, nape here, or, and also I use dots to mark the control points for busier curves, like around your armhole. So all, and those all go on a reference layer, they don't become part of the pattern. So I have a reference layer and a pattern layer, obviously. And here's a simple one, draw my Q curve, quadratic curve in SVG, because it takes one control point. So I decided to draw a separate function for quadratic curve, which only has, let's see, did it drop my, my path, oh, I'm passing a path definition to it, and it's parsing it as pixels. And D is my path definition, I think I called it, oh, draw my Q curve, okay, up there, it's a little different. I'm specifying the first point, the last point, and the control point. And then I'm creating the path within the function. So the D parameter in SVG is M plus string of X1, plus a common space, plus a string of Y2, plus a space, and then the Q for quadratic space, and then the string of C1, common space, string of the control 2, and then the final point where you're trying to get to. So that's, I think I left this in so you could see how easy it is, how SVG command strings are very simple, but you've got to wrap them up just right. So you create through the sub-element command myLayerIncEx, it's now path, it's not a circular rectangle, whatever, it's a path. And use myPath of Trips, and the path itself is one of the attributes. But here, in drawMyCurve, I'm saying myPath definition. I've already structured the path in the program, and I'm passing that path as a parameter to this particular function. And so here, you know, the D parameter is just myPath definition. Whatever anything I pass to it is going to turn out to be a path. It can be moved to the point, and then line to a point, and then smooth to some other point, and then curve to two control points, and then ending at another point. It can be a very complex path. So this drawMyCurve can do anything you want, and it can even just be a line. But as long as I structure myPath in the proper way, before I pass it to it, it'll work, it'll create anything. And then draw my dotted line. So I did this specific with a particular stroke, no fill, stroke with five, and give it a label. And here, in my Inkscape labels and my SVG labels are different. I figured this out earlier. I had added a new sub-element in my attributes. And later, you can just put label here in the attributes, and that's going to be your Inkscape label. So I'm just kind of showing, that's why I'm using this as an example, because it has a lot of my mistakes in it. You've got to figure these things out. So anyway, we're drawing a dotted line. And the dotted line on a pattern is the scene line. So you go from one point, X1, Y1, to X2, Y2, and the style is rolled up. You know, all of these things that I've specified. And then, call it with this add new sub-element, and it's a line. It's an SVG line. So it kind of, it just kind of rolls like that for sort of a long time. So one of the other things that I've had to do, and draw my cutting curve, that's the cutting line on a pattern is a solid line. And it's a little thicker than everything else, so I've defined it to be that. Now, one of the really silly things I did was refresh my middle school math. So, and I put a lot of comments in here, which I should probably take out. I hope they're correct. To get coordinates from points, I give it the point on a line, give it another point on this line. And then if I want, you know, the first line, that's first point, second point, or first point, second point. But I want to extend this line out from the first point. So the first point's here, the second point's here, then I'm going to go in this direction. If the first point's here, the second point's here, then I'm going in that direction. So I have the two points to find and a distance. It's kind of dumb, but as I said, this is, I'm kind of showing you where I started from. And so you have to find a slope, and I'm calling it a circle radius formula, but it's, you know, it's the a squared, b squared, c squared thing, so that you have to figure out. So m is get my slope. Obviously, I've got to get my slope function defined in here, and I'm setting it to two points, and normal, because, I mean, I did some really silly stuff here. I said, okay, normal means don't put it at an angle, just continue the slope. I'll put that perhaps a question. Anyway, R is my link, so anyway, yes. So I just want to make a quick comment. What you seem to be doing of recording the actual practices of expert close makers and translating it into code or formulas is extremely similar to what Donald Knew I'm sorry if I mispronounce his name, I just read. Don Knewt, the maker of tech, which is spelled T-E-X. Yes. Are you aware of this? Yeah, yeah, I am. Yeah, so this process seems to be the same. It's very similar. Yes, and... Only Donald Knewt used 2.5, this is value percentage. I think 2.54. He's also the inventor of a measurement system, so I think he can be forgiven for a great many sins. Thank you. But yes, that's... Any other... He's big influence. You're making tech closely related. That's a good observation. Just a request rather than a question. We've seen a lot of the code and I want to know if we can see a demo of it working in sliding scale. We'll do it, okay. But I just want to let you know at what level we're working at here. So I did all this, crunched it out in a middle school desktop style. And this is what I was able to see. We're of course a bit running overboard, but... I'll do one example and I'll begin. I'll run it. It's as you wish. I find that interesting, but... It's whatever you guys want to do. I don't care. He never does. He never does. Okay, here's my... It says mine. And here's all my... It doesn't include the entire string. I have dates and versions and stuff sticking off here. But the one that works that I want to show you is this one. And those are some measurements. Don't look at them. Okay. So I can... Here, let me go ahead and just do an outset here. I can choose a path and do an outset because I've drawn one line on top of the other. I had both lines here, the dotted line underneath, the solid line on top. So I went and selected the line and did the control right-paren to create an outset. And so my outset has been previously defined to be the width of the seam allowance. So that path jumped out 5 eighths of an inch all the way around. So let me resize the document to fit the picture. And now it's... Did it do it? I guess it did. Let's zoom out. Okay, so that's a front bodice block. It's very, very simple. And all those functions that I was showing you that I'd written, we cleaned those up, pulled them out, created our own library to make it easy. So each pattern, you don't have to go through that. You just write your formulas. And if when I want to print this, just go to Layers, find my reference layer, hide it, print it. And if I have a problem, let me go ahead and show that again. If I have a problem, I can go into the XML editor and say, all right... See, some things have been escaped labels, some don't. Like this didn't have... It didn't have it. But see, you can go in and kind of look at that path. And it's huge. So you're not going to get any information out of it. So if what you do is pick a point that you find that you think there's a problem with. Now that's the control point for the neckline, for the quadratic curve that forms the front neckline. I want it to be in a different place. Then I can go and say, or if I'm confused as to what point that is, I can go in, select the point, go into the XML editor. It's already highlighted. And it'll tell me what the idea is on that. Quick question. How do you print out your patterns? I have a big plotter at home. I found it at a technology recycling center for about 75 bucks. It's an HP 755CM. Because I have a funny feeling my wife would be very interested in this. I'm trying to talk to printing companies, printer companies, to just make a black and white basic plotter that... Mine's 36 inch wide and it's a roll fee. But all you need is black. You don't need any color. You can get a plotter that can have a small chalk on it so you can actually plot on textiles. Oh yeah. I want that to be part of the program too. Here's the thing. You can spend $250,000 for the Lexmark or Gerber fashion design stuff. That gets sent over to the $2 million layout program to show you how it's supposed to be laid out on the cloth. And then that gets sent over to the $2 million cutting machine. Now it would be great if we could have all this in open source. Because not everybody wants to make so many clothes that it goes to H&M and to all these different department stores all over the world. Maybe they just want to make enough clothes for their neighborhood or for their city or for a few stores and states. I just wanted to say one of the other functional models for this too is like the open clip art. Imagine a situation where you create a pattern, you upload it, someone downloads it wherever they are, prints it out and then just stitches it right up. That's sort of the vision that I saw in this particular case. Since I was just starting out on why you don't need a plotter, another thing you can use if you just calibrate this and you can do it by a little bit of practice, is use a projector and then just trace it straight on the textile. Lots of people do that with these old patterns. They get their projector, put it up on the wall and draw it out. And then they pull it into Inkscape and straighten up the lines. And have a ruler as we saw in the mail. Was it Tom's presentation? Yeah, the layout. You have the rulers to market so you know what your reference is. But yeah, there's a lot to this. What I want is a website for people to put their patterns up there and client can log in into their database, their measurements. And then from this database, they can pick and choose what patterns they want. They can download that pattern right then. They can click over to whatever fabric vendor that we like or that they like. You can have some links and they can order the amount of fabric that's needed to make that pattern and all the notions and stuff and have all that shipped to them. Or they can pick the pattern, pick the material, pick all the stuff, pick a seamstress to sew it and have it shipped to them ready made. A lot of things. That's cool. Really cool. I'm curious, it seems like there's a lot of stuff happening. So I'm curious how, where it's directed, where people could get involved. You know, there's a, I mean there are obviously these things happening. But is there a place where the codes at? Or some directed effort? We pretty much came up with a final, sort of a final second version about three weeks ago. And then we got hit with tornadoes and things. So we didn't get a chance to post it. But I will put that information on the create list and make it known where to download the code. You can have it on. Okay. Okay. You also have sewed brilliant. Oh yeah, there's a sewbrilliant.org site, sew-brilliant. That was the name of my stitch lounge that I had in Huntsville for a couple of years. I shut it down and started doing this. So I have about 12 really old but great sewing machines if you want one. Let me know. Because I have 12. So I need to get rid of them. Anything else? There's still two talks before lunchtime. It's for us to vote. What do we do? It's actually quite interesting, obviously. Everyone is into it. Shall we do the two other talks also? Thank you. Thank you very much. Thank you.
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* I. Presentation of project development during the previous 12 months. o I1. Description of software development from manual technique to procedural code to object oriented code. o I2. Discussion of how the pattern was separated out, leaving a generic engine. This coding approach allows the designer to retain pattern rights while the engine is open source software. * II. Illustration of how a beginner can develop an idea and take it forward. * III. Presentation of current product.
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10.5446/21680 (DOI)
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My name is Chris Weber. I work at Creative Commons and do a whole bunch of fun things, I think, generally. I'm here to talk about Blender, and there's not much time, so I'm just going to jump right into it. But it's specifically Blender for advocacy animation, and why I think it's so great. Oh, so I already said some of these things. I also have a website. I'm working on something called Community Goblin, which I'll talk about later. I like Blender. I make weird drawings. So Blender is a fully-featured 3D suite usable for modeling, texturing, rendering, animating, compositing, video editing, most 3D things, and then even have a game engine. But you can tell I stole this from my Python version of the talk. But anyway, it's also all free software, and it's under the GPL. You can do a lot of cool things with it. I was going to show a few couple of brief clips. I don't know how good of an idea this is, considering how much time we have. But this is a particularly cool one, and I hope it'll play the audio, but I'm not sure if it will. I don't think it is. Well, it's not as much fun with all the audio. I'm just going to skip ahead. Anyway, it's got this cool thing. There's this thing opening up. It's got this monster breaking out of it. Oh, there it is. It's got this monster breaking out of it. So I kind of skipped through that in the interest of time, but one of the cool things I think about Blender is that they have these DVDs that help you be able to learn how to do this kind of thing. And this is one example with Preacher Fast 3, which basically is a tutorial by the guy who created that film, and he set up the 40 hours that he took to make the film and showed you how to do it. So I think if you're wanting to get into Blender, it's a Blender science. It's a Blender Institute training DVDs are a great way to go, especially Creacher Factory and Venom's Lab and stuff. And now, OK, so now let me jump into Blender itself by jumping into psycho.blend. This is a little guy I created. He's somewhere on my website that I don't remember where I linked to. And I'm just going to show a few basic things about Blender because I think people tend to get overwhelmed when they first use it. So first of all, you should know that Blender is a very splitable application. You can split things, make sections for whatever type of thing that it is that you need at the time, and you should really operate Blender as if you're playing a first person tutor. You use one left hand, you leave your left hand for the keyboard and your right hand for the mouse, and this allows you to do things super quickly. In fact, I'm going to show off one thing which is pretty cool. I'm going to show off a couple things. First of all, I guess I'll get into modeling in Blender just as a quick example. Things are based off of vertices, faces, and edges and stuff like that. You don't have too much time to get into it, but here's just a quick example of me taking this guy and giving him horn. Pretty cool. If I had Mirror modifier on and we show up on the other end, but I don't, I'll reload the file, and I'll show off the animation. So you can modify methods, you can rig them up so that you can mess around with them. So this guy's all rigged up. You see he's got a skeleton. I can grab onto this thing over here and move it around and this thing over here, and I can also go and grab onto his legs and start moving those around and stuff like that. And if I want, I can even grab onto this thing and start making him look around. So animation. What is animation in Blender? Since I'm talking about animations, I should probably show you. It's actually not too complicated. The basic ideas are that you're just inserting keyframes. So let's assume I'm going to move the following things around. I'm going to move this. I am selecting the wrong thing. And we'll grab his feet. Damn it. He's accidentally selecting that thing and it's making it my life difficult. So I'm just going to insert these one by one. So I'm being stupid. Oh, I just used the record thing. Okay, insert location. So now I've inserted the location of these two things. I'll move them up and actually move this forward a little bit and insert the location again. And what did I do wrong? What? That's impossible. That's impossible. Wow, I'm not bringing this talk off to you. It's awesome over the third as I thought I was going to. I don't know why my animation tools are not working right and that's because I'm in the mesh. Sorry. I am going to restart this. Grab onto this. Insert it. Move it up. Switch to the timeline. Move it up again. And now it moves back and forth. So this is the basic idea of animation is that you end up taking some property, you end up moving forward in time or something like that, and you enter the key form and frame it at another point. So in this example, I'm just moving around these wings and now he's starting to fly. I could also move around his eyes via this control way that I have here, but I seem to also still be having trouble selecting things and in the interest of time, I'm not going to do it anymore. So bye, Psycho. I just wonder, I am not thinking during this presentation today. I'm sorry. Okay, moving on to other things. We still don't have much time. About the animation, about advocacy animations in particular, and also the patent absurdity stuff that I worked on. So I did some animations with the pre-saltor foundation on a film called Patent Absurdity. And I actually really wanted to put this idea for a while that we should be able to try to take animation and use it as a form to help people understand things better. And this came up through an opportunity. They were already working on this film, so I decided to do it as a holder for a band. So here's an example of talking about kind of a field of task. Patent Absurdity is like a law that was forced to set up patent and fill out. They had to patent it, but for the intelligence they had to trade with the companies that had patents. And so the arsenal started developing. And by the year 2000, 2001, Microsoft now holds thousands of software patents. Oracle was probably approaching a thousand software patents, Adobe. And all of them have become more and more aggressive. Patent is, and some of the ones who were against software patents ended up doing other companies. And so what you had is an explosion of patent things first, and then an explosion of litigation. Anyway, so this is, I thought, this seems to go really well over with people who end up watching the film. I think that animation's do a great job of being able to take something and really kind of opening up the space for it. So I'm just going to talk about some of the animations I did with the film. I did that. I also just did some really stupid graph animation, which was just kind of in here first throughout the film while they were talking about the actual buildup of patents. At the end of the film, actually Richard Stallman had been talking about earlier in the film that there was this idea that what would happen if, you know, Faith Hylven had been, if there were these musical idea patents and stuff like that. And so he, and that he probably wouldn't have been able to invent it, the stuff that he was doing. So for the finale of the film, you decided to do this. So that was pretty much that. There was also this really boring timeline thing that, we just kind of flipped through these different types of things that they were going along. And so I'm going to walk through these different sections of these animations I did and show you basically how to reproduce them. The first one is the timeline animation, which is that one I showed. We basically had a whole bunch of, we were kind of trying to show the timeline of patent information as it was going through. And so we, what we did was we took the, we created a bunch of templates inside of inkscape that were, and I should have been smart enough, an inkscape first, that were basically the different images that were on this timeline. So if I render here, you should see this one starting to appear in the view. So this is a pretty good example of how to start getting a really easy example of how an animation is done. You can see all these keyframes over here. To be able to do the timeline animation, all we really basically had to do was take an image, which is what each one of these things is. It's just a simple plane with an image mapped onto it. We had a camera and we just moved the camera down from one item to another. And so you can see that happening here with the camera moving down if I move along the timeline. But there's also one other thing that was being animated. And I think this is one of the exciting things about Blender 2.5 is that everything is in theory animatable. And actually that's what we did here with this item. I think it should be on texture. So you can see this property right here, which says it's the alpha, which is the transparency. And so as we move between these two sections, you see the alpha moving from 0 to 1. So that's because you can just hover over a property. For example, the alpha just inserted at some point, moved to another point, and inserted at the next value that you wanted at. And Blender will handle that animation for you. So that's an example of a really super simple animation that we did that was really stupidly simple and easy. And I think hopefully fairly easy to describe. So, yes, the graph animation. So we extracted a bunch of stuff from Inkscape. We actually opened up, I was given a PDF full of graphs to use. So we just opened it up in Inkscape and just started messing around with breaking up the tasks individually, which was really painful, moved them onto separate layers, and then just animated those layers moving out of place. Let me pull open the graph animation. There's a simple version of this, and then there's a scary version of this. So the first graph that we did was just actually a graph moving into, slowly becomes visible. Well, this is kind of me being smart and happy. If you see the line becomes visible, I was really lazy and thought that Blender would be really easy to use for this, and it was pretty easy. But what I'm actually doing here is something semi-evil. This is actually the image itself that we were making, and I was actually just, what I did, I said Blender has a whole bunch of video editing tools and other things like that. It also has a compositor with node editing. So in the node editor, I just ended up setting an image on the background layer. You can set an image on this like that. I'm not sure how to make it visible right now. And then I actually just set this thing, which is a plane, just actually in the compositor. Man, I'm not able to describe this at all at all. Just kind of blocks out the view as it goes through. You can do a smart thing with nodes to be able to control the alpha of certain layers and stuff like that to be able to make something fully visible. Let me close it. And then there's the ending beta open animation, which is pretty much the same idea as the other timeline thing, but just slightly more complicated. What we did was you can see there's all these different layers here. And each one of these layers, these things, this would be a lot better if I had shader support on here because then you could actually see the images. The camera actually just moves along from each one of these to the next. So if we move to the camera view, you can see ourselves moving from image to image and then slowly dropping off the page. So you can see this move away, this move forward. And actually maybe it might be a bit easier if you look at it from this perspective. So here's the planes down here and the camera up here, if I press animate, to start going through the animation. Oh, it's going super slow. But you should be able to see it happen. So it moves along taking a long time. You can see one of these planes basically drop and move down. And so that's all we were doing was actually just moving a bunch of planes around with images mapped on them and controlling their transparency as to whether or not they came into view. And that's all there was to it. But these are kind of boring actually. The thing that everybody wants to know about is the Wargames animation. I showed the other ones first to show just basic simple animation properties. But here's I think what everybody wants to see. This was actually kind of completely evil. So we have the image on the background which was done with Inkscape. And we have this moving along. You can see in this example here, I really should have split these out better before I started doing this. You can see this line basically grow. Now the problem was that when we entered it actually doing this animation, there was about like 10 million different lines actually coming in at one time. The way that we ended up controlling the visibility of this line here is something that I learned from my friend Bafam, which is you actually use a curve to control the thickness of another curve. I'm not sure if I'm going to be able to get that in time. So the interesting thing is that we actually use the Python API to control each one of these curves. You can actually select a curve and you can put particular properties on objects. So I would actually just add a custom property to each one of these curves that I was working on saying what the end frame was, what the start frame was and everything like that. And just use the Python API to enable transforming it into a curve. So this is what, yeah, so I wrote a Python script called MucifyCurve. What Python scripting actually looks like in Blender is something like this. If you want to add a monkey, for example, you can go to add mesh monkey. Now you've got a monkey. If you want to do that via a script, you can actually just go to the info box, add a monkey, and it will actually say over here the Python equivalent for adding that monkey and also spruing up my rendering in the process of trying to copy it. That's a stupid and tell bug that keeps annoying me. But now I can reproduce that by doing, cpi.opt.mesh.Munkey. Yeah, I should add a second monkey right here. So what I did actually to be able to create all these curves, I just figured out the procedure for adding each one of them by hand, which was I added a curve and then I would add another curve that controlled the thickness of that curve. I knew that I wanted an explosion at the end. And so it actually just the properties of the radius of the explosion. I would set the template for the curve that controlled the other curve. And then I would just move that along. And so the script would actually just take the properties that they are on there and make them all visible. What's up? 10 minutes? Oh, man. Okay. So, Creative Commons Animation Films. This is one thing I wanted to show real quickly. I guess, I think that there's an opportunity to actually be able to show and get people excited about ideas and always feel by actually moving through. This is an animation that actually got me fairly excited about Creative Commons while I was in college. And now I'm looking for ideas. But the ideas of it, this makes me really clear. I've been really stumbling through this entire talk and I have no idea why when I gave this an awesome presentation last night at the Python Music Group. But what I'm trying to drive home is that there's a space that's open when you end up having animations and having things like this. We have some ideas like the free software definition has been around for over 20 years, but almost nobody is able to understand what the free software definition is unless it's their DPM grade and free software. Could we end up getting the general ideas of stuff like the free software definition out to people by having some sort of more abstracted explanation of it? I think so, and I'd really like to see this type of stuff done. But I have pretty much completely run out of time. So, if you have any questions, look down. Questions, anyone? I'm still having trouble understanding that the curve controlling another curve. So, the animation with the patent warfare one, you said like you had one curve and then you had another curve? Oh, okay. So, I wasn't sure how well it would get into this because I think it tends to really confuse everyone, including myself. So, let's see if I can find the layer that this is on. So, here it is. You'll see as I move throughout time here that this, it's not that one. This one and this one. Nope, nope. There it is. So, you'll see as I move throughout time that this curve and this curve that I'm moving about, this curve as this one moves along, it's actually extending the other one. And the way that this works, I can remove this empty here real quick. And these points are actually, will actually just control the entire width of the curve. So, you can do really clever and evil things like sublide. And you can see this part of the curve is getting really thick at that edge. It might be more obvious if I make it like that. So, the evil thing that I actually did to just control the visibility of the curve was I just set up a, I set up this curve to control the other curve and I actually just set it basically between one and zero at the point at which I actually wanted it to be visible and I set up a hook between those other two points which was the empty that you saw in the middle. And that's this thing. So, as I move this back and forth, it moves those other two points. So, this thing is controlling the two vertices in the middle. And so, the animation is actually just moving things from this point to this point. So, it's a clever evil machine to be able to control the visibility of the curve. I actually just animated basically my strip would insert this thing here and then it would insert this thing here and then back and forth on the timeline, it would just move it. And to be able to create the bombs, I would just insert a sphere at that point and just move it up and stuff like that. You may want to play with this on the other machines on the side. Blender's been installed there. I'm trying to get more users on those Blenders. Any other questions? That little guy with the wings at the beginning, if you have not already, would you be willing to upload him to OGA because I'm sure he would go great in some games? He's actually been on my task list to upload to OpenGamer. If you don't know what OpenGamer is, Bart runs a wonderful fight for game stuff. I think he's talking on a panel. But anyway, yeah, I'd be willing to upload it. I really should and I will soon. Well, one follow-up. Do you have a general tutorial anywhere about how you made him? I don't have a tutorial. I can make one. Really, it's just kind of box modeling like this, where you split things so you start making the shape. And then I might take this birdsy here, extract, extrude, move it in, extrude it here. And now we have kind of an eye hole on this side of the face and stuff like that. So really, just box modeling. It should be an edge modeling. I just take kind of a general shape and I just keep splitting it down and adjusting the properties until I get to that point. But I think there's a much better example of how to do this kind of modeling than I can have, and that's to watch the Creature Factory DVD or the Venom's Lab DVDs that the Blender Institute puts out because they're creative commons license and you could actually watch them without having to pay for them. But anyway, but if you do a really good job of explaining like basic modeling techniques and stuff like that. Cool, thank you. I'm curious, what was the production process for the animations in the movie? Did you collaborate with people? Did you have a graphic designer? So there was the director of the film, Luca Gattani. Basically, we talked about the type of animations that we wanted from the beginning, and then they decided they wanted the War Games one, and then a couple days before we released the thing, they decided they wanted a finale to the film and wanted the Beethoven thing. But actually, that was kind of fun because I was given a lot of control on how to do the nuke scene basically. They just told me to do basically whatever you need. So, in terms of the timeline animation, I was given a file that the Free Software Foundation worked with one of their patent expert people, and he basically gave me a history that I should convey through the file. And I just opened it up and made a bunch of templates, put them in that file, and animated it. And with the Beethoven thing, actually, the director's friend, I think, made a MIDI file. He didn't actually give me the MIDI file to play with. Then they gave me a bunch of SVG files that I could open up in in-state that had all the notes and everything like that. They broke it up into image layers for me, and they told me, make this disappear at this point, and this point, and this point, because I don't know crap about music. So I was just able to animate stuff to, I was just able to list up the timings that they had written in that file, and they should just do that. But I think part of the film was still that, the nuke thing anyway. And that was like, hey, we really need this cool nuke display thing, and I just figured that out. Thank you. Thank you.
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Blender was used in the film Patent Absurdity to produce several animations. I will describe how those animations were made and talk about how Blender could be used for further free software / culture advocacy animation work.
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10.5446/21794 (DOI)
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I'm talking about XSLT, how many people here are using XSLT? How many are familiar with XSLT 1.0? Okay, keep those hands up. How many are familiar with XSLT 2.0? I want another hand. Here's a test. How many are familiar with XSLT 3.0? That's my 300 people in the room. That's the problem. So today I'm going to talk a bit about the Jets' previous star sheets themselves and work that I've done with XSLT 1, 2 and 3 using Jets in Tommy's terms from yesterday. This is a three-part, a we done good talk. So the Jets' previous star sheets are available on GitHub. They're developed in XSLT 1.0. As a government project, they're in the public domain with no copyright issues. And they were developed for NCBI by Mulberry Technologies over the years. What you see is the Jets' previous star sheets based on the previous NLM star sheets. So this is what I call a selfie because my paper formatted with the Jets' previous star sheets with a screenshot of my paper formatted with the Jets' previous star sheets. I'm not quite sure whether I should put quotes around selfie because it made it into the opposite English dictionary at the end of last year. And then Ellen made it famous. The timeline for the Jets' previous star sheets is reconstructed from conversations or emails with Tommy and Kim. And the comments in the code is that the initial design for them was done back in 2004, NLM version. I have one dated 2006. And the current 1.0 star sheets were released last year, released in 2012. So the question becomes why are they still using XSLT 1.0 in 2012? XSLT 1.0 is still the dominant XSLT version with some platforms in Microsoft. And we support XSLT 1.0, the one that you think of with Unix and Linux, XSLT PROC is 1.0. But the star sheets themselves have been tested with XSLT 2.0. And if you look through the initial comments, there's notes of when changes were made because the differences between 1.0 and 2.0 have adjusted it. So it works properly with both. And with the main work of being done in 2006, 2007 for the NLM stuff, XSLT 2.0 was new and there was really only one version, one Java version that most people knew about. So what do the star sheet packies that you download from GitHub actually do? There's three parts. There's the pre-processing for doing things like converting the Oasis Table model to XHTML for massizing citations and things. In terms of XSLT star sheets, there's star sheets for converting Jats to HTML and Jats to XSLFO for formatting in the PDF. And there's also post-processing for turning HTML into XHTML for the sake of MathML. I'm not quite sure whether that's a bit out of date with current browser capabilities with MathML. The stuff that I'm talking about is the formatting through XSLFO for producing as PDF. The position of the Jats star sheet maintainers on customizability is that as it says there, this is the entry point for customizations. They're not accepting patches or changes to add any more customization parameters, any support to fancy processing instructions as you find with DocBook or TI. I mean, TI describes itself as having several hundred parameters that you can change. It's a link to Jats itself that go on for the core part and you can customize it yourself to make your own solution. So I'm going to talk about three parts of XSLT that make it easy to do these sorts of customizations. And I'll talk about the Jats star sheets and what makes that easy to do customizations. XSLT, for those of you who didn't put your hand up earlier, is largely organized in terms of templates where you have an XSL template, you have a match attribute, which is the context where this particular template is going to be used. And the content of the template gets instantiated into the result. The stuff that's in the XSL namesprace gets acted on by the XSLT processor. The other stuff gets copied straight through to the result. This is useful in terms of customization because you can write templates to override the base template. And the features of XSLT for being able to make modular star sheets or XSL include an XSL import where includes you pull in the entire contents of the other star sheet as if it was at that point in the document. And XSL import, you're referring to the other document and these templates are there and they have a lower, what's called import precedence. So it, there's templates in your star sheet can override quite easily the ones that are in the imported star sheet. This is something of a boring, blocked item, I must admit, but there's slightly more complicated ones later. So this is the basis. The ability of XSLT to override templates, as I said, means your, your importing star sheet can override quite easily whatever's in the imported star sheet, which is good when you're making wholesale changes. But sometimes you just want to change one little thing and one attribute. But you're going to have to copy the whole template just to make a, a copy of a small change. The third aspect of XSLT itself that makes it easy to do these things is what's called attribute sets. We can set up definitions of multiple attributes and then refer to those in multiple places. And the way this works isn't, you're not just copying attributes literally, they're evaluating the, in each place. So in this case here we have the, we're like each time we use it, we can make it ID actually, we're going to generate a unique ID each time. It's not just copying little things. So how this plays with what the JAPS preview star sheet provides. The JAPS preview star sheet is fairly well arranged with global variables for things like the font family that you're going to use for everything. It has attribute sets for the common types of attributes, common formatting parameters that you're going to use, which quite often refer to the global, have references to the global variables. And it has a lot of name templates which is sort of the XSLT process you can do to sub-routines. Lots of common processing is put into a name template and used in multiple places. This aids customization, but it's the sort of thing you do in a star sheet anyway to what's called the drive principle. Don't repeat yourself. You put the thing in there, we're using the variable and use it in multiple places, use the attribute set in multiple places. An example of this, this is taken from the XSLT 1.0 part that I'll be talking about. In the customization, I have an attribute set which extends one minute defined in the core star sheet. And then I made a second attribute set which further extends the attribute set which is sort of partly mild and partly the base result. And in a template, I made a template that matches a more specific context that this would be used in this specific context on the template for the table cell in the core star sheet would be used in other contexts. And I've made some changes, but I've also used the name template that is in the core star sheet. So I've sort of extended reuse, but also using the facilities of the core star sheet. So in summary, talking about the chat star sheets themselves, in 1.0, while they're explicitly not adding more customization ability into the core star sheet, the way it's set up allows fairly easy customization. All right, so I have on the side here about GitHub. We heard about GitHub in a question earlier. How many people here know about GitHub? Well, quite a few. So I don't need this slide. So GitHub is, as it says, the world's largest open source community, which it's because it uses Git, it makes it easy to copy and modify projects. So the data is previous star sheets. Being on GitHub, it's easy to copy and modify and make your own versions of them. So the XSLT 1.0 case that I'm talking about was done for a government body. This is an example of a couple of pages of, again, my paper sort of formatted with a couple of font changes using the star sheets for this. The source that I was using was JetsBlue with some custom metadata. The output was fairly similar to the pages produced by the chat star sheet themselves, the differences in the headers and the footers, different cover page. So this was done with XSLT 1.0, partly because of the client preference and partly because there were large parts of the Jax core star sheets that I could reuse because of similarities in the markup and the page design. So the customization, we're all mostly done in a new module. I changed about 10 attributes in the core star sheets just because I didn't want to copy large templates just to add a couple of attributes. The structure that I came up with here, there's two star sheets to do with massaging the math ML. There's the customization specific to the project and then we're importing the core Jax star sheets in the way that import presence works. They're the ones that have the least to take, so they're overridden by other cases. The math ML picks up, there was two, one caused by the content created by the client and one by the formatter. The client's problem was they were creating display equations and they wanted nice little parentheses around the number indicating the number of the equation, but it wasn't being produced in their math ML, so we just did a quick massage to add parentheses in the formatted result. The second one, as you can see, is we had a problem with the combining characters going too high. There was a workaround suggested by the technical support of the formatter and then to change it with a different character and the latest version of the formatter has a rewritten math ML engine and by just deleting one line from the star sheet, they'll stop importing that module and they'll stop having that effect. I'm not going to go through what everything was done in the customization, so I just did a quick touch up of what sort of things I did. Like 7% initial comments, about 20%, 18% of overriding variables and attributes which were defined in the core star sheets. A small amount of defining my own new attribute sets, a fair amount of the top level templates which are doing things like changing the page size, the headers and the footers. You always spend a lot of time getting the cover page just right, 35% on lower level element templates and the XSL 1.1 allows you to put bookmarks which you can render in PDF as PDF bookmarks so about 7% of code was done for that so it's a nice little table of contents on the side when you view it in Acrobat. The summary for this is that even though JETS doesn't explicitly support customization, it was fairly easy to base customization on the JETS star sheets themselves. The second project was done for the journal PLOS 1. The way that PLOS has been talked about in previous presentations and I think you understand too PLOS is it was as you can see two column layout differences in the way they present the abstract and the other metadata. The source was sort of NLM markup. They wanted lights out batch formatting but they wanted to reproduce their format exactly as closely as possible. So for this I used XSL 2.0 because there are going to be big changes to the way I handle the metadata, the figures, the tables and getting the figures and tables floating the way they wanted was going to be required vendor extensions anyway. So I copied and modified the core JETS XSL star sheet out of the additional modules as you'll see. So the thing about what they wanted for PLOS 1 is the figures float to either the top or the bottom of the page and figures could be page-wide or column-wide depending upon the size of the figure. Tables could be page-wide, column-wide or they could be rotated depending on the size but the problem is there's no size indication in the XML to say this should be rotated or this shouldn't, should be page-wide. Another thing that came up after I did it wrong is they want no figures or tables floating after the start of the backlather. How this ties into what you can do with XSLFO is that in XSLFO as defined you only get page-wide floats and they only float to the top of the page. They don't break so I had to do something about the multi-page tables. And the size, intrinsic size of the graphics wasn't available in the exosalty processing stage. I also had to do something because the way XSLT and XSLFO is set up is sort of far as we get. You do it in the exosalty, make your decisions in the exosalty, the exo processor works with it and that's the result that you have. So the table handling, I did an initial pass to pre-format the table in each of the three widths, column-wide, page-wide or the width of a rotated page. Format that, get the area tree, an XSL representation of the formatted areas and look at the areas for each of those three versions of the tables and take the one that had the least width and didn't overflow or the least area, rather. And use that as a basis for making good decisions on the formatted result. So here's an example of the three tables, formatted the three different widths and the first two tables fit okay as column-wide, third table would be too wide as a column. So it fits okay as a page-wide but have less area than the one that would be rotated for page-high. And here's two of those tables placed on a page, one's column width, one's page width. So the usual processing model which is pretty similar to what Liam showed you yesterday is XML, XSLT, process the XSLF formata and produce PDF. So to add in the table handling we get this. I need to process it once to get those three tables and find the areas and then use that as input to the style sheet to work out which is the best width to produce formatted output. Now I said we also need to do this something similar to graphics and we don't have the size of the graphics available. So the processing gets the graphics uses the image magic identifier program to get the size of the graphics once they're done as well-formed XML. And similarly we pre-format the graphics in each of the three widths to work out the exact size. We pick the best one and potentially it has to get scaled down because we also pre-format the captions so that the finger on the caption will appear on the same page. So what this is done to the processing model, we also added another step to make the well-formed XML with the graphic sizes, read that in the file sheet and then we can use that as part of the decision-making on the way to getting the formatted output. The third problem that I mentioned is that we can't have any floats appearing after the start of the back matter. So the solution for that is what you've seen as the final output. We just turn that into another area tree and we work out from the back matter and the positions of the floats whether any floats come after the start of the back matter. And if there is, we write out a different FO which is split into two page sequences such that all the floats appear in the first page sequence and by definition that finishes before the second page sequence with the back matter. So the end result of all of that is multiple style sheets, multiple uses of the area tree and some external programs which led to this structure of the imports, etc. So what was the Jets core style sheet is now sort of the plus style sheet because we wrote it, modified it in place. There are separate modules for the choosing, for sizing the tables and for making the right decisions about which one to use which use the same plus customizations. We're producing the same areas and then the splitter one does the same decisions as the size, choose the one but also makes the decision whether to split into one or two page sequences. So in summary of the XSLT2 version, it really shouldn't be this hard. We needed vendor extensions to do the column wide floats, etc. And finding the sizes, the intrinsic sizes of the tables and the graphics wasn't easy. The vendor's area tree is proprietary. You have to sort of work out what you're dealing with when you look at it. Getting the graphic sizes required next to the program, I could potentially have used the EXPATH binary module to do that as Liam nodding over there on the front row just telling us that he was doing a project. So the third aspect of using Jets with XSLT is with XSLT3. It's just a project for, currently it's a personal project for trying out XSLT3.0 features using Jets and the core Jets star sheets and trying out different XSLT3 parts on those. This quote is from, or just from last Friday, it's from the post to the XSL list from Michael Kay, the editor of the XSLT3.0 I suspect. It says, the design process does not include enough feedback. By the time people start reporting their usability experiences, the decisions are difficult to change, which is essentially sort of why I started this project, to try and make it easy place for people to try out XSLT3.0 features. If we, Bruce talked about my 20 years of markup, if you go back to 1997 and the Dissle days, all right, here we go. Anyone got a fourth hand for Dissle? Okay, a couple. We started using Dissle and there wasn't any sort of form or anything, so mulberry technologies. Started with the Dissle list and we all got together and tried out Dissle things and helped each other. We should go forward just a year or two to the start of the XSLT, mulberry started the XSL list and people, XSLT was hot, people seized on it and tried out everything you suspect came out, people tried things out, new process came out, people saw what it could do. And then you saw the timeline 2007, XSLT 2.0. By that point, people had existing XSLT 1.0 workflows. They weren't quite sure whether or not they needed some of the features of XSLT 2.0. And my perception is that the take up of XSLT 2.0 was a bit slower than the seizing upon the XSLT 1.0. And this project is sort of a place for sort of seize upon trying XSLT 3.0 things because if we saw from the XSLT 2.0 days leaving it to people talking on the Star Sheet, you don't get enough people trying things out quickly enough to be able to help the W3C process. Because the way it works with W3C is XSLT 3.0 is coming at last call. There's three more stages through the recommendation. But as you get closer to the recommendation stage, it's harder for the working group to make changes. So now is the time to try out XSLT 3.0 features, but we don't get enough people doing it. So the question is why am I talking about this with Jets? In part, this is a solution looking for a problem. I want to try an XSLT 3.0. I have some Jets experience. And Jets was the right size. It's not as big as TI or DocBook. So it has the Goldilocks factor. It's not too large. It's not too small. And trying out these things is potentially useful for the other users of the Jets Star Sheets. So the other thing about the Jets Star Sheets is that they're 1.0. Easy to upgrade, make changes. The public demand, so there's no ownership issues if you do make changes. And the fact that it doesn't support customization also helps because there's no user expectation that you'll continue to support hundreds of processing instructions and special variables. So the goals of the project is just to try different things. The way the GitHub allows you to just fork a project and make a change. It's meant to be let you just try and dip in, try something out or not to develop the patterns for using XSLT to develop the idioms that we're going to use. An explicit goal is to produce an XSLT 3 package, which is something new in XSLT 3, for XHML table modules because that's something that will be useful into the future. The things we're not looking for is to be the single one way of doing anything. What's impressive? It's supposed to vibrate. So to develop the patterns in the idioms because we sort of picked up idioms for XSLT 1.0, 2.0 along the way. And we will be developed once in it, XSLT 3.0, but as soon as we get them, the more convenient it will be. So the results so far, I've been trying out things with maps and non-retrunctions in XSL iterate. Some things that are due in XSLT 3.0, if it's been small advances, I do talk, which means the more detailed and external card, the reference to the paper is there. In terms of effect on the spec, I've so far been able to make three sort of minor tickets on the spec, some of which have resulted in action from the spec writers, which is useful in terms of the JAPS stylus sheets. I've been able to contribute back some changes to the core JAPS stylus sheets, which Kim has incorporated. Along the way, I found the XSLT processor bug, which I thought was an achievement. I've tried out Wendell's Oxygen JAPS plug-in and made a change for that, et cetera. So the XSLT work is available there on GitHub, but this is the time to try out things with XSLT 3.0 before it gets too cooked, sort of to baked into its current format. I mean, another comment over the weekend on the XSL list from Michael Kaye is that they're trying to work out arrays, and the tension is between making arrays look like sequences as they're done in XSLT 2, or making arrays look like sequences as they would have been done in XSLT 2 if they thought about it more. So this is the time to try these things out and provide the food to thought back to the working group. The results were documented on the Project Wiki or on my own personal blog. So the summary conclusion for the whole thing is the JAPS style sheets, you've heard me say this before, they provide the hooks for customizations either by layering it on top of the style sheets or copying and modifying the style sheets themselves, and they're proven usable with XSLT 1, XSLT 2, and XSLT 3. Thank you. Any questions? Went though. Tony, thank you. Can you tell us anything that we specifically, what should we look forward to in XSLT 3.0 and why would we jump into this trying this out now and help this important work? What are, and specifically with respect to the kind of system that JAPS commonly supports, publication processes, what are the, you know, what in your mind are the real killer features of XSLT 3.0? Well, there's, I'll take a question in two parts. There's why should you jump into XSLT and there's what's good about it now. I mean, hopefully I made the case that why you want to jump into XSLT 3.0 now is because if there's a corner cases that don't work, the syntax is bad or whatever, now is sort of the time for making changes to that is running out. I mean, one of the bugs that I had is to do an XSLT package. They had it so that you had to specify some stuff at the top and then there's the body, which is your conventional template, and then you had to specify some additional stuff at the bottom. And my point was personally I'd find that really difficult to sort of separate those concerns. And they had a good justification for it, but the end result is they've loosened things so you can put the provides and I guess provides requires either at the top or at the bottom because those sorts of usability things, the stuff that they can change now. In terms of what's in XSLT 3.0 that is useful for the stuff that we do here, your style sheets once again can be more concise than your XSLT 2.0 style sheets even. The usual shopping list of what's in XSLT 3.0, higher order functions, anonymous functions, maps, they work on arrays. One of the bits that I worked on in the style sheet so far is to do with trying to find alternatives to the XSL attributes. I mean, even though I've said they're wonderful, the thing is that you can't sort of easily override parts of an attribute set. So the first thing I tried out was trying to find a way to handle the depth style attribute on a table, which isn't CSS styles, it's an indicator of what style to use so that I could have a name style that also have all the full default processing for my particular style tables. Those sorts of things. Sorry, Am I? Sorry. A very quick follow up on that, Liam Quinn W3C. The time frame for giving feedback on XSLT 3.0 in current draft is measured in days and weeks and not in months and years. So if you do have feedback, don't wait. It's currently in last call. It's basically almost feature frozen but not completely. I'm personally expecting a second last call because of some changes that may come, but the changes will be small. So go send feedback very, very soon if you're going to because time is now. Thanks. Sorry, Laura. Laura Randall from NCBI. This might sound like a very ignorant question, but how exactly do we test these features out? Is there a processor that supports them currently? There's section. There's section that we need to have a pay not license for this section. The higher value ones will have XSLT 3 support. The one that is bundled with Oxygen includes the PE edition so you can do your XSLT 3 in Oxygen. There's another processor called X-ELT which has a beta program and I've been promised inclusion in the beta program for trying these things out. They are promising that their lowest version of the processor with the limited capability one will be free for, I think it's up to a four core processor or something. They're XSLT.net. Liam would know more about what the actual implementations are than I would. But the easy answer is Oxygen because you get the paid section. If you have the recent Oxygen then yes, Oxygen is the easy answer. Oxygen in 15.2? Yes. Okay. Thank you. Any questions? All right. Let's get them up. Thank you.
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The JATS preview XSLT stylesheets are written in XSLT 1.0. This presentation describes approaches used when customizing the XSLT 1.0 stylesheets for use with reports from a government body, when adapting the stylesheets for XSLT 2.0 for processing articles for an online journal, and upgrading the stylesheets to XSLT 3.0 as a testbed for XSLT 3.0 techniques.
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10.5446/21807 (DOI)
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I submitted this talk to, as a submission to Jatskine in response to the call for participation. And I have the advantage of not only having written the submission, but also being on the selection committee. So I got to see the unedited, unexpurgated comments of the peer reviewers. My favorite one said, there's no news here. Make it as filler if you absolutely need it. I'm taking that as a challenge to see if I can make there be news here, because I believe there is. People talk to me about Jatskine. They talk to me about Jatskine a lot. Sometimes they complain. Other times they call for help or advice. Sometimes they don't know the difference between the two. I think that's fair. But their complaints, in my opinion, fall into two categories. Sorry. Ah, that will help. Their complaints fall into two categories. Jats is insufficiently specific or Jats is insufficiently generic. And when they're complaining that it's insufficiently specific, that's either because there is no way in Jats to tag something that's really, really important or because there are several ways to tag the same information, which is unacceptable. This I have been told many times is unacceptable because Jats is a standard and there should be a standard way to do all the things that are in Jats' purview, one and only one. Jats should provide a standard way to encode journal articles. I have a lot of trouble with should-bees. But I can tell you that there isn't one and only one way to encode everything in Jats. And there isn't going to be. The request is putting Jats way back in prehistory. Many of you are not old enough to remember, how many of you remember the Gen Code Committee? Yeah, I see two hands. The Gen Code Committee was a whole bunch of really, really smart people who figured out that as you typeset material from one typesetter to another, you had to completely retag it. And that was a huge amount of work. So they set out initially to make a list of all of the tags that you needed for typesetting so that we could have standard tags as we typeset all our material. And they figured out after a few years of this that what they had really set out to do was to make a list of everything that anybody cared about on planet Earth. And they figured out that that was a pretty big task. So instead, they came up with a mechanism for people to say, these are the tags I care about in this circumstance, and this is the way they relate to each other. And they called that mechanism, SGML, and from SGML we have derived a slightly less convoluted mechanism for doing that, which we're calling XML. And JETS is a set of tags in XML for encoding journal articles. But it is not the complete list of anything that anybody might be interested in at any time on planet Earth, which is in fact the scope of the journal literature on planet Earth. I don't think there's anything anybody's interested in that somebody doesn't publish a journal about, probably several. So we don't cover everything and we can't. When I get panicky phone calls from people, it's usually either mid-afternoon on Friday or the 29th or 30th of the month when they really need to know how to tag something right now because they have a deadline. At that point, those people don't really want to have a philosophical conversation about the nature of tagging and making tags that list all of the things that anybody could possibly tag. That's not a conversation production people at 3 o'clock on Friday afternoon want to have, right? So instead we have conversations, well, actually most of the time what I can say to them is the words you used in describing the problem, have you looked in the tag library index under those words because usually if you actually look in the index, you'll find the thing that you're shouting about not being present. Sometimes it's a little harder than that. You actually have to find an element and know what attribute to put on it and sometimes they're really asking how to do something that Jets out of the box doesn't have a way to precisely identify and that they start getting really, really anxious because it's really bad to tag something by what it looks like not what it is except at 3 o'clock on Friday afternoon when the thing needs to ship, that's what you do. And besides which if this is the first time anybody has ever had this kind of information in your environment, that's still what you do. And it's okay because you need to get your documents published. That's what publishing is about. It does however give people a chance to think about why they're tagging documents. What is the point of your XML? It is rarely the goal of creating tagged XML documents to create tagged XML documents. Not never. Not all that many years ago I spent a couple of days with a fairly large publisher of periodical materials, journals, magazines and things that are sort of in the slush area between journals and magazines that might kind of be one and might kind of be the other. And they wanted me to help them improve their XML workflow. So okay, that's the sort of thing I do. This is fair. Let's talk about what you're doing. So they get their documents in Word and they copy edit in Word and they run them back and forth and eventually they send them to their page design folks who make pages in InDesign and then they've got their PDF and they send them to a conversion vendor who makes XML which they get back and they put on their server. And I said, and then what do you do with it? And they said nothing. I said, how much of it have you got? Ten years worth. How much of that is that in terms of data? That's a lot of data. Has anybody ever looked at any of that XML? Well no, we're saving it. Guess how good it was. Yeah, well, and the final recommendation I made was that the best way they could turn that XML source into money was to erase all that storage and then they would have some fresh storage they could use for something. It would have cost a lot more to clean it up than to just redo it. But let's assume for a moment that you are not making XML for the sake of making XML. If you want XML so you can interchange it with somebody so that you can do multiple things with your documents so that you can do the things that the people who talked to you in XML in the first place said XML was good for. The power of XML we told you was that it is possible, even easy, to transform your XML into other things. Yeah, that's true, but how well you're going to do with that depends a lot on how you handle complex cases. And the dirty little secret. You may need to do one thing with it for one purpose and something else for another purpose. All uses for the same data are not alike. Let's look at an example. Let's look at a, I believe, theoretical example. I don't know of anyone who's actually doing this. Let's imagine that there is a publisher in a field of study in which it turns out to be enormously important what languages were spoken by the parents and grandparents of the authors of the article. I'm not aware of any such field of study if there is one. Well, that's coincidence. Let's imagine that without that information, readers simply cannot properly evaluate the quality of the article they're reading. Sort of like you need to know when you're reading an article whether the research was paid for by one of the products discussed in the article. If a manufacturer pays to do research, you want to know that when you read the article. And in this imaginary field of study, you want to know what the author's grandfather spoke at home in order to evaluate the quality of the study. So this is important. You're a publisher of journals in this field. You want to tag your journals and Jats. Why? Well, first of all, because Jats is wonderful. And more than that, because you want to send your Jats articles to some vendors who will make your electronic products and some archives who will make your material available for the eons, and they want Jats. So what do you do with this information about the language of the parents and grandparents of each author? Well, you call Tommy and you ask her, where do you put this in your Jats article? Because obviously there's a place to tag this. And Tommy looks in the index and says, no, we don't have that. We have a way to record the language of the name of the person, but actually we don't have any way to record anything about author's parents or author's grandparents, much less their native languages. If you had called at least one of your service vendors, you would have been told not to publish that. If you were at least one publisher of just, I'm talking about people, I'm talking about people who are in this room. If you were at least one of the publishers in this room, you would then have not published it. That, my friends, is the only absolutely wrong answer. If this is important material to the people reading your content, don't let somebody say, the tag set doesn't allow you to tag it so you can't publish it. Wrong answer. Next answer, put it in a footnote. Authors can have footnotes. You can put anything you want in the footnote. Now you've published it. Have you done anything useful? Yes and no. It is in the published document for human readers to see. So a person reading the document will see it. And is it available in a way that people can, for example, search for it and find all of the articles in your field written by people whose grandparents spoke Latvian? Nope. You're going to do a search on the word Latvian. You're going to find a lot of stuff on all kinds of linguistic stuff. Can you do data mining on it? Nope. Can you compare things on it? Nope. But it's there. It can be seen. You could tag the languages as named content inside those footnotes. Named content type language history with the words paternal grandfather spoke Urdu. Well, how about author paternal grandfather's original language? So you've got named content, content type, author dash language dash grandfather, is anybody ever going to search that? What are the odds that any other publisher anywhere will use that same tagging for this same information even if they have the same information? So what you've done is you've thrown a huge amount of tagging at it and accomplished nothing. It's not even likely that your own staff are going to use these codes consistently, much less anybody else. So you haven't accomplished much. There's another possibility, of course. You could use custom meta. Jats provides in the metadata a thing called custom meta wrap which can contain custom meta which consists of a tag that says what is this custom metadata and what is its value. It's not associated with contributors and it doesn't have tagging for second author. It's also not associated with the author. So now we have to have custom meta type, second author's paternal grandfather's second language. We still haven't accomplished anything, right? We're tagging it but we're not tagging it in a way that's going to be good for anybody. So this is important. What do we do? We fill out the form on the NISO website that goes to the Jats standing committee that says we need you to add this to the Jats because it's really important and there's no good way to tag it. And you've already talked to somebody on the Jats standing committee who's told you if you want to send in a suggestion and have it taken seriously, you have to explain what you want and why it's important and give us a sample of the data. So you do all of those things. You fill out the form, you give us a sample of the data, you explain how important it is and the next time the standing committee gets together the standing committee reads your recommendation and says, this may be important to some very small number of people but it's not important to a lot of people. Why is the standing committee not likely to take this request seriously? Well partly because I made it up and I don't think it's true. But more important than that because there is pressure from those other people who keep calling us to make the tag set smaller. So you want to keep Jats small but you want to tag absolutely everything. Mmm, problem. I don't know what the answer is. There's another possibility. The Jats documentation goes into great detail on how you can customize it for your own use. We explain how we show you examples. Bits, the book interchange tag suite, did I get that right? I got it close anyway. Bits is a customization of Jats. It's out there on the web. There's a lot of people who will be talking about it in the next couple of days. There's an example of a customization of the Jats that you can look at. Maybe what you need to do is make your own customization. Or maybe you can get all of the people who work in your field to whom this is important information together, make a customization, publish it for your use and then you can all do it the same way. Now you've actually accomplished something, right? What's the downside on this? That's a lot of work. You're going to have to call Todd and say, hey, Todd, can we do this as a nice activity? At least you might want to do that because that gets you away from antitrust issues of getting together and talking about how you're going to publish with your competitors. It gives you a way to publish this thing you've accomplished. But it's not a bad idea. It's a lot of work. Now you still have the challenge of figuring out what are you going to do about sending these tagged documents to these archives and service vendors and libraries who do not live in your little world and who don't know what this stuff is. My suggestion, XSLT. Take this stuff tagged the way you really want it, the way it's really accessible to you and make it into something that they will handle until you can persuade them that you really, really, really are important and they need to handle this stuff in your rich form. I mentioned when I started talking, and I mentioned it just again, the pressure to make Jats smaller as well as the pressure to make it bigger. There are a couple of other pressures on it. My favorite one is the greenification of blue. People want to use the publishing tag set, not the archiving tag set because it's much smaller and it's much narrower and it really describes what they want to do. Except there's that one thing over there in green that we've got to have in blue. The challenge is everybody's just that one thing are different. So there's a lot of pressure to make blue a lot greener. I'm not quite sure how to fight that. I'm not sure if we should fight that. The other pressure that we get is from people who want the tag set to not grow or even to shrink. I get people calling me and saying, that's just syntax, sugar. We don't need a named structure for that. It's structured just like a section. It uses the section model, just call it a section. We don't need a tag for bio. It's a section of type bio. We don't need a tag for introduction or in the book world, professor forward. Those are just sections. Call them sections. Call them book parts. You could do that. In fact, one of the things that we talked about at Jetscon last time, which I guess makes it Jetscon 2012, was sort of refactoring Jets. There were a couple of conversations that were about it. I actually spent some time thinking about it. If we want to make it as generic as possible, I think we could encode everything in Jets in about a dozen tags with about 150 attributes. I don't think we would have improved much. I think we could also do it with about a dozen tags and about six completely open Cdata attributes. I know we would have accomplished nothing because nobody would be able to use those things consistently and we wouldn't have interchange. But we would have a much smaller tag set. I think the people who keep pushing on us to make it smaller haven't figured out that there's actually value in richness as well as smallness. Another conversation that I find myself having with Jets users is the, should I be using Jets at all? Should I use bits instead? Am I allowed to use Jets for this kind of information? Would it be okay with you if I don't use Jets for something? I don't understand the presumption of religious loyalty to a tag set. If it works for what you're trying to accomplish, then use it. If it doesn't work for what you're trying to accomplish, find something that does. If you have a vendor who is pushing you to use a tag set in a way that doesn't work for you and what you're trying to accomplish, find a different vendor or tell this one that this tag set doesn't work for you and if they can't find a way to work with you, you're going to find a different vendor. You don't have to use Jets for everything. We also have people who get anxious about using Jets for things that aren't exactly journal articles. It's the journal article tag suite. Am I allowed to tag posters with it? What about conference proceedings or textbooks? Isn't that like against the law? There is no law. Is it convenient? Do it. Does it work? It works. If it doesn't work, find a way to make it work. This is a tag set for goodness sakes. It's not a religion. We find people using Jets for a lot of things that aren't journal articles, particularly in environments in which they have a lot of journal articles because they understand it. They know how it works. They like it. They want to mix their nonjournal things into the same databases and the same search systems as their journal articles. They want to search them in the same way. They want to store them in the same way. As they put their tractor manuals into the same tag set as they put their journal articles, because they don't know whether the thing they're going to be looking for next time is in a maintenance manual or an article about how to maintain the tractor, it's just information. They want to tag it consistently. I get calls these days. Would it be better if I used bits than Jets? Why do you think it might be better? Because it's newer. True. Does it work better for your content? Probably not. Then why are you asking the question? Well, because shouldn't we be moving to bits because we used to use Jets? No. If it works for you, it works for you. I don't understand why I have these conversations and the reason I'm bringing it up at the beginning of this meeting is as you start having conversations with each other over the next two days, I want you to think about the difference between tagging fashion conversations and tagging productively conversations. At previous Jets cons, the majority of the conversations, in my opinion, have been about how do we actually do things that actually work? They've been what I think of as productive conversations. But from time to time, we've gotten sidetracked into what's fashionable. I'm asking that you not think about that. If the content that you want to tag and mix in with your Jets document is the text of the pros on the bus wrap that somebody is trying to manufacture, do you know what a bus wrap is? A bus wrap is a huge tube of plastic that a typically city bus gets wrapped in and then shrink wrapped on with heat so you've got printing all over the outside of the bus. Is this something you want to be able to search? Is this something important to keep with your archive? Then there's nothing wrong with tagging it in Jets. Do I know of anybody who has written an application that will take a Jets article and lay it out as a bus wrap and print it on that plastic? No, but if you know of one, I'd love to hear. It sounds really cool. There are helpful people out there who call fairly regularly or send email to various lists or whatever pointing out errors in Jets and the Jets documentation. I really mean it when I say those people are being helpful. I am one to encourage you to do that. Nobody claimed that stuff was perfect. Nobody thinks it's going to be. If you find things that are wrong, tell us about it. But be aware that if what you mean by wrong is the example in the documentation does not match the guidelines of the vendor to whom I am trying to supply this data, that might not be an error. There are more than one way to tag a lot of things in Jets. If you want to minimize that, use the authoring tag set. Oh, how many of you use the authoring tag set? Yeah, that's what I thought. There's more flexibility in blue than in pumpkin. There's way more flexibility in green than in blue. People who want to receive documents frequently don't want to have to deal with all the possible variations that the tag suites allow. So they publish guidelines or local profiles of Jets. The Jets standard is not any of those local profiles. And I don't believe it's going to become one. So don't be all that surprised if a local profile you want to use does not match, is a subset of the Jets. More irritating than that, if you want to send your Jets documents to two or three different places, you may be challenged to discover that they have three different local profiles. Maybe you can get them to talk to each other. Maybe you can get them to reconcile. Maybe you just better figure out how to make your Jets data into what all three of those people want. That's imperfect, but it might be the requirement. I don't believe I've answered any questions in the last however long I've been talking. I think I haven't. But what I hope I have done is raised some questions. I hope I have got you to think about what the role of Jets is, what the future of Jets ought to be. I would like in the next couple of days for you to think about and talk about the directions that we ought to be going. We have a lot of speakers who are going to be talking about something they have accomplished with the Jets. I think of them as how we have done it good at my place papers. Those are really encouraging. I like those. In addition to the how we have done it good at my place papers, we are also going to have some what I want to do papers or perhaps what I think we ought to do papers. Let's think about those in terms of who this whole community is, how it would work for that community. In discussion, let's look at the directions that we want to be moving. Questions or comments? Jeff, I bored them to tears. Good. Nice.
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JATS does not actually claim to be a "one size fits all" specification. However, many information content consumers (libraries, archives, on-line services) accept only content that is valid to one of the JATS models, and in many cases specify a subset of the model defined in one of the JATS instantiations (Archiving, Publishing, or Authoring). Thus, content creators find that their vendors and tools often assume that they will be using one of the JATS models "out of the box". This can present a real problem when a publisher has, and wants, information that is not modeled in JATS, or is not modeled in the JATS DTD their vendors and publishing partners require. In this case, the publisher has several options: Drop the inconvenient information; use "Custom Metadata" , hide the inconvenient information in prose, abuse a tag, suggest a modification of the standard, or modify the tag set to encode the information that matters to you. None of these options are ideal, and which to choose in large part depends on circumstances.
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10.5446/21560 (DOI)
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So, das ist immer wieder. Ich habe gerade schon gehört, dass die Autoren der Kalkscheune einer Blogstudie gerade gelünchenmoppt geworden war. Gabs Tote, weißte jemand? Anscheinend nicht. Das nächste Thema finde ich sehr interessant und dazu möchte ich mal eine Frage stellen. Jetzt bitte mal ehrlich, wer von euch ist auf Facebook? Da sage ich mal 99% Verbreitung. Wer von euch vertraut Facebook? Okay, da haben wir ein paar Mutige und so ähnlich ist auch das Thema, das jetzt kommt. Jillian C. York, arbeitet für den Bergmann Center und wird eigentlich in San Francisco in ein paar Wochen für die Elektronik Frontier Foundation arbeiten. Und sie wird über die sozialen Medien und sozialen Medienplattformen sprechen, mit den Kontexten, die sie nachdenken werden und auch die Menschenrechte, die sie haben. Also, ich denke, das wird ein sehr interessantes Gespräch sein, besonders über den Dreibe zwischen eine Anleitung und eine Anleitung. Bitte eine Wohnhand zu Jillian C. York. Hallo. Ich bin froh, dass er meine erste Frage hat, die zuvor ging, wie viele von euch auf Facebook sind. Ich habe die zweite Frage gesehen, wie viele Leute Facebook vertreten. Meine Hand war auch auf. Du kannst es nicht sehen. Ich habe es nicht gesehen. So, ein Jahr ago habe ich dieses Papier geschrieben, die Polizistik und die Quasi-Public-Sphere. Der Link zu dem Papier ist da oben, wenn ihr es anschaut. Es ist relativ lang. Und die Grund, warum ich in diesem Thema interessiert habe, war, dass ich seit dem Zeitpunkt viele Freunde aus dem ganzen Welt, ich bin auch Teil der Global Voices-Kommunität, die in der letzten Präsentation war, und viele dieser Leute waren mir zu mir und sagte, Facebook hat mein Account weggenommen. Und dann würde ich auf YouTube hören, dass mein Account weggenommen hat. Und ich beginnte, in dem ich interessiert habe, in der Investigation, warum das so auf einer großen Stelle passiert. Und was ich fand, war, dass es wirklich die Art der Polizisten-Kontent, auf diesen Social Media-Sites, die das zu passieren hat. Entschuldigung, für nur einen Moment. Ich bringe meine Noten. Da geht es. Excellent. Okay, so, wir denken auf diese Faces, Facebook, Twitter, YouTube, Flickr, alle diese verschiedenen Social Media-Sites. Wir denken auf sie als die Publikum-Sphere. Wir schreiben über Politik, wir schreiben über unsere Lives, wir schreiben über kontroversialen Subjekte, based on assuming, dass wir die gleichen Protekten von freier Spiegel haben, die wir in unseren eigenen Ländern haben. Und so, in den USA, als die meisten dieser Unternehmen sind, die ich im Moment überwenden, wir betreffen, dass wir von der ersten Ämter betreffen. Und viele andere Länder, das auch, weil diese Unternehmen in den USA existieren. Aber diese Spiegel sind alle von privaten Unternehmen. Und so, diese Unternehmen sind allowed, ihre eigenen Räume zu schaffen, ihre eigenen Standards zu schaffen. Ich meine, sie können was machen, was sie wollen. Wenn sie nicht was sagen wollen, dann nehmen sie sie. Wir haben in ein paar verschiedenen Karten gesehen, wo Dinge, die normalerweise betreffend sind, die sicherlich betreffen, von verschiedenen Plattformen, weil sie es nicht liebten. Ein wirklich gutes Beispiel ist auf Facebook, dass Frauen, Fotos von den Breztenfühlenmölden, die diese Fotos posten, vielleicht auch beautiful Fotos, mit denen, wer sie mitgekommen haben, mitgekommen haben, und Facebook hat entschieden, dass eine Mutter, die Breztenfühlen ihrer Kinder, eine Brust betreffend war, beim Ausdruckerloseball, WH 유 Ben N pinpoint, genau etwa. Was die Brust betreffend ist, weiß man im Spiel eigentlich. Nżej Síng Bergging Tigers York weiß es nicht, und den Ein paar Wochen remedies ein Hauskurs萬 Ämter B permis Sta Gym Motor AP Christy was sie denken ist freie Spiege, und dann pressen sie die Unternehmen. Wir haben das gleiche mit Wikileaks im Dezember 2010, wo Senator Joe Lieberman in meinem Land in der US, Amazon für Amazon zu beună lass uns sanden. however, uses the similar method to look at content, and that's community policing. And so what we see is, you've got content on a site, any content, any sort of speech, and you've got a set of terms of service. And what happens is, if I see something that I find offensive, I can then say, report. And click a little button and explain why I'm reporting it in some cases, and other cases just flagging it. Und das Content either comes down or goes into a moderation queue for a human to look at, or it stays up. Now, each of these sites have a different method for doing this. We saw in Craigslist a few years ago that Craigslist, I don't know how popular it is in Germany, but it's that site where you can put up apartments or find things to buy, et cetera, et cetera. On Craigslist, you could just click the flag button and the content would go down if enough people had done that. There was no sort of human moderation involved. It's a little bit different with these other sites, Facebook, and I just realized that my slides not up there. I'm sorry guys. Technical difficulties. Yeah, it's not, I can't get it to work. Sorry. Oh, we're fine. There we go. Okay, so what am I doing wrong? There we go. Hmm, I see. Okay. Okay, there we go. Yes, thank you. So, this method of community policing works differently. It has a mind of its own. It works differently on each site. I'm just going to run down the different ones and what we know about them. So, on Twitter, Twitter doesn't like to take down your content. This is good news. How many people are on Twitter? And how many people trust Twitter? Okay, definitely more than trust Facebook. So, on Twitter, they don't usually take your content down. And in fact, if you do find content that should be against their terms of service, you go through this lengthy process where you find the terms of service and then you find the Twitter system and you go through and you type in your Twitter name and you explain the situation. Most of the time, they will come back to you and say, sorry, we don't moderate our content. Kind of cool. I tested this out, actually. I went and I reported a whole bunch of different things from the truly offensive to the defamatory to the, I'm sorry, Twitter, if you're listening, I did this, to the, you know, kind of somewhere in the middle, they didn't take any of it down. So, in a sense, this is great for free speech. On the other hand, you can see the implications if something genuinely offensive or illegal was put on Twitter. But then again, Twitter is just speech. There's no photos, no videos. So it's a little bit different than the other systems. Blogspot doesn't take a whole lot down either. But they have had a few instances where they've taken down copyrighted material. And as you know, that's a huge debate both here and in the US. Flickr, I'm going to get to that one in a little bit. But their moderation system is actually really sort of innovative compared to the others. They have some automated systems in place where if you post nudity, for example, it goes into a special queue for nudity, where people, then staff members, then manually look at it and determine whether it's able to be put on the Flickr site. So pornographic material cannot be posted on Flickr, but a naked baby, totally fine. But you need human eyes to look at that, because there's no way an automated system can tell the difference between porn and babies, presumably. Then you've got YouTube, where they've been really great about telling people to provide context on the system. So if you upload something, for example, what we've seen recently in the Middle East, if you upload a video that's graphic, this has been happening in Syria and in Bahrain, where people are getting shot and it's being captured on cell phone cameras and on flipcams and what have you, people are uploading those videos. Now, if YouTube sees the video and it doesn't have any context and no tags and no explanation of what's happening, they'll probably remove it. But if you add, this is, you know, what's happening in my country is a massacre and this happened in X-City and you put some tags that are absolutely relevant to the situation, Flickr will most likely keep it up, YouTube, sorry, will most likely keep it up, and I'm going to get to that in a bit in more detail. So, here's an example, I don't know how, yeah, okay, it's pretty clear. Here's an example of how this works on Facebook. So, you've got all of these different options. This is what happens when you try to report an individual person's page, and I think I blacked out his name. You can choose to remove them as a friend or block them. So, if you realize that what they're posting is not against the rules, but you just don't like it, that's what you should be doing. But then you've got these other options where you can report somebody as having an inappropriate profile photo or an inappropriate Wall post, or that they're harassing or bullying. Once you click on those and you get into more detail, you can also report somebody for using a fake name. Let me get to that in a minute as well. So, in theory, this should work. If I saw something pornographic as a profile photo, you don't really want that there. You've got kids on the platform. You could click that. Probably Facebook would take it down. They probably wouldn't delete that person's account. But, these systems are completely rife for abuse, and we see this happening more and more frequently. Now, I'll get to the different ways that this is abused, but first I want to get into their rule about real name. I don't know how well you can read this, but Facebook has a rule that states that users must use their real names. Now, it can be a portion of their names, such as a nickname. So, I'm Jillian, but I could do Jill York. But, you absolutely cannot on the Facebook platform use a pseudonym. Now, I'm going to ask a controversial question. I hope nobody from Facebook is here. How many of you use a pseudonym on Facebook? I don't. Okay, cool. We got a couple. You're breaking the rules. Yes. No, I don't care. I'm not going to report you. But, what happens is, why would you report somebody for doing that? I'm not really a rule enforcer. I'm not the police. What's the purpose in doing that? The problem with this system is that there is no really good reason to report somebody for using a fake name, unless perhaps they're impersonating you. But, some people have discovered that by using this report feature for the real name issue, they can get profiles that they don't like taken down. And so we've seen this with a bunch of activists. A really good example here is Michael Antie. I assume many of you know who he is. He's a prominent Chinese dissident, activist, and he used to report for the New York Times. Now, his... Oh, did it again. There we go. Michael Antie. So, Michael Antie is not his real name. He was born in China. His real name is a Chinese name that I can't even remember, because he doesn't use it. He uses the name Michael Antie. It's been his pseudonym for over 10 years. He used it at Harvard. His Harvard email address, that's where he studied. His Harvard email address is Michael Antie at whatever. He used it when he wrote for the New York Times. But Facebook says no. Facebook says no, you must use your real name, because we want to make sure that people are being authentic on our site. So what this means for Michael is that he's got some enemies, right? He lives in China, where he speaks out about the Chinese government, and people have chosen to report him. Of course, Facebook, for their part, decided to verify this. And what they did was they went to Michael and asked him to send in a copy of his government ID via email. I hear laughter, and I understand why. That's ridiculous. It's completely inappropriate. It's completely unsafe. And they don't even acknowledge that this is happening. So, Michael, of course, could not verify that his real name was Michael Antie, because it isn't, and was thereby kicked off the Facebook platform. You will notice, though, that he does have a different profile. This is allowed to stay up, because it's a page and not a profile. Very important distinction. Facebook has said, if you want to be on Facebook, but you need to remain anonymous, you should do this. Why? I don't get it. On the other hand, they do make a pretty compelling argument for why real names are important. I don't know if I agree with it, but this is what they've said. They say that activists have come to them and say, no, we prefer that your users have to have their real names, because it makes us feel safer. That means that the secret police, et cetera, et cetera, can't get on the site, create fake profiles, and get into our information and trick us. Now, that's a good point, except it's completely false. That's Santa Claus. There's like 500 of them on Facebook. Yeah, really. Facebook has this system in place, and they say that it's very important for maintaining civil discussion and for maintaining authenticity. Mark Zuckerberg has even said that it is a sign of a lack of integrity to have more than one identity. Well, maybe in the US. But what about activists? What about people in Egypt, Bahrain, Syria, Tunisia, where being completely public about your activism is not necessarily safe? Nope. We're not there yet. Oh, my goodness. Okay. I'm going to move on to a different example. And... Sorry, guys, I'm really bad at this. There we go. Okay. This is a completely different case. This has nothing to do with the real name issue. This is the case of a Tunisian anti-censorship group called Zayabzala. And that basically means leave our internet alone. It's Tunisian slang. Now, this group was started sometime last year, I think, to protest against the heavy internet censorship that was happening in Tunisia. Now, sometime midway through last year, I get an email from my friend. You might know him. His name is Slim Mamamo. He's in the Tunisian ministry. He emails me and he says, hey, I'm having a problem. One of my friends is the administrator of this group. And he can't update the page anymore. It's gone. Page is still there, but he can't touch it. What's happening? I probably shouldn't tell this story publicly, but I'm going to anyway. So, I wrote to somebody at Facebook and I said, hey, what's going on? Why is this happening? And they said, oh, that's too generic of a name. Okay. So, they wrote to me and they said, our customers have said, or our users have said, that they don't like it when there are pages that are too generic. For example, there shouldn't be a page for pizza. Okay. I mean, yeah, maybe pizza shouldn't have a page. I get it. How many people are going to sit there and like pizza? But the problem here is that, first of all, I mean, this is Arabic, but it's not Arabic. It's Arabisi. It's this language that people use to type. That seven is like a huff sound. So, it's not clearly Arabic. But it's not English either. So, really, who at Facebook is making this decision? And do they even know what it means? Now, I didn't get an answer on that one. I don't even think I asked it. But what it came down to was, hey, this is a popular thing in Tunisia. People there know what this means, just because you people at Facebook don't. You know, doesn't mean that you should be taking down the site. In the end, they left it up. People got to use the site. It's still there. You can look it up. I think that's actually spelled differently, though. Okay, here's another famous example. You'll love this one. I'm sure everyone knows who that is by now, right? Wa'ilkou'nim. Now, he became really famous in Egypt after the uprising there, because he'd been arrested and then he was released. And then the news came out that it turns out that he had been, you know, sort of behind the Egyptian Revolution. Now, that's obviously a very hyperbolic statement. But he did do one really important thing. And that was that he started the group, we are all Khalid Said. Now, this was this Facebook group that had been set up sometime back in 2010 after Khalid Said, a young man from Alexandria, was murdered at the hands of police. So this group had become pretty popular. And back in November of 2010, before any of the revolution started, the page went down, disappeared. Over Thanksgiving weekend in the US is when this happened. And as you can imagine, that's the time when most of us are with our families and not online, except me. I mean, I was online. And so we heard that the page was gone. And we were getting these emails from friends in Egypt who were angry and saying, what's happening here? Why is the page gone? I don't understand. We didn't break the terms of service. Our page is very civil. As it turns out, Wael himself had been using a pseudonym. Somebody had reported him. And his account had gone down, taking the page down with him. So not only will Facebook deactivate your account, but anything associated with it as well. So in the end, we got it back up. But, and when I say we, I'm talking about a loose sort of consortium, not even consortium, a loose sort of group of friends who happen to be activists, who happen to work in the space, who happen to have friends in Egypt. There's a lot of other people involved. I certainly don't take credit. But eventually we got it back up. But Facebook insisted that someone else take on the job of administrator. So Wael transferred it to a friend of his in the US, an Egyptian friend, and she then became the administrator of the page. And then it went through some other hands as well. But so that's another case where really, really important speech, not protected on Facebook, because of this silly rule. Okay. Here's one of my favorite examples on Flickr. A few years ago, this photographer named Martin Dorse, who's that Dutch, I think, that sounds Dutch, right? Yeah, we'll just pretend. He had taken this photo in Romania of a young boy smoking a cigarette. Flickr, obviously, for good reason, has a rule against posting photos of minors drinking or smoking. Okay. I get that. I mean, even though minor has a different rule, I mean, I know in Germany you can drink it, 18, 16, I don't know. In the US it's 21, ridiculous. But obviously 10-year-olds can't smoke pretty much anywhere. Well, Flickr decided, probably after community reporting had happened, that this photo should be removed. They didn't just remove the photo. They removed Martin's entire account, which he had paid for. So, pro account on Flickr cost 25 US dollars a year. Gone. All of his information, gone. No warning, nothing. He protested, as you can see, this was part of the protest, no censorship with the censored cigarette. He protested, and actually successfully. So the good news was, after he wrote to Flickr about the situation, Flickr said, okay, you know what, you've given us some context. This photograph is obviously depicting a horrible situation that's happening in another country. Children smoking, that's terrible, will allow it. So he posted it back up, titled it The Romanian Way. I'm not really sure why. I get it. So, the photo is still there, so that's the good news. And actually, I would say about Flickr, that they've actually improved their processes since then, and created a set of robust community guidelines to help people with, you know, what kind of content can be up there. So, for example, their community guidelines say things like, do play nice, and do moderate your content. Link back to Flickr when you use a Flickr photo on another site. All good rules, not legal terms, not like the really long, archaic 27-page terms of service, like on iTunes, but simple rules for users to follow. There's also a set of don'ts. You probably can't read that from there, I'm sorry. Things like, don't show nudity in your buddy icon. Pretty reasonable. Don't forget the children. We love that one, don't forget the children. No. Don't be creepy. It says, you know that guy, don't be that guy. And then you've got a whole bunch of other ones. Well, so although these are clear, pretty clear, they're not perfect. And there was a recent case that sort of illustrated that. Arabaoui is an Egyptian activist, journalist. His real name is Hassan Mammalawi. He had a paid Flickr account, a pro account. And he'd been using it for years to document protests. He used it when he was in the US to document things there. Just a really good comprehensive Flickr account. I was a fan. I used to look at the photos all the time. And what happened in this case was, I'm hoping I'm going to get this right, because I know that there are Egyptians in the room. After the revolution, Egyptians were able to break into the sort of security apparatus and steal all sort, sorry, take back all sorts of documents about them. So there had been all sorts of things that had been kept over the years, files on individuals, on activists, even on non-activists. One of the things that was obtained during that seizure was these three CDs of photographs of security officers. Hassan got a hold of those CDs and decided that he was going to post them on Flickr. Das ist ein ziemlich braves Ding zu tun, besonders wenn Dinge nicht total sattelnd in Egypt sind. Wir sind noch so etwas in der Demokratie zu tun. Und so, mit diesem Sattel, hat er sich entschieden, dass es den Risiko wert wäre. Er hat diese Fotografie auf Flickr posten. Er hatte viele Details, Informationen, über was er machte. Er hatte auch eine explizitere Erklärung, wie er die Fotos obtainte und was er mit ihnen machte. Und als Result, Flickr hat sie sie aufgenommen. Warum, fragst du? Weil Flickr hat eine Regel, die sagt, nur posten Content sei dein. Das ist nicht ein copyrightes Problem, weil wenn es ein copyrightes Problem war, hätte jemand die Digital Millennium Copyright Act in der yoursch-aut stability volcanunu ver Paper er Das hat auch mehr unlike some companies I might mention. Facebook. Excuse me, little frog. So, he, you know, so, Flickers Human Rights Director, her name is Abelé Okobi Harris, she was actually on a panel about this same subject with me at South by Southwest, really, really wonderful woman, and she has done a lot of thinking on this, and wrote in the post that she's open to ideas about how they can change the rules, or maybe create a different system for activists, and for human rights activists in particular. So, that's great news. I mean, Flickers actually opened to hearing different ideas, and if you, I didn't post the link, but if you look for that post, you can see in the comments section that a number of pretty well-known human rights activists have jumped in and shared their ideas. One was from the organization Witness, and he had shared a different way that Flicker could handle this kind of content, and so I'm hoping that there will be more discussion on that going forward, and an einem Beispiel of a company that really is kind of trying to do the right thing. But at the same time, should they have taken that content down? I don't think so, but I understand where they're coming from a little bit more than with some of the other examples. YouTube, YouTube, how many people use, or not use, how many people upload videos to YouTube? Okay, pretty good number. YouTube. YouTube ist similar to Flicker in that they've been really sort of conscientious about creating context around content. There's this organization, Nauat, maybe you've heard of them, they just won like 10 awards for everything. They're really awesome, they're a Tunisian blog collective, and they have been, they've been working in Tunisia for years against Tunisia's censorship and all sorts of other different issues. One thing that they did was they uploaded a video of some Tunisian kids, children sniffing glue. Now, just like with Flicker, YouTube has a rule that says that minors cannot, minors smoking or drinking cannot be posted on their site. I get why they do this, I don't know if any of you have ever seen those videos that managed to kind of slip through the cracks of teenagers being drunk, and I mean, you don't really want that in their, in perpetuity. So, in this case, YouTube took down the content because it was against the terms of service. And once again, Nauat went back to YouTube and said, hey, wait a minute, we're doing this to show the dire situation of street children in Tunisia, this is really important, please. And so YouTube said, okay, we'll put it back up. Now, I mentioned before something about graphic material on YouTube, especially in recent months, how people have put up different videos showing real true horrors, deaths at the hands of police, and dead bodies in the streets, really horrific stuff. Sorry for the picture. But this is YouTube's solution to that problem, which I think is a really good one. So, you probably don't want to be sent a bitly, a short link, and then click it, and all of a sudden see somebody dead on the ground. That's not exactly an idea of a good time. And it's kind of awful, especially at work, you never know. And so what YouTube has done is they've put this interstitial, where when you click on a video that contains that kind of content, first you have to log in to the site using your user account, and second you have to click a button that states that you are 18 and that you want to see this. And so this says, that's the name of the video, and then it says this content may contain material flagged by YouTube's user community, if it's inappropriate. And then it says to view it, verify that you're 18 or older, and if you would instead prefer to avoid this kind of content, activate your safety mode. So, I think this is a great solution to a really tricky problem. Something that's adult content should be seen by adults. I don't believe that it should be blocked or taken down, but providing a warning is a really good way of getting around that problem. I wish ISPs would consider the same instead of blocking things. All right. I see we're at about the halfway mark. Excellent. Oh, not yet. Eh, we'll just leave it up. Okay. Maybe we won't. That's kind of awful to look at. There we go. So, I gave this talk, as I mentioned before, at South by Southwest last month on the same subject. It was a panel discussion with some really great people from the Committee to Protect Journalists, from Yahoo, and the very awesome and famous Rebecca McKinnon who does a lot of this same work, but on Chinese platforms and on American ones. And it was illustrated, which is kind of cool. We talked about building human rights into your social site. And really, to me, that's the problem. Is that a lot of these platforms aren't considering the implications when they restrict what you can post on them. And so, as I've mentioned, there are all sorts of different rules that cause these takedowns and account deactivations and removal of content to happen. But there aren't really any... Some of these companies aren't really listening as to how to fix this problem. I'm just gonna go through a few examples without any slides. One, I talked about Facebook a lot. But one of the other issues with Facebook is if you go to their Terms of Service at the bottom of the page and you click on it and you try to change the language from whatever language you're using, it's only available in seven languages. I'm not even sure German's one of them, actually. Does anyone know? No? Okay. So, Arabic is definitely not one of them. I will tell you that. So, what this means is, you have users who speak Arabic. I think... I don't know how many Facebook users in the Arab world now, but I know that in Egypt it's something... it's some ridiculously high number. So, if it's that high in Egypt, I imagine, that across the rest of the region it's similarly high. You have millions of users on Facebook using Arabic as their primary language. They can use the site in Arabic, because the site's been translated, but they want to know the rules? Nada, they can't get to them. Unless they want to read them in English. So, I mean, it's legalese, right? How many... I can't read... I certainly can't read legal language in any language, but my first, and even then it's kind of tricky. And so, I can't imagine that a native Arabic speaker would find it easy to go and read the Terms of Service and understand the rules. Facebook, like Flickr, has implemented a different set of community guidelines that are a little bit less legal and more user-friendly, but they're really hard to find. I tried last night actually to find them for a slide. I couldn't find them after like 30 minutes. I was like, hmm, this isn't very helpful to users Facebook. Maybe you want to reconsider. And so, that's one case where, really, I mean, they need to be thinking more about who is using their platform. And when I bring it to the who, it's not just who in the world, but also the who of activists. One of my other concerns there is appeals. So, I've talked about all of these different situations where somebody's content has come down and they've either managed to get it back up or not, but they've communicated with the company. I think you'll probably notice a theme there, that people like myself, intermediaries, sort of, always had something to do with getting that content back up. Most of these sites don't have robust appeals processes where you can go and say, okay, I think that my content's been taken down an error, could you please put it back up? Most have no options. And in fact, with Facebook, if they take your content down, they're going to send you an email that says, this decision is final and cannot be appealed, even if it can. Ridiculous, frankly. And so, that's another issue where people, not just activists, and I emphasize activists, because I think that's where a lot of these issues are happening. I realize that the rest of us are subject to these somewhat inane rules as well. But the reason this is so crazy to me is that I think that there should be some sort of process, some sort of way that you can go to a site and you can say that you want your content back up without having to go through an intermediary, without having to reach out to a high level director at a company, which not everyone has access to. And so when you see these things going back up, you see these examples of really well connected people who have some sort of connection to staff members at these companies and can do that. But that's very few of us. Another good example actually happened a few years ago, I think 2007. The Egyptian blogger and video blogger, Wa'el Abbas, had captured videos like three, four years ago of police brutality. And he posted those to YouTube. And this is when YouTube started to change their processes a little bit. But he posted them to YouTube. And I think it took him weeks to finally connect to somebody in YouTube to get that stuff put back. And that is when Google, which owns YouTube, had started thinking about how they could better implement human rights-related policies on their platform. And since then they've gotten a lot better at it. There are some sorts of networks that are working hard to kind of enforce these issues. One that you might have heard of is the Global Network Initiative. You've got Google, Microsoft, and Yahoo, they're all part of it, along with academics, investors, and NGOs, including some of the biggest human rights organizations in the US. I don't remember if there are any outside of the US. I'll look. But it's called the Global Network Initiative. And you've got Human Rights Watch, the Committee to Protect Journalists, the two organizations, the one that I'm leaving and the one that I'm going to, so the Berkman Center and the Electronic Frontier Foundation, and all sorts of other folks involved in this organization. But the problem is, that's only three companies. And so although those companies are held to a certain set of standards by the Global Network Initiative and its partners, you've still got all of these other companies, both big and small, out there in the world, that aren't held to any sort of standard at all. And the other issue there is that we, as users, are very unlikely to quit. I mean, so I've known about this issue with Facebook for probably two years now. Do you think I still have a Facebook account? Guilty. Same thing with Amazon. I'm almost ashamed to admit this one. But I was like, I'm in a boycott Amazon. They took down WikiLeaks. I'm so mad. And then I was like the next day, I'm like, I need a book. So, I felt terrible. I shouldn't have admitted that. Please don't throw tomatoes. I don't know how many of you boycott Amazon. So, the thing is, there's no large-scale action happening to keep these companies in check. This has gotten a little bit more media attention lately. And I think that has a lot to do with the fact that I am just incessant about tweeting and calling journalists and being like, hey, talk about this please, it's important. But I also think it has a lot to do with how badly some of these companies have been behaving lately, particularly in light of the revolutions happening really everywhere. And so, you know, it's really hard to get the companies to listen and they really have no reason to. So, with this, I'm going to get close to concluding and then I'll leave a little bit of room for questions because I think we have an hour set. And if not, then I'll just run off. So, there are some solutions, they're not great, but help me get there, really, get involved in this. So, one solution is that these companies, frankly, should be considering human rights and considering, not just human rights, but considering how their users are utilizing the site when they make the rules or when they amend the rules. So, you know, constitutions, for example, are written, but then they are often amended as things change, as laws change. Okay, I couldn't vote 100 years ago in my own country, but that's why we have amendments. You don't see these companies amending their rules very often. And so, they need to be looking at what users are saying, what they're doing and how they can fix this problem. Another solution, you know, better community guidelines, that's an obvious one. Some of these companies, like I said, are trying to do this, but I don't think they're there yet. Another question that I have is, is community policing really the answer? I mean, look, if I'm famous, if I'm a Chinese, let's say I'm a Chinese human rights activist, chances are, like I said before, I have a lot of enemies. And same thing if I'm famous, if I'm Lady Gaga, and by the way, Facebook has said that Lady Gaga cannot be Lady Gaga on Facebook, she has to be Stephanie Germanata. Very important, you know, just in case you didn't know who she was. So, you know, that's... I lost my train of thought, that's great. But that's one of those things where, really, Facebook, look at how people are using your site, look at what's important, flip it around, change it, make it accessible to users. And community policing, if you're famous, or if you are an activist, chances are, you're more likely to be reported than if you're just some regular Joe, who's going on Facebook as Santa Claus. And so that's really important, that these community policing efforts really sort of skew toward the well-known. And so in an unfortunate circumstance, that I think that these companies need to be looking at and amending. And then, of course, the most important is, look, community policing is probably the only scalable method for a company with 500 million users like Facebook. I don't think there's anything else that they could do. And I think that an automated process, at this point in technology's lifespan anyway, would be problematic, even more problematic, than letting users do the work. And so I think that's where the robust processes, appeals come in. And it's really important to have an option for appeals. And if there are any people out there in the room building social media sites, this is what you should be thinking about, all of these different factors. And so that's pretty much where I stand on all of this. I would love to open this up to questions if anyone has any. I'm also full of more examples if you want more. But is there anyone who'd like to ask questions? Okay, cool. I'm going to drink some water while you do that. Simon, is that you? Hi. Hi. My question was, you have very nice solutions there. But they are solutions to be implemented by a certain Facebook, which, as you said, has basically no reason to do that. So what about government action to force social network operators to actually implement something like that? And what about, especially, I think it was Dana Boyd, who proposed just having social network like utilities, like streets. So why not that? That's a really good question. So there's two issues there. One is government regulation. And the other is treating social media sites like utilities. So I'm going to address them in order. The first one on regulation, there's an Act in the US that's been proposed and never managed to pass, the Global Online Freedom Act. And I believe, and I'm not an expert on this, but I believe that there was some sort of provision there for companies to add things like this into their corporate responsibility. And I think to that, I'm just going to add another sort of tangentially related point, which is that it's not just the social media sites that are really kind of screwing up in this space. I think that there are other companies that are doing even worse. So you've got a lot of American companies that are actually behind the filtering, the internet filtering censorship, the blocking websites. It's a lot of American companies that are behind the filtering in China, Bahrain, UAE, Saudi Arabia, Tunisia. I could go on like this for like, you know, two feet, two hands. It's US companies that are doing that. And so I think that, yes, I think that there is perhaps a role for the US government in this space to enforce certain things. Now, that's also tricky, because you could really add anything into it. So, one of the things that's been there is that some of the rules, I mean, I hate to say that I don't trust my government, but does anybody trust their government? Then you can be adding things into the rules that just like in many other countries would restrict certain types of speech, and that's my concern there. And so I don't know where I stand on that one. The second question though, which was, ah, utilities, thank you. So Dana Boyd, who I'm sure many of you have heard of, and she was touched off as well, and she was actually kind of one of the early people to focus on this issue as well, she suggested that the government regulate Facebook like a utility. Now, that's kind of a tough one. I mean, I think that's where we come into the title of this paper, which I wrote, which is called, you know, Policing Content in the Quasi-Public Sphere, because we're talking about a space that the former town hall, the town square, the public space outdoors, is now Facebook, Twitter, Blogger, et cetera. So, in this case, there's precedent for this. You've got the example of the company town, which some of you might have heard of, in the US there have been a number of cases in the past where, for example in malls, in a shopping mall, you can't just go into a shopping mall with a T-shirt that says, oh god, I need a good example that doesn't have profanity in it, F-Bush, right, like President Bush, you can't just walk into a mall with a T-shirt that says that, you know, chances are you're going to get kicked out, but there are people who have contested things like this, and there are a few different cases where they successfully contested things like this in, you know, states, so it's not a nationwide federal legislation. But one of those things was anti-war protesters handing out pamphlets in a shopping mall, they took that to court and they were able to do that. And, you know, I'm not a lawyer, so I'm terrible at legal language and talking about this stuff, but that was a case where, yes, I mean, they managed to win that, right? And so I do think that there are cases for regulating these sites, but I don't know if the utility example is the best one. Tough question. Any other questions? Yeah, we are. First this side, then this side. Not well. Thanks for your talk, very interesting, very intriguing. So, we set that all these appeal cases should be looked at eventually by human beings. Do you have any insights into what resources Facebook and so on spend on dealing with these appeals? 600 million users must be enormous amount of work to actually look at all the appeals. Right. So I don't know with most of these companies because most of them are very private about their systems. Facebook actually won't give me straight answers about any of this. So, I don't know what I've said about Facebook. I mean, a lot of it is very factual, of course, because we have evidence, but a lot of it I don't know what happened in the background to cause things to happen. In terms of resources, what these companies put into this. I mean, I know that Facebook has a dedicated team in the US that handles English language content. I know that their Arabic team or person, I think they might only have one, I don't know. They have a very small Arabic team that's located in some places in Dublin, in Ireland, like, okay, really? There's a lot of Arabic speakers there. But then, you know, they've got other teams for different language content. I couldn't tell you the numbers, but I do know that there are human eyes looking at all of this. And YouTube is actually a great example. They have a staff member who oversees a whole team in different languages at their San Bruno offices in California. And they have a whole dedicated team that looks at this incoming content. And the person who oversees it, her name is Victoria Grand, she changes the rules when they need to. She looks at all of this. She's the one who sort of reviews the processes. And I've actually spoken on a panel with her, too. And I think a lot of it has to do with the company's orientation toward human rights and toward that kind of leadership. But when you see someone like that in that role, it really makes a difference. But I wish that I could give you a more precise answer. I can't. Over there, we have two questions, I think. One question. So, I totally understand your positions from an activist perspective. However, from my experience, I'm a community moderator in a big online community. And the problem we there have quite often is people trolling and posting inappropriate content and thereby spoiling the community experience for a lot of people. So, where do you see the, is there a way to solve the tension between protecting free speech on the one hand and not allowing the trolls to take over? Yeah. So, I think it's hard to compare any of these platforms to that kind of platform. And the reason is this. If I run my own blog or a community, any of the content that is posted on it is absolutely relevant to me because I'm the moderator, I need to take down that content. So, I would say, not a community, it's a platform. And so, if somebody is on my wall and they're trolling my wall, I can just kick them right off my wall. If they're in my group doing that, I can kick them out of my group. But I don't need Facebook to come in and do that for me because it's my responsibility. So, I think that's sort of where the difference between these two things is. But I do agree. I'm very anti-censorship. I'm probably a free speech absolutist to the nth degree. So, ich habe viele Comments auf meinem Blog, weil ich eine Troll auf mich nicht alleine habe. Und ich denke, wir alle machen das. Und ich sehe das nicht als, wie ich jemanden censere, weil sie das Rest der Internet haben, um es zu sagen. Ich möchte es nicht auf meinem Blog. Ich verstehe, wo du kommst, aber ich habe das gelesen. Danke. Okay, talk to us. Ich kann nicht hören. Sorry. This works. You're looking at the big boys like Facebook and YouTube and the guys who, I would say, as a user, I have pretty much no other choice to either accept that stuff or not. Looking at some smaller communities, if I go in there and put a lot of policies in that, I don't know what happens. People are on earth in the community. So, do you see, or do you have any guidance to balance between tough policies and keep people in? Yeah, that's a tough question. I think Facebook, as I mentioned before, is not going to have a problem. People will stay on Facebook. They're not going to lose all of their users because of this. I mean, there have been tons of boycott movements for Facebook. I mean, there have been, there are people who boycotted because of the privacy policy. There are people who boycotted because they allowed the Mohammed cartoons to stay up. There are people who boycotted the Intifata page that I mentioned at the beginning. When you've got a smaller company, though, I think that you actually, you've got sort of two choices. One is you create the rules for your community. And so you make them designed for whatever you want. So if you're a Muslim community online or a Christian community online, you have to make the rules so that they apply just to your constituents. And you will brand it that way. And that's fine. Like I said, there's a million other places on the Internet. The reason that Facebook, I see Facebook differently, is because Facebook really is the public sphere. 500 million people is bigger than a country. And so it's different than when you've got a small company where they can sort of twist and bend the rules to fit their users. But if that company gets bigger, then they need to consider what users are doing. But I think that that's really important, because I think that Facebook also understands and they're capable of doing the same thing. And so make sure people don't say that there should be some flexibility in changing the guidelines. I hope that answers your questions. Test test? Okay. One question. There is a good reason why there are guidelines in place simply because big platforms such as Facebook, for example, don't want to be political. I mean, once you start to be political and once you start to say, Also, man muss nicht nur Guide-Line produzieren, sondern auch Ethik-Kodex, wenn man sie mag. Die wichtigste Frage ist, ob wir auf vielen Plattformen in dieser Richtung gehen, dass wir von strickem Guide-Land und etwas Ethik-Kodex in dem Füge, wo, zum Beispiel, ich weiß nicht, ein Facebook in dem Füge könnte, sagen, eine Fandpage für eine Füge, für Beispiel, produzieren, dass die Waffen okay sind, wenn es dieses type von Waffen produziert und diese Menschen in diesen Fällen produziert, während die Waffen in diesen Fällen nicht okay sind. Das ist eine wirklich interessante Frage. Zu Ihrem ersten Punkt, das war, oh Gott, ich dachte, ich werde die zweite Frage antworten und habe vergessen, was das erste war. Kannst du mir bemerken, was du gesagt hast? Es war so gut. Ich glaube, das ist ein wirklich guter Punkt. Ich werde ein bisschen eine kontroversche Antwort bringen. Ich verabschiede, wenn ich mich auf jeden Fall verabschiede. Ich denke, das Page, das ich sagte, in dem Anfang meiner Rede, um eine dritte Frage in Tafada und Palestine zu nennen, ist das perfekte Beispiel. Denn beim gleichen Zeitpunkt haben Sie 100- auf 100-Komotionen auf die Waffen für was es ist, israelische Waffen. Sie haben zwei Seiten, und Sie können das mit anderen Beispielen sehen. Ich bringe diesen, weil es so recent war. Sie haben zwei Seiten, die ein Ding ist, und die andere ist ein Ding nicht. Das ist bei Facebook. Ich finde das zu bemerkbar. Das ist das Gleiche, was du darüber gesprochen hast. Ich wünschte, ich habe mich erinnert, was du gesagt hast. Das erste Frage war, oder das erste Kommentar war, dass du, wenn du politisch beginnst, du nicht stoppen kannst. Ja, okay. Das ist wirklich ein Lichtbub. Facebook, eigentlich, hat wahrscheinlich eine sehr gute Reise, nicht politisch zu sein. Das ist, weil sie in China noch geblieben sind. China ist ein enormes Markt. Vielleicht hast du die News gesehen, dass Facebook, und das ist unverkürzt, von Facebook, versucht, das Chinese Markt zu entführen. Aber sie gehen in den Sensor, wie Google das 2006 gemacht hat. Facebook kann sagen, wir sind nicht eine politische Plattform, aber sie machen eine politische Entscheidung, wenn sie in China mit der Sensorinitierung gehen. Ich denke, das einzige reale Incentiv für sie zu machen, ist das Geld. Das ist, weil ich denke, das ist wirklich unverkürzt. Ich denke, dass es ethisch zu sprechen ist. Freie Spiele sind die Nummer-1 Priorität auf diesen Seiten. Das ist meine Meinung. Ist das nicht eine Fiktion? Kann man nicht politisch sein? Kann man nicht politisch sein? Wenn du eine Plattform bist, dann ist das nicht ein Content-Kreator. Ich denke, dass es in einigen Plätzen, in denen die Social-Media-Sites in einem solchen Weg kürieren. Global Voices, das war in der letzten Präsentation, hat Blogs, wir schreiben über verschiedene Dinge. Wir sind nicht politisch, sondern wir kürieren Content. Wir haben eine Beise, auch wenn es auf dem individuellen Author-Level ist. Aber mit Facebook, du sagst, dass eine Plattform, in der anyone virtuell aufhört und das Content aufhört. Ich denke, dass es 100% unpolitisch sein kann. Das ist wahrscheinlich nicht, aber ich denke, dass sie das besser machen können. Wir haben zwei letzte Fragen. Ich möchte euch klarstellen, weil ich nicht verstanden habe, ob das ein humoröser Bemerk war, wenn du das Beispiel YouTube-Flegging-Content benutzt und dann eine Beise zwischen den Menschen, die das heißt, dass es Grafik- und Verwaltungen gibt, oder so etwas. Du sagst, du wünschst, dass ISPs das nicht für Blocking-Solvenz tun. Aber die Infrastruktur, die du für Warnungs-Signen brauchst, ist genau das Gleiche, das du für Blocking-Signen brauchst. Ja, und ich glaube, dass ich das nicht bedeutet. Ich dachte, dass es eine bessere Lösung wäre, dann die Beise zu blocken. Aber ich wünschte nicht, dass es nicht eine gute Lösung ist. Nein, ich glaube nicht, es ist eine gute Lösung. Ich glaube nicht. Das erste Punkt, das ich gesagt habe, und ich war das nicht, war das eine der remixzapo Brigade könnte in einer besseren Kommunikumente in internationalen Kooperationsen in der Entwicklung beinhalten werden? Das ist eine tolle Frage. Ich arbeite jetzt auf einem Papier mit jemandem. Ich denke, das wäre toll. Ich denke, dass es viele Organisationen gibt, die das tun. Die Global Network Initiative ist eine der tolle resources zu erreichen. Es war mega cool! frickums Ambassador Peter Julian, das war toll. Danke. Wann bist du in Berlin? Wann bist du in den US? Ich lasse am Sonntagmorgen. Ich spreche jeden Tag auf Saturday. Ich glaube, dass es viele Leute gerne mit dir sprechen. Das ist so, dass du mich holst. Ich habe nicht viel auf der Internet getroffen. Aber du kannst mir kommen und ich werde hier sein. Vielen Dank. Das war toll.
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Online conversations today exist primarily in the realm of social media and blogging platforms; these spaces that we so often think of as the “public sphere” are, however, privately owned. Instead of a decentralized Internet, we now have centralized platforms serving as public spaces: a quasi-public sphere that is subject to both public and private content controls spanning multiple jurisdictions and widely different social mores. Private companies set their own standards for content regulations, which often means striking a balance between keeping users happy and operating within a viable business model. A fine line also exists in keeping one’s site uncensored by national governments, while still attempting to provide a space for free expression. As private companies increasingly take on roles in the public sphere, the regulations companies must provide, and the rules users must follow, become increasingly perplex. This discussion will focus on case studies from platforms such as Twitter, Facebook, Blogspot, Flickr, and YouTube, and will look at the issues of content regulation, community policing, anonymity, and account deactivations.
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10.5446/21568 (DOI)
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Hi, good morning. I know everyone's maybe a little hungover or tired from yesterday, but I appreciate you coming out to hear me speak. My name is Saru Svarvar. I am an Iranian-American journalist. I currently live in Bonn, Germany. I've just written this new book called The Internet of Elsewhere. It's coming out this month. It'll take a little longer to get into Europe because they still have to put it on ships and send it over. I apologize. If you Google it, you'll find my website and you can order it or ask your local books or whatever. Anyway, I work currently at Deutsche Welle in Bonn, Germany, Deutsche Welle English, so your taxes pay for my job. So thank you. And I host this program called Spectrum. It's in English. It's about Germany and European science and technology. You can check it out there. I've also worked for these other radio programs in Canada and in the US. So my book is about The Internet of Elsewhere. What does that mean? That means that the Internet, of course, that some of you are using right now that we all know and love, it's kind of the same, right? When you use the Internet in Germany or whether you use it in this case Mauritania, kind of your experience is the same. So what do I mean by The Internet of Elsewhere? Well, I mean that the things that the Internet produces are different in different parts of the world, right? So there's a reason that various kind of, you could call them applications, you could call them effects emerge in different parts of the world, right? There's a reason why the Internet itself was born in the time and the place in which it happened, which is to say Southern California in the late 1960s. But I feel like we've lost this understanding, this kind of historical context, if you will, of how the Internet is this kind of thing that collides, if you will, with history and context. We recently saw things in Egypt and Tunisia and now Libya as well, other parts of North Africa and the Middle East, where there was this idea that these were Facebook revolutions and that people were using social media and how great is that? And that's changing the face of the Middle East. You know, but of course, I don't know, I guess I'm a little bit more skeptical about that because as some of you may know, Egypt shut down the Internet for five days prior to Mubarak's stepping down from power. And yet the protests got bigger. So to me, that seems a big kind of check against this idea that the Internet as a concept is an actor in these things, right? That in this case it produces democratic change. We've seen this before in Iran, right? Two years ago, you probably know there was this presidential election, it was very controversial. Ahmadinejad won the election and is now the president, again, of Iran. And there was this idea that people were speaking out against the government and using Twitter, using all kinds of social media, and again, really pushing people to the streets. This was this narrative that was created, I think, in the American media. I don't know how much attention it got over here in Europe. But you know, there was this idea that, again, the Internet is this actor that, you know, changes a country and changes a society. But that also applies to situations that aren't political, right? That applies to development. There's this concept that I'm sure many of you are familiar with, which is called ICT4D, ICT4 Development Information and Communications Technology for Development. So there's this idea that, you know, we see it in projects like the One Laptop for Child or there's a non-profit startup in San Francisco called Invinio, and there's all kinds of other projects, where, you know, if only we bring technology, information technology, mobile phone technology, internet technology, Wi-Fi, whatever, to a place, then we create some effect, right? Then we create economic development, right? So again, there's this idea that the Internet or technology or information technology is somehow acting upon that place. And I'm not trying to say that that, you know, it doesn't help. But I guess I don't really, as I've done research for this book, I believe less in this kind of primary kind of acting relationship. But the thing is, we've seen this idea before. This idea is even older than that. Nicholas Negroponte said back in 1995 that, you know, the Internet will flatten organizations, it will harmonize people, the nation-state will go away, but the nation-state, you know, as we all know, is still very much here. And this is an idea that's even older than that, right? With this quote was taken from a book that I highly recommend you guys read. It's called The Victorian Internet, and it's about the rise of the telegraph around the world. And there was this idea back then, too, that the telegraph, you know, is connecting people and harmonizing people, and that's so awesome. And, you know, and again, like, that didn't really happen. And so, you know, this is kind of what we've been reduced to, I feel like, is like when you have the Internet and you bring it to a place, right, either some kind of change happens, some kind of political change happens, some kind of economic change happens, and that's great, you know. And again, I'm not trying to say that it doesn't help, that it doesn't, it's not good for people to have mobile phones and to have internet access, of course it is. But what I'm trying to show is that it's more complicated than that, and I would argue more interesting than that. So, I took a look at my book at four different countries, as he said, South Korea, Estonia, Senegal, and Iran. So, you might ask, well, why these countries, right? And this is the longer part in my book that I explained how, you know, what I'm trying to argue is that when the Internet arrives in a particular place, it collides with what's already there, right? The Internet doesn't arrive in the same point in a country's history in every place, right? Some people are more literate or less literate, more educated or less educated, have more economic power or less, or have more political freedoms or less. And when it arrives at that place at that time, it does something to the character of the Internet and it emerges really interesting ideas and really interesting things. So, I looked at Korea, right? Why Korea? Because Korea is the world's most wired country in the world. I don't know how many people have been to South Korea. Anyone from South Korea? All right, well, a couple of people. So, South Korea is this really wacky place, right? It's got the world's fastest and cheapest and most widespread broadband of anywhere in the world, right? This is according to the OECD. South Korea is also the place that has, and this is what this picture is showing, the world's most developed e-sports league. These are young Koreans playing professional Starcraft, right? These are people who are paid tens of thousands of dollars, in some cases as high as hundreds of thousands of dollars, to do nothing but play Starcraft. There are two television channels in Korea devoted to showing Starcraft. I'm not joking. And you can go, this is in the e-sports stadium in Seoul. And, you know, and so this is what they've done now with their internet, right? This is one of the things that's come out of their history. So I would put Korea at kind of one end of the spectrum. The next country that I wrote about is Senegal, which I would put not on the opposite extreme end of the other spectrum, but I would say somewhere a little bit closer. I would argue that Senegal is one of the world's best least connected countries. What do I mean by that? There are lots of countries in the world that have terrible, terrible situations. Places like Somalia, places like the former Zaire, places especially in Sub-Saharan Africa where there's been a lot of political and economic turmoil over the years. Senegal is a Sub-Saharan African country that is different than some of these other ones. In that, they've had a peaceful transition of power over the last 50 years since they became independent from France. And they're economically stable as well. So they've had political economic stability, that's good. They happen to be well placed to connecting to the undersea data cables that flow down the Atlantic Ocean, down across the western coast of Africa. And yet, so they have all these things that you would think would make the internet work well, would make more people get on the internet and use the internet, and make websites like this, which is called Face Dakar, which is the kind of gawker, if you will, of Senegal. It's a relatively new website. It's kind of a gossip news site, I guess. But it's only used by a really small percentage of the population. And so, you know, my question is, if Senegal is one of the best cases, one of the places in Sub-Saharan Africa where you would think the internet would work, why doesn't it work there? And that's, so Senegal is a little bit on the other side. The other countries are Estonia, which again I would put somewhere slightly less than South Korea, but you know, somewhere toward the middle top region. I obviously didn't write about every country in the world, so I don't know precisely what the rankings are, but you get the idea. Skype came from Estonia, right? And Estonia is this kind of place that I had, anyone, any Estonians in the room? One Estonian, I love you. Anyone been to Estonia? Good, a few people. So, you, those of you who have been to Estonia, you'll know, to me, Estonia is like a geek's paradise, right? There's free Wi-Fi everywhere. They have these really awesome digital ID cards. You can vote on the internet. You can access all kinds of government services on the internet. And of course, Skype, you know, came out of Estonia. And why did Skype come out of Estonia? Right? Why didn't Skype come from Silicon Valley or from Germany or from Australia or from anywhere else, right? Why did Estonia produce all of these kind of cool things? So that's what I'm trying to understand. And then again, somewhere in terms of connectivity, maybe further down, a little less than Estonia, maybe not quite as low as Senegal, is Iran. And Iran unfortunately has the distinction of being the world's first country to arrest a blogger. And they arrested this guy, Mr. Sina Motalibi, who was a journalist and blogger, and he was arrested in 2003. He now lives in London. And as we saw a couple years ago, with respect to people using the internet as a way to fight back against the government, right, there's been this kind of seesawing that's actually been going on a lot longer than 2009. It's been going on for over a decade now in Iran, where the government pushes one way against the internet, and people push back, and so on and so on. So this is a much longer, I think, more interesting story. So we'll take the first one, South Korea. In my book, I read about this guy. His name is Chun Kilnam, and he is a, this is just a little timeline of Korean history, and I think it's important to understand that. But yeah, so this guy's Chun Kilnam, he's now a professor in, he retired from his university in Korea, and now teaches in China and Japan. I didn't know a whole lot about Korean history before I started this. I don't know how many of you know a little bit about Korean history, but one of the things that I think is really important to understand about Korean history in the 20th century is this kind of weird relationship between Japan and Korea. And by weird, I mean, you know, not so good on the Japanese side. Japan annexed the entire Korean Peninsula in 1910, and so Koreans were basically forced to become Japanese. And Korean culture and language was very much suppressed for the beginning of the 20th century. Japan, of course, bombed Pearl Harbor and entered World War II in the 40s. 1943, the Pentagon is dedicated, right? So this is, again, in the kind of World War II period, and you know, Japan is kind of being defeated in the war and stuff. Chun Kilnam was born to a Korean family in Japan in 1943. And actually, he grew up speaking Japanese in Korea, excuse me, he grew up speaking Japanese in Japan even though his family was Korean, and he was ethnically Korean. Again, he was part of this, you know, this idea of kind of Japanizing people, even if they were from other places, especially from Korea. So the war ended in 1945, and eventually, you know, these kind of issues, unresolved issues from the Potsdam conference just down the river didn't resolve what was happening in Korea, right? And so the Soviets and the Allies were, you know, in disagreement over what should happen with Korea. So we've got this Korean War in North and South Korea, okay. So then we get into the 1960s, and there's this guy named General Park Chun-hee who takes power in Korea, he was a general, and he becomes this kind of dictator, but you know, he's an interesting guy because on the one hand, yes, he was a dictator, yes, he was authoritarian, yes, it was not a democratic system. However, he did create this amazing economic development program that continued for decades, kind of what he said in motion. And just kind of a key example of that, I think, which is kind of amazing, is that in 1961, there were 30,000 cars registered in South Korea. 35 years later, that number was up to 10 million. And for those of you who have been to South Korea, you'll know that it's, you know, it just is, I would say, just as developed and modern as anywhere else in the world. So, okay, so now we get to the 60s, right? And Chun-hee studies mathematics in Japan, and then he thinks about maybe going to do graduate work actually at Moscow State University to study mathematics. But during the 1960s, as Korea, there were kind of pro-democratic protests going on in Korea at this time, and he was kind of, he kind of felt this pull toward Korea. He felt kind of alienated in Japan, and even though he didn't speak Korean, and had never actually been to Korea until the 60s when he traveled there with his mother for the very first time, he didn't really know anything about Korea. And, but yet, somehow he felt like he didn't have a future in Japan, and he felt like he was kind of duty bound to help his ancestral home country. And so he thought about, okay, well, what could I do that would be helpful to this country that is undergoing this rapid, rapid development? And he thought, well, maybe I could be a doctor, but it turns out that, you know, hospitals kind of freak him out a little bit. He doesn't like the smells and blood and stuff. So then he thought, okay, mathematics, maybe information science and maybe computer science, because, you know, that would be useful to people as well. And so he looked around at various universities, and he decided to enter UCLA as a graduate student studying computer science in 1966. Now, for those of you who know your internet history, you'll recognize this, right? UCLA in the late 1960s was like the place to be for people working on this obscure thing called the ARPANET, right? And the ARPANET is what is now our internet, right? It started at UCLA in the 1960s as this American government-funded research project. That guy right there is a professor at UCLA, still teaches. His name is Leonard Kleinrock. And what he's standing next to is something called the IMP, which is the world's first router. So all those little, you know, 20-year-old routers that you guys have in your apartments or houses, originally they looked like that, and they cost, you know, tens of thousands of dollars. So, Chonthil Namar arrives at UCLA. He is classmates actually with Vince Surf, who invented TCPIP. TCPIP, of course, is what makes the internet function. So it was really kind of fortuitous that Chonthil Namar was around what was going on at UCLA at the time. And so what happens is Chonthil Namar, he studies, he gets his doctorate, he works and teaches for a little bit in California, but then he gets an offer to come back to Korea. Again, he'd never lived there. And he starts working on what he calls the system development network. This is the 1980s. And he's made a professor at this place called KAIST, which is the Korean Advanced Institute of Science and Technology. It used to be in Seoul, the capital. Now it's in Daejeon, which is a city about two hours south of Seoul. And so his idea was this, let's build the internet in Korea, right? And this is the 1980s. This is when the internet is still a relatively new thing. It's this kind of obscure computer science project. There's only a few internet nodes that exist, I think, probably by the 80s. I'm guessing that there was something like on the order of hundreds or thousands of nodes spread around North America, Europe, other parts of the world. And so he said, okay, well, we need to build our own network. And we need to build our own computers and our own stuff. And so he had this idea of making this network to connect. He was basically replicating the ARPANET. And this was kind of his own pet project. And so he, as a professor, he had graduate students. And these graduate students in the 1980s, they became this kind of dream team. And they went on to, and because of his experience in Japan and in the US, and knowing what he wanted to do, he wanted to create something new in Korea that had never been there before, which was to say the internet and technology, he told them, I don't want you to be professors. I don't want you to be academics. I don't want you to do what I did. I want you to be entrepreneurs. I want you to be leaders of industry. I want you to develop this country through the means of technology. And so what he would do is, it was almost like a start-up, right? These students of his, they would wake up at 9, 10 in the morning, they would code, they would hack, they would try to, you know, they were building routers, they were trying to make this stuff work. And then, and they would work till, you know, midnight, 1, 2 in the morning, whatever. But then on the weekend, he would, and this is my favorite part, he would make them go rock climbing. He would make them go hiking. He would make them go skiing. He would, you know, it was very kind of regimented, and he would tell them, he would kind of instill into them this idea of pride and of duty to the country. These were young computer scientists in their early mid-20s. They were exempted from military service. They were given full scholarships. They were just, you know, all the doors were opened for them. And he was saying, look, you guys have to take this seriously, and I will work you, you know, doing stuff during the week, and then you will have to work physically too, because, you know, I want you to be able to not only solve these problems, but to, you know, be healthy so you can work on this project. But so what happened was, so they did build it, they built this network. It did connect to the Internet. I believe it was the first non-U.S. project to, that was kind of independently developed to connect to the Internet. And so, and he got what he wanted, which was that these students of his, they came out of this program doing exactly that. Jin Ho-hoor is a Korean entrepreneur now, and he launched the first private Korean Internet service provider in 1998. The first broadband service was launched in Korea, and the person who was kind of in charge of that part of the company was also one of Chon-Kilnam's students. And through that, because it was so disruptive in the Korean market at that time, there were other companies that came on, and there was major, major price wars, and that was really what developed, what kicked off this kind of high, excuse me, very pervasive broadband across Korea. Also, in 1998, a guy by the name of Jake Song, he wrote a program called Lineage. This was a really, really big MMORPG, massive multiplayer online role-playing game, well before World of Warcraft and all the rest, again, developed by one of his students. And Lineage actually really pushed into the Korean Esports Players Association, that slide that I showed earlier with the guys, that guy in that pod playing StarCraft, right? This is this group that does this, Caspa. And so they, you know, it really kind of snowballed into that direction. And so, you know, I think that this is, again, this is a, if you want to kind of, a lot more details, there's more stuff in my book. But, you know, I would say that this combination of high levels of education, of nationalism, of duty, of pride, of these kinds of things really kind of pushed Korea into this direction. And they viewed the Internet as a means to getting to development. Obviously, they did a lot of other stuff too. And by 2007, they had hit 90% broadband penetration. I don't think that my home country of the United States has that high of broadband penetration. So let's move on to Senegal. And, okay, so in Senegal, I write about this guy, Amadou Tup. He is now also an entrepreneur and developer and kind of activist guy in Senegal. While I was researching Senegal, and I actually lived in Senegal as a student for about half a year in 2002, 2003, 1946, IBM actually shows up in French colonial Senegal. And they were hired to build kind of the IT systems or the kind of proto IT systems of the Senegalese National Railway and a few other kind of big government projects. And they thought that they could make money just like they had in other French colonies, like in French Indochina, Vietnam, Cambodia, those kinds of areas, Morocco, other places like that. And this was kind of the, I guess, early kind of IT environment that Amadou Tup was born in. He grew up as a kid under colonial Senegal, of course, occupied by France. And then Senegal became independent in 1960. By the later, by the end of the 60s, he won a logic and mathematics competition that was held by IBM. He later went on to work at IBM. And they, you know, he kind of rose through the ranks of IBM. He lived in France for a little while and, you know, really benefited from being exposed to various types of technology and development and things like that. By 1985, he had left IBM and he started his own company in Senegal. And then he attended CES for the first time. And 1995 was, I probably, I would guess, maybe some of the more geeky, hackery people in the room probably were using the Internet earlier or the web at least, or a little earlier. But I know for myself, you know, that was around the time when I first got exposed to the Internet and to the web. And Amadou Tup was the same thing. He saw an early demo version of Netscape while he was at CES in Las Vegas. And he just thought, man, like, this is really cool. We've got pictures, we've got text, we've got all this stuff. That would be great for Senegal. But, you know, he was worried about it being expensive and stuff like that, which is definitely an issue in Sub-Saharan Africa. But, you know, the kind of seed was planted in his head. And he went on to really encourage the government and he kind of ingratiated himself to various government officials and really tried to push the government to use more websites and for people to use the Internet in a better way. One of the issues that also happens in Senegal, or not just in Senegal, but in Sub-Saharan Africa is this idea of demonopolization and privatization of the telecom. So Germany, I think, went through this in the 80s with Deutsche Telekom and it's private now. The US had the same thing with AT&T, France Telecom, other big telecoms around the world. In Senegal, the telecom company, the incumbent monopoly, is this company called Sonetel. And they privatized in 1995. However, France Telecom bought 42% of the company. And a lot of people, including Abadutup, were very upset about this because they felt that it kind of reeked of colonialism. And it wasn't very kind of democratic in the way that they did it, but whatever. By 1998, Abadutup advised the government to put on election rolls in the Senegalese presidential elections. So what that means is people weren't sure kind of who was eligible to vote and who had been officially registered. And this general had been put in charge of this project and the general CSE went to Abadutup and he said, you know, what can we do? How can we make people trust that they're actually registered to vote? And he said, well, just put them on the internet. And so he did and people did that. There was little problems. He had some personal information up there that people probably shouldn't have access to, their mother's first names, which can be used as a personal identifier in Senegal. But it was a neat idea. Even though at that time, 1998, very, very, very few people in Senegal had access to the internet. But it was starting to come. And the government was buying into this as well. And there were all kinds of projects. And this is kind of what I'm talking about, is that there were a number of projects both from within Senegal and kind of coming from other places that kind of started and then kind of fell apart. One of the first ones was this program by the Senegalese singer, Yusuf Endur. Any Yusuf Endur fans out there? Anyone? A couple? All right. So he's this famous Senegalese singer, very cool guy. He, you know, plays in Europe and Senegal, of course, and all kinds of stuff. He's like a UNESCO, UN, like cultural ambassador or something, very charismatic guy. And he had this idea of founding these Joko Clubs. And Joko is a wall-off word. It's a local language in Senegal and it means connection or link. And the idea was to build kind of cyber centers, cyber clubs, community centers, places where people could go, kids could go and use the internet and stuff. And HP Hewlett Packard was involved and they were putting up all kinds of money. He gave it, there was a big speech about it, I believe at Davos during this time and, you know, everybody was really excited. But it kind of fell apart because it relied on a big American company or a big company to keep bankrolling this project. And the project fell apart by 2002. By 2003, the American government got involved and they had something called the Digital Freedom Initiative. Anyone heard of the Digital Freedom Initiative? Anyone? No? All right. One person. Okay. So this was a project that was started by the American government under the Bush administration. The idea was to bring better internet access, better connectivity to various places around the world and to teach entrepreneurs and people, again, as a development project. And the first country they picked was Senegal. And so there were all kinds of committees. There were American and Senegalese advisors that were trying to figure out how to make the internet work better in Senegal. They established a cybercafe in the middle of one of the biggest markets in downtown Dakar. But again, the project was funded for three years. It kind of fell apart after two years. That cybercafe that they built is still there. At least it was when I was last in Senegal four years ago. And it feels like every other cybercafe. And this was also around the same time when lots and lots of private cybercafes were opening up all over Senegal. So it didn't, again, that one didn't really go anywhere. I mentioned earlier, I just wanted to show this is a cable map of Africa. And so for those of you who may not know where Senegal is, it's, if you can see on the map there, there's the westernmost point in the north where that little text on purple and orange, Senegal is just north of that because that's Capol Verde. So Senegal is kind of the westernmost point in Africa. And like I said, Senegal is geographically well placed. You can see these massive data cables running down the coast of Africa. And their landing stations are in Senegal. And actually the countries, the landlocked countries that are next to Senegal, like Mali and some of these other places, actually have to rely on data access from Senegal because of the cables. And I actually just saw a tweet this morning that Nigeria, I think it's Nigeria, since some of these newer cables that you can see there in the diagram, like the orange and the purple ones, Nigeria internet traffic is up like 400% since one of these new cables was turned on. And as you can see, East Africa is really deficient in terms of connectivity as well. Anyway. So Digital Freedom Initiative didn't really go anywhere. By December 2003, the president of Senegal, this guy, Abdul-Iwad, had his own idea, which was to create something called Digital Solidarity. Anyone heard of this? The Digital Solidarity Fund? No? Okay. So yeah, so this was this idea. He proposed it in the WSIS conference, the World Summit on the Information Society that was in Geneva. And he said that, you know, look, part of the reason why Senegalese people and other people in the developing world don't have access to the internet or don't have as much access as we would like is that stuff is too expensive, right? So what I want to do is I want to make, I want to create a program where people at the point of sale in, let's say, Berlin, you walk into a shop, you're like, hi, I want to buy a laptop, it's 1,000 euros. Would you like to donate 10 euros to this Digital Solidarity Fund that would then go to people in other countries? This didn't go anywhere at all. They created a foundation in France and another one in Switzerland and this didn't, also didn't go anywhere. In the meantime, Sonatelle is raking in the cash. I'm pretty sure Sonatelle is the most profitable country, or most profitable company in Senegal. In 2007, they had a profit of $310 million. Pretty good. And still, you know, Senegalese internet penetration remains kind of low and this is what I say when Senegal might be, there are probably some other ones that would fit this category as well, might be one of the best least connected countries and that's what I'm saying is that, and I think part of it has to do with education, part of it has to do with level of economic activity. Only 40% of Senegalese people can even read, so already 60% of people can't use the internet because they can't read. So yeah, so that's the story of Senegal, this is the In-Nut Show. Moving on to Estonia, one of my favorite places. I am really obsessed with Estonia. I could talk for hours about, just about Estonia. I had never been to Estonia, I'd barely heard of Estonia until about six years ago when I read an article in the Christian Science Monitor that said that Estonia had declared internet access as a human right and that just blew my mind and I started reading up on Estonia and I discovered that Skype had come from there and all this kind of stuff and that was pretty amazing. Again, a little bit of history. The Nazis, so Estonia, I didn't know as I was reading about it, Estonia, for those of you who may not know, Estonia is way up in the north of Europe, not that far from here, up by Helsinki in Russia and they were invaded over the last thousand years by basically all of their neighboring countries at various points. The Baltic Germans were very active in the 19th century in Estonia, Poland, Denmark, Sweden, all kinds of other countries came and went in Estonia. By the 1940s the Nazis were up in there hanging out for a couple of years. Then the Soviets came in, right? And the Soviets, they said, okay, Estonia, we don't want you to learn about liberal arts and social sciences and stuff. We want you to be technological, we want you to be scientific. So what did they do? They established in 1960 the Institute for Cybernetics and they established it right in Tallinn, Estonia and they were doing exactly what it sounds like, cybernetic research and stuff like that, which I think is pretty cool. In 1967, this guy, Velio Hammer, was born. For those of you who've been to Estonia, you'll know, as I said, there's free Wi-Fi all over the place, you can thank this guy for doing that. Velio Hammer has become this kind of Wi-Fi evangelist just kind of preaching how great free Wi-Fi is. And so as a result, there's free Wi-Fi in the airport, in the port, in the bus station, in farmhouses, in all kinds of places all over the country. Estonia became independent, of course, at the end of the Soviet period, 1991, and Estonia kind of woke up as best as I can tell and kind of rebooted itself, if you will. And so there were all these ideas coming around and one of them was this Tiger League project or Tigri-Hupa in Estonian. And the idea was, let's wire the entire country, let's put the internet access in every school in all of Estonia. Estonia is not that big of a country, 1.3 million people. As somebody said earlier, I think that's the size of, you know, a decent size German city. In American terms, that would be like San Francisco, Oakland, and Berkeley put together. Anyway, so they, you know, they went on this ambitious project and they connected all the schools and they spent a lot of money and they, you know, and there was this idea that, again, that we can kind of leap forward into the future. There were other ideas too, like the Digital Signatures Act and the Digital ID Card Act that created these digital ID cards. E-Parliament, the system where if you were, so the Estonian government, as best as I understand it, they have a cabinet of ministers and they propose bills on anything, you know, transport, defense, economics, whatever, and they discuss it and then once they agree, then that bill gets sent to the Estonian Parliament and then they vote on it and it becomes law. But so they said, well, it's stupid that we're printing out all these bills and you've got all these stacks of paper, so why don't we do this online, right? So if you go to Tallinn, you'll see there's this kind of online interface and they said, okay, we're going to put all the bills online and if the ministers don't discuss them online before the physical in-person meeting, then the bill passes, right? The idea was that if it's not worth discussing online, it's not worth discussing in-person, so let's just streamline this process. And so that's what they did. Wi-Fi EE was established. This is Velio's website and he catalogs all of the Wi-Fi hotspots all over the place. 2003, the first Skype prototype was born and it was actually created, the very first Skype offices, they now have their own offices, but I find it interesting that their very first offices were actually in the Institute of Cybernetics. This is what some of these Wi-Fi hotspots look like. That's actually in a public park, but that logo, that Wi-Fi EE logo, you see it, it's very common. You see it just like you would see on a restaurant, you know, Visa Mastercard, Eurocard, whatever bank card, you know, for at a bar or a restaurant or something, and then you'll see a little Wi-Fi sticker. And that's what the Estonian ID cards look like. Again, they're about the size of a European bank card and they've got little chip, and so what you do is you plug that into a USB card reader, you go onto a citizen's portal and you have access to all kinds of government services ranging from, you know, paying your parking tickets or your speeding tickets or checking your university admissions or paying your taxes or voting in national elections. And that's pretty cool. And then I wanted to throw the Skype thing up there because, you know, Skype is from Estonia too, and when you get to Tallinn Airport, this splash page of Skype comes up and says that, you know, Skype is sponsoring the Wi-Fi there. Anyway. So yeah, and then Estonia kind of progressed in this way as well, and I guess you could say the really, I think, kind of one of the moments that Skype kind of arrived onto the world stage or kind of, you know, yeah, this kind of landmark moment was when President Bush received as a gift a Skype phone from Estonian Prime Minister Anders Ansip when President Bush was visiting Estonia in 2006. By 2007, Estonia had started this program of online voting. Again, using these digital ID cards, there's digital signatures and encryptions and all this kind of stuff. People, I'm sure anyone who's read anything about Estonia, oftentimes, at least in the American press, they call it Estonia now. In 2007, you might have heard there was a little bit of a cyber skirmish, cyber attack, cyber war. It's very scary. There was a statue of a Soviet soldier in Tallinn that was in a park, and the Estonian government had decided to move it to a different park outside of town. A lot of Russians still living in Estonia got very upset. As a result, a lot of Estonian websites got attacked as a form of political protest. There were Russian language websites, not like kind of traditional underground hacking kind of websites, but I think we saw kind of a similar thing with Anonymous where people kind of made it very easy. It was just like, okay, follow these steps, and you too can join the cyber attacks against Estonia because they moved our statue. So government websites were hit. These were DDoS attacks. These were kind of hacktivist, like defacing, you know, putting up false statements on the prime minister's website and stuff. It wasn't very kind of threatening. I don't think. The Estonians investigated. They tried to figure out who did this. Of course, everybody in Estonia pretty much believes that the Russian governments either implicitly or explicitly was behind it. Only one guy was ever actually not even convicted. He pled guilty. This guy, Dmitry Galdyshevich, he is an ethnic Russian but Estonian citizen living in Estonia. He admitted guilt as to participating in these attacks and he was fined $1,700 and didn't serve any jail time. And the Estonians basically felt frustrated because their Russian counterparts would not give them access to any kind of data or records and stuff. As a result of these cyber attacks, the cooperative cyber defense center of excellence, logos up there in the top, was established in Tallinn in 2008. This is part of NATO. This is a research center that is devoted to cyber defense and cyber security that they created in the wake of these attacks. And in fact, Estonia had actually proposed this idea way back in 2003. But, you know, NATO was like, oh, cyber attacks, it will never happen. And then it did and then they got their center. And one of the other cool things is that in 2011, this year, you can now use your mobile phone to authenticate yourself for online voting. So you can register and you get a special SIM card with some special encryption on it and put it in your phone. And so instead of having to put your ID card into your computer or into a card reader to authenticate your identity when you want to vote, you can now do it by cell phone. You can't vote over your phone, but you can authenticate. Anyway, last country, Iran. I wrote about this guy, Omid Mehmatian. He's an Iranian journalist and blogger. He now lives in San Francisco. He has become part of a group of people, including my own father, who are basically permanent exiles from Iran. Germany has a large Iranian community as well. And Iran actually has a really interesting history when it comes to the internet. I think Iran has one of the highest internet penetration rates in all of the Middle East. It's something like 33, 35 percent give or take. And Iran has been on the internet for a pretty long time, actually. Way back in 1993, Iran was able to connect to the internet through Austria, through an academic network called CSNet. And it kind of slowly grew, again, similar story to some of these other places that I mentioned. By 1995, there was 30,000 people online. By 2000, there was a million Iranians online. By 2008, that number jumped to, I think, like 20, I think, tens of millions, 20 million, something like that. Big number. Again, you know, it's important to understand the history and the politics, I think, because as I said, this is about kind of what kind of emerges out of these countries. By 1997, a guy by the name of Mohammed Khatami was elected president. He was the president before the current president, Ahmadinejad. Ahmadinejad was elected in 2005. Khatami was president from 1987 to 2005. He was viewed as a moderate, as somewhat of a reformer, as he had spent some time in Europe, actually, in Germany. And he really pushed for some reforms within the Islamic system. He opened up media. He allowed newspapers to open. He allowed civil society to kind of open up. He allowed for nonprofits, non-governmental organizations to open up. There was a moment, there was a few years where there was kind of a moment of opening up a little bit of Iranian society. Of course, you know, there were certain, what they call red lines, that you couldn't cross, right? You couldn't say anything bad about the Islamic Republic. You couldn't say anything bad about the Supreme Leader. I told the whole, hominy, and so forth. And by 2000, as, you know, more and more Iranians are getting online, we have the first instance of the government pushing back against what's happening on the Iranian internet. There was this guy called Ayatollah Monteseri. He was a reformer, reformist Ayatollah against the government. He had formally been really kind of part of Iranian government, he had been closely associated with Aitolahomini, the supreme leader, the leader of the Islamic revolution. But during the 1980s, he kind of fell out of favor. He disagreed with some of the brutal policies that the government imposed during the Iranian Iraq War, during the 1980s. So he was basically under house arrest for the rest of his life, from the 1980s until when he passed away just a couple of years ago. In 2000, he posted a memoir on his website, Monteseri with an i.com, and he posted this memoir and he described what he had done and what he had seen in his relationships with the government and said all kinds of bad things that the government didn't want to get out. And so what did they do? They started their own website. They started Monteseri with a y.com. So they cyber-squatted him, kind of. And they were trying to fool people into going to the wrong website and it didn't really work. But I think that that's kind of interesting, that they cared enough to create a fake webpage to fool people from reading this guy's stuff. By fall 2001, as blogs were starting to come about in the US and in Europe, the first Iranian blogs were coming out too. And I don't know if this is still true, but there was a period when Persian was like the number three or number four language amongst blogs in the world, which is kind of surprising given that it's a relatively small language with respect to the whole world. And there was this guy called Hossein Dirakshan, also known as Hodor, who published a guide in Persian, teaching Persians how to blog in their own language. Hodor.com started supporting Unicode as a way to make it easier for people to get online. Various people were arrested and Sina Muatalebi, the first guy to be arrested, was arrested as he had published some articles that were saying some bad things about the government as well. He was a journalist and he was talking about how that there were things that the government wasn't doing enough to fight, for example, unemployment, which is a big issue, and other things like that, and he was arrested. And there was a whole series of people, including Omeed, who I profile in my book, the guy who was pictured who were arrested at the end of 2004. So for all of you bloggers and Twitterers in the room, which I think is probably most of you, you are in company with President Ahmadinejad and Supreme Leader Aitol Hamani. They're both blogging and Twittering. Aitol Hamani has a Twitter account here. You can go follow him. He tweets in Persian and English. I don't know how good your Persian is, but you can read his stuff there. So yeah, this was a sign that came up during some of the protests from 2009, which I really like, which is, you know, God is with us. Are you filtering him too? Of course, the internet in Iran is filtered and censored and blocked and stuff like that. And I'll just move quickly through this so I can finish up and get time for questions. As you know, and I talked a little bit about this earlier, there was this movement to, you know, there were a whole bunch of series of protests. Twitter and Facebook where people were pushing out videos and things like that. The government was also pushing back. I was having conversations with some people earlier about there was this website, geardob.ir, which used these photos. And I don't know if you can see, there's little red circles around people's faces. And on that webpage, the government is basically asking people to identify protesters. Yeah. Recently, they had this blogging competition that was only open to pro-regime blogs, so that was interesting. And I guess, you know, people have been asking me, like, oh, do you think Iran is different than Egypt and Tunisia and what's going on? And I guess for me, like, my kind of gut feeling is that it is really different. You know, one of the main reasons that I don't like the term Twitter revolution is because revolution implies that things have dramatically changed, but nothing has dramatically changed politically speaking in Iran. The government is still there. You know, things are going on. Yeah, there's, you know, a little bit of protests and stuff. But I think one of the major differences, you know, is that the Iranian government has shown that it's been willing to use, you know, force, right? It sends out armies of guys on motorcycles with clubs and beats people up, right? And what's different about that in Egypt is that the Egyptian government, you know, even with all of the people coming to Tahrir Square and all this kind of stuff, you know, the Egyptian army didn't fire on people. And I think that's a really big difference, you know, same with Tunisia, right? There wasn't that same kind of use of physical violence against people. So I think that that's something that, again, we often lose sight of. Anyway, I'm done. Thank you. Thank you. Thank you. Thank you.
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In his new book, “The Internet of Elsewhere,” Cyrus Farivar looks at the role of the Internet as a catalyst in transforming communications, politics, and economics. In it, Farivar explores the Internet’s history and effects in four distinct and, to some, surprising societies — Iran, Estonia, South Korea, and Senegal. He profiles Web pioneers in these countries and, at the same time, surveys the environments in which they each work. After all, contends Farivar, despite California’s great success in creating the Internet and spawning companies like Apple and Google, in some areas the United States is still years behind other nations. Don’t forget: – Skype was invented in Estonia–the same country that developed a digital ID system and e-voting; - Iran was the first country in the world to arrest a blogger, in 2003; - South Korea is the most wired country on the planet, with faster and less expensive broadband than anywhere in the United States; - Senegal may be one of sub-Saharan Africa’s best chances for greater Internet access, and yet, continues to lag behind.
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10.5446/21579 (DOI)
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Hello everyone, thank you for being here. I'm Jeremy Zimaman, I'm the co-founder and spokesperson of the Citizen Organization, La Quadrature du Net. La Quadrature du Net is a kind of citizen toolbox. We're basically a bunch of activists with quite some experience with a legislative process and we are providing tools for citizens, for everyone, to understand what is going on when fundamental freedoms are threatened on the internet and tools for everybody to participate in the public debate, in the democratic debate, to make one's voice heard in those issues. We've been very much active in France and in Europe on the EU level, on the European Parliament, in the last months and years and you may have heard of the nefarious Adopi law in France or the telecoms package on the EU level or ACTA, you'll hear more about ACTA later on. And what I want to discuss with you today is this very disturbing trend of copyright law to be used more and more as a tool to hurt our fundamental freedoms, to hurt our freedom of expression, to hurt our privacy, to hurt our right to a fair trial and to discuss together on how we might find ways to counter this, how we might build tools together to collectively address those issues. So we're in the mindset of the entertainment industry where the whole world is covered by a bunch of pirates and we have to imagine for a moment, we have to imagine that a myth that is widely spread is for real. It's like the Santa Claus exists. No, we have to believe that pirates exist, that pirates are those evil people who don't like culture, who don't like artists, who kill the artists, who kill the industry and we have to believe for one moment that file sharing is literally killing music, killing the arts and killing movies. So when those industries realize what was going on with the internet and with Napster in 1999, you remember the story, they tried first of all to sue individuals, to go to courts, to hire very expensive lawyers and to try to get examples of court decisions where people would be convicted, where people would be found guilty of piracy, harming, hurting, killing and so on and they thought that this would lead to people who just stopping doing it. Well, you all know the rest of the story. So far it's an epic fail, as we say on the internet and so the individual suing of people was a failure. So this was the version zero point something, let's call it zero point one or zero point two of the war against sharing that those industries are waging right now. Then along the years they came with new ideas of schemes. Then there was the election of Nicolas Sarkozy in France. When Sarkozy was elected, John Kennedy with the head of IFPI, that is the main worldwide lobby for recording industry said, oh with this guy we have a champion that will promote our ideas. So when Sarkozy got elected, they had a way to experiment with their new scheme. You all heard of the Adopi law, the three strikes law. Who among you didn't hear about the Adopi law? There's quite a few. Well, you don't miss anything. All you have to know is that you don't want one at home. Well, in that scheme the entertainment industry thought it could subvert the resources of a state in order to make justice more efficient in their view, more fast, faster and get more decisions. Therefore people would be more disuated of sharing. So in the scheme of Adopi you have some kind of administrative authority. So it's not a court, it's not a judicial authority, it's an administrative body that gets complaints from the entertainment industry itself. So that's private actors from the entertainment industry that sends complaints to that administrative body. That administrative body sends an email saying, oh what you're doing is wrong, you should stop and so on. And then if it continues, it sends a mail, a physical paper mail made of dead wood. And then if it continues in the first version of the law, the administrative authority sent an order to the internet service provider of that person in order to cut off that person from the internet. Literally cut the wire, disconnect that person from the internet. And so this is why you see this mortuary bunch of flowers here. It's because this is an epic fail also by itself. The constitutional court of France, the Conseil constitutionale, gave a decision. It was a real long-term political battle for years that we led against the government to make everyone understand clearly that the cutoff of internet access is in no way a sanction that could be taken in a democracy. We also made them understand quite a few points about having administrative authority giving sanctions, about having private corporate actors collecting evidence and so on and so on. And then when the law was voted, the constitutional court issued that decision. I encourage all of you to take a look at the paragraph 12 of the decision that you can find by its reference 2009 minus 580. In that decision, the highest jurisdiction of a small country named France said, given the importance of internet for the democratic participation and the expression of ideas and opinions, freedom of expression implies freedom to access to the internet. So this is what we won in the political battle of the Adopi. This is very important for us and for the future of our actions indeed. And therefore, saying that, the constitutional court said, so access to the internet is mandatory for freedom of expression. Therefore, you cannot have an administrative authority that would restrict freedom of expression. It has to be the judge. Therefore, it overturned the law and removed the sanctioning power from that Adopi administrative authority. So you all heard of Nicolas Sarkozy and his personality of not being able to listen to anyone and just doing his stuff. So the government came back with a new law, the Adopi II, the return of the vengeance of the administrative authority, when the whole process is the same. But in the end, instead of ordering the sanction, the Adopi sends the dossier to a higher level to the judge, to the judicial judge. So it is supposed to be compliant with the constitutional decision. Well, this is why we think Adopi is dead wood at the moment. It's because they're trying, barely trying to make it work. So for one year, they've been sending emails. The budget of Adopi is 12 million euros a year out of French taxpayers' money. So they mostly hire a communication service that make press releases and sends flyers to schools and things like that to say sharing is bad. Kids, don't do this at home. And so it's, we make that bet. We are convinced that the day the Adopi would eventually try to send the dossier to the judge, the judge will look at the thing, put it in the trash can, and say, now you come back with evidence that those IP addresses, strings of zero and ones collected by private actors are in no democracy, any kind of evidence. So this is our bet. The bet of Adopi is that by influencing people, by making them afraid, by sending all those emails saying, oh, you will risk so much, you will be cut off, whatever, whatever, people will just be scared of it. So as long as people are not scared of Adopi, Adopi doesn't work. And this is why we say that this is an epic fail. Well, this is an ongoing epic fail on a political point of view for the French government at the moment. So this was version, let's say 1.0 of their policy against sharing. And this is fail. In no other country than France, such a policy will be put in place. It costs a lot. It costs a lot to the taxpayers, but it also costs a lot politically. Everybody watched this carefully so that the French government took blows and blows and blows. And we talk with members of the parliament that say to us that even today, right-wing members of the parliament, that say to us that when they go to the marketplaces on the Sunday morning, just you know, to shake hands and show how beautiful their smile is and how nice it would be to have them reelected someday, when they shake hands, they have young people coming at them and saying, why do you vote Adopi? Why do you vote Adopi? It was really, really a strong political, social debate in French society. And when you took privately with the members of the right-wing majority, they use Adopi as an example of a bad law that is being force fed to them and that they are forced to vote. So you're in the shoes of the entertainment industries and you try to sue individuals. It didn't work. You try to change the policy of the whole state to subvert the means of the state to make all these go faster, more efficiently and so on, but it failed. Then what you do as a next step is the version 2.0 of this scheme. How many among you have heard of Acta? Wow, that's quite a lot already. So maybe you know already, all I'm saying already. Acta is a wonderful, well wonderful on a cynical perspective, but it's a very obvious example of how those industries are powerful and how they're able to subvert democracy, to bypass democracy, to circumvent public opinion in order to have what they want. So Acta is, well it's a very complex issue. It's a very complex dossier, but this is something we can really hold up in the air as a smoking gun, as an evidence of what those industries are doing to our societies and to our democracies and to our legal system. So Acta for the few of you who didn't hear about it so far is the anti-contrafitting trade agreement. So it is supposed to be a trade agreement, hence the name. Trade agreements are those agreements that states strike together, like for instance when the US go to some African country and say okay we continue to buy your cocoa or coffee or whatever, but you will sign these agreements about selling your oil and whatever expensive thing we need to build mobile phones or something to us. So usually trade agreements involve trade, the trading of goods, but in the case of Acta it is mostly about copyright patent and trademark issues. Initially Acta is about border measures, so what custom officers can do on the border to when goods enter the country or leave the country, try to block containers of stuff or whatever. But right from the beginning we heard that Acta would also involve legislation regarding the internet. So for sometimes we were in some kind of haze, some kind of fog, we didn't have access to anything that was into the Acta agreement because it was negotiated in secret. Since the end of 2006 it was negotiated by 39 countries including the 27 member states of the EU represented by the European Commission. And so we couldn't know what was happening into it until WikiLeaks leaked some version of the text, some draft version of the text, something like early 2008, during the year of 2008. So we saw in those leaks what Acta was trying to do with the internet and this got confirmed over time. It was very difficult to go and talk to the politicians about it. When we talked with the negotiators of Acta they were talking to us in a very rude or condescending manner saying yeah but those leaks you're talking about we don't even know if they're real or not and we won't authenticate them anyway so yeah get the fuck out of it. What was the basic message? So we had to go and convince members of the European Parliament so they put pressure on the European Commission so ultimately some draft version of the agreement were officially published. And then we could know what we were talking about. So I'm talking end of 2009, early 2010. And so the scheme of those industries when the enforcement on the level of individual fails, you remember you go to the state level to try to optimize it to make it more efficient but it fails as well. Therefore the objective is to push enforcement closer to the core of the network. Enforcement as close as possible of the network itself, of the core of the network itself. So I'm going to show you some boring stuff for a moment to explain to you what Acta is about. You see here an article that is article 23 so this is the final text of the agreement because an agreement was reached by the end of 2010. Acta brings for the 39 countries we negotiated it new criminal offenses, new criminal procedures and penalties to be applied at least in cases of willful trademark underfeating or copyright or related rights piracy on a commercial scale and ensure that criminal liability for aiding and abetting is available under its law. So it sounds like bullshit legalese and it is mostly. But what this means, well first of all copyrights piracy on a commercial scale so far didn't mean anything in law, in any kind of legislation but you understand that this very notion of a commercial scale means about anything. If one million people share one file then one can argue that well this is commercial scale. If one makes a website that allows users to do something and then earns money through advertisements well this is commercial scale. If you create a new service or whatever that allows people to remix videos and then thousands of people use it then it's a commercial scale as well. So this is a very very broad scope for something that is criminal sanction. So this is something where prison is usually involved and you can see that it has to apply criminal liability for aiding and abetting. So aiding and abetting once again is something extremely broad when you're an internet service provider for instance one could argue that you are abetting the use of BitTorrent to your users. When you're YouTube and you allow your users to put whatever video they want to put on it you can argue that you are aiding copyright infringement on the commercial scale. So this is really the 2.0 version of the Warren sharing. You make such a weight, you make such a burden of a risk of very high penalty to weight on the intermediates of the internet which is the internet service providers, the internet access providers. You make them liable for whatever the users may be doing. So this is what is really the key to that debate at the moment. Usually the internet companies cannot be made liable for what the users are doing but with this new trend in copyright enforcement you literally make them liable for whatever the users are doing so you literally turn them into some kind of private copyright police for more boring legalese. You see here that each party shall ensure blah blah blah expeditious remedies to prevent infringement and remedies which constitute a deterrent to further infringement. So I don't know if among you are people with technical background but people with a technical background could try to imagine what would be in technical term a deterrent to further infringement. Further infringement by definition are infringement that didn't happen yet, that may happen. So what is clearly aimed for in this kind of text is the filtering of content, the automating of filtering of content, the automating of removal of content or blocking or access or very extreme measures like this. So with this agreement with this text the objective I told you is to turn internet companies into private copyright cops in order to make them use whatever method is available including filtering of content, including the removal, automatic removal of content and so on and so on. So one meme, one bit of text that we see all around in those policies those days that is part of that 2.0 scheme to make the war against sharing and the war against the public is this notion of promoting cooperative efforts within the business community to effectively address trademark and copyright or related rights infringement. So you understand that this notion of cooperative efforts that are also called voluntary agreements or in the UK a memorandum of understanding is a way of making these companies to comply with the objective of setting up those policies. So it's literally like putting a gun on the head of somebody and say yeah please do voluntarily sign this paper. This is the kind of cooperation. So this is a very disturbing trend first of all because all of this wasn't debated in a democratic way that was I think the objective because when you look at the debate that was in France for instance with the Adopilo you understand that those issues of what shall be done or not with the internet are extremely fundamental, are linked to the fundamental freedoms of individuals or something that is very well very important. Therefore you try to avoid a debate on it and this is how the whole act was done, the whole act was crafted. So the question is what this would mean for the internet? What this would mean for our everyday lives? You've seen maybe this image before several times in the last month the US Department of Justice issued orders directly to the ICANN, the ICANN that manages.com.org.net domains to make them remove some domains from the internet in the name of copyright. There were torrent sites or whatever watch replica selling sites whatever things that were infringing on copyright or trademark or whatever. So this is a very clear example when for some reason for copyright trademark reason you pressure an intermediary of the internet in order to force them to remove a whole bit, a whole part of the internet. This is literally parts of the internet being shut down without anybody being able to do anything about it. So this is the kind of actions that those industries want the intermediates to take. This is one example among many and this is what must make you think of what would be the internet if copyright, trademark and patents were a pretext that could use such actions. Well actually you have a very good example here at Repubblica because there is no internet. So you can all see what it is and how difficult it is to be without internet and without bits of the internet. But this is a very serious matter and we have to ask ourselves what to do about it. So there is one part of an answer that lies in the European Union institutions. The ACTA agreement has a final step before it can enter into force in the EU which is a vote by the European Parliament. The whole European Parliament will have to say yes or no to ACTA and this will be a historical occasion for all of us to participate into rejecting it, into having it rejected. So we don't know yet when this vote will happen, possibly before the summer break, most probably after. This is a new procedure since the Lisbon Treaty where the whole Parliament will have to vote yes or no. There will be no other possibility for amendments or anything, yes or no. So stay tuned, subscribe to the RSS feed or Twitter feed of La Quadra Turgenette or whatever or stay tuned to Net's political sources of information about those issues. And this is one occasion we will have to defeat such policies. But on the issue of ACTA, the EU might be the key, might be useful for us to win, but also there are very disturbing process going on within the European Commission. The market general directorate of the European Commission held by the French Commissioner Michel Barnier, once again I'm sorry, it's always France. Anyway, the market, the G of the Commission is right now working at the revision of the copyright framework of the EU, namely the IPRED directive, it's called IPRED for Intellectual Property Rights Enforcement Directive. It's a 2004 directive that broadens the scope of what should be considered as copyright enforcement. And when the Commission initiates the revision of such a directive, it doesn't ask itself, maybe we did it wrong, maybe we should go backwards, maybe there is another way than blind enforcement in the digital environment, no, no, no. It asks, how could we go further, how could we target more the internet, how can we be more enforcement, how can we enforce more. And so there is a process already going on when the Commission launched its consultation, the questions asked to the general public were literally, do you think we need more tools like what is in ACTA? Do you think we need more criminal sanctions? Do you think we should ask more to the internet companies to do the police themselves on the network? So it is a constant process. The influence power of those industries is extremely strong and goes to the highest level of the EU institution. So it is very nice to think of the European Parliament as a democratic institution, it is one, it is the only democratic institution in the European Union. But we have to keep in mind that the co-legislator with the European Parliament is the council of the EU representing the member states that is completely opaque and completely inaccessible to us. And we must also keep in mind that the Commission is this administrative body that takes the initiative of the laws and that through its market, at the moment, is literally taking steps like the ACTA to change the internet into some kind of copyright police. So this is one part only of the answer which is acting towards the EU institutions trying to make things change in the text, within the legislation. And another thing we have to keep in mind is that as I told you earlier, all that relies on a myth, the myth of the pirates, the myth that file sharing is hurting the economy, the myth that file sharing harms sales. And you can see it as even in the ACTA itself, this is another boring part of the ACTA. This is the damage section. The ACTA goes as far as saying that the judges will have to consider any legitimate of measure of value the right holders submit, which may include lost profits, the value of the infringed goods or services measured by the market price or the suggested retail price. They have to make those 39 countries agree together that when the industry will come to a judge and say, oh, look, that kid downloaded 1,000 movies, the price of a DVD is 20 euros, therefore 1,000 multiplied by 20 is 20,000 euros, that kid cost the industry 20,000 euros. This is exactly what it says. So if they are forced today, if they feel obliged to write this in the legislation, if they feel forced to make this become the truth that way, then it shows a weak spot. And I think it shows exactly where we have to strike them, where we have to retaliate. Because we all know that this is wrong, that this is not true. We all have experience, either direct experience with file sharing or people among us who downloaded the 1,000 movies and we all know they wouldn't have bought 1,000 DVDs. Or maybe we have experience by ourselves or by others that people who do file sharing are actually not that bad clients for those industries. I show you here one figure from, oh, I didn't source that image, which is very, very wrong. Okay. So you'll have to send me an email and I'll give you the source of this study and, well, I'll give you the source of this study and other studies. That shows that literally since the year of Napster, you can see the dotted line here, represent Napster. So you can literally see that since Napster, the number of concert performance literally boomed in the US. It is exactly the same in Europe at the moment. You can also see that the album sales went up and down. Exactly like the vinyl sales went up and down, like the cassette sales went up and down and so on and so on. Every new product goes up and at some points peaks and then goes down. And so as you can see here, as you will see in many other studies I source this time afterwards, everybody who is not linked to those industries and make a study and make independent study on the issue shows that the economy is not hurt that badly. That maybe the city sales are going down, but there are some other parts of economy that are going up. This is the concert sales. This is the ticket sales for the cinema. This is the sale of iPods or other MP3 players. This is the sale of video games. And so if you just look at the data, you see that what the industry is saying is just plain and wrong. This is part of a study that was literally commissioned by the Adobe itself. You can see its logo on top. So this is the administrative body I told you about earlier from the French government that is supposed to track down the evil file sharers that are so much hurting sales. And what it shows is how much people spend for cultural goods. In red are the people who have a so-called illegal use of the internet. And in blue, the people who have a legal use. And you can see that the first ones are people who do not spend at all for culture. People who do file sharing are so few compared to people who do not do file sharing. People who spend from 9 to 19 euros, you can see that the people who do file sharing are spending more. 20 to 30, 21 to 99. And you can see that the people spending more than 100 euros a month are 9% among the people doing file sharing as opposed to 5% among the people who do not. So, and this is confirmed by a study from the government of Canada, by a study from the government of Netherlands, by a study from the Ipsos Institute in Germany and so on and so on. And you can find all those studies, it's a non-exhaustive compilation that you can find at this URL that shows literally that people who do the more file sharing are the people who spend the more money. Those are studies that shows also that file sharing might have a very small impact on the drop of sales of physical goods. If not a neutral impact. And some studies even conclude to positive impact. The most detailed ones show that there would be a small impact on the artist that sales the more, a neutral impact on most artists and a positive impact on the artist that sells the less. So that file sharing would be some kind of progressive tax that will take more money from people who already sell a lot and that would give back money to people who don't sell much. So, I don't ask you to believe that 100% to be convinced by that. But even if you don't believe it, just consider that there is a margin for doubt. That what the industry is saying may not be completely true. That when they say that file sharing is just killing the world, and the artist, and everything, and there's blood on the walls, it may not be true. So, I think this is one very important spot, a very important weak spot where we can hit them. We can take those figures, we can make them more explicit, more public, we can educate, so to say, our elected representatives, journalists, the general public, and we can work collectively to counter this meme from the industry that file sharing is a bad thing. Actually, all those figures, all those studies demonstrate that sharing helps culture. And it's something that we know that we feel inside. When you like a record, when you like a book, what do you do with it? Do you lock it down, or do you try to lend it to as many people you like? When you like reading, do you go to libraries where people share books? Or do you just stay in your room with your own books? It is evident in every major step of history we have witnessed that, that the more culture is spread, the more it is alive. Think of all the so-called modern arts movements in the 20th century, since of the surrealists, since of fluxes. Everybody who innovated, who created new things out of culture, got inspiration from previous works, got inspiration from the peers. Nobody can create out of nothing. This is, this is a myth. This is something that is simply untrue. So this is, once again, I think some very simple idea, a very simple political message that we can spread, that we can build all together to counter that influence from the entertainment industry. It's all about sharing. They call it stealing, looting, pirating, thieving, killing, whatever. It is all about sharing, and there is no culture without sharing. So the situation is that today we have a relatively open and free, therefore neutral internet between our hands. We still have that freedom of expression that is allowed by this internet. We can, you see the example of the Arab Spring. We can build movements, we can organize movements, we can organize events that can have an impact on whole political regimes that can literally change societies. And we have industries that literally want to destroy that, that want to destroy that capability of everyone to use the internet to share and to participate in culture and to participate in society. So ask yourself what you should do with the internet, what you should do with your blog, with your Twitter feed, with all those digital tools you have between your hands. We have to make it clear for everyone that the internet, that digital culture, that digital technologies are made for sharing, that those zeros and those ones cannot be stopped, cannot be blocked unless you destroy all that we built and turn our societies into police states or whatever things nobody would consciously choose to live in. So I think we are at a major turn in our societies. We have never been so much connected and at the same time there has never been such violent attacks on our freedom, such as ACTA, such as the reaction of the US government on WikiLeaks, for instance, such as what may be prepared for the upcoming G8 that will be hosted by France, I'm sorry once again, where Nicolas Sarkozy said several times that he wants to make it the G8 of a civilized internet, which is basically a term that was invented in China to describe the Chinese internet. So what those industries allied with those politicians are building at the moment has the potential to literally alter the shape of the internet and literally block us from doing what we want to do and what we want to do is sharing. So once again we have to explain it, we have to make it clear and we have to stand for that right that we have of sharing the things we love and yeah that's it. Thank you and I'm sure there are some questions and interventions I saw a finger lifting from there. Is there a microphone? Yeah, just one second. Just an idea for the G8 summit but I think you also thought about it. If there is this topic on the G8 agenda, is it possible to do a campaign to sensibilize the European parliament members for that but I think you are planning some kind of that. I don't know, is it on an island or is it, will it be viewable that G8 summit? It's a kind of island, it's in Deauville in France, so it's some kind of island. I personally don't believe that physical actions such as going to that island, well it was a metaphorical island, it's not geographically speaking an island but there will be so much police forces around that it will become an island. So I don't believe that physical actions like going there with a race, fierce and say no, no, no, we will be of any usefulness but definitely we have to organize. I don't believe much into centralizing action because I think the centralized models belong to the past so I really think that we have to make it sure that everyone will be able to participate in its own way. We as La Quadrature du Net, we produce tools, we give ideas, we provide means for people to do things but it's not exclusive, anyone has the way to do their own. Of course we will discuss for instance with our friends of Net's Politik and what's the name of that new variant that was created today? Oh yeah, you may be right. This and the Tete Tete and bits of freedom in the Netherlands and the Open Rights Group and XGIA and the Free Culture Forum in Spain and so on and so on. So if you ask me what action will it be, I cannot tell you today because I still didn't find out but it is clear that we need to organize and that we need to use the Internet for that and yeah, stay tuned for some more exciting campaigning. There's a short statement from me. There's a lot of talking about the content side so they should not be able to control the content and therefore we should fight for the free Internet pretty much. The main problem is that the Internet itself cannot be free because it's all based on commercial structures and it's based on comp. Oh, please don't die. Yeah, yeah. Actually really, really building our own Internet. Yeah, yeah, that's it may come sooner than later. There are lots of several interesting questions in what you asked. First of all is the question of the merger between telecom groups, telecom companies. There is no pure player Internet service provider in Europe, I think, but they were all sucked in by telecom operators that are now merging with media groups and so on. So we have a concentration in Internet providers that is comparable to the concentration in media group and that should be addressed as a policy problem, as a policy question and that's first point that I think is relevant. Then this concentration gives incentive for those actors to restrict more and more access and that breaches to net neutrality and that's another issue I could have talked about for one hour and I really think we need to address this once again by policy, by declaring that Internet is a common good and therefore must be protected. Today in France was released a very good, sometimes good things happen in France, that's very rare, a very good parliamentary report about net neutrality that's two members of the parliament, one conservative right wing and one socialist left wing that together released this 80 pages document with recommendations about how to efficiently protect net neutrality for freedom of expression, for innovation, for open business and so on. We'll be working probably tomorrow morning, we'll be released or English press release about it along with translated bits of the report and we'll try to publish more of it. So this is also one part of the answer and another question that was contained here and I'll try to address is what will we do when they will have finished to break the Internet into parts, when they will have turned the Internet into television, spy.nul and make it useless? Then this is the moment when we will have to reinvent the Internet and rebuild it maybe from scratch. We the geeks, we the hackers who built the Internet once, I think we will be able to rebuild it and to build it again twice. So this is when we will put the antennas on the roof, this is when all the Fryfunk people and OpenMesh people will be the new architects and for this we need an open spectrum policy that uses, that allows people to use airwaves for free without a license and this is also one very good news that we obtained yesterday in the European Parliament. Those are amendments we pushed on the recommendation of the European Parliament about EU spectrum policy that got adopted. It has to be confirmed in plenary but that literally allows for citizen usage of airwaves so we might have a small window of opportunity here to rebuild the Internet someday. Yes, my name is Sandra von Lingen and I have a legal background. I work for an association called Gruel which is an academic association of 5,000 IP persons in the broadest sense mostly lawyers, judges but also from industry, also from copyright owners, the whole range also creative people and I'm responsible for international affairs. So I have this, for me the European Commission's strategy is not so opaque and I agree to a lot of points that you have raised but I would like to add a few things because I think there were a few things that you didn't maybe mention which go in the same direction. It is true that I think that on the national level governments didn't really manage to enforce the way they wanted to or to control so they put it on the European level and on the international level. The whole actor process has shown that it has been out of a democratic process so this was noticed even by let's say conservative IP lawyers and the other thing is that the European Commission right now with a whole package of IP measures is very much pushing IP protection at the moment so there's a change at the moment. It's a whole package, it's not only a file sharing or copyright, it's a patent law, it's a trademark, a whole review of the trademark system so there's a lot of things going on and what wasn't mentioned here which is very important for you is that Tillmann Lüder who is in charge has been replaced by an ISP lobbyist so this is something very relevant so you can be prepared to a lot of counter wins let's say in Germany, Gegenwind. My point is I think that you know I work for an academic association, it's not a lobbyist association and the most important academics in Germany are dealing with the same stuff than you and you may know that they have signed a petition against Akta. There's a whole group of academics in Europe that have signed a petition against it and I think that there are three ways to you know counter lobby if you think so or just counter balance the tendency. It's the European Parliament, you have noticed it, so lobbying with the European Parliament representatives. Academics I think you should try to contact or get in more close touch with academics because especially in Germany you may not know but I know because I know the actors at the Max Planck Institute and with Kruhe there's a change of let's say of how do you say of generations so there are a lot of people who think more in the spirit than you do and they are just changing their views especially at the Max Planck Institute. It's a very important change in Germany so this is you should talk to these people if you want to put your views through because they have a lot of influence near the European Commission. They talk to them every day so they're really on a hello basis and the third thing is I think we should a little bit trust the courts because I think that the courts do control a lot and also on the German level we have seen that they have turned down a lot of things and also the European Court of Justice it's getting more difficult when the law is changed so you have to block it before the law is changed and I think this goes through a dialogue with not with the industry it will be difficult but with the academic world and through this vehicle with the parliament that is my impression because this is my work I do it every day so people are listening but it's going to be more difficult now especially on the copyright sector. This is a new person in charge and this is clear. I thank you for your comment it's true that I should have mentioned that change in the European Commission where that former IFPI so the international lobby for phonogram producers for record producers become the person in charge of copyright in the European Commission is really a sign of something. It's true that yeah we're trying to get to talk with as many people as we can but I take your point that going and talk to the academics may not be as yeah they may not be as conservative as I might have imagined. Also when you mentioned other policies related to trademark and patents it's obvious that yeah patents can go really wrong you know especially when you took a patent on seeds and things like that but the main difference I think from the patents trademark and copyright is that patents and trademarks mostly apply to corporations and economic actors you could argue about software patents but I think they're just a bug in the patent system they should not should not exist but copyright for the first time in in its history is now turned against the public it is turned against individuals the the what was obvious 20 years ago uh was that copyright being based on the capacity of actors to produce copies who can produce copies of vinyls or CDs or or cassette uh no high number of cassette and so on was only commercial actors now with digital technologies when we all have in our pocket a device capable of making millions of copies per hour then we become all producers of copies and we become all regulated so to say by copyright so this is why I think we really have an emergency with a copyright that is gone crazy that is gone you know but uh because it is turning against the public it is turned against individuals and it is turned against usage that we have in our own private sphere you know on apartments or you know you know you know literally in our pockets so I think this is why I only mentioned copyright but I thank you again okay thank you very much Jeremy Simerman we have to move on I'm sorry thank you
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As the crusade against sharing of the entertainment industries goes on, we may be about to lose the most precious tool we ever had for exercising our fundamental freedoms and practicing democracy: the Internet. How the future moves of those desperate, yet powerful industries would radically alter the shape of the Internet? How the ACTA agreement may durably bypass democracy and hurt or freedoms? How to react efficintly as a citizen?
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10.5446/21585 (DOI)
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Das beste ist, um das auch verständlich zu machen. Ich habe hier eine Begründung von Herrn Stahlsberg. Willkommen hier bei der Co-Funding-Konferenz. Danke für die Zeit. Ich gebe nur eine kurze Begründung auf was Diaspora ist, damit es jeder weiß. Ich habe ein paar Fragen für Sie und alle in der audience, die sich mit Fragen auf die Frage fühlen. Wir haben nur 15 Minuten, aber wir machen die meisten davon. Diaspora ist eine decentralized, open-source, sozial-media-Netzwerke. Nationalwy sec.<|tt|><|translate|> Anh upcoming und wir haben in Deutschland verschiedene finanzielle Unternehmen gemacht. Wir haben gesehen, dass einige davon überfinanziert wurden, mit etwa 120 Prozent oder so. Aber du hast aber überfinanziert, 2000 Prozent, was eigentlich sehr gut ist. Es ist wirklich glamm, aber ich bin wirklich interessiert, was dir zu diesem Thema passiert. Denn das Projekt war im Tickstarter, das kam genau ein Jahr ago, und du hast dir das initiale Fundraising-Gold von 10.000 Dollar in 12 Tagen erreicht. Und in den nächsten Wochen, all of a sudden, du hast mehr als 200.000 Dollar gekauft. Wie fühlst du dich, wenn alle diese Leute auf deine Direktion starten, ohne dich, ohne dass du eine Einladung von Knoten hast? Ich war eigentlich sehr verletzt. Wir haben auch Raphael wirklich aufgemacht, weil sie da zu Hause sind, und have ein Votgan mit Zeug Node... hat mit allen Leuten eine retire Witze, die sich mit uns vom emphasized fibers LAN zusammenj Amen ist, sondern mit den 1970 Jahren. Es ging dann einfach soon. Also waren wir in Deutschlandatanern, Was haben Sie denn gesagt, die $10.000 für uns? Die $10.000 war für uns, um auf die ganze Zeit für vier Monate zu arbeiten. Und einfach zu sehen, wo wir gehen können. Es ist ein hartes Problem. Wir haben seit Februar seit dem Code geschrieben, dass wir Angst haben,ava ein Wir haben uns das $20000-000-Gericht geplant, weil wir uns 6.000 T-Shirts gekauft haben. Ja, ich kann das vorstellen. Ja, natürlich sind die vier Founders. Ihr habt nicht wirklich für diesen Erfolg vorbereitet. Ich habe das Video gesehen, das ihr... Ich bin sorry. Nein, eigentlich habe ich es sehr lieb. Ich finde es sehr authentisch, vielleicht. Ja, ich glaube, das ist wahrscheinlich ein oder andere Fondation. Das ist eine Idee von vier Leuten, die wirklich eine Idee haben, die sich vorwärts bringen wollen. Aber die haben eigentlich keine Ahnung, wie sie es tun wollen und die wirklich nicht genau sagen, wo sie enden wollen. Aber nonetheless, die Leute, natürlich liebten es sehr, weil sie sofort gesehen haben, dass es ein großer Alternativ für Facebook wäre. Oder vielleicht war es ein bisschen David vs. Goliath-Effekt. Also, wie war es für dich? Ich glaube, du hast einen Punkt, wo du dachtest, hey, sie haben uns nicht wirklich als Diaspora, sondern sie reden alle über Facebook. Was ist unsere Identität? Ich glaube, wir waren das erwähnt. Wir waren sehr careful in unsere Wörter, zu sagen, wir wollen etwas positive machen, was nicht existiert. Wir haben wirklich nicht Facebook benutzt oder wirklich in allem. Es ist ein bisschen wie die Medien, die sagen, oh, diese Kinder reden über Antifacebook. Es ist etwas verrückt, zu sein als du ein paar Kinder, die für 10.000 Dollar haben, und du machst 2.000% von 10.000 Dollar, aber dann zu sein als, das ist die Antifacebook, die 50-Billion Dollar-Komponente und 200.000 Dollar. Es ist schwer, diese Forderungen zu setzen, aber ich glaube, wir waren ehrlich und sagten, wir wollen das machen, ob wir das Geld bekommen oder nicht. Du kannst uns helfen, wenn du willst. Wir wollen das machen, dass wir es jeden Tag besser machen. Das ist wirklich toll. Das ist alles, was du kannst, als ein Mann. Wir werden jetzt unsere Team bauen. Es war dieses wahre, jumpstartige Start, um eine Haltung zu bekommen, eine reale Organisation. Das wird immer weiter auf die Asperung, Entwicklung und Innovation in den Zukunft bringen. Ich glaube, das ist ein interessantes Punkt. Wir reden über die Öffnungs- und Software-Default. Dieses große finanzielle Erfolg, das dein Projekt betrifft, nicht mehr in den Öffnungs- und Startup-Kontext. Das hat dich in einer Position, in der du nicht vorbeiziehen warst, und in der du für deine internen Strukturen zu adjustierst. Wenn du zu diesem Punkt hast, ist das komplett. Ja, ich glaube, es ist wirklich toll. Ich glaube, es gibt nicht genug Öffnungs- und Startups. Ich glaube, dass unser Erfolg mit Crowdfunding uns wirklich erlaubt. Wir werden ein Öffnungs- und Start-up-Kontext bauen. Wir machen das, wir schreiben Öffnungs- und Software jeden Tag, aber es ist klar, dass man das wollen will. Es ist klar, dass man uns Geld geben will. Das ist sehr... Das bedeutet viel. Es ist wichtig, dass jemand etwas will, in einem testbaren Weg, ein wichtiges Ding, in der man innovieren kann und online Dinge machen. Du hast auch die Erfahrung, dass die Leute gesagt haben, dass sie genug Geld haben, aber sie helfen, mit Kodin oder Marketing zu helfen, oder so weiter. Also, haben die Leute dort, die dir helfen wollen, auch auf diesem Ort? Wir haben so viele E-Mails, die ich nicht auf meine E-Mails gesehen habe, für eine gute 3-Wiebend. Das ist ein weiterer Punkt, was wir nicht bereit waren. Es war ein Influks- und Kommunikation-Authentzen. Ich war in der Schule und wollte finals machen. Es gab viele Leute, die helfen wollten, aber es war so, dass wir wissen, was wir wollten. Wir wollten, was wir wollten, um in einem Kabin in den Wien zu gehen. Das war wirklich all das, was wir geplant haben. Wir haben gedacht, dass die Leute uns Geld geben, um das körperliche Ding zu ändern, weil wir jetzt viel Geld hatten, das nicht so viel Sinn zu uns machen. Wir haben sehr kognizant, um nicht zu... Wir haben natürlich Geld, um die es Sinn macht, um die Erkrankung zu erhöhen, um unsere Produktivität zu erhöhen, aber nicht zu fundamentaler Veränderung, warum wir es gemacht haben, weil wir es gemacht haben, weil wir Spaß haben. Wir haben noch viel Geld, um das zu erhöhen. Ich denke, das ist auch eine andere wichtige Sache, um den Grundeignissen in general, dass es die Menschen mit den Passagen finanziert. Ich denke, dass es successfully für mich und die Leute, die wirklich versuchen, was sie tun, und sie wollen und tun, ob sie das Funding oder nicht. Wenn wir nach diesem letzten Jahr schauen, das ist das Zeitraum, was wir darüber reden, nämlich den £100, thunder Kevin O's, Laurent Nein, ich denke, es ist dasㅠㅠ azCT dass ich Aber ich denke, dass die Exposure und die Idee, dass die Diaspora grundsätzlich ein Grasser-Schritt ist, hat es einen großen Sinn, eine Grasser-Schritt-Schritt-Schritt zu finden. Ja. Ist es eine Kommentare oder eine Frage von unserem Audienz? Wir haben fünf Minuten. Nein? Hier. Wir haben ein Mikrofon hier. Hi, Alex Schultz. Ein einfaches Frage. Wo ist die Kote jetzt? Wo ist das Projekt? Was sagt ihr jetzt? Ja, es ist ein aktives Availment. Wir arbeiten noch nicht ganz lange. Wir sind in einer privaten Alpha-Phase, aber die Kote ist auf der Webseite open-sourced, die Github.com. www.diaspora.com. Wenn ihr euch was nachdenken wollt, schreibt es mir in die Kommentare. Alles, was wir tun, ist komplett öffentlich und open. Wir machen das, was wir tun, wir haben keine private Repo oder was. Wir planen, eine ziemlich große Erleichtung in den nächsten sechs Monaten, was für die endgültigen Änderungen wir haben. Wir haben unser kleiner Gruppel Alpha-Testern. Es ist jetzt aufgerufen, weil es so ist, dass ihr nicht mehr viele Leute braucht, sondern es ist ein bisschen ungewöhnlich. Ein zweites Frage, vielleicht? Mark Zuckerberg ist ein Investor, ist das richtig? Was sagt ihr euch? Ist es eine Influenz von euch und von den Resultaten? Ja, Mark Zuckerberg ist einer unserer Backer. Es gibt auch Donations- und nicht Investments. Wir sind sehr glücklich für seine genaues Donation, aber er hat nicht mit uns in den Kontakt oder was. Er wollte nicht ein T-Shirt. Ich glaube, du hast viel geholfen, um internationaler Erweiterung zu bekommen. Wie ist deine Beziehung mit den Kickstarter-Geräten? Es ist wirklich gut. Sie sind wirklich coole Leute. Einen der Leute, die dort arbeiten, ist das, was eigentlich passiert, ich weiß, für lange Zeit. Sie sind wirklich coole. Sie sind definitiv... Ich habe nie wirklich gehört, dass ich von Crowdfunding gehört habe, bevor wir das gemacht haben. Ich weiß, dass du gesagt hast, dass es in Deutschland ist, aber ich glaube, es ist auch in den US. Wir haben definitiv jede Kekserter gebrochen. In unserem Projekt. Wir haben alles gebrochen. Wir haben eine E-Mail, ein Crash-Kekserter-Server. Max, bevor wir zu klatschen, ich möchte euch vielleicht ein Hinweis geben, oder etwas, was für dich wirklich ein primärer Erleichter ist für deine Diastro-Story. Was möchtest du mit unserem Publikum teilen? Was für den Crowdfunding? Was du gelernt hast, was für dich das größte Zeichen ist, und was möchtest du mit allen anderen, die sich über ein Projekt auf eine Crowdfunding-Plattform betreiben? Ich denke, das wichtigste ist, dass du dich auf das Crowdfunding-Fundern und das nicht mehr verabschiedet. Ich denke, das kommt aus. Es könnte ein tolles Weg sein, um zu starten. Es kann ein tolles Weg sein, um zu starten, wie ein Business oder so. Aber ich denke, es muss wirklich von etwas, was du überwinden musst. Du musst sicher, dass es in deinem Bild etwas, was du wirklich passioniert bist, was du überwinden musst. Und das ist etwas, was du tun musst, wovon du die Funding erinnert. Es ist ein Zeichen, dass du ein unstoppiger Erlebnis für dich bist, um etwas tolle zu machen. Vielen Dank, und wir wünschen euch allen einen guten Erfolg. Vielen Dank.
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Interview mit Maxwell Salzberg, Diaspora
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10.5446/21586 (DOI)
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Hello. I really like Thomas' idea. We should all Twitter. Really great stuff happening right now in Frutustas Palas. I want to take this next 30 minutes to talk about an idea that I think is quite exciting and quite relevant for this audience. I'm going to be talking about collaborative consumption. The way I'm going to do it is a bit of a remix. I'm going to take arguments from a lot of different people and throw it together, pulling people from Nobel Prize winners and Lauren Schlesig and Sean Bonner and a lot of other cool thinkers and then conclude by driving the ideas forward with some design challenges. All right. So first a little bit of context. We're living in a hyper-consumption world. I'm not the first person that's going to be up here to tell you that pretty much we're consuming ourselves to death. You basically all know the horrible predictions. But we keep wanting and buying and it's getting worse. And the thing is often consumers are put in as part of the blame. And it's true we are the people that are purchasing things and driving this hyper-consumption world. But I also think designers and manufacturers are playing an important role in the equation as well. I mean, unfortunately, the predominant business model right now is designed for the dump. That means making products that on purpose are obsolete the moment you take them out of the box. You know, it's people that are actually thinking it's, I mean, it is the lucrative business model, which is why people do it, but that they're kind of sick to think you're making something that you have to throw away pretty much the moment you start using it. There's a few common perpetrators in this designing for the dump paradigm and pretty much they're selling you, you know, objects that are going to get scratched and get throw, you have to throw them away and get the new model. And in our fragile world, that's unsustainable. So we're overfilling the landfills and it's not a pretty sight. But you know, so maybe you're somebody that says, you know, I'd rather store the stuff, keep it for a rainy day, maybe I'll use it, you know, under different conditions. Well, that's also a solution that people have. We're seeing an explosion in the industry of self-storage. In the U.S. alone, the very hyper-consumption nation, there's over two billion square feet of self-storage. That means a land area three times the size of Manhattan is dedicated to storing people's shit. And you know, in Germany, I think in general Germans are more thrifty and more consumption conscious and they don't have quite the same illness that people in the U.S. do. But still, self-storage is on the rise. Within the last ten years, Germany went from having zero storage facilities to 70. And in Europe, we're seeing over 1,500 storage facilities when they only used to be a handful. So this is a trend, it's on the rise, and people are willing to pay premium rent on storing stuff. But lastly, you know, no matter where you're keeping your things, as Bruce Sterling would say, it takes a hell of a lot of energy just to maintain all of this stuff. You have to heat it and cool it and care for it. And the time that you spend taking care of your stuff is time that you don't spend with your family, with your friends, with yourself, with your society. So when we're investing all of this energy in, you know, taking care of all of these objects that we own, we really have to ask ourselves who's being owned by whom. All right. So enough of the Doomsday stuff. I wanted to get some audience interaction with all ten of you. How many of you own a power drill? The people in the front, that's an interesting trend. The active ones here. How many of you that own the power drill have used it in the last, let's say last month? Okay. Just a handful from there. How many within the last six months? I'll give you a little bit of a chance. Okay. So some active drillers. But there's still quite a lot of people that own a drill that haven't even used it in the last month or last six months. That means there's this power drill just sitting there on the shelf with all these spare cycles. You know, that's a lot of potential and a lot of use that we could be getting out of the power drills that are otherwise just collecting dust. So what if there were a way that we could capture those spare cycles? You know, what if we could actually get more efficient about things like power drills? You know, we could have like apps that tell us that all the available power drills are in our neighborhood and send a notification to that guy who kept raising his hand that he's got a power drill and say, you know, it's available, you can borrow it. I mean, this would really be, you know, a boost to how we use objects more efficiently. And this is actually where I see hope in our situation. You know, I see one clear advantage that we have that no other generation before us has, and that's the power of our networks. With networks, we can share better and we can provide infrastructure better and we can leverage these networks to build by and collaborate locally and efficiently. We can shop smarter, share better and use our networks both online and off to reduce waste and improve the economy environment and even have a good time doing it. So today, I want to talk about new forms of collaboration and consumption and I want to talk about the opportunities and goals that push us to be better to our planet and to ourselves. And have some water. Okay. So you might all be familiar with this symbol. We learned in school that it stands for reduce, reuse, recycle. And I think it's a pretty powerful concept. I mean, first, let's just reduce things. Let's buy less shit. Second, let's reuse the stuff that we do buy. Let's reuse it more. And lastly, when we reuse that stuff to its last possible point, we recycle it. Well, I want to recycle this diagram for today and riff on it a little bit. So let's first talk about reduction. That means buying less stuff, which is easy to say, but also increasingly it's easier to do. There's a lot of people like this dude right here who are saying, you know, I don't need closets full of things when I don't need all this self-storage unit. You know, I can actually consolidate my life into 100 items or less. So there's people like galvanizing around terms like cult of less, tech nomad, who are really aspiring to this principle of having less stuff but having it better. So he says, Kelly Sutton, the founder of the cult of less movement, I will eliminate a large part of stress in my life and I will truly cherish the few things that I own. So what are you waiting for? Let's go sell some stuff, get rid of things, you know, just throw it away, those fancy ball gowns and tuxedos and nice shoes that you keep in bubble wrap and nice Christmas presents from well-intending relatives that you never took out of the box. We should sell that stuff because sustainable practices mean that they last, that they navigate and last through time and space where other stuff just cracks and falls apart. I think in this day and age, in the 21st century, we have to rethink our relationship to material possessions. The things that occupy our time, the things that are closest to you are the things that take up most of your time. So these are the things that you have to be the most wise about when you purchase. So choose wisely. You can sell the junk, take the money and get a real bid. So as Bruce Sterling says, these are great guys, really good for sound bites. Get radically improved everyday things. Just enough is more. So yeah, we've got things we're using everyday, laptops, phones, beds, these things we should care about, these should be quality over quantity. And the other stuff, like these power drills, like let's innovate around reuse. So if it's not as efficient to own that power drill, it's just efficient, it's more interesting, let's say, to use the power drill. We're talking about having access to the power drill. And in a lot of ways, you'll find more wealth in use than in ownership. And access is actually better than ownership in many examples. So the interesting news for our day and age is that it's getting easier and easier to access things. You know, we have places like this lovely beta house, a co-working space here in Berlin. And you know, you can rent a desk, you can hang out with fellow digital nomads, and you don't have to buy a printer. Like how cool is that that you don't have to repair and refill and maintain and eventually dispose of a printer because this place provides shared infrastructure for you. And you can go there and you can benefit and have access to these things. And you know, it's just cool places like the co-working spaces, but there's also all sorts of P2P services that are coming up that are allowing you to share cars, like Zipcar, or to share accommodation like Airbnb and couch surfing, or to share stuff like neighbor goods. There's a whole slew of these sites. And they're making it more flexible and more agile and more social to share. And what's kind of cool too is, you know, sometimes you look at these sites and you're like, that's cool, but isn't that for like low budget 20-somethings and students? But actually there's a lot of interesting business models on the luxury end as well. So there's collaborative consumption in places like the Berkeley Hotel. It's a pretty exclusive hotel in London. And they've created this thing called the Fashion Trunk. And they fill it with high-end luxury goods, jewelry bags, et cetera. And the guests can come in and they can wear the stuff and use it during their stay. And at the end of the stay, they either can purchase it or they just leave it back in the trunk. So I think this is an invitation for us to really rethink, to say, collaborative consumption can work. It can work for the fashion trunk. It can work for cars. It can probably work for lots of other things we haven't even thought of yet. So that's my invitation for us. Oops. Just kidding. Can I skip to one? Never mind. No. So, okay. To distill this idea of what is it that makes an effective collaborative consumption model, we have to first figure out what are the characteristics of a shared object. So first you need idling capacity. You need those drills that are sitting on shelves that have spare cycles. We need a setty at home for power drills. We need to be able to take advantage of this surplus that makes collaborative consumption possible. And now we need critical mass. Couch surfing isn't going to work if you only have two couches. So supply feeds more demand and we need these systems to be robust and to have a critical mass so that they're interesting and attractive for users. And then trust. Trust is another thing. It's easier said than done. But it can grow organically and there are a lot of mechanisms to build in to sharing sites and platforms. Mechanisms that foster trust. And some of those come through things like common governance. You know, having conflict resolution that's easy and cheap and having the resource owners partake in the decision making processes. We can learn a lot from how the commons are governed in other spaces to figure out how to do collaborative consumption better. So now I want to invite you to rethink and to think about how you people like you, people in this room, you know, not only our consumers but also designers and entrepreneurs and the people that understand the world's most powerful communication medium in history. I mean you are the people in this room that can help us rethink. So that's why I want to have an invitation today to rethink. To rethink consumption, to rethink use, to rethink design and manufacturing. And to do this I wanted to end the talk with some design challenges. So we can talk in abstract but it's also really cool to leave here with some ideas of, okay, what can we do next? What's possible? So I like this idea. There's a lot of phones that accept multiple SIM cards. So you can have one shared object that actually accepts data from multiple users. So you can, you know, slip in your SIM card and you've got like your address book and your contacts, whatever, your personal settings. And that object then becomes, you know, personalized for each person that's using it. Can we do that for other objects? You know, can we do that for cars or refrigerators or printers or vending machines? Can we personalize shared objects better? Or imagine a library that doesn't just offer books. Like let's explode the idea of a library and think of filling it with things like tools or electronics or, you know, I don't know, jewelry and other sorts of cooking appliances, things that we could actually think of as a common pooled resource and, you know, have it function the same way libraries have for centuries, but offer objects that all of us could benefit from. So let's diversify libraries. Also, here's an idea. In free culture there's this concept of open layers. It's saying, you know, instead of giving someone a compressed video file, give them the raw footage, the audio track, the transcript, the images, everything separated out in different layers because then it's really easy to remix and rebuild from those different layers. Like let's take this idea and, you know, do it with objects. Like let's create objects that are easily remixable and with open layers. Or here's another fun idea. What if we built in modularity in our objects? So instead of when your iPhone gets scratched, you don't have to throw away the whole thing. It's more like Lego-fied and you can take the pieces apart and you can replace things a lot easier and you can also customize things easier. We can build in modularity into products that we don't have to throw things out the moment one thing doesn't break. And here's another suggestion. There's a speeder in Dallas that's reconfigurable at the flip of the switch. It's like got all these different combinations of seating and stage and where the actors can come in and all these things. And this has transformed that space into being a really rich cultural hub. It used to be just a boring theater. So can we take this idea and transform all sorts of spaces so that we don't have to always have all this idling real estate, which Berlin knows a bit well. But we can also think as architects about how we can build in customization and reconfiguration so that people can transform spaces and get the most out of them. And lastly, I think a very powerful idea. You think about having a baseball mat. And when you first buy it, it's really stiff and it's hard to use. But over time, it starts to mold and through use, the baseball bit becomes better. What if we did this with more objects? That the more you use them, the more value you got. Things then depreciate with use. They got better. I mean, we can do this thing about it in a physical way, but we can also think about it in a data way. Things that can collect data, usage data points, user metadata, this sort of thing. Things that get smarter, better, more useful, the more often we use them. And then we can really turn the consumption paradigm on its head. So there's a lot of potential. There's a lot of business opportunities. There's a lot of creative opportunities for adventure some smart people like you. So I encourage you to reduce, reuse, and rethink. And let's take a cue from the makers. Let's give objects a new life by thinking creatively and collaboratively about them. The maker ethic is actually really empowering one. It's saying that we have the tools and the knowledge to make a difference. So actually together we can really change the world. Thank you. Thank you, Michelle. Do we have any questions? There are questions. I was wondering when I heard your speech. How about Germany? Because in America, for example, the idea of car sharing, so sharing your own car and putting it into a pool, it seems to be way more common than in Germany. Are Germans, I mean, you're the person who can talk about this, are Germans more focused on owning something? Well, I mean, in Germany you have Mitfageligenheit. So I actually, I mean, this idea of a ride board or a ride share is actually very prominent within the culture already. And actually more so than in the US. People are like, you get in the car with a stranger. So I think there is already practices that are built in within Germany. So I think also these things are effective when they build on practices that people are already familiar with. And I think car sharing has just as much potential here as it would in a place like New York or something. Okay, I don't see anyone asking a question. There's one. Oh, that's one. Okay, sorry. Yeah, I have a question. I thought the idea of sharing power tools is lacking one thought, because, well, it's for many men, I know that it has a very emotional side. And they might not like to share it. Point taken. I think, yeah, I mean, well, I think these systems are powerful when they're opt in, of course. So nobody's forcing you to share a power drill. But I also think, you know, we can also build in mechanisms that allow you to have, you know, insurances or other sorts of like reputation management or other things where you feel like, okay, there's enough trust built up in the system so that I'm okay giving it to somebody else. I hammer is better. Next time. Republic of 12. Okay, there's a question. This is all right. I really like the idea of sharing stuff, which you just told us. And on the other hand, there's this problem that many products are just, you can't repair them anymore, because they're just impossible to take apart. What do you think of how could we consumers start to make more use of old stuff and try to encourage ourselves to repair things? Yeah, that's a fantastic question. I think, so yeah, on both sides, as from the designers, they need to build more modularity. So we can do these things. And also as consumers, I think this idea of becoming makers and of if you can't open it, you don't own it and having curiosity about objects. So, you know, I also have an Apple product and I don't know what's going on inside of it. But maybe I should get over that, that, you know, restraint and open it up and start to understand the pieces because I think once we understand how the things fit together, we also create drive and demand in a market for things like components and smaller pieces. So I think the first step is curiosity and knowledge. And then the second step is more active. Then we can start building and the market will probably reflect the activities of consumers doing that. That's a question over there. And given that libraries already exist, why do people then still buy books? So I really like the idea, but I think there must be millions of impedance, otherwise it would have been in place in some, like, yeah, for some products already. For which part already? Sorry. Well, for instance, for books, I mean, there have been libraries around for a couple of hundred years and people still buy books. So what stock people come to the library? I think one doesn't cancel the other, right? I think they're complementary systems or they're systems that function in different ecosystems for different reasons. So there is actually tool libraries. There's some in various cities and they use the metaphor of a library and people still buy tools. They sometimes buy tools to put in the tool library or they have tools because they have emotional attachment to their power drills that they don't put in the library. So I think that there's still a lot of opportunity to explore this idea of a library without saying the market will completely collapse and no one will buy things the same way. Any more questions? I don't see any raised hands. So thank you, Michelle. We're going to take a five minute break and then we're going to see one of the speakers I'm looking forward to the most. So Lana Larsen, the managing editor of Global Voices. See you in five minutes.
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The world is ending, and we, the insatiable consumers, are at fault. Our homes and landfills are overrun with junk designed for a limited lifetime. But before we choke off the planet, there’s something we can do. Unlike any other generation, we can better provide and share infrastructure thanks to network technology. We can buy, build, and collaborate locally and efficiently. We can shop smarter, share better, and use our networks, both online and off, to reduce waste, improve the economy and environment, spare our bank accounts, and even have a good time and make new friends doing it. This is collaborative consumption, and I want to talk about its wonderful opportunities.
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10.5446/20880 (DOI)
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Music From London, England, please welcome Keiichi Matsuda. Applause Hi. Since I'm talking to you in the famous comedy club, I thought I'd open with a joke, but I don't know any. Have you all got glasses? If you don't have glasses, maybe somebody can hand them out. I think they're at the back. You don't need them yet, but for later. This talk is augmented hyper-reality. I don't think I have to explain to you what augmented reality is. I think everyone's familiar with it. Everyone's had maybe first-hand experience using a phone, or maybe their webcam, or maybe the 3DS or something similar. It's come into our lives in a big way, and it's nice for me because this is my area of interest for a couple of years now. But I think so far we've only really seen just the tip of the iceberg, just the beginning of what augmented reality is capable of. I don't think augmented reality is about these kind of way-finding device or any kind of cheap, giving things. I think augmented reality is a really important thing to happen, and it could have some major effects. It could parallel to the internet or something. What I really think augmented reality is about is about bringing information into our environment. Taking it away from the screens or the newspaper or any kind of screens you have in front of you, and actually liberating it, and bringing it out into real space. I think this is really what drew me to augmented reality in the first place. I'm a trainer and architect. I studied my masters at the University College London. I think it's something about the way that we can use information to define space, which is really interesting for me. I think that in the future we're going to see that the virtual layer of the city becomes a very important part of our experience of the urban environment. This is what augmented reality is about. It's about the virtual overlaying onto the physical environment and understanding what issues are raised in this and how we deal with them. I think there's a lot of issues surrounding privacy and politics and social interaction and economics that I can't deal with everything, but I'm just trying to start by identifying these key issues and then trying to start by looking at how we can approach this from an architectural angle. I'm going to start by showing my son a domestic Robocop, so we can have a light sound. I'm going to show you what I'm going to do with this. Cut up the filigree with two hot plates, one PG tip, two bags and a green mouth. Now get the skin milk from the reef and a derailleur. Carefully pour boiling water into the mug. You're even great when you're waiting for the tea to brew. Why not browse some recipes and suggestions to help you decide on a new set of tips? Oh, it's getting faster! Wow! The speed is slow, so you can adjust it to 4 steps faster. Thank you. This film is kind of a satire, I guess. I'm quite critical about what would happen if we have this environment of ubiquitous media. If we allow the internet, the network to come into everyday life and to lay over every environment, then I'm quite worried about what would become of our city. There are some interesting things about it as well. For example, the social network module is coming up, where you have the environment around you. It's starting to think about how we can use space to better understand the information that's presented to us. Here I'm using lots of the Z-space here to relate to time. There's a lot of psycho-geographical factors that we can put onto this world and use to try to understand the data we're dealing with. Also here you can see there's many gadgets, like widgets, that you can download and add into your world. Part of it is a network sponsorship and a premium model, but part of it is also being able to graph little bits of what you're interested in and bring them into your own world. You can essentially define your own environment just as we put posters up on the wall. You can see here also here I put some tape on the table and some dots on the wall. This is really just so I can film it, because when I was doing the composite thing, you need to do that so you can match it. I know that in augmented reality, then, you know, picture tracking things are getting much better now. I found it really interesting that we could start to think about an environment which is speaking to the device rather than speaking directly to us. What's happening here is that the computer or the phone or the camera or whatever is reading the environment and then it's relaying this information back onto us. So we have this innate mediation. I'm going to walk you through a bit of the project now. So these are some of the concept images from the project. This is another one that I didn't end up making. But you can see there's some kind of wayfinding elements here and some kind of billboard style advertising. I don't really think advertising would work like this because obviously you'd find much more subtle ways to introduce it in digital lives. But I wanted to make a comment about how important these kind of things are in our current model. So my project is about augmented reality. But this is really part of a larger paradigm which is called augmented space. Augmented space is seen as a kind of progression from virtual space and virtual reality. And virtual reality is this great idea we have in the 90s that we plug ourselves into the network and upload ourselves onto the Internet. We never have to be in real life again. But although this sounded like a great idea to many people, we actually rejected this entirely and we decided this is not what we wanted. So we're now in this paradigm of augmented space which consists of augmented reality of us but also other things like adaptive computing, wearable interfaces and tangible interfaces. And these kind of sensor arrays that require to support it. And this is an interesting and important thing about augmented space. It requires a high level of surveillance. So everything is supported and tracked and data is produced at the landing rate and then this is relayed back to us. So you have this kind of balance between the functionality of augmented reality or augmented space and the negative effects of surveillance also as well. I was interested as well that in the last film you thought I had this keyboard that I brought up, right? And as soon as I made this I was like why did I do that? It's such a bad idea because this is based on the typewriter and we're going to find so much more sophisticated ways of doing it. But we're still going to need ways to modulate our environment and to input the goals. So I thought the cockpit was an interesting model of how we could possibly do that. This is also very psychogereraphic. It has all the controls you use the most right in front of you and then someone towards the back which is also important. So this is kind of a model for interspace designers. This is again about the environment speaking to the device and the user. So here's another important idea. This is about ideal space. This is something that we first came across when we were thinking about virtual reality but it holds true augmented reality as well. If we can have any space, if we can choose exactly what our environment looks like, then what do we choose? How do we define what environments we'd like to live in? I think for some people it's maybe something natural like being on the beach or walking through a forest. Some other people, you know, it's a Renaissance villa somewhere or maybe like a modern house somewhere. I think all of these things are based on a concept of luxury. And I think the concept of luxury is questionable under augmented reality because it's kind of abundant, right? It's abundant media. So if we're looking at things like the modern villa, then how do we define something which is good or ideal about that? Maybe it's the quality of the material or the quality of the craftsmanship or maybe it's the resolution of the detail or the kind of speeding of the space. These things are much less important in augmented reality but we don't need to worry about gravity or structure, anything like that. So it was a challenge for my teachers and universities to understand that I didn't need to know about structural space. So that was the problem that I was thinking, you know, what is ideal space? And my answer is this. I think this is the ideal space. This is someone's workstation that they kind of customize with fragments of posters and their travels and their favorite books. You can see the computer there as well. They customize their desks up and I'm sure they have some completely illegible file structure somewhere as well. The idea is that you grow into a space and the space also grows into you. The space becomes a kind of projection of your personality. I think this is very similar to a lot of aggregators that you see, something like Google Reader or Twitter or Facebook, that you can't read the whole world. You can't read the whole internet. You can only read a small part that is relevant to you. So you just surround yourself with the things that are important to you. I think this has a much better idea of what ideal space is than the kind of ideal, the utopian ideal that you think of. So here we are. This is one of the first sketches of what your fantasy city may look like. It's quite rough, but in architecture we have all of these ways to talk about space. We talk about public and private. We talk about the program of space, about work space and living rooms. We talk about inside and outside. All of these things are becoming more and more irrelevant now. It doesn't really matter if it's inside or outside now. It doesn't really matter if it's public or private because this is the kind of private space that there may be people who are broadcasting publicly on Twitter or there may be people who are doing massively public activities within a private physical space. Likewise, you can have private bubbles within public space as well. For example, if you're on the bus and you've got your headphones on and you've got your head in the newspaper or whatever, then you're creating this kind of closed private environment within a public space. So these kind of terms are becoming less and less usable. To replace those, I have one idea which is broadcast and aggregation, which is the kind of way of describing space. Broadcast is what your kind of online persona, your identity is, that you give off to the world. You can see that at the top here, this person's made an avatar over their heads, which contains things like their status and their friends and their recent purchases and their favorite books and favorite films. I think I'm 27 years old and I think I'm probably just about a digital native today. So I've grown up with the internet and I think maybe I'm probably one of the first generations to really be really self-conscious about what I'm putting out there. I'm not very good at it yet, but I'm definitely conscious that every time someone types a photograph of me on Facebook or something that I don't like, I'm pretty un-tagged. And then the other half, this half is aggregation. So this is the kind of top set that floats around you. And this allows you to bring all the feeds that you're interested in and also ask for control. So these are two important parts to your next city. So let me walk you through a few of the layers of the anatomy of this. This is layer one. This is the top set that you see in white here. It contains all the feeds as well. Layer two is the field. The field contains location, space information, geotag information, and also any kind of apps or any other things which require them to be in a certain place. These are roughly kind of space and they're presented to you in a circular fashion, but it has a certain liquidity to it. So it doesn't need to be particularly in the right place, but it can sort of move around. You start to feel like the city is not this solid, thick object, and the architecture itself is more driven by events and circumstances and contexts rather than just being there forever. Third level is the skin. This is kind of like Georgian society you see here. And the navigation as well. It's not necessarily what I thought it was. Which is important. Absolutely good. The skin here at the Georgian facade, but it doesn't necessarily have to be. It can be anything. I just think that at the start of this thing, then people are going to want to show the world things that are familiar to them. But as this culture evolves, then maybe you start to see some more experimentation in terms of what's possible with the darkness. And then finally, here's the real physical, stealth environment, which is basically just concerned with creating kind of an insulated shell that you can stand inside and be warm and safe. It doesn't matter what it looks like, because you can decorate it after. This is all the layers together. It's what you can wait for guys, 3D time. There's two of cotton-o-glasses. It should be spread on the left, I think. Yeah? Okay, that's good. Okay. So, with the light stand please. Okay. All right, we'll just do it anyway. Kind of 3D, a little bit. It's a bit difficult because of the color, but hopefully you get some kind of sense of 3D. Okay. So, with the light stand, I'm going to go with the light stand. Oh, okay, you can do the light stand.pleas using this color. You Kind of run out of time project the final thing was supposed to be That you would have like her kind of reality as well and his reality and they would kind of merge together to form a Reality of that two subjectivities combined and it would be a very unique experience that are the only Yeah, so this is a this is the kind of level one the cockpit I Like I like the way an augmented reality that we have a different sense of scale that it's not about We can make anything any size so It's less about the dimensions in terms of meters, but it's more about the dimensions of the degrees of sight So the things can be big and small and it doesn't really make a difference Here you can see as well that he's kind of appropriated the space Be a bit like his living room even though he's in the cafe This this interface is actually contextual as well So I don't know if you notice but when he walked out into the cafe then the environment changed around him I think he was able to see kind of main route. I think it's very important. I mean this is obviously based on Highly surveyed as well, but I think it's nice that I'm The interface can be smart read read the action before without the user having to actually program or touch anything She's in the process of kind of curating her identity as well You can see that she's choosing what to put on her little avatar there and the idea was then that would appear above her head And here's the channel browser, which is really like insane 3d that doesn't quite work But you can see in this environment that this person is turning on turning on turning off different parts of their environment So the idea that in the same way that you can't see the whole internet you can't see the whole of the event to be either You just have to choose a little bit that are interesting to you, but you can mix the mash-up as well So the environment you create the environment you live in is With this as well I was also interested in in the kind of spatiality of these interfaces so that I mean this is a fairly traditional menu structure But it differs in that Because we have a kind of spatial form for it then every decision you make then the thing changes shape So you can kind of assign a shape to a decision when you see the shape you don't have to understand where you are You can automatically read it as The environment is changing so I feel like you are so I feel like I'm pretty good at that so you can change that as well Yeah, this is not really Yeah, okay So I think the project is not necessarily I think the first one people have described as this whole thing The topic I don't think the project is dystopian. I don't think it's either I think it's just following the kind of the way we're living our lives right now A lot of people have given me very positive comments about it and a lot of people have said this is kind of held And that they never want to be in I Don't really have a kind of opinion on that. I obviously design things which I I think are Interesting, you know, I kind of have this balance between Being excited about my day and also being terrified about it and then somewhere in the middle. There's something interesting to me But I think there are some people in this room here who will probably have some influence in changing the way that augmented reality is going to pan out And the way that the augmented reality is going to be So, you know, we still have this kind of many many choices ahead of us in terms of how the augmented reality is going to look like When I was doing this project, I was always walking a type of you know, what I consider to be Acceptable and on either side there's a lot of power. So I think we have to be quite careful about it but there's many interesting things In the end, they're kind of in the same way that filmmaking became digitized and then democratized We're looking at the same thing with the creation of state So this is really exciting kind of thing. I think I'm sort of running out of time So I'm gonna take some questions, but there's more information on my website So, bring it up Well I was gonna write them on the glasses, but I didn't have time So maybe you can write out new glasses and take them with you I'm hoping to make some more films To continue the project. This is an ongoing independent research project. I'm just kind of secure some funding at the moment But yeah, please keep updated and if you have any questions, I'll take them now. Thank you very much. Hello Hi, how do you think the technical Realization of this It's a good question. I mean a lot of these things are they rely on a massive Reality which rely on some kind of semi-transparent headset, which doesn't exist yet So Yeah, of course, I was thinking about the technical aspects of it as well and I have to be slightly aware of it So for example with the tracking I had the same problems, you know with the computer But I think that there seems to be a lot of investment and a lot of kind of enthusiasm about making this kind of thing a reality and there's obviously it was Great possibilities for people to make a lot of money from this as well, which is a good and a bad thing So for me personally, I'm not so interested in The kind of actual technical details of it. I'm more interested in the architectural consequences and how we actually design this world I think there are a lot of people working on the aspects of it But you can probably see here today as well Maybe you can tell a little bit more about this aspect when two people come together and their reality merges. I think this is an aspect which is totally new. You You don't only get a person known on the basic ways you can start to explore his world Yeah Sorry, yeah, I was thinking that I have a lot of times when I have a friend come over to my house We meet somewhere and we're showing each other videos on YouTube and we're telling each other about books you read or films you saw And a lot of it is about kind of media to surround us So in the same way I did a little study on the kind of concept of domesticity about how you create a home for yourself And one of the interesting things was that in post industrial England, then the living room became a very important room to present yourself to the world So you had your bedroom and your kitchen which was all private, but you had the living room which is your kind of miniaturization of all of your world and your interests And that becomes a kind of a way to express yourself, right? So I was thinking what if you can take a living room out with you and show your living room to people And then what happens if they have a living room as well and you combine those two and you create a new living room which is completely different And all of these things in the living room are talking to each other and you have this like this totally unique space which you can only have with one person And I think this is actually kind of what we do already, you know, like when you meet somebody new then you create a kind of conversation which could only happen between you two And I don't know if I came out to be really boring, but you know So I think this is really just facilitating what we are already doing I mean I think it was Jihani Palazzo who said that we haven't changed what we're doing since we were cavemen, we're still doing the same thing But we just changed how we do them and I think by introducing these things like this then we can find new possibilities to do that as well But yeah, I think it's really nice to sit. I wish I had time to make it Did you ever think about other ways to interact with the interface? Because I always find it strange to see people moving their arms around themselves And I think that part of the success of mobile devices is that it's space-wise, it's a personal space as well So people don't really, they see that you're working on your mobile phone but they don't really know are you writing a message, are you taking pictures or what And I think that as soon as we all start to move our arms around it gets kind of even more awkward You know what, the first time I saw somebody speaking on a hands-free phone It's like a really crazy person, right? Just walking down the street talking to themselves So I do think there is a part of it that when something new comes along then we're initially a bit shocked by it and then we get used to it and it becomes normal So that's a possibility for gestural kind of tracking But yeah, I do agree, maybe gest is not the way, I don't know, maybe augmented reality isn't the way either That's why I kind of pitch it within the larger paradigm of augmented space Because I think everything I've been talking about today can also apply to any of the other technologies in the paradigm It's not just augmented reality, it's all of these other things like control interfaces, wearable computers Even the kind of mobile devices that we're using today, you can still apply these same logic I've written a piece called Two Teeth for Cyborg, which is also the story I linked on my website somewhere And it talks about how we can design architectural physical built spaces effectively for our occupationism now So at the moment we're kind of zoning spaces, like this is for this, this is for this But if you've got a mobile phone, you don't care, you know, you can have a meeting in the coffee shop or you can turn the bus into like a game centre It doesn't matter anymore, so all of the ways we're thinking about architecture is going to be very outdated So this is the kind of sort of guideline to it, so sorry to answer your question I'm not sure about gestures myself, but I think it was just a way of kind of explaining this in a way people can understand in the video Thank you very much Okay, thank you very much then
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The architecture of the contemporary city is no longer simply about the physical space of buildings and landscape, more and more it is about the synthetic spaces created by the digital information that we collect, consume and organize; an immersive interface may become as much part of the world we inhabit as the buildings around us. Augmented (hyper)Reality is an ongoing independent research-by-design project by Keiichi Matsuda, exploring scenarios for our future occupation of the city in the context of emerging technologies and ubiquitous media. These emerging technologies can be grouped under the paradigm of Augmented Space, unified by their ability to overlay physical space with information. It is a paradigm that succeeds Virtual Reality; instead of disembodied occupation of virtual worlds, the physical and virtual are seen together as a contiguous, layered and dynamic reality. Augmented space disrupts the long established dichotomies of public/private and home/work embedded in the city, and calls for new terms to describe our inhabitation of it. The hyper-real mediascapes of the future city are depicted in two award-winning short films, Domestic Robocop and Augmented City 3D, which will be presented alongside production drawings and a work-in-progress first glimpse at the next film in the series. Designed to be provocative and polemical, the films provide a platform to build a debate around, and a counterpoint to the future utopias promoted by many tech companies. They explore the implications for privacy, identity and the construction of space in a dynamic mediascape, with wide-ranging consequences for the practice of everyday life.
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10.5446/20856 (DOI)
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Enfin Hamburg, Wimbledon, Th참ian-K friends God LIAMm andада We are Republica. Thank you. Welcome back. So we're going to be hearing from Gabriela Coleman. She'll be talking about Geek Politics and Anonymous. She's an anthropologist looking at law, digital media, and its role in political activism. And she's here to tell you more. Thank you for the introduction. Thanks for coming out this morning. I'm excited to give this talk today here in Germany. It's really interesting. This morning at my hotel, the person who checked me in said, ah, I've seen you before. I've read your pieces in the Atlantic about anonymous. And I was thinking, wow, that would just never happen in the United States. Germany is really quite unique when it comes to technology. So I'm excited to be here. So as mentioned, I'm a professor of media studies at New York University. I'm an anthropologist who's done a lot of work on free software and anonymous. So I'm just going to jump in in the hopes that we'll have some time for Q&A. Okay, so over the last three years, anonymous has undergone a series of transformations. It was initially called into being primarily to troll and to prank. And then it became a narrowly focused protest movement against the church of Scientology in 2008. In September of 2010, there was a new arm of anonymous, a new operation called Operation Payback that emerged. And this arm of anonymous turned its attention to WikiLeaks in December of 2010, receiving massive media attention. And it received this attention because of the denial of service attacks, the DDoS, that they were launching against PayPal and MasterCard. And it was really interesting because despite the kind of massive media coverage that was happening, and despite the fact that they had already protested against the church of Scientology, commentators really struggled quite a bit to describe their ethics, their actions, their participants in kind of traditional categories. And this difficulty in describing anonymous follows from the fact that anonymous is shrouded in some degree of mystery, some level, but not total of anonymity. It purports to have no leaders, no hierarchy, nor any geographical epicenter. And what is true about anonymous is that it is a name that in theory anyone can take as their own. So for example, people launching the denial of service attacks may not be the same people who write manifestos. And the people kind of organizing the protest against the church of Scientology are not quite the same people engaging in Operation Payback. So there are a lot of kind of mysteries and misconceptions to anonymous. And my purpose today is to clarify some of these misconceptions as well as give you a sense of what is important about their politics. So the talk is divided into three parts. The first part, which is the longest, is the history. I've given a little bit of an introduction just in case some people don't know what anonymous is, but I'll go much deeper. Then there's a section, also a bit meaty, about power and authority and norms within anonymous. And then I'm going to conclude briefly with some thoughts about the limits and strengths to their politics and what we should be asking of anonymous. Alright, so I'm going to dive in. So the roots of anonymous lie in a very popular image board, 4chan, which I bet a lot of people here have been to. And 4chan is a place where people discuss all sorts of things anonymously. But it's also a place where there's a heck of a lot of trolls and trolling. It's certainly not the only place where trolling happens, but it is one place. And trolling on anonymous, or on 4chan, takes a unique form, which is crowdsourced, distributed trolling and hacking. So some trolling is not anonymous, there's individuals, and on 4chan and other places, people kind of contribute in small bits to troll. Trolling on anonymous takes various forms, but sometimes when a target is chosen, lots of unpaid pizzas are ordered to the target's home. If there's servers of an organization that they're targeting, they're DDoS. And of course the most important part is splattering very humiliating personal information all over the internet. And since 2006, possibly earlier, anonymous has been trolling under the name. Now, why troll? Well, if you talk to trolls, they will say that the motivating force and the emotional consequences for the lulls. The lulls is a bastardization and pluralization of laugh out loud. And trolling in the lulls is on a kind of spectrum, right? So some trolling is a little bit creepy, and as someone who works on trolls, and trolling often, or have been the target of light trolling, someone once left a comment about the lulls and trolling on a podcast interview that I did that I think captures well the kind of sentiment and emotional tenor of the lulls. Someone by the name of Lobster wrote, as for Miss Coleman, I appreciate the work she's doing, but I would not want to be locked in a room with her. She has gazed deeply into the abyss. Who knows what horrors have taken root in her mind and why sleeping, waiting to unleash unfathomable nightmares for the lulls. So that's kind of a creepy side of the lulls, but you know, the lulls is on a spectrum. It could also refer to kind of jokes and cute images and cute and furry cats, right? So on 4chan lots of trolling occurs, and in 2008, a legendary wave of trolling was unleashed against the Church of Scientology by Anonymous. And Anonymous kind of decided to troll the Church of Scientology after a video of Tom Cruise was released, and there was a video that was internal to the church. It wasn't meant for public consumption. Someone leaked it. And then Scientology was going to sue online publishers such as Gawker because they weren't taking it down. So let's take a quick look at the video. I'll show about 20 seconds. But if that's what Mr. Cruise has brought to this world, there still remains one more word on the map. Call it Tom Cruise on Tom Cruise Scientologist. I think it's a privilege to call yourself a Scientologist, and it's something that you have to earn. And because Scientologist does, he or she has the ability to create new and better realities and improve conditions. Being Scientologist, you look at someone and you know absolutely that you can help them. So what's interesting about this video, too, is if anyone has seen other kind of video productions by Scientology, they kind of suck. I don't know why this one is kind of high production, even though it's kind of ridiculous. But this video went viral, right? And so Anonymous, after hearing that Scientology was going to go after online publishers in the United States under the Digital Millennium Copyright Act, they engage in a series of raids, which included pizza ordering, faxing, d-dossing, lots of prank calls, and being kind of as offensive as possible. I invited some participants of Anonymous to my class, and they gave a little lecture. It was actually quite good. And one of them described the raids quite accurately and offensively as ultra-coordinated motherfuckery. So consistent with previous actions, Anonymous was just trolling for the sake of the love. But soon after the first wave of trolling, some participants organized a worldwide day of protests that eventually became a more traditional protest movement. What happened? What was this change of heart about? Why did Anonymous veer towards more political territory? Well, it's really kind of fascinating because it was really three user-generated videos that were the actors that catalyzed the debate that kind of led Anonymous somewhat accidentally and chaotically into the realm of political protest. So the first video, and also the most famous, declared war against the Church of Scientology. And I'm going to show not the full thing, but a short clip of it. I like to end with for our own enjoyment because apparently this video was made for the laws. It was just really made for the law. But two things happen afterwards. A critic of the Church by the name of Mark Bunker eventually redubbed wise beard man. He made a video and he's like, look, Anonymous, I see some potential here, but you guys are just two over the top, way out of control. Can you please rein in the trolling? Can you be less offensive? Can you actually engage in some legal political action? And people kind of took his video seriously. And then there was another video. It was a kind of more sincere call to action made by Anonymous. And Anonymous people decided to move forward to organize a day of protest. They left the internet. And on February 10th, 2008, over 6,000 people protested across North America, Europe, Australia, New Zealand. Supposedly one person showed up in Japan. And they were really impressive, actually. Here's a few pictures from the protests. And I went to the ones in New York. And what was really interesting to me was that a good chunk of the protesters lacked what you normally associate with street protests, which is political consciousness, intentionality. Of course, people knew about Scientology because it's kind of part of pop culture, but they really didn't know all that much about it. And in fact, the atmosphere was kind of a lesk. And people were talking in super hypercharged internet jargon about low-cats. They were talking about long cats. There was a lot of kind of images of long cats, mudkips, you know, the sorts of things that came out of the world of Fortan. So soon after this first day of protest, a separation of people occurred. A group of people returned back to the internet from once they came. And a group of people decided to continue on to protest the Church of Scientology. And they still do. One Irish protestor who I met in August condensed the collective mood by saying, I came for the lulls, but I stayed for the outrage. And that sentiment was voiced by many over and over again on forums, on internet relay chat, and so on and so forth. Now, the lulls, you know, he came for the lulls, he stayed for the outrage, but the lulls still had a role to play in this branch of Anonymous and other branches. And I'm going to bracket that for now and return to it because it didn't simply evaporate. And what's interesting about Anonymous is that they have to juggle between kind of more traditional political protests and the lulls, which is far more grotesque and inflammatory and humorous and offensive. And juggling between the two is not always easy. Okay, so starting in September of 2008 until about 2010, the name of Anonymous was used in various capacities. It was used still to troll and it was used to protest the Church of Scientology, although there were a few small operations that were also political, such as one in Iran that happened in 2009 or in support of Iran. In September of 2010, there was a new kind of operation. People called the name of Anonymous, again on 4chan, to call into being Operation Payback. And Anonymous did us the Motion Picture Association of America and eventually other organizations, and they did so because the MPAA had hired an Indian software firm to DDoS the Pirate Bay. And in retaliation and in support of the Pirate Bay, Anonymous kind of showed its face. And what's really interesting about this is that it gives us a window into something that I think is common, not super common, but there are instances of digital privateering. The privateers were hired by European nations to fight in their wars. This was outlawed in the mid-1800s when they had their own navies. And what we see now is a lot of governments and corporations hire programmers to do their dirty work. What's really important to emphasize is that this operation came out of 4chan, like previous ones, but 4chan being anonymous and being that there is no archive is not a great place to coordinate protests. So they moved onto internet relay chat. But it's really important to emphasize that this arm or manifestation of Anonymous was not the same as those protesting the Church of Scientology. Some people crossed over, but really these were now two separate phenomena, two different networks. Okay, December 2010, everyone's talking about WikiLeaks. WikiLeaks releases a small trove of diplomatic cables. And then operations payback shifted its attention to WikiLeaks. And they did so not just to support WikiLeaks, right? They did so at a very particular moment. They did it once PayPal, MasterCard, and Amazon is like, we're not going to serve you anymore. And they kind of bowed to sort of almost unstated political pressure. WikiLeaks had not been found guilty of anything much less charged. So Anonymous really went ballistic at this point. This is a manifesto against MasterCard. And what was really interesting about these DDoS attacks is their sheer size. They were really exceptional in a number of ways. First, they managed to get over 7,000 participants on one internet relay chat channel, which I've been told this is one of the largest numbers of participants, human participants, at least not bots, on an IRC channel. If you know otherwise, please let me know. And what's also interesting is that despite the fact that it was quite chaotic, I had really never seen anything like it. The number of people joining, talking, debating was really astounding. It was truly like a tidal wave. So despite the fact that it was kind of so chaotic, they did manage, however, to kind of control the DDoSing with a notable degree of deliberation and care. They would remind people to stay on target. As Anonymous is famous for, they would write collaboratively on PiratePad to talk about what targets to attack, who not to attack, and the kind of reasoning behind them. So here is an attack plan. And you see something like, do not attack the press ever. So these attacks eventually died down a little bit. And then Anonymous got involved in a kind of unlikely place. And the unlikely place was Tunisia. And they got involved in Tunisia even before the kind of mainstream western media, Al Jazeera is a different story, but the western media was even reporting with any kind of depth or accuracy as to what was going on in Tunisia. And so they started Tunisia on January 2, 2011, once WikiLeaks was blocked from the country. And then they continued to lend a helping hand as street protests just completely enveloped the country. And keeping with tradition, they DDoS the government websites, they DDoS tourist websites, but they also started to engage in different strategies. They created a care packet quite detailed about how people could protect themselves from government surveillance, about where to find good encryption software. And in one of the packets that I read, someone left a little note detailing kind of the very limits of their own cyber activism. This Anon wrote, this is your revolution. You will neither be Twittered nor televised or IRC'd. You must hit the streets. You will lose the fight. Always stay safe once you get arrested. You cannot do anything for yourself or your people. Your government is watching you. So, Tunisia was really quite interesting in a number of ways because it represents some sort of shift within at least one political arm of anonymous. Again, trolling still continued under this name, the protest against the church of Scientology, which has the kind of human rights that I mentioned, but it's still pretty narrow with ongoing. But this really kind of enlarged the scope of what Anonymous was focusing in on and also kind of converged or helped out with an existing political movement. Now during the same period in January, there was other important developments. In the United States, the FBI rated 40 alleged participants, issuing 40 subpoenas, computers were seized. In the UK, five again alleged participants were arrested, released, and I believe actually there are going to be some sort of trial coming up this week. So this was quite significant, but what's interesting was that these arrests and subpoenas did not kind of stop Anonymous. They were not deterred. In fact, they kind of continued to engage in many different operations. So as Tunisia helped to spark the kind of astounding protests in Egypt, Anonymous also turned their attention there. Since that time, they've gotten involved in numerous places, New Zealand, Italy, Wisconsin, in the United States over the law that takes to ban a union's right to kind of collectively bargain, and so on and so forth. Just last week, they engaged in Operation Sony in response to Sony's lawsuit against a hacker who had kind of cracked DRM and the PlayStation 3. So that's just a little bit of a kind of historical arc about what Anonymous is about in terms of the different political arms. And as I wrap this section up, I'd like to turn to the question of the transformation from the LULs, which I talked about into human rights activism. And the story I told just now perhaps could be condensed into nine words in a quote by William Shakespeare, who wrote, Some rise by sin, and some by virtue, fall. There's a way in which Anonymous arose from the heart of what a recent edited collection has called the offensive internet, which refers to blasphemy, defamation, trolling, and really it arose from one of the epicenters of the offensive internet, 4chan. And it has undergone changes as it's become rhizomatic, as it has replicated to have these different arms and nose. It's protested the church of Scientology, it's engaged in offline political fights, its contributions to what will be remembered as one of the kind of really astounding protests of the 21st century. And Egypt really had an impact on the kind of consciousness of many Anons. This was what was written on IRC on the Operation Egypt Channel when Mubarak fell. And also there's a way in which perhaps some Anons will fall, going back to the quote of Shakespeare, given that some have been arrested, right? Some rise by sin, and some by virtue, fall. Well, although the Shakespeare quote would be a really nice way to kind of tie a ribbon around this historical box that I just provided, it actually would not be very accurate. If it was used, it would leave you with a false impression that the lulls, which I don't like to talk about the lulls as sin, but it kind of points to some sort of spirit, it would give you the impression that the lulls no longer matters within Anonymous among those that kind of have engaged with human rights activism. And that's actually not quite the case. The lulls still matters, although it's contained, it's been transformed, but it still shows up in part because this is the culture from which they arose, and how can you be anonymous if you don't have that element anymore. So I'm going to just give you one last story about how the lulls emerged in the context of all this kind of more human rights-oriented activism. So there was an act of trolling that happened soon or during the kind of Egyptian protest, and it happened when Aaron Barr, who's a security researcher, went to the Financial Times, and he said, hey, I've been infiltrating Anonymous, and I'm going to reveal the name of some of the kind of core participants. He worked for the firm HB Gary, a security firm. Well, a swift and brutal response was orchestrated by a small group of hackers within Anonymous. His Twitter account was completely hacked, and the most offensive 140-character statements were spewed from his account. They hacked into HB Gary. They deleted a bunch of backups. They downloaded his email, and then they proceeded to put his email online. They, of course, as many trolls do, splattered images of Aaron Barr kind of all over the internet as well to embarrass him. Okay. And they did this in approximately 48 hours as well. Well, when this happened, the mood of Anonymous was electric and electrified. And for all sorts of reasons. First was the sweet irony that a so-called security researcher who was going to unveil and take off the mask of Anonymous could actually be so easily hacked, right? Second, many people within Anonymous had been expressing concern that the lulls had been depleted during the Middle Eastern protest. The gas tank of the lulls was running on low, and they felt that this had kind of filled it up back to full. Finally, as an extra bonus, it looked like this trolling retaliation actually led to some good in the world. As it turned out, HB Gary was engaging or wanted to engage in the forms of digital privateering that I had raised earlier. Among other things, they had a PowerPoint presentation where they suggested that they could discredit WikiLeaks by handing over false information that when revealed as a forgery would then discredit the organization of WikiLeaks. They also wanted to discredit reporters, most famously Glenn Greenwald, who writes for Salon.com, and they felt like discrediting him would also hurt WikiLeaks. They wrote, again, this was in PowerPoint and specifics, these are established professionals that ultimately most of them, if pushed, will choose professional preservation over cause without the support of people like Glenn WikiLeaks would fold. And so Anonymous's actions revealed the inner workings of an outsourced and privatized agent provocateur proposal, which was never panned out, but it certainly revealed the extent to which private organizations were willing to work for government to engage in this sort of action. Now, when this had happened, I asked Anonymous, how can you reconcile the more traditional activism with these acts of rogue trolishness? And I got a number of answers, which are interesting, so I'll relay them. One of them was, you know, the people who engaged in these acts of hacking and trolling were really a small group of people, and you can't characterize all of an on through one action, because at one time there's 10 or 15 things going on at the same time. And, you know, for better or for worse, that is to some degree true. And then the second kind of answer was that Aaron Barr was putting the lives of people in danger, people were maybe going to go to jail, and there was no kind of legal mechanism by which to address it quickly. So they decided to take an exceptional path due to exceptional circumstances. So I'm not going to kind of moralize it. Right now we can maybe talk about it in the Q&A. The point is really that the love and trolling is still part of the kind of tactical repertoire used by Anonymous within the political arms, and yet is also more contained and predictable than in places like Fort Chan. All right, so now I'm going to move to the next section, which is about authority, power and norms within Anonymous. How is it organized? Where does power lie? Who participates in Anonymous? How can we conceptualize the relationship between the different facets of Anonymous? Well, technically Anonymous erects no formal barriers. It's different from free software projects, for example, where you really have to show your chops before you can become part of the project. And so, you know, anyone, as they say, can join. But obviously not everyone just joins Anonymous, right? It really is more attractive to people who basically spend a heck of a lot of time online. And so there's forms of kind of explicit knowledge, tacit knowledge, ethical sympathies that make Anonymous attractive to some people and not others. A small kind of group of Anonymous are computer hackers, which I know can mean many different things. A computer hacker is not just X, but can mean, you know, a hardware hacker, free software hacker, info security, more transgressive hacking. But basically they're kind of programmers, system administrators, security researchers who identify as such. And there's definitely people in Anonymous like that. I would say a much larger group are, for lack of a better word, geeks. They have some form of kind of digital literacy. They spend a lot of time online. They maybe know how to configure a blog. They've got video editing skills, design skills, and so on and so forth. And then there's people who would not identify as others as either geeks or hackers. Within the arm that protests the Church of Scientology, there's actually a small but kind of fiercely dedicated group of ex-scientologists. And I've talked to them, they're like, yeah, I've had to learn a heck of a lot about this kind of geeky bunker of Internet culture to even understand what the heck is going on, right? So it's kind of bounded to some degree. Now, to understand Anonymous and really to understand so many domains of hacker geek production, of course, Internet Relay Chat is the technical medium through which people form social bonds, through which they collaborate, and it's no different within Anonymous. I just want to point out, and I've just seen this repeated so many times, people represent these as kind of hard to find secret bunkers. Well, in fact, one network even advertises on their main website or provides a link for how to join. They're not in any way closed off. It's just most of the public doesn't know how to use IRC. There's two main networks, AnonNet, which is focused on the protest against the Church of Scientology, and then AnonOp, which is the one that kind of is organizing the protests in support of WikiLeaks, the Middle East protests, and so on and so forth. Obviously, on IRC, what is called an IRC op, an operator, which is not unique to Anonymous, they're on all networks, has more power. They can ban people from the network, and you can get banned for technical reasons or for violating norms. So if you connect and disconnect often, they'll ban you. In the case of AnonOp, they'll ban you if you promote violence, and then they'll ban you because there's also internal drama within the organization as well. It's kind of all groups have. However, to be an op, you don't have to be technically skilled. There's a number of them who I would not consider kind of hackers who've become op, and there's dozens of them, and they certainly carry more authority during debates, but they don't necessarily call the shots within Anonymous. Authority also comes in the form of ethical sensibilities and norms and policy, and here we can see how there's connections between both networks. So participants in both networks are overwhelmingly committed to information freedom. They're against censorship, and as their name suggests, Anonymous, they believe that anonymity is a mechanism by which to secure vibrant political speech. That idea is not their innovation. This is a kind of longstanding principle in many liberal democracies, even though there's a debate as to how much anonymity one should be provided to secure democracy. As I mentioned, in AnonOp, there is a explicit policy not to attack the media, do not attack the media, even forms of media that are seen to be a corrupt arm of state power as in Iran. But what I think is the most interesting norm, and this is true across both networks, you have to look at their anti-leader, anti-celebrity ethic. And what it does is that it modulates or lessens the concentration of power, although it may not fully eliminate it, but it certainly has a role to play in a very important one. And what's really interesting about Anonymous is that this ethic is played out through words as well as through deeds, through action. There's kind of a constant reminder, do not act like a leader, do not seek attention for yourself, do not say who you are. And there's huge conversations about it, but there's also these moments of clarification where a participant might be banned from a network because he or she has called too much attention to herself. I was recently witness to this kind of very act when a participant had been too public about himself to a reporter, and an article was written in a national newspaper in the United States where this guy kind of revealed his name and his age, and people were just kind of aghast at this, especially because this person had not even participated in the DDoS attack, he hadn't even put his life at risk. And so when this kid, I think he was not that old, got online, he was completely chastised, and people were like, why did you do this? You know, you know we're not supposed to do this. And then someone who carries some authority said this, which kind of condensed the collective mood. He said, attempting to use all the work that so many have done for your personal promotion is not something I will tolerate. And he was an operator and banned him. And so it's really interesting because it was a reminder for everyone who was watching, you know, my jaw was dropping, whoa, that you cannot act in a certain way, that to secure your right to participate in anonymous, you really have to embody this anti-leader, anti-celebrity ethic, which is so interesting because nearly everything on the internet, with the exception of anonymous image boards, with the exception of anonymous, is about me, me, me, me, attention, celebrity and so on and so forth. So it really runs against the current of a kind of cultural commitment that is so prevalent on the internet. Now, I just want to kind of re-emphasize that within anonymous, there are certainly those that have more authority, it's those especially who put more work and time, like many domains of geek and hacker action, it is a due accuracy. And this ethic kind of helps to modulate the pooling of power, even if it doesn't fully or always succeed. Sometimes it does and sometimes it does not. And while the kind of anti-celebrity, anti-leader ethic is a bit unique to anonymous, a lot of different domains like free software also worry about the pooling of power and they have mechanisms by which to disperse it. And I just mentioned it because there was an article in Gawker which is online website, I guess all websites are online, but it's a website, an online publisher who claimed to have found the leaders, hacker versus hackers, in anonymous. They were in the secret war room and you know, they actually did find the hackers who were involved in the HB Gary hack. And hacking is powerful, the ability to kind of hack in and delete servers, you know, is not something to be taken lightly, but the article kind of confused the power to hack with the power to lead the entire network and these things can't be collapsed in anonymous. Okay, now I'm going to move towards a conclusion and talk just a little bit about the kind of politics of anonymous. How they're configured, what we should think about them ethically, what are some of the strengths and what are kind of the limits. Okay, so I kind of contextualize anonymous today by focusing in on the political arms. There's still people who use the name to troll. And it came out of the offensive internet, the lulls, and it kind of didn't leave it fully behind, but didn't fully bring it with them as they kind of started to engage in politics. A lot of the politics of anonymous, especially the more recent manifestation, is tactical and it's full of spectacle. They're really, really quite good at spectacle and some theorists, I'm thinking of someone like Steven Duncombe who has written a wonderful book on spectacle called Dream. He argues, you know, spectacle can be quite effective for garnering media attention and also making visible a set of issues that may not be so visible. And anonymous is good at that, but spectacle has its limits. Basically, if you overuse it, people won't pay attention to it anymore. There's a kind of fatigue built into it. And I think there's a way in which this current arm of anonymous in using DDoS quite a bit has also deflated the power of spectacle to some degree. I think it's also important to interrogate the use of DDoS as a political weapon, that is, which brings into being some form of spectacle. There's a lot of questions to be asked and it catalyzed a huge debate. Is it a form of direct action? Is it legitimate protest? Is it a form of civil disobedience? A lot of internet enthusiasts and hackers really differed in their view. So, for example, Richard Stallman, first of all, reminded the world that it wasn't hacking to DDoS because you're not hacking into anything. You're just overwhelming a server with requests. But he did favorably, he portrayed them favorably as a mass demo against control. I was actually kind of surprised, but he wrote this editorial for The Guardian, a famous hacker to this part of the world at the CCC Congress, described DDoSing as juvenile, infantile, and kind of suggested to anonymous to come talk to him so that they can mature and engage in more constructive action. And I'm personally not going to come down on a position, I do think it has a role to play, but if we're going to assess it, there's two things we should do. One of which is contextualize it within the broader milieu of DDoSing, and I'll talk about that in a second, and also talk about predecessors, other people, other groups who have used this technique. And so two different political organizations who have used DDoS in the past have been the Anonymous Digital Coalition and the Electronic Disturbance Theater. And like Anonymous, they all conceptualize what they do as conscientious action. They see it as law breaking that is legitimate insofar as they're making a kind of statement through this action. Now the big difference is that Anonymous Digital Coalition as well as Electronic Disturbance Theater were quite small, and while you can kind of participate in them, they weren't configured in such a way to get 7,000 people to participate at once. And once you have that amount of people, you both have power to be able to kind of take down something like Mastercard, but you also have a lot of unpredictability and a lot of risk. You can't control those 7,000 people, and civil disobedience traditionally has been tightly controlled. It's not participatory. So does the participatory element of Anonymous actually go against the grain of thinking about DDoS as civil disobedience? The second element to consider, of course, is that DDoS has been used far more by the powerful to silence the weak than the other way around. So there was an important Berkman Center for the Study of Internet and Society report which showed just how extensive governments deploy DDoS to silence small human rights organizations. And so by using DDoS, do we then just proliferate a tactic? Or alternatively, if we make it uber illegal, and it is pretty illegal already in certain countries like the United States and the UK, then do we just leave DDoS to those who can evade the law and with the power and resources to do it, such as corporations and government? So these are kind of certain questions that I think are really important to address as we assess this tactic as civil disobedience. But it's important to remember that Anonymous has shown already that it's not only bound to kind of tactical forms of politics that engage in spectacle, but they've also engaged in more strategic long-term organization. The protests against the Church of Scientology are ongoing. They happen every month in many cities across Europe, the United States. I truly do think that they had an important role to play in allowing critics of the Church to be far more visible and less anonymous, ironically. And I would include myself insofar as I used to work, or I still do, on geek and hacker protests against the Church of Scientology, but I was never very public about it because I didn't want to get embroiled in a lawsuit and post-anonymous. I was like, well, they've got their hands tied. Let me just be far more public. So they've had a really important role. The arm of Anonymous that is engaged in the Middle East protests has also turned to more strategic action by creating technology to evade censorship and kind of becoming a little bit more organized, not in the hierarchical sense, but getting to know each other and learning what they can and cannot do. So they move between the tactical and the strategic. So just to wrap up, even the different political arms of Anonymous use different tactics, but I think there's a few things we can say more generally about them. Since the winter of 2008, due to providing non-traditional mechanisms of action and ones that really made use of the full capabilities of what the Internet has to offer, it has acted as a political gateway for many geeks and people who care about Internet issues to take action. For some, they contribute to Anonymous by writing manifestos. They just love to write manifestos. There's a lot of designers who make the artwork. There's a lot of what they call propaganda as well, which is really astounding in the form of videos and art. It provides flexible and discreet micro-protest possibilities that aren't otherwise there in a way that allows individuals to renounce their individuality, but also be part of something greater. You don't have to fill out a form. You don't have to send money in. You don't even have to give your name, but you're probably going to engage in a form of politics that also has a lot of lulls and a lot of laughs, for better or for worse. The decision to engage in political action has to happen through some sort of concrete path, some sort of set of events and influence, and I think Anonymous has been important because it's definitely been that path for a large number of people. So I'll leave it at that. Thank you very much, and I'll just take questions when people are ready. Thank you, Gabriela. That was a fantastic talk. If you have questions, please come to the front. We have time to take a few. I know you're just here for the lulls, but stay for some insight. Hi, my name is Saru Sparvar. Thank you very much for your talk. You mentioned that there were some people from Anonymous who are being charged with crimes in the U.S. and the U.K. And I'm curious if those people who have been charged with hacking or d-dossing or whatever, did they get caught because they didn't use proper encryption, or did they get caught because they actually have some kind of authority within, I know you talked about how there isn't an authority, but obviously there are some people that have a little bit more influence than others. That's a good question. So in the United States, no one's been charged yet. It was subpoenas just to get information. In my sense, the FBI is definitely on IRC, right? Whether you hang out with Anonymous or other troll groups, part of the fun of being online is when they're kind of making fun of the FBI. In some way, the FBI knows who the infrastructural operators are, right? It doesn't take a genius to find that out. What's really fascinating about that, in fact, is I know one operator, in fact, who doesn't even engage in any of the politics. I'm providing a platform, and I can't get in trouble for that, right? So the question is, can a provider of the platform be considered someone who is contributing? I do think that Anonymous, especially at the beginning, wasn't totally using full encryption to hide themselves, and definitely post these attacks. There's a little bit more of an awareness. Don't keep blogs, maybe use encryption, and make it a personal choice. For some, they're like, well, we're being conscientious about this, and it's okay to be arrested, and for others, it's not. So a little bit of both. Hi, Markus. I have a question. There is this concept of positive and negative freedom, where the positive freedom is that we ensure everybody to have his personal freedom and can do whatever he wants, and where the negative freedom is that we have, in the modern state, the laws, which ensure the ecosystem where I can live free. But it may put down the personal freedom of others. And you mentioned that there's some kind of self-control within Anonymous, if some people... But there is no constitutional law, no representative democracy. So what do you think are the impacts on this positive-negative-freedom thing? Yeah, that's a great question, because if... And I've studied Debian, the free software project, quite a bit, and they have both constitutional, like, law, as well as the more informal modes of operating freedom, right? And early on in Debian, they only had the informal modes of organizing freedom, and then it became quite formalized in pretty dramatic ways. And Anonymous is fascinating because they're kind of in its informal, charismatic stage, where obviously they're too sort of like Wikipedia, like Debian, they're just in a stage where they're not going to formalize. But the very, very, very ideology and purpose of Anonymous is such to prevent structure. Whereas with Debian, that was not the case. They may not love it, and a lot of geeks and hackers are against bureaucracy and red tape, and yet they've had to formalize a little bit. So with Anonymous, it'll be fascinating to see whether they formalize a little bit more, or their very kind of ideological commitment prevents that type of more explicit legal rulemaking that you're talking about. Do you have one more question? Great speech. Thank you. When younger people are involved, often there is a generational change. So you have one group forming, next generation comes up, doesn't want to mix with a generation before new group forms. How do you see Anonymous in the midterm and the long term? Wait, can you repeat the last part? How do you see Anonymous in the long term? Yeah, that's a really good question because there is a way, I try to signal this in my talk, because on the one hand, Anonymous is open to all, and it uses some forms of language, free speech, that has kind of wide cultural currency, people can identify, and yet it comes out of this extremely kind of geeky esoteric bunker of the internet. I mean, I can talk in sentences that are just filled with jargon from Encyclopedia Dramatica, and you would think that I'm talking in Chinese, I'm talking in English, right? And that's kind of, to some degree, generational. And then the question is how do you then ensure social reproduction over time? Again, I find comparing to free software very interesting, because free software is, I consider, intergenerational, there's like the old Unix guys with big beards, and then the young people, and what joins them is the Unix architecture, which has been around since 1969, and it's a shared lingua franca, shared language by which to connect the generations. And I think with a formation like Anonymous, you have that a little bit less, right? And so that you may fall in the trap of it losing its power or force over time. But one thing that is pretty amazing about the world from which it emerged is that the cultural traditions of the lulls and trolling is actually like an oral culture, and they catalog everything. This is where Encyclopedia Dramatica is so important, because then through things like their lore, their history, their exploits, that may be one way to have links formed from the past, present, and future. But time will tell. Hello. I've got a small footnote to your talk. First of all, the head package that you're referring to, as far as I know, has been provided by some well-known groups on the Internet, like telecomics and some French groups. So I think it was not quite to be attributed to Anonymous. And my question is, you were referring to celebrities inside Anonymous. Are you going to be banned? Okay. So there's some anonymous developers that also participate in telecomics, and one of them has kind of conceptualized quite nicely telecomics and anonymous as Ying and Yang. And what's interesting too about Anonymous is there's really talented free software developers who are part of Anonymous. And my understanding is that they did take definitely some of the work from telecomics, but also did a lot of their own configuration and repackaging. And I actually think it's an important footnote, because I think really taking a look at the relationship between various different nodes of kind of political intervention, such as telecomics and anonymous, is necessary. Me. Yeah. So there have been... I started working on Anonymous a long time ago through an odd set of reasons, and people ask me all the time, are you anonymous or are you non-anonymous? Well, as an anthropologist, the kind of ruling methodology is called participant observation, which is a bit of an oxymoron. But, you know, you get to know people really well. You help out where you can, but you don't fully get involved. So I don't engage in d-dossing. I don't wear my mask. And I think that they realize that I can't be anonymous. At the same time, there is a thread in one of the forums, Why We Protest, which is for the protest against the church of Scientology, where someone's like she's acting too much of a rock star in relationship to her work and anonymous. And then people came into my defense, know she does good work, she actually understands what we do, and she's not just portraying us as basement dwellers who are, you know, bent on raising internet hell. But it's definitely something I think about, and if I had more time, I would also talk about the few people who are able to be visible within anonymous, one of which does so without any problem, the other person does so with a lot of problems, but they tolerate it because he does so much work for the organization. It's not an organization, but for anonymous. But I've definitely been in a pickle before, and I'm sure that will continue to be an issue as I move forward with research. I think that's it we have for time. But thank you very much. Thank you. Okay. Great. So we're just going to have a few minutes break before our next speaker, and I wanted to give a shout out to the talented Annalena who's been visually recording the talks. I think afterwards they're going to be online, and you can also come down and have a closer look and admire the wonderful art.
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Over the last three years, Anonymous went from Internet pranking and trolling to a narrowly focused protest movement against the Church of Scientology to one that has now emerged in more general registers to protest censorship, attracting many geeks and hackers to its ranks, some who have entered the arena of politics for the first time. In this talk I will examine the transformations and tactics of the digitally-based protest movement—Anonymous— to examine various political and ethical facets of their operations, including their rhizomatic social organization, the ways they enact an ethics around their denial of service attacks, the spectacle they generate, and the ways in which they are rooted in and parlay liberal commitments such as anonymity and free speech.
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10.5446/20860 (DOI)
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Patrick Meyer is not a German as you might suggest with a name. He's the director of crisis mapping at Ushahidi and he's the co-founder of the international network of crisis mappers and he's going to talk about the importance of maps in today's world and also he's going to talk about a new initiative, the Stand-by Volunteer Task Force. So please welcome Patrick Meyer. Thanks. Cheers. Hello. This is working great. Hello everyone. It's really a pleasure to be here. This is such a phenomenal conference. I was following the Twitter feed and you're tweeting like a hundred tweets a minute. It's incredible. Really active. So what I'm going to do with the next sort of half an hour or so is talk about maps, but not just any kind of maps. I'm particularly interested in the kinds of maps that combine crowds and clouds to drive social change. But I want to start in the days before the cloud with this story. And in particular 1994, more than 800,000 people were murdered in a very, very short period of time in Rwanda. And the radio as we all know, had you know, played a pivotal role in broadcasting that kind of hate speech, the dehumanization that happened, the demonizing that happened at the time. And the Romeo Dallert, who was there, was told to basically look the other way. Right? He had sent a fax to the UN headquarters in New York saying, listen, something is happening here. People are starting to collect weapons. It's looking really bad. I need to intervene. He got a fax back and was told, no, do not intervene. Do not get involved. We don't have the mandate to actually enforce a peace. Now it turns out that Romeo Dallert actually disobeyed direct military orders and was able to save about 30,000 people in the process. But let's imagine just for a second that Romeo Dallert had been on Twitter. What if he had been on Twitter? What if he had 10, 20, 100,000 followers? What if the officers under his command had been on Twitter and were using YouTube and Facebook and what have you to share what was happening? Maybe just maybe history would have panned out a little differently. Moving along to 2008, during the post-election of violence in Kenya, more than half a million people got forcibly displaced and some 1,200 people were killed. But I remember I was visiting my parents. I grew up in Kenya and I was visiting my parents at the time and I remember the newspaper headlines. Kenya is not burning. Maybe the government, the Kenyan government, was doing all it could to downplay the expense of the violence that was happening. And of course the mainstream media can't be everywhere at the same time. There are only a few journalists and they're not going to be able to document all the human rights abuses that were taking place. So this, however, was the information ecosystem alive today as well, very different from 1994. That's only in terms of the peer-to-peer communication technologies, but they're free and they're interconnected, meaning I can send out a tweet. That tweet can be reposted on my Facebook wall right away and also posted on my LinkedIn profile. So there's this kind of instantaneous, meshed, horizontal communication that's possible in real time and not just in terms of text-based information, right? You've also been able to share YouTube footage and pictures straight from Twitter and what have you. So that interconnected feature of this real ecosystem that I think is quite different from what we've seen before and I think that lends itself to perhaps unpredictable results. What was the world's response in Kenya? Well, I actually want to leave the world aside for a second because when we talk about the world, we often really mean the government, the official organizations, the established institutions that have their own political motives and their own agendas. So what did normal, everyday kind of people do when the violence started to flare up in Kenya? Well, some friends of mine, some Kenyan friends of mine, set up the first version, the first map with the Ushahidi platform. And this was really nothing to, I think, revolutionary in many ways because Google Maps had been around for a good three years already and you can see here on the lower side of the screen, what we also did was set up an SMS number, an SMS short code that allowed anybody to text that number for free in Kenya to report the human rights abuses that they were witnessing. And SMS had been around for years, right? I think the novelty here was the integration, again, of this kind of ecosystem, which provides perhaps a more powerful way to share information. And indeed, what this allowed people to do and what allowed us to do at Ushahidi was in a way to circumvent the Kenyan government, right? And to also overcome the limited capacity that mainstream media has because those journalists could not be in 100 cities at the same time. So we applied this idea of crowdsourcing that we're all familiar with, I think, from Wikipedia to the reporting of crisis information. And this allowed people to document human rights abuses that would otherwise have gone completely undocumented by the government, by human rights organizations, and by other parties. And that's, I think, really a different story than what we've seen before. So what we've done with Ushahidi since basically established an NGO, but not any kind of NGO. We're an African non-profit technology company. So slight hybrids. We're not a Silicon Valley, you know, Western-based software company, and we're not for-profit. We're non-profit. Ushahidi means witness in Swahili. And what we do is we develop free and open-source software that allows people to collaborate in creating live maps of their environment. So real-time collaborative type mapping. And we try and do this using multiple technologies, not just because of what we saw in Kenya, but also what we've seen more and more around the world, and which Sam just before from witness was explaining. We see scenes like this. This is already two years old from Tehran during the election protests in Iran. And you see the probability now is increasing that somebody somewhere is going to be able to capture an event, either with a text message or tweet, an email, YouTube footage, or Flickr. But what we're also seeing now is that more and more people, groups, masses, crowds, are starting to document historical events that are happening in time and space, and starting to upload this information on the cloud. So what we want to do with Ushahidi is continue integrating these technologies, because once these individuals go ahead and upload to their YouTube account or what have you, it sort of gets a little distributed. It gets a little dispersed, just like these particles going into the cloud. We want to be able to bring all that evidence right back to one place. And we want to use a geographical map, because we think that's one of the most intuitive ways to represent real-time information across different media. So we've integrated SMS as part of the Ushahidi platform. We've also integrated email and also Twitter, Egyptian colleagues of ours in Cairo integrated Facebook, which means you can post something on a wall and that goes into the Ushahidi back end and then you can map it. There's a geographic component. We also have a number of different smartphone apps for different smartphones like the Android and the iPhone and so on. And other people have been using YouTube and Flickr because they've been uploading pictures on these maps as well as video footage. Sometimes in near real-time and they use Skype to collaborate all around the world to create these maps. Moving along, 2010 was a rather disastrous year in many respects. It started very early on in January 12th with a really devastating earthquake that struck Haiti, causing more than 200,000 people to lose their lives. So in this case, what did we do? It was our response, just everyday average kind of people. Well, as soon as I learned about the earthquake on CNN a couple hours after it took place, I called David Kobia, who's our technology lead at Ushahidi and said, David, something bad has just happened. Can you set up this map while I start looking for information to map on the Ushahidi map? And within an hour, we were starting to map. And the first sources of information that I had found were on Twitter. I'd found about half a dozen Twitter users in Port au Prince who were tweeting live about what was happening and what the impact was. And we continued monitoring these individuals. Some 10 days later, the head of FEMA. Now FEMA is the official US Federal Emergency Management Agency, the official US body that's responsible for disaster response. Craig Fugate in a public tweet noted that this map that we just launched was the most comprehensive and up-to-date map available to the entire humanitarian community. And I want to pause there a bit because that's something different, I think, that's happening here in the humanitarian space. Because it was not FEMA that had started this map, let alone was managing the map and adding information to the map, nor was it the United Nations, the World Food Program, UNHCR, what have you. What was it really any official humanitarian organization? The map started in my living room in a dorm at Tufts University in Boston while it was snowing outside. And a couple days after my colleagues, Adush Shahidi and I, started mapping, we couldn't keep up anymore. Because this information ecosystem went into overdrive, user-generated content exploded, the mainstream media was going 24-7. So what I decided to do was just email a bunch of my friends in my grad school program and said, listen, I don't have a plan or anything, but I'm just trying to map Haiti. And if you're around, I could really use your help. So that evening, these first friends showed up and we just started mapping. By the end of that week, 100 people had showed up at one point in time in my living room just to get trained and then go back to the library or back to their place or Starbucks to continue mapping. And then a week after that, a couple hundred other volunteers showed up at the university in London, at LLC, in Geneva at the graduates institute there in Toronto, in Washington, D.C. These students and non-students, other volunteers, just got together and created their own little situation rooms to help our efforts in Haiti. And we were able to do this because of this ecosystem. And actually, if you look at this picture, the guy on the left, the French guy who was actually listening to radio, French radio, and when he heard of new events or new updates, he would go ahead and map it. So we were drawing from social media, mainstream media, official reports from the UN and humanitarian organizations, television as well as radio. And we were curating all that content in near real time and mapping it, just putting it on a map. And this is really, in a way, what it looked like at one point. You can see how densely populated this map was. If you look at this number 22, that's actually the number of reports within that particular area. So if you were to zoom in further, you'd see 22 additional individual reports within that particular street corner that had been mapped and geo-referenced. So this really was a map like no other. This was no ordinary map. We'd never seen anything like this. The humanitarian community hadn't seen anything like this. We'd never done anything quite like this. But this map changed. It never looked the same for more than 10 minutes. Every 10 to 15 minutes, new information, new data would be curated and geo-referenced. It was a living thing. It was definitely not static. So imagine for just a second, if we'd had something like this for Rwanda or other conflicts or other disasters in the past 10, 20, 100 years. I think it's a slightly different world. And there's another reason why this is somewhat different. It's because by doing this, and again, I don't want to suggest we had any plan. This was an emotional reaction. Saw the news on the TV. I had actually some very close friends of mine in Port-au-Prince. I didn't know whether they were dead or alive, and I just felt I needed to do something. So there was no plan. I had never done anything like this before. And it turns out that a number of first responders, like the Marine Corps and the US Coast Guard, actually used our maps. And according to the Marine Corps, they said they used our maps every day and that this helped save hundreds of lives. They were literally taking text messages or emails or what have you from the map and sending out the choppers to go evacuate people. So this was a very, very different way of doing disaster response when you think that you had a bunch of amateur volunteer students in Snowy Boston using free and open source software made in Africa to save hundreds of lives thousands of miles away in Haiti. It's completely crazy in many ways. But the real story and the reason any of this was possible really starts with this picture. While a number of the cell phone towers in Haiti and Port-au-Prince were affected, many of the critical ones were repaired very quickly within a matter of just a few days. So we knew, like in Kenya, that the answer was not going to necessarily be email or internet access, right? But most or many people have access to a cell phone in Haiti. So SMS was going to have to be the answer if we were going to do something that was going to have some impact. And again, while we had that thought, we had no idea whether it was going to work or not. And a day or so after the earthquake, a good friend of mine, Josh Nesbitt, who works for a group called Medic Mobile, sent out a tweet and just said, okay, I'm looking for an SMS gateway to help out with this Haiti-Ushahiti map. What's remarkable with this tweet and the reason that I'm sharing it with you is within 20 minutes, somebody in Cameroon saw his tweet and tweeted back and told him, listen, I actually know somebody who works for the telecommunications company, the biggest telecommunications company in Port-au-Prince, a company called DigiCell. Within that hour, Josh, who was in Washington, D.C. at the time, was on the phone with a contact at DigiCell in Port-au-Prince. And by the time he hung up the phone, after half an hour, they had agreed to give us a short code. And the short code was 4636. And the entire SMS operation that took place with this short code became known as Mission 4636, which was spearheaded by another good friend of mine, Robert Monroe. Robert is a computational linguist at Stanford University. And he got started right away. As soon as Josh let him know about the short code being secured, what we did at Ushahiti, we started integrating the short code with the Ushahiti platform. But he was smart, well, maybe we weren't thinking, and said, wait, listen, guys, the vast majority of text messages, if this is even going to work, are going to be in Haitian Creole. They're not going to be in English. There's some small fraction might even be in French. But 99% of them are going to be in Haitian Creole. None of us speak a word of Haitian Creole. So what he did immediately was get on Facebook, because many groups within the Haitian diaspora, the very large diaspora in the US and Canada, started organizing their efforts on Facebook. So he went from Facebook group to Facebook group to Facebook group and said, listen, this is what we're trying to do. We may be getting a flood of text messages, which we're going to need to translate. Within a few days, as we went live with the short code, and as we started broadcasting this number on local radio stations in Port-au-Prince, Robert was able to recruit 1200 volunteers from 49 different countries. And this is the location of their ISP addresses. When they logged on to our system to translate these text messages, this is basically their location. It's pretty astounding to think what they did. They actually translated more than 80,000 text messages for free, completely on their own, and the average turnaround time for a text message was 10 minutes. So literally, as soon as a text message left a mobile phone in Port-au-Prince, 10 minutes later, we had it in the Ushui-Di platform in English. And often it was geo-reference, because a lot of what these Haitian diaspora volunteers did was also help us find a location, because they obviously know their country a lot better than we do. And this is just a word-all graphic of the first two weeks of text messages that we received and that were translated. And I think for me, what's really telling is that I think the second most used word is please. And you can imagine, this is an incredibly traumatized population. Most of them have lost at least one person they knew, if not an entire family. And they're still saying please. I think that's a huge testament to our humanity. And that's not all. They're not just dots. They're real people, just like you and I. They're people that have their jobs, that go to conferences, that go to school, that have their own worries and concerns and loved ones and so on. But they still took the time to help people who they would never meet thousands of miles away by just translating, by offering their time to translate about 10 novels worth of text messages. I'll let all of them know you applauded. Thank you. 2011 is not much quieter, as you know. Devastating earthquake in Japan with the tsunami that resulted caused a lot of havoc and destruction. But within a few hours, some friends of ours in Tokyo decided to launch a live map of Japan. They had seen what had happened in Haiti. So this kind of learning that's starting to take place now. And started mapping. Again, not necessarily with a plan per se, but they saw what happened in Haiti. Like, okay, we might as well try this out. And now this is a very different context than Haiti. Here you have a society that's incredibly connected, incredibly technology savvy, very media rich. So the vast majority of information that ended up being and still is being mapped comes from Twitter, from people monitoring the Twitter feed. And again, just to drive the point home, the group behind this initiative was not the Japanese emergency management national, what have you, right? It was not the pros, not the people who are paid to do this. It's a bunch of volunteers that got together, eventually found a space in downtown Tokyo to do this in one room. In fact, I just heard a couple days ago, I was in touch with the team, that one of their volunteers is 13 years old. This is a 13-year-old Japanese kid who's called a super coder. Apparently he's like a massive hacker who went in and started to help with the software development as well. So it's incredible the kinds of people that come together that otherwise would not come together in these types of crises and disasters. And again, you can see just how densely populated. We mapped about 3,000 individual reports in Haiti throughout a two-month period. They mapped 3,000 in one week. They've mapped more than 10,000 reports now. And because they have the most comprehensive live up-to-date map in Japan, the government, as well as foreign embassies, are actually, Western embassies, are using this map to inform what's happening, to get more information, to get more situational awareness about what's happening in Japan. There's another completely different type of crisis now, as you know, also unfolding, unfortunately still, in Libya. And unlike Haiti, what we saw in Libya was somewhat different in terms of the response, because immediately the UN, which was an organization that was a little skeptical, to be honest, about crowdsourcing and after Haiti, about crowdsourcing, about social media. For them, it's just a new territory. So they're not quite sure what to make of it. But a year later, on the official UN Twitter feed, they said, hey, look, this is how social media can actually help. And what happened was on March 1st this year, the head of the Information Management Unit at OCHA, so OCHA is the UN Office for the Coordination of Humanitarian Affairs. So the main UN body that's in charge of coordinating humanitarian response across UN agencies and also across the humanitarian community. The head of their Information Management Team emailed us and said, okay, listen, situation is pretty bad. We know that, but we really don't know exactly what's happening in Libya. For us, it's just a black box. Why? Well, because the United Nations has not had any personnel that's been stationed in Libya. They don't have any Information Management Officers in Tripoli or Benghazi or what have you. And they don't want to rely on government propaganda. And there are no alternative official sources of information that are independent. But they knew, seeing what happened in Haiti and after, that there was probably a lot of information coming out of the social media space, namely on Twitter, on Facebook, on YouTube, and on Faker. So they asked us, can you create a live map? And we said, we need to start planning our humanitarian relief operations yesterday. We need to start allocating funding and resources and finding what our strategy is going to be. Where should we be expecting the refugee flows and so on? So within a couple hours, we started mapping and creating this live map. And even the executive director of the World Food Program, Josette Sheeran, mentioned this public tweet. And they can actually use this crowd-sourced social media map to allocate food supplies along the Egyptian and Tunisian corridors. So a really different world in many respects. And again, seeing how densely populated it very quickly got. And the UN OCHA, but the World Food Program, UNHCR, the Red Cross, and a number of other humanitarian organizations were using this visualization to basically analyze the situation. And I'm going to ask a familiar question. Who was behind this initiative? You know it was not the UN. You know it was not FEMA. It was a group called the Standby Volunteer Task Force. Now this is a network of individuals that a few friends of mine and I launched just a few months ago, because we saw what happened in Haiti. People just came out of nowhere to help out. I mean, you saw those 49 different countries. And we saw that after Haiti when the earthquake in Chile happened, people came back. Some of the same volunteers came back and wanted to help again. And new volunteers came back, because this time it was Chile, it was South America. Maybe they were from South America, and they wanted to help. And then we saw during the massive floods in Pakistan, some of the same volunteers would help out in Haiti and in Chile come back with new volunteers from Southeast Asia coming on board to help out. And the same thing happened with the Russian fires and so on and so forth. So we figured, wow, there's really something special here, something that maybe we haven't really seen before. Why don't we just give this network of people a name? Let's give them the brand. Let's give them a face. So we decided to launch the Standby Volunteer Task Force. And we now have more than 500 volunteers in more than 50 different countries around the world who have become trained and skilled in doing live crisis mapping operations. That's something that, again, we haven't seen. And it was this team that we activated within an hour or two after the request from OCHA to basically create a live map of Libya. And I want to just say a few words about the word volunteer, because I think the word volunteer tends to come with a negative connotation sometimes. You know, you're a volunteer, you're amateurish, and you're not really reliable, you're a skateboarder or something, and that kind of like prejudice that happens. These volunteers are self-selected. They're the ones who decide to join because they want to, because they feel they want to make a difference, because it means something to them. And many of these volunteers are skilled professionals. So I'll give you just a few examples just in terms of who is part of this task force. We have one person from Iceland who's had 16 years of experience in leading search and rescue teams around the world. We have another chap who toured with a Sarmanan Garfunkel in the 1980s, and he's helping out. We have an undergraduate student in Toronto who is a theater student who spends her evenings in the weekends helping out in mapping Libya. There's even a doctor in Samoa, and there's an emergency airside manager at Heathrow International Airport who basically after the last planes take off from Heathrow Airport around midnight, he jumps in Skype and he jumps on the crisis map just to help out. The oldest volunteer that recently joined is 85 years old, which proves that it's never too late to join and try and make a difference in the world just from your own laptop. So I bet you're wondering, how can you become a crisis mapper? Right? Well, I have an answer for you. Simply send us an email at joinstandbytaskforce.com, and there's really no obligation. That's really not our style. What our goal is is to train people in how to do live crisis mapping operations. We've got modular team structures, we've got workflows, it's all pretty self-explanatory, we've got a dedicated website, a social networking group to coordinate, and we're on Skype as well. So there's no obligation. If you just want to get trained on how to do live crisis mapping, simply drop us a note and just to let you know that the UN, Ocha, and Geneva and other groups are also coming to us and joining the task force because they want to get trained in how to do this. So I'd love to have you on the team. Okay, we've talked about disastrous crises and so on, but of course we can't ignore the fact that there have been a few revolutions in the Arab world over the past few months. We saw that the protests in Cairo and across Egypt, Alexandria and other cities, brought millions of people to the streets. And as one Egyptian activist noted that she said, you know, we use Facebook to schedule our protests and we use Twitter to coordinate them and then we use YouTube to tell the world about it. So there's, as you know, full well, more and more of a reflex around the world with respect to getting on Twitter, getting on these social media tools and sharing information and coordinating. But there's another reflex that we've seen starting to surface over the past couple of years and that's the mapping. So as soon as the internet was back online in Egypt, an Egyptian group set up an Innooshahiri map and if your eyes are better than mine, you'll see the URL, the domain name is Ford slash CR. CR stands for Civil Resistance. This group had every intention to use this map not only to coordinate their efforts and the protests, but also to map the crackdown by the Mubarak regime, the violence that the thugs were actually committing. And one important feature of the Innooshahiri platform that sort of helps with that and it's all in Arabic but you'll have to trust me on this, what you can do is you can subscribe to alerts. So you can go on that map and you can point the cursor to maybe wherever your neighborhood is, define the radius of area of interest and as soon as something gets mapped within that particular surface area, you get an automated email and or an automated text message. This idea of providing you with real time situational awareness about what's happening when it's happening and importantly in real space, meaning exactly where that particular event is happening. And that helps to close the feedback loop. It allows you to perhaps have more information and hopefully make more informed decisions about what to do when you get that information. Ironically though, I think that one of the most important pieces of information that was circulated in the lead up to the revolution in Egypt was on a 26 page PDF document. There's not thousands of copies of this document were circulated in both Cairo and Alexandria. And this goes back to the basics. This was simply a very, very well written strategy guide on how to coordinate and strategize civil resistance down to the tactical level. It's incredibly well written. People who wrote this, I don't know who, knew exactly what they were talking about. What's equally interesting is that a lot of this guide talked about movement, about how to move around in the streets, how to recruit. You start in a small alleyways, right? Because you build more momentum. You build more energy. And then you flood into the avenues altogether. You don't just show up in Tahir Square for the heck of it. There's really in a way of science behind civil resistance. It's purposeful. It's deliberate. It's planned. It's calculated. And this civil resistance in Egypt was one of the most disciplined, well carried out and well executed civil resistance movements that I've seen in a long time. And they went so far as to including screenshots from Google Earth of downtown Cairo in this 26 page guide, outlining where to move, that maybe these areas you might get ambushed and so on, and just trying to provide some informative guide on where to go and where not to go. Now this was all in a PDF document. So this is all static. But there's no reason this needs to be static, right? And this is a great quote from a US chief security officer in the US who's incredibly pissed off about these real time maps. He's just incredibly fed up. He's annoyed. He's had it. He's saying basically for crying out loud, these real time maps are basically as good as having your own helicopter. And now these bloody activists own these helicopters. And that's not okay. He's really annoyed. And you see the hyphen there. And he goes far saying, you know, these real time maps are maybe even better than a helicopter if you can distract the crew. And what he means by that and what he's worried about and rightfully so, what if some activists set up a map and start mapping that they are headed to the palace, so the presidential palace would have you. When in fact they're legging it the other way and headed to the parliament, right? You can start doing deception with this kind of civil resistance. So we thought to ourselves, that's pretty neat. How can we help out in this kind of helicopter building? And we figured we don't want to just give activists any kind of helicopter. We want to give activists the best kind of helicopter that they can possibly use, right? Let's really piss people off. So we started thinking and with the help of others, this was not just our idea. We put two and two together and I think you're all familiar perhaps with Foursquare or Goala and even Facebook now. You have this check-ins idea, right? So with Foursquare it's all very entertaining and it's fun because you can network, you can connect, you can check-in to Berlin and become the mayor of Berlin and have a badge and 10 points and you find out that 17 of your friends are in the pub next door or what have you. So it's really neat to connect people and it's fun, it's engaging. We figured why can't we take this basic idea and apply it to other purposes. So we just launched Ushahidi check-ins. We call it CI for short for check-ins at South by Southwest just recently. So it's still very, very early in terms of the development of Ushahidi CI but this is what it sort of looks like and I actually set one up last night for this conference. So this is what it looks like. If you get on your iPhone and download the app, you can go to Republica and then what I did last night, let's see if this works, just a quick instant message, right? Going, hey, I'm Republica, I'm really excited and then you'll see that within 30, 20, 10 seconds it's posted there. And so what we're doing with this kind of check-ins idea is we're looking at this idea of instant messaging but applied to mapping. So check-ins is like instant mapping. It's like sort of one-click mapping, letting the world or whoever you want to know know about where you are. And we also figured, you know, why should there only be one Foursquare company or one Goa'la company? These companies are for profit, nothing wrong with that but it's proprietary software. So you can't have really your own Foursquare. So the check-ins that we're developing and that's already available is free and open source. There's no reason why you can't have your own Foursquare company. I mean, I know it's really disruptive but that's what we do. So you can set up your own check-in system for Boy Scouts or your company or, you know, you name it. There's so many different applications. So if you want to play around with this, all you have to do is you go to download.ushahidi.com and you'll see you can download a number of different mobile apps for the iPhone, the Android, Windows Mobile and some Java apps as well and the Blackberry will come in later this year. And then all you have to do when you open your app is point it to rp11.crowdmap.com and you can check in right now and mess around with it or you can go home and create your own check-ins and the way you would do that is you go to crowdmap.com. I didn't mention Crowdmap before but really all Crowdmap is, is the Ushahidi platform but in the cloud. It's a hosted version of the Ushahidi platform. So Crowdmap is like the Google Docs of Ushahidi. You don't have to download anything. It's just in the cloud. You just start mapping in a minute. You sync it with your smartphone app and you're on your way. The good friends of ours did something even better in London during the student protests recently. They developed a danger compass and so they're red points to where the cops are so you don't want to go in that direction and the green is the safe way out because the cops have this tactic of basically circling the protestors and basically holding them hostage. So we're hoping to do something like this. I think it's a phenomenal idea. It's very intuitive and allows people to coordinate very quickly. So what's next? Well, we've seen over the past six weeks or not six weeks, sixty weeks or so, is more than six thousand maps, live maps, using the Ushahidi technology launched in more than forty different countries for basically, I mean, almost as many different reasons. We've seen election monitoring, environmental monitoring, human rights. You name it. You've got an idea and it can be mapped. It's probably something that you can do or that's already been done before. And this Russian friend of mine had made a good comment in a recent blog post that, you know, radio gave each event a sound and TV gave an image. Then this mapping reflex that we're seeing now is sort of giving every event a geographic location. It's almost, in a way, closing the circle of senses that we would want to have. And just to make sure you don't think, I'm Mr. Dispaired, Gloom, Depressed, Violence, Disasters and so on. The Ushahidi platform can be used to map whatever you want. So this chap decided that he likes burgers and he wants to create a burger map of the United States to find out where the best burgers are. And I guarantee you that he didn't map all these four hundred spots. A couple of other hundred people who decided, yeah, I want to have my say. I want to say where the best burger is. So it's a very similar dynamic that we see in Wikipedia, right? Why do people get in Wikipedia and create articles, you know, 27 million pages worth? People want to have a voice. They want generate content. They want to share. And we're seeing this kind of dynamic and reflex now increasingly happening with maps. So speaking of food, just have a few more slides. I want to talk about the idea of crowd feeding. We talked a lot about crowd sourcing. But crowd feeding is really important. And what crowd feeding is, is basically what you see on this in the category section. This was the first Ushahdi map that decided to divide the categories between problems and solutions. And that's really, I think, a very pivotal evolution, if you'd like, in how we use these maps because clearly in a disaster, in a crisis, this was during one of the worst snow storms in Washington, D.C., completely paralyzed the city. Nothing was moving. The official responders were completely overcapacity. So we know that in a disaster, we're not affected. We're not equally vulnerable, right? For political, social, economic, historical reasons, different communities, different populations have different levels of vulnerability. So those who are more vulnerable and who are more affected, can maybe send out a text message and say, I need help. And the part of this society that is less affected can help, can offer help, and usually wants to offer help, right? So if we provide this kind of solutions and problems, we can crowd source the problems, but we can maybe also crowd source the solutions, especially if we can start connecting and matching solutions and problems, like having a match.com, if you'd like, not dating, but for disaster response, to connect people. And I think this will really be one of the keys to building more resilient societies, because disaster responders cannot be everywhere at the same time, just like the journalists in Kenya cannot be everywhere at the same time. But the crowd is always there. Your neighbor is always there. So why not draw on this, because by definition, the first responders in a disaster are the disaster affected population. And this has since been used in Russia during the massive forest fires. This was the largest crowdsourcing exercise ever carried out in Russia. This was just at the beginning. That's why you don't see that many events. But this volunteer group, again, set up a call center, because elderly people were now going online, and they were doing the matching via call center. And it showed very, very clearly, in a way, the limitation of Russian statehood. It showed that the Russian government was definitely not in control and was not on par in being able to provide this kind of response. So last couple slides. We've talked about technology, and I think I've, you know, I'm excited about technology, for sure. But I want to be very clear that technology is at most 10% of the solution. At least that's what we believe, and that's what we say at Ushahiti. The technology is the easy bit. Now setting up a crowd map, setting up a check-in system is easy. It's the other stuff. It's the other 90%. That's difficult, and that we just better not forget or ignore. I promise you that downloading the Ushahiti platform will not automatically give you a staff training, funding, a media strategy, an outreach strategy, an evaluation framework. I mean, you name it. All that stuff is the other human stuff, if you'd like, which is the important stuff that needs to happen in order for that 10% to really make a difference. If that 90% is not there, you know, we've just scored a 10% on our final exam, and that's definitely a big fail. So technology is exciting and so on, but you have to first focus on people, then process, and then the technology. Okay. Last slide for real this time, and then I'd love to take your questions. I just wanted to end on perhaps a more personal note in terms of what all this means to me. By paraphrasing a good friend of mine who works for the New York Times, and he wrote recently in a really great op-ed, you know, they say that history is written by the victors. And now, today, unlike 1994, before the victors win, and indeed if they win, there is a chance to scream out with a text message, a text message that will not vanish, and a text message that will in fact remain immortalized on a map for the world to bear witness. So what would we know about what passed between the Turks and the Armenians, the Germans and the Jews, the Hutus and Tutsis, if every one of them had had the chance before the darkness to declare for all time, I was here, and this is what happened to me. Thank you very much. Great speech. Thank you. Do we have any questions? Thank you, Patrick, for your very enthusiastic talk. I was particularly intrigued with what you said about using mapping during protests, really in the minute where it was happening. But on the other hand, I was wondering, isn't this also extremely vulnerable to Jean-Pierre Foucault and to... You gave the example that activists could obfuscate their actions, but just as well, could the state mislead the activists at much less risk than if they have to go on the ground? So do you have some kind of solution or way to go there? That's a really, really important question. Thank you very much for posing it. Technology can be used for good and ill. I think the way that we use technology in a way just reflects our values as human beings. It reflects how we think and how we feel about life sometimes. And there's absolutely no doubt, and we've seen this, and this is not new in terms of social media. So repressive regimes have been using technology for many, many years, decades to repress, to basically have that advantage. And I'll give you a couple sort of examples as perhaps answers, and let me know if I don't completely answer your question. But first of all, the Libya crisis map, the one that you saw there, that's the public version of the crisis map. There is a password protected version. The public version is on a 24-hour time delay, and it's also redacted. You don't get the full description, you just get the title. And that's in part because we realize that, yes, you can give the UN better situational awareness with this live map, but heck, you can give Qaddafi forces better situational awareness. So what we did, the site that the UN and other humanitarian organizations were using was a password protected site which had more content, and that was live for that particular purpose. So that's enough. Honestly, I don't know. What's really, in a way, ironic is that it's the UN that wanted this public version. We were not going to make it public. And then within like three or four days, they said, we need to make some of this public. And so we did. I'll give you another example that's not particularly fun. But clearly, these regimes are becoming more sophisticated than not becoming stupider. So we saw what happened in Tunisia. According to some of the Tunisian activists like Sami Garbia, it was a Facebook revolution. We saw what happened in Egypt as well. Well, what do you think happened in the Sudan? Well, what happened was a few days before the Sudanese activists themselves decided, hey, we want to go vote protest as well. We want the world to see what's happening in Sudan. A Facebook group appeared, and this Facebook group said, hey, join the protest down in Khartoum in the square at 2 o'clock on January 30th. So all of these activists got together. They got really excited. They saw what happened. Mubarak fell, Benali fell. They show up to the square. And it turns out it was the Bashir government that had set up that Facebook group. They got arrested. They got tortured. They got beaten. They got their passwords for their Skype, Facebook, emails all taken. So I mean, yes, the answer is it's incredibly dangerous, and we have to be very careful. So one of the things we've done, we have a blog with a standby volunteer task force, and we've basically written up all this lessons learned and best practices and gotten other people who are more experts than we are to chime in and help us develop this, we call it a security and ethics of live mapping and hostile environments. So if you can add to that blog post, that'd be really helpful. Thanks. Yeah. Well, actually, I also would like to address a problem. I also very much like the project that you've presented. I just wonder, you know, like you, for example, described all these, well, branches popping up, people, you know, organizing sit-ins to feed the maps with data, et cetera, et cetera, without training some instructions, and then you go in. In such a serious situation like a crisis, I just wonder, you know, about the filter problem, the verification of data, you say, you know, you're kind of like looking for all kind of sources, et cetera, mass media, social networks, et cetera, and you're working with all these volunteers. So, you know, the classical problem of, I think, all sorts of like, you know, crowdsourced projects that deal with intelligent data. And you've mentioned, or you've described your project as some kind of like, well, Wikipedia version for the maps or something, and we see you in Wikipedia the added wars. So that would be kind of the point that I'm sort of feeling at, you know, like, who's sort of like in charge of, you know, like kind of like, you know, taking the responsibility of, you know, sort of like, yeah, data or not. Right. No, that's another incredibly important question. How did you say that? So first of all, just so the Ushahidi, the group, the company doesn't, we don't get involved in 99% of these maps, right? It's other people around the world. And when you download the Ushahidi platform, or your crowd map, or what have you, you are the moderator, your group, your organization, your volunteers, you know, you decide what gets published or not. So all the content that gets published on a map, on an Ushahidi map, has first got to be moderated, has first got to be approved. So if you don't think that information you received is accurate or what have you, you don't have to make it public. In terms of how you validate this information, there are, I think, different ways. It's clearly a challenge. First thing I'd say, though, is not to necessarily confuse Ushahidi with crowdsourcing. For example, what the UN is doing now in Libya, they have their own SMS numbers for Libya, Egypt, and Tunisia, and their staff are texting in information. So that's more trusted content. It's the professionals, right? Al Jazeera did the same thing a few years back in Gaza. Their journalists who were in Gaza who were texting and tweeting live to the map. So it doesn't have to be open. That's the first, that's the first answer. If it is open, I think there are a couple ways that you can go about verifying and validating. One is what the Egyptians did in November and December when they used the Ushahidi platform for monitoring the parliamentary elections, a project that they called Ushahid. As you may remember, Mubarak didn't allow any international observers to come in. So this Egyptian group said, you know, screw that, we're going to do it ourselves then. And what they did is they worked with a seasoned professional journalist from the Thompson Reuters Foundation who had had 20 years of experience. And she's the one who said, all right, this is how we verify information in journalism. And we should remember that journalists, the good ones, are very good at doing this. This is what journalists do very well, the good ones, right? They filter, they validate, they follow up, they have sources, they triangulate and so on. So she developed those guidelines which you can probably get still on their website. You know, if there are three different independent reports on SMS and three different numbers describing the same event, then you can assume perhaps you have three witnesses. Now that's not a guarantee. I'd be the first to admit that. She also, I think, said once we have two pictures about the same event, we'll mark it as verified and also video footage. And they were able to verify 91% of about 3,000 reports that were crowdsourced using these methods. And following up, by the way, there was a lot of follow-up because once you get somebody to send you information by tweet or SMS, you can call them right back up and get more information, put them on the spot and say, did this really happen? Or you have, I mean, it was a massive network of bloggers who were also going out on the streets and verifying. I'll end with two quick other points. One is something I, it was just in Kyrgyzstan. And what they did during the violence in the South last year is this woman who heads an NGO got on Skype and started a Skype group with her friends just to start talking about what was happening. Within two hours, 2,000 people across Kyrgyzstan had jumped the Skype group, joined the Skype group, and they were verifying information in real time. They were filtering it, and then when they found out that, because there were rumors on text message. There was rumors that the Uzbek army was invading from the South. So one of the people on Skype said, I have a friend who works in the border. I'll ask him. The guy's like, takes a picture. There's nothing here. There are no armies. And then they got the word out by media and by broadcast SMS saying, people, this is completely false. So it's not impossible. It is a challenge because of the real-time aspect of it. And the last thing I'll say is, look up Swift River. Swift River is another project from Ushahidi. It's a filter project, right? Sorry? It's a filter project. It's human creation with automated and natural language processing to cluster events and triangulate and create probability scores. What is the probability that this event happened given you have seven text messages, two tweets, one video, and one article from BBC News? But I wanted to take one more question. Because she was waiting. Sorry? I was going to ask about Swift River because we had Victor Mikliwicz, he last year, who spoke about Swift River and introduced it as a first idea. So I was actually just going to ask precisely that question, how developments on that project are proceeding. It's going better now than it was. It took a while to get to the stage. So the latest developments that have happened over the last two or three months, now I'm more compelled to use it, to be completely frank and honest. It wasn't quite there yet. But now you have the clustering mechanism. You have the filtering mechanism. It allows you to, you know, every time you get there, you decide what sources you want to follow, by the way. You just decide which sources you want to follow. And then Swift River pushes those reports to you. And whichever report you can vote on the report and say, yes, this is relevant or irrelevant. Yes, this is accurate. Or I know that this is inaccurate. And the algorithm basically learns. It says, oh, clearly this person doesn't think this Twitter user is accurate. So I'm not going to push this anymore. But this user is interested in this kind of information with these kinds of keywords. So I'm going to give her or him more of that information. And you can start within, you know, it depends on how much information is coming in. We did this for Libya and the UN used it for Libya. Within about an hour and a half, we had a pretty neat stream of filtered, relevant and content that could be considered more reliable. So it's free and open source. So if you have feedback on it, how we can improve it, please, please get in touch. Patrick Mayer, ladies and gentlemen. Thank you so much. Thank you. Thank you. Thank you so much. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you very much. Thank you. Thank you. Thank you. Thank you everybody for having me. Thank you for having me. Thank you. Thanks everyone. Thank you for olmuşing us. Thank you for gerne this. Thank you everybody.
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Maps are changing our world in ways we could hardly imagine just a few years ago? This presentation will explain why, giving a real world examples ranging from Haiti and Egypt to Libya and Japan. Today's maps are live maps that combine crowds and clouds to drive social change. The presentation will highlight the latest in the field of crisis mapping by drawing on the remarkable efforts of a new initiative called the Standby Volunteer Task Force.
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10.5446/19390 (DOI)
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Good morning. Good morning. So today I'd like to actually pick up on the question that was asked by the young woman over there in the previous lecture on how we assign and how we name our tetra-egyl-stereogenic center. And there's a nomenclature system called the nomenclature that basically allows us to assign what's called right-handed or left-handed stereochemistry. That's the convention that everyone knows of it. As long as we're all on the same page, that we all have the same way of talking about the molecule in the stereochemistry. Just like if everyone calls a three-carbon alkane butane or butane instead of prokane. So we're going to learn this nomenclature system today. We're also going to get more familiar with molecules with multiple tetra-egyl-pacemetric centers. Alright, the basic nomenclature is really very simple. Nomenclature consists of R and S to designate the stereochemistry. If you think of R, its Latin term is rectus, which means right. And we're going to learn that that also means clockwise. The left-handed notation is from Latin sinister. And we're going to learn that as synonymous with counter-clockwise. Alright, what I'm going to try to do just as in nomenclature naming alveoli is to do is to do the same thing as nomenclature naming alkanes and various other compounds. There's a series of rules to follow. I'm going to try to take us through those rules and I'm also going to make it as simple as possible. Now there's a lot of neat to stereochemistry. For those of you who have been seeing, there's some fun, there's some three-dimensionality. It's really a deep topic. I have a book that's about 1400 pages just on stereochemistry. And so one of the things that I want to do is to digest the topic and break it just at a simple level into some small, light-sized pieces. So come along with me on this journey. Alright. So, first thing we need to do is identify the tetrahedral stereogenic center. That's pretty easy. So usually at carbon atom, we have four different things on it. We start with the word identical. I am. Different. Different. Different. Different. Different. And then what we need to do is to rank the substituents. Alright. Let's take an example and we're going to take the two butanol that we used before as an example. So I'll rank that again. So pretty obviously the carbon with the hydrogen, the hydroxyl group, the methyl group, and the ethyl group is the carbon, the only carbon in two butanol that has four different substituents on it. So this is A, and in this case the only tetrahedral stereogenic center. Alright. Now what we need to do is to figure out the priorities of the substituents. The first way we rank priority, the most important way is by atomic number. Highest atomic number gets you the highest priority. The lowest atomic number gets you the lowest priority. Kind of makes sense. You're looking at the periodic table. Oxygen is at 8, carbon is at 6, hydrogen is at 4. So for priorities, it's pretty easy to see that our OH, the hydrogen on here is going to be 1. I'll just put an arrow here, highest atomic number. And our hydrogen then is going to be 4. I'll put an arrow here, the lowest atomic number. Now we're faced with the situation of the metal and the ethyl group, and they're both carbon. So our first ranking is at the atoms attached, they're the same, they're both carbon. So what we do now is we move outward away from the tetrahedral stereogenic center. And we identify what's attached to those carbon. So both of these are carbon, all right, C and C here. But attached to this carbon is 3H is H, H, H. Attached to this carbon, we don't count this carbon anymore, we're just moving outward. Attached to this carbon, we're just moving outward. Attached to this carbon moving outward is another carbon in two hydrogens. So this one is C, H, and H. And now we just look, okay, they were both the same atomic number. But moving outward now, we have a higher atomic number, carbon 6, attached to this carbon. Then we do to this carbon. So this substituent, the ethyl group gets a ranking of 2 and the methyl group gets a ranking of 3. So the first rule we can say is higher atomic number, is higher atomic number, higher atomic number leads to higher priority. And realize that when you then are comparing atoms of the same atomic number, you just move out. And that rule is going to get you pretty far. Just like in nomenclature, there's a lot of stuff that can be really arcane. I'm going to try to take us through the simplest and most relevant stuff. Now the next operation once you've ranked the substituents is just to look down the bond from the carbon atom, from the tetrahedral stereogenic center to the lowest priority atom. Get going, everybody. Ok. All in all. Thanks for coming here. I'm going to do my own pump. And then what we do is determine the direction 1, 2, 3 going around as it clockwise or counterclockwise. And then we weigh this 1 parallel and weigh this 1 parallel n with x trades. Question? I'm still a little bit confused. How do you tell the difference in priority between the ethyl group and the methyl group? Ah, question. How do we tell the difference in priority between the methyl group and the ethyl group? Both the ethyl group and the methyl group are carbonated. So we know they're both at the same level there of their atomic number. So now we have to break the time. And to break the time, what we do is we move outward along the chain and say what's connected to each carbon? Connected to the methyl group is three hydrogens, all atomic number one. Connected to the ethyl group, we're just moving out of it so I'm not counting the tetra-needral asymmetric center, is a carbon, the terminal methyl group on the other side, and two hydrogens making up the methylene group. So now we say on the tiebreaker, the ethyl group has the carbon on the right, has a carbon attached to it, and that trumps hydrogen attached to the other. So that gives us an assignment of two on the priority of the ethyl group and three on the priority of the methyl group and, of course, group four on the hydrogen. Other questions? These are good. These are really important to be taking about this. Ah, what happens if you have the same groups on either side? So let us pretend for a moment that we had two ethyl groups. Somebody, what would we do in this case? It's not a stereogenic center. If they're the same group, then we don't have a tetra-needral stereogenic center. We need to have four different substituents. So in that case, we have a plane of symmetry in this molecule in three-pentadol, and as a result, we know immediately that we don't have a chiral molecule. Other questions? All right, next thing is visualization. What we want to do is site down, look down the bond to, from the carbon atom to the hydrogen atom in two-butadol. And so I'm going to draw things out, and here's where, if you're not yet proficient with visualizing, here's where models can really help you out. So here's our OH is one, our ethyl is two, our methyl is three, and I have this hydrogen going back. So we're looking down the bond to it, and I go one, two, three. Our direction is clockwise, and that means our tetra-needral stereogenic center is R. So we call this compound R2-butanol. We always, by convention, put the R in the parenthesis. Let me do this with some video projection, because as I said, we need to become proficient at this, and it takes a little bit of practice. Let's see if I have a model of R2-butanol. So I'm going to do this two ways. We'll take it slow. I'm going to show you how I do it, and then for people in the back, we'll do it on the video projection. So here's the model that I built. Please, if you have your models, pop yours together. No better time to get your exercise and visualizing it than right now. All right. So, hold up your models. I want to see more of them. Still a neighbor in auto-papery or a makeup friend. We just had a seminar speaker who was an undergraduate at UCI in 1995 or 1998. She's now a professor at the University of Toronto, and she was trying to decide whether to take the chemistry general, the Chem51 or Chem52 course. She ended up taking Chem52. Not only did she end up getting inspired to go on in chemistry, organic chemistry, because that was what she also met the man who became her husband in that class. So go to your neighbor. Go to your neighbor. Go to your model. And borrow a model. All right. So I'm going to do this here, and then I'm going to do it up on the video projector. So here's my two-butanol, and you notice we're looking down the CH bond. We go one for the oxygen, two for the ethyl, three for the metal that's clockwise. Let me put that up on the video as well, just to make it maybe a little easier to answer. No. Working from the lamp. All right. So, here we are. You notice, and this is the case, because if you don't site down the bond, you'll site in the wrong direction. You'll get it exactly backwards. So our tetrahedral stereogenic center is in front, where my finger is. The hypochism is the lowest priority substituent. Is it back where my finger is? We have the oxygen atom. We're getting a mirror projected here. Yes. Ah, right. All right. Yes. This is the one case where I think video ends up being a 1, 2. That's weird. Okay. We're going to stick to this on the model. So again, one for the oxygen. Everyone's looking down. Here's the oxygen. It's the same as on the blackboard. Here's the ethyl group. Here's the methyl group. And so, from your point of view, one, two, three is clockwise. So this is telling you where our hydrogen is. The question is, is this telling us which direction? Well, if you could take it to waves. Here, I've given us a molecule, and I've said which wave is it. If I said draw S, then you draw it in a particular wave. And the way I always do it when I'm asked to draw S or draw R is I go ahead and I simply draw one, because I don't know off the top of my head. Check it. And if I end up not getting it right, then the trick is you just swap the two substituents. So if I go ahead and simply swap two, not three, not one, but two substituents, then that's what we call inverting the tetrahedral stereogenic center, or inverting the chirality of the molecule. And now I know that this molecule is the opposite. So this one is S to butanol. Now you can do this a couple of waves. One way is you can simply do the rotation in your head. You can go ahead. I'm going to swap them on my plastic models. You can go ahead and do the rotation in your head and spin the molecule around. So in other words, I can go ahead and say, alright, I will just spin this around like so. And then when I've spun it around, I'm citing down the CH bond, one, two, three, it's counterclockwise. But the other way you can do it is you can say, well, let's draw in this way, but I know if I reverse things, if instead of citing down the bond to the lowest priority substituent, I'm citing from the bond with the lowest priority substituent in front instead of in back, then everything's reversed. So in other words, you look at this molecule as I'm holding it now with the hydrogen pointing right out at you and the oxygen and the methyl group and the methyl group. The way I deal with this is simply I say, well, it's all backwards. So when I go one, two, three, oxygen, methyl, methyl, I'm going clockwise, but we're citing in the wrong direction on the bond, which means in reverse it's counterclockwise and the steric chemistry is S. You can do it either way in three different things, all equivalent that we've done. One is we've gone and said we can rotate the molecule and simply make a new drawing. Another way is to say, well, we know we've got this molecule by simply swapping the oxygen and the hydrogen and we knew when it was like this, it was R because we were citing down the bond. So if we swap two substituents, we invert the stereocenter and we go from R to S. Or you can go ahead and say, well, I'm citing it backwards, so what should be clockwise is counterclockwise and what should be counterclockwise is clockwise. Questions or thoughts? And of course, always the fallback is build a plastic molecular model. And when you're learning, when you're starting to see these drawings on the blackboard for the first few times and they're not yet clear, that tangible model, that model you can hold in your hand, grasp the substituents, look down the bond, that is really the thing that's going to get these blackboard drawings into your brain. So let me write that take off. All right, so let me write that take home message here just so you can get it in your notes. Swapping two substituents. Swaps the stereochemistry and then let's try another example. All right, example I want to try right now is two chloro-tetrahydropyrene. And just like we did with two butanol, we're going to determine whether the drawing that I'm about to make is R or is S. We're going to assyllate the absolute stereochemistry. So tetrahydropyram, I've mentioned before, is a five-membered cyclic ether containing one oxygen. This is the tetrahydropyram ring structure. The oxygen gets numbered for one position, so the chlorine is at the two positions. That's our priority, that's just numbering the chain. So here's the structure, let me show you how I think about it. Now one way I think about it is to start by simply drawing in my hydrogen. Where am I drawing my hydrogen? What's the tetrahydro-stereogenic center? The carbon with the chlorine on it. And that hydrogen is pointing out because the chlorine is pointing back. Which substituent has the highest priority? Chlorate. So that gets us to sign number one. Which one is the second priority? Oxygen. Third priority? Carbon. Fourth priority? Hydrogen. Which way, if we look at the molecule as it's drawn, are we looking down the bond to the lowest priority substituent? No, it's reverse. Two things we can do. One is we can flip the molecule over. All we do is rotate it 180 degrees, I'm going to pick it up and flip it over here. Now the hydrogen is going back, we're citing down the bond to the lowest priority substituent. We can go one, two, three and say this is counterclockwise and this molecule is therefore S2-chlorotendrohydropyram. Another thing that we can do is simply make a physical model. Our oxygen is just the tetrahedral construction with carbon, with the red pieces just like carbon. The trick with the oxygen is those two extra sticks on it represent lone pairs. Chlorine by convention, since chlorine is green, chlorine is typically represented by a green ball. Chlorine is a yellow-green gas, of course very poisonous. You smell it with bleach or with swimming pool water. And you can put on your chlorine and make the model. And then you don't have to worry about any sort of drawing on the blackboard. You just say, well, okay, I'll just look down the bond. The bond is pointing back. Here's the chlorine, here's the oxygen, here's the carbon, we're counterclockwise. So you never have to worry about being able to visualize. And if you're proficient at this, what you can do is just keep it all in your head and say, oh, well, the hydrogen is pointing out, which means all the rules are backwards. So since the hydrogen is pointing out and we're going chlorine, oxygen, carbon, clockwise, that's really counterclockwise because everything's backwards. So counterclockwise means s. And the more you practice, the more you're going to be doing this automatically. But at this point, find something that's comfortable for you and practice. Whether it's starting with the models or physically doing the rotation on the blackboard or simply mentally keeping track of everything on the blackboard. All right. Couple of more little rules. So couple of more little rules. One of them is how we treat double bonds, triple bonds. And we're going to pretend something. All right. Here's an example where we have a double bond and they have an OH going out and a hydrogen going back. What we're going to do is pretend that this carbon here, the one I'm pointing to, the one of the double bond, instead of being a double bond is bonded to a second carbon and did own for this one. So what we're going to do is pretend that our structure is like this. All I've done is to go ahead and I'll draw on the hydrogens too. All I've done is to say a double bond counts as being bonded to not one carbon but two carbons. In other words, on this substituent then we say this substituent, instead of counting as having one carbon attached to it, counts as having two attached to it. So this carbon counts as having a carbon and a hydrogen attached to it. Whereas this substituent here counts as having a carbon, a hydrogen and a hydrogen attached to it. Does that make sense? So the idea for dealing with double bonds is simply just a way of keeping track. Say two bonds to another carbon counts as two carbons. I have it just in my mind just draw a second carbon but you can also say, alright, well we're going to count this carbon twice so we're going to say that this carbon, since it's got one bond to a carbon and another bond to a carbon, it counts as being attached to carbon, carbon and hydrogen. This carbon counts as being attached to one carbon and two hydrogen. And so our prioritization at this point is that the OH group is number one, the hydrogen is number four and by this convention the double bonded carbon now counts as number two and the single bonded carbon counts as three. So when we assign stereochemistry we're siding down the CH bond, we're going clockwise and so this molecule counts as being our stereochemistry. In other words, this molecule counts as R3 methyl 1Nt. Nomenclature here, we haven't learned yet. This is a nomenclature for alkanes, it says that the double bond is at the one position. Obviously the 3 methyl is just like our nomenclature for alkanes, it says the methyl group is, whoops, ox. Actually the example I was going to do for that was simply same issue here. So I'm going to skip the nomenclature of this molecule because this molecule becomes, pentene becomes one pentene if you want to know what becomes R1 pentene 3-ball. So the main point, don't worry about that nomenclature, the main point is for our stereochemistry. Alright, one more example with carbon-carbon bond, so we set a double bond, counts as having two carbons bound to a carbon. A carbon-carbon triple bond counts as having three carbons bound to a carbon, yeah. Yes, say thank you. Why do I just prioritize this carbon? Because we have one, so the question is why do I just prioritize this carbon? We have one tetrahedral stereogenic center, I look at the four substituents attached to it and I say we have chlorine first priority, oxygen second priority, carbon third priority, hydrogen fourth priority. So I never have to go out, we never have to have our little runoff election saying there are two carbons attached. If I had a molecule like this, let's say with an isopropyl group and a methyl group attached, then I'd have to start to say ah, we have two carbons, but which carbon is higher priority? So it would be one for the chlorine, two for the oxygen, three for the carbon with two carbons attached to it, and four for the carbon with only hydrogen attached to it, does that make sense? As long as we are only dealing with elements of different atomic number, we never have to go on further down the chain. And of course with one tetrahedral stereogenic center, we're only worrying about what's attached to one carbon. What? Could this carbon be the third substituent, but it's not attached to the tetrahedral stereogenic center? Everything depends on what's attached to the tetrahedral stereogenic center. Let's try two more examples with double and triple bonds. So start with a triple bond, and let's take this compound here. So just as with a double bond, we pretended that we had two carbons attached, one for each of the bonds. With a triple bond, we pretend that we have three carbons attached. So in other words, now we're in a situation where we go and say this is like, I'll again write, pretend, carbon bound to a carbon, but with two carbons attached. Oops, do we net all of here? And so now in prioritizing, obviously hydrogen is the lowest priority substituent. Obviously the hydrogen gets priority of more. The carbon that's the triple bond, we count as having three carbons attached to it. So we count this as having carbon, carbon, and carbon attached to it. We count this, the ethyl group, as having carbon, hydrogen, and hydrogen attached to it. And we count the methyl group as having hydrogen, hydrogen, and hydrogen attached. So by this little convention, by this little way of pretending here, now we go first priority for the acetylene group. The triple bond and carbon. Second priority for the ethyl group. Third priority for the methyl group. And so this stereocentric, clockwise, is R. And of course you don't have to have any hydrogens attached to your tetrahydro-stereogenic center. You could have all carbons attached. You could have a carbon atom with a methyl group, an ethyl group, a propyl group, and a bule group. And you would just keep moving along the chain. The methyl group would be lowest priority. The ethyl group would be next lowest priority as you move down the chain. The propyl group would be next. And the bule group would be highest priority. So you just continue along comparing until you get a difference. Let's try one more example with a double bond. But this time I want to make it a double bond to oxygen. And so I'll draw an aldehyde. And I'll give us an alcohol group. And this aldehyde has the same type of conundrum. We have a tetrahydro-stereogenic center. I put my finger onto it. We have a hydrogen. The hydrogen is lowest priority. Conveniently we're siding down the bond to the hydrogen. Now we have three carbons. A methyl group has H and H attached to it. The carbon with the OH group has OH and H attached to it. The carbon that makes up the aldehyde also has an oxygen and a hydrogen attached to it. But just as we pretended in the carbon double bond that a carbon-carbon double bond meant that there were two oxygens attached, two carbons attached, in the case of a carbon-oxygen double bond, we pretend that we have two oxygens attached. In other words, we say it's OH and H. We treat our aldehyde and we treat this as equivalent to with the carbon having two oxygens attached. And so this particular example, our priorities go 4, 3, 2, and 1. And so our stereochemistry here is counterclockwise. We're conveniently siding down the bond. It's S stereochemistry. All right, when you have two isotopes and almost invariably we're talking hydrogen and deuterium here, you can also have a tetrahedral stereogenic center. And so I'll give us one example where now we have two isotopes of hydrogen attached to one carbon. One of them is deuterium. Deuterium is H2. It's heavy hydrogen. Regular hydrogen is H1. Not surprisingly, higher atomic mass counts as higher priority. And so our deuterium gets a priority of 3. And now we go 1, 2, 3. This isotope or this molecule with isotopes has an or stereochemistry to it. All right. What is deuterium? Deuterium is, I'll explain while I race the board, deuterium is an isotope of hydrogen. It's present in one part, in 7,000, in everything, in water, in your body, all over the place. And deuterium is simply often put in as a label into molecules. So you can make molecules with one deuterium in it. It's called heavy hydrogen. All right. Last time we drew some structures of cyclo pentanol, of methyl cyclo pentanol, and I want to show you a trick. So last time I permuted the stereochemistry and drew out four different molecules. And I called them A, B, C, and D. And I think I drew them like this. I just want to show you how we can very quickly assign the stereochemistry to all four of these molecules of two methyl one cyclo pentanol. The trick is we only have to assign stereochemistry to one of them. And then I just watched what I do with the stereocentrics. And remember, this molecule was two methyl one cyclo pentanol. And I'm just going to start with the molecule on the left. And in my previous lecture where I had all of these and I projected them, I called it molecule A. And I'm going to start with the stereogenic center at the one position. The hydrogen is priority one. The hydrogen is priority four. We now have to look at the two atoms attached to that stereogenic center. The carbon where my finger is has a carbon and two hydrogens attached to it. The carbon where my finger is here has two carbons and one hydrogen attached to it. In other words, the carbon at the two position is priority two and the carbon over here is priority three. We're citing down to the bond, to the hydrogen, we're citing down the bond to the lowest priority substituent. So this substituent is R. That's this stereocenter. I'm going to redraw the molecules, same molecule, but now we're going to focus on the other stereogenic center. On this stereogenic center now, our hydrogen is still lowest priority, lowest atomic number. Now we have three different carbons attached to it. Carbon, carbon and carbon. The methyl group has all hydrogens attached to it, three hydrogens. This group, the one is the one position of the ring, has an oxygen, a carbon and a hydrogen. Oxygen is higher priority than anything else in the molecule. This one here has a carbon and two hydrogens. This substituent becomes priority one, priority two, priority three and so this substituent, this stereochemistry is S. This allows us to assign all of our stereochemistry. This molecule is one R, two S and then two methyl, one cyclopentadol. The next molecule, I've inverted both of the stereocenters. I've swapped the two substituents, the hydroxy and the methyl group. This molecule is one S, two R. The third molecule, we kept the original stereochemistry at the top one but swapped the second. So this molecule is one R and then two R. And the last molecule, we've swapped them around again. Let's see, is that right? Yes. So this is one R, two R and the last one is one S, two S.
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -1:13 Nomenclature of R and S -3:11 Tetrahedral Stereogenic Center -6:40 Priority Around Stereogenic Center -13:06 2-Butanol Example -25:05 Tetrahydropyran -31:09 Double Bonds and Triple Bonds -39:34 Triple Bond Example -42:47 Double Bond Example -45:16 Isotopes -47:04 Methylcyclopentanol
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10.5446/19393 (DOI)
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Good morning. So today we're going to begin talking about Chapter 6. And Chapter 6 sort of leads us into the remaining part of the horse, which really in some ways the gameplay to the rest of our, really to the remaining three quarters of organic chemistry. We've been laying a lot of framework and talking about structure, molecules, understanding the birds and started chemistry, getting a little bit of an introduction to the nomenclature and permutations of molecules and talking about how it hangs. And so now as we go into the rest of the course, we're going to be doing a lot of discussion of cultural roots and their reactivity. And remember, I said this was one of the biggest organic chemistry. Chapter 6 is really the gateway to this, particularly in relationship to Chapter 7, Chapter 8, Chapter 8. Chapter 7 and 8 deal with two types of reactions, substitution reactions and elimination reactions. And this is where organic chemistry really gets fun, you start to learn how to interconvert molecules, you start to learn what turns a lot of people on organic chemistry, and that is how to build molecules, organic synthesis. Chapter 6 begins talking about reactivity and how chemical reactions occur with the idea of setting the groundwork for thinking about reaction mechanisms and all the processes that occur. And it ties into that second maybe we talked about, current arrows. So to set the groundwork, we're going to in Chapter 6 be talking about types of reactions. And we're not going to discuss every type of reaction, but we're going to set a little bit of the groundwork on two types of reactions, on substitution reactions and addition reactions. Basically learning to make sense when you see an organic chemical equation of what's going on, literally how to read what's going on and how to understand it. We'll talk about the mechanisms in this chapter. How reactions, particularly of substitution and elimination reactions, and this will set more of the groundwork for understanding things like the stereochemical course of elimination and substitution reactions. We'll also learn to think about reactions as over going, overcoming energy barriers and going from reactants to intermediates and intermediates to products or alternatively from reactants directly to products. So as I said, we'll be talking about the mechanisms and particularly the energetics involved. And part and parcel with energetics of reactions are the rates of reactions and the discussion of rate determining steps. And this is what we'll be getting over the course of this week. This is also the last week of the course where we very conveniently have the lecture in one week, discussion in the next week, and then a quiz in the following week to sort of bring it all home. This is where the quarter system gets us a little bit more compacted. So as we move into chapter seven and particularly chapter eight, there's going to be even more burden on you to keep on top of things. So we'll be taking chapter seven up through Thanksgiving week, discussing that, including the week of Thanksgiving, discussing that Thanksgiving week and then having a quiz on it in the following week, the very last week of class. And then the very last week of class will be discussing chapter eight, and you'll have that going on in both the lecture and the discussion. And of course, we'll move into the final and the following week. As I've already said before, I wish we had a little bit of an extra reading period to digest the last chapter of the class. All right, so let's take a look at one chemical reaction. I'm going to write it a couple of ways. Question. What's the next quiz going to be on? The next quiz is going to be on chapter five on Monday. So let's take a look at a particular reaction. We'll write it a couple of ways and we'll use it. Two others, the sort of springboard, can talk about some of these points here about the types of reactions and the mechanisms of reactions and later on, energetic profiles. So let's take a look at the reaction of ethyl iodide, also called Iogethane, with sodium cyanide. Now I'm going to start to write this in various ways that you might see in organic chemistry things. One thing you probably will see is an organic chemist will often just focus on the organic product of the reaction. So you may see this reaction written like so, which would upset very much someone teaching general chemistry because it's not a balanced equation, and yet we're really organic here. We're, of course, talking about a reactant and another reactant going to an organic product. Some people might even omit writing about this in parenthoracic parentheses, sodium iodide, which is what many organic chemists would think of as a byproduct of this reaction. The other thing that you'll often see, we've done this a little bit so far, but I'm going to do this explicitly, is something written below the arrow. Virtually all organic reactions are carried out from solvents. Solvents do a few things. They allow reactants to mix. They allow different species to get together. They allow a compatible environment. So for example, in this reaction, sodium cyanide is an inorganic salt. Ethyl iodide is a liquid. Sodium cyanide doesn't dissolve in ethyl iodide. Ethyl iodide is a mildly polar organic liquid, almost non-polar. Sodium cyanide is a salt. You need very strong interactions to salivate the sodium and cyanide ions. Ethanol is a great solvent for this because ethanol is like water in some ways, it's a hydrogen balance. It has strong dipoles in it so it can stabilize cations and anions so they can dissolve. It also is miscible with most organic compounds so it brings the two reactants together. The other thing that organic solvent does is it allows heat to be dissipated. Most reactions that proceed, most reactions that go to the right end up releasing heat. And as such, if you just mix two pure reactants, if the reaction becomes exothermic, if the reaction is exothermic, you may get a lot of heat very suddenly, literally potentially getting an explosion. Solvents dissipate heat, they also can boil to relieve heat through evaporation. And often a reaction in your flash ports will be carried out in a flash with a reflux condenser so that solvent can be boiled to heat the reaction up, but also so that any heat can just go into boiling salivate, so that the solvent can then condense for the condenser. Now, organic chemists are so organocentric that you may see the same reaction written as follows. Where you simply put the organic reactant on the left-hand side of the arrow, put your reagent inorganic, organic, or organometallic compounds that participate in the reaction over the arrow, solvent under the arrow, and your organic product on the right-hand side of the arrow. And all of these ways of writing this reaction are correct writing it with the byproduct shown, without the byproduct writing sodium cyanide on the left of the arrow, writing sodium cyanide over the arrow. They're all just putting slightly different emphases on what we're thinking about things. Now, this particular reaction falls into the class of reactions known as a substitution reaction. In the substitution, one group, one group of reaction, one group literally replaces another. So, I'm going to write this same reaction, but I'll show the bonds that we're making and breaking. So, we have a bond between the ethyl groups, specifically between the methylene carbon and the iodine. And we have cyanide and anion. And so, we substitute the bond to the iodine. We substitute the iodine with a cyanide group with a nitrile group. The other product of this reaction, specifically as I've written it, is an iodide anion. So, basically, cyanide comes in and it replaces, it substitutes the iodine, and now we end up with cyanide bound to the ethyl group and iodide kicked out. Let's write this as Cn replaces i in this reaction. So, what we're doing to be very specific is we're breaking the sigma bond and we're forming Cc and cyanide. So, we're breaking the sigma bond. So, we're breaking the sigma bond. So, we're breaking the sigma bond. We've already seen that one of the ways we think about reactions involves the use of arrows of various sorts. And this really is integral to the language of organic chemistry where specific arrows have specific meanings. Some of you may find if you don't use or have already found on your midterms, if you haven't used the correct sort of arrow, it's communicated and perhaps even lost credit for it. So, I'm going to talk a little bit explicitly about various sorts of arrows that we've been using to show reactions, to show equilibria, to show resonance and to show bonds making and breaking. So, let me write a couple of these out. So, when I wrote the reaction before, I think we wrote something to the effect of CH3CH2I plus NaCn goes to CH3CH2Cn plus NaI. So, that arrow there is just specifically a reaction showing reactants to product. It doesn't say anything about whether it's an equilibrium. And that's fine. We've communicated a chemical transformation. Technically, technically, I can say every reaction is nominally reversible. By that I mean it's never really completely wrong to think of any reaction as an equilibrium. But in some cases, they're so energetically downhill, it's kind of silly. Let me show you an arrow we could write to indicate specifically that we were talking about a reaction that's an equilibrium. If we use this sort of arrow, this arrow implies an equilibrium. I generally write this as two regular arrows, one over the other. You'll also see this written in particularly type set where you have arrows like this. I think the chemical drawing program I specifically does is that your book may do that as well. Neither one is particularly different from the other. I'll show you a case in just a moment where there is a big difference between an arrow with a double head on it and an arrow without. Let me show you one more variation on the arrow. Same reaction. It's probably a little bit more correct for this reaction is showing that the equilibrium lies very far to the right. If you're going to say it's an equilibrium, this particular reaction could be one where you want to indicate that it's not an equilibrium in the middle. It also indicates the equilibrium lies to the right. All of those sorts of arrows on the blackboard on your left really are the sort of arrows you've seen in general. Other sorts of arrows are unique to organic chemistry and ones that as I've indicated on many occasions really are central to our thinking about how bonds get made and how bonds get broken. Curved arrows show the flow of electrons making and breaking of bonds. Specifically, a curved arrow with a regular double head on it shows the flow of an electron pair. And that kind of makes sense given that all of the bonds that we've talked about involve two electrons for every single bond. So a double bond involves four electrons. In other words, bonds involve electrons in pairs. We'll say in bond making and bond breaking. So it makes sense that your arrow has to start where the electrons are. You can't just have an arrow, a curved arrow starting on an atom where there are no electrons. It needs to start on a lone pair around a bond where the bond is breaking or the bond is moving. So for example, in the reaction that we're talking about here this reaction of ethyl iodide which we'll learn is called an SN2 displacement reaction. I would show electrons flowing from the lone pair on the nitrile to the carbon atom. This is going to represent the new bond that's being formed, this flow of electrons. And concurrently, electrons are going on to the iodine atom. And here's our new bond to the cyanobruth. Depending on whether I'm feeling like it, I might show all of the lone pairs on the iodine. Often because organic molecules are big, often people only show the electrons right at the region, right at the center of the reaction just because there's a lot of extra atoms in the molecule. But here I'm feeling good and I will go ahead and draw everything out. And here's our iodine anion. Now there is another class of reactions and there are reactions that involve single electrons moving. A lot of these reactions involve free radicals, either the reactions of free radicals. A free radical is a species with one electron on it. They're reactive. You've probably heard of this term. You've heard the term radicals in the aging. Okay, these are reactive species that form under a variety of conditions, including oxidation reactions from molecular oxygen and various sorts of photochemical reactions from sunlight. And these are reactive species that have a single electron. We use what's called a fish hook arrow to show the motion of single electrons. And by a fish hook arrow, what I mean is a curved arrow, but instead of having a double head on it, having a single head on it. So an example would be the breaking of a bond in a peroxide. The oxygen-oxygen bond is very weak and it breaks easily, for example, with heat. So if I take a simple peroxide, this one is dimethyl peroxide. And let's say we heat it up. The delta over the arrow means heat. Just a green-thletter delta, a capital delta, like you'd see in a fraternity t-shirt, often used to mean heating a reaction. So breaking the central oxygen-oxygen bond involves moving one electron onto oxygen. So I use one fish hook and moving the other electron from the central bond onto the other oxygen. So I use another fish hook to designate this reaction. So the overall result is that we get two methoxy radicals. Each of these methoxy radicals has seven electrons around oxygen instead of eight. One electron in the bond from one pair of electrons in the bond from oxygen to the metho group. Another two lone pairs of electrons and then an odd electron. And the motion of that odd electron from the bond onto the oxygen atom has been shown by this fish hook designating the breaking of that bond. When we talk about bond energetics, sometimes students get a little bit confused because there are two different energies involved in breaking bonds. One is what you traditionally think of as bond strength. That's the energy to break a bond homolytically, homo-like, lytic cleavage, just as we've done here, breaking it so that one electron ends up on one atom, one on the other. That's the general strength of a bond. What students will sometimes find confusing is the look at a reaction like this where we're having a reaction occur and then they'll say, wait a second, I thought you said this bond is stronger, this bond is weak, and it's a little bit different when you're breaking bonds with flow of two electrons versus a table of bond strength feeling like just snapping a loop of a hand down. All right. Last arrow, and you've seen this, the double-handed arrow. These indicate resonance. So on the midterm exam, for example, you saw the use of this arrow to indicate two resonance structures of an emidazolean cation. That was, I believe, on the last problem where I asked you to draw two different structures, and I think the structure that I've provided I think I had asked you to fill in a hydrogen to show the resonance structure. So I think that the structure I provided or almost provided was this structure that you had to fill in the hydrogen and the positive charge. And then we had a double-handed arrow showing resonance, showing the resonance structure. And this was the structure you were asked to provide. And of course, the double-headed arrow means that it's both at the same time. Unlike the arrows where we've seen going from reactant to product or arrows showing flow of electrons, the double-headed arrow is simply reminding us that the emidazoleum, the methylemidazoleum cation isn't solely the structure on the left. It isn't solely the structure on the right. It's both of them, and it's both of them at the same time. We're not changing between them. We're not oscillating or vibrating between them. These are just two different pictures, neither of which is complete, and together they make up a more complete picture of the same thing. All right, let's talk about a different type of reaction, one that you're going to see. We'll talk about addition reactions. We talked about substitution reactions. One basic idea of an addition reaction is we're going to add something across the pi bond. In the process, we're going to break the pi bond and form two new sigma bonds. We take an alkene like cyclohexene and we treat it with bromine. Remember, I'm using a chemical reaction showing that we're having an organic reactant on the left, a reagent, which is also a reactant, over the arrow, and a product, di-glomosynchlohexene. Of course, what we're doing in this reaction is we are breaking the pi bond. We're forming two new sigma bonds. We're breaking the basic nature of an addition reaction. In this particular case, so an overall addition reaction can involve many, many different types of processes. In this particular case, we're also breaking the bromine bond. Sometimes we don't even have the two groups of the same double bond coming from the same reagent. Yet, you can still recognize the basic form as an addition reaction. Later on in the class, you're going to be learning about, later on in the sequence, you're going to be learning about Grignard reagent. Let me borrow an example from your textbook, which allows you, this is actually in the current chapter, so it's a nice chance to see what we're talking about. Here's acetone, and we can treat it with a Grignard reagent. Later on, you're going to learn that the name of this reagent is called methyl magnesium bromide. It's an organometallic reagent, and it acts as a nucleophile toward the carbonyl group. Right now, though, we're just looking at the basic number of the reaction and not the details of the mechanism for the reagents. So in the first step, I mean, this is literally, you will add one reagent to your acetone, sometimes you add the acetone to the reagent in the class, then you'll add another reagent, in this case water. And when you're done, the product of the reaction is terbutanol. And even though this is a very different reaction than you've seen thus far, and it involves different sorts of chemistry that you've learned about, you can look at this reaction and say, oh yeah, yeah, this is an addition reaction. He said in an addition reaction, we break a pi bond. We add a pi bond to the oxygen, and that pi bond is no longer there. We've broken it. And in the product, now we have two new sigma bonds. The oxygen before was bound to two methyl groups, and here it's bound to a third methyl group. So we formed a sigma bond to a methyl group. The carbon atom was bound. And the oxygen atom before just had a double bond, and now we have a new sigma bond to a hydrogen. So even this very different sort of reaction falls into the broad class of addition reactions. Questions? Right now we're taking kind of a look for 30,000 feet at a lot of what you're going to be learning over the remainder of the course and just getting a feeling for the different types of reactions. Again, in this view from 30,000 feet, one of the things that's very pretty is a lot of reactions have parent opposites. So the equal and opposite, the reverse, if you will, of an addition reaction is an elimination reaction. What do I mean by the opposite? I mean that in the case of an elimination reaction, we're going to break two sigma bonds and get a new pi bond. All right, let's take a look at an example of an elimination reaction. And indeed this is an elimination reaction that you'll be seeing in the very next couple of chapters. So we'll take a reaction. First I'll write it out in sort of a shorthand. And this molecule is tert-butyl bromide, also known as 2-bromotumethylpropane. If we treat it with sodium methoxide in ethanol and now you're seeing this grammar of putting the agents over the arrow and solvents under the arrow. I've already mentioned in the earlier class how one often generates this base sodium methoxide by throwing sodium metal into ethanol and letting it dissolve. If we do this, then the product of this reaction is an alkane, 2-metho-propane. So we can see there wasn't a pi bond in the reactant and now we formed a pi bond. Let's look explicitly at the sigma bonds that have been broken. So I'm going to draw out our bromobutane, our tert-butyl bromide rather large. And I'll draw our product large and I'll draw everything explicitly. So here's the pi bond that we formed. And you can see the sigma bonds that we've broken in going from a CH3 group to a CH2 group. We've broken one of the bonds to the hydrogen and in getting rid of the bromide, we've broken a bond to bromide. As we go on to learn about substitution and elimination reactions, we're going to be learning about species called reactive intermediates. We've already hinted at them with radicals. Certain organic species form transiently during reactions. Generally, these are non-species that you can put in a bottle. This of course means that organic chemists have worked very hard to figure out some of these species in a bottle because if you say there's a rule you can't do something, organic chemists want to figure out how to find the right way. However, let me show you general examples of the sort of reactive intermediates that you're going to see that in general just form transiently for a fleeting fraction of a second and then go on to a product. We'll throw them out explicitly because it's easy later on to get confused about the sum of the same shoots between them. Carbocannons are carbon-bearing reactive intermediates in which you have a positive charge in carbon in which the carbon lacks the complete content. We call them carbocannons because they are literally cations and the carbon would be like my A meter here. Not surprisingly, carbocannons are unhappy because they lack a complete octet and so they form transiently and then go on to carry out various reactions that give them a complete octet. In the case of the bond homolysis to form a methoxy radical we saw another type of species, a free radical. Radicals are species where you have an odd electron on an atom and a carbon center radical is simply a radical with an odd electron and carbon. Just like carbocannons, they're not happy. Carbon wants to complete octet and it does various things to get it. What's interesting is that the reactions that carbocannons do to get their complete octet are different than the reactions that carbon center radicals do. That's not surprising because carbocannons need two electrons so they carry out reactions that get them two electrons. Carbon center radicals need one electron to complete their octet so they carry out reactions that get one electron. Often those reactions involve stealing whereas reactions of carbocannons often involve sharing. Now the last reactive intermediate is kind of a little bit different than the other two. And I'll draw it in your textbook, draw it as a carb anion. Carb anions have a complete octet on carbon. There are anions, negative charges centered on carbon. The carbon has a lone pair of electrons and a net negative charge. Carb anions you will rarely see as actual carb anions floating around. In general they are simply something we will think of as an alternative structure of an organometallic region. But the reason carb anions in general are unhappy is carbon isn't that electronegative. So there are many things that would better stabilize that negative charge than carbon. Carbon's electronegativity is much less than say oxygen. So in the reaction of the three yard reagent where we have a carbon magnesium bond, magnesium is electropositive, we will often think of our linear reagent as being like CH3 minus mg Br plus in its reactivity. Hence being like a carb anion in its reactivity. And you will learn more about these species and about organolithium reagents later on. Alright, let us finish up by talking about a couple of examples of reactions that are going to set the stage for things that we are talking about later on. So in our reaction of cyanide with ethyl iodide, we have no intermediate. And I will draw the curve-dero mechanism once again just to make this very, very explicit. In a simple process, the cyanide group comes in and we form a bond to carbon and we break a bond to iodine. This is an example of a concerted process, one in which we have gone without an intermediate from a reactant to a product. Let me now show you an example of something that occurs in steps with a reactive intermediate. That reaction, by the way, is called an SN2 reaction. The reaction that I will show you now is an example of an SN1 reaction. Alright, if we take tert-fugnol, if we take 2-methyl, 2-chropanol, and we treat it with HBr and H2O, we treat it with hydrobromide acid. An HBr and H2O dissociates to form H3O plus and bromide anion, and those are going to be the players in this reaction. The product of the reaction is the 2-bromode, the 2-chropane that we saw before tert-fugnol bromide. So this is a substitution reaction. Just as the other example was, we've broken a bond to oxygen and we formed a bond to bromine. How does this reaction occur? This reaction occurs by way of a carbocation intermediate. We're going to be seeing this a couple of times again, so don't worry if this goes by fast today because this particular concept is going to be coming back again and again. In the first step, we protonate the oxygen, and I'm using curved arrows to show the flow of electrons from the lone pair to the hydrogen, breaking a bond between the hydrogen and the oxygen, just like we did on the midterm exam. And now we've formed protonated tert-fugnol. In the next step of the process, and again, don't worry if this goes by fast because we're going to be seeing it a couple of more times. In the next step of the process, we have a protonated OH group. It can leave taking its pair of electrons with us to give us the tert-fugnol cation. Here's our reactive intermediate, the tertiary bugle carbocation. In the final step of this SN1 reaction, our carbocation, which is unhappy because it doesn't have a complete octet of electrons, now undergoes a reaction with bromide anion, which is present in our HBR solution. Bromine, bromide having a pair of electrons is willing to share it, and I draw my curved arrow from the lone pair of electrons on bromide and the carbon atom. And the overall result now is the formation of the new carbon atom. All right, well, next time we're going to be picking up, continuing our theme of discussing reactions. We'll talk about the energetics of reactions, and then we'll go on later in the following lecture and talk about some reaction free energy diagrams that we'll discuss in the next lecture.
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -2:05 Topics -5:40 Writing a Reaction -10:51 Substitution Reaction -13:43 Arrows -14:49 Reaction Arrow -15:55 Equilibrium Arrow -18:39 Curved Arrows -23:03 Fishook Arrows -27:04 Double Headed Arrows -29:58 Addition Reactions -35:28 Elimination Reaction -39:44 Reactive Intermediates -40:45 Carbocations -41:50 Radicals -43:00 Carbanion -44:45 Examples of Reaction Mechanisms
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10.5446/19395 (DOI)
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Good morning. Good morning. So today we're finishing up or hopefully finishing up our discussion of chapter six, understanding organic reactions. And what I'd like to talk about today are some of the specifics of the energetics of reactions. We talked last time in very general terms with energy diagrams talking about whether reactions went in a forward direction or didn't go, whether the products were higher in energy than the reactants or lower. We talked about the relative energies of intermediates and the relative energies of transition states. Today we're going to talk a little bit quantitatively about some of the energies of reactions. In most cases you won't be able to just look at a reaction and tell exactly how many kilocalories per mole of enthalpy it releases. But in certain simple reactions where you're just breaking and making a couple of bonds where there aren't too many, where there aren't ionic species present that have big energies of salvation, we can make some very accurate calculations about the energies of reactions. I'd also, if we have time at the end of the class, like to give you one number that's extremely useful to know, it's 1.36 and I'll put that into some context. But let's start by looking at a very simple reaction, the chlorination of methane and see if we can make some sense of the energy or more specifically the enthalpy of the reaction. So if you take methane, CH4, and you mix it with chlorine, they're both gases and usually this is done in the presence of some heater light, I'll talk more about that in a moment. You can get chloromethane in HCl. And I'd like to take a moment to talk about the energy of this reaction. Now we talked about the broad classes of reactions before and this falls into the class of a substitution reaction. Remember in a substitution reaction you break a bond and you replace it with something else. And so in this particular case we're breaking a bond between a carbon and a hydrogen or more specifically a methyl carbon and a hydrogen. And we're forming a bond between a carbon and a chlorine or more specifically a methyl carbon and a chlorine. So these are the bonds that are being made and broken. And if we can tally up all of the bonds, the energies of all of the bonds that we're making and we're breaking in this reaction, we can figure out the enthalpy of the reaction. Well these are the bonds that are perhaps obvious from an organocentric point of view meaning I'm looking just at the carbon atom which is what I do as an organic chemist. But of course we're also breaking the chlorine-chlorine bond and we're also forming an HCl bond. And so the question that I want to ask is does this reaction take or make energy? And I want to be a little more specific because the one thing that we really can address very well here specifically is enthalpy. We've been a little fast and loose in our energy diagrams between generic energy, enthalpy and free energy. And today I'd like to focus a little bit. So specifically we can focus this question and say is the reaction endothermic? Remember an endothermic reaction is one in which a heat of reaction is positive so I'll put parenthetically delta H0 is positive. Or is the reaction exothermic? And of course that's delta H0 is negative. So really if you can keep in mind that negative means heat given off products lower in energy than the reactants and positive means heat absorbed, then everything I'll talk about can make sense without us having to really look at any equations. In fact there are just two equations I think organic chemists need to know and I'll show you those later on. You've already seen them in general chemistry. So let's imagine for a moment that we're going to go through a series of breaking and making the appropriate bonds. So imagine if you will that we're going to break the methyl hydrogen bond. Now the great thing about this, this process actually occurs but in a slight different order, the great thing about it since we're only interested in the end result that we've broken chlorine-chlorine bond, we've broken a methyl hydrogen bond, we formed a methyl chlorine bond, we formed a hydrogen chlorine bond. It doesn't matter what really occurs in the mechanism of the reaction, all that we need to do is tally up the energy of the bonds and make sure that we've gotten to the right molecules. So imagine for a moment that we break this methyl hydrogen bond and we get CH3 dot. CH3 dot remember is a methyl radical. It's a carbon with an electron in a vacant p orbital, it's trigonal planar, roughly trigonal planar in geometry and you have an electron in a vacant p orbital but it doesn't matter what's happening here. Just imagine because we're going to have a chart and if you've read your chapter 6 we've already seen on page 207, there's a table that gives us lots of bond dissociation energies for specific molecules but there are also archetypes for general bonds where you have say a primary carbon bound to a hydrogen or a secondary carbon bound to a hydrogen or a tertiary carbon bound to a hydrogen. So imagine that we break the methyl hydrogen bond to get a methyl radical in a hydrogen atom. The delta H naught, we're just going to tally up the delta H naughts for all the bonds involved. So the delta H naught for this particular process is the bond dissociation energy. We can refer to that as BDE, it'll make things simpler because we'll be using it a couple of times. I'm just going to abbreviate it as BDE just like I sometimes abbreviate reaction RXN. And we can think of this as the bond strength. This is the energy to literally rip a bond apart. Now I don't know if this is going to work. I wanted to connect things to your textbook and let's see if I can wake up the document camera and give us a table here. If not, I'll just read it off of your textbook for you. Let's see if this works. Well, the good news about technology, the good news about technology foiling me is that I do have a copy of the page in your textbook. So on page 207, it gives a whole bunch of bond dissociation energies. It gives bond dissociation energies for hydrogen halide bonds, HF, HCl, et cetera. It gives all the halogens, the energies to rip their bonds apart. It gives various types of alcohol hydrogen bonds. It gives a methyl hydrogen bond. It gives an ethyl hydrogen bond. It gives an isopropyl hydrogen bond, a secondary bond to hydrogen from the isopropyl group to the hydrogen, various other bonds. It gives carbon carbon bond strengths, carbon halogen bond strengths. You'll have a chance to use this table in your discussion this week and I urge you to bring your textbook to the discussion section. We'll have a problem involving the hydrogenation of ethylene which is going to be very similar to what we're seeing here today. So as I said, table 6.2 page 207 and I already looked it up. The bond dissociation enthalpy for methane is 104 kilocalories per mole. And we're going to use kilocalories per mole in this class. It's a nice way of keeping track of things. All right, I want to do this for some others and then we can tally things up. Let me put this ELMO or whatever they call it away. All right, so four reactions that we have to worry about in this particular thought experiment. We already worried about breaking the methyl hydrogen bond. We said we paid a price of 104 kilocalories per mole. Other bonds that we break, we break the chlorine bond. If you look in your table on page 207, chlorine-chlorine bonds are a lot less strong than carbon-carbon bonds or carbon-hydrogen bonds. This is one of the reasons why chlorine and such a reactive gas bromine and iodine are as well. The bond dissociation enthalpy for the chlorine-chlorine bond is 58 kilocalories per mole. Now, again, thinking about this in a thought process, if we're forming a carbon-chlorine bond, at least formally what we're doing is we're taking a methyl group and a chlorine and bringing them together. The point is now we're looking at the negative of the bond dissociation enthalpy over here. In other words, the bond dissociation enthalpy of a methyl-chlorine bond, again, taken from your table, is 84 kilocalories per mole. But, of course, it's going to be in the opposite sense when we tally everything up. In other words, we're paying the price of 104. We're paying the price of 58. But we're getting a reward of 84 kilocalories per mole because formally we're forming that bond. And then lastly, we're going to be dealing with a hydrogen atom. And again, this doesn't matter whether the reaction occurs with ever seeing free hydrogen atoms. In fact, it does not occur with free hydrogen atoms. But we're forming a hydrogen-chlorine bond. And so we have to think about the energy, the price that we pay for breaking this bond. And then just realize that we reap the reward of that energy when we tally everything up. So the bond dissociation enthalpy here is 103 kilocalories per mole. And now all we have to realize is that the energy of the reaction is the price we pay in bonds broken minus the rewards that we get in bonds made. That makes sense, right? If you form a bond, it makes heat. Negative is good. Enthalpy, negative enthalpy means heat is given off. If you break a bond, you have a positive value. You have to put energy in to break a bond. So let's tally things up for this particular case. We pay a price of 104. We pay a price of 58. And then conversely, we reap a reward of 84. And we reap a reward of 103, all in kilocalories per mole. So the tally on this is negative 25 kilocalories per mole. That's an exothermic reaction. So let's give you a calibration scale. We saw that a kilocalorie per mole wasn't a whole heck of a lot of energy. That was the energy of two methyl groups banging into each other. 100 kilocalories per mole, that's a lot of energy. That's the energy of a bond roughly. 10 kilocalories per mole, that's a reasonably sizable amount of energy and here we're at 25. So this reaction releases a good deal of heat. Now a general rule is exothermic reactions tend to proceed. In most reactions you need some energy to get over energy barriers. In the actual mechanism of this reaction, which you'll learn about later, it's called a free radical halogenation reaction, a free radical coronation reaction. We need enough activation energy to break the weakest bond in the whole gamish. The weakest bond is the chlorine-chlorine bond and that's what gets the reaction started. Most reactions have some type of activation energy and that activation energy can be overcome usually by heat, sometimes by light. Now when I say heat, we have heat in this room and I don't mean just because it's a little warm here today. I mean that some reactions proceed at room temperature because molecules are in motion at room temperature. Some like this reaction need a little bit more heat, a couple of hundred degrees to get it going. Some reactions even will go at negative 78 degrees at the temperature of dry ice. There's still enough heat. Virtually no reactions would proceed at liquid helium temperatures 4 degrees Kelvin, colder than any place on Earth, very cold, but most reactions can get enough energy to overcome activation barriers with heat or with light if they are exothermic. And so let me finish the equation that I had written at the very start just so you have a complete equation for the chlorination of methane. CH3 plus Cl2 goes to, and I'll use the abbreviation delta, heat or H nu, a photon, light right at the cusp of the UV spectrum right at the edge of the visible. Sunlight's a good way of doing this. Goes to chloromethane plus HCl. Some reactions, as you'll see this week, also go with catalysis. And so the hydrogenation of ethylene often is carried out in the presence of a catalyst like palladium or platinum. You'll learn this week about a reaction, actually you won't learn about a reaction that involves potassium cyanide as a catalyst. We ended up putting that one off for a future time. All right. So what good is all of this? Let's take a look at another example, and I'm going to write a perfectly reasonable reaction on the blackboard. As a matter of fact, it's one that you should have been able to predict by analogy. After all, the halogens are pretty similar. Iodine is in many ways related to bromine or chlorine. So let's write the reaction iodine plus methane goes to methyl iodide plus HI. Let's see if we could expect this reaction to occur. And the question we want to ask is simply, is this reaction exothermic? So we're going to do the same thing but a little bit faster. The bond dissociation enthalpy we already saw was 104 kilocalories per mole for the methyl hydrogen bond. If you look in your table on page 207, the iodine bond is really weak. Its bond dissociation enthalpy is 36 kilocalories per mole. If you're watching your wallet, you know that having to pay less is good, right? We'd rather get a textbook for $36 than for $58. So you say you're well on your way to having an exothermic reaction here. But now we look at what we get back when we sell our textbooks. And the methyl iodine bond is worth a lot less than the methyl chlorine bond. The bond dissociation enthalpy is only 56 kilocalories per mole. And the hydrogen iodine bond bond dissociation enthalpy, again from table 6.2 on page 207, is only 71 kilocalories per mole. And so we can go ahead and figure out the enthalpy of this reaction, delta H naught. Now same calculation, 104 plus 36, the amount we've spent, minus 56 minus 71, the amount we've gotten back. And now we're at positive 13 kilocalories per mole. The reaction is endothermic. And endothermic reactions tend not to go. Highly endothermic reactions tend not to proceed. And as I said, 10 kilocalories per mole, 13 kilocalories per mole, that's a good bit. So I can go back to my original equation here and annotate it to ask whether I expected to proceed and the answer is I would draw an X through this arrow. This reaction would tend not to go. All right, the big, the wild card in all of this is that I've been talking about enthalpy rather than free energy. And really, really what we want to be talking about is free energy in the position of equilibria. Because really what I'm asking, every reaction you can at least nominally think of is an equilibrium. The real question is does an equilibrium lie to the left or the right? And in these reactions we're basically here saying, well let's ignore enthalpy. And that's actually a reasonable thing. The position of an equilibrium depends technically on delta G naught. Delta G naught is the free energy of reaction. Now I said there are two equations that one really needs to know for organic chemistry. And the ones you learned in general chemistry, everything else like the addition and breaking of bonds, I mean that's kind of intuitive. Two equations that I think really, really are the heart of any math in organic chemistry. Delta G naught equals delta H naught. Minus T delta S naught. And the T delta S naught, delta S naught is the change in entropy of a reaction. That's that nebulous term of disorder, randomness. We should know for example that if you break a bond, if you go from an iodine molecule to two iodine atoms from one particle to two particles, you've increased disorder. If you brought two things together, two iodine atoms, in general we've increased order. If we decrease order, if we increase entropy, delta S is positive. If we decrease entropy, delta S is negative. All right. So, and typically the value of this term here, the T delta S term is usually for a reaction less than about 10 kilocalories per mole. That's why I was saying by the time we're up at 13 or 25, chances are enthalpy is going to be enough to get away with it. All right. The other equation that one should know in organic chemistry is delta G equals negative RT natural log of K where K is the equilibrium constant. Because as I said, the real question on every reaction is you could at least nominally think of it as an equilibrium. Does the equilibrium lie to the right or to the left? And remember K is equal to the concentration of products with all of their powers. If you have two of a molecule then it would be to the squared over concentration of reactants. This should be old hat from general chemistry. In other words, if I have a reaction of A plus B is an equilibrium with C plus D, K is equal to concentration of C and D, the product of those two concentrations over the concentration of reactants A and D. Pardon? Which are the universal gas constant? Do you mean what value R is equal to 0.001987 kilocalories? Because as I said, I'm a kilocalories kind of person per mole Kelvin. All right. So what are the implications of this? I want to give you one example and then that generality of that number, 1.36 kilocalories per mole that I mentioned before. So let me give you one specific. We talked about the ring flip reaction of cyclohexane and I said that the energy to put a methyl group axial on cyclohexane is 1.8 kilocalories per mole. In other words, cyclohexane, methylcyclohexane exists as an equilibrium mixture of axial and equatorial conformers. Delta G naught for this reaction equals 1.8 kilocalories per mole. And so our equilibrium constant K equals E to the negative 1.8 divided by 0.001987, the gas constant and its product. And we'll say at 298 Kelvin. So I'll say at 298 K that equilibrium constant equals this value that's E to the negative 3.04 or 0.048. In other words, we have a ratio of 1 to 0.048 and that ratio is 21 to 1 just working the math on that at equilibrium. In other words, methylcyclohexane has a dynamic equilibrium between the axial and the equatorial conformer and at equilibrium you have about 5%, just under 5% of the molecules in the axial conformation and about 95 in the equatorial conformation. All right. The one very useful magic number to keep in mind, 1.36 kilocalories per mole. At room temperature at 298 Kelvin, that corresponds to a 10 to 1 ratio. That corresponds to an equilibrium constant of 1 of 10 or 0.1 depending on which value, whether you're positive or negative. In other words, delta G naught equals 1.36 kilocalories per mole leads to K equals 0.1. I just did the math on that but it's a nice number to have in your head because now with nothing more than arithmetic you can use it. If our delta G naught is negative, of course, negative is good, negative means to the right, that's going to lead to K equals 10. And the beauty of exponents and logarithms is now if you double that, your equilibrium constant is going to be 100. In other words, if it's negative 2.72, I've just taken negative 1.36 times 2, that's going to lead to K equals 100. And if our value is negative 4.08 kilocalories per mole, that's just negative 1.36 times 3, that's going to lead to K equals 1,000. So with nothing without a calculator, without anything, you suddenly can come up with a reasonable scale. Oh yeah, 10 kilocalories per mole really does mean an equilibrium lies pretty darn far in one direction or another. A kilocalorie here, a kilocalorie per there means you've got some of both species present. All right, next time we'll pick up talking about chapter 7. Goodnight, bye!
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -1:58 Energetics of Methane Substitution Reaction -8:53 Bond Dissociation Energy -16:24 Calculating Bond Dissociation Energy -17:51 Exothermic Reaction -22:24 Methane and Iodine Example -25:04 Endothermic Reaction -27:00 Free Energy and Equilibria -32:03 Ring Flip of Cyclohexane
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10.5446/19397 (DOI)
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Good morning. Good morning. I am happy. Welcome to a long and very fast journey through eight chapters of a course that focuses on 24 chapters. We come, we review the structure and bonding. We've learned about some organic compounds, functional roots. We've learned about curve arrows and begun to discuss various types of organic reaction mechanisms. And now we're starting to see that organic reaction mechanisms can become complex in their many different pathways that can proceed upon and also bury many different stereochemical issues that come up. We saw this in chapter seven of SN2 displacements. We saw even having to really be cognizant of what happens to a stereochemical center and looking at the quiz problem that we just had with the first problems on SN2 reactions. And now we're going to continue some of these ideas of many fold courses of reactivity in discussing chapter eight, discussing elimination reactions. We're going to talk about two different mechanisms of elimination reactions during the course of this week. We're going to discuss E2 eliminations and then E1 eliminations. And we're going to be learning more about the stereochemical course of these reactions and particularly the requirement that E2 eliminations occur with what's called an anti-curry-cliner relationship. In the second lecture, Wednesday's lecture, we'll be seeing the stereochemical implications of this. The homework in the discussion problems will actually be getting to explore the antithesis of an anti-curry-cliner relationship and a sin-curry-cliner relationship that comes in a very special concerted reaction that you'll be seeing. So there's a lot of me here. We'll be learning about which types of electrophiles, which types of alkyl halides participate in E2 reactions and under one condition and which types participate in E1 reactions. So let's start by looking at a reaction that I talked about or at least alluded to in the discussions of chapter seven, but I didn't really tell you where this reaction went. So let's take tert-butyl bromide and let's envision treating this with sodium anthoxide. The first thing you might think when you see this reaction, you might envision some type of displacement reaction. Perhaps you'd even envision an SN1 displacement reaction. And this is not what occurs. Big X here means that this doesn't occur. So the key is sodium anthoxide. We've talked about bases. We've talked about nucleophiles. Sodium anthoxide is the strong base. PKA is the basicity of the anhydride. It's very similar to the basicity of the hydroxide anhydride. Remember, in all quarter making and analogy between alcohol groups and hydrogen, between the ROH and HOH water functionality, the PK of water associated with water being an acid loss of protons 15.7, and PK of ethanol is very similar. It's about 17. And instead, what happens is an elimination reaction. And the product that we observe is isobutylene. If we want to write a complete set of products from the reaction, then our sodium anthoxide is going to give us ethanol. And we'll also get sodium bromide as an organic byproduct of the reaction. I'll put these in parenthesis because organic chemists are often so focused on one reactant that they'll often ignore other products. But if we're trying to be complete, here are other products. This is called an E2 elimination reaction, or E2 reaction. E2 stands for elimination bimolecular. Just like SN2 stood for substitution nucleophilic bimolecular. SN1 stood for substitution nucleophilic unimolecular. And remember when we looked at substitution reactions, of course, in both an SN1 and an SN2 substitution reaction, ultimately two molecules were involved, the electrophile and the nucleophile. But the big difference between SN2 and SN1 was that in the transition state, in the rate determining step, we had one molecule involved in SN1, two molecules involved in SN2. And this is exactly the case with both the E2 elimination that I'm going to talk about now and the E1 elimination that we'll discuss on Friday. So what's occurring in this reaction is our ethoxide, and I'll write it as ETO minus, and I'll draw in some long pairs so I can kind of push some arrows here, is coming in in the rate determining step and is pulling off a proton at the same time we are spitting out bromide anion. So here's our ethoxide and here's our tert-butyl bromide. I have one methyl group, so I need to draw hydrogens in mice first, and here's a bromide, here are our methyl groups. So in the transition state, we are having the ethoxide come in with a pair of electrons and start to pull off this proton. We're going to push electron density in between the two carbons going from a single bond to a double bond, and we're going to spin out bromide. So as we go through the reaction, and I'm just going to start and arrow here and make the drawing of the transition state. Now I didn't do anything as fancy as old overhead animation or SN2, but this is very much the same process. Ethoxide starts to come in, it starts to form a bond to hydrogen. At the same time we're starting to push electron density between the two carbons, which is starting to push out bromide. Partway through the reaction, we're halfway there, we have our ethoxide, which is now partially bonded to hydrogen. That hydrogen is partially bonded to carbon. We of course have our single bond between carbon, but we're starting to form a double bond. You want to be technical just as we started to change geometry about the carbons in an SN2 reaction, we're starting to change geometry in our E2 reaction. We're going from being tetrahedral to being planar as we progress into the transition state. We're starting to break our bond to bromine. This is my drawing of the transition state. Remember a little double dagger there is what organic chemists often use to symbolize the transition state. I'll draw it out. Two electrons here on the ethoxide. We have part of our negative charge on the ethoxide. We haven't yet formed a full bond to hydrogen. Remember a transition state is that species that exists for a fleeting moment for the length of a vibration per second as the reaction is occurring. We can't go ahead and have this as a stable configuration. It's not an intermediate, it's just that high point as we go over the reaction coordinate that we proceed from reactants to intermediates or intermediate products or in this case directly from reactants to products. So we have a partial negative charge on ethoxide. We have a partial negative charge on bromide. That fleeting moment of the transition state passes as we go through the reaction and now we have our ethanol. We've planarized, is that a word? We've made planar. Our carbon atoms as we've changed hybridization from sp3 to sp2 associated with a double bond. We now have a fully formed kaibond. This is my very head drawing of isobutylene trying to represent it in the plane that's orthogonal to the blackboard with a methyl group coming out and a methyl group coming back and a hydrogen coming out and a hydrogen going back. And finally we have our bromide over here. So those are our products of our reaction. Thoughts or questions about this process? So here's the delta negative charge. So is there to be some positive charge as well? Not necessarily. We started the overall. So the question was there's delta negative charges. Do there need to be delta positive charges? All the charges need to add up to the net charge that we have. We start with a negative charge in the ethoxide. So at all points we've got to have a net negative charge. And so there's delta negative charge on the ethoxide group and the bromobrub in the transition state. Now your point is well taken. We're only catching a little snatch. We're only catching part of the picture in any sort of drawing that we can take. And you're right in that the carbon bromine bond is already polarized. So you're right. So there's a little bit of a delta negative here and a little bit of a delta positive. A little bit of a delta negative on the bromine. A little bit of a delta positive on the carbon which we're overlooking in the process. That's one of the reasons why bromine is so happy to go away. So I'm just showing part of the picture here. But coming back to the question, do we need to have a delta positive when you have a delta negative? Absolutely not. So we're just using that to represent the main parts of the charges. Other questions. That's a good question. Back row. What is the delta charge on the H with two bonds? The negative is a bit of a negative. Would that H with two bonds also have a negative? Probably not here. Probably not any significant negative charge. You can think of it in the transition state really as half a bond to one half a bond to the other. And remember, that's not a stable configuration. That's only occurring transitively. Good question. Other questions. All right, just as we thought about reaction energy diagrams for reactions of the SN1 and SN2 variety, we can think about energy diagrams to help us think our way through an E2 reaction. And later on we'll do this for E1 reaction. So the reaction is downhill in energy. So here's our energy diagram. Here's our reaction coordinate. Remember, the reaction coordinate you can think of as a sort of a time axis as the reaction progresses. Or you can think of it as representing, say, the distance between the adoxy group and the hydrogen. It's just showing the progression of the reaction. The reaction is downhill in energy. In other words, the equilibrium, if you want to even talk about equilibrium for this reaction, lies very far to the right. So I can start our reactions up high in energy, our products down low in energy. I like to go ahead and try to write out all of my reactants and products explicitly in my intermediate. So I know what I'm talking about. So I'll draw a tert butyl bromide on the left. I'll draw an ethoxide on the left to remind us that these are our reactants. For our products I'll draw isobubling and ethanol and bromide. And so in a single step, without the formation of any intermediates, without the formation of any carbocation, we go from reactants, we cross over that energy barrier through our transition state, the high point that we've represented on the blackboard over here, to our products. And since we have two reactants intimately involved in the rate-determining step, our rate law is going to depend on the concentration of both of those reactants. In other words, we'll have bimolecular kinetics. E2 told us we have bimolecular kinetics, just like SN2 tells us we have bimolecular kinetics. In other words, our rate is going to equal rate constant K times the concentration of tert butyl bromide times the concentration of the bimolecular kinetics. And just like in SN2 reaction, if you double the concentration of adoxide, the reaction proceeds twice as fast. And if you double the concentration of E2 reaction, of course, the reaction goes four times as fast. So the whole part of an E2 elimination reaction is you need a strong base to get in the adobt and proton. If you had a very weak base, like iodide, I-, we said it's a pKa of HI, is negative 10, I- is a very weak base. We wouldn't have a species that's able to get in and pull off the proton. But adoxide, pKa of ethanol is 17. Adoxide is 10 to the 27 times stronger base. It's able to get in and pull off that proton. Now we've still seen that there are plenty of issues that come up. We've seen in SN2 reactions and SN4 reactions that we get certain conditions that tend to lead to SN2 and certain conditions that tend to lead to SN1. One of the big issues here for whether we're getting SN2 or E2 is going to be the substitution pattern of the alkyl halide. We might have E2 versus SN2 or E2 elimination versus SN2 substitution or SN2 displacement. So generally, if you take a tertiary alkyl halide, and of course that tertiary alkyl halide has to have some beta protons like we've seen here, a proton that can be pulled off, plus an alkyl oxide. And I'll write this generically as tertiary alkyl halide plus an alkyl oxide. Now we're going to get mainly E2. Tertiary alkyl halides also with alkyl oxide bases and other very strong bases like hydroxide tend to give mainly E2. So in other words, let's say I took, oh, bromo cyclohexane. And let me take a different alkyl oxide base. Let me take potassium tert butoxide. And I'll indicate our solvent. Usually when one works with potassium tert butoxide, one generates it in tert butanol. And so often one uses tert butanol as a solvent. Sometimes as you saw in the last chapter, one can use a dipolar or aaprodic solvent like dimethyl sulfoxide. But if one treats our bromo cyclohexane with potassium tert butoxide, the main product is going to be cyclohexane. Perhaps you will get a very, a very minor amount of the tert butoxide of the SN2 displacement product, cyclohexyl O tert butyl. I'm going to put minor, but I'll put parenthetically very minor. By that I mean that you would get, oh, a few percent of the ether product, a few percent of the SN2 displacement product at best. In general, tertiary, in general, secondary alkyl halides tend to eliminate predominantly mistorm bases. Just to remind us what this means here, I'll draw out the structure. So this is potassium tert butoxide drawn out as a full structure. We call it tert butoxide. I'll write out the name. We call it tert butoxide or tertiary butoxide because it is the species that results from deprotonation of tertiary butanol or t-butanol. Don't answer questions. All right. So we've talked about tertiary halides, talked about secondary halides. Let's take a moment to talk about primary halides. The first question. Ah, we're comparing the E2 to SN2. But what about SN1? Okay, this is a great question because this is where people start to say, wait a second, there are all these matter folds in the bottom. All right. So SN1 reaction, great question. SN1 reaction, tert halides do indeed, tertiary halides like tert-butyl bromide, do indeed ionized. So there is a rate of reaction for ionization before mature tertiary carbocation followed by what's possibly reaction with tert-butanol or tert-butoxide. But the rate of reaction with a strong base of pulling off that beta proton is so much greater that for all intents and purposes we never get a chance to have reaction by way of an SN1 pathway when you have a strong base present. So indeed, that pathway is possible if we didn't have tert-butoxide just like a tert-butanol, you would indeed see an SN1 pathway which would give rise to a substitution product. But once you have that base, it's so much lower in energy to just yank off that proton. Good question. Other questions? All right. Let's look at primary halides. And again, we're really looking here at reaction with alkoxide or other bases of comparable or greater strength. So hydroxide would be comparable in strength. NH2 minus MIN would be stronger in strength. So mainly SN2, but I'm going to put a caveat on that. And that star is just a reminder that we're going to see that even here there's some complexity. So let's start with a simple case. We'll take bromopropane. And again, we'll use sodium ethoxide, let's say, inethanol. So the main product of this reaction is going to be our SN displacement product. You'll also get a little bit, so I'll write SN2 here, and I'll write major. We'll also get a little bit of the E2 elimination product, so I'll write E2 and minor here. Now chemists know this from actual experiment. I'm not just pulling these numbers out of thin air or making this up. This is what people in the 1930s and 40s investigated experimentally to learn about. And so when this was investigated it was found that there was a 90% conversion to the SN2 displacement product and a 10% conversion to the E2 product. You wouldn't know that. You wouldn't have to know that. You don't have to know those exact numbers, but this helps us see some trends. So we sort of tear on the edge of an equilibrium. And I've tried to give us a feeling for energetics in equilibria. A 10 to 1 ratio corresponds at room temperature to a 1.36 kilocalorie per mole energy difference. That's not a big difference in energy. And some factors can tip the balance in going one way versus going the other way. And so even something as simple as steric hindrance can make a difference and push things into the E2 pathway. Specifically, if we go and we have beta substituents, this makes it very hard, makes it, let us say, harder for the nucleophile to get in close for that trigonal bond. For that trigonal bifuraminal transition state associated with an SN2 displacement reaction. Remember when I projected the reaction up there, projected the transition state, how crowded it was, how everything had to get in close. Even a nearby substituent that's in the way can help block things and make it more difficult. So if I add a beta methyl group, this isn't a methyl group on the carbon with the halide. I've been alphabet. That would take us from primary to secondary. But if I add a beta methyl group, just the spectator here, that extra steric bulk in going from a simple chain to a branch chain makes it more difficult for the nucleophile to come in. And the result is that it favors E2 elimination. Just a little bit. So if I take, instead of our bromocropate, our isopropyl, our isobutyl bromide, and again I treat it with sodium, methoxide, and ethanol. And just for the sake of variety, I'll remind us that there are many ways to write this reaction. This time I'll write the reaction over the arrow. Now we also get a mixture of SN2 displacement and E2 elimination. But now the E2 elimination predominates. So we get a mixture of the ether and the alkene, and that mixture is a 38 to 62% mixture. In other words, we've switched from the elimination pathway being the minor pathway to the elimination pathway being the major pathway. Not only does steric hindrance of the electrophile affect the pathways, but also steric hindrance of the base affects the pathways. So a bulkier base leads to more elimination as well. And so I'll keep our same electrophile in this comparison. I'll keep our same alkyl halide. But now instead of having sodium ethoxide and ethanol, I'll switch to potassium tertbutoxide. In tertbutanol, tertbutanol makes the alkoxybrom a little bit more sterically hindered. It also makes it a little harder to salvate, a little bit more basic. PK, or tertbutanol, usually people use a number about 18 instead of say 17 for ethanol. And as a result of the greater steric hindrance and the greater base isamine, it's harder, even harder, for the nucleophile to get in and do an SN2 displacement. And it's more favored to have the beta proton hold off. So now our ratio of SN2 displacement to E2 elimination goes all the way up to 8 to 92. In other words, now we've switched from 38 to 62 to 8 to 92. We've really pushed the reaction. And this is good, because organic chemists like to be able to control which way a reaction goes. And this begins to show us how an organic chemist can choose conditions that favor either an alkane product or an alkene product or an ether product. Last point I want to make, just on the generation of alkoxide bases, just because it's useful to know where they come from and why they can be used in the same alcohol. In general, if you take an alcohol plus sodium or potassium, the metal, the alkali metal will react to give the corresponding alkoxide plus hydrogen gas. And you know if you throw sodium into water, it catches fire. You know if you throw potassium into water, it explodes. So organic chemists often choose their metal carefully. They'll use sodium for more sterically unhingered alcohol, like methanol or ethanol. Because nobody wants to have their laboratory catch fire. And they'll use potassium for more sterically hindered alcohols that react slowly like tributanol. And that's one of the reasons why I've been switching around from sodium to potassium.
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -3:03 Tert-Butyl Bromide Example -5:49 E2 Reaction -7:23 E2 Mechanism -14:50 Energy Diagram for E2 -17:27 Rate Law for E2 -20:13 E2 vs SN2 -27:03 Primary Halides -29:59 Steric Hindrance
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10.5446/19396 (DOI)
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Good morning. So, what we're going to do in today's lecture is to begin discussing alcohol halides. And this actually is now going to be something that will continue for the remaining seven lectures of the class, where we're going to be looking into and trying to understand the varied reactivity of alcohol halides. So, what we'll do today is to start looking at how we name them and, more importantly, how we name them. Really what the anatomy is of different alcohol halides. Then we're going to return to those stupidly affilling substitution reactions that we used in some previous examples and start discovering some reactions. Try to understand a little bit more about their mechanism and their anatomy, what the various components are and what's going on in them. And then we're going to look at being in time at some analogous examples. And then over the remaining lectures of the class, we're going to start looking into varied reactivity patterns as you change the structure of alcohol halide. And also some of the really exciting stereochemical limitations on this. So let's begin by talking about the nomenclature of alcohol halides. The good news about this is it's really very similar to the nomenclature of alkane. You simply name them as the yellow alkane. And I'll show you what I mean. So basically, just as we learned that you can have on the quiz a methyl substituent or an isopropyl substituent on an alkyl chain, as we had in our example of isopropyl methyldexane, you can have various halogen substituents, chlorine, bromine, chlorine, and iodine on an alkyl chain. So let's just take a couple of examples of this. So you're going to name them as the yellow alkane. You'll number and alphabetize the substituents. So you're going to number and alphabetize, and of course you'll be alphabetizing under fluorofluoroflomerol. If you look at your periodic table, you'll see there's one more element that falls into the halogen family, one that we absolutely never see in alcohol halogens. What is that? A.T. What is that? Acetine. It's radioactive. There are no stable isotopes of it. And organic chemists, although we actually like to play with molecules that are radioactive, for example, radioactive carbon is used in drugs for PET scans. Nobody, to my knowledge, has yet found any application of S-Betide in any sort of organic compound. It probably means that your generation should be going to do it. Anyway, we'll concern ourselves with chlorine, chlorine, bromine, and iodine, and then you number these and alphabetize them along with the alkyl substituents. In other words, as far as the nomenclature goes, there's nothing special about it. I'll just take a couple of examples here. We'll see what I mean. Just a few simple ones. And as I've indicated before, although there's certainly entire books that can be written on nomenclature, I think beyond the basics, beyond getting the gist of picking the substituents, picking the main chain and alphabetizing, and knowing a few of the substituents that we saw like isopropyl and termed udal, I think it really gets to be an exercise in fertility. So this compound here, we would say, okay, we have a 5-carbon chain. We have a bromine substituent. We're going to number the chain from either direction, but we're going to number this chain to put the bromine at the lowest position. In other words, we're going to know where the 1, 2, 3, 4, 5. This compound is 1-romocentane. And if the bromine were at the second position, we'd call it 2-romocentane. Another example. So this compound, you pick the longest chain. Well, no matter how you slice it, the longest chain is going to be 3-carbons. It doesn't matter whether you number it this way, or whether you number it this way, or whether you number it this way. And the substituents on the chain are going to be a chlorine and a methyl group. Both at the 2 position. So the compound is going to be 2-chloro-2-methylchropane. And as is often the case, many compounds have common names, trivial names that sometimes are so likely used that they are the things that really will roll off the tongue of a practicing remanedic chemist. When I write out these names, I'll try to remember to put them in parentheses just to make a distinction for your notes. So this one, what would roll off of most of our compounds would be tert-butyl chloride. So this one would be tert-butyl chloride. Take one more example, and I'll give us a cyclic example with some stereochemistry just to remind us, bring back some concepts of stereochemistry. This one also gives us some of our nomenclature substituents. Okay, so we made this compound as a cyclohexane ring. You have an iodine on the ring. You have a tert-butyl group. Remember, if you're numbering and everything else is equal, you're just going to number the dip that will always come into the first substation. In other words, here we honestly could number either 1, 2, 3, 4 or 1, 2, 3, 4. Everything else is equal because it's not the first substituent, are they changed? And in this case, since butyl becomes before Iodo, we'll number this as 1, 2, 3, 4. And so this compound becomes 1-tert-butyl, 1, 4-Iodo cyclohexane. And more specifically, we indicate the stereochemistry. This one, first use, 1-Iodo. All right, what's much more important than how we name these compounds is really how we think about them. And what we're going to see as we go through and look at SN1 substitution reactions and SN2 substitution reactions and E1 elimination reactions and E2 elimination reactions is that we need to understand the anatomy of them. Whoops. Yes. Thank you. Always a sharp pair of eyes. Always very funny. All right. As I was saying, what's much more important is really figuring out the anatomy of these compounds. And so I'm going to spend a few blackboard panels actually writing out some different alkyl halogen. Because the first thing you'd look, oh yeah, it's just a compound with some halogen on it. So let's look at some anatomy here. And one should become good enough at visualizing this that we really see this right away that you don't have to go to any sort of rulebook that basically just comes to your mind right away. So that's why I'm going to go slow. All right. So CH3, CH2i, the one we used in our example of an SN2 displacement reaction with cyanide. Obviously it's an iodoalkane, but what's much more important about this is that it's a primary iodoalkane. So I'll write its name just to remind us iodoalkane. No need to number because no matter where you put the iodine on the ethane, it's always going to be at the one position if you don't put anything else in. But much more important, the iodine is attached to a primary carbon. Remember, a primary carbon is one with one other carbon attached to it. So we often abbreviate this one-nought alkyl halide. The general structure, if you're looking for sort of a general structure, what's going to clue you in that you have a primary alkyl halide? It's going to be that you have whatever your chain is, whatever your R group is here. We'll see various examples. Bound to the CH2 group, bound to a halogen. And again, that halogen could be fluorine, bromine, fluorine, or iodine. Chloro compounds actually react a little bit differently than bromocloro and iodo compounds. There are a lot of reactions that chloro, bromo, and iodo compounds take part in, that chloro compounds don't. And when we come to our discussion of leaving groups and relate this concept to pKa's of the conjugate acid, remember we said HF was a very weak acid compared to HClHBr and HI. We'll see the differences in reactivity. Anyway, right now what I want us to do is just to focus on the fact that we have a methylene group, a CH2 group, connected to our halogen and see that aspect of the anatomy. And let's contrast this with the other one that we took, pH3 CBr. pH was that shorthand that we used for phenyl, so it was 3-bin Z-brings. I wrote this out in the form and I'll write it out again if you have it in your notes. Don't bother to re-transcribe it, just to remind us since we do get a few abbreviations. Alright, so when you look at this, it takes a moment to make sense. We have a carbon with three other carbons attached to it and so that's a tertiary carbon. And so this is a tertiary alkyl halide. So I'll write out the name, Romo-Triphenylmethane. If I had more space, I wouldn't be using a hyphen, I'd run the triphenyl directly into methane. And I'll point out that it's a tertiary alkyl halide. And the general structure that's going to cool us in to something being a tertiary alkyl halide is we have a carbon with three other carbons attached. So I'll write this in shorthand as R3CX. So, R3CX is a tertiary alkyl halide. We have a carbon and a carbon with three other carbons attached, All right. Let's take a look at a couple more examples and then we'll get the catalog of all of our types of alcohol halides that you'll see for the basic ones. And then I want to draw some really important contrasts. All right. Let's take this one. This is chlorocyclohexane. No need for a number on it, just like methylcyclohexane. There's only one. You just have a chlorine no matter where you put it. So we always buy definition at the one position. Chlorocyclohexane is a secondary alcohol halide. And what closed us into it being a secondary alcohol halide, what makes it a secondary alcohol halide, is the chlorine's attached to a secondary carbon. In other words, a carbon with two other carbons attached to it. If I wanted to write a generic structure, I could write it as R2CHX, and that would be a generic one, again, with any of your technical villages. We're going to see that all of these classes that we're looking at have very different reactivities, and the reason we're spending this time is so that we see the anatomy, because these are going to tie into the patterns of reactivity that the compounds undergo. Tertiary alcohol halides tend to undergo SN1 reactions and E1 reactions. Primary alcohol halides tend to undergo SN2 reactions and E2 reactions. Don't worry about getting that down right now, we're going to come back to that. The last one in this sort of general categories of alcohol halides are the methyl halides. So if we take CH3I, iodomethane, and here's one where I'll write the common name, because probably off of Johnny's tongue or Buck's tongue in the laboratory, they would refer to it as methyl iodide. As a matter of fact, you probably see that on the bottle in the laboratory as well. And so for our methyl iodide, this is a little special. It's not a primary alcohol halide, it's actually a methyl halide. And we'll learn that they fall into their own special category, their extra reactive in SN2 reactions. In general structure, CH3X, for all intensive purposes, there are just three or four of them, and you're probably never going to see that. All right, what I'd like to do now is to show you a couple of what I'll call special types of halides. And the reason I'm drawing emphasis to this is this is where students often get confused. So I'll put this into emphasis. Because it's very easy to look at some of these and get mixed up in what's going on. So let's suppose we have a halogen on a benzene ring. Let's take this with a bromine. This is bromobenzene. All right, this isn't an alcohol halide. Benzene isn't an alcohol group, it's an aromatic group. And the reason I'm telling you is not that I want a gotcha for you, but nature has made this gotcha where phenyl halides are completely different in their reactivity than all of the alcohol halides. And there are a lot of reasons for this, you're going to learn about it later. One of the reasons for this is all of the SN2 reactions involve a nucleophile getting in behind the halogen. And that can't happen. But more important, it's an issue of hybridization. We're using an SP2 hybrid bond to make a bond to the bromine here, not an SP3 hybrid orbital to make a bond to the bromine. And the bond is much stronger, the hybridization is different, and the reactions occur in a very different fashion. So this is a phenyl halide. It's not, and how big can I write the word not secondary? Or tertiary, you might look and say, well, I see two carbons bound to it, it's a, two, it must be secondary, or I see a double bond here, or you learn to count that as two carbons and conning ol' prelog. But it's just not, it's not an alkyl halide, it's not secondary, it's not tertiary. And again, I'm just going to write a big fat not over here. It doesn't react like an alkyl halide. Alright, one more of our nature again makes very different rules of reactivity. Where all the simple stuff that you see for primary halides or secondary halides simply doesn't apply. And again, I'm just doing this as an example. Any example of a halogen bound to any sort of double bond, or for that matter I might add a triple bond, doesn't react in the same way. This compound is called chloroethene. This ENA on the end comes from nomenclature of alkynes. You're going to learn more about that nomenclature when you come to alkynes. Again, Buck or Johnny probably wouldn't refer to this compound by this name, often with small compounds. Common names, trivial names become more widely used. I'll put the common name vinyl chloride. Give parenthesis. Ever heard that name before? Final chloride, heard it with something in front of it. Polyvinyl chloride PVC pipe. So this is the monomer. So many, many compounds that you encounter in your day to day life are made up of simple chemicals that you're seeing. Polyethylene is actually a polymer of ethylene that in the polymerization process makes it into a great big long alkane. Linear or branched, depending on whether it's high density or low density polyethylene. But basically little monomer units connected together. And this vinyl chloride is the monomer that gets polymerized together to make PVC. Alright, this, like chlorobenzene or bromobenzene, is not an alkyl halide. It's a vinyl halide. Final is the common name for double bonds, the trivial name, and you'd probably refer to them generically as a vinyl halide. So it's not primary. And again, I'll write the biggest bold as not, I can. Not primary, not secondary. It's just not an alkyl halide. And again, just like the case of bromobenzene, it doesn't react like an alkyl halide. Alright, and this is really about seeing the anatomy of these molecules. They're not bound not to an sp3 carbon, but to an sp2 hybridized element. And as I've indicated before, since chemis always like when confronted with rules that nature provides, chemis always like to poke and product those rules. And if chemis have a D tried to check and poke and product, can we make this compound? Can we make a vinyl halide react like an alkyl halide? And for the most part, the answer really is no, they simply don't want to take part in a syntin2 redaction. Alright, now, also to avoid some confusion while we're talking about what I'll call a special type of halide. Two that might confuse you. So I want to get them up here explicitly. Let's take this one. Is this an alkyl halide? Yes. Why? It's attached to a alkyl. Alkyl, our primary carbon. Yeah, this is an alkyl halide. It's a primary alkyl halide. And its reactivity is actually very much like this. So this compound, I won't even write out the non-trivial name. I'm going to write the trivial name. Fennel bromide. So this is primary because we have a CH2 group, so it's an sp3 hybrid. That's telling us it is an alkyl halide. So this is RCH2X. So this is a primary alkyl halide. And the only thing that's special about it is it's what we would call benzylic. And what that means for various reasons is it's actually a little bit extra reactive. In SN2, and depending on the substitution pattern, SN1, or even E2 elimination reactions, this one can't undergo any elimination because there are no beta-hyvergents, but we'll get examples later on where there are. Anyway, the main thing, if none of that makes sense to you right now, the main thing is to recognize that there's a profound difference in structure between bromobenzene and benzoyl bromide. One of them is an alkyl halide, the other one is not. And I'll give you one more example that falls into the same category. And again, for the sake of simplicity, I'm just going to give you the trivial name on this. Allyl iodide. And of course, one of the reasons why I want us to notice the trivial name is this is actually an archetype here. So in general, this class where you have a halogen 1 over from a benzene ring on an alkyl carbon that's connected to it would be called a benzylic halide. And this one we would call an olylic halide. So this is a primary alkyl halide for just the same reasons. And what makes it a little bit special is it's an olylic halide. That means that the halogen is not on a double bond, that would be a vinyl halide, but is on an alkyl carbon 1 over from a double bond. And just like a benzylic halide, it's a little bit extra reactive. What the implications are of this as we go through SN2 and SN1 and E2 and E1 reactions, what the implications are is that reactive ones and extra reactive ones are going to take part in reaction with reagents that we're going to see, nucleophiles and bases. Whereas ones like bromobenzene and chloro, vinyl chloride are not going to react at all with these reagents under normal conditions. It didn't get me on the head. All right, where do I go? All right, let's now, because I've been talking about reactivity and we've been creeping around this issue for a while in our discussion of Chapter 6. Let's revisit the two reactions that we talked about in Chapter 6. These are nucleophilic substitution reactions. And then what we're going to do is generalize these to look at other examples of alkyl halides and other nucleophiles. But let's start with the two examples that I had written out before. So the two examples that I wrote for iodoethane reacting with cyanide and ion, I'll write it with the negative charge on the carbon, giving us propionitrile plus iodide. And the related example that I wrote of triphenylmethyl, bromotriphenylmethane reacting with cyanide and ion, giving us the corresponding nitrile plus bromide. These are both substitution reactions. And of course by substitution, I mean that one group is replacing another. In both of these examples, cyanide is replacing a halide. Now let's take a moment then to talk about the anatomy of the two components in this reaction. In both of these reactions, the component that's doing the substituting, the compound component that's coming in, we refer to as a nucleophile. The cyanide in these examples is a nucleophile. Nucleophile is something that has electrons that it wants to share. It's a Lewis base. It's something that likes a nucleus, a positive charge, hence it has electrons and it has the negative charge that it wants to share. And it doesn't have to have a negative charge. Just like we saw Lewis bases that had a negative charge on them, but we also saw Lewis bases that had no charge on them, all a nucleophile has to do is be willing to share its electrons. Now conversely, these components that like the electrons, we're going to call electrophiles. Electrophile is what we learned as a Lewis acid. This is why when we started discussing acids and bases, I said taking this organic flavor and looking at the reactions of organic compounds made so much sense in differentiating ourselves from general chemistry because there is this much broader principle of reactivity that so many organic reactions involve the reaction of a species that has electrons where the species that wants electrons. And of course the formation of bonds involves simply the sharing of the pair of electrons. Alright, one more piece of anatomy. The iodine, the bromine we refer to as a leaving group, and I would typically refer to them as a leaving group both after they've left but also before they've left. So alright, leaving group. And again to come back to this really important distinction because we've just seen a whole bunch of different drawings of different halons, both alkyl halons and non-alkyl halons. To refocus this, the common feature in all of these substitution reactions is that the carbon that's getting substituted at is an sp3 hybridized carbon. So, that's a very important distinction. So, the carbon that's getting substituted at is a hybridized carbon. So, the carbon that's getting substituted at is a hybridized carbon. So, the hybridized carbon is a hybridized carbon. So, the hybridized carbon is a hybridized carbon. Alright, so, here I've reminded us of all of the things that these two reactions have in common. Now what I want to do is focus on the differences. And the big difference is that the electrophile in the first example, the iodoethane, is a primary alkyl halide. And the electrophile in the second example, the bromotryphenylmethane, is a tertiary halide. So, the first reaction, as we saw because we use these when we discuss mechanism, is occurring in an SN2 reaction manifold. And I mentioned that term but I didn't write it out on the blackboard before. I just showed us the differences in reaction. In SN2 reaction, SN2 stands for substitution nucleophilic bimolecular. An SN2 reaction, as we saw before, is a concerted reaction. The mechanism involves the cyanide, the nucleophiles. Now, draw in one little pair on the cyanide. Coming in, remember electrons flow from the nucleophile to the atom. We break the bond, we put electrons back on the atom. So, the reaction involves two molecules coming together in a concerted fashion. It occurs in a single step with no intermediate. And we saw before that as the atoms come together, as the cyanide approaches the ethyl iodide, we go through a trigonal bipyramidal transition state. Remember, the transition state is that fleeting arrangement of atoms that exist for only about a femtosecond, for only about 10 to the minus 15 seconds, where one atom is coming in, forming a bond, the nucleophile is coming in, and forming a bond, it's pushing out, it's substituting for the leaving group, and that bond is breaking. The carbon at the reaction center, in this case the primary carbon, has gone from being tetrahedral to being trigonal planar. I've drawn it so that the carbon is lying in the plane of the blackboard with a hydrogen coming out. We're starting to form our bond to cyanide. We're starting to break our bond to iodine. We have part of our negative charge in cyanide, part of our negative charge in iodine. And I'll just bracket this and use our little double dagger symbol to remind us that this is a transition state. And we saw in our discussion of chapter 6 that there were kinetic implications of this. In the rate determining step, two molecules are coming together. And so the rate law for this reaction is that the rate is equal to the product of the concentration of those two reactants. The concentration of the concentration of cyanide and the concentration of cyanide double the concentration of either of those, the reaction goes twice as fast. Double the concentration of both of them and the reaction goes four times as fast. And this transition state is really cool. We're going to see all sorts of stereochemical implications as we go on in our discussion of SN2 reactions. All right. The second example is an SN1 reaction. SN1 stands for substitution nucleophilic unimolecular. And we've already seen the mechanism for this reaction. And the reaction goes in two steps by way of a carbocation intermediate. Remember in the first step the halogen leaves, we get a triphenyl methyl carbocation. So here's our first step, pH3 CBR. And the bromine leaves, it takes its pair of electrons with us. I'll give us just a little abbreviated drawing of the mechanism there showing the arrow going on to the bromine. In the second step our cyanide comes in. Cyanide is a nucleophile that has electrons to share. And if you don't know what wants the electrons, the carbocation is unhappy. You have a carbon that only has six electrons around it and it wants eight. So cyanide comes in. And again I'll give you an abbreviated mechanism just showing our cyanide coming in. We're going to bond to the carbon and be good about that cyanide coming in and reacting to form our new bond. And as I said the important feature of this reaction is the first step is the rate determining step. We saw this before when we discussed the kinetics. That means that step occurs slowly as soon as you form the carbocation it finds a nucleophile and very rapidly collapses down to a new stable compound. It's all right fast. So whereas an SN2 reaction showed bimolecular kinetics, an SN1 reaction shows unimolecular kinetics. In other words the rate of reaction is equal to k times the concentration of ROMO triphenyl and the concentration of ROMO triphenyl. So that's the rate of reaction. All right. Thoughts and questions at this point? SN1. Great question. SN1 is it always going to go by a carbocation intermediate? Every example of an SN1 reaction that I can think of will go by way of a carbocation intermediate. Other questions? All right. This is a great point for us to stop. We will pick up next time talking about samples of these reactions, examples of SN2 and SN1 reactions.
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -1:31 Nomenclature of Alkyl Halides -4:43 1-Bromopentane Example -5:49 2-chloro-2-methylpropane Example -7:19 1-tert-butyl-4-iodocyclohexane Example -9:58 Types of Alkyl Halides -15:27 Chlorocyclohexane Example -17:19 Methyl Halide Example -19:09 Special Halides -26:55 Distinguishing Alkyl Halides -32:33 Nucleophilic Substitution Reactions -39:43 SN2 -44:52 SN1
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10.5446/21554 (DOI)
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What is organic chemistry? Chemistry that deals with carbon. And sometimes there are some subtleties and maybe having some CH bonds or maybe things like carbon dioxide at least are excluded. But fundamentally, organic chemistry is the chemistry of carbon compounds. And up until the beginning of the 19th century, people thought that there was an inexorable divide between organic chemistry and inorganic chemistry. That only living things could make organic chemicals. And in 1828, Friedrich Voller broke this paradigm and showed that he could make urea not from kidneys, not from a human being or a dog, but in the laboratory from inorganic chemicals. And that was a major paradigm shift. And then chemical industry later on in the 19th century took off with the dye stuff industry. It used to be that all of the dyes for clothing could only come from plant sources and animal sources like shells and beetles. And then it was discovered that all of these beautiful chemicals could be made in the, where all of these beautiful pigments could be made in the laboratory. And now all of these wonderful purples and pigs and reds and so forth that we take are granted are relatively cheap synthetic chemicals. Health has always been an important part of organic chemistry. And in fact, the dye stuff industry came from a chemist attempt, very crude attempt, a chemist named Perkin to make a chemical compound that was used to treat malaria, quinine. Malaria was a big problem throughout the world. It still is in many parts of the developing world, not in the U.S. right now, thank goodness. But quinine was the only treatment and that came from the bark of a plant. And so Perkin tried to make quinine in the laboratory and instead got a beautiful purple compound and being clever he realized sometimes when you do an experiment and you don't get the result that you see, you could actually do even better with the discovery that you found and thus the dye stuff industry was born. Health has continued with antibiotics, with compounds to treat diseases like AIDS and these are all products of the chemical industry. In fact, many of the PhD students who come through our program like Johnny and Buck will go on to careers in the pharmaceutical industry helping to invent the next generation of medicines that find disease. So I've mentioned some organic chemicals. I've mentioned urea. I've mentioned dyes. I've mentioned antibiotics. I've mentioned drugs to find other diseases. What are some other organic chemicals? Alcohol, a great favorite. Later on you will be learning about NMR spectroscopy and the first NMR not in our class but in the course and the first NMR spectrum nuclear magnetic resonance spectrum, the technique that now is very similar to the medical technique you've heard of as MRI magnetic resonance imaging. The very first nuclear magnetic resonance spectrum was recorded on ethyl alcohol. What are some others? Ethane. We will be learning about ethane and other alkanes, methane, ethane, propane, butane, pentane, hexane, heptane, octane, dodecane, dodecane, undecane, etc. When we start talking about alkanes, which I think is going to be either in October, I believe it may be into November, that will provide us into a platform on some of the big concepts I'm going to be talking about some other organic chemicals. Sugar. Sugar, fantastic. Only sugar is sweet but it is an important component of many living systems. On the surface of cells in your body there are sugars that are attached. Different types of sugars make you, you literally. So in your blood group, whether you're A or B or O, you're going to have different types of sugars attached to your cell surfaces. And in turn, your immune system is going to recognize whether you have sugars for the A blood group or the B group, which is why if you're A you can't get a transfusion from B and if you're B you can't get a transfusion from A. Sugars are also an important part of another biological molecule that is literally central to life, central to your genetic identity. What is that organic chemical compound? DNA. All right. Sugars, nucleic acids, DNA and RNA are two of the biggies for biomolecules. What's the third biggie? Proteins. So everything from synthetic compounds like antibiotics to alcohols to useful things like natural gas and all of the things that derive from petroleum, which includes the plastic and many of the fabrics in your chairs, your nylon backpacks and so forth are all coming from petroleum to biomolecules like sugars and DNA nucleic acids and peptides and proteins are all central to organic chemistry. And this is why even if you are into chemists it is so important to learn a little bit about organic chemistry. Well today I'm going to give you the three things that you need to know for the entire semester of the year, then you can take all your final exams and graduate. So maybe I'm exaggerating a little bit. This will at least give you the cocktail conversation of the three things that you will need to know, but seriously, three concepts that are going to come up and actually be central throughout all three quarters and we will touch on them all this quarter. Stereochemistry, the three dimensional structure of molecules, the three dimensional arrangement of atoms in space. This is where organic chemistry gets fun. We're completely different than general chemistry. That's why we actually get to play with these molecular models because there is very little other than a tangible molecular model that you can rotate and manipulate that can get things into your brain so well. I work with some very big molecules and sometimes it's not practical for me to make a plastic model, so I use computer based models. But to get it really into my brain I'll put on 3D glasses so I can see it in 3D because nothing replaces that three dimensional relationship of being able to rotate and manipulate and so forth. And we will use our plastic molecular models to help us learn about this, to learn about the shapes of molecules and so forth. Second big concept of organic chemistry is functional groups. These are small collections of atoms that have specific properties. So for example alcohol which commonly refers to ethyl alcohol has very similar properties to methanol, methyl alcohol and isopropanol, isopropyl alcohol because they all contain the hydroxy functional group. This group of an OH imparts very similar properties to the molecule. This is a powerful concept because it means if you can predict or if you know the properties of one molecule with a functional group you can predict properties of other molecules with that functional group. Chemical properties and physical properties. Ethanol is much higher boiling than say propane because the alcohol group's hydrogen bond together, it's also much higher boiling than ethane. It's a propane because it's roughly the same number of atoms. Methanol also has a higher boiling point. Ethanol mixes with water, methanol mixes with water. We will learn about functional groups throughout the three quarters like carboxylic acids, ketones, aldehydes, carbonyl functional groups and so forth. We will see that one molecule knowing the behavior of the functional group can allow you to predict and understand the properties of many, many different molecules. And so that is why this is such an important concept. This is different in general chemistry because we are seeing more in the way of patterns and this is where organic chemistry really opens up to people where they say, well I didn't really like all that calculator stuff in the logs and the various equations and the Nernst equation and so forth in general chemistry. And they get turned on when they see these patterns in organic chemistry. The last big concept is Kerbero notation. Reactivity of organic chemicals is all about flow of electrons. And if you understand where the electrons are and what wants to get electrons, who has the electrons and who wants the electrons, these are properties of functional groups, then you can figure out how different molecules react. And Kerberos are ways that we show the flow of electrons that in turn shows us where bonds form because when you share a pair of electrons, you form a covalent bond. When you take away a pair of electrons, you break a covalent bond. And so we are going to use a very simple notation like so to show electrons flowing from something that has electrons to something that wants electrons.
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This course covers topics such as bonding and structures, acids and bases, organic molecules and functional groups, alkanes, stereochemistry, organic reactions, alkyl halides and nucleophilic substitution, alkyl halides and elimination reactions, and other various topics.
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10.5446/21555 (DOI)
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Good morning. Good morning. Good morning. Good morning. So last time we started to introduce the idea of all of these various foam shoulders and begin with the discussive structures of organic compounds. We're going to continue on that theme today and we're going to take our way through some more functional groups and then we'll wrap up on Friday looking at some more functional groups and perhaps we add to the debate. We talked about alcohols last time that contained a hydroxy functional group and we talked about alkane that don't really contain any functional groups. Let me talk briefly about alkenes and alkynes and aromatic compounds. So alkenes, like alkenes, are hydrocarbons but they're hydrocarbons that contain carbon-carbon double bonds. Alkenes contain carbon-carbon triple bonds. And as we were talking about structure and bonding and thinking about some pi bonds and signal bonds, we already got to see some simple alkenes and alkynes. We saw for example ethylene CH2 double bonded to a CH2. We said a molecule is a planar and has a pi bond between the carbons. Ethylene technically is a trivial name for the molecule. Technically although I don't think you'd hear anyone that haven't rolled off their tongue, technically the unpacking, the systematic thing for this molecule is ethylene. Often the very, very smallest compounds, compounds containing one and two and sometimes three carbon atoms, the trivial names have taken over and just ended up getting used almost completely. But then for bigger compounds, systematic names end up being the ones that are typically used. So for example this molecule CH2 double bond CH and then another CH2, CH3. This molecule most people would refer to as one butene. You'll get more on the systematic names of these compounds as we go into the chapters that are detailed. And what we should be doing right now is just hearing the names and letting them wash over you and becoming familiar. So these are two alkene and then if you want an example of an alkyne, we talked before about acetylene. The CH triple bond into a CH and again the systematic name for this compound would be a little bit different. It would be ethylene and again normally you wouldn't end up saying this. Well, alkanes are pretty inert. They don't react with much of anything. On the other hand, alkanes and alkynes are more reactive. For example, they react with bromine. You're going to learn more about the reactivity of these compounds as you go into the chapters that deal with them. But I'll just show you an example of one reaction right now. So let's take our one butene and see how it reacts with bromine. Bromine is a halogen and the way you can tell that a reaction has occurred with bromine is very simple. Bromine is a red, dark red, blood red, fuming liquid that has these red brown fumes over it. If you drip bromine or a solution of bromine in an inert solvent like carbon tetrachloride into an alkene, the color goes away instantly and that's the chemical reaction. So immediately you can tell that one butene or another alkene has reacted with bromine because you get a colorless solution. And so for example, one butene would react to form one-two di-virgo mutane. I'll write out the name and again, don't sweat right now about the days you're going to see more later on. Now by contrast, alkanes don't react with halogens. They don't react with much of anything except under special conditions. So if I simply mix ethane, which is a gas with bromine or bromine vapors, you don't get a reaction under ordinary conditions but there's a big caveat. And that is if you have an energy source, if you have light that has some UV in it or some violet light, or you have a gas-muting source, you keep the reaction mixture up, then you get a reaction to give bromine ethane. And so the big difference is if I take an alkene and I drip in bromine or a solution of bromine and carbon tet, that's where I thread, the color goes away right away. If I take an alkane like hexane and I add bromine, you see no change in the color. All right, another class of hydrocarbons, unsaturated hydrocarbons, are aromatic compounds. You'll learn more about aromaticity later on in the, I think in the V-course or possibly the C-course, but generally not only, aromatic hydrocarbons contain benzene rays. So let me give you a few examples of aromatic hydrocarbons. It contains benzene itself. Of course, it contains benzene rays, it's an aromatic hydrocarbon, simplest naphthalene. Anyone know where you might encounter naphthalene? Mothballs. Mothballs, excellent. So naphthalene is a solid, it's crystalline, it's actually very beautiful, big flaky crystals. Okay, you're in the lab course right now, have you done a crystallization experiment yet? Yes. When you see crystals coming out, to me that's magic, I mean it's beautiful, it's a snowflake coming out. Naphthalene has some of the most beautiful crystals you can see. Benzene is a liquid, it boils at 80 degrees. It used to be widely used as a solvent to dissolve things, but they found it was a little bit personogenic, not super personogenic, but rather personogenic. And so slumping it all over as a solvent generally is revoked and it's only in very careful amount. I'll give you one more example so you can see the diversity of things that we would call aromatic compounds. This compound is called phenylethane. And when you have a benzene as part of a molecule, you say that the benzene is a phenyl group. And I write out problems for the course for quizzes and interns, problem sets. I often like to take examples from real scientific literature where people have really done experiments. And often the molecule will have a phenyl group in it, so you may see a phenyl group as a common feature of an organic molecule. Generally aromatic compounds are less reactive than alkenes and alkynes. So for example, if I take benzene and I add bromine to it and just mix them, there's no reaction. But if you want to make them react, which chemists often do, you can add a catalyst. So for example, if you add a Lewis acid catalyst, I'll again put this as a big except. And an example of a Lewis acid catalyst that one might deliberately add to make this reaction occur would be say, Baren3 bromide, Baren3 bromide, FB, BR3. So I'm giving you a little bit of a flavor of different chemistries right now. And so this is a reaction that you'll see later on. So you'll see that there's a lot of aromatic compounds in general if you were to think about how to test for whether something were an alkener and aromatic compounds adding bromine would be a good test. Now later on you're going to learn that there's a special stability to the benzene ring, where there are over 30 kilocalories per mole extra stability, about 36 kilocalories per mole associated with a special property called aromaticity when you have three double bonds in a ring next to each other. So what's the normal taste of what the future has to hold in terms of your learning? All right. When we were at the end of last class we were talking about alcohols. And we said that alcohols like ethanol, methanol, small alcohol are miscible with water. They mix in all proportions. Bigger alcohols like 1-butanol dissolve in water but they're not miscible with water. And very big alcohols don't dissolve in water to any appreciable extent. All of the molecules that I've just shown you, all the alkanes, the alkemes, the alkymes are hydrophobic. They don't dissolve in water at all. Benzene doesn't mix with water. Magtalene crystals float on top of water. 1-butane doesn't dissolve in water to any appreciable extent. And either does ethane. And the big difference is polarity. Like dissolves like water has hydroxyl groups, water is polar. So water dissolves molecules with polar functional groups if there isn't too much grease. A good rule of thumb on solubility. It's very hard to come up with absolute rules here. So this is what I would call a rough rule of thumb. It is if a molecule has, let's say, one nitrogen or oxygen containing functional group for five of pure carbons, it will be soluble in water. You're going to have a little bit of a hesitant to write this up on the blackboard because there are plenty of exceptions to this rule. But it's a very good starting point for thinking about what's going to be soluble in water. And this is important because in your laboratory course you're going to be dissolving compounds in water and organic solvents and trying to get them to go where you want them. And you're going to be wondering what's soluble in what. This is also important in medicine. This is super important in medicine because companies spend a billion dollars to develop a new medicine that's going to cure disease. And if the medicine doesn't have the right solubility properties in water, it's not going to get into your bloodstream. It's not going to get where it's needed. It's going to pass right out of your body through your digestive tract and it's going to be a dud. So these properties of water solubility and another property called hydrophobicity which talks about how the molecule will partition between reesey solvents and reesey tissues in your body. These are very, very important properties in medicine. Alright, another generalization that I'll make and again I can come up with exceptions and make it plainer on I'll mention one or two is that most organic compounds are soluble in other organic compounds. And more specifically inorganic solvents. In the laboratory it's very rare that you would mix two chemicals directly without a solvent to dissolve them. A solvent helps bring them together. A solvent helps dissipate heat when they react with many reactions or exit thermic and if you just mix two pure chemicals they may react very violently. And a solvent helps you direct the compound where you want for example to put it into a solvent layer, an organic layer and to wash away inorganic chemicals. Something that you're going to be doing a lot in the laboratory. Force wash away inorganic reagents that you add to the reaction mixture. So some typical solvents are things like diethyl ether, CH3, CH2O, CH2, CH3. When I talked before about free-basin generating a free base of amines or amine drugs, one thing that's often done is to use diethyl ether as a solvent to isolate the free base. And in the case of some drug users as in Richard Pryor I believe it resulted in a very bad burn when he used combined flames and organic solvents, diethyl ether. So the other organic solvent is hexane, CH3, CH2, CH2, CH2. And hexane is an alkane containing six, hence the X-carbons, one, two, three, four, five, and CH3 makes six. So an example of an organic solvent is dichloromethane, CH2, CH2. Precisely for reasons of hazard like flammability in industrial processes where they isolate large quantities of organic compounds, non-flammable solvents like dichloromethane are often preferred to flammable solvents because of the hazard that's posed for a large amount of a burn. For this experiment, a thyroid could only be calibrated when a person's loved one selects cartilage, it's no longer the alternative. Closing the agreements. All right, what I'd like to do now is to start to take a trace through various other functional groups. Most of the functional groups contain what organic chemists often refer to as heteroagens. The heteroagens are just a shorthand for atoms other than carbon and hydrogen. So we already talked about alcohols. The compounds for the structure of ROH that contain the hydroxy functional group. Closely related in some ways to alcohols are ethers. The general structure of an ether is ROR, say ROR prime. ROR prime just means it can be a different ROR group, a different alcohol group, or it can be the same alcohol group. We call the ROR group and the on-copsy group. So for example, in diethyl ether, we're going to do it on the previous board, but I'll go ahead and do it over here. CH3, CH2, OH2, CH3. We call the OH2, CH3, and ethoxy group. Ethoxy is ethoxy. So alcohols, of course, are like water I mentioned before where you have one of the hydrogens replaced by an oxygen ether. Like alcohol, for now you have the second H replaced by an alcohol group. I say a hydrogen group. We're here, one of the hydrogens replaced by an alcohol group. There are lots and lots and lots of relationships and this is what, to me, makes so much sense about organic chemistry is when you start to look at molecules as part of families and then families being interrelated in various ways, you realize these are not just a disparate collection of facts, but rather relationships that fit into a bigger picture and are uneasy to understand as part of a bigger picture. So if you move down the periodic table from oxygen down one row to sulfur, then you just come up with the sulfur analog of an alcohol. And the sulfur analog of an alcohol is a thiol. The general structure of a thiol is RSH. We call the SH a mercacto group. And I'll give you one example of a thiol, CH3, CH2, CH2, OH, SH. My mind is still one row up the periodic table. So this molecule is called one butane thiol. Sometimes you'll also hear it referred to as a common name of butyl mercactan. This molecule states most thiols smell really, really bad. The receptors in your nose are designed to pick up polar isobole, polar atoms and you end up smelling them really well. There are metals that bind very strongly. You smell you know where cap can be for. You know where you smell that. It's used somewhere in gas, in natural gas. Methane doesn't actually have any odor to it. But you don't want to have a gas leak in your stove or your water heater or your furnace. One of the gas pipes in your house will fill up with an odorless gas until it ends up blowing up with some spark source sets it off. So they add just a teeny bit, parts per trillion or parts per billion, a minuscule amount of fuel over a cap dendtle, weren't you? And the risk of a natural gas explosion is very real. There's an article in the New York Times last year I believe about somebody who was involved in a bitter, bitter divorce in New York City who opened the gas in his house to fill it with gas and this multi-million dollar town home in New York blew up from the mixture of methane and oxygen and whatever fire source was in the house. And of course if we talk about use of things, one of the biggest uses of outcades is its fuels. They're present in gasoline, there's natural gas. They come from petroleum as do alkene, alkynes and aromatic compounds. They are all present in petroleum which is the starting beam stop for many, many organic chemicals. All right, nitrogen and oxygen are the biggies for most organic containing functional groups. There are many, many functional groups that end up containing nitrogen and oxygen. Amines are the simplest nitrogen containing compounds. Just as alcohols and ethers are related to water, amines are related to ammonia. And so for example I can write R in H2, that's an amine. R2 in H, that's an amine. Just as we have an alcohol with one group on the high pond water, one group on oxygen, ether with two, we can put one, we can put two on nitrogen just like it would replace the hydrogens of water with the alcohol group. You can replace the hydrogens of ammonia with an alcohol group. And of course these could be two different ones. It could be R in H, R prime. And you could put three groups, R3 in, or three different groups. I'm not going to write them out. Just like we make little distinctions or we make distinctions among alcohols and ethers and they have some different properties. We make distinctions among amines. We call an amine with one R group a primary amine. And amine with two R groups a secondary amine. And amine with three R groups a tertiary amine. In an amine we refer to the NH2 group as an aminobrope. Technically there's a different name for example for the NH in the secondary amine but I think most people would just refer to it as an aminobrope. Technically it's called an aminobrope at least in some circles but I would refer you with that distinction. And I'll just give you a couple of amines. Again you will see nomenclature. Later CH3 NH2 is called methylamine. It's a primary amine. And amine with three Ethyl groups on the nitrogen CH3 CH2 3 N meaning that all three hydrogens of ammonia have been replaced with Ethyl groups is called triethylamine. So we've already talked about amines as being present in amino acids. I think I mentioned earlier in the class when we talked about polypeptides and proteins. Amines are present in many natural products. There's a whole family of natural products called alkaloids, plant compounds that contain amines. Many of them have biological activity. I mentioned one of them when I talked about cocaine and making the free base of cocaine. Let me draw up another amine, another alkaloid that's also very biologically active and very important in medicine. Let me draw the structure of morphine. And I want to do this for two reasons. One is I'd like you to see how the pieces that we've just talked about fit into a real organic molecule, a big biologically active molecule. The other thing I'd like you to do is to see how you can draw these structures yourself. So we're going to draw the structure. I'm going to draw it very slowly. And then we're going to identify all of the functional groups in this very important natural product. Morphine is used widely as a pain reliever. It's an addictive pain reliever. So often the pain reliever to use after surgery or when people have very painful cancer. It is a chemical precursor to heroin, which is made synthetically. So I'm starting my drawing of morphine by drawing a benzene ring. And I'm going to draw it horizontally just to make it a little bit easier to draw. I'm going to connect this benzene ring to another six-membered ring. This six-membered ring is not a benzene ring. There's one double bond in the six-membered ring. There's also an oxygen atom connecting the two six-membered rings. Now I'm going to draw a wedge line here, a hash line here rather. Remember we used hash lines to mean going back into the plane? There's what we call stereochemistry at that carbon. You're going to learn more about this later. But we've already seen the concept of representing three dimensions in two dimensions by using dash and hash and wedge lines to represent respectively going back into the plane and coming out of the plane. I'll draw one more six-membered ring up on top. And there's one more ring in this molecule. I'm going to draw a wedge line, a bold line to represent that the stereochemistry of this carbon has the next carbon coming out of the plane. And then I'll draw another line here. If you're very good at drawing, you can help show the three-dimensional structure by erasing just on the edge of this line to show that this other line has come over. Most people these days probably wouldn't do that by hand. It takes a little bit of planning. But if you're a better artist than I am, then you might do that. I'm putting in a nitrogen in the molecule and I'm connecting that nitrogen up to this carbon. There's also a methyl group on the nitrogen. We have a hydroxy group on this ring, a hydroxy group on the other six-membered ring on the right. And I'll show one more piece of stereochemistry of hydrogen coming out of the plane. All right. Well, this molecule that wouldn't have made sense to you at the start of the course now has some meaning and we can see some pieces to it. What's that piece? The benzene ring, an aromatic ring. This piece, hydroxy group, same over here. What would we say this oxygen is part of? It's a heteroatom and what would we say the functional group of an oxygen with two carbon substituents is on it? It's an alkoxy group and we would call that group an ether. So the distinction is we would say that the OCH2CH3 in diethyl ether is an alkoxy group, is an ethoxy group. The oxygen itself is an ether oxygen. Over here, double bond, so we have an alkene group. Hey, what does this mean about morphine? If I added bromine to it, it would react and the color of the bromine would disappear. We would go to red and the colorless. What type of amino group do we have up here? Tertiary amino group. All right, so there we've seen alcohols, amines, aromatics, ethers, alkoxy groups, or aromamino groups, all in one molecule. All right. All right, let's continue with our discussion of heteroradoms and we'll take a look at alpha halides. Alpha halides, of course, are compounds containing a halogen. So for example, CH3Br, we would call bromomethane. It's another name for this molecule, methyl bromide. Where have you heard of methyl bromide before? Half an hour ago. Half an hour ago. Anywhere else? Newspapers or stores, too. Methyl bromide used to be used up until a few years ago as a fumigant on fields, on crop fields like for strawberry crops because it's poisonous and it kills various pests in the ground that attack the strawberry plants. It's also destructive to the ozone layer and so now it's used, I believe, to be banned in agriculture and that's probably a good thing. Of course, they still pump toxic stuff into the ground and kill pests, they just pump different toxic stuff into the ground. So we would call the BR in methyl bromide as bromomethane, a bromobrute. We move along the periodic table. The BRH3Cl would be chloromethane. This is a chlorobrute. Chloroalkanes used to be widely used. You've heard the term CFCs. These are chloroalkanes that contain the chlorine group and the chlorine group. Professor Jerry Golden here at UCI discovered that chloro-chloro-hypertarbons or chloroalkane destroy the ozone layer and so eventually after many protests from companies like Pupont and lots of resistance, they were banned. And now in your air conditioning, instead of chloro-chloro-hypertarbons you find HFCs that have some hydrogen in there, hydrochloro-hypertarbons that end up not being as destructive to the atmosphere. So if we move up in the periodic table, CH3F would be a chloroalkane, it would be chloromethane and eventually, Shuri Holland was recognized for this with the Nobel Prize. And finally, let's just move back down CH3I-Iodo-methane and then we'll see what happens next. I think this is a good time to stop our discussion of heterowires containing compounds. Next time we're going to pick up talking about carbonyl containing compounds, we'll discuss the toes, aldehydes, esters, and then we'll move on to some properties of compounds.
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This course covers topics such as bonding and structures, acids and bases, organic molecules and functional groups, alkanes, stereochemistry, organic reactions, alkyl halides and nucleophilic substitution, alkyl halides and elimination reactions, and other various topics.
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10.5446/19377 (DOI)
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Good morning. So today we're going to pick up with some of the ideas that structure and we're going to do some organic chemical compounds. Some of these are rules based in the sense that you learn initially how to draw Lewis electron dot structures by counting up electrons and putting them together. And then some of its pattern based, once you get the hang of it, you're going to see, oh wait, this is a carbonyl. I know how to draw a carbonyl. This is an alcohol. I know how to draw an alcohol. So we'll have these rules initially to fall back on. So last time we were talking about bonds and we said most of the bonds of relevance for organic chemistry are covalent bonds. And then we further divided these into polar covalent bonds, non-polar covalent bonds. Remember we said polar covalent bonds generally have a difference in electronegativity of less than about two. And it's always a little fuzzy. Ionic bonds, by contrast, have a difference in electronegativity of two atoms involved, typically greater than two. And then it is less than about a ham, less than about 25, we'd say a bond is pretty much non-polar. So it's important to have the grasp of some fundamental electronegativities. And the great thing about being an organic chemist rather than an inorganic chemist or a physical chemist or a learning chemical chemist is we have a very small view of the periodic table. So most of us are organic chemist, there are plenty of elements out there, but we've got hydrogen and some of the alkaline metals, maybe magnesium and carbon oxygen, nitrogen, halogens, sulfur, maybe phosphorus. And so I want to talk about those elements and also show you some trends. What I'm going to do is to jot down electronegativities of the elements that I typically worry about. Probably at this point in your education it's worth actually committing these numbers to memory. Certainly by the time you come along to a state where somebody like Johnny or Buck is in their education, they know these trends well enough. Now if they're going to look and say, oh, carbon lithium bond, that's a polar covalent bond, they may not remember that it's an electronegativity difference of 1.5, but they'll certainly have the gist of it. So let's take a look. We have, hydrogen is of course the first element in the periodic table, and its electronegativity is 2.2 on the Pauling scale. As we move down the alkaline metals, of course they're much more electropositive than hydrogen. So lithium is 1.0, sodium is 0.9, they're all very electropositive, and potassium is 0.8. Now let's again keep in with sort of our view of the periodic table. So we're seeing something here. We're seeing that as we move down the periodic table, our electropositivity increases, or conversely as we move up the periodic table, our electronegativity increases. So I'll draw this arrow here, and let's see what happens as we move across the periodic table. So let's go from lithium, let's skip all the way over across. We'll forget about, for now, beryllium, which is a relatively unimportant element. So we'll skip, and we'll skip boron, which is a concern to chemists typically beyond the sophomore level. So let's go directly to carbon here, nitrogen, oxygen, and chlorine. Carbon, the electronegativity is 2.5, nitrogen, it's 3.0, oxygen, it's 3.4, and chlorine, it's 4.0. So our electronegativity increases as you go across the periodic table. And that's nice to know, because that means even if you happen not to remember the electronegativity of carbon and the electronegativity of oxygen, you'll know that when you have a bond between carbon and oxygen, the oxygen has a partial negative charge. The oxygen is delta negative, the dipole points from carbon to oxygen. Now remember, we saw this trend of as you go up, the alkaline metals, our electronegativity increases. And that's the same in the halosin, that's the beauty of the periodic table. You have trends that really pervade. So as we go from chlorine to chlorine to bromine to iodine, your numbers go 3.4.0 for chlorine, 3.2 for chlorine, 3.0 for bromine, and 2.7 for iodine. So I'll throw in one more element. As I said, an angle throw in more arms, which is of some relevance, phosphorus, which is of some relevance. I'll throw in just one more that you'll encounter this academic year, and actually we'll encounter later in today's talk. So sulfur is 2.6, again this trend, as you go up, you go increasing electronegativity as you go from sulfur to oxygen. Alright, let's take these numbers. And an idea we talked about last time, of ionic bonds having an electronegativity difference of greater than about 2, and covalent bonds less than about 2, and nonpolar covalent bonds having a sort of less than point black. Let's take a look at some chemical compounds. So let's start with some simple stuff that you see in G-CAM. Hydrogen fluoride we talked about before, just about as polar as you can get. Hydrogen is 2.2, fluorine is 4.0, so we have a big molecular diethyl while a big bond diethyl, which in the case of hydrogen fluoride, happens to be in the same as the molecular diethyl because it's diatomic, and it's pointing from fluorine from hydrogen to fluoride. This is just the same concept that we said last time, that we have our delta-negative on fluorine and our delta-positive on hydrogen. We looked at carbon dioxide last time. Let's take a look at it in light of our electronegativity numbers. So we said carbon was 2.5, oxygen was 3.4, and so you have bond dipoles pointing from carbon to oxygen. What about the molecule itself? Is there any net molecular dipole? No. Why not? They can't be right exactly. So we have bond dipoles, but no molecular dipole. So hydrogen fluoride is a polar molecule, carbon dioxide is a nonpolar molecule. And then just for the sake of contrast, the last time I put up sodium chloride and magnesium oxide, we said they were ionic compounds. Now I've given us some electronegativities. We have 1.0 for sodium and we're on a 0.9 for sodium and 3.2 for chlorine. And so this fits with our concept of greater than 2 electronegativities and ionic compounds. Same thing with magnesium oxide. Where magnesium, I said, was about 1.3 and oxygen was about 3.4. So it makes sense that it's an ionic bond. Later on in the class, you'll be encountering compounds where you have a bond between carbon and magnesium. These are a class of organometallic compounds called ring yard reagents. Organometallic compounds means compounds where you have carbon bound to a metal atom. And you can already tell me, is a ring yard reagent something like methylbeglesium bromide? Don't worry about the MGBR part, but is the bond between the methyl group that's between the carbon and the monority writing like an organic chemist here? We'll get to that in a moment. Is that a covalent bond or an ionic bond? Covalent. The electronegativity of carbon is 2.5. The electronegativity of magnesium is 1.3. It's less than about 2. So this would be a polar covalent bond. Alright, let's try our hand with a real organic chemical. One of the smallest. Maldahine. I'll be good. I'll even draw in my lone pairs of electrons. No for you. Have you heard of formaldehyde before? Biology. Do they still use it? Yeah, so formaldehyde was the classic compound for preserving specimens. It reacts with all sorts of groups like DNA, cross-link proteins, it kills bacteria. It's great at killing everything, including people. It's also carcinogenic, so the vapors are very bad for you. So nowadays substitutes are found. But it's one of the smallest organic compounds and it's a nice example for starting with looking at bond dipoles and molecular dipoles in organic compounds. As a knee jerk reaction at this point, most people in the room will probably know their electronegativities well enough and know, okay, all of these bonds in this molecule are covalent, not ionic. If we want to get a little more detail, we could say 2.4, 2.5, 2.2. So we could say we would call this bond a CO bond, a polar covalent bond, and the CH bonds for all intents and purposes are nonpolar. The main bond dipole in the molecule is going to be the CO bond dipole. There are also a couple of small bond dipoles from the CHs. Not very important. But the overall result is that you have a next molecular dipole like so pointing outwards and carbonyl. So that's all right. Thoughts or questions? Let's take a step back so we can all get on the same page and get comfortable drawing structures like this. And so I want to take a moment to review how we draw Lewis electron dot structures. We'll start with something easy and then get to something a little more confusing, maybe even spend some time chewing on it. So we'll start with a molecule, carbon dioxide, CO2, the one that we've been drawing a couple of times now. Remember how you do it? You pay attention only to the valence electrons in each atom. And we're going to see how many valence electrons all of the atoms bring to the table. And then we're going to try our best to arrange them so that everybody gets a complete octet. Because with the exception of hydrogen and sometimes elements like sulfur further down the periodic table, all of the elements want to complete octet. And again with those exceptions, you can't put more than 8 electrons around your atoms. You can't have an hydrogen with 10 electrons around it, for example. Alright, so our oxygen brings 6 electrons to the table. And I'll just draw them like this. Our carbon brings 4 electrons to the table. And I'll draw them like this, dots to represent the electrons. And then we'll put 5 around the oxygen. And our other oxygen also brings 6 electrons to the table. Alright, and then by whatever means we can group those electrons. You can do this mentally. You can do this by drawing around them. I'll just gather them up in little circles here just to remind us that we're bringing these together. And then we can group them together and say, alright, here's our carbon. Maybe in the beginning of freshman chemistry you would do it like this. Here are our oxygens. And I've drawn 2 pairs of electrons between the carbon and the oxygen. 2 pairs between the carbon and the other oxygen. And 2 pairs of electrons at each oxygen. And certainly after any short amount of time you would now be drawing these structures like this. Saying alright, that's going to, we're going to use our bonds. Each bond represents one electron. We'll draw our own pairs of electrons on the oxygen. If we're good we might even try to put them sort of at 120 degree angles to represent the Fp2 hybridization. Although at this point that's not critical. There's our CO2 molecule. Now let's try something that's a little closer to the hearts of organic chemists. We have our CO2 methodol CH3OH. So now we bring to the table 3H dot, 3 hydrogens. Each with one electron. We bring it together, we bring in a carbon with its 4 valence electrons. We bring in an oxygen with 6 electrons. And we bring in a hydrogen with its electron. And the first time you see it, if you just say CH4OH methanol, the first time you see it you say wait a second, how do I put all of those atoms together? But after you start to hear these names methanol, methyl alcohol, you realize oh there's a methyl group, a CH3 group, and the oxidative alcohol group, NOH group. And we'll be coming back, remember I said there were three big concepts, functional groups, perv-eronotation, and stereochemistry, inorganic chemistry. We'll be coming back to these functional groups in just a couple of chapters. So let's put all of these together to make our structure of methanol. Like so. And here's our structure of methanol, a full Lewis structure of methanol. After a short time you're going to find you're writing these things like CH3OH. And just taking as a given that oh yeah, you could expand out the methyl group, but we're not going to bother with that. So this is really how organic chemists think about structure and bonding. All right, let's turn our example now, let's turn our attention now to a little bit harder example. Let's see if we can struggle through it. All right, the little bit harder example that we're going to turn our attention to is dimethylsulfoxide. CH3 taken twice. SO. Dimethylsulfoxide is a laboratory solvent. It's also been used in sports medicine, although I wouldn't recommend it. People probably don't sore muscles, maybe band now, but certainly it used to be popular. It drives all sorts of chemicals through your skin, so it's not a good idea to actually put it on your skin, but people have claimed it gives relief. All right, let's apply the same types of principles that we used before to figure out the structure of this molecule. As I said, we quickly get the hang of writing out our methyl groups as blocks. So we can bring two methyl groups to the table. All I've done is imagine pregrouping the hydrogens and the carbon with three of its long pairs of electrons, leaving one, three of its four electrons and leaving one electron. Our sulfur is below oxygen in the periodic table, so we know that we write sulfur just like oxygen. In other words, it has six electrons around it, as does our oxygen. Now we have to figure out how to put these all together. Think of all of us to think about that. The first thing you might think about is the idea of, well, I understand I can form some bonds between my methyl groups and my sulfur. And I still think to have my oxygen. Look, can you say, how do I put this all together? Connect the sulfur to the oxygen. The oxygen has six electrons. It just wants two more. So it's happening. Connect the sulfur to the oxygen. We'll have eight electrons around everybody. Everybody gets a complete octet. The sulfur could have extra electrons as well. We're going to come back to that notion, because this is a molecule that's nice to chew on. We're going to come back to that notion in just a moment when we get to the idea of resonance structures. And the fact that many molecules can be represented better by more than one Lewis structure. And together those comprise a complete picture of the molecule. We're going to also chew on dimethyl sulfoxide as we talk about formal charges. So let's start and try to address the concept of formal charges. Another one, I think formal charges was in general chemistry. So let's review what formal charges mean, because this is actually important to organic chemistry. The question is, yes, can we draw a double bond between the sulfur and the oxygen? Yes, can we draw a double bond between the sulfur and the oxygen? And this is one very special case, because the sulfur can have 10 electrons around it. This is one very special case where you could indeed draw an extra bond. We would imagine sharing this pair of electrons. And together these two structures, which I'll put in a big, big pair of brackets, are going to make up a more complete structure of the molecule. Now you wouldn't know this, and I wouldn't necessarily expect you to know this. But in the case of dimethyl sulfoxide, the resonance structure on the left is actually a little more important than the resonance structure on the right. We're going to come in just a few moments, either at the end of today's class or the beginning of the next class, to cases where I would expect you to be able to say which is the more important resonance structure. Here there's a little bit of an apples and oranges comparison, because the sulfur has an expanded octet in the resonance structure on the right. You have a poorer bit of overlap between oxygen and sulfur because they're in different rows, and so you don't have that much double bond character. But again, that gets a little beyond the scope of this course. So let's get to our formal charges. You are way on top of things, and this is fantastic. So let's get down to our formal charges here. And we'll start again with some simple, simple stuff. Now in cases of formal charges for you, in cases of formal charges where you're comparing apples and apples, elements in the same row and the periodic table, everyone having a complete octet or everyone having the sulfur and not having a complete octet, it's a simpler comparison. When you get between the second and third row, between carbon and phosphorus or carbon and sulfur or phosphorus and oxygen or sulfur and oxygen, gets a little bit more complicated. Right now what I will say is for dimethyl sulfoxide, both of these resonance structures are correct pictures of the molecule. Together we get a little bit more complete picture of the molecule. Alright, let's start with formal charges because this will help lay our lay the grounds for discussing resonance structures. So a formal charge really can be thought of as a bookkeeping mechanism to keep track of where the charge is. What do I mean? If you have a molecule, either that molecule is neutral or that molecule is charged, in other words, it's in high amount. Charges comes in one, so your molecule can have a charge in zero, it can have a charge in plus one, it can have a charge in minus one, etc. Formal charge basically addresses where is the charge. So for example, probably since your very first quarter refreshment chemistry, you've seen NH4, what do we call it, NH4 plus, ammonium, ammonium high on. And if we expand that out to a Lewis structure, we have eight valence electrons, which we share between the nitrogen and the hydrogen, and the molecule has a net charge. Formal charge basically is the bookkeeping mechanism of saying where does that charge reside in the molecule. And the way we address this question is by a low gain. And the gains like this, remember how we said that in making our Lewis structure, we simply look at how many electrons every atom brought to the table. In calculating formal charge, we say let's take all of our covalent bonds and divide them up equally, share and share a life or break them up equally. In other words, we'll give each hydrogen one electron from each bond, and we'll give back to hydrogen one electron from each bond. And then we'll look at where the charge is. The nitrogen brings one unbalanced positive charge to the table, and we give it back one electron, so that's plus one, minus one, zero. So there's zero formal charge on the hydrogen. The hydrogen brings to the table five unbalanced positive charges. In other words, if you count your way across the periodic table, it's number five across. And yet we only have four electrons, so we give it back minus four. The net result is plus one. So we have our structure of ammonium and assign formal charges. Our formal charge is a positive charge on the nitrogen. So let's try that same approach with dimethyl sulfoxide. I'll explode all of our bonds in this same way. And we'll look at the various atoms. The hydrogen should come as no supply, and it fries plus one, minus one, zero. It's a well-run electron on the carbon, so no formal charge on the hydrogen. The carbon probably comes as no surprise. Plus four, minus four brings to the table four nuclear charges. We've given it four electrons, so we're zero. The sulfur brings to the table. It's in the same row as oxygen, so it's plus six. We only have five electrons, so its net charge is formal charge plus one. And the oxygen plus six, minus seven, is minus one. So if in this resonance structure of dimethyl sulfoxide, we assign our formal charges. And I'm just going to write our methyl groups as CH3. Now we have a positive formal charge on sulfur, minus formal charge on oxygen. And we have a positive formal charge on oxygen. Great question. In dimethyl sulfoxide, it's probably about 60%. Remember, resonance structures, of course, are two different pictures of the same thing. Both present at the same time, representing our inability to, our inability to make one single structure to show the difference in the electrons. In the case of dimethyl sulfoxide, because we have the bond between the double bond, between the second and third row element, they're an extra little bit bad. So in the case of dimethyl sulfoxide, this resonance structure is actually a little bit more important. If it were a comparison between equals, say second row elements carbon and oxygen, then the resonance structure that had a minimum separation of formal charge would be more important. And actually along those lines, and perhaps as one to think about on your own, I'll give you, they even be in the homework. So if you have looked at which ones I assigned, certainly this one, or please note this morning, certainly there are similar things in homework. On your own, why don't you think about this molecule, methyl azide, and think about what resonance structures there might be. And what the formal charge is and what importance there would be to them. That's a good one to think about on your own. Alright, let me write out what I've been saying about resonance structures. Give us a couple of good examples. So what's wonderful about Lewis electron dot structures is they allow us to get a very simple picture of the structure of the molecule. What's limiting about them is the distributions of electrons in the molecule are often a little bit more complicated. In the next lecture or the following one, we'll talk a little bit about molecular orbital approaches to understanding structure of the molecule. But the truth is the bread and butter of my thinking and most organic chemists thinking about molecules is the type of structures that we're dealing with in today's class. Now the limitation is sometimes a single picture just isn't good enough. And we'll take a couple of examples here. One is CH3CO2 minus acetate anion. You've probably already seen acetate in your general chemistry class. And so I can write a Lewis electron dot structure of acetate like so. And this molecule does have a charge. The formal charge is on this oxygen. I'll write negative. And this Lewis electron dot structure implies that there's a double bond to the top oxygen and a single bond to the bottom oxygen. That there's no charge on the top oxygen and that there's a charge on the bottom oxygen. And somehow those oxygen atoms and those bonds are unequal. And this of course is not the case. I could just as well write a structure in which the rolls are reversed. There's a double bond to the bottom oxygen and a single bond to the top oxygen. And that structure would be just invalid. And together the two of them make up the best picture that I can write of this molecule using Lewis electron dot structures. It's not the structure on the left. It's not the structure on the right. It's not that the oxygen on the bottom has a negative charge and the oxygen on the top is neutral. It's not that the oxygen on the top is neutral. It has a negative charge and the oxygen on the bottom has is neutral. It's that both oxygens have half a charge. Both CO bonds have a bond and a half in character. And the confusing thing about the term resonance structures is that we do not resonate. We do not oscillate. We do not vibrate or cycle between those structures. It's both of those structures at the same time all of the time. As I said, the sulfur one is the one tricky one and nobody's going to hold your feet to that top, your defy rod. The sulfur one is the one tricky one because the other rule that ends up fighting with that rule is that double bonds between rows, particularly between the second row and carbon and oxygen and hydrogen row, and lower rows like sulfur and phosphorus and chlorine and bromine and so forth, are not very good. What would the form of the reaction be if we compared as a moral argument? Yes, if you have with all other things being equal, charge on a moral like for a negative, better. Other questions, these are actually really, really good questions and they're really on the mark. And this is exactly the sort of question I have to hear people asking every year. So you're right on the mark in asking this. Where does the fifth nitrogen electron go? Well, they're all shared, so the nitrogens bring five electrons to the table. Your hydrogens, you'd actually put it together by bringing three hydrogens in and then bringing in a proton that doesn't have any electrons. But the eight electrons in the ammonium ion end up being shared between the nitrogen and the hydrogen. Other questions? In the case of dimethylsil, the question is how do you determine which resonance structure in dimethylsil bauxite? In the case of dimethylsil bauxite, the good news is everybody gets a pass in this class because we have these two opposing rules finding it out. As I said, the resonance structure with the separation of charges happens to be more important. But I wouldn't necessarily expect you to know that. And you'll actually see people write it all the way. One last question. How do you show flow? We're going to come to curve arrows in the next lecture and we will talk about how we can convert resonance structures. I want to show you one last resonance structure, molecule that organic chemists love and that molecule is benzene. Benzene was a real conundrum for organic chemists for many years. A Y is so special. And you'll get to why benzene is so special in either the B or the C course. But for now we're going to see just one special aspect of benzene. Benzene, of course, is C6H6. The carbons and hydrogens are put together in a ring. Carbons are in a ring. The hydrogens are off the ring. We have alternating double and single bonds around the ring. And each carbon, oops, I got a little bit below the edge of the board there, each carbon bears one hydrogen. And just as in the case of the acetate anion, benzene can be written by two equivalent resonance structures. One in which we have double bonds between these carbons here and single bonds between the other carbons. But then a second equivalent resonance structure. Again, my bottom hydrogen is just going a little bit below what was there. And that second resonance structure alternates the double bonds in the other direction. And just as in the case of the acetate anion, it's not that we have a double bond on one side and a single bond on the other, or vice versa. Instead, it's both of them at the same time, all the time, and together these two pictures make up a more complete structure of the benzene molecule. Alright, next time we will continue our discussion of structure and bonding, but we will move on to our ideas of different kind of structures and their own.
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This course covers topics such as bonding and structures, acids and bases, organic molecules and functional groups, alkanes, stereochemistry, organic reactions, alkyl halides and nucleophilic substitution, alkyl halides and elimination reactions, and other various topics. Index of Topics: -2:48 Trends in Electronegativity -7:25 Examples of Polarity -15:00 Lewis Structures -22:12 Dimethyl Sulfoxide -30:15 Formal Charges -35:58 Formal Charges and Dimethyl Sulfoxide -41:00 Resonance Structures -48:12 Benzene
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10.5446/19380 (DOI)
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Thanks. So today what I'd like to do is take just a couple of minutes to finish up some ideas from chapter one, and we'll be talking about molecular geometry, and particularly on there. And then what I'd like to do is to move on to chapter two, where we'll be discussing acids and bases, and particularly their relationship to organic chemistry. And just as in chapter one, where we took concepts that were familiar from general chemistry, but gave them an organic flavor, and began to think about the case of chapter one, structure and bonding in organic molecules, we're going to do the same with acids and bases, and begin to get to see the relationship to reactivity in organic chemistry. And at the very end of chapter two, we'll begin talking about, actually, even throughout, we'll begin talking about this very central concept of per error orientation that I talked about. Let's take a moment to finish up our discussion of molecular geometry. We've got a little bit of this when we were talking about orbitals and sp3 hybridized orbitals and so forth. And I just want to go through very explicitly. And let's start with sp3 hybridized atoms. So sp3 hybridized atoms have about 109 degrees, roughly a tetrahedral arrangement of ligands and lone pairs. Let's say about 109 degree bond angles and a tetrahedral arrangement of ligands and lone pairs. So we started by talking about methane before. Pardon? We started by talking about methane before. So that's where we'll begin right now. Here's methane. We have an sp3 hybridized carbon. And remember, we're going to think about the arrangement of ligands, the substituents, on that carbon. So we would describe the substituents as a carbon. So we would describe the geometry of methane as tetrahedral. By that, I mean you have four substituents around carbon. And if you look at all four of those substituents, they form the corners of a tetrahedral. In fact, in methane, all of the bond angles are equal. They're all 109.5 degrees. This was the geometry of a tetrahedron dictates. If we move across the periodic table from carbon next to nitrogen and to oxygen, we'll skip the floor and that's just going to be linear. We get next ammonia. And I'm going to draw the lone pair of electrons on top like so. Here's our hydrogen. Here's another hydrogen. And here's another hydrogen. If we just look at ammonia and forget about the lone pair for a moment, which is NH3, we just consider the arrangement of atoms that you see. In other words, you don't really see the lone pair. In fact, often when we draw ammonia, you sort of write NH3 and forget about it. We'd say that ammonia makes a pyramid structure where the nitrogen sits on top of a pyramid of three hydrogens as the base. So we would describe it as a pyramidal molecular geometry, even though the arrangement of ligands and lone pairs collectively is tetrahedral. The lone pairs of electrons take up a little bit more space than the pairs of electrons that are in a bond. That makes sense. The electrons in the lone pair sort of spread out in a bond. They're more focused between the two atoms. As a result, that crunches down ever so slightly on the hydrogen, nitrogen, hydrogen bond angles. And so the hydrogen, nitrogen, hydrogen bond angles are just a little bit under 109 degrees. They're 107.3 degrees. The exact numbers aren't too important in organic chemistry. They'll sometimes make a little bit of a difference, but you can think of it as 109 if you don't want to remember separate numbers. As we continue to move across the periodic table, then we get to oxygen, and hence to water. And I'll draw two hydrogens of water in the plane of the page and try to represent this molecule in three dimensionality by trying to show one lone pair coming out off the oxygen and the other lone pair going back. And so if we just look at the atoms, if we just consider the hydrogen, oxygen, and hydrogen, we'd say this molecule is bent. The trend of the lone pairs of electrons making up a little bit more space continues. So the hydrogen, oxygen, hydrogen bond angle is crunched down just a little bit more, 104.5 degrees. All of this falls into something that you've learned in general chemistry probably. Who's heard the name BSEPR theory, the electro-unpair repulsion theory? So this is just a review of BSEPR theory as applied to types of structures in organic chemistry. And of course what you'll see is as we move on from molecules like water, which are in the realm of inorganic chemistry, to molecules like methanol or dimethyl ether, which are in the realm of organic chemistry, the geometries stay the same. In other words, if instead of having a hydrogen here, we had a methyl group making methanol CH3OH. We would have a bent geometry around oxygen. And if instead of having a hydrogen here, we had another methyl group making dimethyl ether CH3OCH3, we would also have a bent geometry. All right, we've seen some sp2 hybridized atoms before. Sp2 hybridized atoms have about 120 degree bond angles and trigonal planar arrangement of Wiggins and Lohlen pairs. We looked at ethylene last time and we were concerned with an orbital based model of the structure of ethylene. We remember that we said the molecule ethylene is planar. So each of the carbons is sp2 hybridized and the carbon hydrogen, carbon bond angle, is about 120 degrees as is the hydrogen, carbon hydrogen bond angle. Let's take a look at another organic species. Let's take a look at the methyl carbocation CH3 plus. What's the first thing you notice about the valence state of the methyl carbocation? It doesn't have a complete contact. That carbon is very unlikely. In fact, you will never see a naked methyl carbocation in reactions in this class. You will in some cases in the gas phase. For example, under special conditions in the spectrometry, you will however see other carbocation where instead of having a hydrogen, you will have carbon atoms on the central carbon. In fact, in this week's discussion section, you'll see the tert-butyl carbocation which, like the methyl carbocation, doesn't have a complete contact but is a little bit less unstable. The methyl carbocation is also planar, trigonal. We have an sp2 hybridized carbon. We have three ligands around the carbon, no lone pairs of electrons, 120 degree bond angles, hydrogen, carbon, hydrogen. Methyl carbocation has a vacant p orbital, meaning that it has a p orbital with no electrons in it. That p orbital is orthogonal to the plane, so I'm now drawing the methyl carbocation like so. Here's our vacant p orbital. So we have six electrons in bonds with hydrogen and then one electron in special conditions. Zero electrons. We bring in a carbon, which has four electrons, three hydrogen atoms that would give you seven valence electrons, but you take away one, you have six, and a net positive charge. In fact, we drew the species, let's see, we drew a fluorinated carbon. Well, if you think about boron and you take a boron compound with three ligands on it, you also have a vacant p orbital and boron, so the carbon basically has been reduced to coping with not having enough electrons. Take one more example we saw last time from aldehyde. Maybe we saw it the previous time. Exact same situation as ethylate. The carbon is sp2 hybridized and the oxygen also is sp2 hybridized. You have two lone pairs of electrons on the oxygen of formaldehyde. Alright, last bit of geometry I want to talk about. sp hybridized atoms. sp hybridized atoms have approximately 180 degree bond angles and a linear arrangement of ligands and lone pairs. Let's take a look at a few examples. We talked about acetylene before. hc triple bond ch. The carbons in acetylene are sp hybridized. You have 180 degree hydrogen carbon and hydrogen bond angle in both cell lines. Take a look at another molecule. See a new functional group here. Let's take a look at acetonitrile ch3. Cn, I'll draw on the lone pair of electrons. As I said the name of this molecule is commonly referred to as acetonitrile. The carbon and the nitrogen are sp hybridized. The arrangement of the bond angle about the carbon and nitrogen bond angle is 180 degrees. Let's take a look at one more molecule, the molecule allene or 1,2-propadene. Allene is the common name for this molecule. You'll learn more about nomenclature when we get to systematic names. The question was would you rather we know IUPAC or common names? The IUPAC name of a molecule like acetic acid is ethanoic acid. You'd probably never hear anyone in class talk about ethanoic acid. It just wouldn't roll off the tongue. But you might see it, particularly if you have substituent on it. But then you'd recognize it. You'd say oh wait, yeah I know probably noic acid and euthanoic acid. So right now don't sweat. Don't blow on some of the more common terms we're getting. Allene is a very funny looking molecule. We haven't seen a molecule quite like this, but a carbon double bonded to another carbon on both sides. But of course we've seen a structure like this in carbon dioxide. With carbon double bonded to an oxygen on one side and double bonded to an oxygen on the other side. Now we have a little bit of a chance to think about hybridization. The central carbon is sp hybridized. And the outer two carbons are sp2 hybridized. And the carbon carbon carbon bond angle is 180 degrees. What makes it less than 180 or more than 180 degrees? Well we saw exactly the situation with long pairs where you can have uningual substituents along pair on one side. Takes up a little bit more space. Now in the case of 180 you're not really going to have that circumstance coming up here. But for example in formaldehyde if the hydrogen carbon hydrogen angle was a hair under, well that wouldn't even be a good example here. So basically ligands long pairs can take up just a little bit more than ligands. There are also cases where there are some really interesting variations in hybridization. And this is the stuff that makes chemists scratch their heads. For example I talked about carbon dioxide. If we can catenate and add another double bond here to an oxygen, that molecule actually has a little bend to it. And that's the sort of thing that makes chemists at a very advanced level say, why is this? We have simple rules and then we see there are some exceptions. And the exceptions are often the fascinating thing. You get people at an advanced level well beyond some organic chemistry to get excited about. Alright, well let us move on to chapter 2 now. I want us to begin talking about acids and bases in organic chemistry. Okay. Okay. Acids and bases are central to organic chemistry, both in the generation of reactive species. Species that we call electrophiles, nucleophiles, and also as reactive species in their own right. So this is why it's very important for us to think about acids and bases. And as I said, we'll use this also as a springboard for learning her narrow notation. Okay. Okay. Okay. Okay. Okay. Throughout the course of this week, we're going to start to see what this means. And then of course, because this concept is so central, it will come back to us again and again. We're going to see, for example, that what we've known of in general chemistry as Lewis acids, species that react by accepting a pair of electrons are very similar in many cases, the same as what organic chemists call electrophiles, things that want electrons. Species that we think of as Lewis bases in general chemistry, species that react by sharing a pair of electrons are what organic chemists call nucleophiles. I should close my parentheses. And in many cases, we're going to simply see protons coming on, protons coming off the organic chemistry. Let's start. There are a number of different models, correct models, for acids and bases. Let's start with a model you certainly learned first in general chemistry and in high school chemistry. What's it often referred to as a Bronsted acid or Bronsted lary acid? The definition of a Bronsted acid is very simple and intuitive. A Bronsted acid is a proton donor. Conversely, Bronsted base is a proton acceptor. And so we think of a general Bronsted acid base reaction as a Bronsted acid and a Bronsted base react together to give the conjugate acid of the Bronsted base another acid and the conjugate base of the Bronsted acid another base. What do I mean? Let's take HCl, hydrogen chloride. Hydrogen chloride is a gas. When you dissolve it in water, they react. You have an equilibrium. That equilibrium happens to lie very far to the right. In this reaction, the HCl acts as an acid. It domains a proton to water. The water thus acts as a base. We form the conjugate acid of water H3O plus salt. Say that this is an acid. And we form the conjugate base of HCl, namely chloride. So write that this is a base. We could write this reaction as an equilibrium. As I said, it happens to lie far to the right. In other words, if I wanted to amplify on this, I could draw a longer arrow on top and a shorter arrow on the bottom. But we could also write the reverse equilibrium. Chloride anion plus H3O plus is an equilibrium with HCl and H2O. In that case, we'd be saying a base plus an acid is an equilibrium with the conjugate acid and the conjugate base. Let's start to think about the mechanism of this reaction and the flow of electrons. And now we're going to use our organic chemist notation of the Kerr-Gerro. So I'm going to now draw the water very explicitly. I'll draw all bonds, long pairs of electrons so we can see how bonds were made and how bonds were broken. I'll do the same for hydrogen chloride remembering to draw in my three long pairs of electrons around chlorine. The water takes the proton off of hydrogen chloride. Electrons flow from the long pair of electrons on water to the proton to the Bronsted acid. We can't have four electrons around that hydrogen so electrons get pushed back onto chlorine. You'll notice how I draw my current arrows. I always start at a source of electrons, a long pair for a bond. And I always end up on an atom. And when all is said and done, the sharing of this pair of electrons with the hydrogen results in a new bond. So we have a normal positive charge on oxygen. And now we get our fluoride anion. We have four long pairs on the chloride anion. Now as I hinted before what's really powerful about this type of way of thinking is we can see all sorts of analogies. For example, if instead of using water in this reaction, instead of adding hydrogen chloride gas to liquid water to get aqueous hydrochloric acid, which is a solution of hydronium ion and chloride in water, instead I have done the same reaction with methanol CH3OCH3. We can predict what would happen. Methanol looks a lot like water. The only difference is we have a methyl group instead of a hydrogen. We still have an oxygen and still SP3 hybridized. We still have a long pair of electrons. And the other component in this equation is the same. So it shouldn't be a great leap to be able to predict that we should see a similar reaction in which electrons flow from the long pair on methanol to the proton. We push electrons back on the chloride. We set up an equilibrium. We get protonated methanol and chloride anion. We get a protonated methanol. We get a protonated methanol. Let's try another example. And again, I'll show the comparison between concepts that we get in general chemistry and concepts that we get in organic chemistry. Let's take the ammonium ion NH4 plus and we'll allow it to react with the hydroxide anion. Again, we have an equilibrium. The ammonium ion acts as a proton donor, in other words, as an acid. The hydroxide anion acts as a protoned acceptor, in other words, as a base. The hydroxide anion pulls a proton off of the ammonium ion and we can use the same concept of the curved arrow to demonstrate this. We have electrons flow from the hydroxide anion on the pair to the proton on ammonium. We push the electrons from the bond onto the nitrogen atom. Now we generate ammonia. This is our lone hair. Ammonia is the conjugate base of the ammonium ion and we generate water. Water is the conjugate acid of hydroxide anion. Let's try this same reaction with an organic compound. We'll try this reaction with methyl ammonium ion. We'll still use hydroxide anion. Now it should be very easy with all of these examples to predict what hydroxide anion does. We pull the proton off of the methyl ammonium ion. We push the electrons onto nitrogen. We have an equilibrium. We generate water and methyl amine. You'll often hear of this reaction referred to as making the free base of an organic amine. You can have an amine hydrochloride salt, for example, generated by a reaction of an amine with hydrochloric acid. When you add a base like sodium hydroxide, you'll pull that proton off the ammonium ion to generate the free amine. You've heard of this term, making the free base from an amine solver. When you hear of cocaine being free base, what that means is using a base like sodium bicarbonate to generate the free base of cocaine, the physiologically active form. Not only is free base a noun, but by popular usage it has ended up becoming a verb. Now, in our next lecture, we're going to be discussing the degree of acidity, position of equilibrium. In order to measure the degree of acidity or to characterize the degree of acidity, we'll often use the term pKa. pKa is a fancy way of saying negative log of the acidity constant, Ka. Ka is the acidity constant or the acid dissociation constant. And all that means is if you have an acid, we'll call it HA, and you put it into water, you set up an equilibrium of dissociation. An equilibrium between the hydronium ion and the conjugate base, A minus our equilibrium constant. Remember how you get that? That's just the concentration of products, the product that's multiplied out of the concentration of products over the concentration of reactions, or anything that's constant concentration like solvents. So in other words, Ka for acid dissociation equals the concentration of hydronium ion times the concentration of the conjugate anion divided by concentration of Ka. But simply that's the pH you get of a one molar solution where half of it is HA and half of it is A minus. So if you take half a mole of sodium acetate and half a mole of acetic acid, it's all about to make a leader of solution and measure the pH, you'll get about 4.56 of pKa of acetic acid. A strong acid is fully dissociated, a weak acid is partially dissociated, and what I call a very weak acid is essentially unmeasurably dissociated. So one thing to keep in mind is pKa is a long scale. What does that mean? That means a change in of one pKa unit corresponds to a change of tenfold in acid dissociation constant. A change of two in pKa units or a difference of two pKa units corresponds to a factor of two of 100 in acidity constant. So if at one end of the scale we take a look at HCl, a very strong acid, HCl has a pKa of negative seven. In other words that means that Ka equals ten to the seven. At the other end of the scale, the weakest acid, and I'll use that term very loosely, that you would ever see would be something like methane or another alkane. So the pKa of methane is 50, positive 50, Ka equals ten to the negative 50. What that means is if I dissolve the mole of methane in a liter of water, you would not have even a single molecule of the methane that's dissociated. It is such a weak acid, it is in the context of general chemistry, only an acid in name in that you could write an equation, but the equilibrium of methane and water to give methyl anions would be completely to the left. You would see no dissociation. So in other words what we're saying here is that HCl is ten to the 57th, I can't even wrap my head around such a big number, ten to the 57th times more powerful acid than methane. So that's what we're saying here. So we have a couple of questions. We have a great question, why are we moving the lone pair of electrons from the base to the acid? So we're beginning to think about organic reactivity, we're beginning to think about the making and breaking of bonds. Making and breaking of bonds is all about the flow of electrons. When we form a bond, we make a new shared pair of electrons. When we break a bond, we give up a shared pair of electrons and showing the current error of those that flow at the end of the bond. Alright, we will pick up next time talking about acid strength and look at various acids of varying strength.
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -1:29 Molecular Geometry - Bond Angle -3:12 sp3 Geometries -8:39 sp2 Geometries -14:50 sp Geometries -22:26 Chapter 2 -27:15 Bronsted-Lowry Acids and Bases -36:58 Ammonium Example -42:19 Acidity
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10.5446/19379 (DOI)
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Good morning! So, up until this point, we've been thinking of bonds as simply shared pairs of electrons between atoms. This is a very good model of structure and bonding. Works very nicely, easy for us to quickly generate structures. Today we're going to take a slightly deeper look at structure and bonding, and we're going to look at orbital-based models of structure and bonding. So, the idea of orbital-based models of structure and bonding is that bonding occurs because of the greater stability of electrons in molecular orbitals. We'll refer, in short, and to molecular orbitals as MOs, and that molecular orbitals are formed by the combination of atomic orbitals. Now, we've seen this approach to understanding structure and bonding before we've seen it in general chemistry. The basic principle is this focuses on the wave-wide properties of electrons. In other words, we think of our electrons as being spread out. We don't think of them as just two dots, gluing atoms together, but rather that when you have an arrangement of atoms that the electrons move around, and just like an electron in the hydrogen atom wants to be in the 1s orbital so it can be near the nucleus, in a molecule it wants to be in a bigger orbital so it can be near to be in many nuclei, and it's all spread out. Let's go back to what I'm sure you've seen in general chemistry in the look at molecular hydrogen and H2. So we've represented that structure already by H bonded to H. So let's take a look at an orbital-based approach to understanding the structure and bonding of hydrogen. So we can think of molecular hydrogen as being formed by combining two hydrogen atoms. And to do that, we bring together the two nuclei of the hydrogens and add the electrons. So here's one hydrogen atom. I'll write this as H dot, meaning that we have hydrogen with one electron. What I've tried to represent here is the 1s atomic orbital, that is 1s A0 for the hydrogen atom. And so that electron spends some time near the nucleus and sort of all smeared out around the nucleus. And we have two of these. Like so. When we combine the two hydrogen atoms then, we get a new molecular orbital. We're now here are hydrogen atoms. We have a new molecular orbital that encompasses, that wraps up the two hydrogen nuclei. We call this the sigma 1s molecular orbital. Sigma is a designation for an orbital that is cylindrically symmetric. By cylindrically symmetric, I mean like this piece of chalk, or at least this piece of chalk before I started writing and breaking the symmetry. If I spin it around on its axis, it's the same no matter how you look at it. Or a big sausage, big fat salami. As you spin it around, it's cylindrically symmetric. So when we combine two atomic orbitals, the 1s atomic orbitals, we get two molecular orbitals. So you need to combine your atomic orbitals in two different ways. And the way you can combine them is either an additive fashion or a subtractive fashion. So we've added them together. We've gone and said we have this orbital, we have this orbital, we bring them together, we mix them together, we get some orbital that encompasses the two nuclei. This orbital, of course, is a representation of where the electron is likely to be found. I'm limited by the limits of the blackboard, but you can think of this as a cloud where the electron can be found and where some places there's a higher probability. Think of it as a ball of cotton candy you might get at a fair, where you have fluffiness or a cloud, where you have less probability of finding the electron way, way out here. There's always some probability, more probability in closer. Now let's play with the idea of combining the orbitals in a subtractive fashion. And this is where students usually find the notions a little bit confusing. So here are two 1s atomic orbitals, but let us now imagine subtracting one from the other. In order to do that, we can just think, so this is a minus sign here, in order to do this we can just think of adding the negative of this orbital. This is confusing because you have to be thinking about orbitals and waves on the ocean. You have to think a wave can go up, a wave can go down, and two wave toms that are up, could interact with each other. Two wave tops that are down could interact with each other, but a wave top that's up and a wave top that's down doesn't, the bottom I suppose that's down, doesn't interact. So I'm going to shade. So here let me add a plus sign to say that we're adding them together. So minus sign, and here what I'm going to do is use a plus sign, but shade this orbital to indicate a negative phase. Now when we do that, what I mean is there's electron density here, but if I bring them together they can't overlap. There's an area where there's no electron density. And let me represent that addition by sort of a teardrop shaped structure like this. This is another molecular orbital. It's an anti-bonding molecular orbital. It's anti-bonding because we don't share electron density between the nucleus, nuclei because it's higher in energy for orbital electrons to be in this molecular orbital than it is to be in the sigma 1s molecular orbital. We call this orbital the sigma star molecular orbital, the sigma star 1s molecular orbital. And whenever you combine two atomic orbitals, you get a bonding orbital and an anti-bonding molecular orbital. Normally we can often forget, and we very quickly do forget about the anti-bonding molecular orbital. In fact, I'll be making some drawings in just a few moments where we do ignore those for the sake of simplicity. Let's see why we can ignore them very often. So here's an orbital energy diagram of the molecule hydrogen. My y-axis I'll represent energy. This is the energy of a hydrogen atom, 1s atomic orbital. We can think of the hydrogen atom as having one electron in it. We have another the same level, hydrogen 1s atomic orbital, and we can think of that as having one electron. When we bring those two hydrogen atoms together, we can think of that our sigma and our sigma star 1s molecular orbitals, the sigma star 1s molecular orbital is lower in energy. Sigma 1s molecular orbital is lower in energy. Sigma star 1s molecular orbital is higher in energy. In other words, we brought these two atomic orbitals together in forming our H2 molecule. We have two electrons. We put those two electrons in the 1s molecular orbital and we have sigma 1s molecular orbital and they are lower in energy. In other words, the net configuration is more stable. Thoughts or questions? Great question. Is there ever a time when the anti-bonding molecular orbital is filled? So the answer to that question is yes. If I give the molecule hydrogen another electron, the only place it can go is into the anti-bonding orbital. And yet the net energy of this configuration with two bonding interactions, two electrons in the bonding orbital and one electron in the anti-bonding molecular orbital is still more stable than H- and H-dunk. So there we would have a bond even, it would be half a bond in strength, even with one electron in the anti-bonding molecular orbital. You learned about helium in general chemistry. Everyone learned that hydrogen forms a bond between two hydrogen atoms and helium doesn't. And you probably saw a diagram very similar to the diagram that I put up here, probably with Professor writing H-e and H-e and showing each of these with two electrons and showing that if you bring the two helioms together, you have two electrons in the sigma 1s, two electrons in the sigma star 1s, so there's no bonding interactions that the helioms don't bond. And then the professor probably said to you, but if you take away one electron, if you make the molecule H-e2+, it is actually a stable species because you have an anti-bonding interaction. So yes, there are times. And when you get to learning about aromaticity and the molecule benzene, you will start to learn about putting electrons into the pi star molecular orbitals. Other questions? Alright, let us now turn our attention to organic molecules. And in order to think about organic molecules, we're going to have to introduce one more concept, also from general chemistry, the concept of high-brand orbitals. And we'll start with the molecule methane, CH4. So the molecule methane has a tetrahedral arrangement of hydrogen atoms around a central carbon, four hydrogen atoms. I'm representing the hydrogens in the plane of the blackboard with normal sorts of bonds to the hydrogens to show the three-dimensionality of the molecule. I'm representing the hydrogen that's coming out of the blackboard with a wedge bond to it. And the hydrogen that's going back into the blackboard with a dashed bond to it. In order to think about four bonds in methane, the easiest way to think about it, now you've got three p orbitals. And those p orbitals aren't the tetrahedral relationships to each other, they're at right angles to each other. The three p orbitals are coming from the carbon, the 2s, or the two p orbitals of carbon. We also will use, remember, hydrogen is bringing more electrons and four atomic orbitals for valence atomic orbitals to the table. We're also going to use the 2s atomic orbital. And so the way we think about this is that we're going to mix our 2s, our 2px, our 2py, and 2pz atomic orbitals with our four sp3 hybrid orbitals. The four sp3 hybrid orbitals point to the corners of the tetrahedron. So now it's very easy for us to think about forming the bonds in methane. We can think of forming the bonds as combining each of the sp3 orbitals, the hybrid orbitals on carbon, with a 1s orbital on hydrogen. Let me draw this out. For the sake of visibility, I'm only going to draw two of the four sp3 hybrid orbitals and two of the hydrogens. So here's one of the sp3 hybrid orbitals. Remember the p orbitals, just like we had a negative phase here, the p orbitals have a negative phase and a positive phase on them. We'll see that again when we talk about ethylene. In the sp3 hybrid orbitals, we also have a small negative phase low and a big positive phase low. Here's one of our sp3 hybrid orbitals. Here's another. I think to bind them, so I'll just put a label on this sp3. And I'll point out that there are two more that I'm not drawing. And then I'll imagine combining those sp3 orbitals with the hydrogens. So here's our hydrogen and this is the 1s atomic orbital. And I'll do the same over here. And again, although I'm not going to draw it out, we will combine the sp3 hybrid orbital and the hydrogen 1s orbital in either an additive fashion that produces net overlap or a subtractive fashion that produces negative net overlap to in turn create two molecular orbitals. And we'll only focus on the bonding orbitals. These bonding orbitals might be thought of as just pushing the hydrogen and atomic orbital together. We're making a big orbital that encompasses this and having a little bit of a negative flow. So we'll focus on this process. All right. Let's turn our attention now to a second organic molecule. This organic molecule I'm taking are archetypes of the types of structure and bonding you're going to encounter. And so each of them is demonstrating a different principle. So let's now look at ethylene, CH2, CH2. Good for now. I'm going to write it as H2C, double bond H2C. Most organic chemists and indeed I, most of the time, am going to write this as CH2, double bond CH2. Implicit in such a drawing is that the hydrogens are on the outside but they're not participating in the bonding. So we're going to use the 2S and 2BP orbitals on each carbon to make three SP2 hybrid orbitals. And for the sake of geometry, I'm going to call it the 2PX and the 2PY. So initially in our drawing we'll set the plane of the blackboard as the XY plane. That's arbitrary. So we're combining the 2S, the 2PX, and the 2PY atomic orbitals to get three SP2 hybrid orbitals. Then we'll combine those three SP2 hybrid orbitals with the hydrogen 1S orbitals to get the sigma bond framework in between each other. So let's see how I can represent this. Here's my carbon and I'll make three SP2 hybrid orbitals. The SP2 hybrid orbitals point at 120 degree angles to each other. And we will overlap the SP2 hybrid orbitals on one carbon with the hydrogen 1S. We'll do the same over here. And then we'll overlap one carbon with another carbon. And so I will draw its SP2 hybrid orbitals like so. So we're going to overlap here to form a sigma bond between the carbons. We're going to overlap with the hydrogen 1S orbital to form another sigma bond. And we're going to overlap over here. So that gives us our sigma framework of the molecule what I just drawn now is equivalent to this. And exactly, we still have upon the unused 2PZ orbitals. We still need to form our double bond. And so let's look at how we form the double bond. What I'm going to do now is shift our plane of reference for the sake of drawing. So here's the molecule on this blackboard. I'm going to go ahead onto this blackboard, bring the molecule so it's like this. In other words, now instead of having the xy plane in the blackboard, now I'm going to draw it so the xz plane is in the blackboard. I'm going to represent that sigma framework like so. With the hydrogen, remember the wedge means coming out. The dash means coming back. So here's the sigma framework of our ethylene molecule. We now have the 2PZ orbitals. And we use the 2PZ orbitals to form the pi bond. So we can combine the 2PZ orbitals. And if we overlap them in an additive fashion, meaning so that the lobes of the same phase, the positive phase and the negative phase can overlap, we get our pi molecular orbital. I'll draw that out. So the pi molecular orbital can be thought of as having a cloud above the carbons of electrons. A cloud of electrons below the carbon, you have a wave-like property where the electrons can be here. The electrons can be here. But the electrons have no electron density right in the plane of the molecule. Zero probability you have what's called a node. So you have a node in the plane of the molecule. And indeed, the pi orbital has a plane of symmetry. So I'll just label this as nodal plane. I haven't drawn it, but you also combine the p orbitals to make the pi star orbital. In the pi star orbital, you get an additional nodal plane over here, and you have an anti-bonding direction. In the drawing on the left, the p orbitals or the pi orbital are coming right out of the blackboard just like I'm holding the chalk. And I simply, for the sake of viewing, flipped the molecule. Other questions? A nodal plane? Let's go back to our p atomic orbitals. Remember from general chemistry, your p atomic orbitals, in your 2p atomic orbital, your electrons could be here. Your electrons could be here, but your electrons can't be right at the carbon. That carbon constitutes an indeed, this plane constitutes a nodal plane. It means there is a region of zero probability of binding the electrons. This is the thing that's conceptually hard to understand about orbitals. It's that we're thinking about the wave-like properties of electrons. And if you've ever held a string and made it do a second harmonic, if you've ever wiggled an oscillator in physics and had it do a second harmonic, for one point the string is going up and down, so I've stretched the string between my hands. The string is going up and down very fast. One part is going up and down. The other part is going up and down. But right at the center, there's a point where the string isn't moving. That's the second harmonic. And that's a no right in the center of that wave. What's hard to accept is you say, well, how do the electrons, if you think of them as particles, how do they get from the top to the bottom? And in thinking in a wave-like model, it's not that the electrons are one place for the other place. They're both places at the same time with varying probability. Yeah, I'm thinking on the, when you can monitor the trigonics, is that a bonding antibody and can be used for the shaking part? Ah, OK. This is a representation. So this whole structure that looks like a hamburger, where you've got a bun on top, a bun on the bottom, and a hamburger patty in the center. The whole structure is representing the molecule. These two structures, the two bonds, are representing the pi bonding orbital. And so the electrons in the pi, so we brought in two p electrons. We brought in two electrons. Those two electrons are here and they're here. And they're both places. They're never right here. The anti-bonding orbital, the pi star molecular orbital, I haven't drawn. The pi star molecular orbital looks something like this. And so in addition to having electrons having a nodal plane here, you have a nodal plane at the axis at the center of the molecules. This is your representation of your pi star molecular orbital and ethylene. So what I've done here, just as we ignored our anti-bonding orbitals that were created in doing our overlap here, just as we've ignored our anti-bonding orbitals here, we're ignoring them in this drawing. They exist, but there are no electrons in the anti-bonding molecular orbitals. So we're saying, let's for the sake of simplicity, only draw representations of the bonding molecule. Other questions. These are good. This is the hard stuff for people in sexual. The pi orbitals are in the plane of blackboard, but they also go out. So think of it as a cloud. Think of this like as a rain cloud. Centered in the blackboard, but fluffily sticking out, sticking back. So it's a big region where the electrons can be. All right. Let us try one more archetype of an organic molecule. We'll take the centerline. And once again, for starters, they're going to be good. And right now, the molecule, in a way that's a little bit more intuitive, you'll probably see it written in the future as C-H triple bond C-H rather than H-C triple bond C-H. But let me start by making it simpler. All right. In order to make the structure of the settling, we're going to do the same type of things that we did for ethylene. We're first going to make the sigma framework with hybrid S-P orbitals now. And then we're going to make the pi bond, pi bonds, the two pi bonds, using the remaining two P orbitals. So we'll take the 2S, and I'll say the 2PY for the reference frame I've been drawing, atomic orbitals on carbon. And we'll make two S-P hybrid orbitals. And we'll combine them again with each other and with the hydrogen, and the S-Syntonic orbitals to make the sigma bond framework. And then we'll take the remaining P orbitals, which in this case are the 2PX and the 2PZ orbitals, and that will lead to the two pi bonds. And I'll give a little bit of an abbreviated drawing here, where now all I've done is to overlap. It's going to be a little hard to see, but actually I think what I'm going to do is say we're going to make, here's our one S-P. It's hard to draw because our other S-P is like this. So basically on the same carbon you have two S-P's, one pointing one way, one pointing the other. So I'm just going to draw our sigma bond framework out of the combination of the S-P's with each other and with the hydrogen one S orbitals. So this is the carbon on the left. I've pointed one S-P at the S-P on the other carbon. I've used the other S-P to make a bond to the hydrogen. And then I'm just going to combine, here's our 2PX, and then I'm going to combine the 2PX. So that will be to the pi bond. And then here's our 2PZ, and I've got to try to represent three dimensions in two, which is always very hard. So the PZ is pointing out. The PZ is pointing out. And I will combine those much as we did on the right hand blackboard and our carbon line bond. Let's take another look. Thoughts or questions on settling? I was wondering, why does it matter if one becomes the pi bond of 2PX, 2PY, and 2PZ? Great question. Does it matter which ones become the pi bond, the 2PX, the 2PY, or the 2PZ? No, it's arbitrary based on my choice of the reference frame here. So based on my drawing and saying blackboard's the XY plane, we could have easily written the molecule in a different orientation or center axes differently. So we combine, say, the PY and the PZ or the PX and the PY and use those to make the pi bond. So there's no specific order to have the pi bond? There's no specific order. The main thing to keep in mind, so this is a good question, the main thing to keep in mind is we're using that sigma, that 2S orbital to make our sigma framework. That's the low energy one. That's relatively low in energy. The 2PX, the 2PY, and the 2PZ are all equal in energy and therefore equivalent. But we definitely, because the sigma framework produces the best overlap, we definitely want to use the 2S, the lowest energy atomic orbital in making up that sigma framework. 2SP orbitals, are those total or some of each of the carbon and the 2S, how many S-P orbitals do you have total? How many S-P orbitals do we have total? This carbon brings 2S-P orbitals. This carbon brings 2S-P orbitals, so we have four total. We use one of those S-P hybrid orbitals on this carbon to make the CH bond. We use the other one to make the CC bond. Then we use one of the 2S orbitals on this carbon to make the CH bond and one to make the CC bond. I'm sorry? I'm not saying I want to ask. You said you have two S-P orbitals. That's the problem with more carbon. How do the two S-P's overlap? So how do we make the carbon carbon sigma bond? So we make the carbon sigma bond by overlapping this S-P and this S-P. And when we overlap them, we get a region of high probability of having the electrons that's right in the center of the two carbons. And then you also get an anti-bonding orbital, which we are ignoring through the stages. All right, let's do one last thing. And let's take a look at a relationship now between bond hybridization, between orbital hybridization and bond strength, and between bond order and bond strength. So let's start with the CH bond strength. The strength of a bond is literally how much energy it takes to rip the bond into two equal halves. By equal halves, you may have different atoms, but I mean that each atom gets one electron. So if we have a CH bond, we rip it into C dot plus H dot. And I'm making this distinction right now because in the next lecture, we're going to start to talk about acidity. And in acidity, we rip apart bonds unequally. We take off not a hydrogen atom, but an H plus, leaving behind a lone pair of electrons. And there, the rules are very different. But let's look at bond strength where we rip apart bond apart homolytically equally, rather than heterolytically unequally. The strength of a CSP3 hydrogen bond, bond to hydrogen, is about 98 kilocalories per mole. What's interesting and what's important is that if we use an SP2 hybrid orbital in making that bond, the CH bond gets stronger. The energy to rip that bond apart homolytically, to break it into a carbon dot and a hydrogen dot, goes up to 104 kilocalories per mole. Why is that? Remember, I said that the S orbital, it goes up from 98 kilocalories to 104 kilocalories per mole. In other words, if I rip a CH bond in methane, it takes 98 kilocalories per mole of energy. If I rip a CH bond in ethylene, it takes 104 kilocalories per mole of energy. Exactly because they're in a lower energy orbital, the SP2 is lower in energy than the SP3Y. More stable, it has more S character. Remember, we said S is lower than P. The SP3 orbital has 25% S character and 75% of the higher energy P character. The SP orbital has 33% of the lower energy S character and 66 or 66.66% of the higher energy P character. So we're in a lower energy atomic orbital. It makes a lower energy molecular orbital when we rip that bond apart. We have to break a more stable bond. Finally, if we look at a CSP hydrogen bond, that bond is even more stable. It's 125 kilocalories per mole to rip that bond apart in a homolytic fashion to rip it apart to get C dot and H dot. You'll later learn that that bond actually is exceptionally acidic to rip apart in a heterolytic fashion. That's a different story. Let's take a look at single, double, and triple bonds. We saw a single bond in methane, and we've seen single bonds in ethane. I'll take carbon-carbon single bonds, because that's going to give us a nice comparison. The carbon-carbon single bond is 88 kilocalories per mole. The carbon-carbon double bond in ethane is 152 kilocalories per mole. In other words, the extra pi bond in ethane adds about 60 kilocalories per mole stability. I'll say about 60 kilocalories per mole. Why am I being a little dicey with the numbers? Well, the sigma bond's a little stronger in ethane, too, because in the sigma bond in ethane, we're using those stronger sp2 hybrid orbitals. We're making a stronger sigma bond. So we don't know the exact difference, but the difference is about 60 kilocalories per mole. Now, this is interesting because it says, wow, the pi bond isn't as strong as the sigma bond, and that's consistent with what we see over here. Those electrons aren't shared as well between the carbons. They're not directly between them. They're above and below. And then just to complete the set, we'll look at the settling, and we'll look at the triple bond, and that's 200 kilocalories per mole. And so adding yet another pi bond increases the stability, but not as much as by a sigma bond. The sigma bond is giving us about 60. The third pi bond is giving us somewhere on the order of 10. The sigma bond is giving us about 90. The third pi bond is giving us about 50. All right, next time we'll talk about molecular geometry, and then we're going to move on to talk about chapter 2, the strength, the body, and the strength of acids and bases.
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -0:55 Orbital-Based Models of Structure and Bonding -1:53 Molecular Orbitals -3:39 Orbitals of Molecular Hydrogen -10:36 Orbital Energy Diagram of Hydrogen -15:34 Hybrid Orbitals of Methane -22:09 Ethylene Orbitals -35:11 Acetylene Orbitals -39:39 Student Questions -43:20 Bond Strength
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10.5446/19382 (DOI)
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Good morning. I was chagriding and watching myself on the video of yesterday's lecture as I managed to owe my brain, was on the very last point I wanted to be managing to stumble over something involving the reaction of Sodium added and Sodium is satellite or snog with top comment. So there will be a problem in the discussion section this coming week. It's actually going to address this issue in a reaction of in a slightly different reaction that illustrates the same point anyway as we'll make things very clear to you. What I'd like to talk about today is Lewis acids, Lewis bases and their relationship to organic reaction mechanisms and we'll introduce the concept of nucleophiles and electrophiles that will be central to all of the remaining sequence, the A, B and C sequence of the organic chemistry course. So, a Lewis acid is an electron pair acceptor. And a Lewis base is an electron pair donor. In a writer, an example of a Lewis acid, Lewis base reaction that's probably not so dissimilar to things that you've seen in general chemistry. Maybe one of the molecules is an organic molecule but maybe you've even seen this reaction before. So let's look at the reaction of boron tri fluoride BF3. This is diethyl ether. It's called boron tri fluoride etherate BF3-ET2O or ET2O-BF3. I'll write out the name of this complex. Now, regardless of whether you've seen this precise reaction or similar reaction to it in the past, what I'd now like to do is to think about this reaction with the same tools that I, Buck and Johnny use every day in thinking about organic reactivity and that is the flow of electrons associated with the formation of bonds. So I'm going to write out a full Lewis structure of boron tri fluoride and a Lewis structure of diethyl ether that focuses on the oxygen atom. And I'll try to be good about remembering to draw in all my lone pairs of electrons as at least at this point in your education I expect the US are starting to get comfortable with writing reactions. So here's boron tri fluoride. Here's diethyl ether. I'll draw in my lone pairs of electrons. The Lewis, the boron tri fluoride accepts a pair of electrons from the diethyl ether. So it is acting as a Lewis acid. Boron doesn't have a complete octet except by resonance you can write structures in which it does have a complete octet. But if you write one charge resonance structure it has only, or resonance structure with no formal charges, it has only six electrons around the boron. In other words the boron is not a happy and wants an octet. The diethyl ether has electrons to share. It acts as a Lewis base. The sake of consistency I will not capitalize the word base. Electrons flow from the diethyl ether. The way we write this is we show the electrons flowing from the lone pair. We show our curved arrow beginning at the lone pair and they go to the boron, they go to the atom. We have, like we showed above, an equilibrium. And now we form our complex. And I'll write it, it doesn't matter which I write on the right or which I write on the left. I'll write it. So the CH2, CH3 is coming off the oxygen. There's a lone pair on the oxygen. Now we have a formal positive charge on the oxygen, formal negative charge on the boron. You'll notice that we have not created any net charge, we haven't created any overall charge. We started with two uncharged molecules. We end up with an uncharged species. And I'll complete my drawing by being a good person and putting in my lone pairs of electrons on the boron. Thoughts or questions? Now one of the things that's confusing the first time around, we talked about different models of reactivity. We talked about different models for structure and bonding. Here we're talking about different models of acidity. In the last two lectures we talked about Bronsted acids in various forms. So what's the relationship? In terms of Lewis acid, it's just a more inclusive model for acid. In other words, all Bronsted acids are Lewis acids. And all Bronsted bases are Lewis bases. And I'll illustrate this by returning to one of the reactions we had seen before. And of ammonium ion NH4 plus, with hydroxide ion OH minus. Let's look at this reaction. The reaction, of course, is an equilibrium to form ammonia and to form water. So what's happening in this reaction is electrons are flowing from the hydroxide to the proton on the nitrogen. That proton is accepting the electron pair, but of course it can't accept the electron pair and have four electrons around it. It needs to relinquish two bits electrons to nitrogen. And you'll notice how I show that. I show the electrons going from the pair of electrons that comprise the bond, one to the nitrogen atom, so that we end up with a lone pair of electrons on the nitrogen. And now we end up with a new bond to water associated with this group of electrons or a new bond to hydrogen. So this molecule here, the ammonium, is acting as a Bronsted acid because it's giving up a proton. But it's also acting as a Lewis acid because if, or at least the hydrogen on it are accepting a pair of electrons, the hydroxide in turn is acting as a Bronsted base. It's accepting a proton, but it's also acting as a Lewis base. Thoughts? Let's now play with a distinctly organic reaction. And what's nice is you'll start to see that the patterns really are very similar in all of these reactions that we're looking at. So the reaction that we'll look at is the reaction of a tert-butyl carbocation with water. This week's discussion section problems feature a tertiary butyl carbocation. I'll write out the name. These names will eventually start to flow off your tongue. Tert is short for tertiary. Sometimes you'll see it written as just T-butyl. We write it with a hyphen to show that it's connected, that it's modifying butyl. And carbocation means a cation, a positive ion, that's centered on carbon. Hence the positive charge on carbon. We'll look at its reaction with water. Ultimately I'm going to show this as part of a bigger reaction called acid-catalyzed alkene hydration. This is one step in the mechanism of acid-catalyzed alkene hydration. But right now I'd just like to focus on one step on this Lewis acid, Lewis base step of the reaction. Where now our water is acting as a Lewis base, our tert-butyl carbocation is acting as a Lewis acid in this reversible equilibrium reaction. What's happening? Well, as I said, there's fantastic analogy for about the form of bond between water and the tert-butyl carbocation. I'll show you how this goes. Electrons flow from the water to the carbon atom. Remember your lone pair, your current arrow should start at the lone pair and should end up on an atom reforming a bond here. And the resulting product of this reaction is like so. It's protonated tert-butanol. As I said, we're acting here our water. I'll come down to the other blackboard. It's acting as a Lewis base. The tert-butyl carbocation is acting as a Lewis acid. And really this reaction is the exact same reaction we see on the other blackboard. The tert-butyl carbocation has only six electrons around carbon. Boron trifluoride has only six electrons around boron. Both of them, both the tert-butyl carbocation and the boron trifluoride, would like to get a complete test. I talked before about how there are many analogies between water and alcohols. There are some analogies between alcohols and ethers in their reactivity. Diethyl ether is like water with two carbons, one on each side. It still has, although it doesn't have an OH group, it still has a lone pair of electrons on oxygen. So it can act like a Lewis base, as we see in this reaction. Organic chemists have special names. I know we have a lot of names here. They just start to blow off your tongue after you use them and speak them for a while. Organic chemists have special names for Lewis acids and Lewis bases in organic reactions. I think I've mentioned them already. Organic chemists would call a Lewis base, a Lewis acid rather, in this reaction, an electrophile. Electrophile means something that likes electrons. Phyllis, I think, is Greek. So anyway, very simply, you have a positive charge on the carbon. You have an incomplete octet. It wants electrons. The Lewis base has electrons to spare, and so we call it a nucleophile. That may not be as obvious, but when you think about it, it makes sense. It likes something with a positive charge. It likes something that's like a nucleus. And so an organic chemist would call, I'll put these in parentheses just to say that we're using one or the other, an organic chemist would say, ah, this is an example of a reaction of an electrophile interbubicarbocation with a nucleophile water. All right. Let us now use this one reaction and use the concepts of acid-base chemistry. To look at a complete organic reaction mechanism, we're going to look at the reaction mechanism for acid-catalyzed alkene hydration. We're going to spend some time today talking about this. We're going to go through it very slowly. We're going to look at it both forward and in reverse and see the roles of acids and bases in this reaction. The example that I'll give us is the reaction of isobutylene with water. We'll write out the name of these molecules. We'll get more about nomenclature as we move on to the chapters on alkenes and alkanes. This molecule is called isobutylene. It's also called two-methylpropene. Isobutylene is the common name. Two-methylpropene is what we would call the IOPAC name. Isobutylene reacts with water, but not if you just mix them, but rather if you have an acid catalyst. I'll write this as H3O plus in H2O. I'll point out that the H3O plus is a catalyst. As I've said before, you can't go into the stock room and get a bottle of H3O plus. You always form H3O plus by adding a strong acid to water. If I wanted to do this reaction and wanted a catalyst, I would take some sulfuric acid and put it into water and that, of course, would make H3O plus and HSO4 minus by sulfate NIN. The overall product of this reaction is an equilibrium. It goes forward and it goes reverse. Again, I'll write out the name of the reaction. We're running out of space on this blackboard. I'll write it down here. You'll hear it referred to as tertbutanol. You'll hear it referred to as tertbutyl alcohol. Both of those are common names. You may also see it referred to as two-methyl, hyphen 2, hyphen propanol. That's the IUPAC name. It's so often the case when I'm just writing out a reaction, when my focus is on reactants and on products, I'm not going to be showing you all of the lone pairs of electrons and I won't be focusing on formal charges so much, although it's useful to write them in. What I'm doing here is showing the overall reaction. Now what I'm going to do is to write out the three-step reaction mechanism for this reaction. Let's begin. Here's our isobutylene. Isobutylene has some electrons. It has electrons in the sigma bonds, of course, but most importantly it has electrons in the pi bond. For that reason, it can easily act as a nucleophile. It can act as a Lewis base. It can act to react with something that wants electrons. Now we've already seen examples in which things bearing protons have acted as acids. We saw an example of ammonium, where the ammonium ion donated a proton. We had a positive charge on the ammonium ion and it was reasonably willing to give up that proton when we had a strong base where we had hydroxide and anion. In this case, this is not a strong Lewis base. The alkene is a recluous base. It's relatively heavy. But we do have one strong acid present and that acid is hydronium ion. We're going to see how the hydronium ion acts as a catalyst in this reaction. We're going to consume it in the first step of the reaction. You'll say, oh my goodness, we're consuming a catalyst. It can't be a catalyst. And then at the very end, we're going to regenerate it so that no hydronium ion is actually consumed in the overall reaction. Here's our hydronium ion. We're all very comfortable with the idea that a hydronium ion is an acid. We're going to show electrons flowing from our Lewis base to our Lewis acid. Just as we had done with hydroxide and ammonium, we draw our curved arrows starting at the source of electrons. In this case, it's not a lone pair, but rather an eye bond, another group of place for electrons to come from. We show electrons going to our proton on the hydronium ion and in turn, we can't have four electrons around that proton, so we push our electrons back onto the oxygen giving us water. All of the steps in this reaction are reversible equilibrium. We end up with that proton now attached to this carbon atom, so we've gone from a carbon with two hydrogens around it to a carbon with three hydrogens around it. We've got a third fuel carbocation, two more methyl groups that I simply, for the sake of simplicity, won't draw out as full Lewis structures. And finally, we have our water molecule. We've put our lone pair back onto the oxygen atom. Step one. Step two, we've seen over on the left-hand blackboard. I'm going to write it again. Here's our third fuel carbocation. Now I will bother to write the full Lewis expansion of the methyl group because at this point we don't need to concern ourselves with it. Our third fuel carbocation reacts with water. Electrons flow from the oxygen atom to the carbon atom just as we had seen before. We have an equilibrium. Just as I had drawn before, we have our protonated third fuel carbocation, our protonated third fuel null. It doesn't matter whether I draw this hydrogen pointing down or I draw this hydrogen pointing up. In all cases, we're representing the same thing, tetra-egro-oxygen atom, which we just used the vertices of the square to show, or across to show the positions of the oxygen atoms. Alright, we're almost at our product. We have just one last thing we have to do. Of course, we don't have our catalyst back and I promised you that you're going to regenerate your catalyst at the end of this process. We're in water. Water protons flow on, protons flow off. Water can act as a Lewis base. We have lots of water present. Here's our protonated third fuel null again. For all intents and purposes, water is a comparable Lewis base to the tert-butanol, or to put it another way, hydronium is just about the same strength of Lewis acid as is protonated tert-butanol. We have lots and lots of water present and so water happily flux off our proton. Again, we show electrons going from the lone pair to the hydrogen, electrons going back onto the oxygen. I won't put the same, not drowning things too much, right down over here. Here's our hydronium ion. Thoughts or questions? And when in biology? So here I said that water, the hydronium ion acts as a catalyst. We've reduced it in the first step. We've regenerated it in the last step. When in biology, you learn about enzymes, it's actually the same thing. In the first step of a detailed reaction mechanism of an enzyme, the enzyme is changed in its interaction with the substrate. And by the end, your enzyme is regenerated and your product is released and this occurs thousands and thousands of times. And here too, just a little bit of acid can catalyze the formation of thousands and thousands of molecules of tert-butanol. How do you know if you're going to do that? Ah, how do you know? Well, we're learning pathways and you're going to become more familiar. But what's a good guideline? We have three different things present here. I subutilate water and hydronium ion. We think about what's the nucleophile, what's the electrophile? Well, I subutilate essentially can only be a nucleophile. That water can accept a proton, hydronium ion can give up a proton, that's a degenerate reaction, hydronium ion S is a proton of water and that occurs thousands and thousands and thousands of times. So in the end, we look, wait a second, the best nucleophile is going to be, I subutilate the best electrophile is going to be hydronium ion. The nucleophile gives its electrons in an acid-base reaction to the hydronium ion and we store it down the pathway. Then we look, we say, wait a second, we have a tert-butyl carbocation. That tert-butyl carbocation is unhappy. It walks electrons. Who has the electrons? Ah, water has some electrons. The water can give the electrons back to the tert-butyl carbocation and then we're over here and we say, ah, protons can get cast around. Water has electrons, we have lots of water, it happily takes the proton off. As I said, this is an equilibrium reaction and what I'd like us to do now is to look at the reverse reaction. Because technically all reactions that can go forward can go in reverse as well. In principle, some end up going so far to the right that you never see the reverse reaction. The reverse reaction is acid-catalyzed alcohol dehydration. And I'll write out the overall equation and then a detailed reaction mechanism. The overall equation, all I'm going to do is take what's on the right of this arrow and bring it to the left and take what's on the left of this arrow and bring it to the right. In other words, I'll take my tert-butanol on the left. I'll show my catalyst H3O plus my solvent water. Over the arrow is typically where you show reagents and under the arrow is typically where you show solvents in writing reactions as organic chemists think about them. The left is typically where one shows product and the other is where one shows product. So here's our isobnudeline and the other product of this reaction is water. Reactions go by the same pathway in forward and reverse. Organic chemists have a fancy name for this reaction. It's called the principle of microstopic reversibility. And I'll write it out for you. This makes sense. Reactions take the path of least resistance. They take the shortest path and if you were to say drive from where we are now to let's say Balboa Peninsula, what I'd do is I'd get on Bison and go to the 73 and go to the 55 and take the 55 all the way down across the PCH to Balboa Peninsula. And coming back the shortest path, the lowest energy path, the least resistant path would be the exact same. I would take the road from Balboa Peninsula along across the PCH through Newport, through Costa Mesa to the 55 to the 73 and back here. So we're going to write out the mechanism for the reverse reaction. The reaction ended with the deprotonation of protonated tert-butanol. And so the very first step in the reverse reaction is just going to be the protonation of tert-butanol. In other words, here's tert-butanol. Here's our hydronium ion. The hydronium ion acts as an acid, both a Brunsted acid and a Lewis acid. It gives up the proton to the oxygen atom of tert-butanol. We already discussed how this is an equilibrium where protons come on, protons go off. I show the same notation of curved arrows to show the flow of electrons. I have an equilibrium. We get protonated tert-butanol in water. Just as in the forward reaction where the first step, oh my God, we lost our catalyst. Here in the first step, our catalyst is consumed in the last step. We have time to be recreated and of course the last step is going to be the same. Let me, I think what I'm going to do is simply leave these two blackboards up so you can see what I'm writing and I'll return to this blackboard over here. Yes. Do all of what have you. The examples today? Yeah. And in fact, acids and bases are so central in organic chemistry that you will see many, many reactions as we get to carbonyl chemistry where a hydronium ion is acting as a catalyst. Of course there are other reactive species. There are hydroxide ion. We just saw an example with boron and hyaluride reacting with diapoleether. But you'll notice that the steam of species with electrons and species that want electrons of nucleophiles and electrophiles continues to change again. Well, that's a good question. What I tell you, you're going to learn it and you're going to become more and more, you're going to learn about reagents a little bit in this course. Reagents are chemicals that one adds in reactions of organic molecules and more of the 51B course, the 51C course. And you're going to learn, oh yes, a graveyard reagent reacts with a carbonyl compound and after aqueous workup with a little bit of acid forms an alcohol. All right. Next step of the mechanism. And this is hard because you haven't seen this before. We're learning things that matter new. Next step of the mechanism is the exact reverse of the middle step. We have protonated tert-butanol. Our protonated tert-butanol formed in that middle step on the right-hand blackboard. And now it's going to break apart. It formed from a carbocation and water. In the reverse reaction, it breaks apart to a carbocation and water. Electrons flow from the bond between oxygen and the carbon atom to the oxygen. We have an equilibrium. We generate the tert-butanol carbocation. We have our Lewis acid and we generate water, our Lewis base. Now we're headed on the path way back to our alkene. To head back to the alkene, remember we started in the forward reaction in the very first step of acid-catalyzed alkene hydration by placing a proton, by having a proton react with the double bond of isobulene, adding a proton. In this case, we have to take away a proton. And this is the step that students, particularly the first time around, have the toughest time seeing. Going to focus on one of our three methyl groups. They're all equivalent. It doesn't matter which one I focus on. I'll focus on the top one. What's going to happen in this step is we're going to lose one of these protons and we're going to take the electrons that held on to the proton and push it into between the two carbon atoms to form a double bond. It makes sense that this would want to happen. It makes sense that this would want to happen because this carbon atom is unhappy. It doesn't have a complete octet. And it will do what it needs to to get that complete octet. Later on, you're going to learn about a concept called hyperconjugation, in which you will learn that that carbon atom can beg and borrow electrons in order to feel a little bit less unhappy. I introduced this concept when I talked about the methyl carbocation the other day and I said, well, you're never going to see a methyl carbocation. It's going to be unstable. But if you have some more carbon atoms around there, those carbon atoms can donate electrons if you have some more CH groups around there. They can donate electrons. And that's what hyperconjugation is. That's begging. That's borrowing. Now we're going to see stealing. And in going from the tertiary carbocation, the positive charge is going to steal this pair of electrons from the CH bond, but it will be aided and abetted by a cooperating water molecule. Our water molecule has electrons. It takes the proton. The proton donates electrons in between the two carbon atoms. And we get back our isobutylene and our protonated water and our hydronium atoms. And so in spite of this minor petty theft, all is right in the world at the end. The carbon has a complete octet. Our catalyst, which was taken away at the very first step of the acid-catalyzed alkene dehydration, is regenerated at the end. All right. Well, we will pick up next time talking about Chapter 2, talking about L-pane, Chapter 3, talking about L-pane and learning some of the functional groups next in Chapter 3, learning about characteristic functional groups and their reactions.
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -1:15 Lewis Acids and Bases -2:21 BF3 Example -8:49 NH4+ Example -12:41 Tert-Butyl Carbocation Example -19:15 Acid-Catalyzed Alkene Hydration -34:49 Acid-Catalyzed Alcohol Dehydration -37:26 Principal of Microscopic Reversibility -39:59 Tert-Butanol Example
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10.5446/19385 (DOI)
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All right. Good morning. So we are one more quiz through completing this course successfully. As much as I like to joke, you should fall behind early. So you have longer to catch up. I know it's truly hard to keep on top of things. And one of the reasons we have these quizzes is to help, in addition to integrating the homework and the discussion sections, is to help us keep on top of the material. Because 10 weeks really does go by very, very quickly. Well, today we're going to start on chapter 4 and begin discussing alkanes. In some ways, alkanes are the least interesting of organic molecules. But they're also going to serve as a platform for beginning to discuss stereochemistry and for discussing confirmations of molecules, the three-dimensional shapes of molecules. So we're going to have a lot of meat in this chapter. This is the chapter that you're going to start to use your molecular models, begin to play with them like we've seen in the videos. We're going to be using rulers to help us and to help integrate the exercises in the chapter with the discussion section and the midterm exam. If you haven't already done so, you should get yourself a good ruler that measures in centimeters, one that's a full one foot long, 30 centimeters in length, so that you'll be prepared to answer questions that are asked of you involving the molecular models. All right, well, let's begin what will be four lectures on the chapter on alkanes. So alkanes are saturated hydrocarbons. They have a general formula of Cn, N being an integral number of carbons, H2N plus 2. And we're also going to lump into our discussion of alkanes. We'll also lump in cycloalkanes. These are saturated hydrocarbons with a ring in them. As such, they have two fewer hydrogens. You basically connect the end of a chain together at a position where two hydrogens would be to get a ring. So you have a general formula Cn, H2N. As an example of an alkane, I'll just take octane. You've heard of octane before, of course, in terms of the octane number for gasoline. The octane number is actually not determined by the parent compound octane, but rather by a branched isomer of octane. What octane gives your car is not power. All of the hydrocarbons burn with about the same amount of energy, but rather what octane, or more specifically, this branched isomer of octane does, is it burns in a way that causes your engine not to knock. So on an octane scale, octane is 100, and heptane, a 7-carbon alkane, has an octane number of zero. Anyway, octane and all of its isomers have a formula C8H18. And by comparison, we'll take as an example for a cycloalkane, we'll take cyclohexane. Cyclohexane is going to become a good friend of ours because it has an interesting conformation, an interesting shape with very regular properties, and this ring can be found in various steroids. Steroids, of course, are both compounds that people take illicitly for sports performance, but they're also the estrogen and androgen sex hormones. Anyway, cyclohexane itself has a formula C6H12. Hydrocarbons and alkanes in particular come from petroleum. There are vast quantities under the ground, and unfortunately, mostly they're used as fuel. So we burn 80% of the alkanes that are produced, and this is really a shame given how valuable these are. These are the starting feedstocks for all sorts of chemicals, the plastics, the nylon in your backpack, the polyesters and the like in the chairs that you're sitting on are all ultimately derived from petroleum and many of them from alkanes and from cycloalkanes. So although they're mostly used as fuel, I'll write that they're important feedstocks for chemicals and drugs. Plastics as well. I'll just write, et cetera, because they're just about everything you can think of as some component of alkanes in it, almost every chemical compound you can think of or material you can think of probably has had some component of alkanes and petroleum in the making of them. Since we burn them, I'll write one chemical equation. You're actually not going to see that many chemical reactions of alkanes this year. You'll see some halogenation reactions. But in a day-to-day use, when you take your car and you put a mixture of hydrocarbons as well as a few ethers that contain octane in your car and you burn it with oxygen, we get carbon dioxide in water. A lot of times in organic chemistry, we don't balance equations. But I can easily balance this. We generate eight molecules of carbon dioxide. We generate nine molecules of water. And in order to do this, of course, we need 12 and a half molecules of oxygen. All right. I'd like to spend a few minutes, not too long, talking about the various alkanes and about the nomenclature of alkanes, that is how we name them. Also, we'll talk about the properties. It seems that any basic cultural literacy probably should know the physical and chemical properties of the first few alkanes. We've talked about methane, CH4 before. It's a gas, very low boiling gas. I think I mentioned in the past it has a boiling point of negative 162 degrees Celsius. So we move along in the chain, the series, we get ethane. I'll write out its molecular formula since we talked about C2, CnH2n plus 2. Ethane is C2H6. In other words, it's CH3. CH3. Ethane is a gas, but it has more Van der Waals interactions, so it boils at a higher temperature. The boiling point of ethane is negative 89. Moving along the series, oh, and I should write out the name here. Moving along the series, propane, CH3H8. In other words, CH3, CH2, CH3. Propane is also a gas, but propane is interesting because by the time you get to propane, if you apply enough pressure at room temperature, you can liquefy it. So you can put a lot of it in a gas tank. Its boiling point is not so low. It's negative 42 degrees Celsius, which is temperatures that you get on, well, you can get access to on Earth. But what that means, the fact that you can liquefy it, and the fact that the boiling point isn't too low, is that it's a gas at 10 atmospheres, a liquid at 10 atmospheres. An atmosphere is 15 pounds per square inch. So if you look on your car tires, or you go to the gas station and you put air in your car tires, you're putting in about 30 psi, about 2 atmospheres of pressure. If you have a bicycle and you have racing tires on it, you may be putting in 90 psi or more 6 atmospheres of pressure. So the pressure in a propane tank is not that much higher than you would access from a handheld bicycle pump. Continuing along the series, butane C4H10, we should get in the habit of writing out these structures in the skeletal notation, so I'm going to do that for butane. Butane's also a gas. But its boiling point is negative 1 degree Celsius, so now it would liquefy in the freezer that you might have in your home or in your dorm room. Of course, if you smoke, you probably butane lighters, and you see liquid butane in those lighters. Butane is a liquid at 2 atmospheres, at room temperature. So the pressure in those butane lighters is the same as the pressure in your car tires. If we continue along the series of alkanes, pentane C5H12, now pentane's a liquid. It's a low boiling liquid. So we've gone from a gas to a liquid and adding one carbon, but its boiling point is just 36 degrees. So if I were to take a few ounces of pentane and spill it on the floor here, it would evaporate in just about no time. Not only is the boiling point low, but because we just have van der Waals forces between the molecules, the heat of vaporization is low. That means it doesn't take a lot of energy to boil an ounce of it and turn it to gas. It takes a lot more energy to boil an ounce of water and to turn it to gas because the molecules stick together. One of the things we're getting as we see these molecules is we're also getting the names of them. So the first four names basically are trivial, common names. We talked before about how butane comes from butter. Ethane comes from ether from the air. Methane, it turns out, has a connection to wood. But beyond that, we get the systematic roots derived from Greek or Latin. So pentane, you can think pentagon. The next one, hexane C4C6H14, hexane. You can think like a hexagon if you want to remember these names. The names all become systematic. It's a liquid. Its boiling point is 69 degrees. Now the other cool thing is when you have a series of numbers like this, you can start to come up with some reasonable predictions. So if I ask you the boiling point of heptane, you might say, well, I don't know the boiling point of heptane. But I can see that as we're moving through this series, the difference between the boiling points is just a little over 30 degrees and it's getting closer together. So I could probably extrapolate that the boiling point of heptane would be somewhere just about 100 degrees Celsius. So it's sort of cool you can figure out the various trends. All right. If we go through our name, C7H16 is heptane. We saw C8H18 octane. It's probably worth knowing how to count to about 12 and maybe knowing 20, number 20 beyond that. C9H20 is nonane, NONNE, C10H22 is decane. That's easy. Easy if you remember the C when you're talking and writing. Decanes like 10. C11. I'll just give you two more and then I'll give you number 20. C11H24 is undecane. And so you see the principle becomes we're going to add a prefix to specify that it's one more than decane. C12H26 is dodecane. And I'll give you one more just in case you hear it. Icosane is C20H22, H42, EICOSANE. And a couple of things that I should add. So our alkanes up through C17 are liquids. They're light liquids. So let me jot this down over here. So C5H12 pentane through heptadecane up above C17. There are solids. They're kind of waxy solids. In fact, if you push your finger against them, they're soft. It's not a surprise. Paraphen wax is a mixture of high chain length, long chain length alkanes. And in fact, all of the alkanes are known as the paraffins. That's the family of compounds to which they belong. The compounds are all light. They're low density. Less than a gram per mil. That means if you put dodecane on water and water, not only will they not mix, but the dodecane will float to the surface. All right. One of the things that alkanes give us a chance to do is to introduce ourselves to the concept of isomers. This concept already came up when we started to look at Lewis structures of various molecules. And I remember when I asked people the structure of methyl azide, a lot of people struggled to write a structure. And some people came up with a Lewis structure, but it wasn't methyl azide. And this was the first chance we got to see that there can be different covalent connectivities of atoms, different what we call constitutional isomers. So isomers are molecules with the same molecular formula but different structure. And there are two main classes of isomers. One is constitutional isomers. Constitutional isomers are isomers that with different connectivity. We've already seen some examples, but I'm going to take us through and take us through a little bit of systematic thinking. The other ones that are a little harder to understand and we'll get to them in just a couple of lectures are stereoisomers. And this is where your models really shine for helping to get things into your head. Stereoisomers have the same connectivity. But a different three-dimensional structure. We'll get to this concept with enantiomers and diastereomers, but if you want to know what I mean by the same connectivity of but a different structure, for now just look at your right hand and look at your left hand. And both hands have all of the fingers and thumb connected in the same type of places, and yet they're not the same. That's what I mean by the same connectivity but a different structure. We'll also see something that would be like with your fingers pointing in different direction, and that's a type of stereoisomer called a diastereomer. What you're seeing for your hands are a type of stereoisomer called an enantiomer. All right. So, for isomers, let's start with the isomers of butane and pentane, and then we'll talk about some other. If we make a linear chain, CH3, CH2, CH2, CH3, where I draw it as a zigzag structure, of course, you have a molecule that's called butane. You'll sometimes see it referred to as inbutane. N is a prefix. That means normal. And so, inbutane is just a way of saying, yeah, I mean butane, not any isomer of it. I mean the straight chain compound. For contrast, let me give you the one isomer of butane, CH3, CH3 with a methyl group off of the CH group, off of the what we call a methine group. So, if I want to write this out in shorthand, I'll just write it like this. This isomer is not surprisingly called isobutane, since it's the only isomer of butane. We know what we're talking about when you'd say isobutane. These types of names are what we call common names. I've mentioned them before. The more systematic name says, oh, this molecule has a three carbon chain, so it is a derivative of propane. We would call it two methyl propane. Now, let's do the same thing with pentane. We're going to get three isomers for pentane. I'll write them out in shorthand. And what I want to get us used to is the thought process for generating different isomers. So, pentane is three isomers, and the way I think about it is to say, okay, we have pentane here or in pentane. If I imagine taking off one methyl group, so I'm going to permute systematically through all the different possibilities. If I took off one methyl group and I wanted to put it somewhere, where could I put it? Well, I could put it here or I could put it here. No matter where I put it, I get the same one. I get the same molecule. This molecule is called isopentane. Systematically, it would be two methyl butane. And if you continue to think, well, I can't take off an ethyl group and do anything because if I take off an ethyl group, that's just going to get me back to isopentane if I reconnect it. But if I take off another methyl group, in other words, cut our chain down from five to four, and then from four to three, the only place I can put the methyl group to get something unique is this molecule. We've seen this molecule before. It's called neopentane. And its systematic name, as I've written before, is 2,2-dimethyl propane. So as we go along the alkanes, the number of isomers increases dramatically. Butane, I'm going to write this all out just so you can see the whole trend. Butane has two constitutional isomers. Pentane, we saw three. Phexane has five. Heptane has nine. And if you want a good exercise, this is one that's worth doing in your next class if it's boring, is to try to write out. Now, in this one, in the last five minutes if we're boring, to try to write out all nine constitutional isomers of heptane. I did this yesterday at the Blackboard as I was thinking about what I was going to say today and started to realize, oh, I need to scratch my head for a moment. But, yep, there are nine of them. And it's a good exercise because it's just the right number, not to be tedious, and to get you into the right mental processes. If we go up to octane, now we have 18. The numbers really increase. And I mentioned this before about organic chemistry. This is what's so amazing that just a few atoms can be put together in so many different ways. The petroleum companies love these and they are trying to catalog every known isomer of all the molecules you can find in petroleum. So I was just talking to my colleague and they paid him vast his laboratory, vast sums of money for a few milligrams of obscure hydrocarbons. Dodecane has 355. I won't ask you to try to write all of those out. And icosane has a whopping 336,319 isomers. Definitely not something to end up writing out. So we've already used the isomers of pentane as a platform to talk about van der Waals interactions. And I just want to bring this out again now that I've laid them all in the open. Pentane, I said, has a boiling point of 36 degrees. All of the other isomers, both of the other isomers, have the exact same amount of stuff in them and yet they're more compact. And as a result, you get fewer van der Waals interactions. Isopentane has a boiling point of 30 degrees. Neopentane, a boiling point of 9 degrees. So this is just an illustration of the concept that we had before. All right, I want to take a last moment to talk about describing the various carbons and hydrogen atoms. And let me take as an example isopentane, two-methylbutane as an example so that we can start to see what chemists refer to for the types of groups and hydrogens and carbons in the molecule. So here's our isopentane. I'm going to write it out explicitly. And so the terms that you will hear for the CH3 group we've used before, a methyl group. The CH2 group we refer to as a methylene group. And the CH group we refer to as a methine group. These types of names are not just nomenclature. They also give sense and structure to the molecules and lend sense to the reactivity of the molecules. There's a related way of naming things and something that you should be aware of. And so I'll take our isobutane again as an example or isopentane again as an example. And we talk about the types of carbons and hydrogens in the molecule. We describe a carbon with one other carbon as a primary carbon. You'll often see this as one naught, one degree carbon. And the hydrogen that's attached to it described as a primary hydrogen. This type of distinction is important because primary hydrogens and secondary hydrogens and tertiary hydrogens have different reactivity. Carbon with two carbons attached is a secondary carbon. So again we'll use two naught as the abbreviation. Carbon and in turn the hydrogen is a secondary hydrogen. And in this molecule the methine group, the CH group, we refer to the carbon as a tertiary carbon. So I'll use three naught and the hydrogen as a tertiary hydrogen. Now not exemplified in this molecule but exemplified in neopentane is one last type of carbon for which of course you won't have a hydrogen. And that's a carbon with four carbons attached to it. And we refer to it as a quaternary carbon. All right. Well that is what I would like to say about alkanes for today. Tomorrow we're going to our Wednesday. We're going to pick up with some systematic nomenclature and then we'll move on to some other aspects of alkanes.
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -1:58 General Formula of Alkanes -8:17 Properties of Certain Alkanes -15:09 Naming Alkanes Past Hexane -19:19 Isomers -23:28 Isomers of Butane, Pentane and Alkanes -31:49 Isopentane Example
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10.5446/19386 (DOI)
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Good morning! So today we're going to start by talking about the government's nature about games, that is how one needs our games. And we're only going to spend a little bit of time on it. It's easy to get the way thought out of this, but there are a lot of rules. And honestly at some point you'd say, computer can do this better. And in fact, computer can. What I want you to do is look at the basics, and particularly to understand the anatomy of the molecules that we're working in. Because just as in our identification of functionaries, seeing these structures not as a collection of zigzag lines on the blackboard, but rather as meaningful molecular structures, really is what identifies your thinking as an organic chemist. And then, hopefully in today's lecture and certainly on Friday and into Monday, we're going to be playing with our molecular model. And have fun! This is Kim's toys, except there's some science behind them. They actually made some sense. I'm going to figure out the rules. Take your toys. This is Legos, and this is what fascinates a lot of organic chemists, because just about anything that you can put together with your molecular model set that obeys the rules of structure and bonding is something that an organic chemist can synthesize in the laboratory, starting with simple chemicals. Most of them are ultimately derived from petroleum, from alkanes, and are used in aromatic compounds. And as for the ones that don't obey the rules of structure and bonding, being chemists, we are naturally fascinated by the idea of things that break the rules. So the idea of molecules that break the rules, or at least bend the rules, also continues to fascinate. So if you make a molecule that seems too strained to possibly exist, like the molecule tetrabegrate, you can look it up if you want, or 1, 1, 1, propellate, you can look it up again if you want. These are molecules that will bend and break your molecular model set. These are molecules that have also fascinated organic chemists and they both fall into the category of psychoalategies, which we'll be talking about. All right, so some basics on the nomenclature of alkanes. The general gist is to name the longest chain and identify the substituents. And this really isn't an exercise in naming. It's an exercise in thinking about what the structure of the molecule is and figuring out what's what. So let me draw out a structure and show you the conundrums that come off. So if I look at this molecule, the first thing I might be inclined to say is, oh, I see 1, 2, 3, 4, 5, 6. The 6th carbon chain is a hexing. But realize, of course, that's not the longest chain. Here's the longest chain. 1, 2, 3, 4, 5, 6, 7. So in seeing that bit of anatomy, you're realizing, okay, this is a heptane, non-hexane. And then in turn, if you're looking at the substituents, the groups that are attached to the chain, and we're going to use these same ideas when we name alcohols, when we name amines, and when we name alkyl halides, we're going to look and say, oh, if we're counting this chain that I just identified, and we're going to name this 7-aluminum chain as the longest chain, then our substituent is a methyl group. In other words, here on the 7-carbon chain, we have a methyl group. And we get a methyl group because methane, the 1-carbon alkane, becomes a methyl group. What we want to make sure is we don't get ourselves confused and say, oh, this is the longest chain, here are the 6-carbon chains, and we have an ethyl group. And remember, of course, ethyl group comes from ethane, goes to an ethyl group. All right, the next thing is to number the longest chain to give the lowest number to the first substituent. So capitalized is this. We already decided in this example that we have a 7-carbon chain, a heptane chain. And so now the only issue that remains is to identify where the methyl group resides on the chain. I could number from the right and I'd come up 1, 2, 3, 4, 5, 6, 7. Now we put the methyl at the 5 position. But I'm wrong doing that. I'm correct numbering from the left because that's going to put the methyl group at the lower position. 1, 2, 3, 4, 5, 6, 7. So you're always going to number your chain to put the first substituent at the lowest position. So this compound, and its IUPAC name, then becomes 3-methyl heptane. And you notice that it's all one word. And so we're not 2-ethyl hexane. And we're not numbering in the wrong direction so we're not 5-methyl heptane. All right. The next rule of nomenclature is when you have multiple substituents, you're going to alphabetize. That is to alphabetize the substituents in coming up with the name. Let's take the following example. And I've designed all of these examples to teach us something. That's an ethyl group up here. Okay. So the alkane, what's our alkane? How long is the longest chain in the molecule? Nine. And what do we call? No name. So this is a derivative of no name. And now we're going to number from the end that puts the first substituent at the lowest position. In other words, we don't number from the left on this because that would start us off at 5. We number from the right that starts us off at 4. And so we have a methyl group at the 4 position and ethyl group at the 5 position. And now here's what I mean by alphabetized. We're going to call this compound 5 ethyl, 4 ethyl, no name. In other words, once we've worked out the substituents and the numbering, then we're just going to put them in alphabetical order. And notice how I use dashes, 5 dash ethyl, dash 4 dash methyl, no name in naming the molecule. So again, just by counter example, I'll say not 4 methyl, 5 ethyl, no name. And this is usually the level of arcane stuff where I don't know, maybe the stupid people who make up the N-pad exams or something want to trick you up. And where it becomes a little arcane. Here's one more arcane rule. First, the simple rule, use di, tri, tetra, etc. for numbering, for counting the numbering of substituents. That makes sense. But the crazy thing which I'll show you in just a second, let me give you one example. All right. Log is chain. Fine. No matter how you count, whether from here to here or here to here or here to here, you come up with a 5 carbon chain. And it probably makes sense, even though we have one methyl group at this position, it probably is kind of, and one at this position, we have a second at this position. So it's probably kind of intuitive that we're going to number in this way. So this compound gets number 2, 2, 4, trimethyl pentane, so far so good. You notice that we use commas between the numbers when you have multiple substituents in one position. And we use a hyphen to set them up. So far so good. Here's the additional arcane piece of knowledge that probably makes some people very happy. You alphabetize this if one also had, I don't know what you'd have, doesn't go beyond t in there. You also would go beyond m. Well, all right, a propyl group. If you have a propyl group, the crazy thing is you alphabetize this as m. So in other words, you alphabetize trimethyl as m. I'm sure if you wanted to play a game, you could come up with a molecule where the name would be wrong if you alphabetized this t and write it out as m. Again, that gets to be a little bit arcane. All right, your book will probably go further into things and honestly, in getting yourself familiar with this, start with your textbook open because you'll have a few questions on nomenclature. Start with your textbook open to the pages on nomenclature and just flip through and after a couple of exercises, most of it will sit in your mind. All right, certain substituents, and this actually is important, certain substituents have names that you should know. Just as knowing the anatomy of anything gives you a sense of it, knowing some of the names of substituents gives you a sense of what's going on with the molecule. And just as in talking about my car, I have the engine and the accelerator and the brakes and the headlights, there are certain substituents that really roll off the chemists, the tongue of organic chemists. So for example, this substituent is an isopropyl group. If you have this substituent hanging off of the middle of your noname group, you would call it 5-isopropyl noname. And you've seen isopropyl before under isopropyl alcohol, one of the common names of 2-propylol. All right, another one somewhat less widely used but still used in nomenclature. This group hanging off is an isopropyl group, and we saw isopropyl the other day. Three more that are worth knowing. CH3, CH2, CH3 with a substituent hanging off the CH group. This is a sec-butyl group. Sec stands for secondary. You'll sometimes see this written out either as S-butyl or as secondary-butyl. Most often you'll hear it referred to simply as a sec-butyl group. Another one widely used, we're going to be talking about it in reference to various cyclo-nexine derivatives. Is this group here? This is a tertiary-butyl group. T stands for tert, stands for tertiary. Often you'll see this written as a T-hyphen-butyl group. Probably more often than you'd see secondary-butyl written out as S-butyl. Last one, question. No, this is not a complete polypule. This is just the fragment. The question is, does the CH have a 2-next to it? We have one more valence on the carbon. The carbon has a hydrogen, a methyl, another methyl, and one more substituent. One more group. Little more stericisophia for neopentane. If you connect something to a neopentane, you have a neopental group. Remember, NEO means new, so this neopentane is new-entane. Why does isobutyl have an H2? Thank you. Oh, sharp eyes. Thank you very much. Other questions or corrections always appreciated. Alright. Let's talk a little bit. So that's really all I want to say about alkanes for the nomenclature. Let's talk about cycloalkanes. We already said that cycloalkanes are alkanes where they're saturated hydrocarbons, where you have a ring in the molecule, where instead of having two hydrogens, the molecules are connected together to form a ring. So the smallest cycloalkane consists of three CH2 groups connected together in a ring. I'll write this out explicitly since the first time you see this, it looks very strange, and I might add very strange, and it is very strange. And we'll talk more about strange in a little bit. This molecule being a three-carbon ring is cyclopropane. Remember we said the cyclonalkanes with one ring in them have a formula CnH2n, so the molecular formula here is C3H6. Alright. Well, it shouldn't surprise you that the four-carbon cycloalkane C4H8 is cyclobutane, or that the five-carbon cycloalkane is cyclointane, C5H10, or that the six-carbon cycloalkane is cyclohexane. We'll be spending a lot of time talking about cyclohexane because it has a really interesting thing to it. And for the most part, the nomenclature of cycloalkanes is what you'd expect. It's pretty intuitive. For example, I take two methyl groups and put them on the same carbon on cyclopropane. All of the ideas that we had before make a lot of sense when naming alkanes. We're going to call it a dinethylcyclochropane because there are two methyls on it. Because the methyls could be either on the same carbon or they could be on different carbons, we need to specify what dinethylcyclochropane it is. One of the interesting rules of nomenclature is if there's no other choice, then you often can omit the number. Here we have another choice. I'll show you a case where we don't in just a second. So this molecule is 1,1-dimethyl. And I'm going to put a hyphen near only because I'm breaking lines. If you're writing this on one line in your notebook, you wouldn't put a hyphen, cyclochropane. Now let's try one more example. Here I'm going to take the cyclohexane ring. What's our substituent there? It's a tert-butylcyclohexane. So here's the thing. So this molecule is tert-butylcyclohexane. Do we have to specify the position of the tert-butyl ring on that ring? No. No matter where I put it, it's the same whether I put it here, here, here. So I don't need to call it one tert-butylcyclohexane. There's no other choice. If I had a methyl on the ring and a tert-butyl, then we'd have all of that good stuff of figuring out which one is the lower numbers, specifying the numbers, etc., etc. So this molecule is simply tert-butylcyclohexane. And for those of you who are typing on your computers, if you really want to be fancy about it, you can put the tert in italic font. Your textbook probably does. Would I specify, why did I specify the number here? Is that the question? Ah, because there are two different cyclohexanes, cyclochropanes with two methyl groups on it. This molecule is one-two dimethyl. I've been cyclochropanating. And in fact, you'll later learn that there's some even additional subtleties at that point. So we're just specifying it because we have to know whether it's one-one or one-two. You're later going to learn when we start to talk about stereoisomers that there's cis-one-two dimethylcyclochropane and trans-one-two dimethylcyclochropane, two diastereomers, and on the trans-one-two dimethylcyclochropane, we can further specify whether we have a mixture of enantiomers, right-handed and left-handed molecules, versus just one enantiomer in which we would call it either RR-one-two dimethylcyclochropane or SS-one-two dimethylcyclochropane. But like so many good things, we're going to peel back the layers slowly and help things sink in and to help you really appreciate the anatomy of these compounds. And by the time we're getting to stereochemistry, we're going to be thinking a lot more about three-dimensional structure than how you name it. For example, why the cis-isomer of one-two dimethylcyclochropane doesn't have two enantiomers, two-handed forms, and the trans-isomer does. I'm looking at these. How do you call these numbers when you name your compound? How do you determine the numbers when you name your compound? You first identify the longest chain in the molecule, or it's a ring. You identify the type of ring it is. So we figure out, okay, we have a nomane chain, or we have a cyclohexane ring in the molecule. Then you look at the numbering and you number from the case of a chain the end that puts the first substituent at the longest number. So in other words, if I have a methyl group, three from, if I have a nomane and a methyl group here and an ethyl group here, I'd say, well, I'm going to number from this end because that's going to put my first substituent at the longest position. Then there are a few more chain rules. For example, if you have a chain and a ring in the molecule, if the ring is bigger, you name it as the ring. If the chain is bigger, you name it as the chain. And then that gets to be a little bit of a chain. I saw a candle up over here. In the nomane? I think in that case, and that's getting great question. So the question, and this is called stuff the problem question. So the question, oh, well actually you picked the one that's easy just by the nature of it because here the chain becomes decay. But your question was if we had, let's say at the three position just to make things fun here. If we had this molecule, your question would be only numbering from this end or numbering from this end. I think your numbering from this end, honestly, it gets to a point of arcaneness that very few people care about. Fortunately, as I said, computers are great at rules. And at that level, we're not talking thinking and anatomy here. We're talking arcane rules. At that level, computers are very good at following rules. Fortunately, your text book there will give you rules, ad nauseam, so that you could actually figure it out yourself. But we're going to now move on to thinking and visualizing in three dimensions because that's a lot more fun and a lot more interesting once you understand what all these thingies and zaggies at least are on the blackboard. Besides, it gets us to play with toys sooner. Alright. So what I'd like to do now is to talk about confirmations of alkane. And today and on Friday, we're going to talk about ethane, butane, and cyclohexane. And the reason we're picking these three is they all bring out different concepts. So it's not just ethane that the ideas we're going to talk about apply to which all of the alkane, all of the alkyl with carbon and hydrogen. It's not just butane. It's interaction in many long chain alkanes and ring compounds. And it's not just cyclohexane. It's many compounds containing six-membered rings which are quite plentiful, as I mentioned before, in steroids and other compounds. So anyway, we're going to start with these archetypes and let us begin by talking about the confirmations of ethane. And I want to introduce an idea here, a way of looking at molecules called projection, more specifically, human projection. The big problem I have with the blackboard you have with your piece of paper is that we're trying to represent three-dimensional structures in two dimensions. And so we're going to learn some tools to represent them and to help us get these pictures in our head. And that's going to carry a lot of information with it. We'll use molecular models as an aid to help us get these pictures into our head. So this drawing here is a representation of ethane in what I call a staggered conformation, what is called a staggered conformation. If you have your plastic molecular models at this point, get them out. One thing that you should be able to do, let's see if I can get our video going here. What I'm going to do is try to send some, assuming the video works, is to try to send some images up to the top. Now what I urge you to do is exactly what I do. You don't need all of your models by all means, but get yourself a bag. It can be your backpack. It can be the bookstore bag. Put a few of them together and keep them. You're set well with the exception of one exercise in discussion this week, be twice as much as you need, which means you can also share them with your friends. If you haven't already done this and you haven't watched the David Austin video, you take two of these pieces and you put them together. And you don't just sort of put them together so they stick. They're going to snap once and they're going to snap a second time until they're in good and deep. I may send now if people are having trouble next week, I'll ask the TAs to give some feedback, but if fucking Johnny sees people are having trouble, I'll send a picture of how to do it right. Get your pieces together. There should be sort of a double snap until they're in deep. Thank you. Got it there? Little more. Once you grab one arm, you grab the other. You don't grab both, you'll be fighting and you go the second play. All right. And do that. There's no great treasure in taking them apart and putting them in a silly box. Just take your boxes and set it aside and have some sort of a back and have some. So get a couple together and then we're going to connect them together to make the ethe molecule. And what we're going to concern ourselves with right now is the rotation about the center of the carbon-carbon bond and specifically the relationship of the CH groups to each other. What I'm going to show here in projection is our staggered conformation of the molecule. By staggered, I mean that the HHs are not overlapping with each other. And I'm going to contrast this with an eclipz conformation. We call it eclipz because the hydrogens block each other. I'm going to just rotate about one of the bonds here to make my molecule, my model, into an eclipz conformation. So we've rotated about this bond. Now the problem with this type of representation, this representation that I've drawn in the blackboard is just great. It's also a little bit hard to really see the gut specific anatomy of the eclipz conformation. So let me go back to the staggered conformation and we're going to start with our staggered conformation. And what I want to do is to simply rotate it like this. And I think what I'm going to do just to help you see it is I'll prop it up a little bit on a piece of chalk here. Maybe not. Okay. So when you're staring down the barrel of an ethane molecule like we are doing now, you can make a drawing of this that shows this particular representation. I'm not going to be a, ah, you're a sinner. There we go. Almost good enough. Just about good enough. Alright. So staring down the barrel, looking at the rear end of an ethane, we can draw our carbon on front like so. We're in a staggered conformation. If we look straight down it, I'll tilt it so we're looking straight down. If we look straight down, you don't see the back carbon. The back carbon is right behind the front carbon. But what you do see are the hydrogens coming off the back carbon. And we call this drawing a numid projection, N-E-W-M-A-N. It's nice. When you invent your way of thinking or you invent a new, like a new type of chemical reaction, you can get it named after you. In other words, you can live on forever in the minds of hundreds of thousands, maybe millions of people, who've studied chemistry or organic chemistry. That's quite a legacy to be able to lead. And that's really what the development of thought and the discovery of scientific information is all about. It's being able to convey knowledge and convey ideas. And yes, often there's a little bit of ego in it. It is being able to get a little bit of credit for it. So a numid projection allows us to see the relationship between the hydrogens, between the front carbon and the back carbon. We can also see that we have an angle created between two planes. We don't call the di-egrel angle, but you don't have to think about complex geometry. Just realize that we have an angle created between this line and this line. We'll call this theta this di-egrel angle. We'll call this di-egrel angle theta. And in this case, theta is equal to 60 degrees. I'll write the word di-egrel angle over here. Now I'm going to go from our staggered conformation to our Eclipse conformation. Here we are looking down the back end of our cyclohexane of our ethane rudder. And I'm simply going to rotate until we get to the Eclipse conformation. And again, the camera doesn't exactly line up with things, but pretty close. That actually provides up there, provides a very nice way of dealing with what we have to draw. We have to represent two overlapping CH bonds. And so the way we're going to do this is we'll do our numid projection just like we did before. There's our carbon on front. The carbon on back, obviously if I drew the CH's right on top of each other, we'd be in trouble. I wouldn't be able to see them. Literally they would be right behind. So we'll just offset them a smidge. We'll just provide a sense of perspective just like my projection up there isn't quite perfect. And you can see that the hydrogen's still quite overlap. So this is what we would do for our Eclipse conformation of the molecule. So we talked before about molecular structure. We talked about bond length, bond angle. And this brings us into one of the things that organic chemists really concern themselves with. This last level of structure, conformation, the geometry of molecules in three-dimension involving rotation about rotatable bonds. So this is not a case like ethylene where the molecule really has no choice but to be flat. When you take your double bond pieces in your modeling kit, you have no choice but to make a flat ethylene for a flat carbon yield group. But now we have some choice and we actually have to apply some intelligent thought about the structure of the molecule. Now we're going to give us an energy diagram. We'll be talking more about energy diagrams on Friday, but we're going to plot an energy diagram of what happens as you bury the dihedral angle as you rotate from Eclipse to staggered back to Eclipse to staggered to Eclipse to staggered back to Eclipse. So we're going to do a full 360 degree rotation about the dihedral angle. And I have to confess I'm not much of an artist and I usually need some guidelines for help. What's good is my struggling at the blackboard to produce a neat, legible diagram also gives you a long time to get the thought right. And what I've seen with students on exams is often they'll just sort of make a squiggly line basically, oh I don't understand this, so I'm going to do this slow, hopefully that'll be a good chance for both of us to have the chance to really think about it. Alright, so as I said we're going to rotate about our dihedral angle, we're going to start at zero degrees, we're going to go 60, 120, 180, 240, 300, and 360 degrees about our dihedral angle. The eclipse conformation is high in energy, it's unstable for reasons that I'll tell you in one second. It is 3 kilocalories per mole higher in energy than the staggered conformation. I'm going to make myself a little guideline here to help me out because we're going to go eclipse staggered or eclipse staggered or eclipse staggered. Alright, so I'm going to make a guideline to help me out at 3. As I said at 60 we're lower in energy by 3 kilocalories per mole. At this scale the absolute numbers are arbitrary because we're only talking relative energy, so zero means we're lower by 3 kilocalories per mole than eclipsed. If I go back to 120 I continue my rotation, we're back to eclipsed, to 180 we're staggered, to 40 eclipsed, 300 staggered, 360 eclipsed. I'm going to make myself some guidelines for the energy profile as we rotate about the bond. We get a sinusoidal curve going from high energy at zero to low energy at 60, to high energy at 120, to low energy at zero at 180, to high energy at 240, to low energy at 300, to high energy at 360. Last couple of things I want to say, we're going to come back to many ideas here. One idea that I want to mention is that this means that eclipsing costs us per bond, costs us 3 kil, costs us 1 kilocalorie per mole. And there are 3 HH eclipsings. The reason that eclipsing is high in energy is interesting. In the eclipsed conformation, remember orbitals, we've gone away from orbitals for a while. Here are the orbitals, the sp3 orbitals and the 1s orbitals that make up the molecule. We have, and I've just drawn one of them, in our CH bond we have a filled orbital overlapping with a filled orbital. That's bad. Just as it's bad to try to bring two helium atoms together when they're filled 1s orbitals, it's bad to try to overlap two filled orbitals associated with the bonds of the CH bonds, and so we pay an energetic price. Now, bad doesn't mean it doesn't occur. And that molecule ethane rotates over 10 billion times a second at room temperature around the C bond. We go over an energy barrier again and again, but that molecule is full of energy, vibrational energy, rotational energy at room temperature, but it prefers to be in the well. So we're going to pick up on this idea next time when we talk about new things.
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -3:00 Basics of Alkane Nomenclature -3:48 3-methylheptane Example -8:47 Alphabetization in Naming -15:15 Certain Substituent Names -21:18 Cycloalkanes -32:58 Conformation of Alkanes -36:00 Molecular Models -40:34 Newman Projections -47:16 Energy Diagram
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10.5446/19389 (DOI)
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Good morning. So today we're going to begin our discussion of chapter 5, stereochemistry, the three-dimensional structure of molecules. And remember I said in terms of the real biggies of pervasive concepts in organic chemistry, stereochemistry is one of the defining ones. And it's also one of the fun ones and one that really sets us apart from general chemistry in terms of how we think about molecular structure. Because stereochemistry is spatial, it's not palpational, it's looking, it's thinking, it's understanding different patterns and relationships. We'll learn a few terms along the way like adiandium, diastereomer, mesocomps. These terms themselves are not definitions, they're synopses of concepts, and it really is the concepts, not the words, that is the big part of what we're going to be learning. Let me start out by drawing two molecules, two stereoisomers, and then we're going to talk about them in relationship with each other and some other structures, and then we'll move on to get some others. So the molecules that I'm going to draw are cypheropropanes. And at two different positions, we'll call them the one and two positions on the rings, and we're going to attach methyl groups. One molecule of methyl groups will both point up and we'll have hydrogens pointing down. I'm trying to represent pointing up by wedges and pointing down by dashes. For the other molecule, I'll have one of them pointing up, one methyl group pointing up, and the other methyl group pointing down putting hydrogens. Sometimes you'll see hydrogens drawn in explicitly, sometimes you'll not see them drawn in explicitly, depends on part of what one's trying to show. Obviously these two molecules are different, you can see that they're different. I'm going to project out physical models. Who brought your cypheropropanes today? Who has a cypheropropane? Alright, so let's stick a couple of methyl groups onto them and let's see if I can get a video up here. See, I think I've concluded that the best background for these molecules is actually, I'm sure, rather than trying to use the table. And so you can see our cypheropropane, you can see the methyl groups are in different orientations, and you can also see this isn't just a conformational issue. When we did our gauche butane, or when we did one for the armchair cyclohexane, you could wiggle, you could split your molecule, and it would interconvert. Those are conformers, conformational isomers. They're in general not compounds that you can isolate, separate, and put into the bottles. But in this case, in the case of the cis isomer, the one I'm holding in my right hand, that you're left, and the trans isomer, these are two separate compounds. They're compounds that you can put into a bottle. I'll write out the names of them, we can talk about what types of stereoisomers they are. So the molecule on the left is cis-1,2-dimethylcyclo-procane. The molecule on the right is trans-1,2-dimethylcyclo-procane. So I'll write this cis for the left one, and trans-1,2-dimethylcyclo-procane. And you know I'm just going to write that, dimethylcyclo-procane, all in one word. These two molecules are stereoisomers, and I'm going to spend a little time writing out definitions. As I said, definitions really in their own don't carry much weight. It's the concepts behind them. This isn't a dictionary game, this isn't something where you just learn some words. The words are much more related to those structures and to these structures. So stereoisomers are isomers with the same connectivity, but a different arrangement of atoms in space. And by that I mean in both of the molecules you have a three-membered ring, in both of the molecules you have a methyl group on one carbon of the three-membered ring, and a methyl group on the other carbon. And yet in one case the methyl groups both point on the same side of the ring, and in the other case they point on opposite sides of the ring. So same connectivity, but a different 3D arrangement in space. I'm going to contrast that with the following molecules. Let's take our 1, 2, let's take our cis 1, 2-dimethylcyclo-procane, and I'll write it without the hydrogens this time. I could also write it like this. All of these are representations of the same thing. I'm going to contrast it with the following molecule, a contrastive encyclopentane. And you notice these two molecules both have the same molecular formula. They're both C5H10. But obviously, obviously, obviously they have a very different connectivity. We would call these two molecules the cis, the dimethylcyclo-procane, and the cyclopentane, constitutional isomers. In other words, they have the same formula. This is, of course, the definition of an isomer-equal molecule, iso-equal or molecule. But they have very different connectivity. So what I want to do now is to classify our stereoisomers into two types, enantiomers and diastereomers, and to develop some of the concepts and some of the spatial relationships associated with these. So we're going to come back to our cycle of protonates in a minute, but let me give you enantiomers. Enantiomers are stereoisomers that are non-superimposable near images. And this definition that I've written is really a litmus test. If you're unsure, ask yourself, are the two structures weirder than images, whether two molecules are in a cure, and can they be placed on top of each other if we rotate and manipulate and so forth? Oftentimes in my thought processes, and yours very soon, I hope, you'll see a series of patterns, and you won't even need to go to any reference into any sort of physical comparison on your images. You'll say, oh yeah, he inverted this asymmetric center. Of course they're enantiomers. So I'll give you several different equivalent ways of looking at molecules. Let's start with the following. So I'm going to start with two bucnolls. And you'll notice I'm sneaking in names as we go along. When you get to alcohols, you'll learn formally about the nomenclature, but this just means it's a butane chain with an alcohol and hydroxy group at the tube position. And you can write the molecule like this. All I'm doing here is saying we have an OH group and an ethyl group and a methyl group and a hydrogen on this carbon. I haven't explicitly shown the 3D structure, but obviously, obviously in making it, it's there. In other words, that representation is just showing the connectivity. I'm going to give a different representation that shows 3D structure. We're still the same molecule, but now I'm specifying which way the OH group and the hydrogen group are attached at this carbon. And it's the same whether I write it like this or whether I don't show the hydrogen and just leave it implied. Those are both the same. But I'm going to contrast them with the following. If I throw the OH group back behind the plane of the blackboard and have the hydrogen coming out instead of this one on your left, where I have the OH group pointing out, the hydrogen coming back. And again, I can represent them either way. So now I've explicitly shown the stereochemistry of the two butanol. And you can see we have two stereoisomers, and I'm sure right now you understand that these two are enantiomers. Let me show you what I mean by mirror images. What I've done with the molecules, I simply have preassembled the molecule on your right and the molecule on your left. And I'm going to go over to the camera now, and I'll just show you my feeble attempts to superimpose them upon each other. So let's see if I can get far enough back. Now it's a little hard to see. I'm looking at myself right now. You're looking at me too. It's a little hard, you don't get that much shading, but I think you can see the molecule on your right has the OH group coming back toward me. You can see me rotating in the red atom, red is oxygen. The molecule on your left has it coming out. And now I'm going to try to superimpose them, and I can get the oxygens and the hydrogens to go on top of each other. But then I have ethyl group on top of methyl group, or I can flip it around and I can get the ethyl groups and the methyl groups on top of each other. But now in one case I have the oxygen going back and the oxygen coming forward. These two molecules are non-superimposable and they're mirror images of each other. What do I mean by mirror images? I mean that if I pretended I had a mirror between them, I would reflect the molecule on one side into the molecule on the other. You know how everything's backwards in a mirror? That's why it's hard for me to be up here, because I'm looking at the opposite side of the molecule, so I'm constantly having to say my right or your right when I'm talking about my left. In case you're having trouble here, I also have made it certainly easier to visualize on the screen when you have some nice computer models here. So I've made the two molecules as computer models. Who ended up downloading and playing with the software a little bit? Fun? Yeah, it is kind of fun. So I just made this for myself to project here, but it's sort of nice. I realize a lot of the things that I like to play around with are also fun for you. I've linked my web pages to it. So what I'm going to do is here on the molecule on the left, I'm going to just, this is just to make it nice and pretty. I'll make it maximum quality. I'll go to show and I'll show sticks. And then on the other one, I'm going to do the same thing. So I'll go to display. If I were doing it for myself, I wouldn't bother to go to the trouble of making it better quality, but I want it to be nice for you. All right, so here you can see that no matter how I rotate the molecules, you can see that they're mirror images of each other. And you can probably see that no matter how I rotate them, there's been no way to put one on top of the other. All right, so I'm going to use the video here and let's get back to some definitions. All right, the molecule 2-butanol is chiral. Whether I draw it that way, showing specifically the tetrahedral asymmetric center, or I draw it without showing it explicitly, it's still there built into the connectivity of the molecule. That molecule is handed just like my left hand and my right hand are handed. Just like my left hand and my right hand can't be superimposed on each other. They're complementary, they're mirror images. But of course, if I had two left hands, I'd literally place one hand on the back of the other. Instead, I have to place the back to front, they're not the same. We say that 2-butanol is chiral, it's not superimposable on its mirror image. That's another way of saying it. And we call carbon 2, that's the carbon with the OH attached to it. It's the one that gives it 2-butanol in its name. It's technically called a tetrahedral asymmetric center. Want to ask some asymmetric, please? Often people will call it a chiral center. Not really wrong, but it is technically tetrahedral asymmetric center. It's a little bit better. It's a tetrahedral atom with four different substituents. As I said, sometimes it's called a chiral center or an asymmetric center. Now, I want to contrast our two-butanol with another molecule, another alcohol, and we'll actually go to a smaller alcohol, isopropanol or 2-profanol. And I'm just going to write it the exact same way I did on the other blackboard. I'll start out writing it, not pointing out that the carbon is tetrahedral. And then just as I and the other blackboard explicitly wrote it, the OH and hydrogen, I'll do so over here. And I'm going to write it just the way I wrote it on the left-hand side there, just the way I wrote it on the right-hand side. What do we say about these two drawings? They are indeed mirror images, but they're not enantiomers. They are exactly. They are superimposable mirror images, not non-superimposable. In other words, they are the self-same thing. They're just two different drawings of the exact same molecule. I'll just write it the same, not different just to be really explicit. So we would say 2-profanol is a chiral. It's not chiral. If you want to be technical, you could say because I applied the Littlist test, because I checked and found it was superimposable on its mirror image, if I just took the structure on the left, won't even project it, and spun it around, I have the structure on the right. You could also look at the scent at the molecule and say, oh, of course it's a chiral. It has no tetrahedral asymmetric center in it. And that's probably what I would do rather than any sort of mathematical, or any sort of spatial manipulations. So let's come to a couple of definitions and I'll write them out explicitly for you. Stuff that I'm actually talking about. So I'm going to give you a slight generalization here. We can say that a molecule with a tetrahedral asymmetric center is generally chiral. And the generally is largely a qualification on putting in for myself because I can come up with some very, very, very specialized circumstances in which there was a rapid inversion of the center. But if you want to omit that word generally, you can do so from your notes. And a molecule with a plane of symmetry is a chiral. And here's our cyclone. Here's our two-propanol again. And I'll just point out the plane of symmetry is right down the center. In other words, I can reflect the right half of the molecule into the left half through my piece of paper here. There's a plane of symmetry in the molecule. And the more you see of these examples, the easier it is to really get the hang of them. Let's try a couple of more examples. Let's try two mutinons. Chiral or a chiral? A chiral, right. Why is it a chiral? Where's the plane of symmetry? So in other words, if I reflect the front of the molecule goes into the back, you can put it another way, the whole skeleton lies in a plane. And hence you have a plane of symmetry in the skeleton, the hydrogens are pointing out. Another way to look at it, equally accurate, is to say there's no tetrahedral asymmetric center. And there are only some very special cases called atrobisomers where you have molecules blocked through rotation into mirror images that actually can be separated. I mentioned early on when I talked about two butane, I said the gauche conformer at 60 degrees is actually the mirror image of the gauche conformer at 300 degrees. Technically those are two non-superimposable mirror images, but they interconvert millions and millions of times, billions of times per second. So no one can say you can isolate a native universe, but there are very special molecules where they are aligned into a chirality without having any tetrahedral asymmetric atoms in there. Alright, let's take another one. I'm not going to write it out explicitly, but let's take fluorobethane. So I'm going to write a chiral here. What about CHFCl, carbon with a hydrogen, chlorine, and bromine? Chiro, why is it chiro? Every single atom is different size or more specifically different. So a carbon with four things attached to it, four different things attached to it, is a tetrahedral asymmetric center. In two butanol, which I've now erased on that tetrahedral asymmetric center, we have an oxygen and a wage group, we have a hydrogen, we have an ethyl group, and we have an ethyl group. In the case of bromocoronorobethane, we have the tax to one carbon, a bromine, a chlorine, a chlorine, and a hydrogen. And if you want to do the experiment, all you do is you draw the molecule. If you want to see it for yourself, you draw the molecule like so. You draw its mirror image. I'm putting a mirror plane right here. And then you check, is the molecule on the right superimposable on the molecule on the left, and you find very quickly that the answer is no. These are non-superimposable mirror images. In other words, chromochlorochloronorobethane is chiral. All right, we started by talking about stereoisomers. We said that stereoisomers was the generic, the broad term, the molecules that have the same connectivity, but a different arrangement of atoms in space. There are two types, two main types of stereoisomers. Anantiemers and the other is diastereomers. Diastereomers are stereoisomers that are not anantiemers. So, we're going to talk about the question. Priorities. So you're talking, the question pertains to conical pralogue notation, and it's about priorities. So we will come to how we name atoms. We assign priority to atoms. The lowest atomic number. So this is a system where we are going to very soon learn to identify our tetrahedral asymmetric centers as either being what's called R rectus right or S sinister left. And what we're going to find is that there are some rules. It's just a formalism for saying we'll call this substituent number one, substituent number two, substituent three, substituent four. And those priorities are based first and foremost on atomic number, and then they come to substituents on the atom and so forth. It actually is a formalism. It's just a way of naming it, just as if I decided, and everyone in the world, and you decided your name was Lisa. I don't know what your name is, but if they decided it was Lisa, you decided too. And for the work of the driver's license, you would be Lisa. So we define right and left in this way. We'll come to that. All right. So let's look at diastereomers. And those are what we had on the blackboard when I started and introduced the concept of stereoisomers. Here's our cis and trans 1, 2-diamethylcyclo-propane that I drew before. These molecules have the same connectivity. They're stereoisomers, but they're obviously non-super. They are not mirror images of each other. Hence, since they're not enantiomers, they're not non-superposable mirror images. They are diastereomers. I'll write this explicitly. I'll let me contrast this because we're doing this actually. I mean, after you've done this a while, for Buck and for Joni, this is easy because they've seen these structures on the blackboard and they're literally just spinning them in their mind doing these comparisons. But the first time you see it, it's like, oh, this is all new. This is all different. This is all kind of hard and confusing. Plus, we've got all these terms on top. So, okay. Let's try this versus this. Once the relationship of those two structures, somebody towards the back, I want to hear somebody yell out or see a hand go up. What's the relationship of the structure on the left and the structure on the right? I heard over. You flip it. Exactly. Beautiful. You flip it. You pick it up. You flip it over. And if you want to see it on the camera because I know why the back grow, it's kind of hard to see. Assuming I haven't lost my camera. Here we go. So, here they are pointing up. You rotate it. Oops. There you go. Here they are pointing up. You rotate it. They're pointing down. In other words, the technical term for this is just, these are the same. Let me throw one here and get my camera back. Alright. Let's try one more. We're doing little bits of mental gymnastics with our molecules. One of the reasons we're doing this is just like you go to the gym to exercise your body. Here you are literally exercising your mind, exercising your spatial thinking about molecules. So, let's go ahead and I'm going to write this molecule and I'm going to put the hydrogen up and the methyl down here and then the methyl up in the hydrogen. Look at those two structures. Now, you have a cyclopropane. Do like I'm doing right now. You have two, all the better. Take your cyclopropane, put on your methyl groups and actually make best if you have two, make both of them or when your neighbor makes one and your neighbor makes the other. Okay. Okay. Okay. Okay. Okay. Okay. Alright. So, here are my molecules and I have the molecule on, hopefully I've got it the way I've drawn it on the blackboard. I've got the cyclopropane on your left and the cyclopropane on the right and you can see that they're mirror images. In other words, there's a mirror plane right here between them. I've reflected this into this. But another way, I've inverted this tetrahedral asymmetric center, swapping the methyl group in the hydrogen and I've done the same over here. And so, I have my two molecules and now we're in the same conundrum as tubitinol. I can put the cyclopropanes on top of each other but the methyl groups point in opposite directions. I can put the methyl groups on top of each other but the cyclopropanes point in opposite directions. And that is the definition of enantiomers, non-superimposable mirror images. Alright. This is one of the reasons why I'm very much like the physical model. Because they really help us see these relationships. After a while, you can start to do this in your head. You can start to say, oh, I spin this structure around and then I have the analog with the methyl pointing down and the hydrogens pointing up. You can go and say with just paper, I spin it. But initially, having a touchable, tangible molecule is very, very valuable. Alright. I want to take one kind of extended example to finish things off here. I'm going to write out stereoisomers of two methyl one-cycloentenol. Alright. I'm going to make it easy, look easy to write out the, well, you're going to think it's hard to write out four different structures. I'm going to show you what I'm doing as I'm going along. So I'm writing four different structures, four cyclopentenols. I'm going to have the first one have the OH pointing out, the hydroxy group pointing out and a methyl group pointing out and a hydrogen going back and a hydrogen going back. On this one, don't bother to build the molecules. Just draw it along with me. And we'll call this one A because I'm about to make some comparisons among them. And then I'll do the same thing, a cyclopentenol. But I'm going to throw the OH group pointing back and the methyl group pointing back. And I'll have our hydrogens pointing forward. And we'll call this one B. I'm permuting, by the way, in case you're wondering what I'm doing here. I'm permuting the various structural drawings. The third one, I'll leave the OH pointing back and have the methyl group now permute that to go forward and have our hydrogen coming back. And we'll call that C. And the fourth one, I'll flip things around, have our OH coming out and our hydrogen going back at top. And then I'll have our hydrogen coming out and our methyl group going back on the bottom. We'll call this one D. Now, obviously A, B, C, and D are stereo isomers. They have the same connectivity. And yet, they can certainly seem in some cases, they're not the same. In some cases, you have the methyl groups and the methyl group in the OH on opposite sides of the ring. We call that transstereochemistry. And in other cases, we have that on the same side of the ring. We call that cisstereochemistry. Let's take a look at A and B. I'm going to do this with models. And I made up a web page for that. I think it's an easy one to do with computer models. And so I have these molecules on my page titled diastereomers. And I'll just make one. And I'll go click on the other. And they're in the same order as they are on the blackboard here. How are we doing on that position? And I will close our two butanol. And there we go. Get them both up. And I'm going to go ahead and make them nice. Display quality maximum quality. Show sticks to make them nice. And I will do the same over here. Display quality maximum quality. Show sticks to make them nice. All right. So if we look at these two structures and I manipulate them, I think we can see that A and B are mirror images. They're not superimposable on each other. I've reflected through this plane here. I've got one. I've got the other. In other words, A and B are enantiomers. And now we're going to do the same for C and D. Here's C. Here's D. Here's D. So sticks so you can see it well. Okay. Same thing. I'm just going to rotate them and try to compare them. And this is the same thing you can do with plastic models as well. So what's the relationship of C and of D? Enantiomers. They're non-superimposable mirror images here just for fun. I'll rock each of these structures so you can get a little bit better view of what we see. So C and D are enantiomers. So we're using enantiomer in a relational term. In other words, one is the enantiomer of the other. That's a way of saying mirror images. A is one enantiomer. B is another enantiomer. Now if we go to A and C, obviously they're not enantiomers. The methyl group and the OH are on the same side of the ring in A. They're on opposite sides of the ring in C. Stereoisomers that aren't enantiomers are diastereomers. And all of the other relationships for this set are the same. A and D are also diastereomers. A is a cis-stereoisomer. D is a trans-stereoisomer. And trans-stereoisomers are a type of diastereomer. D and C are also diastereomers. And again, D is a cis-stereoisomer. C is a trans-stereoisomer. They're not mirror images of each other yet. They're stereoisomers. So they're diastereomers. And finally, D and D are also diastereomers. Alright, well that finishes up this discussion. If you want to play on your own and you like these exercises, go ahead and try to look at the two events during the oisomers here on this page. And you can use the same thing even if you don't want the software. You can open this page for the password and the filter with your molastro box to play that inside.
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -1:35 1,2-Dimethylcyclopropanes -7:43 Constitutional Isomers -8:43 Enantiomers -10:14 2-Butanol -16:24 Chirality of 2-Butanol -19:21 2-Propanol -22:36 Generalization of Chirality -25:04 2-Butanol -30:03 Diastereomers -33:42 Two Isomers of 1,2-Dimethylcyclopropane -42:07 Stereoisomers of 2-methyl-1-cyclopentanol
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10.5446/19388 (DOI)
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Good morning. All right, that wasn't so bad, was it? Your functional groups were the biggies in romantic chemistry. Getting guys out to identify functional groups are some molecules that give them to meet properties, predictable properties. We're going to be learning more throughout the A, B, and C series about the properties of all different functional groups. Today I'd like to continue our discussion of the confirmations of cyclo-texane. We're going to focus on the main stable conformation, the shared conformation, and we're also going to talk a little bit about other confirmations, both in ham and chair and twist, both conformation, as we go through and get to understand this molecule. The light is to see everyone has cyclohexane. I see a boat, that's a beautiful boat, in the fourth row. So if you have a boat like this, you can pull off one end to make a chair. The chair stands like a three-legged stool with three axial hydrogens pointing down. It sits very nicely on your palm of your hand, if you have a big hand. You have three axial hydrogens pointing up. Last time when we started talking about cyclohexane, we learned how to draw it. We saw the projection of it, and we learned where the axial and equatorial hydrogen atoms work. So I just want to talk a little bit about a ring flip and what happens. I'm only going to focus on the hydrogen's attention to one carbon right now. Let's imagine we have HA and HB, and in my model of cyclohexane that I'm now projecting on top of my camera here, you'll see I put the red ball just representing any old atom in an axial position. We can think of it as a hydrogen atom here. We talked about the process of ring flip. This ring flip occurs millions of times per second, and in plain old, unsubstituted cyclohexane, we generate a second equivalent chair conformation when it undergoes ring flip. What's important about this is that the hydrogen that was equatorial, in fact all six of the hydrogens that were equatorial, now become axial, and the hydrogen that was axial becomes equatorial. So I'm going to do this with my model on the camera, and I urge you to follow along with me, and this really is the way you learn this, it's by touching these models, manipulating them, and visualizing them. So I've started, I've put a red ball to label one of the axial hydrogens, and a white ball to label one of the equatorial hydrogens, and I'm just going to grasp that carbon atom and pull down and rotate, and at the same time I'm going to pull up on the other side, and then I'll just touch up the conformation and make sure now my white atom and the other two hydrogens, we'll call these the 1, 3, and 5 positions, that they're standing up 1, 3, and 5, and then we have the others pointing up, and you'll notice our red ball now has gone from the axial position to the equatorial position. So the key on this is to be able to sort of grab both sides, it's a very simple movement, you just go down on one side, up on the other, and you just sort of wiggle it, and then you make sure that you have three hydrogens pointing up, and three hydrogens pointing down, and then you have a perfect chair conformation. So the trick is it's alternate hydrogen, so if your molecule looks like this, if you have four pointing down, if two in a row point down, you will have a both or a variant of a both conformation. Now let me show you what we go through in doing this. I'm going to sketch this out and show you the various conformations and how this process occurs. So let's imagine we start to pull down on this side here. So I've left the left side alone, and I've started to pull down on the right side, and halfway through we come to a point where five atoms are coplanar. I'll hold it up over here, and I'm going to put it up on the camera, although it's a little bit hard to see. Do you notice how at this point we have five atoms? One, two, three, four, five carbonations are coplanar. We call this a half chair. A half chair is a high energy point when we call a transition state. Remember, as we move over an energy surface, just like we've rotated about the bonds of ethane, or about the bonds of butane, you go through a series of peaks and valleys. The peaks we call transition states, they're high energy, unstable forms. The valleys we call conformers in the case of molecular conformation. So we're moving over a high energy peak, a half chair. We continue along. There's actually a few little bumps in the road. I'm going to give you the simple version, and then I'll show you something a little bit more complicated. When we come along and continue to move down, we get to a boat. It's called a boat because it looks like a rowboat. It looks like a rowboat that sits on top of the water. The boat conformer has a lot of eclipsing. We have hydrogens banging into it, into each other across. Still unstable. Actually, if you want to form something stable, you just give it a little bit of a twist and that eliminates some of the eclipsing interactions. It's called a twist boat. That's actually a stable but high energy conformer. A half chair is about 10 kilocalories per mole in energy above the chair conformer. The boat is about 7 kilocalories per mole higher in energy. This boat is about 5 kilocalories per mole higher in energy. You're at a boat and you're sort of halfway there because now what we've done is to pull down. I'll go up to our display here. I'm going to go back to a boat. We pull down the entire right-hand side of the molecule as it's appearing on the projector. It's my left-hand side, but you're right. Now we start on the left-hand side and we flatten out once again. We're going through a symmetrical process here. At that point where you're flat, where five atoms are co-plainter, you're at another half chair. Now all we continue to do is to pull up on the right-hand side of the left-hand side. It's always reversed from the left-hand side of the molecule. That's the whole ring flip process. We complete our ring flip by pulling up. If you want to do it quickly, you just do it at the same time, but if we want to sort of see it step by step, then you pull on one side and you pull on the other side. Questions or thoughts? It takes a little bit of practice and a little bit, okay, very good. What do you have there? You have both standing just about in four legs. In fact, it's just sort of a twist, but you notice the guy is one in four. They're heading into each other. What do you have there? Oh, and make it into a chair. Good for you. I'll show you a few other models up here. I have here a chair, and I'll put up, let's see, what do I have here? I built these the other day. I can put up, here's our half chair. There's our half chair. And you notice how we have five carbon atoms, so planar, with each other. So that's halfway through the process of conformational interconversion. Here's our twist boat. Confirmation. That's a twist boat. So, yeah, this is a boat, and the really bad thing about a boat is you have eclipsing interactions. Remember those eclipsing interactions and ethane that were really bad where the H's line up? So you've got hydrogens banging into each other at the one in four positions across the top of the boat, and you have this eclipsing interactions. If you just distorted a little bit, just twisted a little bit, now you have your twist boat. Yes? Upside down to the right side up doesn't matter. You have a boat there. Just grab the one in four positions, give it a little twist. Yep, not even so much. Back off, there you go, circuit twist. All right, well, our TAs are going to be taking us through some exercises this week with molecular models on cyclohexane, and we're going to get more experience on this in the discussion sections. But I'm absolutely delighted to see you playing with the molecular models, but this is how you start to learn and get to the other question. Ah, beautiful question. How come the half chair has more energy? How come the half chair is more energetic? Okay, the half chair is bad because, look at that, you see all those eclipsing interactions? Let me stop this for blocking. All right, so you notice as we new in project, you see an eclipsing interaction right here where my cursor is, and another eclipsing interaction, and another eclipsing interaction, every hydrogen-hydrogen eclipsing interaction overlapping the filled orbital created by the sp3 on the carbon and the hydrogen overlapping with another one on an adjacent carbon costs one kilocalorie per hole, and we have ten of those interactions in the half chair con for her. So there's roughly, well I guess it's eight, there's some other bad interactions, but we have roughly ten kilocalories per mole of strain associated in the line share. So we have a little flip between one chair and the other chair, which in this case are degenerate, which means they're the same, occurs a million times, millions of times per second. Molecules have lots of energy in them, they're constantly vibrating and rotating, and this occurs millions of times per second, and there's enough energy to go over that energy barrier, and that's the sum of the half chair and the both and the other half chair all the way to the other chair, millions of times per second. Those are energy barriers, those are the peaks. The two degenerate chairs here are equal in energy. What I'm going to do now is to put a substituent onto our molecule, and so we're going to make the two different chairs not the same, and we're going to make the funny wall in energy. So let's go now to methylcyclohexane, and I'll write out a skeletal structure. You can write it like that. If you want to be explicit about having the methyl group on there, you can write it like this, and what we're going to do is we're going to put the methyl group for starters in the equatorial position. We call this the equatorial conformer of methylcyclohexane. If you have a methyl group in your bag, in your book bag or whatever you brought for today, just go ahead, get back to your chair cyclohexane, put that methyl group in the equatorial position, get back to the three-legged stool, back to three hydrogens pointing down, three hydrogens pointing up, just like you have over there. Grab a methyl group, put it in the equatorial position, and I'll pop up a methyl equatorial methylcyclohexane to give you a little bit of guidance here. All right, so I have an equatorial conformer of methylcyclohexane spinning around up there. Do you like this one? If you want to play with it on your own computer, the software that I got actually gives me a license to share it with students. It's not easy software to use. I use it in my own research. It's pretty easy for viewing, but if people want it, I can email a link after people want it. All right, I can't really provide a lot of tech support on it because it's really complicated to use. The easy part is viewing. I've got some web pages set up with a lot of these structures. I've just set it up as a helper application for Firefox, which means every.pvd file opens automatically in it. So you'll get it. If you do that, you get the same performance I get. Anyway, it's fun software. You actually can even build models like this if you know what you're doing in there. And maybe what this can do, you still definitely want to be using the molecular models. We're going to have questions on them on the exam and discussion. But if this can complement your use of molecular models, and you like computers, you don't like computers or think it's finding hard, just forget about it because it is tricky software, but it's also fun and powerful. All right, let me get the lights off of the screen here so I can go back to what I'm doing. All right, so now we're going to do a written flip, just as we did before. And remember, in the written flip, you pull down on the side on one side and push up on the other side. Like so. And now you've got it. And the other side is pointing upwards. Rotate your model. Now rotate your model. Beautiful molecule. Now rotate your model. So your CH bonds are not staggered. Everything else is fantastic. Just rotate them out. Beautiful. Okay. I'm going to do the same thing over here. All right. And what I'm going to do is to draw out the methyl group. Actually, for starters, I'll just write it as CH3 and then I'm going to re-draw it. All right, so here we are. Now our methyl group has gone to the axial position. And the hydrogen has gone to the equatorial position. And looking around, I see a lot of correct ones. And I'm really happy on this, because this means you're starting to get it. You have a boat, or a twist boat here. All right, let me do this with the molecular models. And I want to talk about the energies of this. And let's see. I've done this the other way on there. So it's going to rotate. And I'm going to do this with the molecular models. And I'm going to do this with the molecular models. All right, so let's talk about this. This is the axial conformer. And what's bad about the axial methyl conformer, I think you can start to see, this methyl group is hitting into these hydrogen atoms. Let me draw this out explicitly. So I'll draw on my hydrogens, draw on this hydrogen here. Now the last thing I just want to do is to draw on the hydrogens on the methyl group. One's coming out, one's going back. And can you see how these hydrogens are hitting into each other? It's what we call steric hindrance when we talked about ghost butane. And in fact, there are two ghost butane type interactions. In other words, embedded in the molecule is one ghost butane on the front here and one ghost butane on the back. There are two bad hydrogen interactions where you have the methyl group's hydrogen hitting into those bottom two hydrogens. And those interactions each cost 0.9 kilocalories each. And so we have two of those in this case. So the axial conformer is 1.8 kilocalories per mole in energy higher than equatorial. You can really see it if you imagine your hydrogens taking up space. The hydrogens are of course not just little dots at the end of the rod. The hydrogens have a radius of 1.1 angstroms. And that means they're big enough to bang into each other. Here I can show you. I'll just make this into the spheres. If you want to do it, if I'm going to show you on the software, if you want to do it, you notice where my cursor is. That show means convert the atoms to. If I go show spheres, we get spheres. If I go hide spheres, you notice where I'm pulling h is hide. We get rid of them. So I'm just going to go back to show spheres. And now I'm just going to zoom in and rotate this guy. Let me stop rocking here for a moment. So we're looking at the bottom of the molecule. And you see those hydrogens right where my cursor is hitting into each other. That's these bad steric interactions. These hydrogens or spheres, they're banging into each other. The hydrogen on the axial methyl group is banging inward. We call these interactions 1, 3, diaxyl interactions. Now as you've received in the course, you're going to learn more about energy. I've been mentioning some numbers already. And I want to get more of a feeling later on, but I've got to remind you of things I've said. The energy barrier for rotating about ethane is 3 kilocalories per mole. That's a very low energy barrier. At room temperature, we cross it more than 10 million times per second. The energy barrier for flipping cyclonexane is 10 kilocalories per mole. At room temperature, we cross that energy barrier about a million times per second, a little more than a million times per second. That's a safe thing of grace. We'll learn more about this. We're going to start and talk about reaction to the wavelength diagram. But what I want to talk about now is difference in heights of the valleys. And we already saw this with butane. We saw that the butane, the ghost conformer of butane, was 0.9 kilocalories per mole higher in energy than the anticonfomer. Both the anticonfomer and the ghost conformer lie in a valley. The definition of a ghost conformer is stable conformation. But the ghost conformer is 0.9 kilocalories per mole less stable. Here we have 128 kilocalories per mole of energy difference. What that means is at room temperature, at 298 Kelvin, we have methylcyclohexane, 95% is in the anticonfomer. We'll say 95% methylcyclohexane. And 5% is in the case of monomer. The antotoxic, my brain is not connected. It has equatorial, thank you. Yes, 95% is in the equatorial conformer. 5% is in the axial conformer. My mouth is still on butane and my brain was somewhere else. Alright, I want to talk about making things really bad now. So let's go back to our axial conformer. So let me do one last thing, I'll embellish this drawing to show a big back arrow here to show that we are going back on our equilibrium. And now what I'd like to do is to talk about what happens if we go to a terpial group on cyclohexane. So, same drawings that I made before. But now what I'm going to do is a ring flip that puts the terpial group in the axial position. What do you think the implications are for the energy of the axial terpial cyclohexane conformer? No, no, this is great, don't be sorry. What do you think the energy implications are for your axial methyl axial terpial cyclohexane conformer? Really bad, yeah, really bad one-three-diaxical interactions. That terpial group just doesn't want to be axial, I'll make the longest back equilibrium arrow that I can possibly make. Terpial just manages to lock the methyl for the molecule into the equatorial conformer. Alright, let's explore one last situation here. Alright, let us explore this molecule. On the same face of the ring we have a terpial group and a methyl group. We call this the cisisomer, specifically cis one-turned-butyl 4-methylcylohexane. And now we have two choices. So this is our first exposure to stereoisomerism. This is the cis-stereoisomer. The trans-stereoisomer is the molecule in which they're opposite on the ring. So this is the trans here. And the cis puts us in an interesting position because now we have a choice. We can either have our terpial group equatorial and our methyl axial, or, and I guess I'll draw it right over here, we can ring flip to have our terpial group equatorial axial and our methyl group equatorial. Two different conformers. Now I just said something about the terpial group. This molecule has to make a choice. Does it want to be in the conformer on the left, or does it want to be in the conformer on the right? On the left. So you've got a choice. Dan if you do, really Dan if you don't, and as a result, the molecule adopts this conformation. This is the stable conformer. I'll call it more stable conformer, but in reality it's close to a thousand to one times more stable. So the molecule very strongly diverses conformation. Alright, well this is where we will stop. Next time we will start picking up more on the ideas of stereowide samaritans.
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Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: -1:43 Chair Conformation -5:08 How to Draw a Chair -10:20 Cyclohexane Graphic and Computer Model -15:30 Methylcyclohexane Conformations -23:30 Steric Hinderance with Methylcyclohexane -31:07 Tert-Butylcyclohexane -34:05 1-tert-butyl-4-methylcyclohexane
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10.5446/20476 (DOI)
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So, we'll just continue where we were last time and I'll review a little bit more about the profiles. Okay? Just to begin. So, this is still from last time, okay? So, it's the same. I didn't change. So, we have a bounded sequence and for each J we have a solution of a linear wave equation and we have a sequence of parameters. So, the lambdas are the scaling parameters, the axis are the translation parameters and the T are the time translation parameters. And I'm not entirely consistent in how I write this. So, sometimes the J's go on top, sometimes they go on the bottom, sometimes the N comes forward, sometimes the J comes forward. So, anyway, from the context it should be clear. Okay? And we call this sequence of triples orthogonal. Sometimes we say it's almost orthogonal. If these ratios have the property that their sum goes to infinity, so that means that at least one of them goes to infinity. Okay? And if the sequence of parameters is orthogonal and this is a sequence of solutions of the linear wave equation which we then modulate according to these triples and we find this thing and then we look at the difference between the linear solution corresponding to our given sequence and the sums of the profiles modulated. And this error has to, first of all, remain uniformly bounded but also it has to go to zero in the sense of the spacetime norm. Okay? So this is, in the case we were looking at, this is the L8 norm. I'm slightly confused. The UjL are solutions of the... Linear wave equation. Yes. But what happens if you take, for instance, a well localized solution and you may have a Lorentz boosted unit that can occur. Yes, and that's... I'm slightly surprised that if you have a Lorentz boosted and you expect it to have x proportional to t and then you localize both in x and t. Yeah, but you can translate it in t. You're translating in t. And the other thing is that your Lorentz boosts are limited because they keep the bounded sequence in h1 cross l2. So the sequence xgl tgl, if it's a Lorentz boosted solution, can be proportional and travel at the appropriate speed. Yes. So that's why you include the time translation stuff. Okay? But the speeds cannot go to one because of the uniform bound on the energy norm of u0 and u1. Okay? So the Lorentz boosts are compactified by that. Okay? And I don't know what happened. This? Mm-hmm. Oh, I was away from it too long? You think I was... I didn't move it for too long or... Why do you think... Yeah, that's what happened. Okay. Is it plugged? Pardon me? Yeah. Yeah, everything seems to be plugged. Okay, so let's keep on going and then it goes to zero in the late norm, but it also goes to zero in most of the other Strikert's norms. And as I was mentioning last time, the only one that it does not go to zero unnecessarily is the so-called Kiel-Tau endpoint. This actually is false that it goes to zero in that. In fact, we discovered this recently. Okay. So then there's a remark as to how these ujls are constructed from the given sequence. You construct them from the given sequence by taking an orthogonal set of parameters and then taking the linear solution at these ratios and then taking weak limits. Okay. That's how these profiles are constructed. And the fact that this object goes weakly in h1 cross l2 to this one is a consequence of the fact that these errors provided you scale them before the capital J, they all have to go weakly to zero. Okay. And then I remember we have from the orthogonality of the parameters these Pythagorean expansions. Okay. And I mentioned last time that Pythagorean expansions have to be taken carefully because if you separate, for instance, they are not true. They may fail. And this was a big surprise for us. But it's true. You have counter examples to that. But there's this substitute where here the core indices are the ones for which Tjn is identically zero and the scattering indices are the ones for which absolute value of Tjn or lambda jn goes to infinity. And so you recover these forbidden Pythagorean expansions provided you keep together the scattering ones. Okay. But you can separate off the core ones. Okay. So one cannot be too overconfident in dealing with these profiles. One has to be extremely careful. Okay. It's very easy to fool oneself. And believe me, we've done this. So, okay. But of course you could say, okay, you had this Pythagorean expansion, but maybe that didn't work. Maybe if you chose a different profile decomposition, it could have worked. And the answer to that is no, because there's a certain uniqueness. Okay. So the first statement is that if you change the parameters in such a way that this limit exists and is nonzero and this limit exists and this other limit exists, then you get and you renormalize your profiles by this recipe, you do get a new profile decomposition. But then there's a result that says that this is the only way to get a different profile decomposition. Okay. And it's using this kind of transformations that you can always reduce these parameters tjn to be either identically zero or such that the absolute value of tjn over lambda jn tends to infinity. Okay. Those are the three options. Yes. When you're comparing the two, you have to make a further subsequent extraction. Yes. Yes. So we never blink at taking further subsequent extractions. We don't even think about it. We automatically extract. Okay. Okay. So this is the uniqueness result. And now there's another remark that says that whenever you have a sequence and this thing has a weak limit, this arises as a profile, possibly after some of the transformations that we had before. Okay. So all such weak limits arise as profiles. Okay. So the next thing that I want to say is I want to discuss how do we use this for nonlinear problems because up to now we've only been dealing with linear profiles and linear solutions. And in order to use this in the nonlinear situation, we introduced the notion of nonlinear profile. And remember last time I was talking about the compositions into blocks. The blocks are the nonlinear profiles. Okay. That's the technical thing. And what is a nonlinear profile? Well, we look at the sequence minus Tjn lambda jn. And we look at our linear profile evaluated at that sequence of times. And then we find the nonlinear solution such that this limit is zero. Now this nonlinear profiles always exist because there are two situations. If it Tjn or lambda jn has a finite limit, then you just solve a nonlinear wave equation at that finite limit and then you get this. If it goes to plus infinity, what you do is you solve the equation at infinity. So that's like what they call the existence of the wave operator. Okay. Sorry. Okay. And so there's no linear profiles always exist. And again, by extraction, we can always assume that this limit exists. In the case when it is finite, we might as well think that it is zero because by a time translation and changing the profile, we can take it away. And otherwise it's plus infinity or minus infinity. Okay. In this formalism, all limits, all sequences have limits. Don't tell this to your calculus students, but okay. All sequences have limits. So if the limit is infinite, then it's a scattering solution? Yeah. It's like the final state. It's the wave operator. That's all. Okay. And because of this construction, if it's a scattering solution, as Janet says, then you see that if the limit is minus infinity, the time of existence for this nonlinear profile is minus infinity and the nonlinear solution scatters at minus infinity by construction. And the same at plus infinity. Okay, this is just because you construct it by scattering. Okay. So now we look at the modulated nonlinear solutions. Okay, we can still do that. And of course, the maximal, let's say positive time of existence of this modulated solution can be obtained from the old one by this formula. There's nothing. This is just arithmetic and it's plus infinity if this is plus infinity. And so we have this approximation theorem that is a very important tool for us. It tells us that if we have a profile decomposition and we control all the strictest norms of the blocks, then we can write the solution as a sum of the blocks plus a small error. Okay. That's, so the first case of this theorem is the easiest to state. It says that if all the solutions, if all the nonlinear profiles scatter forward in time, then the, our nonlinear solution minus the sum of the nonlinear profiles minus the linear solution associated with the remainders in the profile decomposition actually goes to zero in a very strong sense. Okay. So when I was saying in the first lecture that we look at each block in the nonlinear solution, this is what I meant. We use this kind of decomposition. So you may have a situation of where some of the profiles have already blown up, but not all. And in between the two, you don't know what happens. No. So here is what we can say then. Then you can go as far as in time as far as all the strictest norm remain bounded of the nonlinear profiles. So suppose we take a time theta n such that it's always within the time, the forward time of existence of the ujn. And suppose that up to that time, the strictest norms remains bounded uniformly in n. Then you can still do this. So then the nonlinear solution is defined up to that time. The strictest norms remain bounded. We have the sum and the error goes to zero, but only up to that time theta n. But you are not saying anything if the theta n is bigger than the blow time of some of the g, but not of all. No. I have to be smaller than all the blow up times. No. Otherwise, I'd have something that is impossible. So that would be too good to be true. So this is a sufficient condition for this. It's either they all have very small h1 cross l2 norm, the profiles, or all the parameters are scattering. That's another possibility. Or this theta n stays strictly away from the final time of the ujn. And then in this case, you can do that. So I have some remarks about the proof. First this l8 norm can also be taken to be the l5 l10 norm. Those are more or less fungible norms. Now the proof of this theorem uses this thing I described as the long time perturbation theorem. And it also uses very strongly this kind of orthogonality property for the l8 norm to the 8th of this modulated nonlinear profiles. So this is kind of a Pythagorean expansion for the l8 norm. So a very important consequence of this approximation theorem is the fact that these Pythagorean expansions that held for the linear profile decomposition also hold for these nonlinear profile expansions up to any time strictly smaller than this theta n. So we have this fact, this fact, we have the same thing for the n6 norm and so on. And this is because morally, well not morally, in actuality you can see that if this converges which you can do after extraction, you can make the nonlinear profile decomposition into a linear profile decomposition. You manufacture the linear profile that corresponds to the appropriate nonlinear profile depending on the parameter sj. Okay? Okay, so I will not torture you anymore with profiles. This is a kind of a tricky business but I will put down all the relevant things now. Okay? So now we move on. And what we're going to do is first, there's a number of things about elliptic equations that we need. And so I'll start by developing those. So we need properties of solutions of the elliptic equation and some variational estimates. Okay? And that's what we start out with now. So again, this is the associated nonlinear elliptic equation and we call sigma the nonzero solutions. There's this explicit solution which is well known from the Yamawe problem. And as I said last time, this is up to translation and scaling the only nonnegative solution. And that's the result of Gidesonian Ermerg. And if I don't translate, these are the only radial solutions with a plus and a minus. And this combines work of Bohorzai, Gidesonian Ermerg and Kuang. So Kuang somehow does it for ODE solutions, I mean the radial case. Bohorzai reduces to the radial case and Gidesonian Ermerg gives you some decay properties. Okay? So we have to put all this elliptic machinery together, but the summary is simple. As I was saying last time, sometimes you can summarize in two or three sentences, maybe 25 years of work. Okay? But that's okay. It's convenient for us who didn't do the work, just summarize. Okay. So as I was saying last time, this W is also called the ground state. So let's recall the Sobolev inequality in 3D. We're in 3D, if the gradient is in L2, the function is in L6. And there's a best constant, and I will call this best constant C3. Okay? C3 is a known number. It was calculated, I think, by bliss already. It has a pi's and gamma functions and so on. But it's a known quantity. So this C3 is not some positive constant, but a known positive constant. Okay? And the one way in which W is extremal is that it gives you equality in this inequality, and modulo scaling and translation is the only non-zero function for which you have equality. Okay? So that's the theorem of Oban and Talenti. Now let me go back to the elliptic equation, multiply this by Q and integrate by parts. Then you see that Q to the 6, the integral of Q to the 6 equals the gradient of Q squared. The integral. Okay? So this is a piece of information that we will use. So since this is a solution of a non-linear equation, this holds. And we know that this holds because this is an extremal. So that means that we have a formula for this. Okay? Because we have two equations that we can solve and this is what you get. The gradient of W squared is this best constant to the power minus 3. Okay? So this is just what... And now we're going to calculate the energy of this W. The formula for the energy is 1 half gradient minus 1 6 W to the 6. But these two numbers are the same. So it's 1 third grad W squared. So we know that grad W squared is C3 minus 3 over 3. So this is this and it's that. Okay? So this is a point where you heavily use a treaty guarantee. Absolutely. And where you heavily use the variational characterization of the ground state. Now because of these things, W is the elliptic solution, the non-zero elliptic solution with the least energy. Okay? So I'm going to now give you a way in which this W is isolated in the set of solutions to the elliptic equation. Okay? So this is a theorem that says that if I have a solution and it's L2 norm of the gradient doesn't reach twice the one of W, it can only be W. So to be above W, you have to go up a fixed amount. Okay? So let's prove this. I'll sketch the proof here. It's a simple proof. We define Q plus and Q minus. And then the first observation is kato's inequality tells you kato's inequality tells you that the Laplacian of the positive part of a function is bigger than or equal to the positive part of the Laplacian. Okay? And so in this case kato's inequality gives you this. You multiply by Q plus again and you get this inequality. And similarly you get the corresponding inequality for Q minus. And we know that they add up to less than twice the one of W. So one of the two has to be smaller than W than one. Right? If both are bigger than two, you can't be less than twice. So let's assume that the Q minus is the one that's smaller. We will show that then it has to be zero. Why is that? Because Q minus by the integration by parts, the gradient is less than the L6 inequality. You use the solvular inequality with the best constant to go to the gradient. Now we use that this number is this and we get to this. And so now we read off from here that either this number is zero or I can divide by this number and get this. But this is a contradiction because we started out by assuming that this was less than. Okay? So the assumption that Q minus was not identically zero is absurd. So Q minus is identically zero. If Q minus is identically zero, Q is non-negative. If Q is non-negative by Gieda's name Nierenberg, it has to be W. Okay? I think this is a kind of a folklore argument. I don't know where it is in print, but it's a folklore argument. Okay? So it's a fact about elliptic equations. And as a corollary, you can use these very simply to show that if you have a solution whose energy is smaller than the energy of W, then it has to be W. Okay? And it just follows from this. By the elliptic equation, this equals that. And then because of this, you get this. But if you get this, you have to be W. All right? And in fact, if you precise this calculation, you see that any other solution has to have energy strictly above the energy of W. There's a gap in the nonlinear spectrum, whatever you want to call that. Okay? So now I'm going to use some properties of the ground state, these variational characterizations, to prove some variational estimates that allow me to completely understand the situation as far as the global dynamics provided the energy is smaller than the energy of W. Okay? So this is what Merrill and I proved, I guess, about 10 years ago. Okay? And which, in a sense, is the beginning of the story. Okay? So, now we're going to do a little bit of calculus, okay? True, one variable calculus. So this variational lemma says that suppose that my gradient is smaller than the gradient of W and its energy is strictly smaller than the energy of W, by an amount delta naught. Then there is a block, so we call this energy trapping. It tells you that the gradient, instead of just being smaller, is smaller by a definite amount. Okay? And not only that, but there's a certain coarsivity going on. Okay? And in particular, the energy is strictly positive, or zero, of course. Okay? So let's see the proof of this. As I was saying, the proof is calculus. I'm going to form the following one variable function, 1 half y minus 1 6 C3 to the 6 y cubed. Okay? This is a function of one variable. The first thing I notice that the y bar is the gradient squared, then this is less than the energy. And this is just the fact that C3 is the best constant in the sum of inequality. Okay? Nothing more than that. The next thing I'm going to do is I'm going to find the non-positive zeros of this function. Of course, that involves solving a simple quadratic equation, so we can do that. So for positive y, this is zero, if and only if it is zero, or 3 to the 1 half grad w square. So the zeros are at a fixed amount higher than grad w squared. 3 to the 1 half is strictly bigger than 1. Okay? Then the next thing we're going to find is what the critical points are. Okay? So for the critical points, we differentiate and find the zeros. And it's exactly 1 over C3 cubed, which if you remember, that's the L2 norm of the gradient of w squared. It's the integral of grad w squared. Okay? And add this, so here it is. And what is the value of f at its critical point? Well, it's exactly one-third of C3, and that is the energy of w. So this w appears for this one variable function. So f is non-negative, and it's strictly increasing before you hit the first critical point, because for y small, it is clearly increasing because we have the power 1 and the power cube. Okay? But also this critical point is non-degenerate because you can see that the second derivative will be strictly positive for y positive because it's, you can compute it, it's a cubic polynomial. Okay? So what does that mean? It means that f is strictly increasing up to when I get to the critical value. And at the critical value, I have the value of the energy of w. Now I am assuming that I'm a fixed amount below in energy, that critical value. That means that f of the gradient is a specific fixed amount below, and therefore the inverse function is a strictly, a strict amount below the gradient of w squared. And that proves the first part. I recall what the first part is. It's that. It's just the monotonicity of f near there. Okay? And you can calculate what this delta bar in terms of this delta is. There's a square root involved. But anyway, it's there. And now we are going to prove the other inequality. And the other inequality comes very simply from the first inequality. So here we go to here by the Soveless embedding. Now we take out this common factor. And now we see that C3 to the 6 is the gradient w squared. And then this is smaller than 1 minus delta squared, gradient of w squared. So this and this cancel out, and we get this. And this is strictly, strictly positive. Because delta bar is positive. Okay? And that's how you get the coarsivity. All right. The next thing that I want to point out is that this proof shows that if you are below the first zero of this function, little f, your energy has to be positive. Because little f is bounded by the energy. And if little f is positive, the energy is positive. And this value was the first zero. So the energy remains positive a little bit beyond the ball of radius grad w squared. And the amount is 3 to the 1 half. Okay? Okay. So now I need to study some properties of general solutions and their Lorentz transforms. Remember that the traveling wave solutions I claimed were Lorentz transforms. I'm going to prove that now. Okay? So you need a little bit of information about solutions to the elliptic equation. Maybe it'd be good if I write on the board the elliptic equation. Okay. That's the elliptic equation. And so elliptic regularity theorem immediately gives you that if you have a solution, it will be the infinity. Okay? And this is where lower dimensions are better than very high dimensions here. Q to the 5 is a very nice power. Q to the 7th and 3rd is not so great. Which is what you get in dimension 5, for example. Anyway, so let's stick to Q to the 5. So Q is the infinity. And the next thing that we're going to see is that Q has decay at infinity. And the decay is the decay of W. W is the one that gives you the slowest decay at infinity. How do you see this? Well there's a simple way of seeing it which uses the Kelvin transform. If you remember when you studied harmonic functions, you can do the Kelvin transformation and you still have a harmonic function. In 3D the Kelvin transform is 1 over length of x, f of x over x squared. Okay? Now it turns out that the Kelvin transform also preserves solutions of the nonlinear elliptic equation. So that equation is invariant under conformal transformations of R3. And the Kelvin transform then does that. And so you can pull infinity to a bounded point by the Kelvin transform. You pull infinity to the origin and you use the solutions of the nonlinear equation or smooth at the origin and that gives you this decay. Okay? So that's all there is to it. All right? So the next thing I'm going to do is I'm going to prove a certain identity. The L2 norm of each partial is a third of all the full gradients. So all the partials have the same L2 norm. Of course for w this is obvious by the invariant and the rotations. But for any other w you can prove it just by multiplying the equation by this expression. You multiply the equation by this expression. It seems to be temperamental today, I don't know. Okay? You multiply the equation by this and integrate by parts and you see that the terms from infinity go away because of the decay estimates. Okay? So that's why I'm stating the decay estimates. And when you unravel that you get this identity. Okay? And this is something we like, this identity plays a role. Now I take a vector of length less than 1 and I take my q and I view it as if it were a function of x and t constant in t. And I do the Lorentz transform of that function in x and t. And then what I, in the direction given by L. What I get is this horrendous mess. So don't pay any attention to it. The important thing is that it is a function of this form. X minus t times L. So it's translated, it's been translated in the direction given by L for each t. And what is the function q sub L what you get by making t equals 0 here. Okay? Okay, so don't look at this too much because it's not going to help. But what is interesting is that if we do a rotation in the x variable we can make this L to be a little L times E1. Okay? That's certainly possible. And these equations are invariant in the rotation so that's allowable. And little L times E1 when you do the Lorentz transform in the direction given by L times E1 you have a very specific formula that I gave last time. Where the x1 goes to x1 minus Lt over the square root of 1 minus L squared and the t goes to x, the t goes to t minus Lx1 over the square root of 1 minus L squared. And the x2 and x3 are not touched. Okay? Now this q, this Lorentz transforms of the q have some interesting properties which of course is nothing more than changing variables and chasing everything around. The one thing I want to point out now though is that the effect of the Lorentz transform is to make the energy bigger. Okay? And control on the energy gives you a control of how far L is from 1 by this identity. And remember that this is a positive number for all solutions of the elliptic equation the energy is strictly, all non-zero solutions, is strictly positive because it's strictly bigger than the energy of q and the energy of q was one third of the best constant in the solve of inequality to the power of 3 or something like that. Okay? So we saw all these numbers. Okay. So let me show now that all traveling waves are of the form qL for some q a solution of the non-linear elliptic equation. And this is something that we proved in, I worked with De Kuyrer and Merle. The real proof was done in 2011 but that was not clarified sufficiently in 2014. We have the explicit proof. Okay? So I start with a function f of xt which is a traveling wave function with f in h1 and suppose that this solves the non-linear wave equation. Okay? So I have a solitary wave for the non-linear wave equation. So the claim is that then f has to be q sub L for a q solution to the elliptic equation. All right? And this is important for us because if we're going to do solid and resolution and we want to decompose things into sums of modulated traveling waves, it's a good thing to know when the traveling waves have to be. Right? Okay. So this is the point of this calculation. Okay. So again we can do spatial rotation on this f. This f is a function on R3. So we do a spatial rotation so that L is little L times e1. So then f is of this form. And now I plug in what does it mean to solve the non-linear wave equation. And that's this. And you see the 1 minus L squared factor in front of d dx1. Okay? And let me assume for this proof for simplicity that L is positive. Okay? The case L is negative. It just changes t into minus t. So it's not. So but I have this equation. And this proposition says that suppose f is a non-zero function, L is in R, and that equation holds, then necessarily L squared is less than 1. And there's a Q solution of the elliptic equation such that it's the Lorentz transform of that solution. Okay? So the proof goes, there are three different cases. First case is L squared is bigger than 1. If L squared is bigger than 1, this really cannot happen because of finite speed of propagation. So you just have to produce the argument that shows that. And the argument is as follows, I call u of xt this thing where I am undoing the LT here. So this is a global in time solution. It's gradient at 0 is f and its t derivative is L d dx1. So because f is in h1, I can find a large m, given an epsilon, I find a large m such that this is small. So the tails are going to be small, at time 0. But if the tails at time 0 are small, by finite speed of propagation, I get this propagating into the future. And so if I give up a little bit on the m, I need to give up a little bit to use some cutoff function to be able to use the finite speed of propagation. Then I get that for all time t, this is smaller than some constant times epsilon. And the constant comes from the smooth truncation that I have to do. So once I have that, I look at the compact set in x2 and x3 and two numbers, a and b. And the first observation is that if t is large and I have x1 in this interval and x2 in x3 in this interval, then I know that the length of x has to be bigger than LT. And that's because this L is bigger than 1. And I'm moving only by t here, by LT. That's one way of using that L is bigger than 1. So once we know that, if I look at this, of course I have this fact from the finite speed of propagation. But I have my formula for u and I do change these variables and I get that this thing equals that. But so this thing for fix k and fix a and b is smaller than c epsilon for every epsilon. So this thing has to be 0 and so f has to be 0. Now the tricky case is when L is 1, because then this argument just does not work. And that's where you, the way you get out of it is you go back to elliptic theory, but you're going to use elliptic theory in R2 instead of in R3. So because remember that the factor in front of the d dx1 is 1 minus L squared. When L is 1, that factor is 0. So your equation, your function verifies an equation in two variables instead of in three variables. So my f verifies this equation in these two variables and it's for almost every x1 has some regularity. So we fix such an f1 and we let f be this and we'll show that f is 0 by using Pohojai's argument. And the idea in Pohojai's argument is that from the equation you get this identity which you can check by Leibniz's rule. And from this identity you integrate by parts, integrate by parts both sides. If I integrate this side I get 0 because I'm integrating a divergence. And when I integrate this, the only thing that happens is that this falls on this and that gives me a 4 over 6. There's a 2 from this divergence, a 2 from the formula and a 6 from there. And so the conclusion is that f to the 6 is 0. If f to the 6 is 0, f is 0 and so that's the case L is less than 1. L is equal to 1. And to justify the integration by parts you use a truncation argument. So I won't bother with that. Now finally assume that L squared is less than 1 and now I fixed then the first variable problem by doing this. If I do this, now I verify the usual equation from this equation with the 1 minus L squared and that's the elliptic equation. So f verifies the elliptic equation and L squared has to be less than 1. So these are the traveling waves. So let's start now with the proof of this ground state conjecture. So this uses this concentration compactness rigidity theorem method. So let me start reminding you of the precise statement of this theorem. So the precise statement is suppose we have a solution and its energy is smaller than the energy of W and let U be the corresponding solution of the nonlinear problem. Then if the gradient is smaller than the gradient of W then the solution exists for all times in both time directions and scatters in both directions. And if it is strictly bigger then it blows up in both time directions. And then you say okay you're missing a case which is this but it turns out that that case doesn't exist. There's no such function. The energy constraints and this are incompatible. There's no such function. What about U0 equal to UU equal to 1, 0? The strict inequality here. The strict inequality in the energy. In fact the case where energy of U0 equals energy of W0 is a very interesting case that was solved in a paper by Ducca and Merrill. They classified what happens. And there you either scatter in both time directions or in this case you scatter in one direction and you go to some new object called W minus in the other direction. And in this case either you blow up in both time directions or you blow up in one of the time directions and in the other one you go to another object called W plus. But I'm not going to enter into that today. So that is a legitimate case. Let's look at it. So let's look at this. So there are three things to prove. And of these three things to prove, the last two are more or less simple consequences of the variational estimates that we have. Again the real content is property 1. So remember that from the local theory of the Cauchy problem this condition is equivalent to scattering. So this is what I would say the hard part of the theorem. But let me dispose of the other two parts first. And then we will start developing the theory that goes into this. Okay. So to deal with the third point I will recall another variational estimate which is quite useful. It says that if the gradient is less than or equal to the gradient of W and the energy is less than or equal to the energy of W, then the gradient squared is, so a way to say it is that the ratio of the gradient squares is less than the ratio of the energies. Okay. So let's prove that. And we, the first thing that I'm going to do is use this claim to show that there cannot be something with energies less than the energy of W and gradient equal to the gradient of W. Okay. Why is that? Because if the gradients are equal then the ratio of the energy of W and the energy of B divided by the energy of W is bigger than or equal to 1 from this inequality. But it's also strictly less than 1 by assumption. So that's the contradiction. So this claim immediately gives that that third case is not possible. Is that clear? It's just that the ratio of the gradient of V and the gradient of W is 1 so this ratio of energy has to be bigger than or equal to 1 but we know it is less than 1. Okay. So now let's prove the claim. Again we use the same function of one variable that we used before, this polynomial of degree 3. And we notice that f of 0 is 0. Okay. f of grad W square is the energy. We already saw that. And f in a gradient is smaller than the energy by the solvable inequality. The next observation is that this f is concave because its second derivative is negative. Why is it for s positive? Why is it negative? Because it's minus a constant times s. Degree 3 polynomial. So we can check that it's concave. So since it's concave and f of 0 is 0 and f of 1, so I look at f of s grad W squared, that's a concave function. And at 1 it equals the energy of W squared at 0 it is 0 so the concavity gives me this. So f of grad W squared is bigger than or equal to s times the energy of W common 0. And now I choose this s. And I plug it in and it gives me precisely the claim. So these arguments are very simple calculus arguments. But of course we have to know what to plug in. So this takes care of 3. Now I will prove 2 and there is an extra assumption that the u0 is in L2. So 2 says that if the energy is smaller but the gradient is bigger it will blow up. So I will do it for functions in L2. We can pass to the general case by truncation using finite speed of propagation. So let me just do this case. So the first thing is that this argument with this function little f which we first did when the gradient was smaller than the gradient of W also has a version when you pass the critical point. So when you pass the critical point the f was increasing you get to the critical point and now you start to go down. So that means that if you start out with the gradient being bigger it will stay a definite amount bigger. It's the same argument but on the other side of the critical point. So this variational estimate tells you that if the energy is smaller by delta 0 and it is bigger then it's a certain amount bigger. So using this this is a static argument. Now you can plug it into the flow. The flow preserves the energy. So if I start out with the energy being smaller it will continue being smaller. And if the gradient was bigger it's now bigger by a certain amount so for a little bit of time it will still remain bigger than the gradient of W. But then I reapply the static argument and I get a fixed amount bigger. And then by continuity of the flow while the flow is continuous it will remain strictly bigger. So it's a continuity argument. So for all t in the maximal interval this is a certain amount bigger. So the argument that we use for the blow up is an argument that goes back to work of Harold Levine in the... I don't know what I did. Anyway this is from the early 70s. And it's an argument that's been used for blow up problems similar to arguments of Zakharov and Glassy for the Schrodinger equation. Alright so now I'm saying that the energy is smaller than the energy of W. And so there's a certain amount delta for which it is still bigger. Since it's strictly bigger you have room to put in a little bit. And now I solve for the term u to the 6 in this inequality and this is what I get. Okay I put this on the other side, the u to the 6 on this side and this is what I get. And now I multiply by 6 and this is what I get. I will actually in the next slide multiply this by 2. So if I multiply by 2 here I have 6, here I have 6 and here I have 12. So let's remember that. Okay so now let's go. So now we go to the actual proof. I call y of t equal u squared. And that's why I needed to assume that u was in L2 so that this makes sense. And y prime is 2u t d t u t. This is clear. What's more interesting is the calculation of y double prime. And this is one of these virial identities that I was talking about last time. And there's this identity. And I can leave you to check that, it's nothing more than plugging in the equation and integrating by parts. Okay. So now I use now my inequality from below for 2u t to the 6. That was in the previous slide. And so I still get this 2u t squared. Now I get the 6. And here I have a 6 on this but minus a 2 gives me a plus 4. And then I have the minus 12. Energy of w are now I have some other positive constant. Okay I just plugged it in. That's all I did. And now I add 2 plus 6. It gives me 8. And I remember that 3 times the energy is the gradient for w. So then I have the 4 minus 4 because 12 times is 3 times 4. Okay. And you get that. And now remember that the gradient of u t squared remains strictly bigger than the gradient of w squared. So I'll throw it away. And I get this inequality from below. Okay. So assume that my interval of existence goes all the way to plus infinity. And I'm going to see that that cannot be. Then you see this function is strictly increasing. Why double prime is I mean why prime is strictly increasing. Why double prime is strictly positive. So why prime is strictly increasing so eventually will become positive. It exists for all times. It will become positive and then it will increase from that point on and remain positive. So there's certainly a t naught for which y prime is positive. So for t bigger than t naught I multiply this inequality by y which is u squared. And I forget the delta. And I get this. But this we recognize from Cauchy-Schwarz that it's bigger than twice y prime squared because y prime is 2u dt. And so when I look at this I get y double prime over y prime is bigger than 2y prime over y. And I can do this because y prime never vanishes because I showed that it was strictly positive for t bigger than t naught. But I know how to solve this over the e. This tells me that y prime is bigger than some constant times y squared. But that over the e blows up. So this cannot live for all time. Okay. So that's the argument. So if the energy is smaller than the energy of w and the gradient is bigger it has to blow up. And I did it in the positive time direction but in the negative it's the same. Look. I think it's messing with me. Okay. So now the first thing is the heart of the matter in this theorem. So the first statement is that if the energy is smaller than the energy of w and the gradient is smaller than the gradient of w the solution exists globally and scatters. Okay. So now we are going to develop a machine to prove that. This is not a few lines. Okay. It'll take us until next time. Not just today but it will go on. Okay. But let's be patient and set it up. All right. The first thing I'm going to do is I'm going to use my variational estimates. Okay. What do my variational estimates say? That if I start with data which is strictly smaller and the gradient is smaller then for all time of existence this remains small and this remains big. Okay. That was the variational estimates. But notice that this statement in particular implies that the energy is non-negative because the energy has a one-half and a one-sixth and this has one and one. Okay. Moreover, because of this lower bound you can actually say that the energy is comparable to the h1 cross l2 norm at each time. Because the energy is certainly bounded by this but by this lower bound it's bounded from below by it. The DDT just sits there. Okay. And this is comparable to the initial h1 cross l2 norm y because the energy is constant. So this energy is the energy at time zero and at time zero this equivalence holds. So what is the situation then? The situation is my norm is under control. But that does not mean that my solution exists globally in scatters because we have the examples of Kruger-Schlag and Tataru that have this property but cease to exist in finite time. So we have to exclude that that happens. And this is of course non-trivial. Because that happens by concentration. So we have to see that our size constraint excludes their example. Okay. So now I'm going to use the concentration compactness procedure. To use the concentration compactness procedure I introduce the following statement. And I call it scattering, SC. For all u0 with h1 cross l2 such that the gradient is smaller than the gradient of w and the energy is smaller than the energy of w then the corresponding solution is global and scatters. That's a statement that I would like to prove. SC. Okay. That's my theorem is SC is true. Okay. So now I'm going to say that the fixed function which verifies this hypothesis, the size constraint we say that SC of u0, u1 holds if for this solution on its maximal interval this l8 norm is finite. So that's the same as saying that the maximal interval is r and the solution scatters on both time directions. Okay. So that from the scattering criteria in terms of the space time norm or the stricter norm being finite. So now we're going to start slowly. Yes? You will see if my is finite uniformly i. No i is the maximal interval. Okay. Okay. So I'm always using the maximal interval for i. Okay. So now I'm going to start and I start by saying that if the data is small certainly S of C of u0, u1 holds by the local theory. Right. If I have small data I showed or I claimed that the solution exists globally in scatters. Okay. But now I translate this in terms of the energy. If we're looking at data whose energy is smaller than the energy of w and gradient smaller than the gradient of w, the energy being small and the h1 cross l2 norm being small are equivalent. Okay. So remember we had this equivalence. Okay. So I know that there is some eta0 positives such that if u0 verifies our hypothesis and its energy is really small then scattering holds for this u0, u1. There's nothing more than a combination of variational estimates and small data theory. Okay. So what is my strategy? My strategy is to start increasing the energy. I'll start increasing the energy slowly until the first time that something goes wrong. And my goal is that that first time is the level of energy of w. Okay. So that's the strategy. That's the concentration compactness procedure. Of course this cannot be just done like this. Everyone has to actually do some math, right? So I'm going to call e sub c the smallest level of energy. So e sub c will be a constant such that if u0, u1 verifies the hypothesis and the energy is strictly less than e sub c then scattering holds. And I will look at the optimal e sub c with this property. Okay. And we know that this e sub c has to be strictly less, strictly bigger than some number eta0. And I'm only considering numbers smaller than the, smaller than or equal to the energy of w. Okay. So my goal then, my theorem is the statement e sub c equals the energy of w. If e sub c equals the energy of w then my theorem is true. So I proceed by contradiction and I assume that e sub c is strictly smaller than the energy of w. And then if we're patient we will reach a contradiction. But the contradiction comes after a very long time. Okay. So bear with me. So this is the strategy. So we assume that e sub c is strictly smaller and we reach a contradiction. So the contradiction is reached because of the, of three different events. So the first event is that there is an element in H1 cross L2 whose energy is the critical level of energy and therefore smaller than Ew. Its gradient is smaller than the gradient of w. And the solution corresponding to it actually has doesn't scatter. So this critical level of energy is realized by some function, the critical data. Okay. So that's the first thing to prove. The second thing to prove is that this critical functions, so these are very bad functions, right? So the next statement is they negate our theorem. So they're very bad functions. So the next statement is that these functions have a redeeming property. They're not all that bad. And what is the redeeming property? The redeeming property is a certain in the, in the compossibility of these functions. These functions cannot be torn apart. And that is precisely expressed in terms of the following mathematical statement. That you can find a scaling parameter lambda and a translation parameter x such that for such a critical function, let's say that the, the thing goes bad to the positive side. It either goes bad to the positive side or to the negative side. So let's assume it goes bad to the positive side. Of course, it could go bad for both, but that's even better. Then for on the positive side, we can find these modulations such that this thing behaves as if it were a single function, sort of as a singleton so that there's a specific formula for this. And that means that the trajectory of this is compact. Of course, it's not a singleton, but the next best thing to being a singleton is being a compact set in this infinite dimensional space. So this is the redeeming feature. And this is a very non-dispersive property because it's easy to see that solutions of the, it's a nonlinear statement because solutions of the linear equation, if they have this compactness property, they have to be zero. Okay? This is a simple fact. And then the third part, the rigidity theorem part, so this is kind of like a Lueville theorem. So the Lueville theorem says, suppose we have a solution like this, verifying our size conditions. Then the only possibility is that it be zero. Okay? So there can't be such an object with this nonlinear behavior. But this guy cannot be zero because its level of energy was the critical level of energy and the critical level of energy was positive, was bigger than this eight and a half. And that's the contradiction. So you have to wait quite a while to reach the contradiction. Okay? Okay. So in my notes, I wrote a very detailed proof of this. But I then realized that I would bore everybody to tears if I gave this detailed proof. So instead of giving you a detailed proof, I'm going to give you the idea of why this is true. Okay? So let's start with the first, sorry, by that, let me qualify that. The proofs of proposition A and proposition B are tedious. I'm sorry to say that. And lengthy and so on. And they use heavily the profiled decomposition. But so I'll sketch the idea for the proof of those and then give the complete proof of the rigidity theorem that says that there's no such object which is nonzero. Okay? And that I think is kind of the most important part of the proof. The other parts are easier to understand conceptually. Okay? So let me explain why proposition A is true. Okay? So how would we prove proposition A? I mean, what would be the most naive way of proving proposition A? So this is the critical level of energy. So if we go slightly higher than it, things will go very bad. So for each number N, there would be a function, a pair of size of whose energy is EC plus one over N such that the S norm would be infinite. By definition of being the critical level of energy. And the fact that it's strictly below the energy of W. So I can go a little bit above and still not reach the energy of W. So something has to go bad. If it goes bad, it means that the S norm is infinite. And then what you would do if you are naive is you would say, okay, now these are uniformly bounded functions and let's pass to the limit. Of course, you cannot take a strong limit, but let's take a weak limit. And what happens if you try to do that in this naive way is that you fail because you're at a critical level and you cannot exchange weak conversions and non-linearity when you are at the critical level of energy. So what you have to do is use the profile decomposition to substitute for this failure of compactness. Okay? So this makes complete sense. So what do you do? How do you use the profile decomposition? Okay, so now we take the profile decomposition of this sequence of functions. The first thing that you will observe is that for all these profiles, the energy is positive. Why is it positive? Because of the Pythagorean orthogonality conditions, the energy and the gradient will be smaller than the ones of W and we know that if we are a certain amount smaller than W, then the energy remains positive. So all of these guys will have positive energy as well as the remainder. The remainder will also have positive energy. So the next thing that you're going to show is that there cannot be more than one non-zero profile. Okay? Why is that? Well, suppose that there were two. Then if there are two, for each one of the profiles, I have to have that their energy is strictly smaller than EC because in the Pythagorean expansion, all the energies appear. The energy of the data of the U0N U1N is going to EC, tending to EC, and if I have two blocks whose energy is non-zero, I can always subtract one of them and then the other one which remains on the right-hand side will have energy strictly smaller than EC. And I also have the gradient being strictly smaller than the gradient of W because by my variational considerations, if the gradient is smaller and the energy is smaller, the gradient is smaller by a fixed amount. Of course, there's a slight problem with this argument here in that I cannot use the Pythagorean expansion for just the space gradient. But this we overcome by the small fixing of it that I mentioned. So don't get stuck on this too long. But then each profile has energy strictly smaller than EC and gradient strictly smaller than the gradient of W. What does that mean about the profile? By the definition of EC, then the non-linear solution exists globally in scatters. Then I can use my approximation theorem. Approximation theorem tells me that if each profile scatters, the sequence scatters. But that's a contradiction because they're picked to have infinite space-stricken norm. So there can only be one non-zero profile. The next thing is once we have only one non-zero profile, I will show that this remainder, this W's that we know go to zero only in the dispersive norm, have to go to zero in H1 cross L2. The argument for that is the same because if those didn't go to zero in H1 cross L2, I could subtract their infimum and then the one profile that I have would have to scatter and that can't be. So those guys are now going to zero. And now my critical element is nothing more than the lonely profile that got left. So that's how I produce the critical element. Now to show that this critical element, that I have the compactness property, that's the second thing, all I have to show is that I have a sequence of times Tn converging to the final time, I can find scaling parameters and translation parameters such that when I modulate my solution, the corresponding thing converges in H1 cross L2. Okay? That's what I need to do. How do I do that? Well, suppose that this doesn't happen and I produce a sequence of times in which it doesn't happen. Now I look at my critical element at that level of times and I look at its profile decomposition. The profile decomposition again can only have one non-zero profile, the same argument as before, and the remainder has to go to zero. Now if you think about one non-zero profile, I undo the modulation in this non-zero profile and put it on the function and then that's converging and that gives me the compactness. Okay? This is how this works. So you can consider proposition A and B proofs. Okay? So I'll show you now how the actual proof goes. It takes a while, you can see. Okay. So now we come to the rigidity theorem. And this I want to develop in more full detail. So the rigidity theorem says that if I have a compact object, a solution with this compactness property and the energy is smaller than the energy of W and the gradient is smaller than the gradient of W, then the only possibility is that it will be zero. Okay? So this is what we have to do. By the way, as we continue with this, we will see that these solutions with the compactness property are essential in the theory. Say if you want to understand singularity formation for solutions which remain bounded in H1 cross L2, they are the bubbles. One can prove that any such solution bubbles off a compact object. And this is a very widely spread phenomenon. This is a statement that holds for basically any dispersive equation for which you have a profiling composition. So there are the basic bubbling objects. And then eventually you want a kind of rigidity theorem that says that these compact objects then have to be traveling wave solutions. And here what we're doing is we're being below the level of energy of the smallest elliptic solution. So if this philosophy is true, the only possibility is that the compact object will be zero. Okay? So this is a tiny bit of confirmation of this philosophy. Okay? So this puts this in the framework of the larger thing that we're trying to do. Okay? Of course, this was done 10 years ago. So we have to go up to now to be able to say these things. Okay? But this was a beginning towards this. All right. So the first thing that you need to think about, and this is a very subtle thing. You know, when you have these compact solutions with the compactness property, you just assume that there exists a function lambda of t and a function x of t with these certain properties. Now what tells you that these functions are, let's say, measurable? Nothing. You have no knowledge of any property of this function except that they are a function. So the first step is to work a little bit to show that if you have them being some function, you can regularize them to be actually smooth functions before the final time of existence. And to do that, you work a little bit to make them piecewise constant functions, and then you kind of regularize the piecewise constant functions. I don't want to say more than that. Okay? So you can always assume once you have the functions that may be kind of crazy functions, you can always transform them into continuous or regular functions. Okay? I don't know why it keeps... I think it doesn't like me today. Okay. Okay, the next lemma is also a lemma I'm not going to prove, but I'll tell you why this is true. Okay? The lemma tells me that if I have a critical element, I can always manufacture another critical element for which the lambda is strictly positive. Okay? So why is this true? I'll explain it in words and gestures. Okay? Suppose that I'm given one critical element, which is bad, and the lambda goes to zero as I approach the final time. Yes? Sorry, it's too big a question. The lambda bound is from below me. The thing cannot concentrate or cannot concentrate? It cannot concentrate. Or spread, I don't know. You know, it cannot spread. We have this difficulty that sometimes we call it lambda and then others one over lambda. And then, you know, in different papers it's lambda and others one over lambda and we always confuse ourselves. But what I'm saying also applies to one over lambda being bounded from below. So you can always assume one or the other as you may find it convenient, but not both at the same time. But it will just be... Yes. Okay, so what's the proof of this? Suppose this fails. Then you have your critical element and the lambda is going to zero as you approach the final time. Okay? But you have the compactness property and so your solution, after you modulate it, has a limit as you approach the final time. And now you reverse the time from the final time. And then your lambda that was going to zero now is going to rise as you go in the opposite time direction. And that's how it's going to be big. If it was going down as I went this way, when I go this way, it goes up. And that's all there is to it. And all this convergence is worked by the compactness. Okay? So we'll just assume this. And you can see in the notes there's this very careful proof. Okay. Now I'm going to go to...I'm now going to stop waving my hands and do more specific proofs. The first thing is, suppose I have a critical element and the time is finite. So we're in the finite time case. And of course, after scaling, we can assume it's one. The final time. And this lambda not only becomes big, but in fact it goes to infinity as a lower bound by one over one minus t. Okay? And this is a very general property that just has to do with the fact that the compactness property holds and the homogeneity of the problem. If you were working with a Schrodinger instead of wave, you would have square root instead of one minus t. If you were working with KdV, you would have the one-third power and so on. Okay? So let me show the proof of this. So you only need to consider tn going to one. And we look at un of zero to be this object, which is our modulated solutions. Okay? Now we know that the un's, this un's of zero, form a compact set. And if you remember, the corollary of the perturbation theorem was that when I start with a compact set, I get uniform time of existence. Okay? So the solutions corresponding to this data have uniform time of existence. Okay? They exist until a time c0, which is uniform in n. All right? Now this y1 shouldn't be there. It's a typo. So I'm now going to take our critical element and write it in this way so that I can do and tell you what the solution corresponding to this thing is in terms of the solution corresponding to that. So as long as I'm before the final time of existence, we get that the un's modulated in the reciprocal way give me the critical solution. Okay? This is just uniqueness in the Cauchy problem. Because this will be a solution and at time zero it's exactly this and this equals that and the solution with that data will be this. Okay? So it's just a uniqueness. But so the time of existence is bigger than c0, at least c0. I'm sorry. Yeah, it's bigger than c0. So as long as this is smaller than c0, this exists. So this exists. So this must be less than one. Because one is the last time for which this solution exists. So therefore this is less than one, whenever this is less than that. And I plug in t to be the ratio of c0 over lambda t0. And I solve and I get my lower bound. Right? This compactness gives us a uniform time of existence and then you just use how the problem works. So we have a lower bound. The next thing that we're going to prove is that the compactness shows also that if we have finite time of existence, we have the inverted light comb picture. The solution lives there. That is just simply zero. That's what we're going to prove because of the compactness property. If it lives in finite time, it has to concentrate at the point. OK. So how do we prove this? The first thing we're going to use is a property of finite speed of propagation. So we have data which is controlled. And we know that at time zero, the tail is a certain amount small. For all further times, this thing is small. And the way you do it is you truncate your solution to look like the other one at the tail and then it will coincide with it outside by finite speed of propagation. And the one that is like this, you make it completely small by filling it inside the hole. Stupid question. It's from Hardy's inequality. So it's always controlled. Well, to take care of the cutoffs when I differentiate the cutoff. That's all I'm doing. But it's important to note that I have this Hardy term always at my disposal because that's controlled by the h1.norm and it's bigger than or equal to 3 here. OK. This I will be using it constantly. So it's a good thing to keep it in mind. OK. So we always have this can be made small and therefore this can be made small. So now to carry out this proof, the first step. First step is to show that this limit as t goes to 1 is 0. OK. So how do you do that? This is nothing more than the compactness of this modular modulations of this collection of functions together with the fact that the lambda tends to infinity as t tends to 1. We saw that the lambda tends to infinity as t tends to 1 because it's bigger than 1 over 1 minus t. And that goes to infinity as t tends to 1. And therefore what happens when you look at the tail like that, the lambda pushes the tail outside and because of the compactness, the thing goes to 0. OK. The tails are uniformly small for compact objects. So this limit is always 0. Now I have to see what do I do with this thing, the x of t over lambda t. OK. So this is what I have to first control to be able to get the point x bar. OK. So because this expression at time s was small, I can use finite speed of propagation going backwards in time. And I get that this thing is small for any s. Right? I start with something small and I go backwards in time. And then it will have to be small. And the point is that this implies that these guys always have to remain bounded. Because if they don't remain bounded, this thing will go to infinity, let's say for a sequence. But then eventually this will be contained in that. The n goes to 1. This is going to infinity. So outside of infinity I get any ball that I want. And then I let s be 0 here. And I pass the limit in n. And I get that for any ball this is 0. But that can't be because my solution was not 0. Of course it's a critical element so it's space time norm is infinite. So it can't be 0. So that already shows me that x of t over lambda t is bounded. And then for some sequence tending to 1 I have an x bar. So I found the center now. Just by the simple properties of finite speed of propagation. Now once I found the center for n large this is going to minus x bar. And for any eta not fixed for n large is this inclusion holds. For an r not that may depend on eta not. And with this I see by that inclusion that for any s this thing is 0 for any eta not positive when that gives the support property. Level s it has to be contained in the ball radius 1 minus s around x bar. So the picture is really that. In the finite blow up case. The next thing is a fundamental property of critical elements. Now the energy critical wave equation has one more constant of motion. And that's the momentum. That's this fact. For any t this equality holds. And how do you check that while you differentiate in t? You see that it's 0 by the equation. And the next property and this is a crucial property for us is that if you have a critical element and you prepare it properly. You make the x and the lambda continues and either t plus is finite or if it is infinite you make it bounded below. Okay so that's spread out. Then you can prove that the momentum has to be 0. So that means that in a way the compact object is not moving very much. So this is something to be proved. And I think I have enough time to sketch the proof of this. The proof of this is not short. But I'll sketch it. So we will exploit the Lorentz invariance for this. So Lorentz transformations play a role. So assume that momentum is not 0. Then one component of the momentum is not 0. We might as well assume that this is positive. The first component is not 0. If it's negative we change the sign of x1 into minus x1. So we can always assume that it's positive. And let's first consider the t plus. And let's say that t plus is 1 which is without loss of generality. And we re-center the solution so that this x bar is now the origin. The x bar that we found in the previous level. Now it's more convenient here to consider u of xt is 1 plus t and that t equals 0 be the tip of the cone. So let's make it this t equals 0. And now, because it's the first component of the momentum that's not 0, we do the Lorentz transform of our solution in the first coordinate direction. With a parameter L that we're going to choose to be very small. So we have our new solution. And then it's easy to see that this still solves the nonlinear wave equation for time, let's say bigger than minus a half. And that the support is still inside the cone. This is just a simple geometric fact. Now what's the point of this? The point is that when we look at this solution, let's say at time. The minus one half is uniform in L? For L, small. We're only going to look at L very small. So now we're going to look at the derivative of the energy as a function of L as L goes to 0. And the point is that the derivative of the energy is the negative of the momentum. This is a general fact. You do the Lorentz transform, you differentiate that in the Lorentz parameter and you get the negative of the momentum. You can check it by hand. So but now this is negative. And the other thing that happens is that the gradient for some T0 remains small. Now why do we just have to pick some T0? Because we calculated by doing the integration in space and time, which we can undo by the Lorentz transformation. Space-time integrals, you can undo by the Lorentz transformation. And if one was small, the other one is small. And then you can pick a time at which it is small. Because if the integral is small, or the average of the integral is small, there is a time at which it is small. But then the CL has energy smaller than the energy of W, gradient smaller than the gradient of W for L small, and therefore exists globally in scatters. But that contradicts the support, contradicts where it lives. And that's what we gained by the energy being strictly, you see, the energy falls from the energy of UC, becomes less than the critical level of energy. So if the momentum is non-zero, then you can decrease the energy by doing a Lorentz transformation. And therefore you reach a contradiction. So the only thing that could have happened is that momentum is zero. So it's a property of critical elements. Now in the infinite-time case, the calculation is a bit more complicated, but the principle is the same. So I'll skip the infinite-time case. But you see that we're building properties of these critical elements so that when we improve the rigidity theorem, we have more things at our disposal. That's the story. Okay, so I think for today we can stop here and then continue on Friday. Thank you. Thank you.
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The theory of nonlinear dispersive equations has seen a tremendous development in the last 35 years. The initial works studied the behavior of special solutions such as traveling waves and solitons. Then, there was a systematic study of the well-posedness theory (in the sense of Hadamard) using extensively tools from harmonic analysis. This yielded many optimal results on the short-time well-posedness and small data global well-posedness of many classical problems. The last 25 years have seen a lot of interest in the study, for nonlinear dispersive equations, of the long-time behavior of solutions, for large data. Issues like blow-up, global existence, scattering and long-time asymptotic behavior have come to the forefront, especially in critical problems. In these lectures we will concentrate on the energy critical nonlinear wave equation, in the focusing case. The dynamics in the defocusing case were studied extensively in the period 1990-2000, culminating in the result that all large data in the energy space yield global solutions which scatter. The focusing case is very different since one can have finite time blow-up, even for solutions which remain bounded in the energy norm, and solutions which exist and remain bounded in the energy norm for all time, but do not scatter, for instance traveling wave solutions, and other fascinating nonlinear phenomena. In these lectures I will explain the progress in the last 10 years, in the program of obtaining a complete understanding of the dynamics of solutions which remain bounded in the energy space. This has recently led to a proof of soliton resolution, in the non-radial case, along a well-chosen sequence of times. This will be one of the highlights of the lectures. It is hoped that the results obtained for this equation will be a model for what to strive for in the study of other critical nonlinear dispersive equations.
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10.5446/20479 (DOI)
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So the last time we showed how to extract the scattering profile in the infinite time case. And now today and next time we will sketch the proof of the decomposition in the finite time blow up case. So we have a solution that blows up at time 1, let's say, that remains bounded in H1 cross L2 up to time 1. And we want to now produce a decomposition into solitons. Okay? So that's the task. So in the notes, so there's a first step in which we prove the decomposition with a weaker error than what we'd like. And then we will go through several stages to improve the error. Okay? And in order to improve the error, sometimes we will have to slightly tune the sequence of times. And at some point we don't tune the sequence of times anymore, but then we show better and better properties of the error. Okay? Now the first step is inspired by work on wave maps. This goes back to work on relakis on wave maps. And it's what we call a Morowitz estimate or a Morowitz identity. The fact that there's a way to use ideas from wave maps for the energy critical wave equation, goes back to work that we did with a caught lorry and a slug. So this is the approach that's presented in the notes. But today I'm going to present a different approach, which I think is more concise conceptually. And it allows, I think, hopefully, for Morowitz as we move along. Okay? So because of that, we'll use the blackboard for the beginning. And then in the notes is the other proof, so you will be able to read that. Okay? So... Define it a blow-up case. We can always make it to be one by scaling. So that's not the problem. So we're going to approve the following claim. And we call this the crucial Morowitz estimate. Although in the new form in which we're going to do it, you do not recognize this as coming from a Morowitz identity. And in fact, I think you can recover the usual Morowitz identities, even in the wave map case from this point of view. Okay? So the claim is that we assume T plus equals to 1, and that the origin is a singular point. So it's a point where even locally I cannot continue the solution anymore. Okay? We introduced this notion earlier. So what it means is that it is not a regular point, and a regular point is a point where if you take integrals over small balls around that point, you get that to be uniformly small for all times up to one. Those are the regular points, and this is a singular point, so it's a point where there's concentration. That's what that means. And let me assume that it's spaced by one from all the other singular points. Since there are finitely many, I can always pretend that. Okay? This is just so as not to have to write more. It's not important. Okay? Then, just a constant C such that 4, 0 less than T up to one. No, maybe not. Let's say a half. So this a half is symbolic, and it depends on the fact that the other singular points are at distance further than one. Otherwise, you have to go sufficiently close to one. Okay? So we have an estimate, and the estimate is that the integral from T to one of the integral of x less than one minus T of the following expression. So we get a logarithmic estimate, but what's crucial here is that, well, first of all, this integral is finite. That's already very good. What is interesting here is that the power there is less than one. Okay? So the original proof had the power three quarters. We can get the power one half using this approach. Okay? Now, why is the power one half interesting instead of why is the power less than one interesting? It's because the finiteness of this, suppose that this was just bounded, this inner integral. Then, of course, the integral up to one minus T would behave like the logarithm of one over one minus T to the power one. But somehow we're only getting the power one half, so that means that in some sense the inner integral is vanishing with the rate as you go to T equal to one. Okay? And the power two is dimension dependent. Okay? So the number is different in dimension three, and this has to do with the scaling of the equation. That's exactly what it is. Now, in wave maps, there is no, this factor doesn't appear, and that's because there's no factor in front when you rescale wave maps. Okay? And so that's how this thing is working. Now, the proof of this that I'm going to show now is a very, from my point of view, is a very satisfying one. Because it uses the ideas that we already seen that come from the work of Merlin and myself, where we showed that there cannot be a compact solution which has self-similar scaling. Okay? And if you recall the proof of that, which was given, I don't know, a month ago or something like that, it used the introduction of self-similar coordinate. Okay? And then some integration by parts. Now, the reason one could do that in the compact situation was that the boundary values on this inverted cone, let me put the inverted cone here. The boundary values of a compact solution are forced to be zero. And therefore, we had some boundary terms that disappeared because that was zero. Now, in this case, we can no longer assume that the thing is zero, so we have to somehow handle these boundary terms. And these boundary terms are huge. Okay? So we will see. So I'm going to prove the claim. So the first step is what we call the energy flux estimate. And as I recall, we have this solution that blows up at t equal to one. So this is t plus equal to one. We recall that there is a v of t, which is a regular solution at t equal to one. So this is not one that blows up, but it's one that moves continuously up to t plus equal to one. So the property that this support of u of t minus v of t is contained in the inverted cone. Okay? So that outside the inverted cone, our solution looks like a regular solution. We saw that this was a consequence of finite speed of propagation, basically. So what you do is you consider the weak limit as you tend to one, and you now solve the nonlinear wave equation with that initial data at time one. And that's the v. Okay? So we have the object. Now, since v is a regular solution, we have two facts. Of course, the norm, let me just put it like that. So the v arrow and u arrow notation means the pair u, d, d, t, u and v, d, d, t, v. Okay? It's just a shorthand. So this is a finite, but moreover, the spacetime norm, the Strikatz norm, is finite. Because this is a regular solution, so by the finite blow-up criterion, that norm is finite, because it doesn't blow up. Okay? Is this okay? Okay, so then... In the last one, x is in the cone of everywhere? No, x is everywhere, because this is a regular solution. Okay? So this is what this local well-posedness theory gives you. Okay? So the next remark I'm going to do about the v is that as a consequence of these two properties... This is a very remarkable fact, but it's trivial, right? From the two other properties and the Leibniz-Roller-Samm. Right? v to the sixth, you take d, d, d, t, you get v to the fifth times d, d, t. You do the norm in x, you do Cauchy-Schwarz, you get the l10 times the l2, and then the other one is in l1, and the other one is in l infinity. So this matches. Okay? But now, this implies that v to the sixth belongs to l1 in t and x in the boundary of the cone, d sigma. That's a standard trace theorem. Right? If you have the t derivative in l1, you don't need to even invoke a theorem, you just use the fundamental theorem. Okay? But on the boundary of the cone, v to the sixth equals u to the sixth by this support. Okay? So therefore, now we've proven that u to the sixth belongs to l1. And this is huge. This tells us a lot, because now we combine this with the flux. So I'll write down the flux. So, well, maybe I'll write this explicitly here. Okay? This is the same. I'm just writing this in coordinates. So now I'm going to write the energy flux. The energy flux is the following identity. So let's take t1 and t2 less than 1. Okay? So the energy flux is fundamental in the study of wave equations. And this is a well-known identity. Okay? So, let's take t1 and t2. Okay? This is the standard flux identity. And you prove this by calculating d dt of the density of the energy and then using the fundamental theorem and the divergence theorem. Okay? There's nothing more than that. Now, one of the big difficulties in the focusing wave equation comes from the fact that this object in here is not non-negative. It can possibly change sign. And this is what causes a lot of the difficulties that we see. But this observation tells you that you can control the negative part. And that's the key thing. We can control the negative part because it's exactly on the boundary of the cone where your blow-up solution equals a regular solution. Okay? So the corollary of this is that... Oops. Oops. Why? Why is this true? Well, we use this identity by the fact that the h1 cross l2 norm is bounded. This term is bounded. This term is bounded. By the previous thing, the l6 term is bounded. So what I have is bounded. Okay? I'm just worried that there is a square here and not in the first line. Square where? Inside the bracket here. Inside the first line. It's because... Yeah, this here shouldn't be there. You're squared because you're worried because I made a typo. Okay? Okay? And clearly this thing is non-negative. Because this is the half here. Okay? Just by Cauchy Schwartz. Okay? Or completing the square. Whatever you... Okay, and another way of writing this, which will sometimes be used, is that... And I need to... I'll introduce some notation. I'll read this. Where, by definition... What did I write? Yeah. This is the tangential part of the gradient. This is the definition of that quantity. Okay? And the reason why this follows from that is that if you just expand this square, you get what's on top. Okay? So it's telling you some control on the boundary of these objects. Now I will need one other term, which is a Hardy term here. So I will add this to the corollary. This is also bounded. Okay? Now this needs a proof. Right? You can't just... But you'll see things work very neatly here, because... Let me define f... to be this function. This is a function only of x. I'm going to use Hardy on this function of x. Okay? So let's calculate the gradient of this function of x. I'll call it like that. This holds just by the chain rule. Okay? So you see that exactly the gradient of this f is the flux. And since the flux is in L2, this gradient is in L2. And now I can use Hardy. And on the boundary of the cone, 1 minus t equals x. Okay? Okay, so now we got the three things that we want. Okay. So did I call this step 1? Yes, you did. I did? Oh. Well, now I'm going to go to step 1 prime. Step 1 prime introduces self-similar coordinates. Okay? Which we did already when we studied compact solutions in the grand state conjecture. Okay? So this will be the same. Now suppose that x is less than 1 minus t. I was in between these two sets of lectures. I was giving another set of lectures where there was a blackboard with a hole. And I lost the eraser. It went down the hole. The whole thing grounded to a hole. Okay? Good. So inside the cone, y is x over 1 minus t. So that y is less than 1. And s is minus the log of 1 minus t. So our new universe now is the s, y variables. This is, as I mentioned in previous lectures, this is the analog of the parabolic self-similar variables that were introduced by Giga and Kohn. Okay? And that's what we use here. So now we define w of ys to be 1 minus t to the 1 half u of x t. This was just like we did earlier. And this 1 half power of 1 minus t is responsible for the coefficient 1 half in front of the u. Okay? That's where that comes from. In that estimate. Okay? We'll get to that. I mean this is just information. It's not something that's supposed to be obvious. Okay? Okay. So now we introduce some weights. And this weight obviously blows up at y equals to 1, which corresponds to the boundary of the cone. And that's why when we were dealing with compact objects, we needed to have things that vanished on the boundary of the cone. Okay? So now all we're going to do is regularize this weight. And we will work with this weight instead and then choose epsilon appropriately. So now we have s goes from 0 to infinity now by this change of variables. Okay? When t goes between 0 and 1, s goes from 0 to infinity. And y is less than 1 because we're looking inside the cone. Okay? And now I write the equation for w, which we have already seen. The equation is the same as before. Let's just do it like that. Okay? So this is the equation that W verifies. So it is a wave equation, but it has nonlinear wave equation that you cannot avoid. But it has some interesting features. First, the elliptic part degenerates as y goes to 1. So it degenerates the elliptic equation. And the second thing is that there's this extra term here. What I didn't do is copy this properly. There's a gradient and a dds. So it's a second order derivative. And that's a kind of parabolic type term. That's why this becomes a little bit parabolic in some similar coordinates. Okay? Anyway, so this is the equation. And now I'm just going to tell you two more things. This we can compute in terms of u. So the s derivative of w. With light? Oh, I'm sorry. Should I lower this? Yeah, absolutely. Okay. Oh, maybe we need light there. It's okay now? Okay. No, it should be okay now. Okay, so if we look at this expression here, you see that it corresponds exactly to what I have inside my integral. I just have to divide by the power 1 minus t to the 3 halves. Okay? And so that's the point that this expression inside is the self-similar time derivative. Okay? You first move this for rho x and then take it in. I haven't done anything yet. I haven't done anything yet. This is just the formula. There's no epsilon in this formula. It happens so very often. Right. And this equation has the rho. It doesn't have the rho epsilon. Okay? Which is singular at y equals to 1. And I'll tell you when the rho epsilon comes. And then I put the gradient in y. This one is much simpler. Right? Okay. So from these two formulas, we get that the h1 norm is bounded. Okay? Because that's just the change in measure. We know what ddy is. We know what ddy is. It just gives you the right factor. This just comes from the fact that each one of these objects, once you weight it appropriately, is in alto. And for you, you have to use the regular Hardy inequality in x. Okay? Now I tell you what the flux estimate gives me, together with this estimate. Okay? The flux estimate, together with this estimate, gives me that the integral from 0 to infinity, integral of y equals to 1, of dsw of ys squared, ds in y, ds is a sum constant. Okay? And I'm going to use that because, well, dds has these terms in it. And this one, once you change the variables, corresponds exactly to the flux term. Corresponds to the first term there. And this one corresponds to this term. So it's just a change of variables. Okay? So you say the boundary values may be bad, but there's something good about them. The s derivative can be integrated. And finally, my claim boils down to the following. And this is just the change of variables, and the formula for dds. You just have to change variables in the y, and in the s. See, the dds change of variables produces the factor of 1 over 1 minus theta, because s is the log. Okay? So this is all fit. It's all fitting perfectly. So now, how do I prove the estimate? And now, maybe, can people see here? Okay. So now what we do is we introduce an energy. So this is step two. This is proof of play. So I define e epsilon of s. So this is an energy which now depends on epsilon. Okay? So that's my definition. So it's a definition. Now this is the natural, if I instead of having rho epsilon, I had rho, this would be the natural energy associated to this equation. If you multiply by dW dS and integrate by parts, and assume that all the boundary terms are zero, you would get exactly this. You have to do dSW times rho. Multiply and integrate by parts. Which is what you always do for the wave equation. That's how you deduce the energy. Okay? If you do that, you get the energy for epsilon, and all the boundary terms disappear, you get the energy for epsilon equal to zero. Okay? Now unfortunately, the boundary terms don't disappear for us, because nothing is zero. And second, we don't know that when epsilon is zero, this expression is finite. Because it's singular, y equals to one, and why should it be finite? That's the energy from the first line of the equation. No, do the second one. These two terms combined, do they... Yes, it includes everything. So you have to be a little patient when calculating. But everything cancels out, and it gives you that. Okay? All right. But for us, this rho is too singular, because we don't have zero on the boundary. In the case when we were working with compact objects, they were zero on the boundary, and we could use the E0 energy. And that's what we did in our paper. So now, okay, so you put the Epsilon. So the interesting thing is the time derivative, the S derivative of Epsilon. Right? That's what you need to look at. And now the amazing thing is that there's a clean formula. So this is the very nice thing that happens here. Okay. Okay, so this is the formula. And I guess we were very surprised when you could actually calculate it. And it's very compact, right? I mean, it's... So let's look a little... Okay, so how do you prove this first? You do the same as you would do trying to show that the energy for the wave equation is constant in time. You multiply the equation by W times rho Epsilon, but WS, I mean, the S derivative of W times rho Epsilon, and you integrate by parts. Yeah, a square in Epsilon in the second term. No, it's a power one. It's too strange because it's essentially the same for... Epsilon is positive, you know. And then some of the signs will change. But it is a power one, because if you look at... Epsilon is the same for... Epsilon is negative or positive, right? Yes. Oh, so I see what you're saying. Let me think about it. Is it... But it would be absolute value, Epsilon. What you get is an Epsilon squared square root. Okay? No, it is Epsilon. It is not. The reason that it is Epsilon is what happens with this when you go to Y equal to 1. Okay? It's exactly Epsilon squared square root. Okay? So the way you prove this is you multiply by d dSW times rho Epsilon, and you integrate by parts. Okay? And of course, if you're going to do it at home, take your time, because you will... Most of the times you will get it wrong, and then you will... I know my experience, okay? But this is the formula. Okay, so now let's understand this formula a little bit. Okay? What we want... So first, let's assume that W was zero on the boundary. Okay? Like the old case. When W is zero on the boundary, d dSW is also zero, because it's a cylinder. So this term would disappear. Okay? This term, you make Epsilon equal to zero goes to zero. This term disappears. And in this term, you get 1 plus Epsilon squared, so you get 1. So when we integrate, if the Epsilon is... if the energy is bounded, you get the integral of this thing, and the integral of this thing is exactly what you're trying to control. Okay? So this is the right kind of thing. We want to integrate, and the best thing to integrate is the derivative, because by the fundamental theorem you can integrate. Okay? In our case... What? No. In our case, when we integrate in S, this term is the one we already know from the flux. The integral of this term is convergent by the flux. So that somehow would save you here. You have the flux, and therefore I think I wrote it here. Yeah. The integral is convergent. That was the fluxest. Of course, I'm not going to make Epsilon zero. If I make Epsilon zero, I die. Okay? I'm sorry. This is something obvious. So you said if you pretend to take Epsilon zero, we're left with the first term, and then we're integrating. And if E is bounded... What happens with Y, even? Why it got integrated? There's no... Right, it's just an energy, and then we integrate it. And then by this magical identity, you control this integral, because this is... I'm sorry. Because this is a positive quantity, which is what you really want to control. Okay? So that's how this magic works. So now what do we do when Epsilon is not... when we don't have the boundary terms? Okay. So the first observation... I'm going to use all the blackboards, and then move on back to the transparencies. The first observation is that... Epsilon, the energy is bounded by one over Epsilon. Why? Because I'll just... I'll write it for you. There's only one remark. Okay. Because of this. Right, in the definition, this is row Epsilon, and the rest is covered by... Where do I have that? This fact. Okay, and hardly. Okay? And this term, when I integrate it, is bounded. So if I do an integral here, the integral of this is going to be the Epsilon at the two endpoints, which is one over Epsilon. This is a constant times the one over Epsilon. And then I have these two terms. This is the one I like, and this one is a horrible term. But it has the redeeming feature that there's an Epsilon squared in it. Right? There's an Epsilon squared, and it's mixed. It has a gradient and the DDS. Okay, so now we're going to just use Cauchy-Schwarz. Okay, so we will integrate between S1 and S2, and use the fundamental theorem. Okay? Then, 1 plus Epsilon squared, integral between S1 and S2, integral of y less than 1, dSw squared, 1 plus Epsilon squared minus y squared to the 3 halves, will be less than or equal to C over Epsilon that comes from this term and this term. And then plus... That. Okay? So now I'm going to do Cauchy-Schwarz keeping this weight. Okay? But the Epsilon squared I will keep with this term, which is the one I don't like. And the other one I leave alone. And then I put a small constant in front of this one that I absorb by the left. And what I'm left with is the following. C over Epsilon plus... Now here I will get an Epsilon to the fourth when I square. And in the denominator I have a 1 over Epsilon cubed. Right? So I get an Epsilon to the... a 1 over... an Epsilon. Then I have the length of the integral because I'm not using anything on that. I'm just doing it in y. And that's it. And maybe instead of 1 here, I have 1 over 8 after I hit that one term. Okay? I just did Cauchy Schwarz. I kept these two things together... again that's even more squeeze. And then this video we can do if you want to. So that's it for Cauchy Schwarz. Alright so that is it. And if you want to make two little estimations I kept these two things together. Pardon me? The last constant C is now missing, you got one A there. It comes from the Cauchy Schwartz. The Cauchy is what you need, one A. What's S? Why do you need one S? You need a constant, right? Oh, you lose a little bit. It's just a symbol for something smaller than one. Okay? I don't care what constant I have as far as a universal constant. So all I'm trying to say here is that I lose a little bit in the constant here and I increase a little bit in the constant there. What information do you have on the Y dot? The Y is less than one, so I can throw out the Y. And the gradient is in L2. Okay? So it's not an infinity problem. Okay? So the Y doesn't hurt me. What hurts me is that I can't integrate in S. But now I'm gonna... So once I have this bound, the first thing I say, okay, I'm gonna throw away this thing. After all, it's bigger than one. Right? It's only bad. I mean, it only grows. If I bound it from below, I can throw it away. Okay? Okay? You make the two terms equal. And that's the proof. Okay? Okay? So is this okay? So you just have to have faith. Because after all, the computations are not difficult. But you have to think that it will work. Right? I mean... But the key point that we realized later was the fact that the DDS of this W has this direct relationship with the Morowitz thing. Okay? This has to do with the scaling of the equation. All right? And this does work also for wave maps. I mean, this kind of argument gives you control of the Morowitz type estimate in wave maps. Okay? Which, you know, are in the work of the servants and the Tau and Tau, they're very important. Okay? And this gives another way of looking at that, too. Okay? All these computations have nothing to do with criticality. You could have it for... with criticality. No, yes, no. It's the scaling playing against the criticality. I mean, otherwise you get other... you get other numbers. Then the thing that is a little bit... The only thing that you have from... is the W5 in the equation, no? No, but it's also the... what is the expression that appears here? You see, because this will always appear... So, what I will say, though, is that you are right to a point. This can be used in subcritical cases, too. That, in fact, Zag and Merle used this in some subcritical cases. Now, what it buys you is unclear. Anyway, I think this is a new perspective on this kind of argument. Okay, and if you look at the paper, I will flash the slides now. Okay, one thing we're going to do next. The reason I used T plus equal to 1 here is because the calculations were done in my paper with Merle at T plus equal to 1. But going on, it's more convenient to, instead of using... Instead of using... Instead of using this picture to use this picture, but this being the blow-up point. Okay, it's just a little bit more convenient. And the effect it has is that this minus here becomes a plus, because you're pointing in the opposite direction. Okay, other than that, it's all the same. But I didn't want to redo all the calculations, so I just borrowed that, okay? Okay, so this is what I'm saying here. And I'm reminding you of the singular set and the weak limit. But now the blow-up point is T equals 0. Okay? So the picture is that one. Okay? So the estimate now had the power 3 fourths. We got it now with the power of 1 half, but they are equally good for what I'm going to do next. But 1 half is better than 3 fourths, because it's smaller. And hopefully there's further improvements. And the only thing different now is instead of 1 minus T, you have T, and that's the point of using that picture. T is nicer than 1 minus T. And the sign is the opposite. Okay? So I'll go through the proof here, which... Okay. It wasn't complete. But it's a very lengthy thing, and you don't really see clearly where things are coming from. I think this calculation is quite illuminating. Okay? So now let's move on. So now we have to improve things. So that's the process is that, okay, you get something. And the reason this is a very nice estimate is... Okay, I'm saying this again here, is because this thing grows slower now in average. Then this log, and so it has to vanish at some rate on average. Okay? And so one can think of this as a Tauberian argument. Okay? So this is telling something about the Cesare sums, and we want something about the object itself. So that's where we need to pass to a subsequence. The classical Tauberian argument says that if you have Cesare sum-ability, for a subsequence you have convergence. Okay? And this is the reason why we now need to pass to a subsequence. Okay? So it's actually a very classical thing, and it's very easy to trace. Okay? So let's move on then. So now we're going to do the actual Tauberian argument in this context. Okay? And of course we're going to use a bit of modern technology to do that. We're not going to follow the original things. We're going to use the Hardly-Little with Maximal function, for example. That actually comes in very handy here. Okay? So now there's some real variable type of arguments. The next lemma tells me that I can find the sequence... Remember the time is now going to zero instead of to one. Okay? So now I can find a sequence of times, and I'm going to get two different sequences of times. And if you recall in the proof of the extraction of the scattering profile, we had two times, two sequences of times. One was Tn, and the other one was Tn minus alpha over 10. Because we needed to do some integration, and we needed to control both endpoints in the integration. And the reason for this is similar here. Okay? And what we will do is first produce these objects, such that the averages are actually going to zero. And not only that, but something enhanced, where you can also integrate a little bit bigger in T, still take the average, and a little bit bigger in X, still take the average, and those goes to zero. And we want to choose these guys so that they are actually separated. You think of an interval, and you're choosing... you split it into three parts, and one of them is one extreme part, and the other one is the other extreme part. So this is a very standard thing that you do in this kind of problem. Okay? Except the numerology, I don't know. Don't pay too much attention about the fractions. It's the point of the thirds of the interval. Okay? So there's a separation between them, and they're of the same size. Okay? So we're going to produce a sequence, two sequences with these two properties. Okay? Why is it important that they're the same size? Because you need that there are differences of the size of each one. The difference is the length of the interval. You need that the length of the interval be. Okay? Okay, so how do we do this? Okay. So now we're going to use this Morowitz estimate first. So we pick a big capital J, and we look at T1 equal to 4 to the minus J, and T2 equals 2 to the minus J. Okay? We will apply it in that case. So then T2 over T1, long, gives me J to the three-fourths. We could get J to the one-half, but we don't care at this point. Okay? And then I'm splitting it into the intervals. So this is just a splitting of the interval between 4 to the minus J and 2 to the minus J, into equal size intervals. Now, since the sum is smaller than this, by pigeonhole, there's one that's smaller than the minus one-quarter, which is one minus three-quarters, because there's J over them. Okay? So this is just a pigeonhole argument. If all of them are bigger than this, I have J of them. I have bigger than J times J to the minus a quarter, and that's J to the three-quarters, but it is smaller, so... So one of them is big. One of them is small. If they are all big, I get a contradiction. Okay? So there's one little J like that. And now I look at the sequence made of the 2 to the J's and 4 to the minus J's, where these are the chosen mu J's, and I choose a decreasing subsequence. Okay? This is a sequence that's going to zero, and so... Yeah, 3-4 is because you are using the estimate with the log of 3-4. Right. That's exactly... Otherwise it's one-half now. Right. Okay? Yeah. Yeah. And this is precisely the way that you use such an estimate, where instead of having... If you had J here, you couldn't do this. There's no way to get it. Okay? So this is what we do. We get to the J to the minus a fourth, and then we can make this a... decreasing, and we get... that this will tend to zero. All right? So now we did the first part. Now I want to call G of t, this function of t, which is the thing that I control by the Morowitz estimate, and which I just gave better control. And now I know that this average is of G of t, 10 to 0. That's how I chose the mu Js. So since they tend to zero after passing to a subsequence and relaveling the indices, I can assume that they are 4 to the minus J. Okay? Just a simple argument. And now I look at the hard little maximal function of G times chi of mu J up to 2 mu J. Okay? So that's a function. And now I'm going to use the weak type 1, 1 inequality. So the measure of the set of t in mu J and 2 mu J, where the maximal function is bigger than 2 to the minus J, is less than or equal to 2 to the J times 4 to the minus J times mu J, which is the one norm. So that's why I have 4 here and 2 here and I'm left with a 2. Okay? So this is just the weak type 1, 1 inequality. So what this tells me is that the set where it's big is getting very, very small. So there are a lot of t's in which it is small. And that's how I choose my t''s. Okay? And I have a lot of room because I have a very small fraction of the total. Okay? And so that's why we can choose them like that. And now the G, remember, was integrated only up to t. Why can I go to c times t? Because between t and c times t, u equals v. And v is a regular solution and everything is going to zero for the regular solution. And the maximal function is exactly what you need to control these things. This is exactly the maximal function. It's just the definition of the maximal function. Okay? So let's... So now we have our two sequences of times. We will first use just each one of them and then we will put them together. Okay? So the first step is to use each one of them. And we will get a decomposition for one and a decomposition for the other. Then we will use those two decompositions to get some improved estimates and then we will find a new sequence of times. Okay? So you have to be doing things gradually. You can't get everything at once. Okay, I'm sorry. So now we can give a preliminary decomposition. And suppose we have a sequence Tn such that this condition star holds. Then we can have a preliminary decomposition. So we have a J0, scales, centers, strictly less than Tn. Lorentz parameters which are less than one, traveling waves, such that U is the regular part plus the modulated solitons plus an error. But in what sense is this an error? It's only an error in the sense that it sells six normals to zero. Okay? Remember I want the H1 cross L2 normals to zero. But first I'm going to just get the n6 norm going to zero. Okay? So this is the first step. Okay, so I'll explain how you do this. The n6 norm is only for epsilon 0, not epsilon 1. Right. And epsilon 1 is not in n6. But epsilon 0 is. Okay? Can you prove this more in the strictly norm for free or not? No. We have to work very hard for the strictly norm. We'll get that at the very end. Which is even less than H. Yes. So what we will do, well, you will see. But this comes at the end. Well, no, at the step before the last one. And then from the strictest norm, you have to go to the actual energy. Okay? But you will see, this we'll see next time. That's a lot of extra things are needed for that. Let's see, let's go with this for now. Let's try to see this. I mean, this is the starting point. Okay, so how do we prove this? We're going to use an inequality star. Remember this. More always type inequality, but where now we chose the intervals well. So the first point is we pick a cutoff function phi, which is 1 on B3 and support it on B4. And now I'm going to look at u0 and u1 and which is u times phi of X over Tn. Okay, so I truncate my u at time Tn. The Tn is the sequence of times for which I have this enhanced Moranowitz estimate. Okay. Now I claim that it's enough to prove the decomposition for this sequence. Why is that? Because the difference, this thing equals u minus v plus an error that goes to zero. Why is that? Okay, so let's start. There basically are two cases. Suppose that we look at X bigger than Tn. Okay? If X is bigger than Tn, u of Tn and v of Tn are equal. So this part is zero. What happens with this guy? If X is bigger than Tn, u is v. So v is a regular solution. And so for a regular solution, since I'm truncating up to a small size T7, it goes to zero. Okay, so that's the part where X is bigger than Tn. How about the part where X is smaller than Tn? When X is smaller than Tn, this guy is equal to u because of the choice of phi. So all I'm left here is v. But v is regular and it's in the region where X is smaller than Tn, so everything goes to zero. So that's how you prove this statement. Okay? So that tells me that all I have to do is handle this term. Okay? What was for zero? R0 is the amount where you don't meet any other singular point. Okay, you can think of it as one if you want. So that they don't interfere with each other. Okay? Okay, so now we go on. So I'm sorry, but we have to use the profile decomposition at this point. So what we do is we do a profile decomposition. We decompose our sequence into these blocks. And they are linear blocks. Plus an error which tends to zero in the dispersive sense. Okay? So far so good. And I'm going to divide the T's, Tj's. I assume that they're either identically zero or the limit goes to plus or minus infinity. Okay? I always can do that. And I have the, of course, the pseudo-orthogonality conditions. The first observation is that u0n, u1n goes to zero outside x bigger than Tn. Why is that? Because it's u cut off more or less at Tn. And outside Tn, u is v. So this is really v. And since I have the cutoff on v, the cutoff's up to 3Tn, then this is small. So this is true. So since the u0n's and since the use of n01 are localized in x less than or equal to Tn, that gives me some control of the parameters in the profiling composition. Okay? So this goes back to Bajoury and Gerard. You just have to take my word for this. So what you get for free from this Bajoury-Gerard, the accent got put in the wrong place. Never mind. It was not a French-speaking typist. Okay. So what you get is immediately from this, from the localization property, you get that all the scaling parameters are controlled by constant times T sub n. And the translation parameters are controlled by T sub n because away from T sub n, nothing is happening. The thing is just zero. So everything is controlled like that. And the other thing that you get, and this is kind of handy, I mean it's not too terribly important, but it is handy here, is that this limit is non-zero for at most one index J. There can be only one where the lambda Jn equals T sub n. T sub n is what localizes this sequence. Okay? And we will call it, pardon me? I'm sorry. There's only one for which this is not zero. Okay? So there's only one for which the scaling is self-similar. Okay? That's what this means. And for that one, if it existed, we could change the profile again to make them equal by rescaling the profile. And now by extraction, this sequence is bounded, right? Because of this property. So the limit will always exist. I'm not saying now that it's less than one yet. It's bounded. So I can assume by extraction that all these limits exist. Okay? Now we will divide the profiles into three cases. The first one is suppose that there is a Tj0, that there is a j0 for which these two things are equal. Okay? What we will do is in this case, the associated nonlinear profile is actually exactly self-similar and with compact support. And because of the theorem that Merrill and I proved, those things cannot exist. So there can be no self-similar profile. That's the first case. I will explain how you prove this. Okay? I'm just trying to show you the big structure of the proof. The second case is still the Tjn is 0. But the lambda j is much smaller than Tn. Remember, the j is always bounded by a constant times T7. Okay? So they're either comparable or lambda j is much smaller. And the last case is when Tjn is not 0, but when it is not 0, it means that Tjn over lambda jn goes to infinity. Right? Because we said that we could change the Tjn's to be either 0 or going to infinity. Okay? We will see that the profiles from case 3 can be put into the error. They automatically have a small l6 norm. Okay? I will explain that in a second. So we will not need to take care of these profiles. But in this case, in case 2, we will show that the lj's are all less than 1, and that the profile is actually a traveling wave. And once we have this, the decomposition forms. All right? Okay. So once this is done, the result follows. For case 3, the point is that for any linear solution, the l6 norm goes to, in the energy space, the l6 norm goes to 0, as T goes to infinity. And if minus Tjn over lambda jn goes to infinity, that's where the profile, the linear profile is evaluated. So each one goes to 0, but we can combine them because we have a Pythagorean expansion for the l6 norm to the 6. Right? And this is the proof that the l6 norm goes to 0. It uses finite speed of propagation. This proof. There are other proofs. This proof just uses finite speed of propagation and the dispersive ester. Okay? So because of these things, the third case can be moved into the error term. So we just have to understand the first two cases. Now the other point is that in the second case, the case where we have the Qs, there can only be finitely many, and the number that you can have depends only on the h1 cross l2 norm. Because if you recall, for all nonlinear elliptic solutions, the gradient has a lower bound. The lower bound is the lower bound of W. So if you had too many of them by the Pythagorean expansion, you would violate the boundedness of the h1 cross l2 norm. So that always gives you an upper bound on how many of the Qs you can have. Okay? Alright. So now I'm going to try to explain why. In the first case, we have the sub-similar case, which is not possible. And in the second case, we get the solitary wave. Okay? For case one. So we're in case one, so that means that lambda j0n equals T sub n. Alright? And Tj0n is zero. Now in this case, it's not hard to show that the Cjn0, since they're going to zero, you can take them all equal to zero by changing the profile. And that the linear profile, and hence the nonlinear profile, have compact support. Okay? Of size one. So after using properties, the standard properties of the profile decomposition and the approximation theorem, you can see that the Moroan's estimate gets inherited by this nonlinear profile. Okay? And what we get is the T derivative, the x over T plus one derivative, the u over two, dt. And this now has to be identically zero, because you make the n parameter go. And the scaling gives you this. And this is true not everywhere, but on a sufficiently big region. So now we get that this thing is identically zero. Now this is a first-order equation. You can integrate it by characteristics. Okay? And so now you can say what this means. So we have this first-order equation, and there's only one kind of solution. This is the formula for the solution, for some functions, Psi. And since uj zero was compactly supported, Psi is compactly supported. Now we also know that uj zero is a solution of a nonlinear wave equation. So this, since it equals it, is a solution of a nonlinear wave equation. So this is a self-similar solution to the nonlinear wave equation with compact support. The theorem of Merlin and I shows that it's zero. Okay? So this profiles couldn't have appeared, because they lead to a contradiction. Okay? Now let's look at the other profiles. Case two. And let's say that the one we're looking at is the first one. T1n is identically zero, lambda1n is much, much smaller than Tn, and L1 is this limit. Now because of the fact that the lambda1n is so much smaller than the Tn, this term does not contribute. When you plug it in, that will go to zero by the scaling. And then you can prove that x over T, see where L1 goes, goes to C1 over Tn. The profile is concentrating around C1 over Tn. So x over T becomes L1. So in the limit, in this nonlinear profile decomposition, you get that this guy verifies that this is zero. So that means that now the first order equation is this first order equation. So that means that it's a traveling wave. And it's a traveling wave solution, and we have proved with the Kyren Merle that traveling wave solutions are exactly solutions of the elliptic equations. Lorentz transformed according to this direction. So that already, you have to use that theorem to show that L1 has to be less than one. What we showed is that if you have a traveling wave, the speed has to be strictly less than one, and here is a solution of the elliptic equation, Lorentz transformed. So that's how we get that this guy is the traveling wave. And so this now just gives the decomposition in this preliminary form. Okay? But it gives it for the two sequences of times that we constructed, because it gives it for any sequence of times for which this average goes to zero, this Morowitz type average. And the reason we want these averages instead of for each T is that in this computation of these limits, you want to take weak limits. And so you need to use compactness. And if you go to two variables, L2-Loke is compact if you're contained in H1 in space-time. And that's the reason why you need to pass to the averages. Okay? To be able to use that local weak convergence gives strong convergence locally. But that, okay, that works. In fact, this is something that we had used with duke Aére and Merle in our first paper in the radial case. This trick. Passing to two variables instead of one. Okay. Now we're going to improve the bounds on the errors using virial identities. Okay? And we have to switch the sequence of times. Okay? So how do you do this? So the claim is now there is another sequence of times. So I said for this sequence of times we have a decomposition. And the error, in addition to having the L6 norm going to zero, has some further good properties. The tangential part of the gradient goes to zero. Remember that, anyway, that outside T7, everything goes to zero. The gradient outside T7 goes to zero, that's no news. But for any slightly smaller ball, it also goes to zero. So the energy is concentrating near the boundary of the ball. The same is true for the T derivative. And then there's a third or fourth property, which is fundamental, which is that your solution is becoming outgoing. Which is there's a relationship between the spatial derivatives and the time derivatives. And this is precisely the expression in the Morowitz formula. And that is going to zero. Okay? So that's the first thing that you do. So I will show you now how to do this. But I want to address your question about the Strikatz norm. The Strikatz norm doesn't come at this time. What happens is that once you have these properties, then you can prove that the Strikatz norm goes to zero. But not before you have these properties. But a little further composition, it comes with the Morowitz. But there's the extra profiles that we're throwing in there. Remember that we threw in the profiles that were scattering profiles. That's the point is we have to kill those. And we kill those by using this. Okay? The proof of that, I don't know how much of that I will describe, in the same spirit as the extraction of the scattering profile. Okay? And what allows you to make that succeed is the fact that you have this property. So you go back to that proof and you can extract what you're using. And it's precisely that you have this property. Okay, so let's say, so that's how you kill those profiles at infinity. All right, but let's not skip steps. Let's do this. Okay? So that's what we're going to do today. The last thing we're going to do today is this. So to do this is where we need the two times. So what we will do is prove a further estimate at these two times for which we have the decomposition. And the only way we can prove it is by using that you already have the decomposition. But fortunately, it's enough to only have the L6 norm going to zero. Okay? Okay. So we recall that we have this. That's the kind of what we get from the Morowitz estimate using the maximal function. And then we have these other two times for which we can put the maximal function here. Okay? This is what we have. And at each one of these two times, therefore, by the previous theorem, we can do a solid decomposition where the error now goes to zero and L6. Okay? So we have all of this, all the orthogonality conditions, and this goes to zero and L6. Okay? So I will use improved L2 estimates at those two times in which I have this decomposition. Okay? So I take a small epsilon, and I'm going to estimate the L2 norm of my solution in that ball of radius TIN, and I have the decomposition. So in the decomposition, I have the V, I have the epsilon, and I have the solitons. And the solitons, I split the L2 norm into the part inside this union and the part outside this union. Okay? So I have the center, the center of the soliton with the radius epsilon T sub IN, where the epsilon is the number that's given. Now remember that I have an a priori bound on how big the J's are. I can just, there were a fixed number only on the L2 norms, the supremum of the L2 norms. Okay? So this part is just the decomposition and the triangle inequality. Now I'm going to use Header inequality to go from the L2 norm to the L6 norm. So I go to the L6 norm, and if you do the calculation because it's three dimensions, it's L6, the volume of the ball is T to the cubed, you get TYN, and here TYN. Okay? That's just Header. The passage from L2 to L6. Here I do Header in each one of these balls. It's the union I use each one of the balls, and the balls are radius epsilon TIN, so I get epsilon TIN here. Remember these guys are completely orthogonal, and you can treat them as if the sum, the L6 norm of the sum is the sum of the L6 norms. Okay? So this is fine. And then the last term outside, I just used the fact that this is already TIN, and I get that. Now I'm going to recognize what happens to each one of these guys. This norm, because V is regular, goes to zero with N, and I'm shrinking the support. This one, I know that goes to zero with N, because that's what I proved in my decomposition. That's the property that I have. This one, well, this is just a uniform constant now, because I know how many I have, and this one, remember, we have good point-wise pounds, and the gradient point-wise pounds. Now this one, because I'm away from the center by an amount epsilon, when I look at the L6 norm, I gain power of epsilon. Okay? And so I have either little o of TIN for this term and this term, or epsilon TIN for this term and this term. Okay? So the conclusion, since this is true for each epsilon, is that this ratio goes to zero. Right? Because I had little o of TIN and epsilon TIN, but epsilon is arbitrary. Okay? So what I've now shown is that this L2 norm is going to zero with a faster than TIN. And I mean, this is something you want, and you cannot prove it unless you have the decomposition already. But fortunately, you only need the L6 norm in the air. Okay? Okay. Now we're going to improve. Now we're going to use that we have two times, and I'm going to do a virial type argument. So to do the virial argument, what I do is I multiply my equation by u and integrate over x less than T and T in this interval. Okay? So because I multiply the equation by something, I get zero. So I got these three things. So I get all of these things. And now I'm going to integrate by parts in T and in x. When I integrate by parts in x, what do I get here? No, it is a u. What I get is the flux times u. That's from the divergence in x. And then from the T terms, I get u dTu. And then I get what I didn't integrate by parts, which is this solid integral. Okay? So now I'm going to show that these three terms go to zero faster than T2n over T1n. This is where we want the T2n minus T1n is of the size of each one. Okay? Right. Pardon me? The first identity, there is the dTu comes from the intelligent parts. No, no, because this is an identity. When we take the secondary, it falls here, or it falls here, and then I subtract. And here, the Laplacian falls here, or then I have the gradient squared, and then I add it. And then I get u to the sixth, because that's u to the fifth times u. Okay? So I really literally just straight zero. I didn't integrate. And now I integrate. Okay? All right. So the object of this is to try to show that this in average is small. Okay? And so I do that. I look first at the surface integral, which is this guy. I use Cauchy-Schwarz, and then I get the flux to the power one-half. And then I get the u squared to the power one-half. Here I could have used the Hardy term, but somehow I used the L6 term by using Helder here. I get the length, and a little low of one, so I get a little low of t to the 2n minus t1. Okay? So that, because of the control of the flux, gives me that this goes to zero. Faster than the average goes to zero. For this term, where do I get the gain? I get the gain from the u squared. But remember that this term appears only at the endpoints of the time interval. And it's at the endpoints of the time interval where I already know the decomposition, and so I can prove this L2S. So I get it. So the conclusion is that the average of this quantity tends to zero. And I also had this. And after passing to a subsequence and renumbering, something that goes to zero can be 4 to the minus n, and another thing that goes to zero can be 8 to the minus n. And 8 is twice 4. Okay? Alright, so what do we do next? This one, you know, you can do things initially, you think, because it's a coercive quantity. It's bigger than or equal to zero thing. This guy is not a coercive quantity. So now we have to use another argument. And the argument that we use to handle this non-corsive quantity is an argument that how Jia and I had in a previous paper on wave maps in the equivariant case. Okay, so we pull back another argument here. Okay. So are you okay to go for five more minutes? Yeah? Okay. Let's go for five more minutes and see what happens. If people want me to repeat next time, I'll repeat some of the things. Okay? So I look at this guy. And again, I use the maximal function and I get that the maximal function where it's bigger than 2 to the minus n is more than 4 minus n times the length of the interval. Okay, same argument as before from this estimate. Okay? So now I'm going to see what to do with this with the other term. This kind of a little bit bad term initially. We know that this thing is bounded. So that's, at least we know that. And what I'm saying is that this bound, together with this average bound, implies that the thing has to be, that the set of points where this object is small is big, is substantial. Okay? And this is a real variable argument. It's a standard kind of probabilistic argument. But the thing that you have to do, which is a little bit different than usual, is that you don't know that this thing has a sign. But you replace that by the fact that you know that it's bounded. Okay? So you have to split the thing into a positive and a negative part and argue with those. And I gave the argument here. But let's assume that we believe this, this is really a probabilistic argument, a real variable argument. So then since this, the measure where it's big is small, and the set of points where this is small is large, we can combine and have, find a sequence of points where both things happen at the same time. Where both favorable events happen at the same time. That the maximal function goes to zero and, sorry, and this thing here maybe will not go to zero, but the limit will be less than or equal to zero. Because I have a sign here. Okay? So from these two things, okay, so here I'm telling you, you show that the maximal function, you can find the sequence at which the maximal function goes to zero, and the lim soup of this thing is negative. Because it will be smaller than 2 to the minus n for every n, so it will be less than or equal to zero. The lim soup. Okay. So now what happens? Now what happens is that at this sequence, the n, because I know this, I can do the decomposition. But just with an L6 error. Okay? Now I will use the fact that for a solitary wave, this thing is essentially zero. So I kill all the solitary waves. So that tells me that the error has to have this property. Now remember the error goes to zero and L6. So the negative, the L6 part is thrown out. Okay? So here is the fact. For any elliptic solution and any Lorentz parameter, this quantity is zero. So this is a crucial identity that needs to be used here. And how do you prove that? Well, you calculate. I mean, we know that this is zero from the elliptic equation, and then you see how the Lorentz transform affects this. And if you're patient and you do the calculation, you get that this is always zero. And, okay. Using the orthogonality of the parameters and the fact that the L6 norm goes to zero. And for the regular part, there's no contribution because it's regular and this is on a smaller and smaller set, so this goes to zero. Then we get this thing. And the next thing is, of course, we use the Morawitz thing. That tells us already that this goes to zero. Because we know that this in L2 goes to zero also, divided by Tn, whenever you know that the L6 norm goes to zero in the error, you get that this goes to zero, so you get rid of this thing. Then you know that this thing is going to zero. And now we see what effect that has on the solitons. And for the solitons, because they're traveling waves, this is zero. You know that there's a connection between the L and the C's and the T. Therefore, you know that this thing is concentrating. So X over Tn is really Lj plus a small error in the place where the soliton is concentrating. So that tells me that when I do this calculation on the soliton, I essentially get this plus a little error, but this is zero, because it's a soliton. So here we're using where the Lorentz parameter and the translation parameter are linked. To get this. So I think I'm going to go one more step. So what we conclude at the end of this is that for this error we have these two facts. Because on the solitons you get zero. And on the regular part you get zero. And you had it on the U. So then I'll show you next time how from these two facts we can get all the conditions that I stated at the beginning. So we will start with that next time. And then we will see that from all of these conditions you can eliminate the profiles that scatter to infinity in the error. And so then you'll get that the error also has the strictest norm going to zero. And then you have to come up with an argument to show that the energy norm goes to zero, because that's what we're looking for. And here comes a new channel of energy argument. Remember that when we discussed the radial case I said that the channel of energy is not true in the non-radial case for the linear equation. What happens is that for the linear equation once you have the additional properties that these errors have you can prove a channel of energy. And I will show you how to do that next time. And that's how you then show that the thing goes to zero in energy. But you need all of this preparation to be able to get to the channel of energy. And then you can do some patches. I mean somehow it's a... it was meant to be. Okay, so we stop for now then. Thank you for your patience. APPLAUSE Are you thinking... No, no, no. This works the same way for three, four, five and six. Now for higher than six there's a problem having to do with how much smoothness the non-linearity has. And then it should still be true but it'll be more technical. And I don't think we want to be more technical than what we are already. Okay, but it's only that point. So in your... No, I estimate you don't really need that factor, you need anything that would give you the little... Yes, yes. There's quite a bit of room there. But I should say that the better estimate that you get there, the more control you will have on the sequence of times that you can pick. And the more control you have on the sequence of times that you can pick, the more chance you have of passing to a general sequence. So that is the real reason why we're desperately trying to get rid of that log even. We would like to show eventually that this infinite integral is convergent. Okay. And that may not exactly be true but there will be some version of that that will be true. And then if that is true then you can choose a lacunary sequence of times. And you can choose a lacunary sequence of times then you have much more of a chance to the passing to a general sequence. But you know, many years may pass until that happens. What? Well, yeah. But it's been ten years. So if you have more questions, let's have Carlos again.
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The theory of nonlinear dispersive equations has seen a tremendous development in the last 35 years. The initial works studied the behavior of special solutions such as traveling waves and solitons. Then, there was a systematic study of the well-posedness theory (in the sense of Hadamard) using extensively tools from harmonic analysis. This yielded many optimal results on the short-time well-posedness and small data global well-posedness of many classical problems. The last 25 years have seen a lot of interest in the study, for nonlinear dispersive equations, of the long-time behavior of solutions, for large data. Issues like blow-up, global existence, scattering and long-time asymptotic behavior have come to the forefront, especially in critical problems. In these lectures we will concentrate on the energy critical nonlinear wave equation, in the focusing case. The dynamics in the defocusing case were studied extensively in the period 1990-2000, culminating in the result that all large data in the energy space yield global solutions which scatter. The focusing case is very different since one can have finite time blow-up, even for solutions which remain bounded in the energy norm, and solutions which exist and remain bounded in the energy norm for all time, but do not scatter, for instance traveling wave solutions, and other fascinating nonlinear phenomena. In these lectures I will explain the progress in the last 10 years, in the program of obtaining a complete understanding of the dynamics of solutions which remain bounded in the energy space. This has recently led to a proof of soliton resolution, in the non-radial case, along a well-chosen sequence of times. This will be one of the highlights of the lectures. It is hoped that the results obtained for this equation will be a model for what to strive for in the study of other critical nonlinear dispersive equations.
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10.5446/21552 (DOI)
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So I'm going old school today. This is how I used to present when I first started doing this kind of thing. I was inspired not to use open office anymore. So what I'm talking about is IKEE framework. And IKEE framework is an evolution of various things I've been working on. And also I want to say thank you to the organizing team. Thank you to Fimke and everybody. Like, give a round of applause. Thanks to Tight Pants. Tight Pants, man. Thank you. Yes, without you. So I'm looking at this IKEE framework. And I want to frame things a little bit in terms of a trajectory. This trajectory takes us through various things. We all began our journeys through free software, open source, and into graphics in different ways. I choose to look at it as a freeing of myself, particularly in studying art and culture. And this is me. I try to smile as much as possible. I don't know if it's like from upbringing or I think it's actually my grandpa. I think it's genetic. But I consider myself a free person. I do what I want. I make things that I believe in come real. So I'm a free person. And because of this, I can work on free software. I can make something that I think come real. The example is Inkscape. When we were building Inkscape, when we started building Inkscape, there was not a free drawing tool. It didn't exist. We made this come real because of various different people's alignments at the time. Myself being in grad school and on a fellowship, so I had time to work on this. And we made something great. And it still goes on. Moving from that, I became interested in how to also have free content. Because with Inkscape, there was so much great artwork that was being made. But how do we know where this artwork is? How do we see the quality of the work? Where does it go? And that led several of us to create the Open Clipart library and various other things that build this content space up. And the really good side effect of this, of Open Clipart, was actually that I got a job at Creative Commons. So luckily, no one asked me anymore. They're like, how do you get a job in open source and free software? I'm like, just do what you love. You'll get something out of it. There's some water, too. Oh, there's water there. So in looking at Creative Commons, I've been articulating this concept of the Freedom Stack. The Freedom Stack, emanating out from free people, we have a stack of different hardware and content, thank you, that we can look at and see if we can actually create clearly what we, as free people, have in our minds. Right? If, for example, I have an idea to build a building a certain way, I want it to look exactly like that building, or better than that building. But part of this framework is that unless we have free tools, we will not be able to get to that very clear idea. And not only will we not be able to get to that idea, we won't be able to get to it efficiently. There are many roadblocks in the way. So with the content side of things, we have Creative Commons. That allows for the solution. That allows for content to spread freely, because individuals license it a certain way. With software, we have the GPL and other licenses that allow for us to share our source code legally. Now, whether or not these licenses have had, if they are enforced or enforceable, in some ways doesn't necessarily matter as much to me these days. The main thing that I realized by Creative Commons licenses and free software and open source licenses that allows for a community to emerge. In some ways, when I look at the Creative Commons logo, I think of it as simply a social club, a social network. And I think the same way the GPL allowed for a certain kind of social network to emerge. So if you look here, we have two major problems. We have networks and hardware. And the amazing thing is that these are actually closer to us as individuals and are the most problematic, non-free spaces in this stack. So what I'm working on mostly now is with status.net, identica, and freeing up the network and free network services, which we'll talk about in probably a five minutes when that five minute flag gets raised. Actually, we should hand out different minute flags and just keep raising them at different times. I told myself I was going to be the person who makes the biggest interruption on the five minute and on the one minute. So when that happens, you'll know. Because tight pants, man, and I are in a, we came up with a plan. It's going to be a performance at the five minute mark. So status.net is really looking at this free network service problem. And there are other services too. There's, and other software. There's MongoDBs, a really cool NoSQL engine that is AGPL license. Then there's also some other projects as well, which I'm getting to. So with status.net, you can have your network, your free network service. You can move your data wherever you'd like it. There's a license that allows companies or tries to keep companies from hiding their code behind a network socket. But then also on the hardware side, there's now new cool projects like Copy Left Hardware Projects, like the Qi hardware, NanoNote. Has anybody heard of the NanoNote? You see this? It's like $100, $99 little mini computer. And the goal is to be 100% copy left from top to bottom. So we use Inkscape. We use GIMP. But we use completely proprietary hardware, like Apple MacBooks. And yes, they're really sweet and everything. But they're still problematic. There's software that runs on chips that is then burned into Asics. So this software is completely closed, nearly 99.99999% of all code that's made on FPGAs that's burned into Asics is not copy left. This is a problem. So that's another problem that I articulate here. Zoomable interface. So now getting back into what you guys are really interested in, which is graphics. So when we started Open Clipart Library like four years ago, I went to the Wayback machine and I pulled up some nice images of this. And it's pretty horrible, actually. But the funniest part is when we created this, we actually look how many years have gone by. And we didn't have any of those. And we didn't have thumbnails. Like how do you have a website of Clipart without images for this long? It's kind of sad. And Niku here and other people are like, they were drinking the Haterade, as we like to say in the USA. How can you have this site but no thumbnails? So it was a thorn in my side for a long time. And the problem came down to, so when you develop software, let's say Inkscape, you're working out here. There's all these people who are distributed around the world, and there's this source code. And people can commit to it. And now if I get, it's a lot easier to commit to this one thing we call trunk or the master repository. With network services, you have two sources. You have a live running website, and you have then the software that runs on there. So to be a developer, you want to be able to hack on this code easily. But as a system admin, you want to be able to have secure access to a server so it doesn't shut down. Someone doesn't get access as shouldn't. Like with Inkscape, you write one patch and you get S-E-N commit access. You get commit access real easily. On a web server, you don't really want that. And not only that, if you have a hosting company, they probably won't really like that either. So this is the problem with OpenClipArt Library. So we created myself and a fellow named BazelSafati from Syria. We created a cool software called IKEE framework. And IKEE really, the philosophy is somewhat rooted in the concept of chi, or this idea of energy that flows through all things, that's a really cheesy way to describe it. I really don't like this sitting thing, man. It's really bumming me out, actually. Man, you guys have been sitting here the whole week, and I've heard very few laughs. I'm really not happy about this. I think we need to stand up and do some jumping jacks or something. Maybe we should go on a run afterwards. What do you think? No. So IKEE then is actually a Japanese martial arts. And the concept means I, means join, and chi means spirit. So let's say it's joining spirits. So we're joining the spirits of these two places of focus together. And this software is all AGPL licensed, so it's back to this free network service idea. So the source code itself, if you run this and you make a plugin, then you need to contribute it back into the commons. So the idea is that it will scale up quicker in terms of growth and use. IKEE framework is quite interesting because it builds upon some of the concepts that we've learned by using WordPress, Drupal, and other engines. OK, there's very simple things when you design a web page. There's like a header, right? There's a sidebar. There's a logo. There's a content section. There's a footer. So the idea is to really look at building websites in terms of widgets. And not only that, it's doing what many say you should not do with PHP, which is running database calls and allowing people to edit the code on the site directly and giving out levels of authentication on the site to different users. So you can think of something like Open Clipart Library, where there are artists who are contributing artwork. You can also think of another class of users called librarians. The librarians are helping tend to the clipart, tagging it, doing other things. You want to be able to give different levels of access to be able to create and to tag. And or even more hardcore users can write direct SQL calls and build widgets and other types of software right in the interface. The other thing, there's very quick access to AJAX through jQuery, so you can do really slick, quick interfaces. And by creating these widgets, you create a system of using URLs and cascading widgets to build websites rapidly. So a way to look at iKey Framework is you have a URL slash a widget. The site gets all the widgets from the iKey widgets that contain the URL. You process, there's an iKey markup that's very simple, markup language inside of the widgets. And then the page is rendered. It's very quick. And because of this, we now have the new open clipart. Finally, after six years, we have thumbnails. So you can see here already the site is growing quite quickly. Now, in the world of Web 2.0, my friends at YouTube, he was telling me that right now at YouTube every second, there's 24 hours of video that's uploaded. It's quite amazing, right? So with open clipart, one of the amazing things is even though there's over 30,000 clipart are all quite high quality. And my personal belief is that's because the tools that are being used and the people using it are focused on this type of quality. And the community as well is really focused on building something really interesting. Here's another factoid. Flickr has 0.004% of all users actually upload images. Can you imagine that? So this kind of concept of a read-only right, read-only or right-only culture, read-right culture, there's most of the people who are simply reading. It's actually kind of similar to a database. Most database calls are reading, right? They're not rights. So it's very interesting to look at this. The open clipart community is an uploading community. So let's check this out. You can see that since the site is launched, this is when we launch right about here. And it's gone off the charts in terms of uploads. Also, here's because this is a community project that I can easily show you the stats. The site is linked on Wikipedia now. It's used in major news publications. You see cliparts on the streets. You see them in bookstores randomly. Because all the clipart's public domain is spread freely, you don't have to attribute the author like you would with the Creative Commons attribution license. So the idea is the barrier is as low as possible for this artwork to spread, and it has. So most of this traffic is due to the Wikimedia project linking to cliparts, which is really great. Also, you can see these are the stats now. We're clearly hitting the target on the website of the different links inside of the page. But so open clipart's still growing. And there's still lots of work to get done, and there's still lots of roadmap items to hack on. There's a whole new class of people that have come on to the project because of this. And I encourage you all to check out the site and see what's happening. Here's the project itself. So if you have your own website or for your own project, you need to build something rapidly, or you're looking at building a web application, you can do this really quickly. I've been thinking about doing a photo site. We talked about doing OpenFontLibrary with IKEE eventually. But the other thing I want to say is you guys should check out OpenFontLibrary's new site. It's so cool right now. I know several we've been looking at. It's running on CChost. But the great part is with IKEE is very quick to port over old software to this new web interface. Let me keep moving here. So if you want to contribute as well, everything's in Launchpad. Other sites that are running IKEE right now, this is Discover Syria. Anybody gone to Syria here? You have? No, not yet. Anybody want to go to Syria with me soon? Yeah? All right. We can get on like a train. No, airplane yet. Also the open color site is built with IKEE framework. And here's a new one that I've just seen that's pretty interesting, which is readthebible.de. It's a German Bible. And of course there's a new project, Shareism, that myself and Christopher Adams are working on that's running on this. Shareism is another kind of concept like Qi hardware building on the idea that the more you share or the more you give, the more you get back. But also in the development space, there's been others. This is a developer, Ronaldo Barbicrano, who has developed IKEE Press. And the idea behind this is to hijack WordPress. And so here you can see really quickly, you have a WordPress database, the crufty old WordPress code that slowly renders HTML pages with IKEE Press. IKEE Press is actually a plugin to the IKEE framework. And simply it just does direct SQL calls to the database and then renders the pages. So you get like a massive speed up like 10, times or something like this. So you could actually use the WordPress back end to edit, but you get the speed up of using IKEE framework to render the page. And ideally you would eventually just shift completely to using the IKEE framework. What is that? We've been hearing that the whole week. Is that a cell phone? Who put their phone on that? Can you go smash that? No. I feel like I have to lighten up. I feel like I have to like perch it up with my shoulder or something. So the final thing I wanted to go into a little bit is, I'm going to talk a little bit about, kind of rant a little bit, about building community and business. And the interesting thing I found about, finally I'm freed from the microphone. Let's give a round of applause to the microphone. So building community and business. Okay, so in the trajectory, in my trajectory and working in this community, I've been concerned about projects and how to actually grow and sustain them. And I think what's interesting about what we've done on our projects is that we've built really interesting code, really interesting communities, but they haven't grown as quickly as a large company or even a medium-sized company that can help build the applications. With Statusnet now, working on Statusnet projects, it's quite interesting. We're moving at such a fast pace in the development of the code because there is investment, there's capital. We can take a more military-style approach to this. So in my own projects now, I formed a company called Fabricators. The idea is to have a free community alongside of a company. And when you have this model, you have both the benefits of the free software project and also the company to build the thing. So with IKEE Framework, what we're doing is a similar thing. So there's ickyframework.org, and then soon there's going to be ickylab.com, and ickylab.com will support the efforts of the community. So that's what I want to do. I think from the work that Tom did, the great work that Tom's done, obviously from the film and everything, you can see how great of a project that they've built, various projects have learned from that and I've learned from that. And so I wanted to say an end with this and just say thank you to everybody here for all the great work that everyone's done. And also I wanted to say this has been the most amazing LibraGraphics meeting. I think because we've been focusing on the software and we've also been focusing on content. There's been a lot of good content discussions and also having a theoretical base, like a metaphor man. A metaphor man was really helpful and even tight pants man was really helpful in moving the discussion forward. So thank you. APPLAUSE Oh yeah, I forgot about that. He never made it to the five minute paper. The performance is that if someone asks a question. Questions for John. Hey, I think the iKey framework is a very neat project. I like the idea of storing the controllers in the database, though I think still like a problem to solve is how that relates to the versioning, but you know, it will solve. But I was thinking like what's your thought on, I think there's quite a bit of a dilemma. Like you use a license which is more like copy left than like the liberal like MIT like licenses. And I think there's really a lot of development going on by professional web developers now on the Django frameworks and all of these things that are like very liberally licensed. And I think they can actually work on that with the money of their company because these are so liberally licensed. But at the same time, of course, that causes also, well, you say it causes a lot of code to stay behind the scenes and I guess it does, but at the same time it does encourage a lot of collaboration from the world of professional web developers. What's your thought on that? How would that impact the IK family? So particularly, so I mean in the next session we're going to really get into this a bunch more. But there are way more web programmers out there. There's way more people who know HTML, CSS, JavaScript than know C. Right? There's a lot more people. So this is what's really allowed for this web explosion and application development and browsers and standards. This is allowed for this massive growth. I mean also what's also helped this is investment and start-up investment. This has really powered this whole web 2.0 evolution. But we can't forget, I've been kind of bummed out. I've been going to a lot of conferences this year to talk about Statusnet and I realized that going to some of these conferences there's this kind of similar discussions all the time. And this is another reason why I think this conference is awesome because we had new discussions and there was like a focus on what we're going to do and this excitement. A lot of the Linux conferences are about newbies like, oh, we need to install a wiki, we need to install this, we need to do this. And what I consider is stability. So what that says to me is there's a stability. Linux is a stability layer. The web is free software. It's done. It's done. That's solved. On top of it now are closed web apps mostly like 99.99999. The tools that are being used are free software as well. And the languages, PHP, these are all free software. But the web applications themselves are not. So AGPL license really helps this. It helps that, like Google for example, right? Okay, Google is using, what are they using for Gmail? Why can't we take the Gmail software and get it and go and run it on our own web server? We don't have that software. The license, and they're using GPL software, AGPL license really allows for, okay, you made a change to this. You need to give it back. It's on a network service. It's a small provision in the license. Why would commercial developers who earn their work making these closed applications want to work on a framework and license like that? So, okay, so, it's like back to the same question of why you'd want to use free software. Okay, so I think there's a few reasons why. One is if you have a really great piece of software like Statusnet and you want to build a business, the license is not important at all. It's about how good the software is. The license, the AGPL license is really a commitment to the community and to the software developers to know that if they contribute some patch or some plugin that the code will still be available and that they're in many ways are also getting into a larger ecosystem because of this. But I don't think that you are going to get a lot of web developers to use a software just because of the license. And I also don't think that you're going to get a lot of people to use software purely because of the license either. No, it's just that I've seen on like if you look at websites of web applications, like I saw for example on the KPHP site, like they make really a huge point of the fact that they use a very permissive license because that gives developers the confidence that they can use it for commercial projects and sell the technology to their large corporate clients. So the strategy with Statusnet with IKEE and with free network services and free network service companies is to be as completely open as possible. Okay, how do you compete against Twitter, right? You can't. The only way you could compete is to be completely open from top to bottom. So it brings the commitment to the religious sect, to our friends, to the people who are really passionate about software and to build this kind of social network I talk about. So there's another thing too which is, so like okay, with a free network service like IKEE, you have the problem of both trying to get developers but also to have a business. On the business side, AGPL and free network service doesn't mean anything. Open source means something. That's buzzwordy. That's for like CIOs and the C-level class. So trying to convert developers using an AGPL license is still early on. I mean Google still doesn't support AGPL license inside of code hosting because they think of it as insignificant. But as there's now like 22,000 Statusnet sites online and IKEE sites are growing, I mean there's like 20 or something. But when you start to have something that's really scaled up like WordPress, okay, WordPress has millions of WordPress installs. That is an amazing company actually. They have 60 people that work there. They have a mega business. The people who work there are really smart. So if you have something like Statusnet like IKEE, the idea is that you will scale up like this and it's good software and at that point when there's enough people using it, then they'll start figuring out, okay, free network service means I can make more money as a developer and then you get more developers in. Thank you very much, John.
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In the past, applying a free software development style to web applications blocked development on the Open Clip Art Library. The project has nearly joined the #FAIL list multiple times. Since web sites are centralized pieces of software running continuously, there is a need for secure access to the live code. This forces a division of managing a running website, merging software changes from developers, and keeping development on the software progressing healthily. To complicate matters, a site like Open Clip Art Library has an active base of librarians and artists uploading and editing new clipart. The new Aiki Framework aims to solve all these issues.
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10.5446/21551 (DOI)
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Hello. I'm Barry Thru. I'm from San Francisco. And what I'm looking for here today is to generate ideas with people about some new types of software performance tools, compositional tools that people can use for real-time interactive art. I come here by way of a few organizations. This is a beam foundation where a California nonprofit that develops tools and evangelizes their use for music using the aesthetics of the 21st century. I work with some organizations like Recombinant Media Labs, which is an organization doing spatial media synthesis. I'm the chief technician for this organization, and we do a lot of surround sound and video production, 3D surround sound with multiple immersive speakers. And some more work, some commercial things. This is an 18-foot multi-user, multi-touch wall that's in the Hard Rock Hotel in Las Vegas. And it displays a number of rock memorabilia that can be thrown down the wall and across the room, and it displays information when you interact with it up to six users. This whole resolution, they're all 4K back projectors, and there are four of them. So I believe it's the largest multi-touch user role in existence outside of the military. And I also do some work with event organization in San Francisco, there's an organization called the Gray Area Foundation for the Arts that I work with. And we do some sort of educational and gallery types of situations. And so everything that I deal with is technology for digital arts. So I'm involved with a lot of system design, a lot of working with individual artists and museums to create the ability to show these forward-thinking works. And in particular, I'm interested in art that's immersive and interactive. Both type of works that create certain types of cultural capital and experience economies and works that engage multiple performers, audience members, and those types of things. But the question that really I've been dealing with and focusing on lately is the idea of real-time art, real-time performance, the interpretation of existing works by performers, and the types of tools that are needed to accomplish those types of things. And as a warning, I'm going to talk a lot about music here. The reasons being is that music is kind of, although we're converging in every almost performance artistic work, has some sort of visual element these days. Music was far ahead in that it was the first time-based medium, and it's always been interactive in the sense that from time immemorial, people gather together to make music, and due to its nature, it has to be present. Time has to pass for music to happen. And so it's always kind of been real-time until this century. And so I'm going to go over some of the problems with this real-time interactive art, what obstacles need to be overcome. Talk a little bit about what myself and some of my colleagues are doing, the kind of projects that we're trying to work on, and then hopefully have some time to get into a little bit of a tools discussion and talk about some of the things that are available, that we need, and a way open source type of things can be involved. And so without further ado, we'll get right into the problems. One of the big problems is that there's a lack of interactivity that's come up in the 20th century in art. And interactivity is kind of this big buzzword in media art conferences these days, but it's easy to forget that it's not something that we're gaining, it's something that we lost that we're trying to get back. All kinds of art were interactive until we started using technology that, through its limitations, took that interactivity away from us. You know, the technological innovations in the 20th century reduced the opportunities for musical interaction in several ways, and it did so by kind of allowing, in a certain sense, different interested parties in the production of a work to not have to interact with each other anymore to get the work done. For example, recording technology, whether we're talking about video or audio, takes the audience and composer, frees them from having to be in the same room with each other, which fundamentally changes the way music sound, videos, experienced. Multitrack tape recording technologies made it so performers didn't have to be in the same room to make a track, or the same time. You have things like performers re-recording over older works and some of those types of reappropriation, and live tape music at performances now even frees live performances from having to do everything in real time. So there are a lot of works with pop music through lip-syncing, etc. So we've gotten away from a lot of this real-time live situation, and I'll go into why that's important a little later. But in the last 25 years, we have gotten higher sampling rates, more distribution methods, more accessible distribution methods, and the means to use an increasing number of effects in the palette. But there's been very little progress in terms of live performance. The ability to gauge and live reinterpretation of electronic works is something that is vitally important to culture, and through some sort of obsolescence of technology and the inability to transfer works to other medium has largely been lost. So I'm going to define kind of three things that have to be overcome to free art from these machines. And it's kind of worth noting that while these are at their core technological problems, there have been attempts since very early on, certainly in the compositional world, to solve them traditionally by composing techniques. Extended plane techniques have augmented the abilities of traditional orchestral instruments. The use of improvisational elements led to a blurring of the line between composers and performers. And even indeterminacy with composers like Cage has led to a larger role for the audience in kind of filling in compositional structure. So the first problem is kind of the opening of the palette and the filling in of the palette to kind of any, and most of these metaphor things I talk about are going to apply equally well to graphics and video when you guys catch up. And it's largely a matter of this computational power to make that happen. A quote by Russelo, the year of the 18th century man could never have endured the discordant intensity of certain chords produced by our orchestras, whose members have trebled in numbers since then. To our ears on the other hand, they sound pleasant since our hearing has already been educated by modern life, so teaming with variegated noises. But our ears are not satisfied nearly with this and demand an abundance of acoustic emotions. This opening of the palette really gives us more metaphors with which to compose works and speak to our culture. And while digital technologies have done a lot to bridge this gap, they've also led to a culture of kind of pre-recorded looped track-based works, even just empirically looking at, you know, you go see a DJ or a VJ and there's definitely a single performer there kind of looking like this, which is certainly not theatrically engaging. Well, you know, much has been gained in the terms of voices and the variety of texture and accuracy through composed composition, much has also been lost in the realm of human interaction and performance. Kind of a better answer than digital technologies for why these are problems is because it's difficult to address this or even the two other problems I'm going to talk about. The second being giving compositional access to performers during the real-time performance. And in this sense, we're talking about really bringing improvisation back into electronic works through real-time data and metadata manipulation and giving a performer the ability to unfix elements of the composition that can be filled in in real-time. And the third thing is creating a standard for scoring. These three problems I'm talking about get kind of progressively harder as we go. Because the reason works and works like music are classic is because, A, they can be picked up by any ensemble at an arbitrary point in the future. And that, for example, why Bach piece is classic is that I can pick it up anywhere in the world and play it and do a reinterpretation of that existing cultural work. And this is something that with electronic works, which has been the majority of the music created in the last, you know, 50, 60 years, is fairly impossible because it cannot be, because of the closed systems with which it's created. So we get back to the technologies and aesthetics of the 21st century. And this kind of can all be summed up in the fact that there's a divide between, you know, these types of metaphor machines and information processing machines that we have. And obviously this is a loaded example because it's a company that certainly has mixed messages in terms of its openness. And people like this, this is the Cronus Quartet from San Francisco, which is also kind of a loaded example. Because, you know, they're one of the premier new music performance string quartets in the world. But also they use kind of technology in gimmicky ways a lot and will kind of do throw off pieces. The technology is not really integrated with their performance structure. Again, I entitled my talk, Baroque Dreams, not just because I'm hilarious, but also because I and people of my ilk have a certain affinity for the Baroque because new technology creates new art, which is very much what I'm interested in. For a couple of reasons. One is that obviously technology is a metaphor for ourselves. It's the only way we have for, you know, interacting with the environment. And just as modes of human existence change over our time, so do our modes of perception. So when we talk about, you know, the kinds of art that we're making in our culture, it's silly at best to think that old types of technology can create the metaphors that are so relevant to us. And the other, of course, is the technology embeds ideas and cultures in the curation of the choices that are available to you, in, you know, the creation of the instruments. Things like MIDI and event-based sampling certainly have created entirely new genres and cultural movements. And so, you know, if you look kind of a timeline of instrument development, you'll see the 1200s, you had, you know, notation people like there was a Mont Guido de Arezzo, that the Guidonian hand was a huge, you know, vocabulary and musical movement. In the 1600s you had a lot of new instruments with the Baroque period. The violin being technologically changed to be louder and carry across an entire ensemble took music out of chamber, you know, the chamber setting and brought it into kind of an orchestral situation. The 1700s with pianos in equal temperament allowed works to be cross-transposed across keys. And then you have, you know, the ladder development of instruments with banjo sax, bones, jazz, certainly electric guitar. And the great thing about, or interesting thing about all of this musical development is that they created, you know, new genres, which is something that largely seems to have become lost. In the 20th century we had this thing that certainly, if not an end, a slowing down of styles and genre production, if you even do a little thought experiment and think of something like the, you know, temporal versus cultural distance of the big band to the Beatles, and then say Nirvana to the music that's being made now, if you contain to pop music. A lot happened in the previous time period and not a lot has happened genre-wise in the ladder. And so the question is kind of why, there's not a new generation to a new style anymore, which certainly used to be the case. There's been sort of a genre stagnation. And we have a world with problems. You know, the big cultural events such as, you know, a giant oil spill or new diseases or, you know, threat of nuclear war aren't spawning artistic music movements in the same way that they used to. Certainly World War II, World War I, major cultural events had corresponding, you know, prohibition, had corresponding types of musical styles that went along with this. And our kind of answer to it has been remix, which I would argue, Appropriate of collage only gets you so far, you know, because that's kind of been what we've been doing for the last 40 years. The first digital sampler was in 1969, and for sure, Pierre Schaefer, our D.F., have been doing things way before that. And so, again, what I want to get back to is this idea of reinterpretive culture. The ability to pick up a work and not replay it in real time. One of these problems with remix being that it's largely an offline process in the sense of, you know, you go and get your gamut of materials and recompose them into some sort of satirical or interpretive work, but it certainly can't be done with current technologies easily in a real-time matter. So, if you buy my argument, which you may not, then, you know, now what do we do? And so, here's what my and my colleagues are kind of doing. We're trying to get these guys into there, and we're trying to do it in a way that's transparent for them. So, it's largely a question of interface, but not novel interfaces. Again, we want transparent interfaces, and we, being at the Beam Foundation, have, in this sense, developed a group of technologies to leverage the years of virtuosity of these kind of performers and bring them into the computer. So, our kind of first technology to do this is called the CABO, the kind of founder of this foundation whom I work with is named Keith McMillan, hence the K. And it's a sensor bow for stringed instruments that takes the performance data from your plane and sends it via Bluetooth connection to the computer. And it's outfitted with a number of sensors, such as three-axis accelerometer, there's a grip sensor, hair pressure is sensed, the distance from the bow to the bridge is sensed, the distance along the bow, lengthwise is sensed, twist and tilt, you get gestures, mappings, and articulations. It's built for the stage, so it's light. This is not like an encumbering device. There's no weight difference from a traditional bow. It's robust in the sense that you can't break it, again, built for the stage and is for an entire string quartet, which takes care of our gestural and kind of performance data on the gesture side. And another product called the string quart, which is a little box that looks like that, which through a certain type of interface gathers the spectral information, the actual audio data from plane. And so you get a group of information like loudness, brightness, noisiness, even auto-harmonic balance. And the point of all this is that it's basically metadata about the performance that's being used to control the composition in real time from the performance. Our prototype ensemble to do this is called Truometric. And we do several performances with live video integrated. You can see everybody's looking at a computer screen so they can see kind of state information from the composition that they're playing through. And all of this, this is a guitar violin and a bass ensemble. And all of this information that's being gathered is networked through a central computer system. Before I mentioned the kind of metaphors of our century, I would say that this would be a web metaphor, obviously, in our age. And so I think that networking together of this information is kind of a vital step in the creation of works that can speak a little better to our time. We've done things like control robots and some more novel, funny things like that, had them dance around. And so after this interface is kind of completed, everything turns into a software problem, which gets me to tools. And in the realm of music, there have been several tools that have been available for the production of sound from a computer. There are largely programming languages such as C-sound, Super Collider, Chuck. Super Collider is a small talk based language. Chuck is out of, I guess out of Princeton, it was developed and it's a language with very strict timing that's useful for music. And there have kind of been some more things in the video realm, like processing in open frameworks, processing and develop as a teaching language. And open frameworks is another, it's similar to processing if you're familiar with that and run, it's based on C as opposed to Java. Kind of the problem with some of these tools is that they enforce this idea of the artist programmer, which there's nothing wrong with it per se, except that the idea that the same person that creates the work has to deal with all of the technological infrastructure of the work is, well, can be useful for many artists in a large scale is probably a bit naive. And you know, instead of saving work in our current age, technology kind of has just allowed everyone to do their own work. So we have this kind of multiplication of labor instead of division of labor. And so what we want to do with our kind of software is keep this separation, the specialization a little bit. So a kind of modal software that can be useful to the programmer when they're programming, the composer when they make the piece in a different set of ways. And when the performer plays, they don't really have to worry about the programming or the compositional process when they play the piece, which gives you a division of labor and this specialization turns it into kind of a force multiplier, which allows each of these people to, through their specialized roles, such as performers that's been 20 years building virtuosity on their instruments, and leverage that towards the final construction of the work instead of having to delude their efforts being a programmer or technologist. And of course, in this kind of triumphant here, eventually, and even before now, we've had to add audience. So what I'm looking for is to make platforms for these works, not just tools that can do one-off works. It's not enough just to have a framework that can create a work. You have to have a platform that can support multiple works and create a kind of ecosystem of things with scoring, et cetera, to support this type of thing. A tool, it's used a lot, it's a tool called MaxMSP. It's a visual patching language. There are a lot of variants, such as a program called Touch Designer from a company called Derivative in Toronto. There's the Apple's Quartz composer. There is a program called Bidule from Plogue, which is also in Canada. And an obvious derivative being PD, which is an open source version of MaxMSP. Unfortunately, it lacks enough features and is, in certain ways, undeveloped enough that it's not useful for situations where works have to be developed quickly and with limited budgets and teams. So I guess one of my pleas here is that I could talk to people. PD, for example, has absolutely no GPU leveraging for its graphics, and it's kind of falling behind in that respect. But the next step for where these things are going are going to be the cloud. So it might be useful to kind of jump over PD a little bit and go to some of these new emerging technologies, one of which just kind of came out today and let me show you some of this. First, I'm running out of time. So let me show you some of the software that I work on. This is the software that comes with a bow, and let me just go over real quick to kind of understand what I'm talking about. The things for the settings for your composition are stored in this hierarchy of presets. This preset can control all the other presets for the entire program. And for example, here is a kind of standard effects rack that would happen in a musical system, a parametric EQ here. And obviously I don't have the whole bow and system here, but what you do is kind of open these mapping screens and choose a source, which there are many of, such as the X-axis celerometer from the bow. And then destination, such as say I took the low gain on my EQ. And when the data came in, you can scale it and table it and kind of mash it into a form that's artistically useful for you. And then when the data comes in, you can see that the parameters will change in real times. And so you kind of curate a space of possibilities that through performance you can create a trajectory through. And from piping your audio through a system like this can create a composition that both has features that are the same and features that are un-fixed in real time. One minute doesn't have a smiley face on it at all. So, unhappy one minute. Oh, see now it just threw me off because it destroyed my mood. But I don't have time to get to the web-based patching language alternatives. If anybody's interested in that, then find me and I'll show some of them to you. And if you don't know visual patching languages like Max for sure come and talk. I'm going to end by talking about one of my favorite new pieces of open source software. The CTO is here in Brussels and it's called MuseScore, which is an open source scoring program to compete with things like Finale and Cibelius and other ones that are out there. And let's see on a final note I would say that a lot of these programming usage metaphors that I'm trying to get out of this software are going to apply through our graphic systems equally well. And so a lot of what I would like to talk to everybody about here is ways in which those kind of graphic systems, real time graphic systems can be developed to bring the visual part of this puzzle into place. And so I guess that's it. Thank you very much.
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This talk will cover the issues of bringing live interpretive performance back into electronic music and multimedia performance culture. Issues of technology obsolesce, interface, types of users, hardware, and historical cultures patterns will be discussed. Ways the open source community can help build tools that will be useful to the video or music artists interested in interpretive performance of works will be suggested.
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10.5446/21498 (DOI)
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Thank you everybody for waking up what seems so early. Let's get started with my talk. So, even that works. The first time I use this, so it's going to be a technology miracle working out of the box. Good morning, my name is Peter Sikking. I'm an interaction architect. I run a Houtti company in Berlin and this is also my fifth LGM. Every year LGM is my anniversary of being wrote into GIMP and so, and every year I try to do a talk that sort of points forward. I always show this slide at the beginning of my talk. It's like what's an interaction architect? Well, can we all read this? Yeah, there's just enough contrast. This is what a normal architect does. The environment is a street or a landscape and designing is, but not about making it pretty. It's about shaping an experience when you approach and enter the building and work and live there. That's what I do. It's really similar. The environment here is desktop, web or handheld and again, it's not about making things pretty. It's about the experience of using programs, certainly in GIMP. Well, you can get the job done when you get a big job to do and it's about how to master a tool for masters. Yeah, the topic I want to talk about is integration of Gaggle and GIMP. I thought I give a two minute introduction to what Gaggle actually is. It's basically all in the inside and it's about a different way of storing and processing images. So, not enough contrast for that. Okay. Luckily, the point of this slide was to show that there's a huge graph here. You cannot really see the details anyway. So, that's working out pretty good. So, let's see. Oh, we can see a little bit more. Okay. The thing I'm highlighting is at the bottom, I'm showing you some elements of what's in a Gaggle graph. The first thing is these things that generate content. This thing reads an image from file and this other box generates some text in vector into pixels and then it gets processed further. And there are all these chains of commands that do stuff with these pixels, move them, transform them, blur them, etc. You see they tend to turn up in sort of chain like structures. Then when you've done quite a bit of that in parallel, then there are compositors that mix things and put things on top of each other with different blending modes. Gaggle got a lot of different compositors, more than GIMP even built in and there's also all the portrait stuff which I think fits mostly for vector stuff. And when you put it all together, then there's some kind of image sync that gets it out of the system. In this case, I think it's a display one. Or you write it when you're exporting your composition because that's what we're talking about, not about the image but about the composition. You export it to some file form with like PNG or JPEG. So yeah, great. What's it got to do with me, Mr. Gim. So four years ago around LGM, it was really a factor to join a project that GIMP was going to move from handling loads, just loads and loads of bitmaps and operate directly on them to this graph-based system where the images themselves are never touched. They just go through a pipeline of operations and are spit out at the other side. And when you save this Gaggle tree into a file, then the images are also never changed. So you're always able to change the operations in between also a year later. So you got loss-loss editing. And that got me quite exciting because that's I saw as a potential to shake off all the some of the old ways of working and cure some of the existing ills in graphics processing, whether it's GIMP or another program. And it really was a factor in me deciding to join the club. So today I want to talk about, okay, you've seen a bit of the technicalities and although the overview picture didn't work out so well, that was just a small graph but it was already having tens and tens of objects hooked up together. So I'm going to talk about what kind of UI I'm thinking of to integrate this into GIMP. So one of the things you can do when you got a technical model is to put it directly on screen. You really cannot see anything. And there these are all boxes with the parameters in them and they're all hooked up together with hoses. Yeah, this is a blender screenshot that I found and it's imaging, it's processing these images through all this graph down to there. And I think this is not something for creative people to use or not in general for artists who work within the vision of GIMP. So what this is is visual programming. Last year the question already came like, what it is with hooking up, you want to show the graph and I was like, no, that's visual program. We know that from the 90s and no, I don't see that creative people mostly want to work with that. It might turn up this kind of modeling GIMP because part of the GIMP vision is to really be about research of algorithms and to really dig deep inside the representation of the processing itself. But it will be sort of a separated corner just like this part of the vision is slightly separated from the rest of the normal statements about high end photo processing and creating original art. So what you usually have to do is sort of bridge what goes on technically and I have to understand it and then go to users and focus on the activity, focus on what's it like doing this kind of high end photo and art making work and generalize that, understand it, understand what kind of models are playing there in users' head and here's what I came up with. So the focus is yes on the image, on the result and certainly in GIMP in general you're working on the compositing that form a bunch of layers. It's very much ingrained into the model, the compositing and we highlight one of these layers and you work on them, you just do one operation after the other and you do a little bit of this and a little bit of that and you focus on that one layer in general at the same time, you do another operation. So when you look at this then I think we got a model because those layers of there is of course represented by the layer stack in the application and you can do the same for the operations. I call it the manipulation dialogue, the manipulation stack. That's a working title. I'm not completely sold on that and also now that I put some headings on this and call them already dialogues, don't think this is a mock-up, this is really just an interaction model of how this can be used. So now we're getting closer because this can be a representation in GIMP of that complex gaggle tree you've all graphed that you've seen before. Let's see what are we going to do. So I think we're going to show you now how to work with this, how to put a new operation on this stack and it will really work as people are used to. You choose from menu, so from toolbox to tool and you start working and you see you get a new operation at the top that's highlighted and then you dismiss that and okay the image doesn't show it but it's done. And yeah with that we have already captured quite a bit what was in that gaggle graph. I have to show you that here instead of operation I've filled in some names to make it a bit more tangible what's going on. So that's the load, the image, that's that chain of operations that compositing we talked about is here and the output is over there and this put into an application is exactly kind of things I talked to you about before. Now I'm back on track. So putting a new operation here was the easy part where it gets more exciting is to go back in the past and revisit an older operation we've done before maybe today maybe a month ago and re-change that curve and by changing the curve all the other ones will be applied on top again and you immediately see the results why you are actually changing that curve in that dialogue. So that's where for me the while starts. So there when you see this model some more easy things that can be immediately done we almost these guys layer visibility we can do the same for the operations you can just switch them on and off inside stack so you can see before and after and of course you can you can do that also for the month of operation to see still what the difference is does it still make so much of a difference and maybe I have to adjust it. What's also quite cool immediately is that because it's got the same list structure you can just reorder the operations and move something to the top for a bigger impact if the operators don't commentate. That's why everyone is highlightable so you can immediately start thinking about copying and pasting one or more of these operators and pasting them in the same layer pasting them in a different layer but just highlighting it and just a much more free way of things you did before to apply them to something else. One thing that's a bit of a bit of a question is we just grab one here and drop it on a layer over there what happens then is that a copy or is that a move of the operation. If you add here very much to the files of the folders metaphor then you would say it's a move but I think it's going to be a copy but I'm not decided on that one yet. So before we see more cool stuff I'm going to have a slide inter-metall and it's a very Catholic country Belgium so what's the Holy Trinity. So if I take this image and I do something to it Zürich airports get invaded by Martian laser beams then yeah my question is then like how did I do that. Did I pick some tool from toolbox and just did it like that. Did I build some kind of a fuzzy selection and then applied some operator on it or did I put some adjustment layer or normal layer over it and blended it and use the mask for that to work out the result and the answer is that I'm not going to tell you that because it doesn't matter you cannot see the difference and actually from point of view of GIMP it really shouldn't matter. What they all got in common is that they can be broken down at the end again every one of these actions to an operation that you're doing and some kind of a grayscale single dimension mask of applying it this is for what you'd smear on with the tool this is what your selection actually is and this is what the layer mask also is. So what I'm declaring today although I've discussed this before with the Kaggle mice picking themselves is full emancipation and full equality for these three ways of doing things and from the point of view of GIMP there's going to be no preferred way or no single way to get any of these things to get anything done there's always going to be three ways the three ways that I sketched before and really even with our well with our one million users that it's totally up to the individual user on the individual moment in that individual composition of making to really figure out what is the most logical and plain obvious one to use for that. It really depends also predominantly on the person and what they're comfortable with and even down to the feeling they like to have of control or really with the hand tool to do it in a free flowing way that determines what they want to use. The reason I'm injecting this into the talk is that and that's very necessary for the following reason that is and that's very gaggle related. The layer abuse that we've seen for years and years. First of all there is the heck of the 90s the adjustment layer as we know from Photoshop and yeah from the moment I started working GIMP I couldn't believe that when you had a single photo and it's sort of represented as a single layer and I just want to fine tune the curves and be also able to fine tune it later and then when you do that in a non-destructive way then you're going to put another layer on it and it's like wait a minute my photo is a single layer why kind of do this that directly on it. So I've been a long time even at all against adjustment layers in GIMP but because of the trinity I'm now seeing like it's the third way of getting things done so it's going to be fully supported but that kind of use got to stop. The other thing is that in discussions about gaggle with the people involved implementing it there's a lot of talk when in that graph you see sort of parallel branches and there's like oh maybe a couple of pieces of text generated next to each other that the talk is pretty soon like and each one goes on its own layer and like ho ho ho wait a minute stop it right there. That is not in anybody's interest when their model of thinking is like well these are just labeling up some web buttons and that's solidly within the vision of GIMP to do that kind of work so can I just have one text layer to just lay them all out like that and get that done so that's got to stop and in the Catholic way here's the dogma. Only users decide to create layers. The commands really say something like new layer copy layer pasting layer etc that's obvious and conscious ways to do to make layers it's not like when you do a normal paste it shouldn't show up as a fake layer or something or immediately be shown as a layer and be treated like that from there on. It's a user's choice and it's not ours so we're going to adhere to that. Users use layers as a logical organization of their file and it's their logical organization and nobody certainly not we are going to force them to use more layers than they are comfortable with. That was number one from there was a reason for really stressing the Holy Trinity there's thinking about this for the talk is what two implications that I that is certainly realized if you fully pull it through and that's the first one is okay you should be doing be able to do anything with a hand tool so that means at the end painting with anything so I always have the example of oh just want to paint with noise or that would be nice if you could just take some tool and paint with noise it really goes down to that any plugin you should be able to paint with the results on your campus and apply it with that mask that you're actually building up. These are also plugins that developers have never seen before. Just take your brush in effect and smear it on the canvas. But I think it gets really interesting if you combine this with the new paint dynamics that especially Alexia is introducing and I'm also working on this combined with any kind of fact that you can do smear with a lot of control from your tablet on the canvas is something that gets then I'm quite excited about the other side of this is of course the adjustment layers I never wanted to have but I have to accept also have to be able to apply anything not just the basic building operators and stuff like that it's got to work with any plugin same deal. Else you don't have the whole eternity and yeah that's the new game dogma. So back to the ranch. So we've been talking a bit about this grayscale masks and this is a representative station of layer masks in the in the later dialogue. So when you got them here then you can also have them there. This is when you use that hand tool from the toolbox and you smear it on the doing the effects with the settings plus that grayscale mask that you can actually show next to it in the actual operation. If you apply some kind of plugin on a selection then that selection becomes the grayscale masters right there and then. That gets pretty cool because one year later you go back to your file and just like layer mask you actually highlight the I gave myself or so. You highlight this that mask itself they can edit it again. This grayscale bits needs to be there inside the file. I already warned about that that that may need some clever sharing of the same mask because else you can just pile up but it needs to be there because it's part of the operation you did one year ago and you need to be able to to change that. The delta includes adjusting your own painting by erasing over it and using some other paint tool to go over it. So rushing towards the end. A couple more topics in a more hand waving way. One thing that's quite tricky is pasting image material inside that layer. So the question was when I'm pasting like some of the techno people say well that's first of all a new layer or that goes in layer tree and I'm like oh no no no wait a minute. Especially because of the Trinity. We pay something that's just an operation you did on this layer and it becomes part of it. Of course it needs to be there on the stack. There's a little paste and needs to be on the stack because a year later you need to be able to revisit that and when you highlight that you may move the thing to another place and apply other operations on it. Talking about applying operations on your paste before you nail it down on the layer. That's something that I see the power of it and we really got to support it. That probably means that we need a little triangle there and a sublayer. It's really a sublayer of operations on the paste so we're going to get hierarchy inside the actual operations. So we will need something like that. This is similar to layer groups and going inside that this is similar to having vector layers and then having a bunch of them that can also be stacked so you need sublayer hierarchy inside it. Two more topics in a hand waving way. One of the difficult things that I got to know last year is the cloning bit. There's that bit of tree again and these guys here are called clone that we can just about read it. As Pippin described it, that's just something like it catches whatever comes in here in the input and teleports it to weigh somewhere else in the graph itself and if you change this bit it also changes in the sky above there. So really certainly in that direction from the master to the clone it works like that. Pretty quickly the solution for that was found to, when you got something copied then you can just literally paste it and get a copy of it. You can also paste as clone which will then turn up in quite a few of the menus to do things as a clone. But that's only the start of it because I think yeah, he just wants to have this funnel and teleport it to somewhere else. I can think of more things you can paste as a clone. You can just take a layer and paste it as a clone. You can clone layer and then one in the same thing. I can take a group of operators in my operators dialogue and paste them as a clone somewhere else and if you change them on either side the other ones change too. So you got an eternally chained set of operators of the same thing. Still the discussion of this clone should be just like linking hard or soft cloning if there should be a master and then slave relationship or there should be really hard cloning all the same thing. You change one, you always change another one. So this is where the mind boggles and that's something TBD. Finally, just to send you off with another thing that's quite intriguing. When we got all that gaggle built into GIMP and you saw the operation stack then the last dogma of today will be that you still will be able to use GIMP like this without the gaggle stack at all. If you're not interested in turning operations on and off, reordering them or revisiting the path and changing them then GIMP will work really fully for you and mostly like it was in the past. There are other changes but it will begin just like you knew it with working on layers, doing the operations, using the toolbox to do stuff or things from the menu. So this is a dogma that's also going to be pulled through to the design phase that at the end you're not dependent on the gaggle dialogue or the operation dialogue to get your stuff done if you're still just in a linear way want to get stuff done, exported and get out of there. So with that, I leave you for today. Thank you. We have space for one question and the rest we will need to discuss in the break. Anyone has a question? Yes. I'm sorry, you need to... Not all at once. And maybe you want to move into the front? Because otherwise we're blocking the entry. So please, there's seats enough here. Can you move, please? I'm just wondering, you know, with all the gaggle operations there, are you going to have some sort of cataloging or tags or how do you know that something you used two years ago, what it did, or, you know, rather than sort of just going in there and fiddling with the machinery of the operations, how do you remember what a series... Because you may have much more than four or five operations, right? Cool. Given image. Well, first of all, let me stress that really the operations that you saw, the operations you should be able to fit in are just the same stuff you see right now. Just all your filters will be called as the filters are, all your modes of applying stuff, all the compositing will be called as it is right now, as it is recognized by the whole graphics community. So it's simply a prerequisite that when you're operating GIMP, you know the tool. You mastered it, you put in your couple of years of working with it to get to that level where you're working really well. So your question, how do you recognize those operators really scales in the same way with how do I recognize to do my next step? What do I need to do to get the next thing done? So that same mechanism of this name stands for this kind of effect that gives you... That is used to recognize the old stuff or to plan how to do the next thing. If you look at your old operators and what I showed you was, you click on them, you get your old parameters. So you take it from there, from the point where you were and you pick up from there to adjust it in the direction that you want to take now. So that's... Yeah, that's just building on the same mechanism as before. You have to know what you're doing, you have to know what Gaussian blur does for you to pick it also from that stack of operations to know like, I need to adjust my blur because it's just not right and I thought it could be a little bit more, a little bit less or a bit more edgy or whatever. So it is also at the end, it is a tool for masters and you simply got to learn and know how to get your graphics done with the same set of operators that you know from last year and it will be there in five years time too. They will be able to adjust on that list of things you've done. Thank you very much.
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The (eternally) imminent integration of GEGL into GIMP—or rather, fully basing GIMP on GEGL—holds great promise. Lossless editing and unlimited re-adjustment and reordering of image editing steps are only the beginning. However there is big gap between the nuts and bolts of the GEGL graph and nodes, and the world of GIMP users doing high-end image manipulation for artistic results. User interfaces bridge this gap and Peter Sikking, principal Interaction Architect at m+mi works, and lead Interaction Architect of GIMP, will outline in this talk the UI principles that can unlock the power of GEGL in a GIMP context.
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10.5446/21506 (DOI)
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Okay, before I start, thank you for inviting me and having me here. My name is Mirko Dubial-Schefer. I'm a system professor at Utrecht University at the Department for New Media, and I recently finished a dissertation on Baselard culture, as I called it. It's about online collaboration and communities changing and not changing the culture industry. And today I'll be speaking about metaphors, technology, and media practices. And I saw that I was late, but what I hear about the lecture, my pretty says I was really great because my lecture will be just a footnote to it, I'm afraid. And I will explain how technology on several levels needs to be designed as a legal level, a level of practice, and so on. So if you're speaking of technology, we always dream of society. And that is not new. Innovation has been driven by motives to design a better tomorrow, starting with Chopin's optical telegraph, who desperately wanted to use a tool for introducing democracy to France, despite the fact that it then has been used for military purposes. Later on with Marconi's idea of a wireless world, we see a popular discourse referring to the wireless era as a state like socialism, like the socialist dream. And dreams like that go on. This is the opening slide of Xbox Linux that is also referring to a dream, telling the user that for the first time the box you paid for can do what you wanted to do as the owner you are, where you should be in control. But even more important, this opening slide is referring to something that is of a much deeper meaning. It tells the user that with Linux you can plug into a world of sharing and contributing. You can be part of a worldwide community where ideas and software are free. So telling the user you're not alone, you're there with other people, and there's a community like a warm, cozy feeling of people that are together with you in the same thing and striving for a better world and liberating the proprietary devices from the evil ownership of the corporation. So how do we speak about technology? Of course I like to refer to Wittgenstein, not only because it's cool, but because it's so to the point that he says, the Grenzen meiner Sprache bedeuten die Grenzen meiner Welt. So what I cannot speak of, I can't put into words. Another person who spoke about innovation and technological progress was MacLoon, who said that we look at the present through a rear view mirror, we march backwards into the future. Meaning that we have to explain all innovations and technological progress in images we can understand using associations and words referring to the past. So if innovation goes public, then new technologies require something I'd like to call storytelling. They need a story like a great legend. Only innovation that is communicated will diffuse and will be understood and will be picked up on. So it is often promoted in a popular discourse. The next type of, quite sure, be either cloud computing or augmented reality or both. And it will be promoted in a popular discourse where people tell us that the world will be better, that there will be social progress through technological advancement. And these popular discourses are constituting something that I call a rhetoric of progress to imagine future technologies, their uses and the benefits. And we might think that metaphors are just used innocently, but they are not neutral, they do something. So here's a couple of metaphors used to describe technology, technology to make something understandable, imaginable for someone who has no idea what to speak of, where the words are lacking. So the internet has been described as the information highway in German, die Datenautobahn, the worldwide web yet another metaphor or cyberspace, hypertext is a metaphor. The Mamex referring to Vennevar Bush's visionary text on a memory extender. And of course, the latest hype, the Web2Row, which is yet another metaphor to speak of and to describe something in terms which are actually not really appropriate. This was the first glance the common user had on the development of what back then was labeled the information highway. And you see how the metaphor tries to paint the picture of a street where information is carried on. It is not the first time that we use a metaphor as to describe technology. When the common public was unable to understand what a computer would do, the computer had been related to the brain. And it was sold as a thinking machine, which on the other hand, created quite some disturbance because people were afraid that machines could take over and could replace them. So metaphors matter, this is really an important thing. They are material, they are words that shape our understanding of technological design. And even more important, they evoke associations affecting the constitution. So what can we do with a metaphors? They represent utopian concepts. So in the metaphors we use, we describe already the future use of technologies. An example, I turn to an old example. So we are familiar with both terms and we see the information highway described by Elgore as we are on the verge of a revolution. That is just as profound as the change in the economy that came as the industrial revolution. And then he goes on to speak about the glorious future when everybody, due to the new networks, will have access to commercial marketplaces, will overcome geographical or physical distances due to these new streets. Other metaphor, the cyberspace, much more wider, much more anarchic, much more sexy. So here we have Perry Barlow, not his, of course he comes from other side than Elgore. And he says that the governments are not welcome in this new space. He's opening up a completely new concept, not a street, not a highway that is governed by a bureaucracy, but a new anarchic open space where everything might be possible and where we can start over again. It is also just a metaphor, but the concepts and even the design concepts evolving around the different metaphors are completely different and refer to completely different concepts and political ideas. So a rhetoric of progress idealizes media and the ways to use them. And that is why it is important to pick good metaphors to deconstruct the bad ones, the ones that are inappropriate or are misconfusing. The rhetoric of progress always employs recognizable images. So it would be difficult to come up with a completely new metaphor that is incomprehensible for the majority of the users. One company which did that really in a fine way was Cisco Systems by explaining everybody that access will be, access to the new information highways will be the vote to commercial success and wealth. The key elements of the Cisco Systems advertising campaigns, which were, by the way, targeted not at their end consumers, but at the large majority of the population and not to their potential clients, were emphasizing access and participation due to the new technologies. And from there, the development of new business opportunities, the global connectivity and a great market of happy people. So you see that here, this unfortunately even made by a German advertising company with the stupid slogan, one world, one game, one internet, that reminds of a really disturbing political time in Germany. But let's move on. So in the first part of the development of the World Wide Web, there was access, the key metaphor for participation. If you have access, you can participate. Today, it's collaboration. It's not the dream of access because access seems to be something we have achieved. Now it's collaboration. And participation became the great legend of social interaction and cultural production online. It's telling a rather simple story where the passive consumer evolves through being a critical reader to a user into becoming a consumer producer, sorry, which is laid out in the popular discourse and is quite inappropriate. It is emphasizing, according to Jenkins' definition, the strong support that some participant of the community would find. The belief members have that their contributions matter, the social connection with one another. Okay, that is all valid and you will find that in many communities. But it is always based on intrinsic motivation, explicit activities, it is community or team-driven. There's another form of participation, implicit participation, which I will describe in a minute. What we find here, what I try to do was laying out all the media practices that have developed over the past 20 years. And I try to organize them according to accumulation, which means you try to do something with the content already provided by the media industry and you mod it, like the four-store net, or modern Star Wars. You build completely new stuff, I call that construction, and you are busy with organizing data, which I call archiving. We have many projects that are driven on the key aspects that Jenkins is pointing out. I skip that, it just means that the product you put on the market will change, like an Xbox will change into a Linux computer. But let's go on to the more interesting part. There's great, Nebster did not only provide music, it also made something extremely clear. It was built from already existing technologies like Fire Transfer Protocols, MPEC Forman, music player applications, and programmed for automatic indexing. But what it did was changing distribution by good, for good, by lowering the level of participation. You don't have to be nice to your neighbor just because you wanna borrow a CD and copy it. You just plug into a network, you don't have to talk to anybody. You circumvent all the community aspects that are so much highlighted in the discourse on participation. It is just on a low level. You still participate, but it's implicit. It's part of the technology, of the software design, and so your participative effort in communicating with others goes away and you have a really effective way of exchanging music. Somebody else was not happy with that. Actually, that was good for the design. Companies like Overpeer and Media Century were trying to flood those networks and to fight the distribution online. That only led to better protocols. So the participation of the evil empire was actually good for the development of better software. What did we learn from that? The interplay of design and appropriation, that means what users do with the technology that comes out there, is actually really important for the innovation of the overall technologies. Napster showed us that participation can take place on a low level. So the intrinsic motivation can be bypassed, which is really cool and which really works in the web2o applications that we see at the moment. And you can automatize participation, which is even more important. And we see that very well done by the culture industry in the current hype around web2o that is completely thriving on a promise, and it's nothing more than a promise that everybody becomes a producer and can participate in the culture industry. So what actually took place was that the culture industry found a way to extend into the domain of the users and implement their media practices, like building websites, blogger.com now, like communicating with each other, like making videos and uploading them YouTube now, or I think the boldest example are file hosting services like Mega Upload that are actually completely thriving on pirated content and building successfully a business model around it. This is what I call implicit participation. It means that the software design is directing user activities. It is formalizing them in the software design, something that has been dubbed by Timor-Waley as architecture of participation, and which is now by some critics labeled as architecture of exploitation. And they developed new business models, many of them do not deliver revenues yet. The most important, that took a shift place from content creation to providing a platform, and that is the important point. It's about these platforms. I don't mind that Facebook might make money with my content on it, with me communicating with my others, but the problem is that they are determining the platform. They are determining the cultural and social values that are laid out there, something that you find in the end user license agreement, something that might apply to force as well, as you have seen in the previous lecture. So what's labeled as participatory culture right now is actually something that reminds more of a football stadium, where you are a participant among thousands of others, and the platform, the stadium, the arena, belongs to someone else, and they are determining the rules. And that's why technology, the technological design is the key to cultural powers, and Rufinberg, a philosopher of technology label. This is why it is so important that we put together a technology that makes sense, a design that is laid out on the level of the metaphor, the media practice, and the technological design. It has to be embedded in that, and if the technological design is contradicting the metaphor used, then companies have the problem that users will hack it, like the black Xbox, that has been hacked by users because it wasn't, it was limited to a game console, but behind the black part was of course a powerful universal machine, and the downgrading, the metaphorical downgrading to a black box was something that was easy to remove. I find it really funny that actually the development, of the development kit of the Xbox is a transparent box, so the developers receive the transparent Xbox, and I find that from a metaphorical point of view, hilarious. So here we see a contradiction between metaphor and technology, and I find it very important for designers to think about, for designers of graphic design or technological design, to think about the way how technologies are communicated and how the metaphors to describe them might be comprehensible to the future users, and to what extent those metaphors describe the real users and the potential of the technology you're offering. Because in the end, referring, and I'm almost done, referring to the German philosopher Walter Benjamin, it matters that you build devices that change the entire apparatus of production by making them available to the most possible number of users, and that is what my predecessor has perfectly well described with the freedoms for force and which applies here as well. Well, thank you very much. That was a speed reading because I thought I had 30 minutes to speak. This lecture is based on an article which you can find in the recently published book which I co-edited with my colleagues, and which is, of course, for download online for free and redistribution. Thank you very much. Thank you.
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Making the world a better place has been a powerful engine of ingenuity and has driven technological development from Claude Chappe’s signalling system to Samuel Morse’s telegraph, from Paul Otlet’s information indexes to Ted Nelson’s hyperspace. Information technology in general and the World Wide Web and its label Web 2.0 in particular tell a legend of empowering users and enabling participation.
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10.5446/21507 (DOI)
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So we are Martin and Niko from Fedora team and want to share from our experience with working with the tools we are all about here. Yeah, so let's start it up. Who are we? We were founded in the April at the year six of the new century. Then what matters is that it was around the sixth 30s of our operating system. We started as a art team, but we rebranded later as a design team as our portfolio get wider and wider. Our current team leader is Maureen Duffey. She's a really great artist and leads us very well. And we all appreciate the work she's doing for us, even though she is employed in Red Hat for different things. We strongly believe in Fedora's firm foundations, which are freedom, friends, features, and first. You can see we are friends. And you can maybe see that we also promote freedom in our design team. And the starters were not exactly easy. And you can see that we were established around Fedora 8. And Nick will talk something about why not in Fedora's own. First, I want to say a bit about rebranding. We started as an art team, but the idea is we don't want only artists, but designers in general for user interface or usability. And we don't want to scare them away from our team. That was the purpose of the rebranding. Our first lesson we learned was about Fedora 7, when we had a professional designer working at Red Hat, who was in charge of the look of the distribution. She had this team named Flying High. And she was treating all the process like voodoo, like normal people can't understand what the designer do. We as a new team were somehow offended by this, because we believe design is accessible to people. And we believe a community should do this in the open, not like voodoo. The result was a pretty picture, but the community in general agreed with the idea. We like the result, but not the process. This was one of the big step in the opening of Fedora, not only the software, but the community in general. Yes. So here's the portfolio we do. We started at the beginning with just a distro artwork, which is wallpapers, some banners to our installator, and splashes for the login managers, and something like that. But we also, as the time went, expanded to doing website graphics from design of the layout of the webpages to banners and icons for various websites. We also produced marketing and release materials, like CD and DVD sleeves, some posters, t-shirts. You can see one on NICU. We provide also some design service. People can ask us for a certain design they like to have, like icons or logos or Hacker Gocci for their blocks and so on. We also provide usability and interface design. And some of us do also some site projects, like EchoEcon team or comics, photography, and more. With this last release of Fedora, we also started making a Fedora design suite, which is a spin of Fedora. It is a compilation of tools that we think that are very good for artists to work with. And we plan to expand it even more so that we can work nicely just with the contents of the design suite, which is on the live DVD. And of course, we want to have fun and do cool stuff and be friends. No, a bit about the tools we use. We are crazy about Inkscape. We are one of the biggest fans of this application. Yeah. We also use GIMP a lot. I believe everyone in the team know how to use GIMP. We also use Kribus mostly for printing, for preparing printing materials. I believe also this design for the t-shirt was finished in Skribus, not by me. So I believe it. With Blender, we have a few people clowning some, not enough. But we have hopes we will develop the skills. There is here in the room our colleague Pierreos who wants to learn more Blender and do more Blender stuff. We also use unlike small tools like Agave. It's something small, but we also love it. We use the image magic and many others. There are also apps like MyPaint or Alchemy, which we haven't used for something real. But we like them, experiment with them. And one day we will have something made with them. Believing in openness, we still don't require people to use certain applications. So if someone in the team want to use Photoshop, we don't say, no, don't use Photoshop. We just try to encourage them to use free tools. Still, we do require the file formats to be open so we can collaborate on those documents. As a consequence, they can't work with proprietary tools. We are also proud because from Fedora 8 to Fedora 13 now, the graphics for the distributional are made totally using free tools. We are proud about this. And we think this is a way to showcase. We believe the free tools are worthy, are capable, are good for the use. Another lesson we learned, speaking about file formats, is the story of the icon set blue curve. I believe everybody heard about this. It was one of the first icon teams in Linux made with vector graphics years ago. At the time, Inkscape wasn't there. I believe it was at SodiPodi in early stages. So it wasn't possible to do vector graphics under Linux. It was made with Illustrator. We had the source files in Illustrator format. We have the icons with the RAF-ray license as GPL. But we couldn't use it because nothing in Linux world was able to open the files. Also, the blue curve was a one-man project without specification. After the author left the project, nobody knowing about the style. And so we had to abandon the team and trying alternatives. One of them being an icon set named Echo. Martin is working on it, who is still unofficial. It's like a pet project. So the lesson is you must have how to open the files. And you must have good lines for the icons. OK, so now let's move on to collaboration tools we use. Since the whole team is spread all over the world, we have contributors from India, from Japan, from South America, North America, Europe. I'm from Czech Republic, Niquiz from Romania. So we need some communication tools that enable us to communicate without worrying about the time zones. One of these is MailingGliss, which is our main communication channel. The discussions happen there. Important things happen there. It's the most important one. Then we have Wiki, where we document some things, like how we do things. There are our sources, usually, are there of the images we make, and that's like that. Also, we are trying to employ IRC. We're not very well established in that area, but we are trying to get better, especially the news that next week we're starting regular IRC sessions. So we'll see how it will work out. We also use the ticketing system, concretely, a track. That's used mostly for the design quests we have. We use shared storage. That's also relatively new. It's more convenient than Wiki for storing our sources. So we are transferring everything we've created there, and the new things are already there as well. Plus, all of us have our blocks, and we, of course, block about what we do, and the blocks are aggregated on the Fedora planet, and some of them are also in Fedora design planet. And not forget face-to-face meetings. But with this aid, I should acknowledge that those suck. They are far from perfect. So we have dreams. Our colleague, Morin, has developed a mock-up for something which might be a solution. It is a web application which could improve the communication. You can find more on this address. It's a project under heavy work, under development. Let's hope one day it will be faithful. So one of the things that we've polished for over the several releases we've been doing is the release artwork we are doing for Fedora. The starters were tough. The process wasn't very good enough, and we always been late with our work. And so we needed to change it. And the latest, what we have, is some kind of three rounds process. The first round is gathering concepts, some kind of brainstorming. We talk about what the art could look like, present some design concepts, and such thing. Then when first alpha version of Fedora is approaching, then we are selecting one of the concepts to go with, improving it a little bit, and more, and more, and more. And as we go to the final release, the design must be final, and we base everything on the final concept. One of our good things we try to do is release early, release often. Even if the art isn't perfect, it needs to be included in the distribution so that we can get much more feedback than just discussing it among ourselves on the list, or in IRC, or something. The ideal time for the artwork to be done is by beta, and some other tasks. Because some other tasks are waiting for it, like creating the release posters, and DVD sleeves, and such, which are based on the wallpaper and these things. The key is the cooperation. And from that, another lesson we learned the hard way. For, I don't know, Fedora 11, or 10, Fedora 10, we had four concepts for the release artwork. Yeah, it was neon, gears, invisible, solar. And the people behind them didn't want to let the gear away. It existed until the last moment, and it was impossible for us to reach one single team as the final team. And had to do what I hated to do and never want to do again. We had a vote. This side was the best. It was ugly with the flameworks, and so with people applying to the art team, as it was called by the time, only to be part of the vote and such. So no, never to that. Play, learn to step back for the greater good. Yeah. And another lesson at the same time was to learn to check the sources you are using for the graphics. When running the vote process, someone discovered the Katana images using stuck materials from a kill-bill poster. It was too late to do anything the vote was undergoing. The author was swearing no, is a photo made by B refusing to acknowledge anything until we showed proof. Luckily, this team wasn't the winner, but was the other one made by him, Solar, when we were suspicious, checked the files, and found a photo of a moon used as a mask for he wasn't able to produce a source. So we had to redo the graphics at the last minute, and there is only free and reliable resources. Finally, one thing that is hot now in our communities are discussion about using photography with photos of people. It's a clash about us believing in freedom and the rights of the people in the photos. Usually, people need to sign release forms, which impose some restrictions. And these aren't compatible with a free license like Creative Commons attributions or attribution share alike. And we didn't find a solution still thinking about it, how to have, at the same time, free license and the people with the image undamaged. And that was all. Thank you very much. We do again one question, because I think you deserve one. Wait a second. Is there someone else who wants to ask a question? In the back, there. Ricardo, can you come to the front? First of all, really great stuff that you had there. Thank you for showing us. I was actually curious about how do you manage the design process once you want to design, for instance, an icon set? And you need to keep somewhat an identity. Does that actually come up spontaneously, or does that have to be decided in a kind of top-down process? I'm curious about that. For the icons, right now, we don't have a customized icon set. We used a missed and upstream icon set. For the set, we are developing in-house, Echo. Martin is in charge of it. And he had a developed set of guidelines. Maybe he can do more. The Echo icon team was originally based on work that was done by a former Red Hat employee, Diana Fung, if I recall correctly. The person with the voodoo. Yeah, the person with the voodoo. So we already had some styles. So we just needed to write the guidelines, summarize already the style that was already used, and follow with that. But the Echo project, as I said, is not used by default. For now, it's just an upstream project, which at some point may get into Fedora. Thank you very much. Thank you.
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The Fedora Design Team is an Open Community consisting from people from all around the world collaborating on various projects, from desktop wallpapers to posters, icons, website and application mockups, CD/DVD art and more. Everything created by the team is licensed freely, according with Fedora’s foundations: Freedom, Friends, Features, First.
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10.5446/21508 (DOI)
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My name is Kywe Berman. I'm developing open source color management system. And as part of last year's GoGlozama of Code Project, we concentrated much on device color profile configuration in this color management library, or iranus. The device color management is a critical point to get colors right from one device to another device. You, as a designer, have targets like creating a, creating an impression to your audience. So I made some small moments. You want to have this impression in a predictable way, and like to share it with your audience. You want to share it with your users. Sometimes you create a design on screen, and don't can expect that people will have the same impression on their monitors and their screens, especially for internet and also for printing. You maybe want to work media-independent, and design your colors in a way which come out on different media with the same impression. And therefore, you need to create the same appearance on each device. Typical way to do this, or established way to do this, is to use ICC color profiles for communication, which can be attached to images and also to devices. Color profiles are small binary blobs, which contain color information like primaries of a device, or more advanced stuff like color tables and curves, including some text stuff for copyright and so on. So we had some years ago with the great promise to be well-served with sRGB as one fits all model. But if you use sRGB natively, like many operating systems do, and Linux does so, and I think Windows does also, by default, apply unaltered RGB values to monitor output, then you will quickly see that devices greatly differ. I have shown you on the bottom right and with the thinner lines two typical projections of color gamuts of color spaces. The inner one is sRGB ones. The outer one is Adobe RGB one, a commonly used color space by photographers. The other more irregularly shaped curves represent in the outer one a photo printer and the inner one a typical newspaper offset printing machine. So there are great differences. And we expect it to increase. Monitors go more nowadays towards greater gamuts. Wide gamut monitors is a common use term for this. And sRGB, which might have been standard in recent years, is superseded by this. And still we have laptops with much smaller gamuts. Target is for us to have these colors, the color appearance, meet each other and on each device. So the problems we face is that RGB minus one formula is a very pure result. And it is used in many printing systems. OK, good and good has some more advanced features, but it does not reach really precision. It has certain problems with blue colors and also in many other regions. And you get at the first impression a nice appearance and can be satisfied with this as a standalone thing. But if you compare to screen, if you compare to other media, we quite differ a lot. And so it's not this native color handling is not a way to go. Then devices have different properties where are configured by native configuration systems. And these systems have to be put in place and to be passed and understood by a color profile configuration framework. And also there's a variety of renderers like DCGOR or like Gutenprint with own options, which does not only apply to the devices, but also to the driver side of things. So different device IP I already mentioned. There is the Xanny AP. We have cups with currently used PBD system to configure these devices. Gutenprint has its own format used in GIMP and GIMP plug-in. Then there's the Camaroar decoding with DCR. And Xorg is one system and probably not the only one. So one problem with these systems is that we don't tell you much about color. You have many properties in the configuration to consider for these devices like image resolution and like differing algorithm and also kind of media and also the size of media. These are properties which I'm speaking here at the example of printing. And these properties are partitially targeting as color and some options do not. And we have to find a means to separate these properties which are relevant to color and which are not. Then there is one huge problem that these system like Xanny and cups are networked, also Xorg. And it's not easy to circumvent these networking capabilities by native, by own means of a network layer. Cups has many security issues and it would open a can of worms if we would implement this stuff ourselves. The last point here is vendors need to provide profiles or want to provide profiles for their devices. And they don't only have one device with possibly one media. We have a large variety of devices working in different modes and also working with different media. And if we get color profiles shipped for all these combinations and devices and media, then we will have lots of profiles. And depending on the quality of the profiles, this will nearly explode in the data which has to be provided to the desktop user. What we have are the PPD attributes for printing, the good and print settings I mentioned. Xanny options, this is a library and the tests, some options encoded in C structures. We have some more active properties we can use to gather information about camera models and so on. Edite property for monitor configuration, this is a piece of binary blob which is sent from the monitor over the wire to the computer. And we need to abstract this data to have something we can use independent of each special device. Then the ICC had accepted a special information tag which contains key value pairs. And this is very well fit to the task we have to get with. And it opens the door to store information about devices and about drivers into the ICC profile itself. So what is Orenas? The Orenas project is targeting at color management as a color management system on operating system level. So it's almost low level stuff. It provides a C AP to get access to the data and to the configuration and also to manipulate these settings by programs, language bindings we don't have yet. But it should be as internal design is mostly object orientated, there should be no problem to create bindings. It serves as an open ICC specification test that this group, open ICC is a place, email listing primarily and a place to discuss color management topics for Linux and open source systems. What is implemented is profile reading from the opens ICC profile paths. It supports the device dependent ICC profile and X specification and also manipulates profiles, including of course, reading special information about number of channels and names and text strings and so on for displaying, doing selection of profiles in a user interface. So object orientated internal structures of iron as form some almost a basic core part and most functionality is designed to be stored in external modules. So we have an API for loading C libraries which can be exchanged to also have scripting backends which is not done yet. Then there's a policy model which handles ICC related settings and enforces them in color rendering modules where device modules which are designed to support mentioned device libraries and systems and there are some types of image processing nodes which can be formed to direct it as a cyclic graph and which do already some color conversion and together with the policy model and the device modules they can perform and to end color transformations. And as part of this flexibility I have thought it's very important to also support flexible options and not only this, these options have to be presented to users and so one needs some means to display as well as the data in user interface layout including a translation. Icons are also planned and will coming soon. This is the image view of Overnos, a very small example application and it uses LCMS module, asks the monitor for its profile and what you see here is these are the options provided by the policy module. They are common for the color management modules. These are the nodes to color conversions and here on the bottom we have a special option for the LCMS module which implements these above stuff and adds one new option and you can put where in some special stuff which we would otherwise have trouble to identify and to support. The application doesn't know anything about these properties, about these layout and user interface, is all implemented in Overnos in a module. So rendering is done here as an example and FLTK but it's also possible to write a rendering for these options in QT and GTK and so on. So we can just apply. This monitor is too small, this resolution. Well, I don't get it now right. So normally you should see the effect of changing these options here. This stuff is serialized to XML, to Xform dialect. It's not exactly Xforms. Converted to Overnos, C structures and put back to the LCMS module. This is stuff which happens almost automatically. You don't have to care about in your application. Just switch these modules on and constructs the image processing graph and you are done with the stuff. So now we are switching to Janis Belias and he has done some of this stuff for actually writing modules, device detection modules for Overnos and he will talk now about Xeni and Vodicoding. We have to switch the slides now. What? Frank's screen, sorry. OK. Hello from me too. I'm going to speak to you a couple of minutes about my project last year, Google Summer of Code. My job was to make two modules. One for Sain and one for digital row images. OK. That is for all devices that can take input, like from images, scanners, DSLR cameras and any kind of device that LibSain supports or the Libro library can read. And create images. So this is an image that shows the architecture of all things. On the left you can see you can have a lot of cameras, like an icon, scanners with different lenses and different kind of settings. So you can read the row images with multiple ways. You can track them from your USB device or you can read them with LibZ Photo 2 from a Digicam or Fspot. So you can use one of those programs to read images. Now, when all this gets ready to production, you can use the Uranus framework for color management. It's going to be easy for a program to talk to Uranus directly. The Uranus core can talk to one of the back-ins, the row back-in, which talks directly to Libro. That reads the row image and also can take all the information from the XIF tags of the row image. So when you have calibrated every camera with every lens or every kind of settings you want and you have created a color profile for each kind of settings, you can use the Uranus to decide which profile you want to use. It can send it back to your program, Digicam or Fspot, which then can create on the right an image with the embedded profile. And Uranus, on the other hand, can talk to your monitor so you can see exactly what the image is and you can talk to your monitor so you can see exactly what you want with your colors. Sorry. The same happens for Libsane. That's the second modular row for Uranus. You can see on the bottom is the same framework. So the same back-in can talk directly to the same framework and can take all the hardware and software options and can understand these options so it can talk to the Uranus core and you can select with your scanning application which profile fits your current settings, your current settings on the printer and on your scanner and stuff. So this API currently is only written in C and you can only make C calls but we could extend it in the other languages, Python or C++ and stuff. There is a communication protocol for every application who wants to use the back-ins, the Uranus back-ins. It can send text strings like the device name and get the information it wants to get the correct color profiles. That's the current state of the models. The same model is functional right now. The row image model needs still some work. If you want to try and use them, there is a code from last year's Google Summer of Code project. So there is some example code for live scene and for the row image. So if you have calibrated your camera for color management, you can create a profile and you can use that with a live row to create a T-frame image within a better color profile from all your row images. Currently there are some unsolved problems. The worst part is the network part. We don't have a way to get color profiles from remote computers, but it is being worked on. So we need help from you. If you really want to use color profiles and color management, you can contact us if you use scanners, DSLR cameras, or any other equipment. We'd be very happy to help you and hear your ideas and stuff about how this year can become better. Thank you. Thank you. Thank you. Thank you. Thank you. Thank you. I want to finish with a small demonstration. How the stuff works for the... I can close it. How the stuff works for the desktop. I will show you... It's correct here. I've installed here some Color Manager module which implements a one-off setting in the KDE desktop. You see here the various settings are actually translated in German to this is the screen. I have here on the laptop. So maybe I need to refresh the stuff. It's actually using Compits to do color conversion in the... This should be the beamer. You can change the color conversions on the GPU. Now you can change the profile of this monitor and you will see the effect instantly. You can do crazy things like this test profile to have an understandable demonstration. But you can of course use other profiles up to such crazy things like making an LHB profile. It's one of your monitor. And SRGB would result in... Would result in a zero transform. Well, I think this could be the closing of this presentation. Thanks for your attention.
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Devices seldom agree about colours by default. RGB (Red/Green/Blue) colour spaces in digital or analog cameras are different from laptop and desktop monitors and those are different from inkjet printers, even if they do not only support a CMYK (Cyan/Magenta/Yellow/Key-Black) colour space. The talk gives an overview of how these diverging colours can be brought together by the configurable Oyranos Colour Management System on a system level. It will further discuss what is required by applications to make use of the provided ICC profile information.
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10.5446/21509 (DOI)
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Well, I'll start by telling you a little bit about myself. I'm Jasper van de Gronden. I realized that it wasn't on the slides, but you'll probably be able to find my name on the program. Generally, I work on the Inkscape code, mostly things related to rendering, the compositing filters, a little bit of path related stuff. And today, I'd like to talk to you about diffusion curves. I'm not entirely sure how many people know what they are, so I'll try to give a gentle introduction to the idea. Sorry, wrong computer. Well, of course, in the olden days, we didn't have color at all, so we had to stick to grayscale or even black and white or green and black or whatever. As you can see, color is a big improvement. It can really add something to your work. And as displays got better, also gradients were introduced and became very popular. I think probably 100% of the people here has used gradients at one point or another. Well, but of course, the normal linear or radial gradients can get a bit limited. So at some point, you may want to do some more fancy stuff. For example, if you want to have a gradient on an image like this where you want both sides to have a constant color and let it be interpolated in between. And you can apply some tricks and, well, it kind of works. But then you want to do some more serious work. And, well, basically you have a problem. You can do this manually or at least I think there might be some people that are able to do this manually. And this is more credit to them than to the software. So I want to talk to you about a technology that makes creating this kind of shading, complex shading, a little bit more, a little bit easier. Now, this is all, these are all the curves that you need to draw the previous image. And the only thing needed to shade it is the colors on these curves in combination with a kind of blur value also along the curve that can vary along the curve. So there are no meshes. You don't need to decide on a resolution for your gradient mesh. You don't need to do any complicated editing of large amounts of mesh nodes or anything. You can just draw the curves, apply colors to them and, well, get a nicely shaded image. Now, this was just to be clear, this wasn't my idea. If you want to see the original paper by Orson and some others, really written in 2008, if you go to the site that's linked in the program, for example, and also on the Wiki, it's a site on Inkscape's Wiki, there are links to more related papers for those interested. Well, how does the diffusion curve work, more or less? Here we have the two basic, well, properties of a curve. A curve can have colors defined on both its sides. So you can have a gradient of some colors on one side of the curve and another gradient on the other side. Those colors are diffused over the image. I'll get back to how that's done in a bit. And you also have a blur defined along the curve which defines how sharp the color transition is at that point of the curve. So instead of just having, always having a sharp transition between one color and the other, you can actually have a spatially varying blur of the colors along the edge. And as you look at, and once these two things are diffused, the color image is re-blurred to get something like this. And if you look closely, you'll notice that in the middle part of the curve, the color transition is much sharper than at the outer points. And as you can see, just as the blur value, well, is higher at the outer points and lower in the middle. And there is actually an application that allows you to draw these things. Unfortunately, it doesn't work on my notebook because it needs your GPU. But it's nice to play with if you have time. Again, then, right in the wrong computer. So how do you do this diffusion in practice? Well, basically, it's defined implicitly. So if you take the diffused image and you convolve it with this kernel, which some might know as Laplace kernel or whatever, which would be the discrete mathematical equivalent of the formula below for those who notice kind of mathematics. Well, if you would convolve it, then you would get an all-zero response, except for the boundary conditions. Well, this is a slight oversimplification because the boundary conditions, well, it's always tricky to take them into account properly. But the basic idea is just if you convolve the output image, the diffused image with this kernel, you should get an all-zero response and you have to take care of your boundaries in a good way. Well, there are lots of ways to solve this kind of problem. And most of the modern methods would be able to solve this very easily because it's, well, it's not a very difficult equation. It's, the result is very smooth, so you can use multi-scale algorithms or whatever. However, there are some different ways to do this. And it can be important to realize that in practice this is equivalent to minimizing the gradient magnitude. Yeah. So, this looks a bit more complicated. And basically what you, but in practice it can be easier to handle. So what you do, now again, it's more or less defined implicitly. And what you do is you define the gradient as the image convolved with this kernel plus, well, and that's for one component and the other component is the image convolved with another kernel. Well, I think edge detection. And then you, well, you just square both components and add them to get some positive value. And it turns out that if you work this out mathematically, this is, minimizing this is exactly equivalent to saying that the previous formula is, should be zero. And later on I'll show you why this is, can be important to realize. Even if one is there. So, now, one of the ways I think is actually one of the easiest ways and also one of the best ways to solve the original equation was followed by, well, actually some people I know, but at the time I didn't know that we're working on this from Austria. And the idea is, well, I've got a very smooth image. So for some areas it shouldn't matter that much how large my kernel actually is because, well, it's very smooth anyway. And you can make this mathematically precise to show that this intuition is indeed correct. And so their idea was, well, if I have a point represented by the, well, by the dots in this image, then I take the area around it. I draw the largest circle around it that doesn't include any boundaries. Well, then I should be able to just scale up my kernel locally to that size. So for example, for this middle point, I should be able to use a pretty large kernel. And for the other points, well, at least I should be able to use perhaps a larger kernel than I would otherwise use. And it turns out that doing it this way essentially gives you a very, very fastly converging algorithm. I think they need something like eight iterations or something. Incredibly fast. And it's also quite easy to implement. And again, they implemented on the GPU. So I haven't been able to test it myself on this notebook. But it would be relatively straightforward to program this on, well, just for a CPU as well. So if you do all this, you've implemented all of the numerics, then this is the output. Of course, this is scaled down a bit to fit, actually fit on the screen. It's, so the image is about a thousand by a thousand pixels and it's half a megabyte. So, well, what am I, why am I even interested in this? Because, well, I'm an Inkscape developer, so why would I care about the size of a raster image? Well, at a point, if we want to implement this in Inkscape and possibly the same would be true for some other applications, then you may want to have a fallback because you can't expect any renderer, for example, Firefox to just implement diffusion curves when you feel like it. And, well, one obvious way to implement a fallback would be to simply rasterize the diffusion curves to some suitable resolution. Of course, then the problem becomes what resolution should I choose? Is this a problem for printing, for example, may I need too large an image? Well, one of the positive things I found about a rasterized version is that, for example, PNG really, really likes diffusion curves because they're very, very smooth. In fact, they're so smooth, I half suspect that you could prove that it, that PNG does compress them very efficiently. And in practice, I have seen that it does compress them quite efficiently. I mean, there are some cases where you have just a triangle or something that it is significantly larger than a mesh-based solution. But other than that, it's not that bad actually. So, of course, you do have these results. I'm hoping that you can see what I mean, possibly. So, if you zoom in enough, then of course, at some point, you will still get, well, these ugly jaggies or whatever you would like to call them. Well, all, because of what I mentioned, these jaggies or anti-aliasing problems and also because I feared that a rasterized implementation might, well, be too large on simple drawings, which I now think might not be true. I had a look at factor-based, well, discretization of diffusion curves. And specifically, I looked at creating a triangle mesh to approximate the solution. And, well, here you can see an unsubdivided triangle mesh with a very simple boundary. So, only one color, not two colors on either side, just one color, because that was easier. And I used a constrained-alone triangulation to produce this result. It's actually has quite a few nodes, not that many triangles. It's kind of okay. But, well, of course, you need to subdivide it a bit more so you get a little bit more triangles. Well, okay. Thanks. Well, the nice thing about a triangle mesh is that it gets you, that it's quite easy to interpolate on a triangle. You get a linear function, which interpolates linearly on all sides, but also inside a triangle, you can describe it via a linear function like this. However, this means that the second derivative isn't, well, isn't very useful. It's just zero. But you could use the gradient-based definition I described earlier. And actually, this leads to a reasonable algorithm, which gives you a result like this. Now, again, I'm hoping you can see it. Well, actually, it looks nicer than on the screen. But this is in fact rendering by Batik. And what you may see is that it has some artifacts. Well, I am not entirely sure that it's entirely Batik's fault, but it's at least partially Batik's fault. So, for example, if you render it, this is rendered at a relatively high resolution to decrease the results. If you render this at, well, lower resolution, then you get to see a lot of lines. So, apparently, rendering two adjacent triangles so that their, well, their complements of each other, the sides are complementary, is quite hard. And that is a problem if you want to make a high quality, have a high quality result. Now, for the final part of the presentation, I'd like to also go a bit into the blur side of things. So, now I've talked mostly about diffusion, but you've also got this blur component of the, of the, of this method. And in the rational method, they just said, well, you can diffuse the blur values, then re-blur the image using some spatially varying blur algorithm. Well, to me, this seems like a bit of a waste. I mean, basically, you're doing more or less something like blurring, so, because you're diffusing the image. And then you're diffusing another image. And using these two images, you create another blurred image. So, well, you may want to do something about it. But first, I thought, well, let's stick to the original plan. Let's try to emulate, for example, a spatially varying blur. So, for example, if I use a vector-based discretization, so triangle mesh, I could imagine diffusing a triangle mesh for the colors, triangle mesh for the blur values, and then try to simulate a spatially varying blur using SVG filters, for example. Well, this is an example of how you might do that. And it is, in fact, optimized a bit to, well, give the best response possible using two Gaussian blurs. I'm trying to create a, well, linear interpolation between, I think, one with radius one and one with radius one and one with radius five. And I'm not sure if you can see it, but what you, the effect you get is that you get a really pronounced boundary effect. So, it's not very nice. Now, a more radical way to change blur, to handle blur that would also change the original method is to use the heat equation. Sorry for the formula. It turns out that mathematically, if you fill in the right values for beta and gamma, this is exactly equivalent to just a diffusion algorithm. But it's also a well-known fact that you can use this to implement a spatially varying blur. So my idea would be to, well, tweak the values in such a way that essentially you get a, you get diffusion away from the boundary and you get this spatially varying blur on the boundary. But there are a few gotchas. So, I had another idea. And that's basically very simple. If you don't have any blur across the boundary at all, then you just have this step response. If you have a blurred boundary, you get this more gradual transition. Now, what if I just say, well, at the color boundary, I want to fix the color to the average of the two colors and I also want to fix the derivative across the boundary. This is actually not that hard to do in practice. And it might actually, it might be enough to at least give the same kind of qualitative result. So this leads me to my last slide. Well, this is a work in progress. Anyone interested in this is invited to contact me. And, well, as you may have seen, rendering a triangle mesh is problematic. So I am now actually leaning towards the rest of our based fallback bit more. But if someone can convince me otherwise, I'd be glad to. Of course, UEE integration definitely has to be worked out. And also, how to represent this in a formula. I have a few ideas on that. And they are on the wiki. They're at a very early stage and I would welcome any discussion on that either during LGM or later. And of course, you can wonder, well, what if I have field shape? Can I do something interesting with that? And transparency, well, it would be nice to also be able to incorporate transparency into this method very, you know, well, nice way. Thank you for your attention. So we take again, thank you very much Jasper. And thank you David, who did a fantastic save. We take one question before we move on to the next talk. If people want to, in the meantime, come into, there's, yes. So I think you wrote to the SVG mailing list recently about this. Is that right? Or someone did? Someone recently wrote to the SVG mailing list about diffusion curves in SVG. I don't think I will, I did so recently, but perhaps a few months back. There was a, well, okay, there was a post a couple of weeks ago about, so this is something we're interested in putting in SVG. What, I had, we had questions about syntax, we had questions about how well is it animated and also questions about is this known to have patents on it, things like that. So basically you're asking about syntax, animation, and patents. Yeah. Well, as to syntax, I have some ideas on that. I think it might be best to discuss that in another medium, but yeah, I think it should be possible to define something for that. As to animation, I know that the people who did this originally have considered it and I think also their application in supports key framing, but I never played with that, so I don't know how well it works. But yeah, there is some idea, there are some ideas for that. And I guess it would be a matter of implementing it and seeing how well it plays out. As for patents, I wouldn't know. I haven't come across any. I don't know if there are any other people here that might be able to tell you something about that, but I wouldn't be. Thank you very much.
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Diffusion Curves are an exciting and flexible new primitive for creating images with smooth color transitions. However, the best method to display diffusion curves so far is to rasterize them, which is unsuitable for use with SVG for example. I will present the basic idea behind Diffusion Curves, an alternative interpretation and an approach to creating a purely vector based representation (discussion welcome).
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10.5446/21510 (DOI)
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So, hey, my name is Alexander Prokudin and it's actually my fourth time at LGM. So I figured out I might as well unstuck myself and Come here and stand in front of you and tell you about something because what the hell? So today I'm talking about dark table, which is a digital photography workflow application It's quite a new tool. So I think let's start with definition of What is actually workflow and why do we need it? In short workflow is how we get the job done so a digital photography workflow tool is how we get our digital photography job done right Okay, so This is quite new application the project started around January or February last year by a German prodigy called Johannes Hanika and and Just last winter. He was also joined by Henry Ikelson and Later Pascal de Bruin who was here yesterday, but missed this talk actually contributed a lot of improved mattresses for the cameras So what are the actually highlights of this application? So first of all as you got it, it's workflow tuned There are many many more things actually and about this application I could talk about it for hours But since it's a lightning talk, so I'm gonna keep it short and sweet so Haha, the other cool thing about dark table is that it's not eight bit per channel. It's not even 60 bit per channel It's 32 float per channel and works in lab color space It also and since a lab is not actually the best color space for every task and For every task we need to choose Colspasit suits best it also uses LCH with basically is lab in polar coordinates Which also means that Dark table is HDR ready from ground up It also and it's not just ready. It actually imports and export exports flow PFM images and export EXR images Another good thing is that well, you know the 20 work in high bit depth the the whole image start waiting in In Starts taking an insane amount of memory. So dark table operate works with meep maps So basically creates Square one thousand three hundred side large and works on it so It's not as slow as it could be Yeah There is yet another great thing about dark table. It's complete. It says a complete plug-in architecture for both light table and dark remotes And as for actually reusing our libraries, it's it relies on Libro, which is Libre-fied DCRO and Lens fun for fixing Lens distortions and of course it uses XEV2 for dealing with all the metadata so I Think let's start with dark table. Just a short demonstration Okay, so we so what you see here is Dark table it's just an excerpt of shots from a concert. So how you start working with a whole new session is the import then you go through it you rate it and You set some for example color labels like you do it in Lightroom if it's the image is ready if it's If it's in in between the processing because the sessions can be quite large Especially if you should be waiting like with some five-round guests and so on so Hey, these are not ready red labels or Or it could be marked green and then it's ready. So let's have a look at other stuff Like I said everything is completely plug-in basic it's a half all these fancy things color stack Tagging and so on it's very very basic but It works just like that. You just double-click Select something Double-click or not double-click never mind So like I said the workflow is Important because you need to drop to get your job done very fast so you can move to the other contract or to experiment and enhance your profile or just Go ahead and have some time with your family So The good thing is that you can copy all the development settings and pass them into other shirts So if you have like for example session letting go indoors and then outdoors you have different types of lighting and It's just it's all in just one session. So all you need is to process just one short go back Copy and pass to all the images we that much these development settings So let's go now. Let's go to the dark room mode Alright so What you see is basically all existing Oh, yeah So what you see is Well, not quite only so these are essential essential plugins Exposure white balance you have also white curve which depends on the device you use you can actually choose between profiles So you have here nicking like cannon yellows like Sony alpha like and so on Since since very recently dark table also have the sharpened plugin Enabled by default because a little bit of unsharp mass masking With small values usually does picture good so the other essential plugin Oh, so does essential plug in this is crop rotate you immediately notice that What it has is not just anything. What does it look like? See this small active zones Yes So this is actually the third application that uses the very same concept the first one being of course gimp And it's a concept developed by Peter seeking who is I hope is present here and Second application is who can the panoramas teacher? But you can get more than that How about Golden spiral triangles whatever this was actually part by another newly new contributor his name is Andre Kaminski So that's essential plugins, but there are advanced plugins like local contrast Yeah, there we have it it's based on the conscious limited adaptive histogram equalization algorithm Don't ask me what it is it what it is I'm just happy to use it in some cases because it makes very nice Contrast pictures especially when it comes to landscape. This is not a landscape all by it. Well, it depends on your point of view So it The good thing about dark table another good thing yet another good thing about dark table is that it relies on very modern scientific researches like for example edge avoiding have way bullets the last seagraph last year seagraph paper, which basically get is This nice thing that works on Luma and on chroma separately So you can sharpen it because the left part is larger features and the right part are smaller features very small features So you can in fact do things like orton effect And with just one spline Yeah, and this spline is actually used in other Plugging which is called color zones. I think I'll have to browse for example because I realized when I came to Brussels that I don't have that picture with me that that plug-in is actually Comes from original comes from blender So, yeah Let's find it and since we are talking about blender Whoa have bad some but as you see the background is somewhat I'm not sure about the quality about the projection, but the background Behind but some is actually bluish and it's not like fun So we pick a color Here's this plug-in a Little bit lost in the English version of the user interface, sorry Oh Never mind. Oh, yeah, there we have it. So you can Select color by different by Luma colonists or here and tweak various things So it's works in LCH call space like I said so what we do here is we basically pick the color of the background and lower lower the Colorness and what we get is But some stating out of the background. Yeah So there is number of different Plugins in the project because them artistic plugins like vignetting you can see it here actually It's split turning It's velvet and believe me our over is much better in lightroom because it has that many settings Not just one tiny God of slaughter And There is just one more plug-in I can mention though I probably won't like to because it's very low level thing called raw import So what you do here is choose them as a I can method or enabling hot pixels or enabling green equipolation so The last the very last thing since I've got about half a minute is Presets that's a very hot hot thing What you what you can do is basically Create presets that will automatically or not automatically apply to pictures with particular features so for example if you have for Giving focal range and blazing camera you can choose a particular preset for lens distortion or for particular exposure and So you can define a particular Denies and so on so the choices are unlimited. It's up to you what you do with the application So there are there are a couple of unfinished features. This is called transfer waking where you can and Get dark table to analyze one picture and apply the Color features to another picture and there is another feature in works by Henrik. It's remote capture So in the future of the plan is to ship the Plug-in team play it so you can basically create your own plugins It's already ready for the third party plugins, but it's they are not internationalized like in GIMP So that's basically it if you have any questions come up Thank you. Thank you. You
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State of the art digital photography workflow on Linux and how darktable finally makes it possible.
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10.5446/21512 (DOI)
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Yeah, just a very brief introduction. We are a very small research group located in Antwerp at St. Lucas in Art College, which is not very obvious that an art college develops software. Well, we think it's obvious, so we do think it's obvious, but I'll let Frederick and Tom tell you about it. They're both doing their doctorate in art, and they both will explain it a little bit more about our project, the main project of the experimental media group, Notebox. Okay, Frederick. Okay, so this one works? Yeah. So, hi, I'm Frederick. I'm both a programmer and a graphic designer, and I've been working with Tom for a long time now on Notebox and Notebox 2. So today will be a quick introduction to the program, and then some future things that we're going to do. I don't like using slides, so I'll be showing the application live in the flesh, so if anything goes wrong, I'll leave the computer. So what is Notebox? Notebox is this really simple application, or Notebox 1 is this really simple application where you type in code, and then on the other side you get some output. So this is the code, it's Python. You run it, well, not full screen, and you get some output. And the nice part about this is that because it's code, you can reproduce it and regenerate it and whatever. This is not new to you because you're all programmers or most of you are programmers, but for graphic designers this is pretty amazing because in the old days they could only do use Photoshop Illustrator to generate one static file that they directly manipulated, put stuff carefully on screen, and using code you can do much more with this. So we do some animation there as well. We can, one of the nice things about this is that it's rapid prototyping, so we can change the animation while it is running. For example, change the width and height, and that changes interactively the sort of behavior there and the speed and go back, go and generate. So that allows you to quickly generate stuff, and then if you're happy you can export this as a series of PDFs so that you can edit them in Illustrator or Inkscape or whatever you like, or as a QuickTime movie and then have that rendered there as well. This version I have to say is only available for Mac OS 10, so the Notebox one. But there is a port for Linux done by amongst others Ricardo La Fuente of Shubot and I think he talked about this yesterday. Yes, and also today. So the general concept is known, but the application of it is really interesting. So when you have a tool like this you can make stuff like fonts, you know, multiple master fonts. This is the standard Adobe created where you can variate between two extremes of a font, so generally between a light and a bold. But because these are points you can do whatever you like with it, so you can make a bolder than the bold, even so bold that it sort of flips and then get these letters or the other way around and then you get really light ones until they sort of flip in the other way so you get this one. So really nice. You can add some randomness there so it gets jiggly effect going. What's interesting about this approach is that you've now created your own features. There's no step into creating a core Notebox feature or your own feature. In fact, when we're developing Notebox, we're first developing a new feature inside of the interface and then later just copy and pasting it into the core. So there's no translation step. There's no, well, this is core and this is not core. It's all the same. So here, for example, we have a filter that nits letters together. And again, you could do this by hand but it would take a lot of time. And then if somebody says, well, you have to change this to something else, for example, Libre Graphics meeting or we want this in Dutch or French or English, well, you won't be doing that by hand. You will be doing this this way. So for some applications, and I'm not saying every application, but for some application, this approach makes a lot of sense because it allows you to really quickly iterate over the code that you're doing. So that solves a lot of production challenges that you have. For example, generating lots of stuff so you can generate multiple pages of the same variant or you can have some, the code do some things that you won't be doing normally because it's so tedious to do. For example, this logo, sort of like a spider crawling around the letter and then dragging it. And you can't really see it, but, well, it's, let's do another one. See if that's better. So yeah, it's a bit dark, but, well, let's see. And it still doesn't help a lot. So anyway, with the power of code, we can now change this to something else that won't work. There we go. So you can see that we now have the, the federal letters. And again, you could do this in illustrator, select all, do these things. But you can't do all these things. The fact that you can reproduce these steps is really important. And again, we're coming from a graphic designer background where this is not possible or very hard to do with classical Adobe Illustrator Photoshop tools because you can script, but it sort of forces you into this really complicated model of doing scripts where here drawing a rect is just typing rect. And what's interesting is that we have a lot of libraries on top of this, not just the core, but we have a lot of libraries that allow you, for example, to import stuff. So this is an SVG file drawn in illustrator by an artist. Then you can import this into Notebox. And here you see you can change the colors. And then you can grow, for example, hair on it. So you have this hair filter that grows other stuff on there. I won't be showing this slide because this takes a lot of time, obviously, to render, but it's really fun to send this to the printer and say, what, millions of lines? We're not used to that. So another nice thing, well, what you just saw were production challenges. One of the things we started thinking about a few years ago was, well, you can not just do production challenges. You can also make the computer work inside of the creative aspect of the software, not just the production part. And this is, first, some spielerais, some tests that we did. This is a modern art critic talking about work. So this situation expunges any residue of checks or position of post-war attitude and peculiarly oblique match or challenge. And if you're done reading this, I'll give you another one. So contemporary abstraction, this work seems truly articulate. And I expect all of you to understand this, of course. And the situation seems to signify the disparity. Now, this is where we've done this when we were still students and we sent this to our teachers saying, well, this explains our work. So would you mind reading it and then reacting on it? And we never got anything back for some reason. The funny part is that people don't dare to challenge you when you put text out like this. So I think that's the whole point here. What's nice about this approach is that we just generated English, as you saw. But you can generate any language. This is just a grammar file. So this is a language as well. This is programming language. So we thought to ourselves, well, why can't we write a grammar file that generates notebooks code? It doesn't have to make sense, but at least it gives something. So we added that to the software. It's called New With Code. And what that allows you to do, you just write some random garbage and then it executes it. And because it's a script, you can execute it multiple times. So that's a really cool approach to get started there. And we hear from students that they use it to sort of brainstorm when they don't know what they're doing, just sort of rendering some stuff and saying, well, I like this part, so I'm just copying and pasting this. Of course, this is the worst code that you could write by hand, but we're used to that with students as well, so we don't mind anymore. Asking them to do object-oriented design is just wasted, so we don't do that. And then we have a poetry generator as well. So this gets more into the topic of concept things. So this is about love, nervousness, so nervousness. These are pretty good, actually. Well, not this one. Let's see, maybe another one. No hatred. Fitness planner, punk rocker. I like this. I'm going to export it. Okay, sorry. But you can give any topic you like. And this uses ConceptNet, which is a database about words, or WordNet, I think, he uses behind the screen. So WordNet is a database where you have all these links to more generic versions of a word and more specific versions of a word, so a dog might be a chihuahua or an animal, which goes up and down, and uses this graph to traverse it to generate poetry and a subject. But to talk a bit more about this, we have a color generator, and I'll go through this click because we don't have that much time. But this one actually has a bit more intelligence. It generates a color palette based on a word. So if you give it the word Apple, then it generates a color palette for Apple. And this works. I mean, this is, and again, the colors are a bit off on screen, but you can see it says fresh green, red, a bit of hard green at the bottom. So it makes sense. And we can do this for any kind of fruit. And this is bananas or orange. We know that. But the interesting part is that it also works for more complex things, like, for example, emotions, jealousy. What would the color palette for jealousy be? And he also gets it right. And this is interesting. He gives intense yellow, intense green, intense red. These are the palette that is a bit harder to come by for graphic design students as well. But he manages it because he, this actually uses the internet. He does some Google searches on these words to find out which are the most relevant colors relating to a certain word. And for some reason, it works like magic. Well, in 80% of the cases, we have some interesting side effects of that is that, for example, we did a, we wanted to know what animals had color. So we asked what's the color for a panther. And we thought, well, we come back with black. But for some reason, he came back with pink. Which makes sense when you think about it. And it also made sense for us because we said, well, it scientifically doesn't, it isn't completely correct. But from a designer standpoint, this is really interesting because it allows us to see what, or hit a finger on what the central nervous system of the global internet communities, which is a lot of bullshit words for saying, we know what people like. And that is very interesting for a program. It allows you to not only generate some basic things, but also to be able to surprise us. And that's very interesting from a design standpoint. Now, to talk a bit more about content, I'll let Tom talk about the parser that we written inside of the system there. Can I use this one? Okay. So, as we can show, already, natural language processing is a side project. We're trying to create a set of tools, a set of open source libraries to things like mining data from the internet or coming up with creative associations between concepts. So, if you think of a word, then you have a representation in your brain just to summarize it. And that is the concept. So, if you have a word like tree, tree has lots of different meanings in different contexts. And this software is able to find different meanings or what is called scientifically the conceptual halo of a tree. So, you see that a tree is related to primates, monkeys that live in a tree, or that it has a property big and that Baltimore is also big and that a tree is green and LG are green as well. And this is interesting because this kind of data is not put in by hand. These are the things that are put in my hands. So, users have said that, for example, big is a property of tree. But then on a larger scale, you get inferred relations between things. And this kind of data we can use to come up with all kinds of creative brainstorm applications. For example, I can query the database of semantic relations inside notebooks. And I can, for example, say, well, what kind of objects are happy? And he has to think a little bit. Then when he's done thinking, he can say, well, a dog is happy and the sky is happy and the relationship is happy, well, not always. And the Duracell bunny is happy. But in the same way, I can query the system, what are properties of the concept happy? And happy is something good, it's something compliant, optimistic, positive, and so on and so on. The results at the end of the list, so those are things that aren't happy at all. So for some reason, fat is not happy. I would kindly disagree. But in the same way, I can ask the database for ranges of a concept. For example, if I ask, what are emotions? And the answer is anger, anxiety, disgust, and we fear. And then the most interesting thing is that I can combine all these different kinds of data sets, so clusters of things or ranges of things, into an analogy query. So where the software is trying to come up with metaphors or analogies, so creative things that we designers do as well. So for example, I can ask, what are deep emotions? And he has to think a little bit again. But then he will say, well, jealousy and sadness and envy is pretty deep. And things like joy, surprise, and glee are more superficial. And it works for any word. So I can ask, what are playful emotions? And then he says, well, glee, joy, jealousy. Well, I don't know about jealousy, but joy is definitely playful. To put it into a more concrete example, in the same way, I can ask, what are elegant fonts? I already know the answer. And then he says, well, dully and sauna are nice fonts. I would agree with that. But not all the conclusions of the software are correct, because this is about aesthetics, about art. So there is no right or wrong. There is just inspiration. And this is the kind of software that can give you more inspiration quickly. A more complex example are analogies. So I can query the system for the range of all animals, so birds, monkeys, I can query the system for a person, George W. Bush. And I can ask it, well, what kind of animal would George W. Bush be? And he's thinking now, he's thinking very hard. It won't be nice. Tension rises. Okay. So the answer is Bush is like a mosquito or an argali, which is kind of a mountain goat or a big horn, which is a goat as well, or a donkey, or a goat, or an albatross. So what happens behind the scenes is that he's looking at all of the properties of each animal. For example, a bunny is fluffy and sweet, and a mosquito is annoying and stinking. You can get a painful sting from it, or a mountain goat is stubborn. And then he looks at what people have said about George W. Bush, and they will say, well, George W. Bush is annoying or is stubborn. And then you get this interpolation between concepts where the conclusion arises. One more. So this suite of software, like I mentioned, includes all sorts of tools to mine the Internet, but not just for images or for words, but the kind of creative associations you would like. For example, here's a query that is looking through the Internet for phrases that contain is more important than... LS, it is not visible. I can't really do anything about it right now, but the idea is that we are looking at trends as well. We want a software suite that is able to monitor trends on the Internet and mingle that into the conclusion so that he would not only say, well, 10 years ago Bush might have been stubborn, but now he's a nice old grandpa. So the kind of time-related data as well. Yeah, but it's okay. I'm going to leave it back to you. So you can show a little bit about the notebook soon. So we give this software to students in workshops. And we learned, of course, that students are not programmers. They're not the same people. They have this different kind of brain, which is interesting, but also very difficult to teach them programming. So we thought about this long and hard, and we said, well, we have to give them something that allows them to replicate their steps to be able to have this generative approach to it without actually being able to program. So we came up, well, the idea is not new, but we used a node-based interface for doing graphic design. And what this does is instead of just being able to write the word rectangle, you can now just select it from the list of all nodes that are available. And now you have a rectangle, and you can have these parameters for the rectangle, so the X and Y parameter, the width and the height, the roundness, and the color. You can all set that. And you can, of course, change that directly on the screen. And this allows you to do a lot of things. One, you have still control over the direct manipulation of the thing, but you can also do a lot of the things that would normally only be reserved for standard scripting application, like copying a thing. So I can generate, let's say, 10 copies and say I want to translate these, and I want each one a bit rotated, maybe in a different direction here. So now I get these kind of shapes. And I can still go back to the original rectangle and start changing it, and it changes the whole composition of the thing here. So that gives a lot of, one, it's very instant, it's very direct, and that appeals to a lot of students. But it also provides a lot of opportunities for creating direct manipulation nodes. For example, I can make a text pod, so this is all vector-based, by the way. So I can create a text pod and then say I want new points based on this text pod distributed along the curve. So the old points look like this. Oh, no. The old points look like this. The new points are evenly distributed like this. And now I can say, now I want to snap these points to a grid. And what you get is you get instant pixel fonts. So it goes from this one, or no, this one. So this is the original letter, this is the pixel-based letter. And you can easily change that. You can drag around the X and Y coordinates and get instant type faces. And then, of course, change the underlying type to say times or something. And then now you have one that has serifs. So really cool. And there are some concepts that we, yes, I see. There are some concepts that we added. For example, one is copy stamping, where each copy can be something else. So this allows users to use expressions which are sort of like the up step to actual, to the actual coding a part. So now they allow us to sort of build on that. And we can sort these things. We can say, well, we want to sort them by X, for example, or randomly, or we want to shift them. And then we have this offset parameter that we can change. Or we can sort by proximity to a certain point. And then we can drag this point around. And of course, we can do that based on text, for example, as well. So now we have text that we can drag around or be able to change that. So that provides to be a really important concept for the students. And we like that. We also like them to be able to code. So one thing we did is we added this code window here, where you can see what the actual code is for Node. And this is prototype based, which means that you're only changing a copy or not changing the original. So I can put in some custom wiggle code that I've written beforehand here. And just paste it in, click reload. And now I have my own implementation there. And I can change, for example, the seed now uses this to rotate this thing. So that's really nice. But it's not about what we do with it. It's what students do with it. So these are actual students that use the program. One thing we learned is that they drive the program really to its limits. So it will be a bit slower from now on. Because one of the students, a Finnish student, used a list of all Finnish surnames and visualized those. Now he would be unable to do this using either code or illustrator. So this really gives him a unique approach to the software. So it's really interesting. And I have some other stuff we did, a data visualization workshop where we gave two days of Notebox lessons. And then two days they could do their own stuff. And we get some really interesting results about this. Again, this is without any code. So this guy made some analytics data from his site and used it to visualize. For example, how long people stay on their site defines the complexity of this foreign noise shape or this typefaces. We have some people visualizing bus hours. So if you can read this, you can see instantly if your bus is on time or not. Yeah, you have to adapt as well, of course. Some nice fly. These ones visualized Google Trends based on the search for porn on Google. These are the winter months. So you get that. And we have some squirrels here. And this actually, because they understood the name of the program was Notebox, so they made this nutty creature here. And it evolves. So they really had a slider in there that said the squirreliness. And they could change the squirreliness from no squirrel at all to ultimate squirrelie, which is this one. And I think that's really interesting because that's the slider that you won't find very rapidly in Illustrator. You can ask for that. Maybe it's in CS6, I don't know. But even if it's going to be there, you can never add more sliders. So it's a really interesting approach. So I will be finishing now. I'll show you a bit about the future. One thing that we do is now is we talk to the people of processing to actually be able to change the rendering layer of the whole thing to processing. So we're interested in doing that. So we can also put in processing scripts. And that allows us to have animation stuff like that. So here's a game that we're making using this approach where you can see that we have these parallax sliders. And again, this is fully node-based. So you can go to the Boyds, for example, which is the one you see on the back, and then change the number of Boyds today. You can get these really nasty. So I think that's all for us. Thanks. So there's someone wanting to ask a question. Okay, we take three. We start here. So I'd like to ask about the availability of the project. I see that it's running on Mac OS X. Is it multi-platform, perhaps? Yes. Good question. And I failed to mention this. So Notebox One is not. That only works on Mac. But as I said, there's an, there's Shubot, which you can use on Linux. But Notebox Two, it's available for Mac Windows and Linux. So it's cross-platform. Awesome. And I also hope that, like, all the examples that you're showing are part of the distribution. Or is it just a blank canvas? It's still pretty blank. But one of the things that we came here for is to get this dialogue going to, okay, how do you want to learn these tools? What are learning tools that you want to make available? Another thing that I might add, what I really would like to get out of this conference also for, personally for me, is to get some feedback about how we can integrate this into your workflow. So how you show the Inkscape terminal usage, how we could do this from Notebox so that you can also use this from the command line, build your script, and then have it export or whatever. So we really try to integrate this into this full stack of open source tools, not just have this isolated platform that you have to do everything in. So, yeah. Thank you. Another question in the back. No, no question. No one else? Yes. So I would like to know whether, for the generation part you showed, it generated a lot of code. If there is a possibility to say that, oh, I like this, generate another thousand pieces of this, and I would say which others I like, and it will improve like incrementally. Yeah, and that's actually a very interesting question. We have some projects that we've done around, because this is about evolution, right? It's the Darwinistic approach to code. We have some tools that do evolution-based design, so it has these things about, or knows about local optima and all these hierarchical fair competition generative strategies for doing rendering. But they're not integrated into the whole code part yet, so this is left as an exercise for the reader, I would say. But yeah, it would be interesting to see something like that and what comes out of it. So, I don't know. We haven't tried it yet. Last question there. Hello. So I'm a designer. I don't know big bit, and I'm very interested, because it's very cool, but where to start? Well, you start at beta.notebox.net, there you download the latest beta version, and you go through the documentation and you read it, and you start playing with it. No, it's really fun to get into. It might be a bit overwhelming, because you have a lot of notes there, but it's really fun. And if you have some feedback that says, well, I have trouble learning this or this concept, then please mail us. We're very available. So, and tell us where you went wrong. And we have people that work specifically on documentation and getting that right, because it's very important to get that part right as well. So, if you have some feedback there and say, well, how do I get started in this, or that wasn't entirely clear, please let us know. Thank you.
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NodeBox 2 is an open-source application that generates visual output based on programming code, a node-based interface or natural language (i.e. English.) In the user interface you connect nodes (building blocks) together to create interesting visuals. Nodes can be opened to examine or edit the (Python) source code. AI techniques allow the system to evaluate written text and transform it into nodes using analogy and conceptual association.
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10.5446/21513 (DOI)
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Hello. My name is Felipe. I've been working with Inkscape since 2007, but today I'm going to talk about another project that was started last year, which is GNU-Libre DWG. It's a library that is part of the GNU project to handle DWG files from AutoCAD, which is a proprietary secret file format, so it involves a lot of reverse engineering of file format. The background of this project is that in University of Sao Paulo, where I used to study engineering, I used to talk a lot about free software to the students and to the teachers and so on. And we decided to form a user group, which is called PolyGNU. Poly is a reference to the name of our school, which is Polytechnic School. So PolyGNU. And then the first project that we have done was to install free software on one of the laboratories where we were having our weekly meetings. So in this same laboratory, there were other projects happening, and most of them were related to civil engineering and architecture. So we knew that once new projects needed CAD, computer-aided design software, they would probably want to reinstall Windows and so on because of AutoCAD. So we wanted to provide a solution even before they requested that because we knew it would happen sooner or later. So the first project we did was trying to figure out what is the current state of free software CAD tools. So we listed everything we found in a table. This is not the complete table, but it looked like that with features we wanted. Sorry, that's in Portuguese, but I can translate something. But these are several features that we thought that people would want in CAD software. And these are some of the CAD software we found. There are more. These are just some of them. And one thing that we noticed is that absolutely all of the free software we found did not have support for DWG file format. So we decided to do something about it. By looking on the Internet for references to the file format, we figured out Open Design Alliance, which is a consortium of the competitors of Autodesk that they wanted to have interoperability with content created by AutoCAD users. So the DWG file format as a secret was a barrier to their participation in the market. So they decided to get together and reverse engineer the file format. So it was not us free software developers that reverse engineered that. It was the other proprietary CAD tools developers that decided to reverse engineer the file format. And they released a document, an unofficial specification of the file format. That is not perfect. There are some portions of the specification where they simply say, oh, here goes a value and we don't know what this means. And I just know it's an 8-bit value or 16-bit value or even strange things like fields that have a variable number of bits. So the DWG format is oriented at the bit level. So it's a bit stream, you go parsing. It's not necessarily aligned by boundaries. So there are some huge that are unknown, but this is a 180-page document. And then we found a free software library called LeapDWG, which was working based on this specification to implement DWG support in free software. Because these guys have released a proprietary library for them to use. Actually for anybody to use, but it's proprietary. So at the time it was free. I mean, gratis. You didn't have to pay. And nowadays it's not free as in freedom, but also not free as in free beer. And then this guy took that documentation and started implementing it. But there was two problems. It was one guy alone working on the project. And the other problem is, as you can see in this page, they have documentations in English, Portuguese, and Esperanto. But this guy, he decided to implement the library in C-language, but with comments and data structures and variables and everything else in Esperanto. So it was a little bit hard to understand his code. We thought that, well, that's very nice of him to be so in love with this romantic idea of a universal, not political biased language. But we need to have more developers. So we tried to not be unpolite, but we did fork. So we have forked and we, just to translate to English, but then he was covering 20% of the specification. 20% of what was written in the specification was implemented. And just for decoding routines, not encoding routines. So after we almost finished translating, because nowadays we still have some words in Esperanto and some parts of the code. But, well, almost everything is translated to English. But then we decided to continue the work. And then nowadays we have almost 100% of both encoding and decoding routines implemented, but not tested. So one thing that we need is to have a test suite with DWG files and so on. I'll talk about that later. Another thing that we figured out, but not at first, it took some time for us to discover, was that the Free Software Foundation had, do you know the high priority projects list? It's a list of projects that the Free Software Foundation considers a priority for the Free Software movement. Stuff like PDF and Flash Player and so on. So they have a list of, I think, 15 projects. And one of these projects was implement Free Software alternatives for the open DWG libraries, which are proprietary. So as this was one of the high priority projects, we decided to submit a form in order to become a part of the GNU project. So it was accepted. And now we are officially a GNU package. Our website is GNU.org slash software slash Libre DWG. And this year we are participating in the summer of code through the GNU project. So we have one student that is also Brazilian. I didn't mention him from Brazil. Okay, I'm from Brazil. And both developers are from Brazil. And this student is also from Brazil from the same school. Yeah, it's biased. And he's going to work on the DWG rights apart. We have the routines implemented, but we do not have testing. And decoding is easy because if you miss something, okay, you're just reading a portion of the data. But encoding must be perfect in order to other software understand it as not a corrupted file. So encoding is really harder. I think that's a generic statement about data formats. I think it's very common to be harder to implement encoding routines. And he's going to be working on that. But there's also some other guys from around the world that are participating in the project. And one thing that one of them is doing is test suite. This is some examples of files that we have opened and converted into SVG. DWG allows 3D stuff and lots of stuff that SVG does not support. But as I had a background in the inkscape development, so I was familiar with SVG. So in order to test the 2D primitives, I decided to implement a converter to this subset of what DWG is capable of representing. There are some bugs here. As you can see, the strings are not showing up properly. This is inkscape loading an SVG that was generated based on a DWG file. I have a PDF of this file that we have used as a reference to see how it should look like. I can show it here. This is the complete document rendered in a PDF. So these small views of the house is one of these. Several views from the top. We have some bugs here, but these bugs are in the SVG converter, not necessarily on the library. Because the DWG is focused only on parsing the file format, not really dealing with the semantics of the contents. This would be a second step for maybe a second library or the application can deal with it. Because it's good to separate things. It's really hard to parse this file format. So we're just loading our DWG file and initializing the values of data structures so that other libraries or applications can use it. In this case, the SVG converter is defining the default color of the strokes. It's blue by default. It's not what is reading from the file. It's simplified. There's lots of things that are not showing up here, but probably they are already loaded into the Cdata searchers. So I think it's obvious that my example, SVG converter, does not handle what the library has loaded. Because we have almost everything implemented already. So except for bugs, probably the information is there. It's just a matter of the application not using it still. Still not using it. There are some objects such as the 3D solid entity that have an embedded file format called SAT or SAP, which is saved as text or as binary. ACIS is the name of a computer-aided design kernel. This is a file format that they used to use in this kernel. DWG uses it to store the 3D modeling data. This is another proprietary non-documented format inside a proprietary undocumented format. It requires some secondary library also to handle it. DWG versions change from time to time. So there are some fields that are only in the newer versions. The 2007 version has a header that is encoded using read Solomon algorithm. But we do not know which are the initializing parameters for the algorithm. So it works as encryption. I think it's not intended to be encryption, but as we don't know the initial parameters, we have to guess all of them in order to figure out which ones are the parameters. So this is something we still do not handle properly. So the DWG file, the most recent format is 2010. We have no implementation of this version. We already handle files from R13, 14, 15, which is 2000 and 2004. In 2007, we can handle except for the headers. We are thinking about implementing Python bindings for the library because there are lots of free software CAD tools implemented in Python. We are working on a test treat. So the ideas we have is to write a lisp or VB script to run in AutoCAD to generate an XML file that represents the data structures of the loaded DWG file in AutoCAD. And then do the same in our application that uses our library to generate an equivalent XML and then compare this. We are thinking of using XML as an intermediate comparison means to see what's not properly loaded by our library nowadays. We also need samples of DWG files that we can freely distribute as a test treat. This file I'm showing here is one of our contributors. It's content from his paid work. So probably he cannot share it with the world. He has sent it by mail to me so that I can test it, but I cannot put it in a repository and share it with the world. So in order to automate, we would need people to provide us DWG samples and ideally complex files. We need to test it a lot and we need to figure out how 2010 format works. And this is our contact website in the GNU project, mailing list, and Juka is my nickname, Juka, and Pitanga is the other maintainer. Thank you. Questions? Thank you very much. We take two questions. Nice work. Really amazing. Do you consider that maybe your work has the right methods implementation? Maybe it's illegality in countries with software patents? I do not know of any patents on the DWG file and I do not want to know. But fuck. How do it? Another issue with the encoding routines is that some people told us that we should not support encoding, but I think we should. I do not like DWG format. It's a hell to parse and it's a totally obfuscated file format. The whole purpose of the DWG is a project to not be needed anymore. So we want to provide it just as a means for people to bring their stuff into free software and convert it to something safe and never use it anymore. So it's good to have the encoding routines because we know I am an idealistic person, but I am aware that the world is not changing immediately to something else. So we need to have a way for people to actually use free software and I think it's not fair to have, for example, in a hypothetical case where we have a free software implementation that is even better than the proprietary ones. And we just cannot move to it because there's locks based on file formats. So I think it's important just like Microsoft formats are supported in open ops and I think it's a really important thing to have both encoding and decoding support for their proprietary file formats. It's the same here. Thank you. Second question. Anyone there. I heard about DXF file format, which is a brother of DWG. How about this format? This format is already supported by lots of free software projects. It was one of the items in our table. As you can see, Archimedes can read it, Keycat can both read and write and la la la. So there is already support for it. It's less complicated to understand because it's a text based format. And it's not exactly equivalent, but it's a subset of the things that DWG can do. I cannot say which specific features one lacks because it's just something that my friend told me. So I believe that he said to me, I'm not sure he said to me that it's not equivalent. But the fact is that people have DWG files and people want to load and people don't want to be bothered about. It must be so easy as people wouldn't give up using free software because of this. So I think we should have both supported. Thank you very much.
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LibreDWG is a library to handle files in the DWG format used by AutoCAD. I will present a general overview of the history of the project, explaining how a group of students at the University of São Paulo developed a new and relevant free software library (listed in the FSF High Priority Projects List) and how it became approved as an official GNU package.
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10.5446/21514 (DOI)
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Bonjour, pour la francophone il n'y a pas de traduction aujourd'hui, je pense, mais quand il y a de questions sur le chose que je dis, on peut me demander après, je pense. En tout cas, I'm Erika, you maybe seen my talk a few days ago, here's another one. I teach designing for new media in the Hague. Well, actually, maybe I'm talking now from the perspective of graphic design, so not necessarily interaction design, more graphic design, which is maybe something a bit... interaction design is a newer feel, it's got a bit less defined, I don't really know yet what interaction design is going to be. And, well, it seems graphic design doesn't really yet know how to deal with new media that well, but I thought there's a lot of possibility, and from the other end, I guess there's a lot of possibility for the open source world to collaborate with designers. I also just heard some people say in the audience. Anyway, what I notice about when I look at not just open source software, but basically most software and most interfaces, either on the web or on the desktop, their aesthetic seems to be sort of, I say, impoverished because it's always kind of narrow, like there's this huge pluriformity in the aesthetics of how we design for print, and the kinds of visual expressions we have, and it doesn't seem to be quite as pluriform yet in digital space. And, of course, the digital space is where we're spending more and more of our time, so it makes sense for that to be kind of awesome as well. Like, yeah, what I said, there's not that many companies employing professional designers, so when these companies do so, actually their decisions have sort of a completely disproportionate effect. Like, some guy at Apple at some certain point decided, you know, it would be really cool if we just got these kind of wavy lines, which, I mean, fair enough for him, but, you know, when we're looking at the avant-garde of software development, like 11 different Linux distributions, they kind of took up on that lead, you see it's even all the same color. Like, this is kind of painful, I think. Like Rebel, Rebel Linux, pretty rebellious, I don't know. And these ones, are they taken in a new direction, they changed the color? I think there even was a, oh no, I don't think I had the Arch Linux one, which was supposed to be very minimalistic, but they still have this background damage, I don't know. Like, another example, like, how would you represent a user? Well, some designer at Microsoft at some point had the idea, you know, it would be very good for a user, we just make sort of this ellipsoid shape, we cut it in half, and then we put like, spheroid shape on top, that would be a really good representation of a user. Well, it makes sense, but I mean, there's like, 5000 other possible representations of a user, but this particular representation of a user, well, it got traction as well. Look at all the different ways in which it's like popping up. This one I found the most similar, but we see that even, and that's one that's from the Launchpad site. And this is very funny, like, this is supposed to be super abstract, but you still see it's basically following the same model. And there we have, I think that's nice, there it's taken to a new extreme of basically modeling, like a sort of naturalistic image with the same kind of basic pattern. Yeah, but these are older pictures, maybe a year or two or three old, things that have been changing, companies have been putting more money into design, like Canonical is throwing huge amounts of dollars around. So, we've got this completely awesome redesign of the Ubuntu interface, which just came out. Oh, wait, what came out a few months before that? I didn't finish the sentence on the next slide, so I'll just say it. Personally, I feel free and open source software, it's hugely innovative. It's culturally relevant, it's like a catalyst for change. New methodologies are coming up, new ways of thinking about collaboration, workflow, property, new ways of dealing with the computer and the historicity of the computer. So, it's kind of not so cool when, in its look and feel, it's just like attempting to, it's basically like attempting to be like the classical proprietary software, because, well, I think that's what the guys from the media course in Rotterdam also said, it's not necessarily interesting for open source software to emulate proprietary software, but I feel like, in many cases, that's not at all what's happening. I think there's really exciting things happening in open source, but I feel like, I think they're mainly on the level of workflow and just like technological developments, like, for example, distributed versioning, what I talked about the earlier day, and I think in its aesthetics, it would be nice to sort of embrace more vanguard approach. Here are some elements which I find can be interesting when you think about the look and feel of both the software and associated branding, and things that are possible in open source and impossible in traditional software. So, try and compare this, maybe, with approaches in the graphic design field. Like, for one, I think certain quirkiness is a completely awesome thing. I think this is actually, it could well be my favorite logo ever, because this is for a program called New Pass Call. Oh, there's a new, there's Pass Call. Yeah. Well, when I saw this first, I'm like, okay, I'm loving this. I hope they're not going to redesign, you know? I'm looking at the new website, I don't think that's going to happen anytime soon, but I think this is some, we see an example of, like, a graphic approach coming up from the open source software world itself, which is interesting. Oh, yeah, this one I found also really cool. Like, you see a C++ book over there. So, this is also coming straight from the, yeah, from the Libra Movement, in a way. This is done with a Yatata, by the way, which is a Japanese kind of medieval pen. This is taking it maybe a step further, because here you see, maybe still, you could say, there's a certain, maybe, I don't know, I don't like the word, but maybe a certain naïveté in this approach. Like, I think it's really interesting, but as a designer, you have to take that a step further. You have to make more conscious decisions of employing certain visual strategies, otherwise you can never make, like, a coherent whole of a certain, yeah, brand, or product, or endeavor. I feel like the artist Y, I don't know if you've heard of the artist Y. He's already been taking that a step further, making a current aesthetic. He wrote a book about Ruby, and it's really cool, because it's like this cross between a comic book, a novel, and a programming manual. So, like, I recommend, I hardly recommend it to anyone who wants to learn programming. I haven't heard success stories yet, but I think, here you see, actually, quite consciously, applying his aesthetic quirkiness to the realm of computer software. And he actually disappeared of the internet, by the way, I don't know if you've heard that story. You should read John Ressig's blog post on that, a eulogy for why it's quite interesting. But here's something like, we can see in professional graphic design, a lot also, like, here's some pictures of a random mind. You see a lot in contemporary graphic design for, like, the last, like, 10 years or so. This combination of, this, like, sort of hand-drawn aesthetics. Oh, I should have put the website there. Lab-bong.com. And I think that's, for example, one, like, one thing you'll never find in corporate software. I don't think you'll find corporate software sporting these kinds of visual cues. Oh, yeah, candy-less-ness. You know, I don't know, but the whole idea of eye candy, I find that to be the biggest insult to visual professionals ever. Like, well, maybe about the same, like, separating style and content. I also find that to be, like, a huge insult. But eye candy, like, it sort of has this idea, like, okay, we have something, and we can smear something on top. Well, I guess I'm a modernist in that sense, that I don't really like that. But if I want you to take, like, oh, yeah, this is an example I'm going to give, of something which is good, so that you know. But because I don't want to get myself tart and fettered. If I want you to take anything home, it's like that candy is for children. You know? Like, well, maybe we're in a culture which is sporting a bit, like, like, could you say for hierlich, glorifying childishness to a certain extent. And maybe I'm just not catching on. Maybe I'm just like a old man, in that sense, a bit of a reactionary. Because, you know, also, I still find it, yeah, no, I'm not going to tell that, because I'm going to get tart and fettered when I say that. But, no, yeah, I think candylessness. Let me just give some examples of why open source software has some good cues, in that sense, like, the SVG format, we have the SVG working group around, I believe, to some extent. And I think, we actually also think, have the person around who drew this logo, but I'm not sure if he's here right now. SVG is, of course, really cool, because it's scalable, and it's factors, and factors are like, when they start, factors are quite candy less, because they're just basic shapes in basic colors. And I sort of like how this logo is for a vector design program, and then it quite emphasizes this technological aspect, also, in its design. So you see that abstraction of the snowy mountaintop is really quite abstract, angular shapes representing that. And actually, you'll find all this candyishness really requires, well, raster-based design, like pixel-based design, like, I'll come to that in a bit. I've seen a redesign of this, which makes this shiny. I think, I don't know if that's the current logo, but I thought that was like a perfect shame. Like, de-shine it, please. Yeah, here are some examples. Like, 20 years of progress, which is not that much progress. I actually calculated the amount of pixels used in each. I forgot, but this is like the brilliant design of Susan Carey. You should Google her. She's a really cool designer. She was solving this problem, like, we have 32 by 32 pixels. I mean, somehow, I need to represent the act of writing. And, well, I think, and we only have, like, two colors. I think she managed quite well. But then we see 20 years later, and now the pixel is 512 by 512 pixels, and they want to make it scalable. So there is inside this icon, there's a 512 by 512 pixels representation. There is a 128 pixels representation, 64 or 32 or the 16. They're all, like, combined together, and sort of the computer is actually actively, like, calculating its ass off just to get that there. I think it's ridiculous. I mean, you could have, that one scales, I think, even better. You could just, I mean, pixels are vectors, too. These are just, like, squares. You could put that up on your wall, like, blow it up to events proportions, and you'd still pretty well see what's going on. Like, if there's one thing I feel like missing from contemporary, you can, like, design aesthetics for the screen. It's, like, abstraction. Actually, you're the one to the left, which is the X-culc from the X window system. It just looks so much better. Anyway. Oh, yeah. You're more some, like, five minutes. A bottom-up examples of open source awesomeness. Because you see how well, actually, these really concrete shapes, like, these really abstract shapes of the pixels, are able to represent shapes. It's, like, from Anthony's Icon's library. Oh, yeah. And, like, of course, this is not graphic design. But this Matisse, and Matisse really shows quite nicely how to work with form and shape. I couldn't really, didn't have to find it to look out at, at it's nice to find out, to curate some of the best examples of his work, but Max Gissman is an example of a designer who works with these kind of simple shapes. Actually, he was quite innovative on a technological level, also, in the 1990s. Scriptability, like, I don't have any examples, but that's something else where open source shines. And we've seen, like, also the guys from the new media program explicitly said, like, there's a lot of that going on in contemporary graphic design. Like, the guys from LUST who are also here, of course, this, and, well, we've seen a lot of nice examples of that this week, for example, a Notebox presentation. Then, well, I have this, I have this sort of beautiful presentation on visual literacy, but I don't actually know, if you have the five minutes that we have the time to go through that. So, I'll just give two examples. Like, actually, when there are photographs of child labor, you'll find people actually looking sad, always, on the pictures. But if you look at actual reportages on child labor, the kids smile on most of them, because that's what you do when a professional photographer comes and takes a picture of you. That's maybe, like, an unrelated note, but it's not completely unrelated, because I think visual professionals have this way of dealing with our cultural heritage from a visual perspective. And with open source, I think, is one part of the equation, like open source tools. And then we have open standards, which are, of course, completely important. We have the public domain in the sense of our visual public domain also. But we don't have time for this, so I'll just go through it really quickly. For example, you'll find many pictures of Hitler's mind, oh shit, Godwin's law. Most pictures of Hitler in archives are actually quite happy. Mark Twain looks like a complete rock star when you go through archives. Yeah, I messed this up, of course, with Contemporary Magazine. Like, you know, that's kind of a very, that looks kind of totally ironic, because we've come to associate these shapes with irony, but it's not ironic at all. It's just meant to praise the Lord. And there you see, like, one of Helvetica's predecessors, and you see the whimsicalness, and I think it's really cool because this letter started out whimsical, like it didn't start out neutral. So that's something I think which designers can also bring. And then, the last part, which I guess is most important for this gathering here, why are we not seeing too much interaction between the world of graphic designers, visual artists, art schools, and the world of open source design? Ah, well, I think we spoke about that earlier, that it's really a matter of, well, a sense of cultural differences, and this difference between science and the humanities still lingering on in a mainly social sense, one minute. I really feel, I agree with the organizers of this event, that education is very important in this respect. And, well, to me it's really important that in education we start to take also, well, computer science seriously in the sense that I think programming is really not that hard, and I was speaking yesterday with, oh shit, now I forgot your name, from the post script team, and he said, well, it's not like everybody likes to drive, but you need your driver's license in order to get from A to B. I think it's a bit like that, programming is not always fun, it's a bit hard, but it's very essential to how our world works nowadays, and my personal experience is that, it's mainly people are very scared of getting into code, but if you just sort of throw them in, and they have another goal of something they want to achieve, they have content they are busy with, then actually, like, it becomes total fun, in like, well, I guess, three and a half hours. So, really, it's about prejudice, I guess, maybe on both sides of the equation, I can't speak for the other side of the equation, but I really feel that it's here, in these practical applications, because design, of course, is a very practical application of art and computer programming, is a very practical implementation of science, that it's here that these two things can start to blend and get together, more so than in any academic setting. Well, then we go to the discussion, like, what I'm interested in is, maybe is there some way, because there's so many open source projects, so that you could actually even find one, which is sort of connected to what you're busy with, at any given point, like, oh shit, I'm not really busy with these kind of images from the public domain, or if this fascination I'm working with, maybe there's some kind of open source project that I can collaborate with, which would suit this in its look and feel, or aesthetic, and I was thinking maybe it would be good to have something like a platform, where software projects can get sort of hooked up with, like, visual designers, interaction designers, graphic designers, sort of a platform for the, something like that. Like a style guide, like a sort of, a sort of pluriforma style guide, where every open source project exposes the way they've been dealing with their visual and their interaction design, and then you can, and how they would like people to pitch in, and then you could jump in, something like that. Maybe I don't know if that's a good idea, I would like some feedback on that. So we don't have the long break today to discuss, but let's take two questions or responses to this proposal. Anyone? Where open source projects could somehow find design, sort of a, software design data. Going back to your earlier points about design of icons in distros and so forth, I'm wondering what it would be like to live in your country, where in each town, there's a different set of road signs, and when I drive to another town, everything is completely unfamiliar, which is fine if one just lives in one town, might be a bit difficult if all the traffic lights are in black and white, but I'll ignore that problem for a moment. Is open source just about designing something that's really cool and interesting, or is it also about recruiting new people who are used to particular paradigms and are looking for something that is not too painful to migrate to? Well, that's a very good point. Like, this is always in any kind of design, like something where you have to actually take into account the fact that it has to communicate, so you're always making use of certain conventions. But I think there's a bit like, you have this curve for robots. When they don't resemble a human being at all, they're quite friendly, but at some point, when they're really close to a human being, they get completely scary. It feels like that for me sometimes with Linux, too, when it starts to really resemble the paradigms I'm really used to, but then all the small things, they're just different. That sort of gets on my nerves also, completely. So I think there, it's like, in a way, it's hard to keep up with whatever. A good example is the oxygen icons. I don't know if you guys know them, they're KDE set of icons. And then I was reading tango specifications, and they're saying don't make things shiny that are not shiny, like don't make pieces of paper shiny. Who the hell would they say that? Who would come up with the idea to make a piece of paper shiny? Yeah, apparently. You have the sticky note, which is like this yellow surface with a huge light effect emanating from it. And then I'm thinking, yeah, they're taking these paradigms, but they're not so good at utilizing them, and then the antistap becomes some kind of monstrosity. So I don't think that's a good. I think that's also an apparent danger. So I see where you're coming from, but I also see the other side. One more question. Personally, I think that the platform for meeting interaction designer and open source software is a very interesting thing. We are doing something similar now with Scribblz, outside of the project. We are talking to the project. But I see it as a very hard part, for what I've seen in the past. A designer comes to the project, he has cool ideas, he says, you should do this and this, and this is an example, and then the team says, yes, we have no time for it, we have other priorities. And the designer disappears. So the problem is how to get those designers to think, they bring a heart to do a job, they have thought long about it, and suddenly they think it's doable in a short time, if it isn't done in a short time, they disappear. So I think a hard part is to find an interface between the two words, with time in there. Time is very important, and both sides must be passionate afterwards. And this is something I feel very difficult, being passionate, waiting for something being there on both sides, and staying there, not going away. Yeah, well, yeah, I agree. This is a complete difference between the open source world and the rest of the world. Well, they also say, Ars Longa, Vita Brave is so in that sense, art is long and life is short. But I agree, and I think one way of dealing with that is to start with things that designers can actually implement themselves, so they don't have to wait on the implementation by the team. And this is, of course, well, the case with things like icons and stuff, which you can perfectly well make yourself. But I'm also, I find it interesting, for example, with fonts, and why you've seen a lot of font-related presentations these days, is because that's something designers have some kind of interface, too, they're kind of getting it, but that makes it easy for them to also get into the associated more easy for them, and more rewarding for them to also get into the associated technology, so that designers are actually sort of like, I learned Git so that I could work with this font project, for example. So I guess maybe it's about finding inroads, also, on both sides. I think that was the second question. So thank you very much....... OK. Oh. Il n'y a pas de mien. C'est bien de le savoir. Donc... On peut avoir deux plus questions, OK? Et puis, ce que nous allons faire, c'est que nous allons juste passer au programme, et voir où nous allons arriver, nous allons avoir juste un petit long de l'essence, et je peux... Il va se montrer un film. Je l'ai oublié, je l'ai oublié, je l'ai oublié complètement, parce que, vous savez, comment ça peut être possible que les designers sont maintenant ces gars avec le Macbook Pro qui sont en fait des... En fait, ce que le design est, c'est de s'y changer constamment. Des designers, le design, comme profession, est constamment réinventé en réponse à la développement technologique. Donc le développement de la printemps, le développement de la taux de la production, ou quelque chose. Donc, c'est seulement naturel que, à un moment, le design va réinventer en réponse sur les historiaux. southern Tooex type des c helping ont vu un petit fog-light comme l'adresse de bitte un peu en transmission. nous avons percroué Nine que ce ampl terrif s'est envoyé pourМы les étudiants, quand ils commencent, et après, quand ils finissent, leur éducation veut en faire du printé. Il y a un gars qui a écrit un livre qui s'appelle Print, il est mort. Il parle de l'avenir. On pourrait dire que si vous regardez la histoire du design graphique, c'est seulement logique que le design graphique à un moment réinventera en réponse à ces technologies de la technologie de la technologie dont vous êtes tous les instigators. Je l'ai oublié parce que je ne l'ai pas entendu. C'est une vidéo très courte. Je l'ai mis en place. Mais je ne l'ai pas entendu. Non. Oui, c'est bon. Il a l'air qu'il y avait Nouvelle Brody et que je l'ai oublié. Et la prochaine chose ne... Non, on va le faire. Parce que c'est seulement 12 secondes, donc je pense que vous pouvez voir le tout. On a l'air qu'il y avait Nouvelle Brody et que je l'ai oublié. Et la prochaine chose n'a pas eu lieu. Il y a tout de suite. C'est inévitable. Je ne pensais jamais que ce serait ce grand enjeu. Il y avait Nouvelle Brody et que je l'ai oublié. Et la prochaine chose n'a pas eu lieu. Il y a tout de suite. Mais je ne pensais jamais que ce serait ce grand enjeu. C'est comme ça.
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Graphic design as a discipline seems to be firmly focussed on print media, leaving designing for the screen to interaction and web designers. This is a shame. As we spend more time online, public space itself is becoming digital, and in this space the pluriformity of contemporary graphic design is sorely missed. In interface and web design, aesthetic decisions by a few major software developers have a disproportionate effect on the visual landscape.
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10.5446/21517 (DOI)
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Hello. Hopefully this will work. This will be a kind of a mixture of slides and demonstration. I hope it won't crash. Layed out is very rough at the moment, so it's half the time it'll crash. I can get what I want done, but we'll see. So I guess I'll just jump right in and talk about it. The easiest to use most adaptable user interface in the universe. So I speak, of course, of this, a blank piece of paper. This is kind of where I get my inspiration for how I'm attempting to design the interface for laid out, which is kind of a desktop publishing program that I wrote to basically help me make my cartoon books, which involves importing a ton of images and laying them out into various impositions. So let's see. So the pros of a blank piece of paper is that it's multi-contact. It's pressure-sensitive, color-managed, real-world brush dynamics, minimal tool clutter. Of course, that depends on what pens you've got in your pocket or whatever. But undo is only partially implemented, though. So it has those words to be done. So here's an example of what can be done just on paper. You don't necessarily need undo. I've been drawing all my life, and a lot of artists were just trained to do work just with pigments and stuff. The idea is just if you do something that you want to undo, you shouldn't have done it that way in the first place. I don't know. It's just a habit. You can see an example of pressure sensitivity and varying line widths depending on pressure. You can kind of see up there, I think. This is how I used to design or lay out cartoon books. So for instance, here's one book. This was done with laid out, but it's on legal-sized paper. It's just a ton of images laid out into a folded booklet. So before, I just draw little boxes. So the one in the top is the front cover, and then the next spread inside cover, first page, blah, blah, blah, all the way. So then I'd have to write in or draw in little thumbnails for each of the little cartoons that are on each page, which, as long as you stick to that maxim that you're only supposed to do it right the first time, it goes just great. But it doesn't always work that way. So if I want to rearrange, I can just do it that way, so if I want to rearrange cartoons or whatnot, then I'd have to erase the cartoons and draw them in the margin and figure out where it's going to go and then redraw them. That's kind of a pain. So I begin to look for solutions how to do this on the computer. Here's me in my natural environment with various books and such, the Stumptown Comics Fest in the United States. So generally, the process involved is you make content. For me, that's typically on paper that I scan it in. It's simple images. For the future, I want to be able to do more dynamic images. For instance, Scream is render frames. It's something that the program cannot automatically do, but something else can do it. It's convenient to just say to that other thing, do this, and then drag that thing in. Typically, my stuff is black and white, so I haven't really needed color management so much, but are there any Hugen developers here today? It's because of them that I haven't worked on laid out so much because I've been obsessed with making spherical panoramas. So I've got 100 panoramas that are all color. It would be nice to do something with color managed books or whatnot cutouts. So the next step for laying out is to lay them all out into spreads. The imposition is definitely something that's instrumental from the beginning of a project. It's not something that you just, or for me anyway, convert into. It's not something you do after the fact. It's something that determines page count and what goes next to each other. That's very important right from the beginning. Then once you have everything laid out, you want to print it out or to paper or sometimes to fabric. Because say you have a shirt that has strange scenes or something, the fashion thing, that's not a kind of need. Something laid out can do. Just thinking about impositions, how do you determine what page goes next to each other? Well, why stick to books? I mean, you can just make that any sort of, any polyhedra in any bizarre shape that you can imagine with things next to each other. That's, as far as I'm concerned, within the realm of laid out. Some people call it packaging. It's arbitrary polyhedral surfaces. There's other stuff that you can put in after that, like other flat-like gradients, lines, text, all that other stuff. I tend to draw all my texts, so it hasn't been a priority. When people ask me to do things, they always want text. And I always refer them to Scribes or I guess Scribes. Let's see. When I was trying to find other software to do these things, Scribes was OK for text, but not so great for lots of images. Anxigip was awesome with pass. You can do tons of stuff with it. Importing multiple images, like often I'll have 40 pages of cartoons or 100 pages of cartoons. And doing that is not so easy with anything else that I've found. Anxigip has no multi-page at the moment. Perhaps after SVG 1.2 gets finalized, perhaps that will become important. Potofluimpose and K-Princher and all that stuff, those are in position solutions after the fact. I don't know if anyone's seen EasyPose. It appeared a year or two ago and disappeared a year or two ago. But that way of doing in position seemed awesome, because you can just take one piece of paper and then fold it and then fold it again and fold it again. And the computer keeps track of how the pages will be arranged. So you just do all these folds on screen. It's very easy to do. So let's see if I can make this same work. Let's see. Oh, come on. It's there. It was there yesterday. Oh, there it is. All right. So this is just kind of a quick demonstration of how I would lay out a cartoon book. So I want to do a legal size paper and landscape as a booklet. You can put in margins if you want. I try as much as possible to make tools that everything happens on the canvas. So far, what does not do that is my image import, which is this huge cumbersome dialogue, but it sort of gets the job done. I'm working on a replacement to have some of the features of the InDesign Place tool so you can drag out things. But for me, the automated import is extremely important, because you don't want to do exactly the same sort of process for 40 images. It's better just to define sort of a template of where things are supposed to go on the page and then just dump in a whole bunch of stuff. So some of you might recognize that as the lobby to the Pantone Motel. Either that or this Chicago Airport. So now I've selected about 20 images, or so I can specify what DPI you want to import it as. There's options to select or import only a certain number per page, or you can do all the images as will fit on the page. So it will just kind of do it by rows, or you can slap them all into a single page. Eventually, there will be more options to lay them out in particular patterns and whatnot. But I'm working on it. There's only so much time, and I'd rather be drawing cartoons, but I do what I can. So that's a spherical panorama used done in Hugen. So some of these images are a little bit too big. And using a combination of mouse clicks and holding the control key down, I can scale it or if I do control and shift and then drag the mouse around, I can rotate it. There's also ways to shear it. It's hard to do while holding a microphone. And I just discovered. So these are all the spreads. Similar sort of thing. And then I just export it to whatever PDF or whatever is easiest to print at the moment. Then the export can go to a single PDF because that has multi-page, but say you wanna export all the page spreads into SVG, because maybe that's easier to manipulate for some reason, then you can do that also, except it'll make just a whole bunch of numbered SVG files for batch processing that can be extremely useful. All right, let's see. Okay, I wanted to find a sort of empty page. Sort of empty page. And here's a gradient. Gradients in laid out are objects in themselves. They're not fill properties or anything like that. I just think of them as just blocks of color. Like if you're painting, you lay out a block of color. It just sort of makes more sense to me. So you can add different color spots or stops. Oops. You can drag these things around just right on screen. It's very easy to do. You can select multiples and drag those multiples around. You can also do it for radial gradients, but for some reason that was not working last night, but now it's working. So you can adjust the circles of gradients. And also when I started to develop laid out, I noticed that in the PDF spec, it gives you all the math that you need for mesh gradients. So I thought, oh, it's, hey, what the hell, that's pretty neat. So let's see if this works. So this can do mesh gradients. But it is true that mesh gradients are, to really do anything useful with them, it takes a lot of time and you have to mess around with all these little points. And it's very cumbersome. The diffusion curve sounds very interesting. I should have thought about this before. It's much harder holding a microphone and demonstrating that. So. Just put it aside. Okay. I'm assuming it doesn't crash then perhaps I can. I've been redoing the interface with the, with Xlib. So now some of the things that use to work don't quite work. I'm using X input to use multiple mice to do tricks like the double scrolling and stuff like that. But I didn't quite get that done before today. So you can select points like that and rotate them around. Do that sort of thing. Yeah, I've wasted hours just goofing around with psychedelic effects like that. And you can select and drag edges to conveniently add more pieces to it. Or you can move this around and select where you want to subdivide patches. It gets progressively more, more painful to really make anything useful like this. Unless you do it right the first time. It's, but it's still very hard to do. Then once you have the mesh controls, you can adapt it to, you can adapt it to images also. Let's see if this works. So instead of having a color field as your color source, you can have an image as your source. So this was an image by the way that was, and all my photography I processed with the GIMP. So it's good job. You can do most of what I want. So you can do all sorts of bizarre distortions. I kind of like to have this sort of thing as a tool in the GIMP. I keep meaning to try to write something like that, but spherical panoramas, it just eats up all my time. So that's my basic object demo. So for the, I want the future of impositioning. So there will be three different basic kinds of impositions. One is the insignatures where first you take a piece of paper, then chop it into sections, and then take those sections and fold it in any way that you want. That's a pretty traditional way of making signatures. And then you can do trim, select a binding edge. So if you want to do images or I mean book sets are like the Western style page one, where the binding is on the left side, you fold it a particular way. If you want the binding on the other side for Japanese or whatever, you just fold it in such a way and assign the binding so it's on the other side. The next kind of net is just with some sort of polyhedron or a box or whatnot. I'm still in the process of making it so that you can easily unwrap such things. I've been trying to figure out how to import Scribes documents. So when you view those, everything is in this giant scratch basis for as I can tell. And it's so it's just one giant spread and the overlap between pages is dependent on that. I don't see an adequate way to make that into any of the first two. So most likely there will be a free imposition, which is more adaptable one page equals one particular type of paper. You can also override what type of paper or how it gets printed on papers. So say you have one image and you want to spread it across like 10 different pieces of paper, then you can plop down papers underneath it under any any spread view, any object view. Just put any number of papers behind it and makes it easy. There's lots of new like homemade user interfaces being developed by particularly newiegroup.com or we remotes to do wacky things or MIDI devices. That's something I'm definitely trying to implement into into a layout just to be able to move things around in strange ways that it's hard to do. So you can do everything with hand waving eventually. I think that would be kind of cool. I'm also trying to make laid out in such a way that it cooperates with other programs as easily as possible. So a software engines, that's the way to go. No one program is going to do everything that you want it to do. So like say you want text and scribes or paths and inkscape or like painting with my paint, then it would be convenient to be able to just send that layer to some other program, have it worked on and then have it be automatically updated, for instance, in the original program. For a laid out that unique features I suppose at the moment are measures and the impositioning. So I'm trying to make it easy to access the impositioning features from other programs. So speaking of interoperability, it's good to have nice documentation. In laid out you can dump out a description of what the file format actually is if you want to write importers, for instance, that I wouldn't recommend that, however, because the file format is extremely unstable, like many things in laid out. But should you want to experiment just because you're a masochist, then you can do a laid out file format and get something sort of useful. The screve is imported in laid out, it doesn't understand text, but it does import those blocks as mystery data. I don't think I'll do the mystery data demo. It's just like a blocks that has question marks that kind of bounce around as you move. And then when you export it, it sort of remembers what the data was. So I've done some tests where importing a screve is document, reimposing and then exporting, and then going back in screve as some tweaking, and it seems to work for printing booklets, which is a very commonly asked for thing. Let's see, and there is, I hope I have time for one more demo. Hi, so can you still hear me? So this is a something that I use for projecting panoramas, for instance, this was that ball. So it's a panorama. This is actually a polyhedral shape that has about 300 sides in it with a polyhedral projected onto it. It's basically globe gore is just slivers glued onto a ball. So I use this to figure out or to unwrap things onto it. So you can just do this and then unwrap a shape pretty easily. And then this, for instance, is lick observatory in California. It's this giant telescope. You'll notice this artifact here. That's because it was hot and the roof was melting. So you can take this whatever shape you have and move your image around, rotate things like that. So here's the globe. One easy way to unwrap, you can just do this. That's it. So two questions, please. What toolkit are you using for applications? Because this doesn't work very well. Well, I made my own. Partly when I first started this, this was like five years ago. I had like no programming experience in Linux at all. So I thought, I'll let the hell just figure it out myself. It's probably just as quick to make my own as to figure one of these other ones out. In retrospect, I think that's been totally wrong. I have learned a lot. It's at least better than it used to be. If you want to implement multi-touch stuff, that's still kind of going along a little slowly for the major toolkits. Whereas in mine, I can just hunker down for a month or so and then make it. So it's freedom, I suppose. No one else uses it. So I mean, I don't have to worry about screwing up anyone else. So it's convenient. A second question in the last one. Well, let's make three. Especially the last examples of unwrapping the pictures. You might have seen it about unwrapping. The examples were basically globes where you have... Unfortunately, I don't really recall the exact name, but it was like subdividing the globe into lots of small triangles and then taking into account the pattern of the globe itself. So that you have the continents sticking together and taking, for example, the rivers as potential breaks between the things. I found that quite interesting. Do you think... First, do you know this or are you interested in this? And second, do you think you might be interested in doing something similar? I think I know what you're talking about. But it's still a very flat way of projecting. So if you were to project it and then print it out, for instance, there is just a million little cuts. My interest is primarily for making stuff you can actually physically create. But theoretically, stuff like that is pretty neat. You can make some pretty interesting images with that. There's one Flickr group called Foldables where there's a few people that have been working in trying to figure out really wacky projections. So it's things like that and other strange curvy surfaces in a similar sort of vein. Okay, the bonus question. Sorry, I can't reach further. There's nothing more of a question of a request. Unwrap it again! Well, I'd have to warn you, I frequently, when I try to unwrap giant shapes like this, it kind of does peculiar things.
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Laidout is a desktop publishing program that I use primarily to make cartoon books. It can lay out images and gradients (including mesh gradients) onto booklets, as well as onto arbitrary polyhedral surfaces. Other novel features include controlled multiple image import, and image mesh warping. Being debugged currently are multicontact abilities. Discussion will also include experiences with various open source software for related tasks.
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10.5446/21520 (DOI)
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My name is Susan Spencer and I'm a networker. I'm not a programmer and actually I'm not a networker anymore. I'm retired and I only do what I want to do, which means no laundry. And here's my contact information. The contrast is not so great here, but if you find the sobrilliant.org, these slides will be online as well. I'm here today to try to generate some interest in this particular project for fashion design, open source fashion design software. This software would be used to create and import and modify clothing patterns. These clothing patterns would then be able to be modified to match custom measurements for your clients or for yourself. And we'd like to use open data formats so that it can be sent to other points along the manufacturing line to maybe some open hardware. So there are a lot of reasons to use open data formats. And to make this software interoperable with a lot of different things. One thing that's happening right now is that all of the big labels are watching the streets for what people are wearing. And then they shove it all into a magazine like Vogue or whatever. And really there are regional things that people wear. So this type of software would lower the initial investment that it takes to get into software creation, a garment apparel creation, so that independent designers could have a really good return on investment much faster. And these designs would then be owned entirely by the designer. Sometimes when they hook up with manufacturing companies or other entities, they have to pay royalties to own their designs. There are different types of business relationships in the garment industry that are fairly confusing. And I'd like to point out that there's a huge movement right now for people to find homemade everything, or handmade garments, handmade anything. It's a total, I think, a reaction to people growing up with plastic toys. No one wants the plastic. Even plastic fabric is going out. There's another problem with the garment industry is that everything is designed, and it's encouraged to be designed by the big fashion houses, to fit a size six or a size eight, you know, small size, so that when it gets to be a larger size, like, this is an extra large. And I don't, you know, to me in my head I'm still 12 years old. And I'm not that big, so adult sizes, you can't find them because they don't sell well, because they don't, when you increase the sizes, the proportions should be different, but the garment industry doesn't change the proportions of the design. They retain the same portion, proportions, as a small teenager, even though you may be somewhat larger. So this is a huge, this is a huge market of people who need to wear clothes, we all wear clothes. So anyway, if we make the software available for people to have at home and for independent designers, these are the people who buy organic fabrics and look for unusual type accessories. So you're really boosting a more healthy, vertically integrated garment industry as well. These are growing markets, they're not the normal markets that existed 10, 15 years ago, but corsets, huge markets, steampunk is growing, vintage clothing, even though you can find vintage clothes, they don't fit the contemporary body. So, because we don't wear the tie anything anymore, so no tie underwear, which is good, unless it's a corset. So those, the designers for these types of markets would make a lot more money if their investment costs were much lower. As I said, everyone wears clothes, this industry is so huge, there's room for everyone. Laundry alone is a $32 billion industry, billions. So if every single one of us in this room wanted to go into the industry, we could find a place. And as I said earlier, not everyone wants to wear the same type of clothes globally, there are different things people want to wear in Seattle than here in Brussels, but yet magazines sort of incorporate things that none of us would really want, and none of us want to pay thousands of dollars for. So, this would give a good opportunity for, I guess, regional definition and identity or personal identity. The software that I'd like to create would also use different algorithms than what is used in the industry right now. Sizes are increased by bus size, but that's not related to any other relation in your body. Your waist has usually a relationship to your hip size. Of course, your body size is fingertip to fingertip, and there's a nice ratio between here and here and here in the floor that is not retained by the garment industry designs at all. What I would propose would be a completely new way of sizing clothing to actual body proportions. So, it's fine, it's very, very difficult to alter a pattern. If they go and buy a butteric pattern or a hot pattern or an onion pattern, they usually have to change it to meet their own proportions, but even these garments are based on bus size. So, it's a problem. Also, this market is so huge, not just with designers, but with home sewers. There are more people buying sewing machines now than since the 1950s. So, this is a new thing, and it's great. People feel empowered to sew things from their own backyard suncovers to artwork. I helped a girl last year sew a dress from bicycle inner tubes, split them down in the middle, and it's great. But you have to have an old machine, really sturdy machine to do that, but it was fine. Of course, the additional benefits to open software is that schools can have access to it, and it's really important, I think, for young people to learn how to do things with their hands, not just academically, but make jewelry or make clothing or soft sculpture. You could use this type of software to come up with a lot of different things, especially if we left it open for people to create their own operations or just add the functionality as needed. So, this is a good way to get young people involved in the open source community. They don't need to wait until they're in their mid-20s and go, oh, this is cool. If they're 12, it's great. Then they kind of get on the bandwagon a lot sooner. And 12 and 13-year-olds are interested in this, very interested in fashion design. Males and females, this is not that gender, there's not a gender gap here. That age is all about the external what you wear, putting your heart on your sleeve, and saying who you are through how you look. I've got a couple of projects listed here that we could integrate for, you know, just... Well, taking measurements to make patterns can change depending on the person who takes the measurements. So, working with a 3D scanner like Brooks Brothers does and some high-end bathing suits manufacturers out in Las Vegas, you just walk into the booth and you get a 3D rendering of your entire structure. In Make Magazine, there was a spread on this guy who made his own 3D scanner. And I won't go to the links right now, but if you find my slides and go there, you can see the video. It's really, really great. Also, cutting table integration. If you have your design on your computer, you can just offload this via Bluetooth or however, you know, just sneakernet over to the cutting table. And if it's, you know, an XY plotter that's been revised with a cutter and a marker, then it could just go ahead and cut out your fabric for you and you don't have to, you know, do this number and you don't make mistakes. Additional modules would be the layout and yardage optimization. Now, that's normally included on the back of a software, I mean, a back of a pattern, but it's actually a fairly interesting algorithm. Okay, I'm going to add. Anyway, the current fashion design applications are all proprietary. They don't interoperate. Some require additions of other software like Adobe Illustrator. And some of, I'll just go through this really quick, burning in my label. It's a low end, but you can't design your own things. And everything fits very loosely, even if you put smaller measurements than what you normally have. And it's $400, but you can't create anything. C-Design, it's $2,800 for all the modules and it requires the Adobe Illustrator as well. And again, you have to use their templates and there's very little design, you know, you just don't have any control over the design beyond a certain margin. This is a nice pattern software, but it's $4,250. Yes, it's terrible. There are different methods to create patterns. This is the method that I would like to incorporate into this software, but I'll just show you these types of designs very quickly. Again, it can be very, very complex, but you can't get there, you can't get to this from those software packages that I showed you. So this is the basic actions or slash and spread. So this would be a vector graphics application. And I think I'm done. There's more. Thank you.
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This presentation invites developers to help create a suite of open source software to create and modify clothing patterns in open data formats to match an individual’s body measurement and generate customized patterns as printable files. Current applications are proprietary, do not interoperate, and are expensive. An open source solution would enable individual and small label designers to create and provide custom sized patterns without purchasing high-cost proprietary software.
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10.5446/21521 (DOI)
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Hi everyone. I will just introduce myself very quickly. I'm a visual artist who makes a lot of money with free graphic software. Fetch is a photo fetch application. If you prefer to give a gimp, or it's moving away from that, or Krita, there you save the images, with fetch you save the recipes to your images. And it should be so easy to use for everyone. How do you start? You start with some simple ingredients, and fetch has at the moment 55 of these ingredients. It's not very readable, but you get the impression that there are a lot of them. And the yellow ones are the ones which are new with the latest version. A big addition is the right support for metadata, which doesn't allow you to not only allow you to edit metadata or delete it, but also to do advanced things like gil tagging or time shifting of your pictures. Another thing is also like GPEG support. And also what's really exciting is that fetch now allows you to interact with other powerful free graphic software. So you can, even if you don't know anything about Blender, don't worry, you don't have to open Blender, you can now use Blender. Through fetch with one click of the button. The same is true for image magic. Everything which is possible in image magic is now also possible in fetch. And also fetch uses certain tools of Inkscape and GIMP in the background. I will come back on that later. Yeah, these are more actions which are possible. So you can pile up these ingredients into a nice recipe. And for example, what I use a lot in this presentation to eat my own dog food is here you see how it works. The first action is the round action, then it that's reflection, then it saves the image. So that's what I use for most of my screenshots to make them look nice in the presentation. And if that's too much work for you, you can even be more lazy because fetch can you offer a menu of pre cooked recipes. For example, to make batch buttons for your website or to make a Polaroid or to turn your images in 3D objects with Blender and so on. This allows you to save a lot of time because everything you can do for one image you can also do for thousands images because the amount of images don't matter anymore. I will give a quick demo. You can start fetch just from the menu. So you start by adding actions. For example, I will very quickly demonstrate because there are so many actions you can fill the results. So we do a reflection. We put it in a perspective and we of course will save it. So this is the action list to better overview what happens. So I just do a reflection perspective and save. I can just drag and drop pictures on it and it will batch it. The results is saved on the fetch folder on your desktop. You can change that to any folder you want. Let's say that I'm not happy with the perspective. I can click here and choose different projection and run it again. And you have it updated here. So this is just to demonstrate how easy it is to just quickly pile up something together and apply it to any amount of pictures you want. I can also demonstrate the library. Then, for example, let's choose a Polaroid and to show it can batch images. I will drop two images on it and then it will batch them and display them in the fetch folder. Or maybe it will display them on the desktop. So you see with just some clicks you can do very nice effects for a lot of images at the same time. And it will give you a nice notification in the end. You can also run fetch on the server so it doesn't depend on the user interface. You can execute it directly or you can prepare your action list in the user interface and run it on the server. Fetch also now has an image inspector. Before the image inspector could only handle one image at a time. But now you can change metadata also in the image inspector of one photo or of a whole row of photos. I can maybe also give a little demonstration of that. So you open the image inspector and I take just a photo. And I can go to the XIF metadata. And then, for example, if I go to the date, I see it's editable. And it says Wednesday when, for example, I change the day. You will see that the day switches to first day. So also all the values are connected together. So also new in this version is that you have much more visual feedback. So you have preview dialogues of the mask action or for the highlight action. As I said, fetch can now interact with the different free graphics software. So this means that it also can open much more formats. So it can open GIMP files. It can open RAW files through DCRAO. It can batch process SVG files into bitmaps with Inkscape. Because if you try to do this with ImageMagic, you get very bad results because ImageMagic can't handle the SVGs of Inkscape. And ImageMagic also allows almost any file format to be added from movies, font files, PDF, and so on. This is an overview of the ImageMagic actions. Well, you can't read them, but I will give some examples. So the ImageMagic has its own Polaroid action, which you can use as well. Or Pencil sketch action. And this is, for example, done with Blender. And you can apply that to any amount of photos you want as well. The Blender action works that you choose the object. Right now we have six objects. And then also with preview dialogues you can immediately choose, you don't specify the amount of degrees, you just immediately choose the few points you want. If you want you can change the axis, but that's not really necessary. And what's also new for the latest version is that we've been working on cross-platform support in our kitchen. Following the human interface guidelines of each platform. So here you see the result. There's one mistake. I think Apple people will see it. The open button on the toolbar is a huge sin. You should never do that on Apple. We will remove it. They have their own rows. Here you see, for example, the notifications in action. In Ubuntu we use a new notification system. On the Mac we use Growl. And Windows doesn't have its own system, so we provide a custom solution. This is the Windows installer. It's available now. It's not publicly available because we want to get feedback from beta testers. If there are any people here still using Windows, they can get it from the Windows installer from me. Same for the Mac installer. And the first version starts out as a private project, but now we are free to for developers. And it's growing every day. So if you want to contribute, you're welcome to join us. I don't think there's time for questions, maybe, but if there's one question, I'm happy to answer. And don't ask if there's a workshop because it was just this afternoon. So first we give you applause. One question. Well, Erik is getting ready. Anyone? Yes, there. So it looks like this can be used to call other programs, but can other programs call this, for instance? Is that pretty easy to do? That's also possible. I mean, you can do it from the comment line and also you can do it as a Python API. It's a quick answer. Okay.
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Phatch is a user friendly, cross-platform Photo Batch Processor and EXIF Renamer with a nice graphical user interface. Phatch handles all popular image formats and can duplicate (sub)folder hierarchies. It can batch resize, rotate, apply shadows, perspective, rounded corners and many more actions – in minutes instead of the hours or days needed to do so manually.
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10.5446/21522 (DOI)
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Okay. Hi, my name is Emre and I'm going to try to talk to you very quickly about Pure Dyn. So what's Pure Dyn? Pure Dyn is a live distribution which is basically an operating system that can run either on any medium, so hard drive, CD, DVD, USB key. And we wanted to be some kind of same-based system for media artists and designers, something very basic, simple, on which people can build on. The Pure Dyn is quite peculiar in the sense that it's all made by artists and designers and musicians and none of us are, let's say, proper programmer or computer scientist. We learned it the hard way. So we use Pure Dyn to make steps. That's how it started. It's really, really practical. It's a tool. It's not meant to be a demo as in, oh, look, I've got this DVD full of awesome application that you can check. No, it's something that we actually really use. The way it has been developed was exactly through our own practice. So there have been several iterations, for example, workshops. So at the beginning Pure Dyn started because we need to have some kind of an environment on which the people who were teaching too could go back home with the whole toolkit and don't have to worry about installing Linux from scratch or this kind of things. Also because a lot of documentation or the material of the workshop or what was done during the workshop could be found back at home in an almost similar context. And then because at home, yeah, it's also meant in our home, we started to use it as our default installation, as default system, which gave quite a big boost in the project because we were able to fix things quickly because we had direct interest in having it working correctly. And then we started to use that for our own gigs, for our project, for installation. And again, it boosted the project and pushed the project in new directions. So far, the original version of Pure Dyn was sketched on another live CD project called Dinabolik. And then for various reasons, we moved on to Dbian and we released two versions with Dbian, Miso and Likenn Potato. Yeah, we use a sub name because, yeah, I will explain it. And then recently we switched to Ubuntu and the latest table is based on Ubuntu with Dbian live script and it's called Current and Coriander. We moved to Ubuntu very quickly because it was getting extremely difficult for us to invest time in maintaining our own P-Builder, back porting, packaging and things like this. It was much more easier for us to work with the Ubuntu snapshots, but we kept the Dbian as a live system environment. So inside Pure Dyn, what you have is we develop everything based for a Pentium 3. So it might sound a bit surreal, but we think it's quite good to have a good multimedia environment that can run on rather old hardware. And also because all the optimization that you will see, all the problem, bottleneck that you will see on a Pentium 3 will pay off if you run the same system later on on a faster machine, obviously. We have a real time kernel. The Windows Manager desktop is XFCE because it's a good compromise between something that is user friendly and that brings up the usual meta-force that people are used to. But we slowly push them to use EvolWM or R-SOM when they start to use Pure Dyn, especially because EvolWM, for example, is perfect when you have to run installation or make performances. The applications on the systems are mixed of, so, Dbian live for all the bootings system, Ubuntu, the different repository from Ubuntu for the application, and then midi-buntu mostly for the Alza firmware. And then the Pure Dyn PPA, which is, if you know a bit about Launchpad and Ubuntu, you know what the PPA is. So it's our own package repository where we put everything there that we find that we think is either not packaged well enough or missing or for various reasons. So, very quickly, a small demo. So this, yeah, that's Pure Dyn. So when you put Pure Dyn, you get something like that. You've got a six Linux booter. And then, so this one is quite simple. In the next release, we will have options to boot in your different languages. And then you start Pure Dyn and it boots. And that's the usual, I can't see much, but, well, you know, it's booting. While it's booting, we're going to check the MacGyver flowchart. So the MacGyver flowchart is basically what makes Pure Dyn quite interesting for artists, midi-artists who need to basically have a system that can adapt to all kinds of different situations like MacGyver. So you have the system itself is stored as read-only either on a live CD or DVD, a live USB or a live HD. So anything that you can boot off. And then everything that you see after is completely optional. So then you can enable persistence for the changes that will be made on the system because you run live CD. If you change the wallpaper, if you install a new program, then you will lose it next time that you reboot, obviously, because everything is happening in the realm of your computer. So with persistence, you can store your changes either on a partition or on a disk image. A partition means all kind of different Linux, supported Linux file system or image can be stored also on a Windows or HFS partition. And the type of persistence that you can have is either for the full system. So even if you change it something in slash ETC or you screw up user folder or whatever, it will be remembered. Or only the home user, which is practical for a workshop or for small media lab because you can quickly only migrate the home folder from the users or custom and custom, then you can go crazy because you can just having only one file persistent and change or a set of files. It's a very fine grained system. Still booting? Yeah. Sorry. So how do we build this stuff? It's built from scratch and it's very, very important because a lot of live CD or multi-matter CD that are around are usually sort of converged. Yeah, not confession. Yeah, you just take your full installation, your full system, you install stuff manually, you change the wallpaper, you make your menu pretty and it's all nice. And then you got this magic tool that turns your full system into live CD. That's very nice if you want to have a snapshot of your system to show to your friends. But it's not very viable in the long run because you can't update. The packages are limited to what the person wanted you to have. So we built from scratch, which means that everything in pure dine is packaged, which also means that you can just have your own Ubuntu and to some extent even Dbian and just get our packages and integrate that with your own super. Then we try to avoid all kinds of bloats. So for example, we don't use all the recommends features of the package manager. If we need something from a package, we know why we need it and we enable it manually. So we don't have to pull half of a whole distribution when we want to install a particular software. We don't assume that our user are stupid. So what we provide is basically access to Internet, basic good system and as little background crap as possible. So if someone wants to have Bluetooth because it needs to be working for his remote or whatever, then it's just one line to type to pull it from the package repository and that's it. It's very, so we don't deal with specific case. We don't want to please anyone. That's what we call the command denominator. We don't want to please anyone. We don't want to say it's the multimedia distribution of the future and everyone will be pleased. No, we just want to see who uses it and we'll check for the common denominator. I think, yeah, when I switch window, it must freeze the thing. Well, anyway, it's the demo effect, so it could not work. So we use Launchpad to develop PureDyn and it's okay for, I would not recommend Launchpad for all kinds of software projects, but in our case, it's quite good because for the obvious integration with Ubuntu, at the moment, we have 11 developers working on the project and we have a so-called horizontal organization. So what we mean with that is that we don't have fine-grained permissions in this PureDyn team if you are in, which is usually not too hard to get in as you start to contribute a few things. Then you have access to all the repositories, to all, well, you are admin basically on everything. And we decided to do that and it's working for us because people take initiatives and don't feel they have to ask for something in particular to someone. We don't waste time in discussion. And because we all have quite, it's quite focused distribution, there's not much to be, it's quite rare when there is really a strong fundamental disagreement between us. The way we develop it is with, yeah, this stuff is really not working, is with code sprint. I will try it one last time. So code sprint, we probably know what it is and it was the best system we found for us. So we just meet every now and then and all together we work for a week nonstop and we try to clean as much bug as possible. And because it's an art media project, we have our code sprint hosted by usually media art festival or art organization which is quite, quite weird peculiar interesting mix. Then make your own soup. Make your own soup that means that we have developed a small, simple SDK to build the distribution. And it's very easy to use, it's documented, it's a sort of high level wrapper for live helper which is the lower tool that we use. And people can use it quickly to replicate exactly puredine and make some time customization that from changing the wallpaper to putting your own name on the splash screen or to just change the default applications. So we already have people using it. So, yeah, we have puredine craftivism where it was a special version developed for the art gallery in Bristol. CD-Straw is a Greek security thingy, this throw that is using puredine as basis. Bogotrax is a Colombian distribution that was used for a lot, lot of projects recently in Colombia. And then everyone, it's very easy to branch and fork the script to make your own stuff. So tomorrow, what do we want to do? We want to close, to work closer to art and design communities. What does that mean? That means that usually the puredine team is broken down is people who are interested in more specific things. For example, we have supercollider developers working with us and they know how to package correctly and to run supercollider on puredine. So every time there is something new for supercollider, they have access to everything so they can make the changes and they can push the changes to us. We don't have to do it ourselves. Same for flexors. That's the way we want to do it. People who are good at something, they can still do it on their own but because of Launchpad, it's very easy to propagate the changes and push updates to us. For the documentation, we started to work on Wikibooks and we are trying to follow a model of user case studies and not only how to use all tutorials. So we tried to look at artists who are using puredine or designers who are using puredine and what is their setup, what do they use and how is it done. So it brings some kind of context to documentation which is for us very, very useful and very inspiring. And your idea here, yes, we listen to our users, our beloved users. A lot of changes in puredine has been made because of discussion happening on the list. We have around 300 people on the list and it's quite high quality list in the sense that it's very, very focused and very specialist questions. That's it. Thank you. You can go on puredine.org if you want to get more information and try it out for yourself. Thank you. Thank you.
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Puredyne is the USB-bootable GNU/Linux operating system for creative media. It is a live distribution, you don’t need to install anything – simply boot your computer using a USB key or CD/DVD and you’re ready to start using software such as Pure Data, Supercollider, Icecast, Csound, Fluxus, Processing, Arduino, Gimp, Inkscape and much more.
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10.5446/21524 (DOI)
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ESQ1 project contains two programs. It's ESQ1 illustration program and the Uniconverter Graphics Translator. Uniconverter is a common line application, so I will not show you this application, but unfortunately, ESQ1, I cannot demonstrate because I have a problem with proprietary hardware. Project has started as a sketch, scan cell fork in 2003. Sketch and scan cell is a old project, very old project and have a long history, but unfortunately, this project was frozen in 2006. Therefore, on next year, our project present our application on LGM-2007 in Montreal, Canada. The unequivored feature of our project was called raw importer formats. Of course, this feature was interested by InScape and Scribble, so as a result of LGM, we have started another project, Uniconverter. Uniconverter is an ESQ1 without your graphic user interface. It's a simple scheme, how we create Uniconverter project. We just copied the ESQ1 code and remove all code related with graphic user interface. On the scheme, it's very simple, but actually, it's not was a simple issue because InScape asked for Uniconverter protein on Windows platform because a lot of InScape users use Windows version. There is a myth about that our project is pure Python implementation. It's really wrong because recently we have calculated a number of Python lines in our project and we found that 30% of code is a C language. So our project cannot be named as a pure Python project and it heavily depended on platform issues. Therefore, porting Uniconverter on Windows platform was not a simple issue and we have simplified many tasks during this porting. But such strategy quickly got good results. Users start using Uniconverter in InScape. Also after that, Scribblz start using Uniconverter for core drive importers and therefore Uniconverter has a part of all main distributives of Linux. After that, Scribblz got a lot of alerts and in Iniconverter 2 last alert we got on Trafizzdelibre to 009 in multimedia category. So what we have at present? The prices which we got on Trafizzdelibre we as usually spent on project hardware. We bought project blade server for builds and so we got project continuous integration. That is project builds every night and if any changes in repository, project go on rebuild and if we found any problem, any errors, so we can quickly fix it. So we got more solid, more stable applications and as a result was daily banner is built. That is we got every day new RPM and depth packages for our project. We have uploaded SQL release RPMs on our project site and found that it's very popular. From February to May approximately 30,000 SK-1 pre-release downloads, so application is very popular but it's only pure Linux application on this moment. In this year, SK-1 project was sponsored by Shingwanthik from South Korea and this sponsoring Hunchdicks accelerated our development and we have completed the global project refactoring and split our application on several packages. Before this we have two packages, SK-1 and Uniconverter. Now we have four packages. SK-1 and Uniconverter now have common package SK-1 Lips which contains font engine model, importer's expertise and other Python packages which is common for SK-1 and Uniconverter. Often we hear that people say you specially break Uniconverter development to provide for SK-1 more powerful, more modern importers. It was incorrect issue because we cannot import in all features from SK-1 to Uniconverter, do it in a multi-platform release of Uniconverter. Now SK-1 Lips is multi-platform package and allow apply all features of SK-1 importers to Uniconverter. So in SK-1, Scribous and other application which use Uniconverter have the same importers and expertise as a SK-1. That is the most popular importer is CoralDraw format importer. So if you use latest Uniconverter, you have most powerful import of CoralDraw importer. That is short description of SK-1 Lips structure. And we skip this. SK-1 SDK is a package for multi-platform widget set. It's another part of our development. We are going to port SK-1 on Windows and MacOS 6 platform. So widget set should be multi-platform and have the same look and feel as a current platform. And what's new in SK-1 we have now. First of all, we have additional color spaces. It's lab, gray skull, special registry black. It's a part of spot colors. So SK-1 have the same color management structure as Adobe products. Also we have a plan to transparent bitmaps like RGBA and SMIC-R bitmaps. And SK-1 Lips now contains our PDF generator which supports PDF 1517 versions. And right in Brussels we have finished project localization. We have added complete translation on Russian and Ukrainian and it's natural because it's our native languages. Also we have added templates for nine other languages. So anybody who wants to use the app nine other languages, so anybody who interested in collaboration with our project are welcome to translate on your native languages. We have templates for German, Portuguese, Italian, French and other locales. If your locates there is no in our pro directory you can add your locates at now. As I say before, multiple platform application is the main application, is the main development vector for SK-1. We are going after LGM announcing Pre-Release 2 for SK-1 because we cannot finish it all issues from our roadmap. But at the same time we are going to release a Uniconverter 115 which contain all described before features. That is powerful color management, font and design and up to date importing expertise. Also Uniconverter will contain advanced Windows features. Explore, Windows Explorer integration using context right mouse click on the files. This will be standalone application. Windows users doesn't like installing several packages. So we have prepared standalone application which doesn't require additional installation of Python, Python image library and so on. So this will be a single MSI installer. And also this installer will contain five script for in-scape. Okay, I'm finishing. And what's planned in future? At first we are going to switch on agile development process. It means that we will release, we will have short distance between releases and this will allow us improving user features support. Where is it features from users? Quick support of recent features from users, sorry. And also in nearest future we are planning a scale inversion for Windows and Mac OSX platform. Uniconverter in future will go to a factory at CorelDRAW importers. This feature is requested by our sponsoring and also they requested commercial grade PDF experts. I hope PDF experts will resolve old issue in-scape concerning PDF generation with smart colors. But of course this issue should be discussed in-scape with in-scape developers. Also another interesting issue which was requested by our sponsors is CDER exporter. That is writing in native CDER format. It's not a simple task because there is no such software which write to these formats. But it's very important issue because CorelDRAW relatively isolated from other software. CorelDRAW has a very important issue because CorelDRAW has poor importers of Adobe illustration formats. And you cannot transfer SMIC containing graphics from open source software to CorelDRAW. Only one format CorelDRAW will support very relatively good. It's scalable vector graphics. But if you're exporting in scalable vector graphics all SMIC related colors, only RGB colors, it's very important issue for prepress because RGB colors could produce a lot of problem in production. So thank you for your attention. So I think we take two questions. Is there any questions? Not right now? Well, Igor, well, ah, a question. You know what it means. So I've heard you're using Python Imaging Library, PIL, that's right. Yeah. So what do you think of the library? Because I've had the impression it's not, it's a bit limited compared to Image Magic and these libraries which are available for other programming languages, the Python bindings aren't very good. And they generally, PIL, it suggests, but it's not... So your question is about how we use Python Image Library. Yes. Python Image Library we use only for loading and saving rest of image, rest of graphics. But internally, in SQ1, we don't use Python Image Library blop for image processing because this will break rendering and therefore we use our own internal format for bitmaps to accelerate rendering of large and heavyweight bitmaps. So Python Image Library features is not important for us. Okay, thank you. So before we can bind into Image Magic and pass our internal data to Image Magic to process using Image Magic or graphics magic filters and so on. So Python Image Library is not a limitation for our project, but it's very good Python package for image processing, at least for starters. Okay, thank you. Second question and last question here. A follow-up. Yeah, about Python Image Manipulation. There was, I think there still is, a Python interface to Image Magic, but I think it's been un-maintained. And Python Image Library is actually, well, like we said, decent for starters. But if you want to do some heavy image processing, it will require some fast matrix processing. So you can try NumPy and NumericPy along with Image Magic. But if you're in it for the speed, then probably you really need to look into C extensions and other kinds of processing, all the pixel matrix data, other than that, PIL is actually nice. Thank you. Thank you, Igor. Thank you.
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The project was started in 2003 as a Sketch fork. Since that time sK1 became an awardwinning Open Source application and supports a lot of unique and professional publishing features. This year is a serious milestone in project development – global refactoring, multiplatform versions etc.
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10.5446/21525 (DOI)
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Today I'm going to show this an application that will be used for styling documents. This is a premiere of sorts. It has been developed for the last few months and I'm just going to show you what it's all about. So first for those not in the know what is tech. Tech is a type setting system that is quite different from what you might be used to with the with the model likes Scribus with a very specific way where you edit everything. I'm also with tech. You actually type right text files specifically marked up text files and then it will output your finished document. This is the default appearance of a generated document by tech. It's usually used inside the academic field mostly to typeset thesis and academic papers but it's quite useful for designers as well. But it does have quite a learning curve and due to the fact that it's quite different to the way that we that designers usually approach type setting it can be something of a stretch to get used to. So the way as I mentioned with tech is that instead of continually editing the document and finally exporting it to PDF you just edit text files and then you pass the text files to program to the computer so that it will just crunch them and spit out PDF using the PDF tech package. And the great thing about tech is that it's you just use text you just use plain text files. You don't need fancy editors although you can't find them and you can certainly use them. But you can you just need your old text editor and then run your stuff through it. The not so good part about tech of course it's relative is that it's all text. It's kind of hard to sometimes if you come from a graphic design background to just get used to a way of working just with command line and text editors. It's great for writing documents. If you want to write for writing your text marking it up saying this is a quotation this is a footnote. It's really good to be able to just use text. But for styling documents as I will see it's not so handy to just be working with text. A good analogy for the document creation and styling processes can be the website making. You do the HTML file where you specify what is what and then in the CSS file you say how it will look like. In tech it's pretty much the it can be pretty much the same workflow. You do a tech file which will be the content and then the style file which will be the style definitions and then in the end you end up with a PDF document. This is what text style definitions will look like. It might look weird but the rule is simple just keep pair values. This is that. The value of this property is that. And maybe we can do something with that. And so how can we probably bring something to styling tech? Namely think of a GUI which might be something that some have strong feelings for and some against. Because we all know that GUIs can really be affected by your experience. I mean especially when you're in such a clean and Zen tool as tech. If you try to stick a GUI in for as the example of Lix which is a GUI tool for tech it can pretty much take out a lot of the experience for you. So for this. Quite a long time ago, Kaveth, the nice gentleman who has been filming our talks came up with this program called Batch Commander. Which here is an example. You just opened tech files and you had a way to generate a GUI where you could specify which properties you want to be able to change in there. And from there you would run the program. You would click that run button and it would generate your style file and then output your tech document. Which it's really, really handy as I'll be showing later. Which leads me to the next point. If you can, maybe you're familiar with what you're seeing there. This version of Batch Commander was done with a toolkit called Revolution which is based on Apple's hypercard. Which is proprietary and kind of obscure. And so I took care of the job of taking it into more open frameworks. So I've redone Batch Commander in Python and QT. And what I'm going to show now is a video because you know, demos will definitely not work especially in the context of a short talk. This is a tech document. Simple tech document that I opened with G-Edit. And just your regular tech document. And I just have this one, this thing in my computer. Then right now I'll be opening Batch Commander and I'll show you how you can actually take care of the styling of the document in probably nicer way. This is Batch Commander. On the top you can see, you can choose the document that you're opening, the name of the style file that you'll be creating, and the name of the output file. And below you have the interface which I'll explain later is generated just by text files as well. And these correspond to several of the tech possibilities of styling. Now let's see when I decide to stop and actually run it. Then we have the data files which are the files that generate the interface. So now you open the tech file. And then select the style file and the output file and then you just run it. And then we have a PDF previewer that will show us right away the output. It's done a three-page document in one-tenth of a second. And this is the final PDF. This is not a preview. That's also probably worth mentioning. So now changing the text width value and then run, as you can see the difference. And this is actually the output PDF, the final PDF. So there's no intermediate steps. You're just taking care of the final document and you can run it again and fiddle with the controls which is handier than editing a style text file and running tech all over and repeating this process all over, over, and over. You can also change the units next to the values to specify how they should look. So now we are going back to the initial value. And now here comes the fun part. Thank you. Which is immediate mode. We have been clicking run all the time but now the changes are just instantaneous. You can just see. And the PDF is being generated every time you click on the button because tech is really fast and lends itself to this kind of approach. Then you can change parameters like paragraph height, paragraph advance, and many others that you can find in the tech reference. And you can just play with them which is something that editing a text file doesn't lend itself to do. And you've seen that the controls are generated by text files which have a very simple markup which I'll show in a moment. And you can create toggle boxes, color boxes, numbered values, and choice values. The color boxes are, well, something I'm really happy with. You can actually type color names and they will keep updating them. I'll just ask for this part of the... This is the markup that you would use to generate the interface by batch commander. This is a markup language called YAML which it's pretty close to JSON. And you just have to specify, you can recognize the stuff. The maximum minimum value, the default unit, decimal points, and so on. This is how you would specify a toggle box on and off. This choice box. I'll just fast forward because I've just got a five minute paper. And it's actually working really nicely so far. And this are the next steps for it. First, it would be really nice to have keyboard control. Not have to drag the mouse around and you could actually shift stuff with the keyboard. It would be really nice to, if some PyQt hackers were around, I'm definitely really want to meet you because there's some stuff that could be definitely made better. A nice thing about this approach is basically batch commander is generating text files. So you can use this for any engine that's based on text files for working like Povre, which is a 3D engine that just takes a text file and renders it with 3D commands and renders it. And batch commander also did a version that worked with Povre and this is one of the next steps. It also can be used for a Python script support. I use this with a shoebox which I'll show tomorrow. But in a minute, you can, for instance, generate a Python script with just variables, variable definitions, and then import it from another Python script. In that way, you can change the variables in real time with batch commander. That actually works. It would be nice to have a tech log viewer as well because tech creates really useful logs and right now the program doesn't have them. And the PDF viewer is really simple stuff. It's based on poplar and it could definitely use some work. But like I said, this project is really recent and that's something that I would ask of you. If you have any interest in tech or in type setting, really try it. That's the website. We need users to try this and tell us what's wrong to file bugs or just send feedback. That would be really great. And, well, hope you like it. Thank you.
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Batch Commander is a tool that provides a graphical interface for styling (La)TeX documents. While the plaintext-based nature of TeX is ideal for automated typesetting, Batch Commander provides a GUI for editing document styles visually, instead of manually editing style files and recompiling. A quick previewing system and support for extensions make Batch Commander worth a look for anyone using TeX, LaTeX or ConTeXt for their own work.
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10.5446/21419 (DOI)
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Alright, this talk is going to be about my student font project, Cantorail, which I mentioned in the previous talk very briefly. I was studying at the University of Reading on the Masters in Tightface Design Program, and this was my student project. When you set out to design a typeface, there has to be a reason why you're going to design it. And the reason which you are reading context, which is reading on mobile phones. With the mobile internet, the ability to read a lot of stuff, I mean the whole web on your mobile phone, whenever you're sat on a bus or train or you're waiting around, is just part of the fabric of life now for me, since I have such a phone. And this is a G1 phone running Google Android. It was the first Google Android handset available in England. And it had this web fonts feature so that you could look at a web page, and if it specified a custom font, it would use that font. And so I thought that this was really a good opportunity to design my typeface for that specific environment, which means this specific screen with the web page rendering software. So that was really the basic premise of the project, to design a text typeface for reading large amounts of texts on a very small pixel screen. And so to do that, there was a constant cycle between making some changes and then testing them out on the screen, and also testing them out on print, because at print you can really see the details in letter shapes. It's very difficult, I think, to design a typeface only looking at the laptop screen. The way that light works is very different between looking at something on paper and looking at something on screen. When you're looking on screen, the light is coming out at you, it's shining at you, and on paper, you know, you've got pigment on the paper, the light's bouncing off the paper to your eyes, and it creates a very different kind of visual perception. And obviously the resolution of having something printed is much higher, so you can really see the shapes properly. So those were the two places where I was testing the typeface, and I've prepared some bitmaps so that you can see the evolution of the project. So this was the very first version of the word adhesion, and this is a word which we use at the University of Reading as a kind of prototyping word. It allows you to, working in this way, allows you to test out ideas for features of the typeface and rapidly cycle through different ideas without having to deal with propagating your idea to all of the letters in the alphabet. And so I just click through here. You can see the quite subtle changes that I was making as the typeface developed. So there were some spacing changes, some height changes. And then as the typeface kind of became stable at this word, as the features in this word became stable, then I started developing the other letters, which means that the changes here became less. And so you can see that the spacing between the letters changed quite a lot, even though the actual shapes of the letters didn't change. And then you can see here that I added the countertools and accents, which brings those letters down a bit. And that was the evolution of the face. So in terms of testing, I wrote a build script using the font for Python scripting. And this basically, let's see here, had a snapshot function which would rename the font's metadata to apply the current date and time to the font name and then save a version of the font both as font for source and as a true type font file that I could then use to test with. The build script also produced a tech document which specified to use the generated true type font. And I also produced a HTML page in the same way so that I could test the font using the phone. And having a script to do this made working a lot faster than when I started off and I was doing these stages manually every time. And I can show you what this looks like in font forge. So this is font forge. And you can see here's a letter. So if I made some changes to this, I can go to the tools menu and say next step and then it would run through and it doesn't currently work on my laptop it seems. But when I was working it would run through, give me status output there and produce the fonts in the directory such as, yeah, this one. So you can see the way that that worked. So what I ended up with was a lot of fonts. So this is all of the fonts that I used to generate the preview of the evolution I just showed you a moment ago. And so this is a very rudimentary version control system where it's a kind of write only version control system. And it would obviously be possible to write a script to check these into a proper version control system. But having it in this kind of non-sophisticated way meant that it was very easy to deal with. I didn't have to deal with version control systems, you know, going back reverting to revisions ago to get to the font from a few visions ago. It was just there on the file system named in a sensible way. And I think that going forwards using version control systems for designing fonts that the level of complexity of version control really has to be at that very simple level. So it's very visible what's happening. And just using the regular file system and, you know, the regular file manager was a way I was very comfortable doing that. But I think that there's a lot of room for improvement with that kind of thing. Okay. So that was the build script. And the other big thing when designing this was I used Spiros blinds to do a lot of the design work. And the good side to that was that the, the, the, when you're designing a letter form, then you can see here that you've got this curve for the inside of the E and this outer curve. And these two together give you a single shape which ought to look like it's been made through a mark making tool. So the two outlines together ought to look like they belong together. And using Spiros blinds, I found it quite difficult to create that illusion that the two separate curves belong together. And even though each curve individually is very smooth, there is now a very good feature in Fontforge for dealing with that so that if you place a Spiros blind down, something like this. Then you can pass a, it's called the expand stroke feature. And you can pass a pen nib kind of shape over this. So for example, we can take a flat pen like this. Which gives us exactly what that kind of rectangular shape would do and passed over that smooth Spiros blind. And so this function gives you those two outer edges which are by definition related because it's, they've been created from that parent kind of skeleton spline. And that spline is, is guaranteed smooth because of Spiros. So this feature I think is something which I would have liked to have, liked to have had when I was developing the font so that I could have that as a kind of guide to work from. And as I continue to develop the font, then this is something I'm going to be looking into. So as I say, I started developing the font with the word adhesion and then continued to build out the rest of the lower case and then create the capitals. And as that got more and more complicated, then the testing documents I was generating had to change. So you can see typical testing document at the beginning, at the very beginning. It was like this. And this is just random words that can be created with the characters from that first word adhesion. And it's just a text block. It's very simple. As the typeface developed, then I would both print out the larger letters. And a large text block. So this is a spacing example. So in order to space the letters, then the script was very useful for producing lines of text with every letter in the middle like this. So you could judge the space, so I could judge the spacing of that letter in context with the n and the o, which gave the general rhythm of the typeface. So with the capitals, then this was a document to test all of the capitals together. And this shows the numbers, the way I was testing the numbers, also in context, and again generated using the building script. Okay. And so, yeah, that's it. Any questions? Thank you very much, Dave. I think we have time for three questions. Yes. Did you use Fontforge when you were at the University of Reading? Yeah, so I was using Fontforge as a show, and that was exactly how I did the project the whole way through. And I didn't use any other tools other than Fontforge. I found that when I started out, the very first thing that I tried was to sketch on paper and then scan it in and trace over that, put that into which I did using Inkscape, as you can see like this. So I traced over it and then brought it into Fontforge. And the result I didn't think was very good because there were so many things happening with the sketch that when I traced it in and digitized it, that it wasn't giving the kind of coherence consistency that a typeface needs. So I abandoned that and I drew only on screen. I was using sketching on paper to plan ideas, but I did everything in Fontforge. Someone else? Yeah. I came Richard. Hey, my question is, since I'm Bulgarian and we used the Kirolek letters, and it's more related probably to your previous talk, because we noticed that me and other friends noticed that only one of the typefaces that Google supports so far support Kirolek letters. And I would guess that they don't support Arabic, Chinese, and so on either. So my question is, what do you need as a typeface designer to support more languages, more alphabets, and are there plans for Google if you have that information, of course? Do Google plan, does Google plan to support more languages and more? All right. I'm working on a very simple kind of flat contract to provide my font to Google for their services, and I've got no idea what Google is planning to do. Nikola, I have another question. Nikola, if you speak, it's impossible to translate, so then you need to come forward. So I'm sorry. I'm sorry for the translation. I'm just saying that if you look, Raf Levine has posted a blog recently about the plans that Google has for the Google Form Directory to move beyond the Latin one set. So not a huge amount of information, but they're looking into it as far as we know. The third question is in the back. Sorry. I just, maybe I should answer this question. So in terms of what the people need to design for scripts they're not familiar with, I mean, I'm not familiar with Cyrillic, for example, then you need to have some knowledge about the history of those letter forms. That was a big thing, which, you know, the course I attended really focused on, and I really deeply appreciated the time I spent putting into learning the history when I came to design the forms. This type design is often about a balance between convention and originality. You're trying to make something which is you and original, and at the same time something which fits the conventions what people are used to reading. And so if I was going to make a Cyrillic extension to my student project, then I would have to try and look at the history of the letter forms and feel, you know, where does the kinds of shapes that I've got already, where do they fit into the historical context, do they fit at all, is this anything like anything that's gone before it? So that would be the first thing that I would say people had to be aware of. In terms of the technicality stuff, then there's not that much mystery to that, but the history and the kind of more artistic end of it is tricky, especially if you can't actually read the language. The testing documents which I produced, the reason I really wanted to automate that was because I found that when I was actually able to read text with the font that I've drawn, then my mind kind of shifted, and I was able to say, oh, this isn't right, this has got to change, this isn't too heavy here, this is too light there, and then move that up a bit, whatever, because the reading mind is very different to when you're looking at something. And so as a non-native reader, then not having that ability would mean the type design process would be more difficult for me. But clearly, since a lot of the best type designs for non-Latin scripts have been done by people who don't read them, it's obviously possible. Thank you. We have the third question. Thank you. I have a question about your workflow, because it's apparent that there's a lot of iteration involved in creating the font, and you've designed the font in multiple ways, and you've got the italic style. Do you, like, have you, I don't know, just have you, and would you do it again, like, design the one-weight, one-width first, have complete coverage, and then move on to the others? Or, like, what's the trick to keep them in sync? Like, I've only done a very stylized font, but just wanted to do the different weights, and then it's really a nightmare to keep them in sync when you change a property of a glyph, and then you need to do it for all of them. Okay. So, thank you to be taking on this. I don't have much experience with that. You know, my student project was very much focused on the regular and on what, you know, kind of the essential basics of doing type design, and dealing with a family was something which already came towards the end, and so the process, the workflow that I'd done, didn't take that into account. The way that that kind of process is done is with interpolation, and so having the parameters that are used to generate the members of the family through the interpolation system, having that noted in a, you know, useful, consistent way would be something which I would be looking into. So Robofop library is an open-sourced library which has a lot of these functions, and it's being used in, I think, some commercial software, but the underlying library is, I think, open-sourced. Yeah, that's right. So the libraries for interpolation inside Fontforge are also quite, I mean, they work well. It's just something that I didn't look into yet. There's lots of work for Free Fonts to be done. So yeah, that'll be done. Thank you very much. All right. Thank you.
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This talk presents the techniques and software I used and developed for creating the Cantarell font family, and looks at the future of free software type design. During the last 2 years I undertook the prestigious MA Typeface Design programme at the University of Reading, UK. The course involves two major projects, a theoretical dissertation and a practical type design. I wrote about the nexus of free software and typeface design, and used only free software to design Cantarell.
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10.5446/21421 (DOI)
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Welcome to this talk about extending Python. This will be quite a technical talk. My name is Martin Einhold. I'm a developer of MyPaint. MyPaint, of course, is written in Python. So Python with extensions written in C++. It's still a small project, only 12,000 lines of code. And it started some six years ago, and is slowly evolving and gaining some popularity recently. I get sometimes the feedback that the program is quite fast. So I hope to share a bit with you the technique used to make the patent. But first of all, what is all this Python hype all about? Python is just a very nice high-level language. So you can see here's a way to walk through a list in code. Do it in C++ or also in C, for example, C object. And you will end up with a hellot of code. So Python makes this nice to keep it compact. But there are also drawbacks, of course. One of the drawbacks is speed. So is Python really fast enough? So here are my experiences. For GUI stuff, of course, things happen in the order of a second. It just doesn't matter how fast it is. It will work. You can also do some stuff in Python for each tile. So usually with roster-based images, you have a tiled image. And for each of those tiles, there are pixels in there. You can't walk through each pixel, but walking through each tile and composite it, that's perfectly possible and fast enough in Python. And it's even fast enough to go through something for each motion event. So for example, when you have a graphic tablet, there are lots of motion events generated per second, and you don't really notice much overhead when you process those motion events in Python. But this is about where it ends. When you have to do things for each pixel, like compositing or scaling or run some interpolation algorithm, then it will have to be done in C++ to get up to speed. So now there are several tools available to extend Python. And now the opera tree ones are those that I know, that I have tried myself. SWIG is the most best-known one, I think. You'll stumble over that, and it's very good for wrapping an existing library especially. You just take your C++ header files, and it generates a code to make a wrap up. There is also Pyrex, that's a time-�-dried. It's a Python-like language. I will not say much about it. The main reason for me for not using this is, it's a special language, and I really like to write in C where I know how to optimize things and not learn an additional language. And in my paint, I even used those code generators used from PyGTK, a very specialized code generator. But I got away from that later because I found the G object is a bit too verbose. Here, have a look at the C or boost Python if you are into C++, especially the more advanced stuff like templates and so, I will be handled better by those. So what I have settled with now is a Svig mainly, but I'm using it a bit differently than when I started. So here is a very simple example. That's actually all the code you need for a Python extension. You just write a header file, implement your code in a header file. Adjust normal C code. And then you write this i file for Svig. That will just tell how the module is called, where to find the file and include it in C and include it for Svig. And that will work out. So how do you compile this beast? I recommend to use the distitutils, which is, I think, the easiest way to get the right compile command called Svig. So you write this setup script and you execute it with the buildxt command, buildxt for build extension, minus i is to put the result into the current directory, so you can directly use it. I start Python, import it, and call the code that we have wrapped. So I think this is quite a simple way to do this, but it will get a bit more complicated. But for Svig, that's, I think, all you need to know, is because Svig goes to great lengths to wrap existing libraries. And it has those tight maps, and they are really getting complicated, and things are getting complex when you want to wrap something that is not a, you pass arguments that are not a float, or an integer or something, but are a pointer to something, or you return several values. So for this, I would not use Svig, but I use the Python C API directly. And Svig actually supports this. I think this is not known so well, but you can just use that together with Svig. I'll have a short word about the Python C API. First of all, it's just a C API, so there's documentation at python.org. You'll find it, but there's one important concept you'll have to know that is reference counting. So Python uses a reference count for each object. Those are those pi object pointers. And there is a convention who owns those references. So you know when you have to release them or when you have to increment a number of references. And it's quite a simple convention. Basically, when you call a function, the caller always owns the references. So when the function returns a value, it returns a new reference, which the caller is responsible to release. And the other way around, when the caller passes an argument, it will be owned by the caller, and the function does not need to release it. So it's a borrowed reference. So now here comes a bit more advanced example. This is, of course, also be parsed by Svig, just as in a header file as we saw before. You can do a class, you can make public members of the class, and you can see below that you can just access this member from Python. You can just write a value to it. And here we have a member function that returns a pi object pointer. This is how we use the Python CAPI. So Svig will not do anything with this pointer. We can just call the function pi build value. This is an example of this API. We pass it a format string. We are passing three integers, and it will return a new reference to a Python dictionary, and not a dictionary, a tuple, of those three integer values. So in the code below you see you can use this like you would do in normal Python region, tree values, without doing it with pointer magic, like you would usually do in C. Now this is very nice, but there is one important thing for graphic applications especially. You need a way to share the pixel data, and you do not want to copy this data. You just want to share the pointer. And for this there is, at least as I see it, this central numeric Python array class, which just is a Python object wrapping a pointer with information, how it is organized and stuff. And you have those different libraries, Python bindings of ordinary C libraries, for example gdkpxbof, can do scaling, load PNG images, or the kairosurface, you can render some vector, stuff draw nice, untilized lines, or the pill image library, they all provide a way to convert their memory into a numeric Python array. And this array we can then access from C. So let's first have a quick word about numeric Python. Numeric Python is just an extension, a Python library that allows you to do Muff operations, so adding whole arrays of integers, for example. And here's a little example, how we just can create an array of zeros and assign some values there using the Python slicing methods and put some randomness in it, and below you see the picture we get out of that. So now the question is how do we interface now with our own extension with this numeric Python array, and here I've got a small example for that. It's a function called render, it renders something, it takes as an argument, it takes a py object in Python, everything is a py object, but actually in there is a numeric Python array, and we pass it some other argument, for example, a radius, and then we can use this API call to get the height and width of the array, for example, and we can make simple costs to get the pointer to the actual data, and then we can loop through all the pixels and it will be faster. Speed of C use all the usual tricks to optimize that. Okay, that's about what I wanted to say about this topic. Now let's move a bit more to analyzing an existing program. This is, I think, an underrated tool to profile Python code. C profile is pretty much known, but this sheeprof2. makes for a very nice visualization of the result. So I can only recommend you to try this if you are trying to get a feeling what is low in your Python code, in your Python program. It will get down to the level of the library calls. If you have an extension, you will see the functions of your extension that are executed, but you will not see what C functions they are calling themselves. This is where it ends. Now for more in-depth profiling, maybe it's not your Python code that is slow, but it's something else. Maybe some library has a problem. So for this, I usually do system profiling. All profile is quite nice for this. It can analyze the whole system, including the kernel, even if you need to. And it will tell you where it spends the execution time. So for example, here I got a profile of myPaint doing scrolling, and we see that the actually time is spent in XORC, not in myPaint and not even in the Python extension of myPaint, but XORC is using this little pixman to zoom the image, I think. And we see below, there's 20% of the time is still being spent in Python and in the extension library, specific here to myPaint. And we also see how much time is spent in the C library, for example, feeling memory or copying memory is done there. And we can also break this down to the individual symbols, of course. I haven't showed this on the slide. So I recommend to do this if things are going slow. You might be surprised what actually is causing the slowdown. Short word about debugging, a very short word. It's just the same as any debugging a Python library, not a C library, I mean. When you have a Python program, you can just start the new debugger, for example, or any debugger on the Python binary, and then you start Python. And it will go into your library and you can get the backtrace, you can set brain points and all that stuff. Okay. Now here is a final slide about memory leaks. That's because I think it's quite important to know if you actually are writing an extension, you will have box of course. And the good thing here is to know where those bugs usually come from. The most common bug you will produce in Python, memory leak, I think, is that you have a reference to some object that is keeping the object alive. So you start it into some list, but you don't actually need it. And you just, for example, you append to this list, for example, the pixel data of the layers. And the list was not meant to start unpermanently, but, well, mistakes happen. And it's a bit hard actually to find those kind of bugs. I think correct me afterwards if you know something, but I think there is no common tool to do this. You can ask Python for a list of all the memory, it is managing all the objects, and you can count the number of instances, but this, well, it's a bit tricky and it will be slow. And now another common trap is reference cycles. For this, I have to say, Python uses this reference counting, but then there can be an object referencing another one, and that one referencing the first again. So to break those cycles, there is the garbage collector, and the garbage collector can only work if it knows how to call the destructures of those Python objects. And especially in what order. So if you have a reference cycle and both of the objects have a destructor, then Python doesn't know how what the order is to call them. And it will, well, it will not do anything, it will leave the reference alive. Luckily, this is easy to detect. You have just to call the, to check the garbage collector module. There is this garbage member, and when it is empty, then it's good, and when there is some stuff in there, then you have a look at it and find out how to break those reference cycles. Danger Heels, as we generate those destructures, so watch out, you might have to disable it. And no, you also forget to decrease the reference count in your C code, but this is quite rare. Often you don't have to handle this at all, and, well, it never happened to me that actually this was the problem. So that's about it. There will be code samples available here on this world if you want to check out some very small examples. And if there are any questions. Questions. Thank you very much. Does anyone have a question? There's always, of course, the chance to ask you questions later. Maybe it's the moment to invite the people that have arrived a bit later to come and have a seat. In the meantime, people can think about the questions they might have. Ego, for example. Welcome. Yes. There's a question here. Generally speaking, would you, let me say, conseille, would you say to project to try to work on Python and having interfaces to see if something projects should consider, generally speaking? Yes, I think, especially if the project is new, if there is existing code, maybe there's a large C code base. What projects usually seem to do is they do not extend Python, but they embed it. So they call it from the C code. But I would certainly recommend when starting a new project, if you want to do this in Python, then extend Python. Do not embed Python. But for an existing project, it depends, of course, what's the developer's want. If they are somewhat familiar with Python, if they like the language, and rewriting the whole application might not be an option. We have time for one more question, I think. Okay, we can discuss later. Thank you very much.
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Python is a nice high-level language, but most graphic applications have some code that must run fast at any price. Everyone knows that it is possible to write C/C++ extensions for Python. Not everyone knows that it can be done cleanly, simply and DRY.
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10.5446/21422 (DOI)
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Hello everybody. I'm Dennis Jacquerie. My presentation is about form designing features for African languages. So the first question is why would you want to design fonts for African languages? And then I'm going to talk about what are the actual needs of African languages, recording fonts. And then I'm going to talk about some fonts I've been doing work with. So the situation right now in Africa is there's about 2,000 languages. So it's quite a lot considering some organizations count about 8,000 for the whole world. And about 25 languages are spoken by half of Africa. So dealing with African languages is something that's quite feasible if you just want to cover half of Africa. And most of, oh, sorry. There's a mistake here. It should be 20% do have orthography. So actually 80% don't have an orthography. But most African languages are in the same language families. And so most of them share the same features. And so very often if one language has already an orthography or a spelling or some published text, the neighbor language can probably reuse the same set of orthographic rules and things like that and characters. The thing with African languages, because most countries in Africa have only been independent for, I guess, half a century or a bit more, the colonial languages are very important. Most of them are actually using colonial languages for anything official. So the law, most of the news is written in a foreign language, pretty much, that people have to learn at school or at university. And their native languages are mostly spoken either at home or with friends or only in spoken media, so television and radio. And there's very little use of the local languages in written media. And the thing is right now, Africa is slowly developing as it should be. And so there's interest rising in companies doing business in Africa and doing business in the local languages so people can use a cell phone in their own language instead of the language they had to learn at school. And there's very few orthographies that are standardized. But that I mean that there's either an organization or a government that has set out a law that people can follow instead of arguing whether they should use one letter or the other that just follow what's standardized. So the purpose of working with the fonts for African languages is to encourage people to use their language and to publish and to trade and to do more things in their own language because it's more accessible to them. So it's easier to get organized and work together and develop things in Africa. And so it's much better for kids to learn basic stuff or even advanced stuff in their own language. So that's somewhere that things need to be easier for people to publish educational material. It's better for the press to use local languages so people can get information properly and not just have a notion of what's happening but instead know exactly what's happening. Because it's actually true a few years ago in the Congo there was an election and before that they had to vote whether they want to accept their constitution. But some people had no idea what the constitution actually was. They thought it was a presidential candidate. So to make the fonts, first you need to meet the base guineas. So I had to research what are the basic needs of most African languages that are documented. And then once I have those basic needs, the fonts can be made and published so people can start using them and publish with them. And also those fonts are with open source licenses. So it can encourage people to reuse them and modify them and be creative. So there's actually several scripts. So people don't just write with Latin characters or Arabic characters in scripts in Africa. Most languages use the Latin script because it was what was used by the colonial authorities. In Northern Africa and Western Africa, a lot of languages, also Eastern Africa, a lot of languages use Arabic script. In Ethiopia, they use the Ethiopian script. Tefana is used in North Western Africa. Nkou is a language, a script that was devised a bit more than a century ago. And it's used in some communities quite a lot. But it's in Western Africa. Fah is also in the area. And there's a lot of other scripts that have been developed by local people who wanted to have their own script instead of just using a script that was imported from somewhere else. And so actually, luckily, Latin script already supports some major African languages like Soheili, Zulu, Shona, and more. But many African languages that are widely spoken need extended Latin with special characters that are not provided by most Thai faces and fonts. For example, there's a house that's spoken in Western Africa. That's 40 million people. And they only have a handful of fonts they can use to publish or write text or read text. There's a full spoken in all Western Africa. Eastern, yeah, Western Africa. Europe, Nigeria, there's Akan, and Ghana. There's more and more. And so all of these languages, depending on which country and which colonial state was there, some of them have standardized orthographies. And some of them have only standardized them once they became independent. And some of them, even though they've been in for a while, only started looking at the local languages in the 90s or even more recently. And so the focus of the work I've done is mostly on the ones that have been standardized or the ones that have some orthography manuals published by NGOs doing work on the ground. And so the fonts, actually, there's a couple of URW fonts that are used. One is not rendered properly here. But then there's a couple of other MG open fonts. And I've also done work on the droid and liberation fonts that have been recently published. And so the needs for the characters, most of the needs are pretty simple because it's either variants of characters that already exist or it's characters where the shapes are borrowed from a Greek or sometimes a couple look like Cyrillic too. And a lot of them, as you can see at the bottom here, are just regular characters with extra parts like hooks or strokes. And of course, there's plenty of characters that are just with accents or diacritics on top or below. And because of the way Unicode works, not all the accented characters are available. So sometimes you actually need to combine an accent with a base character to produce the accented character. So the design is quite simple if you just want to do those letters. You just take the original letter and just flip it over. Then you can just borrow the letter from other scripts. So here you can see the epsilon is just quite easy to have an open E. But sometimes you might want to have a different design to match better with the Latin script. And sometimes also you might actually have conflict because here that vowel is quite similar to the V in italic. So you might want to have a different design to avoid ambiguity in that language or in those languages. Also with the hooks, sometimes in italic it's an issue. For example, here it's the F with a hook. Actually, here it's an issue in non-italic and regular because in Unicode that character is also used for the Florent, the former currency of the Kingdom of the Netherlands. So here you want to have a design that where you can clearly see the difference between the F and the F with a hook. There are also some languages where the traditional shape of a character is different from the one that's mostly used in published fonts. So here it's the ng character. So you can see there's the relo shape where it's a capital N that's the most common one in European fonts. But for African languages, people are used and prefer a shape that looks like the lowercase N. And so once you've dealt with all the different character shapes, this is of course the die critics. So that's the accents that need to be either added to these characters to have a pre-composed form. So where the accented character is one Unicode character. And sometimes you have to have two characters, meaning you have the base letter and the accent as two different characters. And so to do that, you actually need to use some features in OpenType to position them properly. And sometimes, so all you need to define is where that accent is going to anchor and where the anchor of that accent is. And so your computer should take care of combining two as the font specifies. And sometimes you also want to replace a shape. So previously, it was simply positioning the accent on top of the character. But here, you actually have the eye with a dot. And so you want to replace the eye with a dot, with an eye without a dot. So you can then position the accent on top of it without having a conflict with the dot. Then, of course, you can also have the accents below. And you can also have stacked accents, because some languages use one accent to represent the length of a vowel. And then they use another accent to indicate the tone, whether it's high or low or rising or something else. And some other languages also use the SidiLet to indicate a variation of pronunciation of vowels. So that's also something that's needed for African languages. And there you go. So all the work is published on the website, africanlocalization.net. Thank you.
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This presentation will discuss the requirements of orthographies for African languages in Latin scripts and shows how to implement them with modern fonts technologies. Good practices, mistakes and evaluation of fonts for African languages with high requirements will be discussed. The presentation will also showcase various font projects that are benefitting from the input, feedback and work of the Open Source community.
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10.5446/21428 (DOI)
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Hi. My name is Pete Ipple and I'm an artist from Ventura, California that's just a little bit north of Los Angeles about an hour's train ride. And I just moved there from San Francisco and it's sort of one of those situations where it's new place, new life, new art, new everything. So my background is in photography and computer art. I have an undergraduate degree in cognitive science as well and a master's in masters of fine arts and new genres and performance. So my work is all over the place and when people ask me what do I do, I say I present complex ideas in compelling ways. So today I'm going to be discussing revivalist trends in art with relationship to the handmade and folk tradition, specifically in the fiber arts. Innovative artists right now are having digital fluency and they easily navigate network communities and collaborate openly. By comparing pixels to patchwork, vectors to stitches, bitmaps to patterns and layers to quilts, they investigate the overlap among a variety of disciplines. So I'm going to give you some questions to think about and then we're going all images. So the first question to sort of think about is what drew youth who grew up in digital technology back to the fiber arts? Was it an aesthetic commonality or a resistance to the virtual world of the computer and a lust for tactility? And then another question is how is the do-it-yourself community both in software and the fiber arts, how can they learn from each other and collaborate? And then how can looking back at a quilting circle and other folk traditions like storytelling, music taught by ear, et cetera, influence software development? So, okay, I just learned how to use Linux like three days ago, so I'm pretty psyched. I bought the computer on the way here. So, Leap of Graphics has been awesome. So this is starting out, pardon me, let me try that again. Oh, dear. I get the applause and mess it up. One second. Okay, command line, bam. Oh, there it is. Okay, so this is starting out of my master's thesis. What I've been thinking a lot about is how much of an image can you reduce and still have it imply something? So these started out as very small format Japanese woodblock prints, and I reduced the block down to make primitive of an octopus, a coy, and a seahorse. And so then I scanned these into the computer and was trying to make a gigantic image with very minimal data. So these are each about three or four kilobytes because they're a gift format and the pixels are gigantic. But from far away they resolve and imply what they are. They're printed on Tyvek, mounted on silk in a very traditional way. On the hammock stand there's another piece called the bed of memories and what that is is two years of photographs, did a photo collage of myself sort of laying down. And again, that resolves when you're far away and when you come up close, it's sort of a personal narrative over those two years. Here's a detail of the coy and then, you know, the detail of the bed of memories. Which I've actually now made it a kite so when you fly it, it resolves into the sky so you can sleep in the clouds. It's a nice performance piece, you know, you fly it out there and it's huge. It's 84 by 48 inches. This is, I saw the brush making discussion this morning. I was really inspiring because I've been experimenting a lot with the relationship between traditional and digital brushes. So this is, again, an older piece where I was trying to do a zen circle on the computer. And, well, it's pretty nice actually. I enjoy it very much. And when I printed it, I used a thermal wax printer. I don't know if you're familiar with those, but they predated the laser printer. They have wax inside and then there's a static charge that sucks the wax to a drum and it's heated and it comes out with these amazing bands. So there's a sort of sits on top of the page. And so it looks like it's a brush stroke rather than being in the paper like an inkjet would be. And then this is a traditional Sumi on linen. So this is sort of another path of my work. Again, a hand-drawn dip pen Marlin, oops, put into vector graphics and then patterns applied. And then again with the printing, it gets a banding. So this is a 14 by 14 inch, excuse me, 14 by 14 foot piece that is glued together, sort of a matrix again, pixels iterating over time. And I also do traditional painting. Now, I don't like these paintings very much and I was also having a tough time at home, so I decided to tear them apart. Now, when I was doing this, I didn't really know what I was doing other than the fact that I wanted to get rid of the paintings. So then I started to put them on top of each other and started to weave them together. And all of a sudden, I realized that I just made a matrix of pixels. And this piece is called Gender Resolution and again, it deals with the same thing. Weaving. And then this particular piece takes a male form and a female form and overlaps them and makes sort of this mysterious form that's abstract and also will resolve one at smaller. So it's a thumbnail or something like that, but it's 36 by 48. So when I initially made it, it was flat to the wall. And then eventually I put about a four-inch stretcher on it to take it out so you can get these kind of nice effects from different angles of how the light hits it. The piece on the right is called Implied Tree. This looks a lot more like a vector. It's just flat cloth. And what I did was I actually had fall in my studio and I sort of sprinkled these out onto the matrix there. And then that was the piece as I adhered them where they were. And the act of being a tree implies the tree. Again, another painting. Didn't like it, tore it apart. So this one, I saw it on the floor and I was like, oh, wow, it's sort of doing that banding thing that I like when I do outputs on printers and there's something plugged in the inkjet. And then I was like, oh, wow, this looks pretty good when I stretch it on a stretcher. I'm going to make it really long. That looks great. It's eight feet tall, four feet wide. It's really impressive. And then I went to hang it and something happened. And those two things, I laid them down on the ground to hang it and I was like, oh, but this is way better. And so then I tried it the other way. And then when I hang it, it sort of fell off center. And then I found that this was a really compelling piece. And so again, there's sort of this tactility depth that comes out from layering. So also in Ventura, there was a quilt show. And I, at this point in February, really hated quilts. I mean, I had this. I'm from the Midwest. So it's like Sunday morning, you go out to the quilt show and it's horrible. It's like everybody smells kind of old. And it's not so good. But so this quilt show was like the anti-quilt show. It was incredible. Like this is, it's the Eiffel Tower. These are cut out and glued together. And then this thing is an amazing quilt that was done that has circadian rhythms. And then this is actually, I don't know if anybody studies psychology, but these are your sleep cycles. I don't know if it resolves up there, but you can see there's some stitching that goes across. So again, you can sort of see like, oh, there's pixels and there's vectors. Awesome. So then this is a little detail here, again, with the sort of more vector based things. And now here's the part where it gets really neat, right? So you've got these women who now, instead of doing it the traditional way, they're saying, okay, we took this photo in Japan and now we're each going to do a panel and then paste it online. And then come together and then sew it together. And this is what they made. So each one of those sort of larger boxes, like, let's see, like in that area, that's one person. That's one person. Anyway, this is another quilt, just some banding. So this one really spoke to me and it's, it's screen vector file. And, you know, it's like, wow, this is very much, you know, this could be done in SVT or, you know, whatever, in Inkscape. And so even the content starting to change, this is a Golgi apparatus or Golgi apparatus. Like, you can only get these, you know, you can see them under microscopes. And so this is now content for quilts, another scientific exploration at a pretty deep level. Now here's something really neat. This woman printed on fabric. So this is more of like a bitmap, but then over the top of it, you can see sort of there's like some pixelation, but then she's going into it again. Oh, let me try that again. Sorry, guys. And so you can sort of see where she's, she's having the stitching over this printing that she's done at her, at her inkjet computer at home, which is really pretty neat. Again, here's sort of some, some running stitches. You know, got these sort of boxy patterns. And then this is hand drawn plus stitching. So again, using a pen with cloth. And then what I talked about before about, about tactility, this show was really inspiring for me because they had these little blocks where the, the quilters actually made little pieces that you could actually touch and that's unheard of in art museums. So that was really cool that you could actually have similar experience to the people who made the thing by touching it there. So again, just more little pieces. This is a detail of homemade cloth. It's all scraps that have just been like sewed together and then it's new cloth out of old cloth again, recycling. That's sideways, but this is Robert Morris from the 70s. Now the 70s and late 60s are really important because people got into soft sculpture like Klaus Oldenburg and Robert Morris. And then also in 1971, it was the first time in an American museum at the Whitney that they actually exhibited quilts. So that was the first time it got in and then in 1977, the first textile and quilt museum opened in San Jose, California. So there's a history of art quilts very close to where I live in California. So if you go back way back to 8000 BC, you have these types of patterns that were on Japanese pottery. And then basically what happened is that they up until about the 18th century, cloth and thread was really, really valuable. And you mended your clothes and you use these patterns to sort of mend your clothes. So this was like a more utilitarian and functional thing. But then closer into the 19th century, cloth and thread became more available. Remember this pattern. Okay. And so what would happen is all the guys that were warriors became firemen because they had to do something with all of the warriors that were around. And there was a lot of fires in Japan at the time. And so what they would do is they would dip these cloaks in water, turn them inside out and put the stitching on the inside, go save the world, and then flip it on the other side and have a parade. So then by having this functional coat that was thick because it was stitched together so much, those stitches then became sort of a status symbol. And it went from being something that only poor people had because they couldn't afford new clothes to something that was admired. So keep that in mind when you're developing software is like, ah, nobody likes this right now. But if you can sort of hit that like cultural, like important thing where you keep making these conferences and keep doing that, there's a point where something's going to switch and everyone's like, oh my God, this is amazing. Why aren't we doing this? So once this happened, I was like totally inspired and I started to see like ones and zeros and grids and graphs and everything everywhere. So I was like, my chair, oh my God, it's woven. Ah, my blanket. Ah, it's pixel. You know, I was getting fired up. So then I learned to knit and purl. So you got ones and zeros. You got a purl stitch and knit stitch. This is all knit. So then you've got, you can do like bitmaps on your sweaters. I mean, that's what that is, right? So then I did some more research and I actually found out that your card bloom is like the thing that Babbage used for his difference. And I was like, what? So that was kind of mind blowing and awesome. So there it is. Look at that. That's pretty neat. So then to like yesterday, Susan showed me this thing where it was like a mechanical slide rule for seamstresses and tailors. Check that out. It's like steampunk for sure. Right? You got like this like Victorian like contraption to measure things that they can't do in software yet. It's like 18, like the date on this is, I don't know, 1888. Pretty rad. So this is a big sculptural piece that I did. This is 17 feet by four feet and we're good. Okay. 17 by four and it's checks, right? So instead of shredding them, I decided to cancel my accounts, throw them in the air and then sew them together. So 1500 pieces of paper and took a month and a half. So while I was doing this, I was going absolutely baddie. And I'm sure that you guys that are developers, I've had that and you need to do something else. So I started putting other things through the sewing machine and I started like sewing everything. It's just like bits of paper and you know, all these stuff and I'm like, why is this so interesting to me? And then I'm sitting there and my computer screen is like ticking over and over and over and over. And then this image pops up from like 1999 was like, oh my gosh, that's a vector drawing I did in college. That looks a lot like, wait a second. That's exactly the same thing. So then, you know, I've been exploring that and doing more and more with it. And this is like some sewn tree bark with some paper and things. And then I started quilting and that was really strange. But again, if you sort of look at it, you can sort of see with the digital influence where you've got these, whoa, you know, you know, these vector areas here that are like prefab and stuff. And then the stitching is done. And so then I felt like these old ladies, I was like, what the heck am I doing? Why am I responding to this? Like this is my future, right? Wrong. This may be what you think. But remember, I told you, remember that pattern? Okay, this is where it's going from. We got Amish quilts from like 1890s to 1940s right now in the D Young Museum in San Francisco. If you're there, check it out. It's going to be there till June. We're going to go through these quick. Think about what I was talking about. Boom, boom, boom, boom. There's this pattern again. Huh? Whoa, there we go. That's what that's about. This is why I'm responding to it. Anybody remember Atari, right? It all looks the same. So this is my youth. Then we got Tron, right? And then you got these sweaters that came out in the 80s and you're like, these are awful. Like what? Oh man. Tumbling blocks again. So this is the actual patterns. I like, look this stuff up. So these are sweet, right? That's that sweater pattern. Like this, that's this. Pretty cool, right? So that leads me to the interwebs. Give me one sec here. So I'm just going to play one little game while you guys are waiting. Press the space bar to begin. You guys remember this? Oh, well. So that's the aesthetic, right? So we've got these people that are sort of between 25 and 35 that have this really strong digital sensibility. And now they're doing things on Etsy. Now, if you go to Etsy and you search for video games, you'll be surprised at what you find because you find Skaft sculpture and you find like computer dork stuff and you find like Lego mushrooms from Nintendo and all these things, right? So that's that's our like folk tradition now. That's folk just means of the people. That's what we're doing, right? So move on. So there's a bunch of artists that I've been sort of researching now that are kind of in the same vein. And Rachel Beth, and I'm going to butcher her last name, Egan Hoffer, I think or Hoffer. But she's making a Wii game that is like dance dance revolution. And so if you miss a stitch, it's like, you know, and you just keep going like this. And she actually has a pretty awesome demo like you can check it out. So she's she's got it's called knitting with like the little wee eyes like isn't that great? That's pretty awesome. And then this is my friend Jackie Gordon. She does like the sound installation with these soft sculptures that are really beautiful and and it's kind of, you know, it's environmental, but she's like making things and then, you know, she's also creating environment with your with your ears. And then this is Stephanie Sijuko. I saw her her piece in 2008 and the copy left and the CC guys will love this because she was basically doing knockoffs and crochet. So she's got like the Gucci purse like bam, check that out. I'd rather have that anyway. And then this is really neat. You forget where I'm from. It's an open source embroidery and she actually has the embroidered digital commons, right? And this is like right up your guys alley and she's, you know, in the same thing. It's like the notion of digital commons where the digital is common or rather what is digital is common to all, right? That's just the first sentence. So then, you know, we've got the HTML patchwork project. And that's actually getting built by like, however, it was 216 people all sending in their hexagon. Cyber thread.net is pretty cool. They do these things called consumption quilts where whatever you eat in the day is quilted in. So that's like potato chip bags and all that kind of stuff. Knit and it is a really cool magazine. It's like the new age of knitting and there's like a whole bunch of guys and girls that are into that. That's me, Nintendo. Instructables, really cool DIY site. Check it out. Maker fair go. Last little thing is all this is on the wiki, which I also just learned to do. Thank you, John Phillips. And you can check that out. It is the new folk tradition on the create wiki and thank you. Thank you.
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I discuss revivalist trends in art with relationship to the hand-made and folk tradition, specifically in fiber arts. Innovative artists, having digital fluency, easily navigate networked communities and collaborate openly. By comparing pixels to patchwork, vectors to stitches, bitmaps to patterns, and layers to quilts, they investigate the overlap among a variety of disciplines.
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10.5446/21384 (DOI)
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Okay, so good morning everyone. Welcome as well. I'm sorry because of the delay of the laptop. We thought it died but what actually happened is we stacked two laptops on top of each other and there's this little magnet inside that makes it turn off. So my laptop screen was turning off and on and off and on because it was sitting on top of the other one. But anyway, it works now. It didn't die so I'm happy. It's a good start of the day because my computer is still alive. So I'd like to start with what a quote from actually Oscar Wilde, the picture of Dorian Gray, 1890. People know the price of everything but the value of nothing. I think a lot of people can relate to that. But what is value? How does value relate to prices and our economy? Why is it, for example, that water which is more useful than diamonds is a lot cheaper than diamonds? They call this the value paradox. So our empathic values, sustainable values, social values, shared values integrated in our economic systems. I think there are no easy concluding answers to these questions but I think we are at a point in time where we can really shape the economy right now and we can create a more relational economy, a relational system where our values are more based on relations with products, people and the systems we work in. So to achieve these relations we need openness and transparency. So in this presentation I'll show you some context and projects which I'm working on which relate to all these questions but also why it's important that this is something we have to ask now and that we have to deal with now. So is there anyone here who knows what this is? Yeah? Shot really loud? No idea? Now? Toaster, yeah. So I think looking at this product and this toaster has been made by this guy over here, this Thomas Twates and Thomas Twates went into a shop and knew the price of a toaster because he was going to buy one and he was going to buy one for I think three or four pounds and he asked himself how is it possible to make something like this for three or four pounds and what's behind it? What's the story behind this toaster and how do you make it and who's making it and what do you need for it? I think it's a really good question because it's also a question which we don't ask that much ourselves anymore. And what came out of that is this beautiful toaster which looks kind of alienating because we are used to have all these and you see it there in the shop together with all the other toasters. We are used to see these masperduce toasters as objects we use every day and we don't ask about how is it made and what's around it. But with the toaster Thomas Twates made, you can actually see how it's made because he took it very seriously. So what he did, he went into the mines and got the iron ore and he actually found a patent online of someone who found out how to get iron out of iron ore. There was actually someone who was playing around with microwaves to try to get iron out of iron ore. So he used that and from all these steps and getting further into this process, the technical process, he actually learned a lot about the stories behind all these, you know, the people working in the mines. So it became more like this project about the stories around stuff. So the toaster tells a story and it's the beauty of the product I think is that it's transparent, that you can see what's behind it. So it's an industrial product and it's, you know, we kind of got alienated from all these products. And looking at industry when it started, this is around, I don't know, there are probably a lot of people here who know the wealth of nations, Adam Smith, 1767. And Adam Smith is the one, this is the first book that actually describes the economic systems. And Adam Smith was describing the self-regulating market. He was describing the vision of labor and the vision of labor is exactly what happened with the toaster as well. You know, everything became processes. And you have some people working on that aspect, some people working in the mines, some people working somewhere else on having the fuels to make the machines work. So there's another man called Milton Friedman. He's a true capitalist who has a really, I think a brilliant story about a pencil where he explains the division of labor. And I'd like to show you the movie of Milton Friedman explaining this. Look at this lead pencil. There's not a single person in the world who could make this pencil. Remarkable statement? Not at all. The wood from which it's made, for all I know, comes from a tree that was cut down in the state of Washington. To cut down that tree, it took a saw. To make the saw, it took steel. To make the steel, it took iron ore. This black center, we call it lead, but it's really graphite, compressed graphite. I'm not sure where it comes from, but I think it comes from some mines in South America. This red top up here, the eraser, bit of rubber, probably comes from Malaya, where the rubber tree isn't even native. It was imported from South America by some businessmen with the help of the British government. This brass ferrule, I haven't the slightest idea where it came from, or the yellow paint, or the paint that made the black lines, or the glue that holds it together. Literally thousands of people cooperated to make this pencil. People who don't speak the same language, who practice different religions, who might hate one another if they ever met. When you go down the store and buy this pencil, you are in effect trading a few minutes of your time for a few seconds of the time of all those thousands of people. What brought them together and induced them to cooperate to make this pencil? There was no commissar sending out orders from some central office. It was a magic of the price system, the impersonal operation of prices that brought them together and got them to cooperate to make this pencil so that you could have it for a trifling sum. That is why the operation of the free market is so essential, not only to promote productive efficiency, but even more to foster harmony and peace among the peoples of the world. Well, a true capitalist, I would say. Also, he brings this really romantic story about the free market and people not knowing that they are working together on this pencil, but are connected in a way that creates this social bonding, blah, blah, blah. What he is talking about is the invisible hand, the self-regulating market. The invisible hand is the hand, and Adam Smith was already talking about it. There are some critics about the interpretation of that, but the invisible hand of the self-regulated market became this thing everyone was holding on to, because isn't it beautiful that everything works by itself? The problem with that is that you also, that is an untransparent way of working. If you don't know if somebody is working, you know, the vision of life, somebody is working on a piece there and somebody else is working on a piece there, they don't know. They have no shared value in the whole thing. The invisible hand takes care of that. So what if this untransparent situation creates unfair situations? And I think invisible hands can be really unfair, and I think some British people here might agree with that, because if you look at production and products, they become so complicated and it becomes so impossible to trace all these parts, because look at this car. It's a beautiful car, but it's an old car, and it's actually a very simple car. The cars right now are much more complicated. Can you even imagine that all these pieces have suppliers, and all these suppliers of these pieces have suppliers, and those have suppliers again? So it's exponential, it becomes exponentially complicated to trace where stuff is coming from. So the cars right now have electronics as well, and when you put electronics into the equation, it becomes even more complicated. And there's also a lot of stuff going, you know, being unfair about these electronics we use. I can show you that in the next short movie. I'm on my way to the eastern Congo, one of the most dangerous places in the world. Congo has been a major source of natural resources for the mobile industry the last 15 years. I've heard that in mind, Steven the Jungle, children are working under horrible conditions. I want to see where these minerals are coming from, and to see with my own eyes if they are financing war. This is chance. He's 16. He says that for the last three years he's been working in Besie, the biggest illegal mine in Congo. He wants to take me there. You see, this is horrible, what they are living is really horrible. Four years ago this place was nothing but jungle. Today 15 to 25,000 people are working here. Different armed groups are fighting to gain control over the mine. These teenage boys stay down here for several days, digging out minerals essential for the mobile industry. Mines like these are few years away. In the last 15 years more than 4 million people have died. These minerals end up in mobile phones, like my Nokia. Does that make me responsible? We are all responsible, and you know that all this is going into you. We must be revolted by this situation. We are a human being. Get out of the mine, Nokia. Okay so, of course this is through the eyes of a documentary maker. There's a lot of drama in it, but there's definitely a point here I think. Looking at the situations we create around these products, making these products, it's so complicated to even know where stuff is coming from. Nokia for example in this movie is one of the targets of the documentary maker. Nokia cannot say they have conflict minerals, conflict free phones. There's not one phone provider, phone developer in the world that can actually say that they have conflict free phones. Because it's impossible to trace. You see here the difficulty of the tracing in the Congo itself. It's not only, you know, this is about the mobile industry, but it's not the mobile industry itself. It's the whole electronics industry. You know, tantalum, one of the minerals they showed here in the movie as well, is used for capacitors. And capacitors are in all electronics. So, also cars. So I went to this website called slavery footprint.org. And I don't even have a mobile phone actually, but I do have a computer. I do have a lot of electronics in my house. So what you do, you fill in all these electronics devices you have. And the website then calculates how many slaves are working for you. So I got 60 slaves working for me. Well, obviously most of them are working in China. But some of them are also working in the States, South America, Africa. It's all around the world slaves are working for me. But the problem with, you know, slaves and the whole term slaves is that, you know, what makes a slave a slave? And what is slavery? And what is the opposite of slavery? Because when you look at the opposite of slavery, I think we're talking about liberty. And what, you know, if you look at one of the brightest people ever lived tells us about liberty. He actually says, it's a term whose meaning is so porous that there is little interpretation that it seems able to resist. So what does that say about fairness? What does that say about openness? If even liberty is so porous that you cannot, you know, you can make anything out of that. But there's one thing I do know. And I'm a designer and designers like to think in solutions. And not so much in question, because we have had, you know, I've been putting out all these questions and all these abstract terms which are really hard to answer. But if you look at unfairness, so you take the opposite of what is fair, I think everybody believes that you have to have action when you have unfair situations. So one of the projects we did is creating a fair phone. And we're still working on it because that's not something you do within one year. But fair phone is a project we started two or three years ago. And what we thought is okay, so if the mobile industry cannot say that there is conflict free, that there are conflict free phones and they cannot, you know, vouch for fair phones, then we're going to make one ourselves. Because how hard is it to make a phone? Phones are being made already. The hardest thing is to make them fair. So we started doing that. And of course you cannot do that yourself. Because I'm not a phone developer. I don't know electronics and I don't know mines. I don't know minerals. I don't know where you can go on and on. But together, if you put it up as a platform, I think we can come quite far. So that's what we did. We started step by step. And one of the things we did was also go to Congo and find out if it's possible to work with mines and corporations where you can actually contribute. Africa. Fairphone is the world's first collective non-profit technology company developing a phone using minerals mined and sold under equity conditions. Recently, Fairphone undertook effect-finding mission to Katanga, the most southern province of the Democratic Republic of Congo. Katanga's soil is full of copper and cobalt, the letter being used in batteries for mobile phones. The Fairphone crew visited various parties in the mining industry, from high-ranking officials to artisanal miners. This short film shows you some highlights of a very successful bill, Bumpy Expedition, towards the heartland of Congo's copper belt. We are in the Camillombé quarry where artisanal miners produce cobalt. So there, we have a very deep pit that can be 60 meters high, and there are ramifications that people can go through. And to protect themselves against rain, artisans put their cows. So when it rains, the rain can't attack them from inside. And there, they are working. And generally, in such cases, they don't come out immediately. They make reserves there, and the days of their work, they come out with the same day. One has to work to change phone a party on Kongo. Yes, I was wondering if you would take my phone to Kongo. It's not a product. It's a gift from me. It's a gift from me. I'm not going to take it from you. I'm going to take it from you. Okay. The answer is that our objective is to be honest. We have a channel. We have a phone call. We have a phone scandal. We have a phone call. We have a phone call. I'm not going to lie. I'm not going to lie. I'm going to lie. No kidding. I'll leave you because if you leave, I Constitutional Jeent빈 men can hear something chocolate So, I work for a media lab in Amsterdam. It's a non-profit organization called Vax Society. And Fairphone is one of the projects we do. If you want to know more about the project and look at what we're at at this point, you can go to the website and look it up. At Vax Society, we have a mission. And our mission is to give social cultural meaning and value to technological developments. In a way, it's looking at social innovation. And when you look at the projects we do, one of the principles we work on a lot is reciprocity. And reciprocity is also very much connected to fairness. So in a way, all the projects we do has this fairness component in it. And also one of the things we think is that with close systems, you cannot create this reciprocity. And I really like this quote from Makeson. I think a lot of people, or some people here might know the manifesto Makeson made. And one of the quotes in there was, if you can't open it, you don't own it. And I think ownership is very important. Because when you feel ownership, you can actually create relations with the stuff you use. So at Vax Society, we have several labs. You can see the labs as research programs we do. We have a creative care lab. We have a future internet lab that focuses on the future of the internet. Urban Reality Lab is focused on how you deal with urban development and location-based applications and virtual layers. And one of the labs I coordinate is the Open Design Lab. And of course, the Open Design Lab has a mission as well. And the mission comes down to that we try to bridge the gap between the virtual world and the old industrial models. Because in the virtual world, we have this network culture. And in the old industrial models I just showed you, they work on a totally different basis, totally different principles. So this is what happened with the industrial stuff in our cities. Division of Labor actually took care of that. And what you see in the back of these industrial buildings is what came out of that. It's the knowledge economy. And the knowledge economy is mainly about information. And information moved away from controlled consumption. What happened is that we had a digital revolution. And we had this digital revolution. This took place. Information and industry got separated. Well, what do I mean by that? When you look at this, people reading books, information was part of the industrial system. You needed books to put this knowledge on. You needed film to put films on. So you had all these artifacts and you had machines to be able to create these artifacts to distribute knowledge. That's where copyright also came in. So copyright is very much related to all these industrial processes. So with the digital revolution, that totally changed. So information is produced in a very distributed way. And people are both the sender and the receiver of information. And this is, by the way, a snapshot of the Internet, I think, two years ago or something. So that digital revolution made this possible as well. This is Napster, one of the first versions, I think. And this was a pain in the ass for the industry because it totally bypassed the system they created. And what they did was, of course, their first reaction was create this control system. But we went on and we did this. And now we have open data. You see all this creation of openness within this network culture is getting more and more. Many people here talk about it already, so I won't go into that too much. But this is when it gets really interesting because Pirate Bay, I think, two or three months ago opened on the side something like what's it called, Fisibles. So on Pirate Bay, you can actually search for physical objects, you can download the files, and you can create them with machines. These are blueprints of products. So at Pirate Bay, you can actually download products now. And then this happens because products now are partly moving away from this controlled consumption as well because it's becoming part of this digital system. We can spread around all this information about products. You can spread around the files to actually create products. And now this shit really hits the fan for the old industrial copyright system because it becomes integrated into this whole network culture and the physical world. So what is that that makes it possible to download products and then make them? Well, digital fabrication is a big part of that. Most of you might know 3D printing. This is a laser cutter. So somebody downloaded the file and with that file, you send it to the machine and the machine can create, in this case, a chair out of that. So there's the chair. So the big thing about this digital fabrication, of course, is the way you can distribute it. These machines are capable of reading digital code and controlling the machine to make the object. And of course, these machines and making chairs is not what it is about. It's about creating access to this means of production because you can actually download yourself silly from Pirate Bay or Thingiverse or whatever and have all these files on your computer but you can still not make a product because you need machines for that. So one of the developments in that is, for example, FabLab. I think FabLab Fabrication Laboratory is one of the biggest distributed maker systems and infrastructure which gives open access and which is growing really fast at the moment. And I'll show you a movie where Neil Goschenfeld, the founder of the whole FabLab idea, will explain the idea of FabLab himself. We've had a digital revolution but we don't need to keep having it. We can declare success we want. What's coming now is the digital revolution in fabrication. My colleagues and I started teaching a class called How to Make Almost Anything and the idea was just that. It's a program looking at how the digital world relates to the physical world. And one of the core things coming out of the research is the idea of digital fabrication, making the Star Trek replicator and assembler that makes anything you want by building the atoms on up. This is designed where you put in the millions of dollars of equipment at MIT or like the mainframes of digital fabrication. We can make anything we want using those tools. In 20 years we'll make it so you can have it in the home. The FabLabs are in between. They spread all around the world letting ordinary people create technology from South Africa to the north of Norway and from rural India to inner city Boston. Instead of spending vast amounts of money to send computers and energy and communication around the world, you can spend much less to send the means to create it. Energy, communication, computation, just to say the words they sound big, they're being tackled as billion dollar mega projects top down. FabLabs is tackling them from the bottom up. We're just finding so many people with such interesting inventions and such great ideas. Sharing that is where I see this go. Okay, so that explains the whole idea of the FabLabs. This is a map of FabLabs around the world which is pretty old actually because also here in Berlin with Open Design City of course you have a FabLabs as well. Even in Holland they, I think around 10, 12 FabLabs already popping up. The great thing about looking at fabrication this way is that you share knowledge on this global level and you have the production on a very local level. So you can actually create products on this local level and local needs and share, but share the information about making it because you have similar machines on the other side of the world. Share that information and other people can use that as well. So one of the examples is Afghanistan, in Afghanistan they make Wi-Fi antennas together with also Kenya and MIT in the States to be able to send Wi-Fi signals from one village to the other village so you can connect all the villages and all the nodes. And they create these antennas for around 200 euros so you can make them yourself instead of the 20,000, 30,000 Cisco system Wi-Fi transmitters. But another project they're doing is in the States it's on modular housing with digital fabrication so how to be able to create your own house. You can actually build a FabLabs with a FabLabs this way so if you have a machine and you have the wooden stuff you can create your house. One of the projects we're working on at Wax Society because at Wax we also have a FabLabs is this prosthetics project we do together with Indonesia and what we're trying to do is to create a prosthetics for under $50. A normal prosthetics, lower leg prosthetics is around the 5,000 euros. When you look at Indonesia for example where you have bamboo and local materials which are pretty strong you can use bamboo instead of titanium. Of course it's not as sustainable as titanium but it's a lot cheaper. The real challenge with this kind of product is that we try to design in such way that people can create them themselves either in workshops or in sessions where you get guidance in it or alone but the real challenge is that. So think about how do I create products that other people can create so you're kind of making blueprints for other people to be able to create their own products. But not only prosthetics, housing, these big things are happening in FabLabs. A lot of designers come there and make their stuff, dresses, we have in Amsterdam a lot of textile students and fashion designers are coming to the FabLabs to work with textiles and to see what happens if you put specific stuff under the laser cutter for example because they're not allowed to do that when you go to a prototyping place and give them a job on cutting something. They can cut anything as long as it's not on the blacklist we know. For example PVC which has chemicals and stuff like that. And this is an example of a little boy I think 9, 10 years old came in and he had something on his, he had something wrong with his food so he needed special things for in his shoe to make them a bit higher inside. And he had to wait for a few months when he was going to the shoe repairman or to the shoe, I call that, the specialist. So he decided to do it himself and he succeeded so he made this stuff all by itself in the FabLabs, learned a lot and I think it's a brilliant example of somebody who puts a lot of time into making this because it's not pushing a button and it's ready. But he succeeded in doing it. So what we do also is look at how can we combine crafts and old crafts and 21st century crafts. This is a project where we use mud building and CNC routing together to create all these ecological, to combine ecological building with this 21st century blob building if you want to call that. And so this is, you might notice project, this has been shown at DMY I think last year and a project by Dirk van de Kooij. So you see that also designers are experimenting with these new technologies as well. So if you open up these technologies people find new things to do with it. So hi, I'm Dirk van de Kooij. I'm graduated on the design academy with the project called Endless. It's actually a big robot that is making furniture out of recycled fridges. Recycled fridges goes inside of the machine on the top of the robot arm and it's getting melted and it's so hot actually that it will melt to the former layer that it's been putting down. So it's riding in one endless line or in one endless string, a chair or a table or another piece of furniture. We can pigment it of course like any other plastic you can. But with this layering structure you can do funny stuff like gradients and you can emphasize the way it's been built up. The idea is like retrieved from rapid prototyping when I saw the model that was made with a really old machine and then you can see the ornament or the lines and you can see how it's been built up and I said okay wow this is cool. I want to blow it up to a bigger scale and then make it an ornament and tell the people in the chair really how it's been made. It was much faster like a prototype machine does it in five days in a chair and this does it in three hours and you can use recycled plastic instead of really expensive materials. There's maybe a future ahead for me also with this project. So enjoy. Okay so those are examples of people using these technologies to create solutions for specific problems or to create designs or to create objects. But it's not only about that. I think a big part of the labs and the importance of places like the FabLab or Hacker Spaces or whatever you want to call it is that the making process itself. It brings crafts and making into the environment again. It creates this relation with the objects you use again which is necessary also to create this ownership and this ownership is necessary to take responsibility also for the stuff you do. And also to be able to understand the systems around you. Because making and this is I've read this story about Arkea people creating billies. I think you know billies. You know these really easy cupboards people make and they made a comparison about people who made billies and they put them together and they asked which one do you like most and everyone liked their own billy. They thought their own billy was the most beautiful and they're exactly the same. So anyway if you make something yourself even though it's an Ikea billy you get an attachment to it in a way. So talking about Ikea I think let people give their own meaning to stuff. Own products as well. Hack products. Because if you look at objects and if you get this ownership over objects it's about these experiences as well. And again also the stories behind all these objects. So it's important to look at technology and to hack into it. Because if technology becomes very complicated and I was showing the car in the beginning and the car is you know it's an easy thing and I don't think there are that many people that can fix their own cars nowadays. So that's also the reason why we need these places. We need places where people hack into this technology because otherwise it will be the big companies and the big institutions that will make this technology and you'll be the one that consumes it and have to deal with that. So that's also one of the I think maybe the most important function of these labs and it's also in a city because that's what's happening. You get production much more closer to the urban environment. Some people call it post industrial production. I think post industrial production might actually create these new relations. So what does that mean for a business? Because I think a lot of people and that's one of the questions I get a lot is okay you know find nice story, a bit idealistic and I believe people are altruist but the bottom line is still how do you make money with all this stuff? Well the bad news is I don't know. I don't know, I cannot tell you how to make money with all this stuff with everything that's happening but what we did is we did experiment with it and we're still doing some experiments but just have a look at this model. So I was talking about crafts before the industrial revolution people made products in workshops. The mass production model you get standardized products. What we have now is that people can actually be part of that interactive digital design process. We can create interfaces where people can be part of creating their own products. So if you look, this is simplified but it's a way of looking at what's happening. And we did a project with Drogh Design. Drogh Design is a design brand in Holland which is pretty famous for its high quality design and we were creating this platform. It's not online yet but we're creating this platform called Make Me where we look at how we can create business models around all these new things that are happening. And the main, the basics of the platform is that it's a platform for products which are not made yet. That means that if somebody is going to buy something on that platform, he can still choose who's going to make it, maybe he's going to make it themselves. That's a business model as well. And also, you know, what the product is going to look like because if it still has to be made, you can still have influence on the product. So these are some of the products which came out of the first pilot. You see the cupboard in the left corner? That is, there's an interface created for that where you can actually push at specific places and the cupboard will make holes at the places where you've pushed. And in the back, it generates, so in the system, it generates all these outlines for machines to read the code to actually make this cupboard as well. So you can, after you've made your product, you can choose which FabLab is going to produce it and then it sends it right away to the FabLab. So it's about optimization of the system. It's about having consumers make them part of this design process. And also, it's about how is the designer going to make money on these blueprints which are downloadable and freely distributable. This is another product, I'll go through that. It's a bikini line which you can cut with the laser cutter. And the nice thing about this, and of course the sizes, you can change everything in the colors, but it melts together while it's cutting. So you can put two materials on top of each other and it cuts with the laser cutter and it melts together so you have really high quality bikinis. So how does that relate to openness? For the FabLabs, I think it speaks for itself. But with the stuff I showed you with the business models, I think what's happening is that it's also creating new relations with the people who make stuff. Because it gives the craftsman, either it's 21st century craftsmanship, it's digital fabrication or it's people that make stuff by hand, it gives them a face again. And you can also, you can relay it more to them and it becomes much more transparent. So to me, that's openness as well. But if you look at where I think the really, the main things are happening is when you put something, when you put products online, you create communities around it and you create a context where everyone can collaborate and participate. And then you're talking about open source design hardware products. This is a car which has been developed open source. This is a house which has been developed open source. And these products mainly exist online. This is where the real stuff is going on. And once in a while, there is a momentum of a house that's popping up, which is a version of the whole community working on that house. That's also something we want to do with Fairphone. And we're starting this year to create this open design community where people can actually combine and think and create stuff together with us to be able to produce this product. And I think one of the important factors in that is that we can make this invisible hand I was talking about in the beginning, we can make this invisible hand visible again and create shared value throughout this whole production chain. So when we go back to where I started, I think we still have a long way to go. But I truly believe we have the perfect situation now to create this relational industry based on values. And I also believe that we can all benefit from that. So I'd like to leave it with this. And thank you for your attention. I don't know if we have time for questions. No, it's 11 already. Okay, so one or two questions. No one? Not too early? Okay. First of all, thank you very much. A fantastic keynote. What about the phone? Can you tell us a bit more of when will it be ready to ship or be able to ship the boat? The problem with the phone, it's a very complicated thing to do. But what we did, we simplified it by saying we get one mineral, which is cobalt, and cobalt is used for making batteries. And we focus on cobalt now, so we're in Congo trying to set up collaborations with mining companies or with mining corporations there to actually create this battery. And we have on the other side of the market a KPN Vodafone T-Mobile. We're already willing to sign contracts to take these batteries and put them into the market. So that's where we start. And then, you know, a smartphone has more than 30 minerals, which also, you know, dubious in terms of fairness. So it's a long way to go. We do it step by step. Go on. Thanks. Bas, thank you very much. Due to our schedule, we have to close another session. Thank you. Welcome.
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Against the background of the technological developments that enable small-scale urban industrialization, our relation to the concept of making needs reviewing. Does urban industrialization have an impact on the relation that we have with our products and our environment? Our current mass production system has created a huge dived between the product and its origin. The production has been divided in processes that are mere parts in a larger chain of events. As Marx already predicted, the worker who cannot add value of his own, and is not appreciated by others about, will alienate from the products he makes, his environment and, in the end, himself. To create, is to give meaning, a reflection on ones' "da sein". In our current digital world, "making" has regained a new and important role. Internet has enabled the developments of new "make"-principles that are based on openness, social involvement and transparancy. New professions arise on the crossroads of virtual and physical realities: the crafts of the 21st century. With digital technologies physical products are created. Fabrication facilities like the Fablabs enable us to globally distribute knowledge and locally produce this into physical products, based on open design principles. Think of open source 3d printers for do-it-yourself product developments. We live in a time in which people can give meaning to products more than ever. It is impossible to imagine contemporary society without the resulting increased transparency and freedom.
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10.5446/21385 (DOI)
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So thank you all. I am quite delighted to be here. And here we go. Looking forward to the next few days, lots to learn and a really great lineup of speakers. So what I'm going to talk about today is open innovation and the contribution of non-experts. And there's some definitional work that needs to happen for this. So my primary goal here is to define open innovation as tied to non-experts. And I'm using a specific definition of non-expert. It's not about whether or not you're good at something. So it's about lacking official credentials, being unaccredited, not being recognized by institutions as being an expert in a particular field. So this is an important distinction in part because what I want to do is I want to draw attention to the invisibility of non-experts and their contributions and try to surface that in the hopes of understanding how we can cultivate more innovation and more, particularly more disruptive innovation. So I look at three communities. I look at hackers, makers and students, both hardware and software hackers. And the reason I throw students in there is I'm talking about undergraduates sort of before they become credentialed. I call them hackers because they have the audacity to think that they can make a difference even when the institution basically wants to tell them that they're not ready to do anything substantive. And so across these three communities, the collective ability to contribute to innovation is what I'm really interested in these days. Sort of odd to talk about hackers here in Berlin, which is kind of like the epicenter of everything going on, but it's also great to be here. So there are three elements to this discussion. So the first is a book that I'm writing on the topic about hackers and disruptive technology. The second is a project that I'm running at my university called Hackademia, which is an attempt to foster more innovation by non-experts to come up with a model for that. And then the third element is something that I'll talk about a little later. So the reason I'm using this particular definition of non-expert in terms of the credentialing issue is because I'm talking specifically about the limitations of institutions, both academic and business institutions. How they themselves are credentialed, what they value and the structures that they evolve, which ultimately end up squelching innovation. And so this is also part of a larger project to think about how to revolutionize higher education in light of technological change. So I've been working in places like that, actually not usually as pretty as that, but in educational institutions for about 20 years teaching at universities. And they have a lot of boundaries. And in the same way that, say, technology has really reframed journalism, that change is coming for higher ed. And by and large, I would say most universities, kind of like ostriches, they're ignoring the change that's coming and so trying to daylight some of that. Anyway, so institutions have boundaries and you can counterpose those boundaries and that closeness to the idea of openness and open innovation. So this talk is, so you can see this talk about the power of open innovation, but the flip side of that is also about the limitations of institutions. Okay, thanks. So the, I have two bottles of water and I guarantee one will end up on the ground. Okay, so I do have a little confession that I have to lay out here. I was rehearsing this talk with a friend of mine earlier this week and she said, you know, you really need to tell them a little bit about your background, which is, I don't really, just not my first impulse. So I am a professor. I am a professor in a college of engineering and I am a full professor, which means in the American education system, there are no more promotions that I can get. I'm done. Which is great, great place to be. But while I am a professor in engineering and I do have a PhD, but my PhD is actually in literature. So that's my confession there. So I sort of operate in this world where I don't have the official credentials to do what it is that I do in my day job. And so the sort of evolving conflicts there, I think inform a lot of what this project is about. Okay, so it's become obvious over time that experts aren't necessarily the best problem solvers. And on one level, we know this, right? We all know this. But as a society, we don't operate as if we know it. And certainly universities don't operate like they know this and by and large, neither to businesses. So experts may not be the best problem solvers and that means that our problem solvers, our best problem solvers don't necessarily come from that population of experts. But we organize our institutions and our processes around the prioritization of expertise. When actually what we need to solve really tough problems is a dose of non-expertise. We need a kind of fresh vision. So one of the reasons I want to recuperate the non-expert as an innovator is because I think that non-expertise is a kind of power. It's freedom from boundaries and the limitations of institutions. Also non-experts as innovators, they're rule breakers. And so in the populations that I look at, well, they are literal rule breakers. There's a lot of laws that get broken in the hacker and maker communities. I'm not passing judgment on the breaking of laws or the justness of certain laws. But so there's the literal rule breaking that happens. But then the other reason that I sort of like this phrase of rule breaker, and it's because I want to call attention to it because there is that kind of power play, okay? And it's a political act. It's a seizing of power and pushing back on institutions that give credentials. So for example, open software and open hardware, they've changed the nature of the kind of hacking that we can do and the problems that we can solve. We don't need a kind of rarefied expertise. There's been a democratization of technological tools and that bolsters the rise of the non-expert innovators. So in a few minutes, you're going to hear from some of the open challenges. And those are also really great opportunities to think about how some of these more democratised technologies can allow non-experts to contribute to change. So the other reason that I like to use the phrase rule breaker is because of the cultural and economic power associated with being technical. And this probably does come out of that whole literature engineering split. So I use that, the frame of rule breaking as an act of cultural disruption because it's a matter of people claiming the ability to do things that those formal models of expertise totally exclude. And it's powerful for people who don't have credentials to call themselves technical when being technical means something in terms of your ability to get a job or to be well compensated. So non-experts, rule breaking innovators, got that. But they also contribute specifically to disruptive technologies. Not just innovations but the creators of particular kinds of technology that tend to be disruptive. And that's really what differentiates them from people who operate within institutions. And so the reason why I'm looking at these three communities is I see them as disruptors outside of those institutions. But also, so just as a sort of step back from, I put a bunch of people under the umbrella of hacker, the definition that I'm using, I try to avoid definitions actually I'm much more interested in the commonalities across communities rather than the differences. But the definition, sort of thinking about people who break things and also people who build things, people who look at an object or a system or process, and they don't necessarily get frustrated by the ways it doesn't work for them. Instead, they think, well, how can I change this so that it does work for me? And then they hack it so it works. Another way to think about it is people who don't know any better. And so they just make things better. But one of the things also that happens is when you get these non-experts is they don't necessarily understand the boundaries of the problem because they are existing outside of expertise and institutions. And so you bring in experts and they really understand the problem and they know how to frame it and what language to use and what the prior work is. Maybe they get a little interdisciplinary, maybe they sometimes get a little out of the box thinking or I guess with this, be out of the circle thinking. But for non-experts, they don't actually know how to even articulate the problem. And that's where the real power and their solutions often comes from. And that's often really the best pathway that we have to creativity. Okay, so we've got non-experts, rule-breaking innovators of disruptive technology. I'm going to spend a little time on what I mean by disruptive technologies. So this slide is kind of an eye chart. I don't really mean to test your vision. So I'll go ahead and talk through it. But basically, the value of a non-expert. So they're outside of institutions like academia or industry. But those institutions, they have very real and tangible disincentives for creating disruptive technology. So what you see in front of you, it's a little tiny piece of a model by Clayton Christensen who writes about innovation. He writes about some of the characteristics of disruptive technologies. They have less functionality, tend to be less expensive, be able to new user communities. And so if you think about the kind of work that, and the way work gets done within universities and then also within industry research settings, there's a mismatch. Okay, so in terms of less functionality, the way that universities work is on research dollars, is at least in the US, and increasingly actually globally. So if my students, if my graduate students try to do something where they're coming up with a technology that has less functionality than something that's pre-existing, that's not going to constitute new knowledge necessarily. And if it's not new knowledge, I'm not going to get a grant for it, and they're not going to get a PhD for it. And so my institution is very specifically telling me this is not something that we're going to prioritize. In terms of being less expensive, and this is where I think some of the disincentive in business comes in. So in a few minutes, I'm going to tell you about a project that some students of mine worked on developing a low-cost ultrasound machine. They did an awesome job, and I'm going to talk about it at length. So they came up with a bunch of really great user interface pieces and other terrific elements, and then we shopped it around to manufacturers. We went to Philips, we went to GE, we went to other ultrasound manufacturers, and we said, hey, look what we did. We'll give it to you. It's free. Take it. But we really think that this will help save lives. And they just weren't interested. And eventually, in one of the meetings, a vice president said, he said, well, you know, we could make cheaper technology. That's not actually the problem. We have the technology to do that. We can make it cheaper, but it would not support the cost of our sales force. So I thought, well, that's a broken model. But it's also a structural disincentive to coming up with disruptive things. And then in terms of new user communities, I mean, they're challenging. So when you think globally, and a lot of my work is developing low-cost technologies for low-resource environments, manufacturing and distribution work differently. Advertising also works differently. And then you may be looking at a high-volume, low-margin kind of product that's really challenging. So again, within these institutions, lots of disincentives to come up with something that's disruptive. So one of the other elements, I think, that's really important to pull out of this idea of non-expert communities. So they're rule-breaking innovators, disruptive technology. But they also embrace the idea of technology remix. So it's not necessarily cutting-edge research in well-funded labs where you have access to really expensive and advanced equipment. It's often about using older technology in new ways. And so a willingness to engage with this notion of technology remix, which does not fit in to traditional models of practice within institutions, sort of taking things apart, putting them back together in new ways. Maybe there's not any new IP. You're not going to get any patents, which are going to add value to your company. You're using older stuff. It's not necessarily bleeding edge. All of those things are remixed, and it's disruptive. So in the same way that media remixing has been disruptive to conventional schema of copyright and media business models, technology remix is similarly disruptive. Okay, so we have this model of disruptive innovation emerging from non-experts. And so I've been collecting these patterns of remix, disruption, and hacking. And this started about 12 years ago. I was doing a bunch of work doing research on patterns of technology adoption and adaptation globally. And I spent a lot of time in Central Asia. I did about an eight-year study there of how technology was diffused and adopted and adapted. So this was, so back in 2000, sort of just setting the stage here, I was living in Toshkent. And it was a pretty big city, about 3 million people. And so by December of 2000, there were 12 places in the city where you could go to get access to the Internet. So there were 12 Internet cafes. Theoretically, there were ISP, so you could get dial-up in the home. But it wasn't especially accessible. So that's just a little bit about the sort of time and place of what's happening. And within this context, you know, people, they've got a martial different skills in order to figure out how to use this new technology. There's a lot of collective sharing. You know, the slide that you're looking at right now, there's three people huddled around one computer. And what they're doing is they're combining their skillsets. So maybe one person knows how to type, another person has the foreign language ability for what they're trying to learn, and another person might have domain expertise. But combining the skillsets and thinking about what people can do, and what can they learn. So one of the things that they can learn is they can learn how to build a LAN. So I was interviewing a group of maybe 14, 15-year-olds, probably about 2004 in Kyrgyzstan, and they loved to play games. It sort of seems like a universal, and they really loved to play Counter-Strike. That was their favorite. So in addition to internet cafes, there were a lot of game cafes that they could go to to play at. But, you know, it cost money, and also if they wanted to play at night, it was, you know, the parents didn't necessarily want them going out late at night, but they still wanted to play. And they had computers in their home. So what they did, they lived in a big old building like this, and they took cabling, and they ran cabling from one apartment down a few floors and over a few apartments to the next one, and they hooked themselves up together into a local area network so that they could play Counter-Strike in the middle of the night, and their parents didn't know, which was great for them. But also a really great hack. I mean, they didn't have any network engineering background, but they did it. So some of the other hacks that sort of emerged from this pattern of travel is the way that people responded to crumbling infrastructure. So when you have, say, a telephone infrastructure that is somewhat lacking, the person who lives off to the side there takes their phone in the middle of the day, during the day, rather, runs it out, hooks it up. If you want to make a call, you go give them a few cents. You make your call, and at night, they take that phone back in. And so that person does not work for the phone company. Okay? There's a completely unsanctioned business trying to figure out how to close that telecom gap. So these are some of the patterns. One of my, so that's all stuff from some of my field work. Another great place to see stories like this is off of this website, Afragadget, which I'm sure many of you are familiar with. And so this is their latest, the latest post is about this 13-year-old boy who was responsible for taking care of the family's animals, the herd, which is typical. And they live in an area with a lot of lions, and the lions like to eat the cattle, because they're tasty. And this boy figured out that when people were out walking with flashlights, the lions didn't attack. It turns out, lions are afraid of people, which I did not know. I feel like I am much more afraid of lions than they would be of me. So he came up with this idea to take old LED bulbs from flashlights, hook them up to a car battery, long offense line, and have them go in an irregular pattern that would mirror someone walking around. And in the months since it's been installed, no lions have eaten their cattle, whereas their neighbors have suffered losses. And so you could actually build a lion-proof fence, which is expensive and time-consuming. And so this kid came up with this amazing hack. All right, so I'm going through, you know, spending a decade or so, kind of just paying attention to some of the commonalities among hackers in their communities. And about five years into that, I started hanging out with the local hackers in my community. And this wasn't for work. It was just sort of, it was just part of my life. And whether it was the hackers in Uzbekistan or the hackers in Seattle or the students that I was teaching, they were all communities where imagination was much, much more important than knowledge. It was imagination that spurred people to figure out how to learn what they needed to learn, had nothing to do with any kind of official expertise that they had gained. So I decided I wanted to figure out what are some of those habits of mind of these people that I termed rule breakers. I can also think of them as functional engineers, not accredited engineers, but functional. And I decided I wanted to identify and extract those habits of mind from these folks in the interest of helping more people break more rules. So that's really what I want to do, is help more people break more rules. So I started looking at individuals and doing some interviews and working on that book that I mentioned. And so people like this guy, this is a story from the U.S. And this is a guy he lived in Detroit. He had a shop. And he was really interested in metallurgy. And after many years of working with steel, he came up with a new way to make, to harden steel. So traditionally, you heat it for like a week, right, at a temperature. And he came up with a flash heating process. So you heat it for a much shorter period of time, but at a much higher temperature. So the energy savings are enormous, because you're just heating it for a short period. But it also ends up being about 7% stronger. So the steel is stronger. And he tried to get the attention of kind of established professionals in the field and had some challenges there, did finally get their attention. And there's this great quote from one of the scientists at a university where he finally started working, who said, yeah, you know, steel, those of us who work in material science, you know, it's just, it's something we would have considered a mature science. We wouldn't, it would never have occurred to us to actually try to make it better. We figured it was done. So again, the non-experts are not knowing the boundaries of the problem space is able to come up with some really great solutions. And then looking at some of the history around all the ways that software hackers break things, helps us to also build better things. So better software, better systems, better societies, more transparency, and also more accountability. Unpack that sense. But this is another guy. This is a YouTube video, which you can go, I don't have the video linked, but you can go and watch it this evening and impress your friends. It's a party trick of how to get a cork out of an empty wine bottle. This is after you've drunk the wine, obviously. You know, once it's in the bottle, it's kind of hard to get out. So it turns out if you take a plastic bag and you put it in the model and you sort of get it around the cork, you hook it around the cork and you pull a little bit, and then if you blow a little bit of air into that plastic bag and you yank, the cork comes out. So you can try that. So there was a guy named Adon, he is a car mechanic in Argentina, and so he was wasting time one afternoon watching YouTube videos with his friends in his shop, and he watched this video and watched a couple of times and thought, well, this is really interesting. And I cannot tell you why this is where his mind went, but his mind went after seeing that video to thinking that technique would be great for getting a baby out if there's obstructed labor. So now in trials, we have something known as the Adon device, which he came up with the idea from the YouTube trick. And so basically, the way it works is kind of like a little plunger and you put it on the baby's head and then you push the plastic bag over the baby's head. There's still an umbilical cord, so it's okay that there's a plastic bag over the baby, and then you yank, and that's how you get a baby out. And so it turns out in large parts of the world, women give birth at home, and if there are complications, the odds are that either you or your baby is going to die. So because the time it takes to get someone to a health facility where hemorrhage can be stopped is the odds aren't good. So this device is great. It's incredibly low cost. It's so low cost that it can be given out with the safe birthing kits that midwives usually give to mothers when they come in for anti-natal visits. So came out of a YouTube video, justification for wasting time watching YouTube for all of us. The next example I want to talk about is from, this is the ultrasound project that I mentioned that some of my students have worked on. So this is a commercial portable ultrasound machine. And so there's some sliders on the left, and then there's a scroll wheel down there, and then there's some soft buttons up top. There's a keyboard and also a track ball, and then there's some extra buttons on the side. I don't know what those do. And then you can see some labels over there, some little yellow stickies that hospital staff added to remind themselves what those buttons do. And then sometimes if you go in and you look at an ultrasound machine, you'll see that sonographers have put tape over some of the buttons to remind themselves not to use it. So I teach in a department called Human Center Design and Engineering, and the human that uses this has a better brain than I do. So it's very complicated. So what happened was a colleague of mine in radiology came to me, and he was starting a project working with midwives in Uganda, training them in basic ultrasound to diagnose some pregnancy complications and finding at-risk mothers and referring them to give birth at a health facility so that they wouldn't have to use an oddone device, for example. And he said, you know, I don't know about the situation in Germany, but in the U.S., if you want to be a sonographer, you train for two years. Well, they didn't have the resources to do that, so they wanted to bring the midwives in and train them for two weeks, maybe four weeks. And so the idea was, well, how can you come up with a less expensive, not just a less expensive, but a simpler to use machine so that two weeks of training might actually, you know, you could actually figure out what you want to, what you need to do. So this is, I had no money, right? So I said, well, we'll just, we'll ask my undergraduate students what they can do because they're fearless. And so they, not knowing the domain of the problem space at all, came up with a completely different solution. And so they took an off-the-shelf probe that was available from a company called Interson. It's older technology. It's not as good as what you'll find in a Philips machine, but it's good enough to diagnose those conditions. And they paired it just with an off-the-shelf netbook. And then they made a really simple to use user interface. And, you know, I don't have a picture in this deck, but I was in Kenya last week, and we showed it to some nurses who had never been trained in ultrasound. And it was amazing. So I was traveling with a male colleague, and we made him lay down so they could scan him. And within about, I don't know, two minutes or so, they were identifying things inside of him. And then someone said, go get a pregnant woman. Go get a pregnant woman. So they went outside and dragged in a pregnant woman and started scanning her. And they had no training in ultrasound whatsoever. So, so my students, you know, they, they worked really hard and they came up with this. And then, and then they did this crazy thing. So they actually talked to the midwives out in the field who would be using a device like this to find out what they needed. Did a bunch of tests. They also looked at that general context of care. Because, again, they didn't know the domains of the problem space. They were complete non-experts at this. And then they got really crazy and they actually talked to mothers. And they said, asked them about their preconceptions about ultrasound and any concerns that they may have, thinking about how the design of the system might address that. And they had them do all kinds of design activities to figure out the ecology of care decisions. And so the very simple user interface is one of the things that they came up with. The other component that they developed was a help system. So in a traditional ultrasound machine, a commercial machine, if you click on help, you'll get something that's a little bit akin to an old Windows help. So it'll give you some sort of useless technical information about the system. And so after having done this work and also paying attention to the way radiology and imaging works in a more resource-rich hospital, and getting an understanding that when doctors order imaging, it's a collaborative process from the person who captures the image and the doctor who interprets it. Contrasting that then with the way the midwives in Uganda were working, where they were working in rural environments, they were usually the only midwife on staff because there would be two, but they would work 12-hour shifts, so they would switch off. There's no internet and there is some spotty cell connectivity, so there was sort of no access to resources. So they thought, well, why don't we also turn the ultrasound machine into a learning device? Because they didn't know that you weren't supposed to do that. So they created this robust help system that has a lot of information in it. So you can sort of read about certain conditions. There's a button there, step by step. You can get instructions on how to capture certain kinds of images. You can also listen if you don't want to do all the reading. You can listen to the information there, and there's an image library. So you can compare. This is what you're capturing. This is what you're looking for until you get the right kind of image. And you can see the sliders there on the right. Those sliders, they replace those together with the keyboard of the laptop, replace all of the buttons on that first machine that I showed you with all those arrows pointing to things. So in terms of these communities, thinking about the hackers in Uzbekistan or the hacker in Argentina or my students in Seattle, they're all doing research, okay, and they're doing engineering, and it looks different because they have different constraints. And the different constraints are what allow them to be disruptive, to come up with technology that really is a game changer. So there are, you know, there are multiple research communities that produce innovations. University and industry labs do a lot of really great things. I'm not saying that they don't. And then there's the relationship, you know, between or among universities, industry labs and independent researchers, and that, well, that relationship, it might look like that, but it might also look like that. So it can also look like that. Actually, I don't really care what it looks like. What I care about is that the independent researchers are sort of out there, and they have a different set of constraints. And they don't know better when they're not experts. And that means they can do things better in a lot of ways. And they can come up with more original and more disruptive designs. There's lots of reasons why this kind of work is best done independently, because it is disruptive. And as sort of we went through earlier with that Christensen model, the disruptive work, it doesn't fit well in a lot of institutions. There are those real structural disincentives to coming up with disruptive designs. So that's sort of a bunch of the stuff that's going into that book that I'm writing about disruptive technology and hackers. But then the second piece of that is trying to foster more open innovation. And so that's where this project Hackademia comes in, which is predicated on openness. So open software, open hardware, as well as open communities. So basically, I want to create the conditions for more of that rule breaking and more disruptive innovations. So there's a bunch of things that I've been doing along those lines. So I've been looking at different kinds of open resources in communities. So things like contests and peer based and crowdsourced reputation systems that you see in the maker, as well as hacker worlds, taking an educational focus on looking at what some of the workshops and contests that happen within like a conference like DEF CON, for example. But also looking at some of the emerging educational examples like Khan Academy and Code Academy, Stanford University's online courses, MIT's open course where in looking at the way that technology is fostering the ability of those non-expert communities to work on their own knowledge. So I've been looking at a combination of online and offline resources, so hacker spaces and maker spaces, I mentioned, cons and also maker fairs. And then also doing a lot of interviews with individual hackers and makers. So that's again all extracting those patterns and sort of focusing in on some of the characteristics that seem to be really important for success. So community spaces, for example, and apprenticeship models, also reputation building events, again looking at characteristics and commonalities. And so my goal is not replication, but adaptation. So I, as I mentioned, I've spent many years in my local hacker community and there's no part of me that would say this can be replicated wholesale and brought into institutions and used productively. But what I'm trying to do is identify those characteristics and figure out how to adapt them to different settings. And ultimately the reason why is because I think that more rule breakers will make the world a better place. And so that photo actually is, you go back to sort of that very first picture that I showed with the snow, one of the first projects that I did with that hacker community was a balloon launch, and so that's a picture from our successful balloon that went really high up. So this thing that I'm running, this academia, my role or my goal is to create pathways to innovations by creating pathways for people to gain functional engineering skills. I don't care whether they're accredited. I don't want to turn everyone into an engineering major. And this sort of semi-formal learning environment, we collaborate with our local hackers and makers. And I'm really, really interested in how non-technical adults acquire their technical skills. So if you haven't already been tracked into that. So this isn't just in the university, but it's also thinking about the community outside and getting away from the limiting problem of self-selection. So casting a broader net, trying to draw in people who wouldn't find themselves in a hacker space under normal conditions, but who still have something to contribute. You do need to give people basic skills. You need to have some knowledge so that you can have that different perspective and potentially innovate. A shared vocabulary is really important. So for me, I see academia as about creating potential. The students may never do anything as long as I know them, but hopefully five years down the road, they'll have been positioned to be potentially awesome innovators and make some great contributions. We have a bunch of specific educational methods and approaches, which I'm not going to go into here. But basically the key is how do you provide enough foundational knowledge so that people can read or tinker or experiment their way to functional engineering expertise. And so you're going to hear in just a couple minutes about the open innovation challenges. And so I, you know, I'm sorry, I would say is think about something that you're not necessarily an expert in, but figure out how to have conversation with those who are experts in the domain that's necessary to execute well in those challenges. So that's my lab, you know, to be an expert, to be an innovator. And so I had mentioned at the beginning of the talk that there were three things. There's the book and then this academia project and then a third. And so indeed, no one knows what tomorrow brings. And so the book isn't done. And honestly, I'm not sure when it will be done. Because what happened was I got sort of halfway through it and I thought, well, writing about innovation is really great, but I'd really rather just do it. So I started a company. So I started a company with a bunch of hackers. It's an engineering and manufacturing company. And what we're doing is we're building low-cost health technologies for low resource regions. And that vice president that I told you about about 10 minutes ago who said, oh, no, we could build cheaper technology, but it wouldn't support the cost of our sales force. He was my inspiration. Because I do think that model is broken. So we really want to figure out how to make low-cost technologies and sell them everywhere, bring down the cost of healthcare. And one of our primary kind of ethos is working with hackers rather than traditionally trained engineers because we want creative solutions to those entrenched problems. I will say that one of my co-founder does have a PhD in EE and bioengineering. But I didn't know that. I met her through the hacker community, so I still consider her a hacker. And everything we do is predicated on open hardware. So it's based on all the openness that we've talked about here today and the fact that with open hardware, you don't need specialized EE knowledge to build things. It's amazing what you can do with technology remakes. And so we're trying to put that into work. And we're doing a round. So if you're interested, you can come talk to me. And I have lots of acknowledgments there because that's part of what we do. Lots of people have helped over the years. There's acknowledgments to all of them. And thanks to all of you for your attention.
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The re:innovate track highlights different perspectives on Open Innovation. This session presents a civil society and scientific view. How and why do nonexperts contribute to innovation? Beth Kolko will provide an insight into her work with hackers and makers to demonstrate the contributions of non-experts and the ways institutional structures generally forestall these kinds of contributions and how organizational boundaries exclude them from conversations that can lead to innovation. Her conclusions are based on over a decade of fieldwork in developing countries, and inadvertently seeing patterns of innovation among populations with little access to formal education, professional-grade tools, or any formal experts. Beth also teached and watched non technical students which solved old problems in new ways because they didn't know enough to understand the boundaries of the domain space. None the less academic or industry labs are highly unlikely to ever recognize them as 'experts'. As a result of this work she started writing a book about hackers and makers and non-expert-innovation with focus on the notion of disruptive technologies.
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10.5446/21386 (DOI)
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Hi. So I go to a lot of these conferences and oftentimes I'm sitting out there with you all and often people talk about all of the big ideas, but it's rare that we actually get to hear all of the back story behind these internet movements that happen. So that's my goal for today, is to tell you about the details and some of the smaller sized insights that have happened over the course of this project that I've been running for the last several years. So the title of the talk is getting broken and forked for the planet. So first of all, I want to start out with one very simple fact, which is that most people, when we talk about the environment and environmental impacts, we have no idea what we're talking about. We are all kind of making grand claims or doing a lot of speculation, but we don't necessarily, most people don't actually understand what the ramifications of any given action they take regarding the environment, what those are. And there are actually only a few people on earth who are really qualified to make broad statements about environmental impact. So for example, one of those people is a scientist named Wally Broker, and he's an 80-year-old man who has been obsessed with climate change since probably the 1950s. And he's been peer reviewing articles written by other scientists for a very long time. And so when a journalist wants to know whether or not the catastrophe in New Orleans was related to climate change, Wally is one of the very few people who they can call who could really venture a guess along those lines. But for the rest of us, it's really hard to understand all of the complexities of how we're doing impacts something as complex as the environment, as the ecosystems that were surrounded by. So basically the takeaway of that is that you don't have to be a specialist or an environmental researcher of any particular kind in order to make an impact, because you're basically just as qualified as most other people on earth are to make an impact on the environment. I am pretty much one of the most unlikely people to have done this. I grew up on a ranch in Texas, just kind of a country girl. And I moved to the big city because I wanted to deal with technology. So I'm like all of you guys, I'm really interested in technology and have been for years. And unfortunately, I couldn't really do a whole lot in Brenham, Texas to shape the way that technology was going to impact our lives in the future. So after having moved to the New York City and having worked in the technology field for quite a while and having noticed several ways that I could make incremental changes using technology to impact the environment, I ran into the work of Michael Pollan. Now he, I don't know about here in Germany, but in the States he is almost a household name at this point. He wrote a book called the Omnivore's Dilemma, which really was one of the catalysts in the food movement in the United States. So in the local food, knowing where your food comes from, the sustainable farm to table movement, he was basically the author of it. And one article that he wrote for the New York Times, in this article he made the point that actually the food movement is not just about being a responsible consumer and buying this produce that someone else has grown responsibly, it's also about actually getting your hands dirty and growing some of it yourself. So he brought the whole DIY aspect of things into the food movement and he really reminded me of that, what it had been like to grow some of my own food and learn from these little ladies who grew everything that they ate when I was growing up in Texas. The problem was that I lived in a New York City apartment on a fifth floor walk up with no balcony or no room to use any of the traditional techniques for growing that I was familiar with and that Michael Pollan was talking about. I did not have a California backyard. So I started to look at, but he had really gotten to me. I was really, I really wanted to participate in growing some of my own food. So I started to look at my opportunities within my apartment from the standpoint of a plant. And the one resource that I really had to offer was my window and the year round climate control that I already had indoors. So I had this vision. What if I could take hydroponics, this technology that NASA has been using to experiment with growing food in space, that pot growers around the world have been using to grow their cash crops very reliably. What if I could actually implement that in my apartment so that at least some portion of my own food would be there growing constantly in front of my eyes. The thing was that just doing that for myself, you know, it would be cool, but it would be just kind of my own personal project. And I started to think about the fact that there are actually probably about three billion other people like me on planet Earth who live in these little boxes and all they have is a window to offer plants indoors. So as soon as I started looking at this, not just from the standpoint of what it was going to do for myself and my being able to show my cool hydroponics garden to my friends, but what if I could actually scale this up from the beginning. So if it were not just my window that were filled with growing greens, but windows all over the place. I want to take a step back for a little bit now from this moment and talk about my tech background. I had the privilege of going to New York University, the interactive telecommunications program, and I got to study under one of the luminaries in our field, Clay Scherke. He wrote a book called Here Comes Everyone, and then another one recently called Cognitive Surplus. And one of his areas of real interest was open source, first of all, and secondly, crowdsourcing. So back in about 2005, 2006, I was studying under him during the time that Wikipedia was really starting to blow up. There were a lot of entries being created there. There was also Amazon's mechanical Turk coming online and all other kinds of crowdsourcing projects. But at that point, sitting in his class, I was really frustrated that a lot of the crowdsourcing projects were really reducing human beings to little more than fancy robots, essentially. We were doing very simplistic tasks. And I was really excited about Wikipedia because what was happening there was really much more of a collaboration. There was a back and forth between individuals that was building to something much bigger. And that really inspired me. And I started thinking, this mass collaboration thing, we really need to take that farther. We need to figure out how to have lots of people be able to interact with one another and build upon one another's work. The second big moment that I had shortly thereafter was I decided to take on some environmental art projects. And one of them, I started hacking some technology that some scientists had been developing for sewer treatment. So their idea was that they were going to take all of the urine that was coming out of all of our toilets and they were going to divert it out of the normal sewage treatment stream and they were going to put it into its own stream so that it could be treated. And it was going to be a very huge infrastructure project and in fact it's been undertaken in Switzerland. But I decided that I wanted to hack that for the individual level. So a friend of mine and I, we set up our own little chemistry lab in my apartment. And we started taking this large scale technology and we just boiled it down to something that could be done at the individual scale. So it was a little kit that let you turn your own urine into fertilizer. And it was a crazy kind of funny environmental art project. We did it in a whole bunch of places and at the Ars Electronica Festival and people really loved it. And the really important thing that I got out of that project was that first of all, people were really excited about the opportunity to do something themselves. And they would come back to me after having turned some of their pee into fertilizer that they were going to then use on their house plants and say, hey, you know, I've got another idea about how you should apply this. You should really, you know, put this into a composting toilet of some kind. And I would look back at them and I would say, like, this is not my thing. Why don't you take it? Why don't you put it in the composting toilet? Why don't you take it to the next level? And there was just something that went off when people thought, oh, wait, I can do this? And it was seeing that little burst of interest that made me realize that we all often think like consumers. We think that somebody else needs to do this for us. And it's just because we've been living in a civilized world for a very long time that we have largely forgotten our own power to just go ahead and hack things. What I learned through the process of doing this urine to fertilizer transformation project was that using the Internet, I could look up all of these research articles by scientists, 90% of which I didn't understand, but I understood just enough to give me a little thread of something to work with. And then secondly, for anything that was beyond my personal capacity, I could look in my social network and within about two to three degrees of separation, I could usually find a link to someone who was an expert in a given field. And so that was how I was able to work through some pretty advanced chemistry in my own kitchen. What if we continue to do that? If not only I did that, but if lots of people did that, we could work through some really challenging projects. So that's when I came up with the idea for something that I call RNDIY. So applying mass collaboration to solve environmental problems, but doing it as ordinary citizens. We're the ones who know what it is that we need for our particular situations. And we have resources that we can mobilize to get something accomplished that we don't feel specialized enough to do. I thought that I needed something to start this project off that was going to be very tangible and very easy for most people to do, as well as something that people were excited about. Unfortunately, turning your pee into fertilizer is not the most appealing thing for a lot of people, but growing some of your own food is. So my first case study for research and development yourself was going to be window farms. And that is when I launched this video on YouTube. I'm Brita Riley and this is where I live, Brooklyn, New York. Lots of cement, lots of people, lots of snow, not a lot of farms. This is what I like to eat, fresh food, mostly vegetables. And this is where I get a lot of my food. I have no idea where most of it comes from, but I do know where some of my food comes from. In fact, it comes from a window in my apartment. This is my window farm. It's a vertical hydroponic garden made out of water bottles, tubing, an air pump, and some hydroponic supplies. Most of the stuff I got out of the recycling bin at my apartment building and at my local hardware store. Not only do I know where this food came from, I know exactly what nutrients fed the plants that I'm eating. And I grew the plants up from seed myself. The window farm works because an air pump generates a little bubble at the bottom of a tube submerged in the nutrient-rich water. The bubble carries a column of water on top of it, and it rises up through the tube and spurts out the top. Then the water trickles back down through all of these bottles. I'm no longer the only window farmer. In fact, in the six months since I launched the Window Farms Project with some friends here in New York, people are building window farms and growing their own food in the heart of cities all around the world. They've been downloading instructions that are available for free on WindowFarms.org. After they build their systems, they join in a mass collaboration online. Together we all identify issues with the window farm systems, propose solutions, and test techniques for how to best grow different kinds of plants. Whereas NASA is researching how to grow vegetables on the space station, we're researching how to grow food in the unlikely conditions of city windows. I call this process of ordinary people contributing small innovations to collectively solve environmental problems, R&D-IY, or research and develop it yourself. Through the insights of window farmers, the designs keep evolving. Look at my first system. Wow, it was pretty janky. But it kind of worked. And the in-hue improves stability and performance by screwing the bottles together and testing new pumps. Jackson suggested using the more efficient air pump technique. Ian solved the noise problem by making something like a gun silencer out of a vitamin bottle. Nico added LED grow lights. And teams in Italy, Finland, Hong Kong, and Spain are translating the designs for their local materials and languages. With each improvement, it's easier for the next person who joins to build a window farm. So now we have a multidisciplinary team of hackers, foodies, teachers, gardeners, all around the world collaborating online to solve one of the biggest problems facing our environment, how to supply fresh local food to people in cities. Thanks. Yeah, so hundreds of thousands of people around the world have now watched that video. And over the course that was in 2009 that I launched that video. And we now have 33,000 people around the world on this website. So it has been a really crazy experience. And this is a little bit of the behind the scenes view of what happened because I had no idea when I launched that what was going to happen, essentially. But so basically, window farms has taken over my life for the last three years. So that was 2009. It's now 2012. And definitely all the way through 2013. I'm going to be very deeply embedded in this. So what happened along the way was that, first of all, I was like, oh, my God, what do I do with all of these people? And all of a sudden, something that had gotten to be just kind of like a crazy idea became a full-time job, not just for one person, but for several people. And so basically, I had to figure out ways of making that work and be sustainable because it's just such a beautiful thing that I've wanted it to live. But I've had to figure out how to make it work. And that's what I'm going to talk about. So the first thing is you've got to be willing to put stuff out there that's broken, and you've got to let people talk about it. There's something really fascinating about watching someone else struggle a little bit when it comes down to us humans. We're very, very strange creatures. But we like to watch people be working through something. And I think that's part of what has gotten so many people involved in this. You also, there's the term in software, we talk about fail early, fail often. Same thing applies here. You've got to be willing to put pictures up of something that is not perfect and doesn't work. And that will actually be the much more visited image. Yeah, these are some more of the pictures of my very janky beginnings. And this is an image from one of the times when I lost my entire crop because one of my pumps went badly. And that's when I made a very major decision about what strategy we were going to use regarding pumps at that point in time. But when you do fail, you want to always learn from that. One of the things that I hear people talk about very often is they say, I can't do this because I don't have a green thumb. Is that a common expression in German too? Do you have some equivalent like that? Yeah. But getting a green thumb, it's not something that you're born with. It's something that's developed by killing plants and then figuring out why you killed them. What was it that went wrong? And then furthermore, if you're going to be doing that through a collaboration, you want to publish that failure and let everyone know what your hypothesis was for what went wrong so that they can then avoid that same problem in the future. And when you do this, other people follow you. They also publish their failures and help troubleshoot what went wrong with that particular plant. They're willing to put their pictures up of their duct tape together at window farms. And they will put together really crazy contraptions that kind of work and kind of don't as well. And that's how you find your people. That's how you build community. Without this process, those people help eliminate parts that we see don't work universally for everyone because everyone's trying out a very similar design. And they say, you know, I'm still having that same problem that you're having and someone introduces a new solution. And so that's how we can move very quickly through designs. Another lesson that I learned a long time ago before I started this project was when I was doing a specification for a massive website for this organization called the Smithsonian in the U.S. And what they do is they basically own all of the best stuff, the national kind of archives essentially in the United States, as well as they do a lot of scientific research. And their mission is to publish this and put it out there for the U.S. public. And one of my projects was to get them into Web 2.0 and to make it so that they could actually use, publish what they were developing. And throughout the course of that project, what I had to do was evaluate a whole bunch of different open source software platforms for web publishing and to determine which one the Smithsonian should go with. And through that process, I got to understand one of the most fundamental things about running an open source or a mass collaboration project, which is that you must keep the community's health and well-being for the long term in mind. And so I brought that to R&D, IY, and I was very conscious about creating a culture. So first of all, I wanted everyone to know what our mission was. And our mission was to navigate between the needs of people who are going to be living with the plants, the planet, so the environmental impact that we're having while we're doing this, and the needs of the plants. These things have to be technically functional and run well to serve the plants. So there were a few tenets that I continually put out there into the community until the community internalized it and began self-policing. So first of all, don't just put out ideas. You need to actually be willing to try them. Secondly, be a tester. Being the idea guy is not the coolest thing in our community. The way cooler thing is to take an existing idea and actually be the one who implements it and finds out all of those really interesting nitty-gritty details that emerge once you actually put something into action. Be a proposer. So if you run into a problem or you're skeptical about something working that someone else has proposed, come back with a counter proposal. And also acknowledge that your particular design criteria and needs are not necessarily going to be shared by everyone. Someone else might have their own needs. Secondly, just really reminding people that they are authorized to make the decisions. So giving the community a lot of power as far as decision-making is concerned. And then finally, this has been really the very challenging part because managing a mass collaboration does require some very... It requires a lot of back-end technological solutions, which I have not had a lot of access to on my budget. So creating some sort of platform where people can share their ideas. And along those lines, one of the needs that emerged is we started running into the US patent system. And one of the areas that's really occurred for me as being the place that we need to be working and that we're starting to work now is to make all of the designs that we share with one another follow the guidelines of the international patent and trademark offices so that as people come up with new innovations, they can actually be acknowledged as prior art by these organizations because generally the way that people publish their designs online is not recognizable by the USPTO. It's not... The line weights are not precisely the way that they should be or the language has not been written in that way. So that's one of the things that we're building into our community going forward is having people build something so that it can be acknowledged as an open source contribution to public intellectual property. And then you get to sit back and enjoy watching the most beautiful experiences that happen as people around the globe get to collaborate with one another and pass back ideas back and forth. The next idea is getting forked. So that's a very common term in open source software. So if you look at the course of history, everyone who has invented something has always stood on the back of another technology that came before it and that's what we're continuing to do. But the question comes in, who gets to decide when something is a viable course for the community? So I try and leave it very open. So Brian White here, he introduced a design that didn't really... It doesn't really work with window farms, but he's kind of really just interested in pumping technology for application in various other areas. And I let him just decide and throw that out there and he started a contest online. Somebody else decided that they wanted to make window farms wearable. And now I would not consider that a very universal design, design concern, but why not? So over the course of time, there's been this wonderful tension that happens between what I would call the core concerns, so the concerns that are shared by the most people represented here in green and the yellow concerns, which are either... They may be specific to a particular community or a particular set of constraints, or they might just be an interest that was once there for some people and it was solved by a new innovation, but we can let all of those plethora of designs coexist. So again, the green area there is naturally there's an attraction. More of the traffic ends up going to the areas where someone else says, oh yeah, I've got that problem too. That's why I like this particular design. So I, as the kind of administrator, I get to watch those traffic patterns and learn from them. But I'm also the one who's concerned with the mission of the project. So again, people will sometimes get very focused on their own particular concerns or they'll be designing for some particular reason, but the other thing that I'm really looking for is the intersection of all of our three mission areas. So the last area is dealing with the financial sustainability of this mission over time. And this has been one of the things when something that you really love takes off, you really want to find a way to make sure that it can continue over time. So this was basically the arc of it for me. Very early on it started getting a lot of traction and I realized, oh my God, this costs a lot of money. And I put a donation bar up on the website and over the course of two years, I think 50 US dollars was donated. And I was like, what is going on, people? But really there was, you know, there's a relationship that we have with the internet where we're used to getting things for free and we don't really think about how much work goes into it on the back end. So I realized that, you know what, the donation model is just not going to work. So the first way I funded it was with Kickstarter. But I didn't do a Kickstarter just to get money for the project. It was to create DIY kits to save people the trouble of having to gather all of the materials. One of the big revelations there, though, as I started to unfold that DIY kit business, is that repurposing water bottles actually has pretty large environmental impacts. And at the same time as I was kind of scaling it up, I was noticing that we had a bunch of people coming to the community who were not DIYers. They didn't actually want to make it themselves. So it got to the point where the community itself was leading me in a new direction. We needed to start looking out again for the planet, for the environmental impacts, and for the plants, essentially. So to that point, most of our DIYers had been much more focused on building the systems and had not been paying quite as much attention to the plants. So that's when we went to a fully designed and engineered product that I got to write the specifications for based on what I'd learned from the community over the last three years. And at that point, I was able to focus the community much more around the experience of the plants and the sharing of knowledge about the plants. So what we're working towards now is what we call the Window Farmers Almanac. And Almanac is a body of knowledge that's put together by a bunch of farmers based on what kind of experience they've had with plants in different kinds of microclimates. So we're trying to make that digital around this digital community of people around the world. So as Brenda asks, how long can I harvest my arugula? And Macy answers that question. We can have their knowledge as well as all of the knowledge of other people growing arugula be aggregated together. And then that can be there to supply information to new people coming on board who want to know what they can grow in their particular Windows microclimate and they can find a suitable pairing of plants. So the way that I've been able to make all of these new parts of the project unfold has been to create revenue streams on one side to also continue to fund the social mission. And there are some new organizational forms that are available in the States and I'm not sure what they look like here, but we're actually incorporating as a social enterprise. Hi, I'm Brenda. I run the Window Farms Project here in Brooklyn, New York. Window Farms are vertical hydroponic gardens that let you grow some of your own food indoors even during the winter. There's a pump on a timer that sends liquid nutrient solution directly to your plants root systems so you get great nutrition in small spaces. Until now, Window Farms have been made out of water bottles using our open source website. But the water bottle versions take a lot of time to put together and not everybody who wants a Window Farm is MacGyver. So with your help, this is what the new Window Farms are going to look like. I asked a couple of top industrial designers and engineers to help us make beautiful new Window Farms that just snap together and make it so easy to care for your plants. You can keep it simple by growing salad greens and herbs or you can go big with things like strawberries, cherry tomatoes and peppers. You don't have to have a green thumb. There are 22,000 of us Window Farmers online and we are committed to making sure that we all know how to grow. I want more of you to come join us in knowing where at least some of our own food comes from and being able to grow produce at home that's fresh, crisp, bursting with flavor and pretty much as local as it gets. I want more of you to have the joy of nature at eye level and to be able to share that with your friends and your families. Okay so here's the deal. In order to get the new Window Farms produced, you need 500 of new Window Farmers to come on board right now, all at once. With 500 pre-orders, we can afford to get the molds made and we can meet the minimum production quantities. But if we can get 2,000 of you guys to come on board right now, we can afford to get the new Window Farms produced here in the States. So if you ever wanted a Window Farm or your mom wanted one or your kids teacher wanted one or your boyfriend wanted one, now is the time. The way Kickstarter works, we either hit the minimum and we all get Window Farms or none of us do. So how about this, why don't you be the first person on your block to get a Window Farm and then tell your neighbors about it so that 6 months from now you guys can be swapping tips about your strawberries and your cherry tomatoes and your arugula and we'll all be learning together how to grow again. And at that point when everyone's doing it, you and I and anyone who comes to our website is going to know that you were one of the ones who helped make it all happen. So that was a video that I put on Kickstarter the next time when I went to launch this. And we were successful. We brought in $257,000 in pre-sales and we were able to get the Window Farms manufactured in the United States which is a huge victory for our kind of failing manufacturing. Thank you. Hi, I'm Britta. I run the Window Farms. Wrong way. So the final lesson that I just want to talk about is trust. This video, what you probably don't know is that it took me 319 takes to get that video because you can imagine what it's like when you've been running this project for such a long time, you're totally out of money, you're so excited about making it happen, but it seems so far away. It just seems like there's no way anyone is ever going to do this. They're going to think you're crazy and so when you're talking to a camera that's right there in front of you and you're trying to convince people, it's really hard to get out of your own head. And it took me 319 takes to get to that point where I believe that all of you guys were in this with me as much as I was. And that is really the key to making the environmental movement work is that you have to trust that other people are in it with you. So I'm going to go back to the beginning. No one knows what they're talking about with the environment. No one is a specialist. And you don't need any kind of specialty degree in order to be able to make a difference. And so therefore I hereby anoint you all environmental pioneers. Thank you. Do I have time for questions? Yeah, yeah. Not only did you give a most amazing talk, I think anybody who can stand on the stage talk for P, talk about P for 10 minutes and get away with it, has a mon already, but you also landed on point. So we have 20 minutes left for questions. So please don't be shy and use this opportunity to find out the details about how you can install this window farm in your window. And please let's see some raised hands. Do you have a mic? Mic's coming. Hi, last time I checked on the website, the kid was not available outside of the United States. I'm working on it. I'm working on it. That's one of the reasons why I'm here. Yeah. Okay, over here please. Hi, I'm Phil from a Volcato store. I'm running Germany's biggest online marketplace for sustainable products and we would like to have your product. Cool. Great, we'll talk afterwards. This is good. At this rate you can all ask questions. Two questions. First of all, have you ever any connections to the vertical gardens movement in Holland for outside walls? I'm sorry, say it one more time. In the Netherlands there's a movement going on for growing vertical gardens in the outside walls of buildings. Do you have any connections to that? You know, there are a lot of movements going on in the gardening world right now. Thank God we are having finally a revolution for those of us who have grown very distant from agriculture which is very fundamental to human society. So I am so glad that there are so many different kinds of that growing on. I am particularly focused on just growing inside of apartments. Okay. Yeah. I only thought this could be a great combination. The second question, when you talk about the Almanac for the gardeners, do you have already a publishing infrastructure for that? Yes. We are launching the alpha version of it. Actually we already launched it last week to a small community and we are growing it so we are rolling that out right now. But yeah, it's going to be under development for many phases. As a web platform I suppose. Yes. More questions. Okay. I will go. So you said you are working on bringing them to Europe? You got me already. I really want one. Okay, cool. I grow like herds on my balcony but I live on a big street so I always fear they are polluted. I am much rather grossed off inside. How do I do it? What would be my concrete next step? So you should come back to our website in September or October. So actually they are being manufactured right now and they won't ship even to the people who ordered them on Kickstarter. That's another thing that I would like to say for any of you all who are considering doing Kickstarter based manufacturing projects, you are probably going to be late. We were late and I think everyone who has done a manufacturing project on Kickstarter has been late. That's one of the kind of things about that platform is it's really difficult to get everything up and running within that short time frame. But in any case, they will ship in the United States and to a few people who ordered them on Kickstarter in Europe in August. But then we are hoping to roll some out for specifically, I think we are going to start with Germany because you guys apparently really like window farms. So September, yeah. Excellent. Okay, we will be watching out for that. Are there any more questions? The lady in the red please, Anya. Way in the back? No, in the middle of the lady with the red and then afterwards those two waving hands in the back. Hi, I'm Anya. You probably get that question a lot, but I just wonder how many days of a month or a week or the year can your community members live on their window farms? Is there any, do you have any information on that? Yeah, this is a really excellent question. So first of all, you're not going to live on your window farm. No one is. It really takes like many, many hectares of land to generate enough food to feed a single human being. And we're kind of not really aware of that anymore, I don't think, because we can go to the grocery store and we see a lot of produce there together. But so again, it's a little bit about what Michael Pollan was talking about, of reconnecting with food in a way so that it's much more of a learning experience and more of kind of a way of satisfying that biofilia, the yearning to be around nature that we experience as people who live in cities. And it actually can make a pretty good dent on the financial side if you choose to grow the types of plants that are very high turnover. So for example, I use a lot of basil and a lot of kale and things like that. And you can grow what are called cut and come again greens where you can continue to harvest from the same plant over a longer period of time. So I basically, the way that I think about it is that I can get about a side salad a day out of mine, but I have a very big window farm. Yeah. Okay. Hi. It's very inspirational. I'm just curious what happened to the original DIY pioneers when you changed directions, as you said, to kind of save the mission. So there's a tension between the people who want to do things themselves and the people who want to make a change, but need an easier way. So how do the two, will the Almanac solve your problem or linking the two? Yeah, they can both live together in harmony. I mean, there is nothing, nothing has happened. The community, the DIY community is growing like wildfire and we now have people on there who have been doing it for three years and are absolute experts at this point, just as much as I am. So they, it's continuing to thrive and I'm really trying to continue to build tools to give that community the best possible infrastructure. But it's pretty well taken care of at this point, I hope. We have one more question up here, please. Hi. I also like to talk very much, but I would like to know more about the fertilizers. Now, one of the key reasons to actually build such a garden, what was such a device to actually grow plants would be, of course, to use only organic stuff to fertilize the plants. Now is that possible in a setting like that? That is exactly what we are most, you know, one of the biggest concerns on the plant side. So hydroponics traditionally use inorganic nutrients. There's nothing really wrong with that. It just does not supply as diverse nutrition to the plants. So you're not eating as diverse nutrition. And the environmental impacts for inorganic growing in hydroponics are much less than they are when you're dumping a whole bunch of nitrogen and phosphorus out on fields and then that's running off out into the sea. But I specifically designed the new window farms, building on the design advantages that we did with the DIY kits so that they can make the best possible use of organic hydroponic nutrients. The traditional problem with organic hydroponic nutrients is that they're very unstable. And so they precipitate down into a kind of sludge at the bottom so it's no longer available in the water. But we designed them to have a curved bottom with the suction intake right there at the bottom so it works to constantly continue to have those organic nutrients be circulating through the plants. We also have, there are so many amazing resources for giving nutrition with hydroponics that we have not, we've forgotten about as a culture. That were very, they were under research in like the 60s and 70s a lot. But I know in California. But using nutrients from the sea, essentially from the sea floor, you know it's just the same as it was on land before we over grazed all of these crops. And it's available there in the oceans. And we could actually make really good use of those nutrients for excellent nutrition for human beings and cities. Thank you. More questions. Okay. Last calls for more questions for Brita. There. Okay. The gentleman with the, no, did you not ask, sorry. Oh, look, there's somebody who moved. You can ask another one because we've got some time left. So please, if you have some, keep them coming. So I got one other question about efficiency. Now, I mean, you have to ship all the stuff like the fertilizers and the kid and whatever. And isn't it a lot less efficient? So it's more the educational part that's valuable there. Because if you build like a large scale farm or even a media sized farm, then it's still very efficient if you bring out the fertilizers and stuff you actually need to get the plants growing. Yes. So it's a more model where you have to put in everything yourself. Wouldn't it? Yeah. So basically what I, the way that I like to talk about this is in terms of us having a hypothesis that we're testing. So it's not a good comparison to just directly compare what we're doing to a farm, for example, because if you live in a city, how are you going to get the food from the farm? Right? But what we've been looking at are, we're still actually looking for good statistics that we can use as a comparison for agriculture of the kind that we're dealing with. But one statistic is that it takes 10 calories of fuel to get those of us who live in cities, the food that we eat in the grocery store, so our fresh produce. And if that is true, then we are definitely below that amount of carbon that we're using. Because when you think about it, I grew up on a farm and we used fuel-based, petroleum-based fertilizers. We used fuel to drive the tractors. We then had to use refrigerated trucks to basically transport the material. Then it has to be refrigerated at the store. And so once you take into account all of those things, there's the plastic packaging that everything is wrapped in. Once you think about that, it's actually a huge amount of energy that goes into getting us food in cities. So that little amount that you're growing using an air pump that only turns on once an hour for a few minutes, that is actually in all likelihood a much smaller carbon footprint. But we're still testing that and trying to find good numbers. Okay, if there are no other arms rising up right now, then I think... There's one more. Okay, we'll have the last question then, please. Thank you. I was wondering, you were talking about the impact of recycling bottles to use them to grow the plants. But if you're producing the kits now, doesn't that disappear? Or what kind of material are you using for the kits? Yeah, so basically what I was comparing it to is that we're going to have a lower carbon footprint, making something specifically for this purpose and controlling all of those variables and inputs that went into it as opposed to my going to the local hardware store and buying all of these little components that have mostly been made in China for the most part and then were shipped all the way to me in New York City. And then I'm paying retail prices for all of them. Plus, I'm customizing them in ways that make them no longer really recyclable or things like that. So once you take into account all of those little granular impacts, it really comes out to be a much bigger impact than just designing something from the ground up for every component of it to be able to be recycled. So we chose plastic, but a specific kind of plastic that I knew was the healthiest possible plastic that was not going to leach into the plants that was recyclable, where every single component of them is recyclable except for the pumps. So yeah, once you start going into the realm of getting to the possibility of doing custom manufacturing, you can do that at a much lower carbon footprint than what you can do when you're doing DIY with a whole bunch of things that we get as consumers. All right, thank you. Excellent. Thank you so much, Brita. Everybody give it up again, please for Brita Reidy. Thank you.
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In my favorite TV show, Connections, produced in the '70s by the BBC, Host James Burke traces modern innovations back through time, showing how one person's invention builds upon another over millennia in a delightfully asynchronous collaboration that gave us our modern industrialized world. Unfortunately, industrial innovation has now caused environmental problems so deep that our very existence may depend on fixing, quickly. If climate scientists' predictions are accurate, we do not have several millennia more to invent and market "ecological solutions." We need to accelerate invention, learn faster as a species, and integrate more symbiotically with the rest of our environment. We need to design faster, accelerate public buy-in, and work out the economics. For that, I say, "Let the public help!" For three years, I have been harnessing the passion of ordinary citizens around the globe in a mass collaboration to solve environmental problems ourselves as so-called consumers. As an online community, we designed and engineered Windowfarms, vertical hydroponic gardens that let you grow some of your own food in small urban windows, shaving the carbon footprint of your fresh food. Our community's success lies in building upon one another's work in a process we call R&D-I-Y, or research-and-develop-it-yourself. We have learned cultural practices, economic models, and ways of sharing that reach beyond through the boundaries of formal applied sciences and welcome a public eager to fight the good fight. We're getting broke, broken, and forked for the Planet.
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10.5446/21393 (DOI)
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My name is Kristin Zeyer and I welcome you to this, we hope to be an interesting panel discussion on the role that social media played in the protests last year, swept across North Africa and the Middle East. As we all witnessed them, they were pretty dramatic events and much has been said in the past year since them about the role social media has played. There's been a discussion, was it actually social media, was it the new media ecology that actually helped to empower people to take to the streets or were other factors involved? What role did social media play? What role does it continue to play? And then I think the other question we want to look at is the demographics of that people powered protest, those who are involved in it. What are the limits? What are the benefits? What encourages people to get out there to participate, whether it be through social media or then taking the final step and taking to the streets? And what discourages them from participating? Please ask to answer some of those questions or maybe go even further and ask us more questions to think about which we can then reconvene next year and see if we found any more answers. Our two people who have been investigating this issue from an academic level, they've been conducting surveys, they've been analyzing the role that social media has played. And with me today are Fadi Salam, who is a teacher at the Dubai School of Government. He's been examining in a series of reports the role that social media has played in the Arab world and he'll have a presentation on the demographics and the social structures at stake here. And we also have Sainib, she said that I didn't have to say her last name, I'll try it again, Tufekci, who is an assistant professor at the University of North Carolina in Chapel Hill and she's also been investigating the role social media has played and especially the interaction between technology and society. So I'd like to welcome them both. We're going to start with Fadi. Each one of them has about a 15 minute impulse presentation after which then we will hopefully have lots of questions from you and that'll take us up to about our hours time. So thank you, Fadi. Thank you very much. So I'm going to start with throwing some numbers at you and then a few photos and lots of questions and maybe that will raise some more questions next. So what was the role of social media in the Arab Spring? There was good, bad and ugly things that happened during the past year and to start with let's get this question out of the way. So was the Arab Spring a Facebook revolution? Show of hands? I can't see anything. Probably I'll say nobody raised their hands. But the interesting thing is if you ask this question in Egypt, usually you get a lot of people raising their hands that it's yes, a Facebook revolution. Let that continue to be a question to be answered later. So would it have happened if it wasn't for all the iconic activists or they weren't activists at the time. But there were people who died and their death, their suffering was used, they became icons, they were used using social media, it was distributed over YouTube, Facebook, Twitter and then fueled into traditional media. So would it have happened if it wasn't for social media, penetration and a critical mass of users in the Arab world? That's another question. So let's deconstruct what happened in the Arab Spring. This is very simplified but I will use it anyway. It was a demographic revolution of sorts. First and foremost it was there was a young population, very young in the Arab world, there was a youth bulge or so-called youth bulge, a massive unemployment that existed for a long time with hundreds of million jobs needed in the Arab world and there was a social revolution of sorts. One that created or based on social, new social norms that existed in the society in many Arab countries where expectations were becoming different, people were thinking that good enough is not enough anymore, that an economic and democratic freedom is something that you should be looking for and then there was a technological revolution of sorts and for that there was a critical mass of users across the region in certain countries that use technology with increased accessibility, with less costs and with more know-how. So what did that materialize into? For example, let's take Facebook. During the past year it grew from 18 million users in the Arab world, that was in October 2010 just before the Arab Spring, up to 34 million in October 2011 after most of the revolutions and then it slowed down again but still it grew up fast, up to 43 million users today. And these are numbers we are just producing, these are your privilege, this is the first time I'm showing these numbers. So this is how the penetration of Facebook looks in the Arab world today. You have countries with up to 30, 40% penetration rate, most of the users are under 30 years of age or 70% of them actually, women though are only 34% of the users. If you look at Twitter, these are all new numbers also at March, the active Twitter users in the Arab world today are around 1.5 million and by active users, I mean people who at least tweets once a month. This is based on Twitter definition of sort, they actually define it as somebody who accesses their account once a month but that wouldn't be as accurate in my view than this one. So there's around 8.4 million users of Twitter, most of them do not tweet but read or at least maybe not even do that. And there's around 173 million tweets generated in March this year. So let's ask some questions. What are the changing perceptions in the post Arab Spring based on social media? Is it a tool for women empowerment? This is based on, this is a questionnaire that we actually distributed across the region. I will not present the results but all of the results of many of the questions I've raising here, the findings of our surveys are available in the Arab social media report which you can download on the website below. So does it close or bridge the virtual gender gap? Is it a gender equalizer? In some of the answers, some of the questions we raised in the survey shows that actually most of the responses from men and women are almost equal. They view the role of social media playing in women empowerment very similarly in many levels. Did it revolutionize media consumption? Another question but I will skip. Did it enhance freedom of expression? These are also the findings based on Egypt, UAE and Saudi Arabia of our survey. These are snapshots in time that may change after the survey was taken but these are at the time of the survey taken. These were the impressions that we got. So let's talk about the good quickly. We also, the photos, the euphoria of the Arab Spring and the Arab revolutions and that materialized into something in many countries or some countries at least into a more democratic state while others are still in transition. However, what we know is that it actually a large number of the population in the Arab world, 43 million of them today, have new social dynamics that affects their lives. The use of social media by many of those young people made trust transmittable through some of the communities. In other words, if you look at how the activists use social media, not even activists, even people in civil society, it lowered the cost of creating a trust relationship between different groups. I mean, this is arguable but if you go in secret groups on Facebook and see what activists do and how even without them knowing each other they put themselves at risk, I mean, their lives at risk, that will give you an impression that even by being in such a secret social trustworthy connection helps in a way to push activists to do something. What we also know is that there was a shift in 2011 in the uses of social media from primarily social users into political users. So more people using it to disseminate information, to engage with citizens, even if you're a government, to organize protests, citizen journalism, other than the previous ways of sharing media and entertainment. And when we asked in Tunisia and Egypt and during the revolution, we got around 80 to 90% of the people responding at the time, Facebook users, saying, this is the respondents of the survey, up to 90% saying that the users of social media or Facebook during the revolutions was primarily political, either raising awareness or organizing protests or others. How are they using Twitter? If you look at the hashtags, the top used hashtags on Twitter from February, we also had results for September and March, this is in the Arab world. They all correlate with the revolutions at the time. Today in March, it's Bahrain, that's the second one is Syria in Arabic, then Bahrain in Arabic, then Syria in English, then Egypt and Kuwait. But the most, if you like, the most critical thing that probably social media example that social media had a role in is how the demonstrations were ignited in many countries. In many countries, it was a Facebook event or a page of a call for a date, the date as set on Facebook or using other social media, but primarily Facebook, that generated a point that everybody decided to go out and take it to the street for a certain cause. It materialized into protest in every single time other than one, which was Syria in the first call for demonstration in February, and that was because social media was closed, blocked for three years before that date in Syria. That's one reason. So what about the bad side? This is the stuff that if Guinea-Morazov would like, really. So by the way, these are just photoshopped photos, they're not real, just in case you're wondering. So what was the reaction in many countries? In Egypt, the first reaction by the government was to pull the kill switch, let's close the internet. People are using it to demonstrate, to organize, and this is not good. So that was the reaction for six days during the revolution in Egypt. The government blocked the internet. However, that backfired. People in Tahir didn't care anymore. The ignition started, and it took a life on its own, and even they created their own Facebook wall in Tahir Square offline. So what was the primary impact of blocking the internet in Egypt? This is what we asked in Egypt and Tunisia during the revolution, or just after them. And the reaction that was surprising a bit at the time, that it was a positive thing. Most of the users, or most of the people that answered this question, said that it was a positive thing. It made people more determined and pushed them to, pushed the undecided people to take it to the street because they felt that one more right was taken away from them. So some governments learned from that mistake. Five days after Egypt unblocked, blocked, and then unblocked the social media and the internet, the Syrian government actually unblocked social media sites, which was blocked for three years before that date. So they saw that, one, this is something that could backfire, and now it's growing in popularity. Plus, many would say that they actually wanted to monitor what's happening online. But that's also taking place. So, I mean, this is not new in the Arab world. This transparency aspect has been going on for decades. I mean, centuries ago, this was, this is the Umayyad mosque in Damascus, for example. This is the big thing in the middle is where the government holds all the treasury, all the gold. And that's in the middle of a mosque, the grand mosque of the city. So if you are in the government and want to take money from the treasury to use it, you would have to walk between the prayers and see that everybody would know what you took, how much you took, et cetera. But that information still wants to be free today even. Even during the demonstrations, when everybody was blocking the internet in some governments, people came up with very innovative ways of disseminating information. Other than the normal Bluetooth dial-up browsing, anonymous browsing, the satellite phones, you know, one of the most interesting ones was to make this photo on your left hand side. This is a makeshift battery with a speaker, with a USB connection, and sometimes with a wireless controller. And that, this is put in different areas around Syria by demonstrators, just to, you know, when the internet is disconnected, even the electricity is sometimes disconnected from neighborhoods. People will use this to either organize, you know, you put it somewhere in a tree, in a rooftop, whatever, and either use it to organize or even just to blare revolutionary songs. The other bad thing I would say about the social media uses is the most modern, postmodern policymaking and the informational weak link. Many of what's happening in the policymaking cycles in the Middle East today or even on the international level is based on social media as a primary source, especially in cases like Syria again where access to information is not available by journalists or the media. So social media sources generate or move the information from the ground. Citizen journalists pick them up, mainstream media picks it up, then it goes to think tanks and organizations and goes into the foreign policymaking cycles which also recycled again through social media. That's a weak link. Nobody should be having such power to reach, you know, some of the information generated on social media are used in the United Nations Security Council, for example, without proper checking. I would call it the Friday names for in policymaking in many ways. This is related to how the Friday names, the very popular, every Friday has a name in many of the revolutions that are still taking place, especially Yemen and Syria. You have around 20,000 people on Facebook voting for a name of that Friday. And sometimes that name would be, we want arms to fight against the regime. And that 20,000 people on Facebook, they're anonymous, they're mostly not Syrian, for example, if you're talking about the case of Syria, and they're determining the way that this goes into the policymaking cycle because this is picked up by Al Jazeera and it's put as this is what the people want and then that's picked up by policy makers justifying doing something like arming the rebels, for example, based on few thousand people who decided this. And this is very powerful. And then there's the post Arab Spring Twitter diplomatic tensions. I mean, the most recent one is Al Jazeera's case that created a buzz between Egypt and Saudi Arabia where the embassies were closed. And this is something growing. I mean, people are using it in different ways, in a chaotic way, in different countries. So what is the impact on media integrity? I touched this a little bit, on this a little bit. But there are unprecedented errors in reporting in the Arab world based on over-reliance of social media sources. And you have today a restrictive information environment by the government and an avalanche of information coming from advocacy groups from activists. This effectively means that many of the media becomes a victim of sorts when they don't have access, sometimes willingly so in many Arab countries. There are many emerging risks which I will not be going through a lot. But it affects the internet censorship, monitoring the legal implications that are generated and created today, the propaganda wars that are taking place, especially in countries where the population is split. And there are hate campaigns by both sides, amplified by social media. And then there's opportunism. I mean, this is the ugly side of the whole thing, in my view. There are many businesses created based on this lack of accessibility to information in many of these countries. There are professional perception management companies and techniques, social media-based regime change consultants that get usually contacting me all the time. And social media, revolution businesses. And then there are the celebrity activist phenomena. And this is something that's, you know, I'll keep it on the label it as the ugly side of the whole thing. So finally, just a quick two lessons out of many maybe, is that maybe people should be realizing that activism is not citizen journalism. Which one is it? Which one should be relying on? I mean, there's a, many people are merging the two, especially the activists, which became, which lead to a media becoming a victim for political struggles. And then, you know, creating this perceived reality is not a valid or legitimate form of advocacy, because it can cost lives in many ways. Then there's the media credibility and integrity that is also very much affected after the social media revolution, if you like, in the Arab world. There are limited fact-checking. There are, there's over-reliance on social media sources. And there's no liability, you know, spreading the information. I was in some of the largest media companies in the Arab world watching in the newsroom. I was in the newsroom and I watched how the news took place. I mean, somebody on Skype asking a question for an anonymous person somewhere nobody knows where. And he was saying, she was saying at the time, how many people were killed in homes today? And she got immediate responses. 31. You know, 30 seconds later, it appeared on the screen on Al Arabiya without any fact-checking. That's too much information. What if the person which mistyped 31 instead of 13? Anyway, reality is bad enough, nobody needs to amplify or make it worse. And this is in a way, many citizen journalists are doing the same thing. I'll leave it here and maybe we can talk about this also in the questions afterwards. So, Zeynep, now you're going to take us a little bit further and address why this is such an interesting topic and what we can learn from it. Are we ready? Can we? Okay. My name is Zeynep Tufekji and I can be found pretty easily either through Twitter or on my blog, TechnoSociology.org. And I will be putting up the presentation and a lot of the numbers there. There are already some of it there in case you're trying to find it. And as you said, I'm an assistant professor at University of North Carolina and a fellow at the Harvard Berkman Center for Internet and Society. So, I want to start by talking about, is this better? Okay. I want to start by talking about why the social media and the new media ecology helps break the autocratic model the way it was practiced in the Middle East and why it presents a challenge. I mean, we all know, as Fadi said, there is something about, you know, there's something with Facebook, there's something about social media, and we know it played some sort of role. But what is sort of the conceptual understanding of what role it played? And I want to start, but I really am not wanting to discuss, was it Facebook or the people, not because I don't have an answer, because I think this is really the wrong and misleading question. Is this better? Yes. All right. I could just yell instead. That would work, okay. So, I think the question was it Facebook or people has the wrong conceptualization of what Facebook is to begin with or Twitter is to begin with. It's like thinking of the online world as if it's the matrix and we live in the Zion and these are two separate things and we just transport from one or the other. That's just not the way it is. Just the way the telephone and other forms of communication is just part of one world. Facebook and Twitter and all other social media platforms are not in a separate world. It's just integrated into this world and in fact that is exactly why they are powerful platforms. So, I just don't have, I think the question is wrong. So, I also think was it online or offline is the wrong question because why is it an either or? What's actually interesting for me is how is the public sphere transformed when you have these new tools? How is the infrastructure of connectivity altered? And how are bits and atoms integrated and therefore changing the way we do things? And this is important. When I say I don't want to discuss was it online or offline, I do not at all mean to say that there is no difference. There are no different properties between the online worlds of bits and offline worlds of atoms. In fact, there are quite different properties just because the way the internet is organized and the way networks travel and all sorts of models of control of people that are based on the assumption that you can physically control information, that you can physically control the atoms are being challenged and a lot of industries are being disrupted exactly because atoms do not have the same properties of sharing and copying and travel that atoms do. To give an example, the music industry has been facing quite a challenge because our copyright laws, at least in the United States and a lot of the western countries, are based on the idea that when they sell you something, they're not really giving up their control over it but because it's a physical thing like a CD or a book that you can't just make three billion copies of it. So the properties of atoms that they're not easy to copy is what our copyright laws are based on and they're being challenged. In autocratic countries and also in more developed democracies too, modes of power based on controlling physical people, information are being challenged by the integration of a very different kind of infrastructure of connectivity. So how do you control the public sphere and why do atoms change how the public sphere is controlled? One thing is pluralistic ignorance and this is a political science term that I find quite useful in understanding why social media makes a difference. I'm going to give an example I've been giving in lots of talks and I'm going to get in trouble one of these days for giving this example. I hope it's not this time. So let's assume that you guys are all really, really bored at the moment. You're thinking, what is this? What is she talking about? I really hope, I want to go and get some coffee. What time is it? And you're really fidgeting and you're unhappy about this. But you're sitting there by yourself thinking she's really boring. And you're probably not going to get up in the middle of my talk and say, oh, you're boring and just walk out. It's kind of rude and we're socialized into, you know, we're social creatures. We don't really go and disrupt people. I give this example in classrooms too and I'm really afraid one of these days somebody's going to be like, oh, wait. But let's now assume that you all have a back channel that our internet is working really well and you're all able to communicate with each other. And somebody starts tweeting, she's really boring and I hear there's coffee outside. You can imagine how this could actually break down what political scientists call pluralistic ignorance where you are in fact, your privately held views are in fact the majority but you do not know this because there are various barriers to sharing your privately held views so that everybody finds out, oh, wait, we all think this similarly. We all want to walk out of here. We've all had enough. You see, that's pluralistic ignorance. And you can really see why in a country or a region where the public sphere was so severely controlled, breaking of pluralistic ignorance where you already have unpopular regimes can be so powerful. And another thing that these governments had been doing to control the public sphere was this proportionate punishment of dissent. What I mean by that is let's assume that you really decided you had it and you're going to get up and walk out anyway. But let's assume that I have a bucket of water that I'm able to dump on the very first person that walks out. That makes it quite unlikely that you'll be the first one to do it because I have the strong way of punishing the first person that walks out. I may not have a way to punish 100 people but if I have a very severe punishment for the first one to get up, that really dissuades people. And we've seen this disproportionate punishment of dissidence is a very integral part of every autocratic regime. It's not just that the Chinese government is afraid of a single blind lawyer going from village to village. It's not that they know one person isn't the big deal. It's the example. If we let this person, what will the others do? That is how it works. That's why we see torture and very, very disproportionate punishment integral to a lot of these regimes. Now, what happens when you have a system in which you don't necessarily have to be the first and you can coordinate so 50 people can get up at once? See, just because autocratic regimes can operate and punish without institutional checks and balances does not mean that they can actually punish every dissenter if 100,000 people are in streets. They have constraints on their resources. They can't do everything. And finally, that is a way of preventing a cascade of dissent from happening. So, Fadi already talked about this. This is the We Are All Hallowed site website which was where the January 25th protest was first announced and called for. And what this did in Egypt was give people a place and a date that they could show up right after Tunisia where the sense that change was in the air. But instead of going out 20, 30, 40, 50 people at a time that they had done year before and the year before, they had January 25th protest before. It's just 150 people showed up and then 5,000 police showed up. It's not very useful. So you had hundreds of thousands of people clicking on, I like this. Yes, I'm going. As a friend of mine said it must have been the first revolution in history where people said, yes, I will be attending the revolution in response to an evite. And then showed up. And the very first day we had thousands of people show up, which is very important because once you have 5,000, 10,000 people, it's harder to punish a few and then this can start a cascade. The public is a meta concept. It's not what you know. The point isn't that Egyptians learned that Mubarak was corrupt. The point isn't that Tunisians learned that Ben Ali was corrupt. The point is using their new means of information flows, they could talk to their fellow citizens that they agreed and more importantly maybe they could make their calculations on how to proceed together rather than being punished one by one. So this is, I'm going to show you guys, let me just say, I'm going to show you guys a bit of numbers and these are from a survey we did during the unrest in Tahirir. This is a protestor survey. It's a sample of 1,000. It's a snowball sample which means we did not randomly sample. We tried a randomly sample but the situation was so dangerous that it just wasn't possible. So it's not a perfect representative sample but it is quite large for this kind of survey if there are academics among you. These are usually very hard to do and we did this during the unrest so it was even harder. And this was published in the recent issue of Journal of Communication. It was no paywall for the month of April. Unfortunately, I believe it's gone back to paywall but if anybody wants it, just find me and I've been emailing it to everybody and I'm looking for ways to make it more accessible. So these findings are all published in a peer review journal. I'm just going to show you a few numbers. So, wrong way. So where did you first hear of the protest? Almost half the, I will put these up, almost half the protest, they're heard of it face to face but about 28% heard it first from Facebook. Again, this is the online offline merger and to me this is striking because Facebook was an Arabic only in 2009. So in two years we're seeing how it became such a prominent sort of conduit of information. So did you produce and share visuals from the protest as it's happening? About half the participants in our sample did not but about half did. So just in the sample, there are 500 citizen journalists just in the sample. So if you kind of extrapolate, keeping in mind that this is not a representative sample, even if, you know, maybe not 50%, let's say we found a particular active group, even if 10% were doing this, that means you had tens of thousands of citizen journalists in Tahir at the time. You can see why it's so difficult to keep the news from getting at. And it's an ecology, let me show you like, and Facebook was the primary means through which people shared visuals. Now Twitter for example is a small percent but you have to understand, it's an ecology, right? So because it's an ecology, Twitter played a key role as a bridge. So it's not just about the percentages, right? Twitter was very useful in getting the news from Tahir to outside the world and Facebook very often useful for within the country because of the lightweight of Twitter. So you can't always just look at the percentage but the percentages themselves are striking. So this is a picture I took in Tahir during another protest and right there on the 8th floor of that building is the Al Jazeera camera. That's a famous sort of camera that protectively hovered over. And that's just a protestor, I took his picture. He was wearing those Tahir square freedom Facebook photos which they're selling to tourists around Tahir now. That's kind of like what's become instead of selling you little sphinxes and pyramids, they sell you Facebook t-shirts. You got to make a living. And it's a great time to go to Egypt by the way. I know there's a lot of scary news coming out but there's not that many tourists and there's a lot of things that are quite nice going on. So people, he's taking a photograph and a lot of this gets shown on Al Jazeera partly because Al Jazeera didn't always have people on the ground but it didn't happen in a vacuum. There were networks of citizen journalists who had been working with broadcast organizations like Al Jazeera that played key intermediary roles. In fact that's what I mean when I say online offline integrated is for example, and I can, you know, this conference itself, I have heard from many activists that I keep hearing of a couple of things. One is Global Voices which is this organization that I know lots of people are from and people tell me again and again that it played a key role in making people around the region meet. I hear about Republic people from the region, sometimes from different countries met here for the first time in person and that was important to their, you know, establishing their trust networks. I hear about things like the Arab bloggers meeting in Berlin 2009. So there was this offline face-to-face trust network on top of the online network, on top of the Al Jazeera citizen journalists network that were all mixed together that helped create a kind of information flow that just was not possible before these tools and that autocratic governments did not at the time, at least the Egypt and Asian know how to respond, but as Fadi explained they are now trying very hard to learn. So I just wrote that out in words but this isn't my article and I will like, you know, this is my blog. I did what we call multivariate regressions which means we control for demographic factors to see how social media users behave, to make sure that social media is not just a proxy for education or something like that for example, it's not just that the educated people were more active and they also happen to be social media users, it's just for academics among you. The short of it is, my finding is that when you control for other things like age, like education, what you find is that social media users who are more active in the protest, they were a lot more likely to be there on time in that crucial first day, that people who had internet at home were more likely to be in the protest but it wasn't just this broad internet, people who were using the internet for socially and through social media were in fact through lots of sort of multivariate analysis they were there in those first crucial days. So this is a finding. So overall Facebook was a primary mechanism for producing and disseminating content. About half our sample was participant as citizen journalism and all of that is right. I just put the sort of reference there for people who want more details and as I said I will be happy to send more. So it's not simple though. Social media is more participation. Lots of questions that we'll talk just a little bit. What more participation means is not yet, I mean it's not some, oh more participation equals more democracy. Democracy is a lot more than participation. Participation can lead to things that are not always positive. It can be complicated. There's a lot of new ways and governments are adapting and trying to respond by reasserting their control over the public sphere which has been challenged I believe pretty much everywhere and you talked a lot about that. So if you depend on these things that I talked about, if you are a government or a business you depend on your information monopoly, control over gatekeepers, pluralistic ignorance, divide and conquer, advantage of speed over the people, if you depend on those factors to run your business or to run your government, I believe that there is change and challenge in the air and here they come and people are here and we will see how this plays out. So thank you very much. So now I think we have some time for questions from the audience. Please just, there will be microphones going around if you wear the microphones so we can see. Well if you stand up and ask questions, direct them to the Fadi Otsenip then please. Anybody have any discussions on the issue of demographics? Fadi presented the good bad, the ugly, here's a question. Thank you very much. You hear me? Thank you very much Fadi for your excellent presentation although I must say I haven't gone really through the report that you mentioned and the facts that are mentioned there are absolutely fascinating what new social media has done. Now the question is regarding social media and the Arab Spring. Although Libya and Tunisia fall in North Africa but it was still called as an Arab Spring. This is something that we need to think about. Now the second question is, like I said I am not sure what are the facts mentioned in the report but could you please highlight certain issues that for example there are still countries where there is a monarchy, there is a kingdom ship and the social media doesn't really play a role. Is it because we still need oil from there or is it because you know we are giving them a little bit of a room, benefit of a doubt, certain countries where women can still not drive the car but is there a case that there is no massive unemployment there or there is no youth there who would like to use this social media? Secondly, the social media itself, the technology somehow played its role in this region, the Arab region or Middle East over and again. It's not a new thing. Back in 79 when Imam Khomeini was leading the Iranian revolution, they relied a lot on technology as well. Remember the facsimile machines, remember the tape recorders, that was also a media revolution. Why, maybe if you could highlight how you have mentioned in the report, why these countries, this region rely on this new media which is more synonymous with the western technologies. Thank you. Fadi, do you want to answer that? Sure. I think the first question was regarding the naming of the Arab Spring, if I'm not mistaken. I mean that's a larger question but I mean there's always somebody who will not be comfortable with some name or another and there's whatever you consider is politically correct, go with it. Some people would like to use the name Arab Uprising, some people would use Middle Eastern Uprising, Awakening, all other kinds of names. It's just one of those names that, I don't like the name globalization but I use it because everybody does. Anyway, so the last question, the other question you asked is the Khomeini tape and how it, you know, the tape recorders and how it influenced or was the main driver if you like and that was considered the main driver of the Iranian revolution at the time. True, information flows in different ways. It's faster using social media. There are more links between different groups of people in society and there's a trust element and it's more interactive and user generated. It's not top down like what was in the case of Khomeini. So it becomes faster, less controllable and that's the fact that, you know, when you have a critical mass of users using social media and they create these endless links, trust links between each other and if one of these links generates information it will be considered as real and right and something to act upon by the others in the trust circle. These are all elements that should be considered. So there are virtual civil society movements if you like created in the Arab world in these countries where they didn't exist in real life. They didn't have access to, people didn't have either civil society movements because the governments didn't allow them. They didn't have free parliaments because there was no real elections or representation taking place and there was no free media and suddenly there was this channel with a critical mass of users using it to effectively create changes and it worked. And as Zaynab and in my presentation these are some of the elements of how it did work. Yeah, yeah, go ahead. Well the Arab spring name comes from actually it's like a so back to 1848, the spring time of the people which actually happened in Europe and back then too both the railroad communication and the railways that were just being started in Europe and telegraph which was first starting to spread the news were a key part, obviously not the only part. I mean neither of us is saying that for that. So I completely agree that social media predates digital media. Absolutely. In fact the Iranian revolution of 79 is a very good example of small media, interpersonal media versus challenging the control of the public sphere. There's a great book by Annabelle Cerebrini, Mohamedi called Small Media, Big Media in Iran 79. If you look at it you see the very same dynamics. It was just more crude and slower at the time. And in terms of other places where there is social media but not necessarily in uprising I don't think either of us are saying that it creates dissent where there is not. It is more a way to challenge the public sphere where there is dissent and in fact even in the Gulf region which is much better off we have this ongoing fairly broad, it's not maybe as broad but fairly broad uprising continuing in Bahrain and social media is a big part of the story. So it's not like social media is this magic wand but it does change the dynamics when there is already dissent on the ground and people are just looking for a way to come together and organize. Okay. There was another question here. Thank you for both of your talks. I've learned a lot. I'm interested in the role democracy will play in future. We could in the West very good rely to the uprising for freedom. And now in Egypt we have a parliament which consists of the Muslim Brotherhood and Salafist parties. And I'm wondering is this just my western bias or is it a problem? Is it a problem which emerges that we'll have in the future these modern middle classes who can afford social media and like social media and the rural people who vote for conservative parties. Will we have a permanent revolution even when there is democracy? Is that a one of the particular speakers you'd like to answer that question or which of you feel comfortable? I'm not sure which of you can answer this. So again, I mean, let's take a look at how social media demographics grew in Egypt, for example, just for the sake of the example you mentioned. It started with in the beginning of 2011 or end of 2010 with a small number around a million or a million and a half people on Facebook. That's taking Facebook as an example. Today it grew up to around eight. And at the time it was primarily people with English language abilities, middle class, young educated students. These are the main demographics. Today if you look at the usage trends on Facebook, you would have, there's a larger portion of the user base in Egypt which was at the time around 50 to 60% English speaking or people who were using Facebook in English. Today it's much larger who are people using Facebook in Arabic which means that it is growing beyond the elite. It's reaching the masses. And this is growing very fast in terms of number of users. So what I'm saying is that social media, if it reaches and becomes representative or people on social media become a representation of the people in the real society of the population, then you will have a better representation of what's taking place in the society. Not just the view that the elite are leading with the social media revolution and providing democracy and freedom of speech. You will have a Pandora box. You will have the society itself being represented and everybody using the same tools to push their agenda and try to reach the political office if that's the case. So yes, you will have more representation of maybe conservative groups, maybe even the government will have better use of social media to actually oppress these movements. Even extremist groups, even violent groups are using social media very fluently in some of these countries currently. So it will be whatever exists in society. This is what I think. It's not going to be pushing freedom or democracy or whatever. It will be just amplifying or a new channel of representing what's happening in society. I have the same. Hi. Thanks. It's a really wonderful talk. I wonder, it would be great to hear either of you actually go a little bit deeper inside the data on social media use. So I love the media ecology framing and shameless plug. Christine and I will be talking about that this afternoon in the Occupy Media Ecology talk. One of the things we found in looking at how social media is used in the Occupy movement is that really when you look inside the broad use figures, there are people who spend lots of time developing digital media skills and produce really nice videos and are followed by many, many people on Twitter. They're sort of the reproduction, I'm not going to call it hierarchy, but there are some people who are very effective and become known and trusted and followed by many. And I'm not saying that as a critique. I'm just really interested in the dynamics of the citizen media and activist media spaces where some people do emerge as sort of key actors in the new media spaces. And if you could talk a little bit more about how that works inside the context of the Arab Spring and those uprisings, that would be great to hear that. More fine green analysis other than, oh yeah, these are the broad percentages of people who like something. Yeah, I'll let Zanef start because she has more followers on Twitter than me. Well, that was Sasha Kostanza, Chuck, by the way, who's doing research at Christie on the Occupy movement. And one thing that I find fascinating about the Arab uprisings and the Occupy is exactly what he says is that there's actually not that large a network of key people all who have been working at their media skills, their networking skills, their political organizing that form the backbone. And that's kind of what I was alluding to by saying there's this huge sort of smaller network embedded in this larger network, embedded in these big... And in the Arab Spring, in the Arab uprisings, the network goes back when I talk to people maybe to 2000s and the first attempts are like the anti-Iraq war protests, Cairo 2004, 2005. Those are when people started learning how to do stream, how to organize. And you see the way you look at the Occupy movement. I meet people and I'm like, don't I know you from Seattle 99? And they were there trying to do the same thing. And they have built... So there's this incredible knowledge infrastructure key people that you don't necessarily see. The second thing is that, and I wrote about this, that is this really a leaderless revolution. Social media is an open space that is correct. But an important thing to understand is that open spaces of networks can throw up hierarchies, and I will use the word hierarchy, completely fine, more easily sometimes than structured spaces because in an open network, you have a mechanism which you might call the rich get richer, where if you already have some attention on you, then the media come and interview you. And then you get more followers on Twitter. And then you have more of a voice and then media come interview you. So in my first initial analysis, for example, during the first few months of the uprising, you could clearly see a few like elite leaders go very quickly up where everybody else was sort of more just sort of hanging in there, increasing but not at the same rate. And if anybody's into network theory, that kind of preferential attachment throws up what we call power laws in which there are a few people with very high levels of visibility and lots of people with less. You see this in the blogosphere. You see, so it's not a flat space. It's an open space. That's different. But one interesting finding that I'm finding, this is kind of new and this is Alex Dunn's research that just got published after the talk I will go tweet it out, is that the network, even though it's hierarchical because of these properties, we have these unfortunate field experiments when somebody gets arrested. So it's an experiment when you have a hierarchy and somebody on top is taken out and what happens. What you see is that the network seems to spring up a new hierarchy. So it's quite more resilient. So it's not like the civil rights movement and you can go and assassinate Martin Luther King. It's not like you can take one person out and then the network collapses because it is a network. It is different kind of institutional. But it does equilibrate back into a hierarchy. So I think this goes back to the question of what are we going to see? Is this going to be more democracy? Is this not? This is open spaces? Yes. Flat spaces? No. Okay. I've been signaled that we don't have much more time, but there was one more question. Can we take two more questions? Yes. Okay. Great. Hi. I have two questions for you. I'm working for an institute and we did some research also on the role of social media in the Arab uprising. So the first question is, as far as I got from your presentation, the numbers were only from Egypt and they were only from the Tehrir Square, actually. So how far is it transferable? And the second point is, the role in general of social media, I see the impulse that it gives. But even if we have like 5,000 citizens journalists for the momentum, in total, like the number is not much. So therefore, if you take the whole number, it's not really a representative or a big part. It brings momentum, very true, but it's still just a minor part, even like 5,000 people. So my research is, this one is Egypt, Tehrir, Square, I mean, it's exactly what the protestors survey and that's what we meant to do. Fadi has broader regional numbers so you can look at that. And for the second part, that 500 citizen journalists was from my little sample of 1,000. So if you project, you're talking about tens of thousands, maybe hundreds of thousands of citizen journalists. I, once the news director of YouTube said to me, and YouTube has a news director, YouTube is probably the biggest news organization in the world today. She said that after about an hour of anything of significance happening anywhere in the world, they get video. We've seen the case of Syria in spite of enormous efforts to suppress, there are hundreds, if not more, video coming out every day. Who gets to see it? Does it make sense? How do you understand all that? I completely agree it's complicated. But I think the classic kind of information suppression where something would happen somewhere and you just wouldn't know what happened and then you'd find out five years later, one year later, you'd try to go back and reconstruct. I think that era is effectively over. I'm not sure what it will lead to but I think that's just done. Okay. I see that we, I'm going to try and bring it to an end. I know there are more questions, the more, both of you talk, the more questions there are. So I would encourage both of them have posted here where they can be reached on Twitter or how they can contact you. I think that's great. And maybe you'll stick around if somebody wants to ask you questions during the break, that would be excellent. So thank you very much. Thank you both for coming and found a very informative presentation. Thank you. Thank you. Thank you.
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In this session, two scholars who have extensively studied the role of social media in the Arab Uprisings will present findings (both theirs and others) as well provide a guide to new issues and questions raised by these developments. How and why did activists across the region turn to the Internet before, during and after these revolts? What role did various social media platforms play in the political process? How does the emergent new media ecology blurs lines between old/new/mobile/Internet media? From Al-Jazeera to video-phone enabled cell-phones, from satellite modems to mesh networks, activists and journalists in the region have displayed some of the most innovative uses of new media tools. Governments, though, are responding.
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10.5446/21396 (DOI)
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Okay, this is the last session of today, right? So I didn't see so many people here coming in, but more people are entering. So I want to ask more questions today instead of talking too much because I want to see if not it's not only my personal sharing is about how people share in your spirit back to me as well. That's about shareism. So shareism in definition is a very short, the very shortest definition is the moment of sharing. Why you share, how to share, and what's the result of sharing. So it's a theory about sharing. It's a kind of new theory we are developing, but actually it's from the people itself. So today I want to just want to share a little bit about shareism theory by showing some cases we are studying from the me, a very simple, small idea in our mind, how it can transfer into action in our real world, in the physical world. So it's always the question from our surroundings that why we share, it doesn't make sense, we only share information. We should try to do something in the real world. Whenever I would argue that it's just because of sharing, because of the message and memes spreading, adding up and amplifying themselves that we can make the world change. So it's the whole theory of shareism trying to discover the economy model of sharing. For example, I will ask you that why you are here today. The question is very simple, and you could answer me, maybe I want to get some information, get some knowledge from this kind of discussion, a lecture. The same question to me, why I'm here by myself? I want to share, definitely. But why I want to share is because of I can judge, I can absorb their energy from you guys because you come here to listen to me, to give my the courage to speak out, to talk about, to share more, and I feel it's a kind of fulfillment. This is kind of an economic model. I share art, you share me back. That's a basic model of shareism. We, it's the same thing to the Web 2.0 world, we experience for many years and we discover that the economic model is very much fire. Because many people share their information, share their knowledge to the surroundings and go through the whole social network, but they see real returns in their life. That's the economic balance we can see through shareism. So I argue another thing later I will mention, the more you share, the more you gain, the more you can get from your surroundings. This basic rule will take control of the future Internet world. I want to argue. But before that, I want to share you guys, can you see this? Technical guys, please. We need to switch to the slide. Okay. Anyone there? Okay. Perfect. I add this slide today, just before this, maybe 30 minutes before this talk. I want to share what is happening in China now. It's also based on the understanding of social media. So you guys maybe know this blind lawyer. Mr. Chen, he was protected supposedly very safe in the US Embassy the last whole week, after some Internet activists went to his village to save him from the house arrest of China of the local authority. And the US Embassy guys, including the ambassador, take him to the hospital later yesterday. Originally China government and US government reached an agreement to set him free forever. However, things changed. Originally, if in tradition, you know, event happenings, you know, we could say that the traditional reporters on media will say, oh, it's a good ending finally. And we published the report that the Chinese human rights record could have been reaching a new level, whatever. Yeah. However, it's just because of the social media yesterday. One the guy went to the hospital. People found that it's not really safe for him because his family member cannot see him in the fast forward yesterday afternoon. And the guards there provide prevent people from visiting him as well. And for the hospital, it's surrounded by many, many policies to stop price and people to visit. Also, the mainstream media started to deleting people's buzzing about this case online, it's Chinese social media website. However, there are still many people buzzing this case on Twitter, a blocked website in China because many people in China use VPN to access this kind of global social media. So in this case, people found that it's not a real final solution to this human rights activist. It's that it's going to be worse because of the agreement didn't really executed. And then many people started to question what's the deal between China government and US government. So afternoon, so many people started to question the two governments and the mainstream media reporting the happy news and those traditional media reporters, they cannot stand still there. They started to investigate this. And in the afternoon, all the media reports changed their tunes. So it's happened that in one day, it's not like the traditional daily newspaper reporting one story and changed the next day and it won't focus on the real time happenings like this. So if you search now, you can see many Twitter updates, maybe over 50, one minute, you know, will pop up to your timeline because everything is still happening. And today is supposed to be the China-US dialogue, the strategic dialogue happening. Hillary Clinton is there. And let's see what will going on with this case because many people are still worrying about the safety of the family. Okay, that's a real time thing happening. But we love to go back to the old time. When China was still in its prosperous age, there are many old inventions in China, technically. Like this machine is a very interesting machine that tried to separate the green from the pests and the straws. So it's a very effective machine to give people the food. And it's documented in a very early book back to 14th centuries. So it's very much advanced inventions in China. However, these kind of things didn't spread around the world. They kept in China for a long time for about 500 years until 18th century. And someone in Scotland, they used this kind of invention to make money because they copied this machine for many, many, many times. And people use this machine in different places and they generate, you know, they use this productivity tool to generate more money. And then advanced the tool to use the horse power and then use the machine power, you know, more and more to the advanced world. I won't tell that, I won't argue that just this machine lead to the industry revolution in the Western world. But anyway, it indicates something that in a closed country like in China, it's forever in 2000 years, it's a hierarchical world. You know, even there are some very creative innovations. If people don't really share these kind of things on knowledge, you know, things could not be upgraded, you know, could not be improved and cannot make money. However, in the Western world, they did. You did. So things changed today. We have many, many economic, you know, phenomenon in China now. One is very famous called Shenzhai. Anyone here knows what Shenzhai means? Oh, at least some of you, yeah. Even this, the plain meaning of Shenzhai is village-mate is something copycat, you know, from the real product. For example, like the iPhone 4, when the product released, just after one week, there's a copycat in China called the iPhone 4. You know, so the same, also looking the same, roughly same functions, you know, from the user interface. However, you know, the performance or the other things get different. And we have some other, this is a very interesting Germany-based, you know, reward called the plagiarism, I'm not sure if it's the right pronunciation. It just tried to reward, it's a joking to those copycat products, you know, because when the deaf and the air multiplier invented in the US, there's soon a Chinese copycat coming out. And also, up to the military industry, they copycat the US and Russian jet fighters, as well as the bullet train, you know, China copied many technologies to put together into their bullet train to be the fastest growing, fastest growing high-speed rail around the world. So, the question is, is Chinese, they can only, are those Chinese only copying or they also can inventing? There's a big argument of this, beyond copyright issues, the intellectual issues. I would argue that it's a very early stage of things happening in this country, because after long-term economic issues in China, they still need quite a while to learn from the world and they try to, you know, share these kind of things from their design to their, you know, every aspects of the products, then they learn to improve that. And I think it's kind of a good sign that many Chinese manufacturers, they're starting to collaborate with the international design studios, and this is kind of a new model to link the design powers from maybe other areas into China to make it into product. We see many projects from a website called Kickstarter. You know, many people put up their ideas online and they made this product in China to transfer the ideas into the real product. So it's a kind of idea traveling from somewhere, in the other word, into China with the manufacturing capability, you know, integration, so they can make the final product. This is a kind of a very good case of sharing. Let's talk about ten years ago when we think about sharing. It's a kind of anonymous word. Many people may be very familiar with this comic. It's a kind of Internet philosophy at that moment. One, two docs talk about Internet, one doc tell another the secret. Internet is so amazing because on Internet nobody knows your doc, right? Yeah, this is ten years ago, even twenty years ago. Many people think about Internet. But now it's changed. Sometimes on Internet, even the doc want to show off themselves. They want to seek those followers. And some people perceive the followers as their social capital and some people think that is fine. It's entertainment. So nowadays we see Internet actually the social media age. After the Web 2.0 technology improvement, we see so many new identities emerging, the real identities. Whether you use the real name or not is the identical thing to many people. They would love to start sharing from their social media centers. So many people started to grow their firsts around them. The fur is not the animal fur. It's the Internet kind of synapses to extend it to the world. It's like a hairy person around you. So you touch base the world with different synapses. Some with your Twitter, some with your Facebook, some with your Google Plus, etc. And different kinds of blogs, photo sharing and video sharing tools. So this kind of sharing is not so boring like the traditional sharing of your property. It's different property. If we share an apple with several guys, everyone can only get a piece of that, right? It's kind of a losing of those physical parts from you because you have to be very, very gentle, very noble to sharing this kind of physical work. So to an apple sharing is different. But for the idea sharing, for the information sharing, the knowledge sharing, like today's open causeware movement, the sharing things, it's not something losing. It's about generating new torrent of bigger things. So if you have the identity around you, I share something online from my original creation. I would try this kind of sharing along a social network, like some people visualize those things, how those ideas were amplified or enlarged in the social network. However, it's not the traditional Internet. We cannot find who is the original creator because it almost goes to the big enterprise or maybe published than Lucille identity. Instead, today's social network gives us a handle that everyone knows this is your creation. It's very much interesting to challenge the traditional copyright things. Why we protect copyright and intellectual properties before? Because we're worried about, we lose that because other people could steal that as their creations. That's a kind of fear in our emotion, our feelings. But with the kind of identity resolution, we can have this chance to redefine how intellectual properties could be protected instead of using the traditional enforcement ways, like the patent, like the trademarks, etc. We see through the whole Internet and can see how my ideas get across the social networks to be enlarged. So I just illustrate some people, interesting people in China. Some people may know Ai Weiwei, Kai Fuli, Qin Guangcheng, the lawyer, and the girl there in the right corner who saved Qin Guangcheng from his home arrest by herself. All these kind of things happening in China is based on not so long, just three years after Olympics, that's the social media booming. So Chinese government censored all those popular international social media websites, including Twitter, Facebook, YouTube, etc., flicker. However, the local social media websites growing up, they started to take the role as the media to help people to share their information from their daily meal to cute cat, to flowers, to their datings, whatever, you know, in China. It unleashed the power of Chinese people from the traditional closure of information. It generated a lot of connectivities between different worlds. I illustrate these people because they belong to different worlds. Ai Weiwei and the author, they belong to artists, and some guys left from the geeks groups, and some guys right belongs to the activists. They're not alone. They're not in their own bubble. They were connected. So the information may flow from those connectivities. I call it the circuit of information. It's just what we think about the brain neural network, as I mentioned later. So let's look, examine, try to examine a case. I won't talk too much because you all know this, the Latin case. It happened last year. One of the very interesting sharing of this Pakistan engineer, he was waken up by the US military helicopters, the sound, the big sound. So he felt that, what happened? So noisy. So he tweeted this. However, you know, Bilal Deng himself, he's not a new fashion guy. He used mobile phones instead of Twitter. So he didn't check the Twitter timeline. Like he was attacked to death. If he, let's think about this, if he used Twitter to check the timelines around his region, what could happen? People don't know that. It's something like WikiLeaks. You never know what could happen after some information shared out. It's opportunity change. So if we share ideas, I'm talking a negative case of this, maybe a very extreme case. But let's think about the opportunity when we share ideas. If we have some ideas, we keep it in the safe box. We never know the value of that. However, if you open it up to maybe in different ways, in different language, we can see what could happen from along this kind of sharing. It's a kind of a viral effect. We never know. Okay. These two guys want to talk more words between every way, and this guy is called Feng Zhenghu. He is also a legend figure in China. These two guys just met in every way studio after this guy was allowed to enter in China after 90 days of stuck in Tokyo airport because he was there protesting China government not allowing to enter. He holds Chinese passport by the China government, specifically Shanghai authority doesn't allow him to enter Shanghai for several times, but abduct him back to Tokyo because he is an activist. So the guy stayed in the airport like the movie terminal shown. He stayed there and demonstrate and the guy is a very traditional guy, so I called him. I called Mr. Feng, you can try a new tool called Twitter. He said, what? He didn't understand with that. I tell him that you can use mobile phone to send out a message that everyone knows what's happening to you in the airport. So he started to use the tool after 90 days of protesting, the China government allowed him to go back because so many people visit his tweet and send food, send clothes and trying to buy tickets to visit him, to talk to him, is kind of face losing to Chinese government. So that's why the government cannot stand this kind of movement anymore. Some single kinds of tweets. So these two guys, they together meet up finally and become friends. I call it open activism, it's an art combination with activism. We need these kind of creativities like people mentioned. We need creativity, we need amusement, we need jokes, whatever, to try to break the traditional media control and hierarchical control. This is very much interesting and matters. So that's the definition of terrorism coming. We, it's not the traditional sharing, we just try to push people to share but don't give them any benefit of understanding. I don't think that money incentives is the only way to encourage people to share them because many people sharing today, they're not simply caring about money return. So at least don't care about immediate money return. However, I argue that if you share more, if you keep your identity, you know, focusing and if you use different tools and channels like Mr. Fong, you know, he keep trying, trying updating his message, you know, all the time and eventually let all the world know him. As a kind of power, you know, he accumulates from his social sharing. So share is a kind of accumulation of capital. The more you share, the more you can accumulate this social capital. It's kind of something valuable and measurable. It's not the virtue thing. So the social network reconnect this kind of human nature because our human nature studied from sharing. Our society studied from sharing, sharing of fairs. No, not fairs. Sharing fair lightning skills and sharing foods to each other to become interactive and language emerged from sharing as well. It's the human nature, but we are losing that. Why? We need to think about this. So the theory of sharing is engaging with the boring methodologies and theories from the neuron technology, the neuron sense. I call it social neural network. For example, we, ourselves here and around the world, we don't need to think too much about ourselves so much important. But just think back to us, we are a single small neuron in the big brain. You know, every neuron has many synapses to others. We need this kind of synapses and we transfer the information to other neurons and eventually this kind of neural network can generate many information flows and circuits to help our ideas to be shared, to generate larger torrents, to amplify the ideas, to be more creative and generate solutions with this kind of circuits, you know, happen everywhere all the time. It's a social conscious happening. So we have this kind of pyramid thing from those every second sharing from like tools like Twitter, you know, we send from our mobile phones, devices, desktops every second around the world now. You know, there are 200 million tweets every day on Twitter. Nearly Twitter this website. And we have many blogs from this kind of torrents of information. People, those bloggers will still use, collect those information to make it into article and the journalist also making reports based on this kind of information. And then we have those more collective knowledge back to Wikipedia, et cetera, and into books. And then we got new theories and new consensus from the whole society. This is kind of a collective effectiveness. And we can have more collective intelligence even to a sense of sacred. You can perceive this sacred meaning by yourself anyway. So what's next? The Sherry Riesem book is writing and I want to see how Sherry Riesem could be applied to everyone's daily life. So we are trying to talk with many manufacturers like the mobile phone devices. How can we ensure the pictures, the taxes, the information on their devices can be easily shared to their social networks with a single click of a button, with a single click of a selection that we can see the message starting from here, like this conference room to the whole world. So that's my wish. And I think everyone can benefit from that. Thank you so much.
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Isaac Mao speaks about "How Sharism is unleashing liberty". The theory of sharism reflects on the share of information and ideas to the point of sharing action by using the case study of a decade of chinese social media and its impact to society, especially on social structure re-shaping, and individualization.
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10.5446/21400 (DOI)
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Good evening, everybody. Thank you for staying so late. I know it's already 6.30 here in Berlin and I'm happy to see many of you here. So I'm going to talk today about the future which we can already see basically by looking at the right places in the world. One of them actually being the Silicon Valley in the San Francisco Bay area, which you can see actually here on this picture with the Golden Gate Bridge in the background. So the features already here, it's just not equally distributed, was actually set by a Canadian American writer and I actually believe this is actually true. And by looking at the Silicon Valley, for example, where the digital lifestyle revolution has started and has taken over the world basically all of us, our lives and how we interact, how we communicate, how we socialize. And I want to give you a brief introduction about the Silicon Valley for those of you which haven't been there, which have not had the experience yet actually to either work there or be there at least for visiting, then to look at what kind of trends actually were born there and what actual trends are driving, especially ours now also from the mobility side for Daimler, former Sadie Spence and all actually other automotive OEMs. Now looking at the Silicon Valley, just a few topics here. This is a geographical region where the Silicon Valley is in the Bay area. If you haven't been there yet, I can just welcome you. I'm there now since three and a half years. I live in the Silicon Valley, work in Palo Alto, live in Redwood City basically between the airport and work about 20 minutes each way and it's just a wonderful place to work, to live and you will actually see why. One of the reasons being actually the weather. I mean, you might think it's funny actually to even mention the weather but it's actually true. If you look at the comparison here between Frankfurt and Palo Alto and the average basically over the year also for precipitation, it actually has an influence and there have been studies actually been done about this, been made about this, that it has an influence on the creativity, on basically how people live and work and act and of course with beautiful sceneries nearby with Carmel 17 mile strife, Monterrey, Napa and Sonoma Valley, Lake Tacho, it's all very close by. Actually the lifestyle being lived there in the area is also actually having a positive influence on people. Now looking actually at the people which live and work there, as you can see, IT employment, patents, venture capital, huge spikes in the Silicon Valley also compared basically to the rest of the world. Immigration has a big impact, the positive one actually as you can see here in the meantime more than 30% of startups basically being built up by immigrants and you have people like me, Germans basically living in the Silicon Valley working there, driving innovation and actually a lot is about innovation as you will see in the next few minutes. And what's also a driving factor and a success factor I would even say is the density and the close proximity actually of the companies, of the university, Stanford, Berkeley, of the whole basically environment with the legal and administrative support which you know startups need with the venture capital companies basically here on Sandhill Road, it's all very close by and our headquarters of Mercedes-Benz Research and Development North America which I'm heading is actually there in the heart of it all just a few minutes actually also from Facebook, from Apple, from Google, all the companies we are working with. Now looking at the digital revolution roots and digital lifestyle revolution as we call it being born actually in the Silicon Valley. So you can see a few essentials here on the one hand actually people are very much willing to take risks, it's actually okay to make mistakes or have actually failures also in the startup community as you all know they're probably only like one out of 100, maybe two out of 100 being very successful and you know having successes like Facebook, like Twitter and other companies you know being purchased by Facebook like recently happened for one billion dollars and that's one key aspect and the high value and it's very easy actually to grow a business there so if you're very creative, if you're open minded and you want to start something new maybe start your own business if you don't have it yet I can just invite you I mean the environment there is really very encouraging and it's a great place to be to live and to work and face to face networks actually play a very very important role even though with all the social networking and digital you know communication and so on still face to face communication and also this interaction of work and social and private actually drives trust and trust actually drives relationships also long-standing relationships and it actually helps innovation in the valley and how people actually work and invent and as you can see here in the meantime actually we do not produce any silicon anymore in the Silicon Valley we can still kept the name we are in the meantime actually in the fifth innovation wave as you can see so the Silicon Valley has something you know it has this ability basically to reinvent itself and we are talking here on the reinvent track about the right topic and as you can see basically starting from defense integrated circuit personal computer the internet and now the social and the mobile internet being the actual wave of innovation in the Silicon Valley actually the top websites as you can see here you know which are visited every day by all of us around the world are actually headquartered in the Silicon Valley or nearby San Francisco now talking about digital lifestyle trends started in the Silicon Valley just a few to name here out of this recent innovation wave always on simplexity innovation acceleration and social networking I will just go briefly and cover them so on the one hand always on basically it means on the one hand you know as we all know with our smartphones with our mobile devices you know we are always on we are always connected it actually has changed how we live how we interact and you know how streaming information basically is coming upon us and we need to filter much more information and it also creates some topics like urgency addiction you know we want to be you know basically always connected we already feel very strange you know if we are not online on the plane or you know in other areas where we have no service and so on so we just get used to this and as we can see even in the smartphone world you know OSS like iOS or like Android are the ones which are successful and others you know like Symbian and you know maybe even BlackBerry OS which have not managed basically to cover this trend even from the technology side wall have some issues. Next simplexity what this means is actually you know complexity underneath you know heavy technology underneath but then you look at it from a user perspective it's very simple it's very easy to use and I just wanted to basically you know show here two examples just by chance being Apple products the iPod and actually the very first iPhone from 2007 which really revolutionized the world in terms of you know phone what a phone means to us and being a smartphone and that you actually do not even see the difference between apps which are connected and apps which just you know use onboard data so this seamless integration and this easy to use and also aesthetic from a design perspective. Innovation acceleration being the next one so it's really all about innovation speed in the Silicon Valley so that's what's really driving you know the success of the companies and those companies you know which really are able to reinvent themselves continuously and are able actually to continually you know accelerate their innovation they are the ones which are really successful and also with new disruptive business models I mean if you look at Google also now with Larry Page having taken over again as a CEO you know he really manages the company as a giant startup company and focuses on the right topics. The next and last actually is the social networking so as you can see here basically you know global diverse networks, a while speed, bottom up empowerment, live casting you know very very you know big trends actually big changes and we have heard actually in some topics today you know what actually has been driven by social media and how it helps all of us actually today around the world. Next topic actually I want to go into a little deeper you know what does it mean for Mercedes Pans, why are we actually there and actually we have been the first company first automotive company having an office there we started our office back in 1995 and in the meantime we have been there basically since then have grown you know actually significantly we have in the meantime actually two offices since we grew out of the one location which we had and we have about 130 engineers, designers, you know software and hardware engineers working closely together and creating innovation for our cars of course and for the different brands like Mercedes Pans, AMG, Smart and so on and we also collaborating with other OEMs for example on topics like car to X and car to car communication creating standards for the future and it's not all about competition actually and it's also about collaboration. So one example actually my command which we have introduced to the world in 2008 it was actually born as a Skunkworks project and actually many of the innovations and even inventions from the Silicon Valley start like that. They start as a small Skunkworks project and it was this idea of actually building a whole infotainment system for the car completely built on the cloud, built completely on cloud content, cloud infrastructure, even the software basically you know running on this system is continuously updated each time you start it up and based on this actually you will see later on we have built the first product which we launched last year in 2011 just three years later. In 2010 we introduced Smart Drive which is actually the first true automotive app on a smartphone. It was on an iPhone. We introduced this for smart you know with a cradle and you were able actually to have a complete infotainment solution on a smartphone and touch the screen actually the multi-touch screen of the device with media, phone, navigation and assist and you can try it out for free from the iOS store for some time and then of course because of navigation and so on there is some fee to be paid if you want to continue to use all the features. In 2011 we introduced AMG performance media and those of you which might happen to drive an SLS AMG you can actually get this. And it's an Android based system. It's actually the first Android based automotive solution by an automotive OEM especially a premium OEM and we have been not just the first actually to integrate Android as an operating system for an infotainment solution and also performance you know solution with different performance apps actually to support you know your racing and G meter and other features but actually fully connected to support Google Maps in the car and this is also driven from the Silicon Valley actually by cooperating closely with companies like Google. We have announced a strategic partnership actually with Google in January of this year working closely with them actually to bring their innovation into our cars where it makes sense. Also Internet radio like OPO here from Berlin as you all know and other apps and we offer actually an open platform an SDK we call it drive mode and actually any Android developer who has an app you know running an Android which makes sense to be used while driving could basically change their app to make it workable even in the car while driving on this Android platform. Very innovative and I am sure this would not have been possible you know within Daimler within basically the company without this office there in the Silicon Valley you know being there at the pulse of this innovation and also working closely with the companies nearby. Next is Command Online and our Mercedes-Benz apps which we introduced last year in March first with Google local search was sending routes and sending POIs to the car and also weather we have added Facebook, Google Street View and Panoramio in November. We are just adding now actually Google news, Morningstar Finance for stocks and so on and parking finder and we are just launching actually in the next few days our Mercedes-Benz apps shop so that customers actually can download their apps or purchase additional apps which are not for free or not included with this and this was actually the product which we built based on this original idea of my command in 2008. One other example, digital drive style app which we just announced actually in debut at the Geneva Auto Show and this is actually a completely new approach kind of built on the smart drive idea I showed before to use actually the smartphone as an engine in the car for the infotainment solution in the car and here we go a step further we use the iPhone as an engine to actually drive the screen in the car and being completely remotely controllable from the rotary knob and the keys and so on around this in the car and also with this actually and having this approach of driving the screen from the smartphone actually through a digital video interface, HDMI we are able to bring in completely new user interface structures also a very rich UI as you can see here we invested a lot actually in the UI in terms of having these glossy tiles and having mirroring on this glossy surface and a new approach in the UI, menu structure with media, social and places of course with Facebook, Twitter and so on and navigation integrated but with a lot of connected apps and media also getting your media out of your social streams and so on very rich feature set and just a few more examples here like these glass tiles when doing an alphabetical search so not just innovation on a macro level but also innovation on a very micro level when it comes to user interface design, user interface technologies and there's a lot of actually design and engineering work being actually put into the development and the design of these technologies and basically for the customer at the end of the day it just needs to be delightful, easy to use and just a joy basically to use the system and many of the little details we focus on are not necessarily seen right away on the first glance. Now the last topic I wanted to present here today is this DICE, dynamic and intuitive control experience we showed at the consumer electronics show in 2012 actually in January in Las Vegas and just to give you a few examples on the one hand we included actually gesture control in the interior of a car so basically complete experience without buttons, without hard keys, without switches you can just use your hand and actually you don't have to use certain gestures to actually control the system. It's like a touch screen without touching the screen actually and we used the whole front windshield for augmented reality which I will show on the next page here. As you can see with a rich 4K display basically integrated in the windshield and this will be possible in a few years from now and with all the rich data from the cloud, with all this information basically from the information space around you there's like tons of layers of information actually which we could digitally use and overlay in a professional manner where it makes sense as you can see here with a few examples and thinking about 2020 and down the road you think about also autonomous driving and even more usability of augmented reality or features like this being possible without having the driver's distraction being an issue. And then this approach of social media and places we introduced it in this DICE prototype and new interior and then actually continue to use it in the product, in the digital drive style product which we will launch actually in the new A-Class later this year and also with like a swarm intelligence and connecting basically your social data with an intelligent map underneath and with many, many ideas actually to just create a new rich experience while driving and well integrated and of course very easy to use and here a short clip actually. So for those of you which have been at the Consumer Electronics Show in Las Vegas this year I hope you had a chance to stop by our booth and actually experience it. So very, very intuitive to use so basically just reaching with your hands towards these you know virtual soft keys and buttons and grabbing things and pulling them down actually from the exterior from you know the surroundings and interacting with that data very easily you can see actually for those cars around you which share that information can immediately identify them and you know add them to your address book or follow them on Twitter when you know driving by an interesting restaurant or you know listening into the music of a pub you know what you like just by driving by or you know connecting maybe songs you like with certain location you know you know things like geocaching of course you know you know you want to share their routes with you and of course car sharing as the car to go cars you see around the show here. And let me just finish with one slide here and some information about things we are working on now and where we go next actually beyond what I have presented before is you know we are really thinking about a new you know generation of vehicles which are truly intelligent and truly you know digital companions which learn your habits which adapt to your choices predict your moves and interact with your social networks and really create an experience you know which goes beyond what we all you know know today and experience today. So I hope you have some questions or some comments we have a small Q&A session and thank you very much for listening. Thank you. Just let me know when you are in the Silicon Valley you can stop by our office. Hi I have a question. In the past it always used to be that the car world and the electronics world was hard to synchronize. I mean we used to use and have a new iPhone every year we buy a new car three years seven years something like that. And another point is if the iPhone sometimes crashes and does not what we want then that's okay maybe not nice but okay whereas a car we expect that it works really every time. So how do you synchronize those things? Yeah it's a very good question actually. So we have two things on the flexibility side to actually be always up to date and you know to keep pace basically with the technology and with innovation and so on and to kind of you know couple and have a solution you know for the slow five six year development cycle of a car and you know the six to twelve month development cycle of these consumer electronics and apps and so on. For that to solve that and bridge that gap actually we created two solutions. On the one hand basically Mercedes-Benz apps for example you know running in the browser environment having this flexible approach and having the fully embedded systems basically which are fully proved and run through the three to five year development cycle you know be open for you know apps which you can continuously download update upgrade and so on and add down the road without having to visit the dealership. That's the one solution you know creating these fully embedded systems being flexible and being open for these add-ons and new installations of apps and so on. On the other hand we create you know as perfect integrations as we can of smartphones and actually new solutions which are based on the smartphone and to enable this way customers actually to bring in the latest technology and latest gadgets each year basically as they come out and use it in the car and of course you know in terms of stability we put a lot of focus and a lot of automated and manual testing and so on to make sure that these embedded systems you know work rock solid you know as you're used to today of course you know when you make or when you develop systems based on smartphones there could be cases you know just basically based on you know the nature of smartphones that you know you cannot completely rely on you know compared to fully embedded systems that is clear. Hi thanks again for the great speech just one question you said that for the new A-Class you're going to ingrate the swarm intelligence technology how soon do you think you're going to include the technology over all models? Yeah so this digital drive style concept actually which I presented with social media and places in this rich UI we will introduce it first in the A-Class but actually it is planned to go across all or most of the model lines I should say so we do a staggered lounge basically then in the B and C and E-Class and other vehicles as well so it is planned as a cross-carline solution and by the way if you haven't visited the Daimler booth with in-depth evasion to hause it as a theme you know please feel free to stop by check it out it's cool. I am a bit disappointed by your talk if you work in the Silicon Valley and you present products as disruptive say as the iPhone or the iPod products that have completely made other products useless and have obsolete and have defined new ways of living I can't see that in your products like if I put my iPhone in a car I can do the same things without that your dice does without gloss and if I if I ride by or if I drive by in a closed vehicle if I drive by a bar which plays music in a closed vehicle and I can hear the music from the bar in my vehicle it seems a bit over the top because if I walked I could hear the music from the open door so this seems like it's an awful lot of actually it doesn't seem like that much of an effort to put like those electronic gadgets into a car that we know from a hundred years so I would like to if I the the lie I thought there was this is something from the lifestyle that I don't need in Europe I think so if I have this this car and I can't find a parking lot when I when I hear that lovely music from the from the the bar it makes no sense so I I hope to to hear a few moving ideas that maybe went away from the pure box in which I sit and have to steer but I'm sure you have ideas maybe you could tell some of these it's a it's a great great comment and I mean that's one of the reasons actually why we are here too you know it's it's overall about mobility so cars you know it's one form of ability and you know everybody can choose do you want the car or not you know do you want a small car a large car a convertible or you know a coupe or whatever and in that regards I mean we created solutions like car to go as one mobility concept you know as car sharing we're working on other new mobility concepts so in general I think as a company and also you know for me in the Silicon Valley with our team there you know we fully support you know to come up with very disruptive and and new ideas for mobility and then also for you know the car as long as it's with us as long as it's there and we all like it or some of us at least you know to create solutions like my opinion if you look at the dice and and you know maybe it was just a very short clip and you know we didn't talk to you know deeply about you know all of its in my opinion pretty disruptive you know innovation and ideas with augmented reality with gesture control you know with with you know the intelligence you know I talked about last as last point point you know with having you know basically context aware technologies you know with bringing in you know more personalized and and more adaptive you know user interfaces that basically the car or whatever you have in terms you know of your devices is already a step ahead of you you know and can give you the right recommendations and make even predictions of you know what's maybe your next move maybe based on calendar data based on lots of data you know and based on your habits and and what you're used to so my opinion there are actually a lot of you know big innovations and and inventions in this area coming up but there are a lot of small improvements too you know which my opinion will make our life just much easier I mean if you look at the car itself how many things you do not have to operate anymore you know like your vipers going on when it's raining you know your light is going on when you go into a tunnel you know with the Stronik plus and our cars you know the car is breaking for you it's accelerating for you it's doing many many things I mean the next step will of course be and it's going to be a giant step is autonomous driving you know and there will be scenarios first where it's much easier maybe on a highway and so on with all cars driving in one direction and so on before we do autonomous driving in in in a city or so where it's much more complex with intersections with you know people crossing the streets and so on but in my opinion there's still a lot of innovation and inventions actually awaiting out there either to be discovered or we are already working on and you know partially maybe not openly talking about it yet so when there are no more questions I would say thank you JJ again a big applause for you thank you
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- Discover the future in the Silicon Valley as innovation driver and digital trend setter - The Digital Lifestyle Revolution re:invents everything - how we live, think, connect, drive. - How Digital Lifestyle is evolving into a "Digital DriveStyle" - What does that mean for our Mobility future? A talk presented in cooperation with Daimler
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10.5446/21403 (DOI)
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Hi everyone, thank you for being here. I'm Jeremy Zimemann, I'm the co-founder and spokesperson of Lacroix-Draitur-Junette, we're a citizen organization defending fundamental freedoms online, you may know about our work. We are building a kind of citizen toolbox to help everyone understand what is going on when our freedoms online are attacked and tools to help everybody participate in the debate. We've been mostly busy in the last three years kicking Acta's ass, you may have heard of it, but the job is not done yet and this is partly what I'm going to tell you tonight. I come here with kind of bad news, then kind of good news and a little bit of a plan. The bad news is that there's a war going on, you may be aware of that, this war is the war against sharing. Those copyright industries have been waging it for the last 15 years, they've been trying to push all the representative measures you've heard about from the DMCA in the US to the EU CD and the IPRED in the EU and various national transposition of all of this. It's all clear to all of you, you've seen the strategy from suing the individuals to trying to automatize the suing, corrupting governments to install some administrative authorities that would bypass the judicial like the French case. Well, this is so over, this is so prehistory. The strategy right now is to push enforcement at the very heart of the network. How many among you have read at least one version of Acta? The final one. That's much more than the average, I may be more or less familiar with this principle that Acta pushes for a cooperation, when I'm using the air quote it means I'm quoting bits of it. It's pushing for cooperative efforts between the ISPs, the service providers, the YouTube, the Emotions, the Facebooks of this world, but as well the access providers, the Vodafone, the Orange, Deutsche Leicombe and so on and so on. A collaboration between those ISPs on one hand and the copyright industry on the other hand. The point of that collaboration is to impose measures or remedies to deter further infringement. So it sounds quite harmless when you look at it, but when you think about it with a technical mind, measures to deter further infringement can only amount in technical terms to automated blocking of content, blocking of access to content, filtering of communication and discrimination between those communications or automated removal of content. All of which you would recognize amount to the very equivalent with the kind of censorship that is being done for political purposes in some not so friendly and not so democratic countries. The bad news is that by pushing enforcement at the very heart of the network, we may be about to make a step that will be impossible to go backwards. By programming machines at the heart of the network to decide what has to go through and what cannot go through, we will pave the way to the generalization of the deployment of the very same machines that are used on one hand by the dictators to censor content and spy on their populations and on the other hand on telecoms operators to restrict their users' communications in the name of creating new business models by hurting net neutrality. Once we've done that for copyright, there's no way we go backwards. So the bad news is that this war against sharing is taking a turn as of today that may be very much decisive for the future of the internet as we know it. What is at stake here is the very architecture of a free, open, decentralized and universal internet. The internet we love and care about is what it is because of this architecture. Architecture matters. And the very characteristics of this architecture is that the internet we love and share is decentralized. It is universal. This universality means that everyone accessing a free internet has access to the very same content, service and applications, but also has the ability to publish some. You know that this is how you invent stuff. This is how you experiment. This is how you deploy something. This is how you create startups. This is how you invent. This is how you remix. This is how you mash up. This is how we share. It is because of the very universality of this architecture that we call the internet, that we're about to maybe change our societies, that we're about maybe to change ourselves and become better persons if it remains that way. Well, by its universality, a free internet is what economists would call a common good. It is universal. Therefore, we all share it. We all own it. It would be a mistake to acknowledge that the people running the wires are the people who run the internet, who own the internet, sorry, that the people who run the routers are the people who own the internet, that the people who manufacture those terminals that enslave you into proprietary software, hell, and close chips are the ones who own the internet. No. The internet as the aggregate of our intelligences is a common good. We all own it. We all have our share in it, even if we're using Facebook or whatever, rather centralized bullshit there is out there. And as a common good, we commonly own it, which means that we have a responsibility over it. We have a responsibility to deliver to the next generation the very same tool we had between our hands to become better persons and to change our society. This is one of the greatest responsibilities we've had. This is probably one of the most important challenges our generations have to face. And you know probably as well as I do that if we do not manage to maintain this universal architecture as it is, all the other global issues that are at stake, whether they're environment, finance, energy, or whatever, will be so much more difficult to solve in a way that would represent us, that would represent the general interest. But you probably all know that already because you're here in Republica, right? So that was the sad news. The good news is that there is something we can do about it. And that we have evidence of that. You've all witnessed the sopa and pipa fight in the US. Some of all may actually believe that this was a fight in the US. But most of us know that it wasn't. It's not the US citizens alone who kicked sopa and pipa out of the Senate and the Congress. It's the whole Internet. It is us. It is every one of us. I mean, we turned the website, we blacked out a website for sopa and pipa because we thought it was mostly the same thing as ACTA. But I guess that many of you did the same. Many of you blogged about sopa and pipa in your own language, retweeted, retweeted. We were all part of it. The Internet, the universal and free Internet kicked sopa and pipa's ass. And that's something. And that's evidence for everyone who will tell you, oh, there's nothing we can do about that. It's over. We cannot fight it. And so now it's wrong. And look at ACTA. Who here didn't never heard about ACTA? Who have never heard about ACTA? Nobody. Nobody. One year ago, the answer would have been the total opposite. We've been working and when I say, it's not only the quadrature of the net, many people around here, once again, all of us, we worked for that. The whole Internet went on fire when the European executive, with all its arrogance, signed this thing a very few days after the seizure of mega-upload by the FBI. The whole Internet turned on fire. It's not only the EU. And once again, we achieved something incredible. We literally turned the European Parliament over. Well, we may be about to do so. And that's one of the, maybe the sad part in the good news is that we may be about to win about ACTA in the European Parliament, but it's not won yet. And if at one single stage we lower our guard, then we may lose it. So let's not be overconfident about it. But right now, as of today in the European Parliament, you can feel the delicate smell, the delicate scent of victory in the air because so many more people understand the importance of ACTA, the importance of these issues for the future of our societies, for the future of the free Internet, and for the future of copyright. So we achieved something tremendous and we have to confirm that. We have to win this ACTA battle in the European Parliament, period. And we know how to do this. We know how to do this because we've been doing that for some times. We have to be there at each and every step, all the boring steps in the procedure of the European Parliament. And we may have an occasion to talk about it in the Q&A or later with some drinks. Five committees working on a report, the report being presented in plenary a yes or no vote. The vote will be around the summer. You'll hear about it again soon. We have to be present and active and not lower our guard at each and every step. And we must win this ACTA battle in the European Parliament. But even more importantly than that, we have to keep the eyes on the price. If ACTA is just pushed away and nobody cares, well, this may not happen. Then an ACTA 2 will come back. An ACTA 2 may start being negotiated. The day ACTA is kicked into the European Parliament. And an ACTA 3 and an ACTA 4 and I have prayed 12 may come one after another as they stacked up for the last 15 years. With the tremendous momentum we are achieving at the moment, we have a responsibility to do something more about it. I think that it is time that we literally put an end to this absurd and dangerous war against sharing. They are feeding us with lies. They are feeding the elected representatives with lies. They are telling that whenever one of these industries loses some money, it is because of the culture enthusiasts who share digital files between them with no intent of profit. And we all know this is wrong. I mean, the French ad-op, the Three Strikes Authority, demonstrated in its own study that people who do the more file sharing are people who spend the more for culture. So many independent academic studies prove the same. All of us here do file sharing maybe since Napster existed. And all of us know that the more you get access to culture, the more cultivated you get, the more culture matters to you, the more you will go to concerts, to theater, to movies, the more you will buy books. It is exactly the same thing as the people going in the libraries, borrowing the more books in the libraries being the people who buy the more books. We all know that, right? Well, then we must turn that into public policy. So those industries stop attacking the very essence, the very fabric, the very architecture of what makes our free Internet so great. And there is a very simple solution for that. It's called the limitations and exceptions to copyright. It's called fair use. This is the bit of the law where the author doesn't have his or her word. This is part of copyright. These are parts that are excluded from copyright. These are parts that are of general interest. When you want to show a movie to a classroom, you do not have to ask for permission because education is of higher social value than copyright. When you lend a book to a friend, you don't ask for permission because lending and friends and sharing is more important than copyright. And it couldn't be enforced anyway. When you create a parody of the work, you don't have to ask for permission. You just do it because a parody is essential for freedom of speech, which is essential for democratic participation that is indeed more important than copyright. Well, sharing of culture is just the same. And we have to shout it loud and clear. We have to make evident. And we have to stand for it. We have to turn the sharing of files between individuals and not for profit into an exception to copyright. And then we will ultimately shut the mouth of those industries who will go counter to our fundamental freedoms online and counter to the most precious tool we have between our hands for improving the world we live in. So that's the plan. And now you ask me, how do we get there? You ask me. Thank you. The answer is partly I don't know. And partly I got a bit of a clue. There is this 2001 slash 29 directive in the EU. It was supposed to harmonize copyright, but didn't harmonize anything. It is a failure on all regard. And the two studies that landed on the commission's desk said the same. So as the commissioner, the French commissioner, Michel Barnier, is announcing that he will maybe and it will get more complicated if we kick actors out, revise this IPRED, the enforcement directive. We must be louder than him in asking that the EU city, the 2001 slash 29, be reopened and that exceptions be renegotiated and that all rights as the public and that all right to share culture be integrated and made into the EU law. I have the impression that this is something we can achieve. And how do we do that? Well, first of all, we look at what we did. We look at what we did with SOPA, PIPA and ACTA and we ask ourselves how to do it better. What we did was to use every single node of the decentralized internet for what it was or for what it wasn't, for what we hadn't think it was, is to use every single word we had in our minds to make it loud and clear that those things had to be kicked out is to use every single pixel that we found available online and turn it into something else that was conveying a message. It's to go and talk to every possible community from the development people for access to medication in Africa to the AIDS patients and gay rights people to the farmers sharing seeds to some artists to the standard human rights organizations to journalists to outreach everywhere and we have to convey this message. This is our responsibility to care about this free internet and to protect it from those interests that want to turn it into some television 5.0. We have to do it because we understand what it is about. We have to do it because as we understand what it is about and as this is a common good that we own and share collectively and as this is a battle that we have an occasion to win, well we just cannot afford to lose that one. Thank you very much. And this is where I hope there will be comments, trolls and questions. I see a hand here. Oh, maybe it's simple if you come and line in the middle. Hi Jeremy. I've seen you giving these talks like 2009, 2010, 2011 and now and you always pretend we all can do something but actually all it took was Wikipedia going down for a day. So I think it's not about all of us, it's about the big players. I'm sorry I have to disagree with that. I know a bit how it is to deal with the people from the Wikimedia Foundation. There are very heavy structures now, they have a lot of inertia, they're consensus based and it's very difficult to make them take positions and move. If Wikimedia, if Wikipedia moved, it's because so many others moved before. It's like the Dominos and it's literally a domino effect going in each and every possible direction. I heard this story, I don't know if I can say that publicly, of some venture capitalists investing in many startups in the Silicon Valley that got convinced himself and made phone calls to the people who was funding saying come on, this is your shit, this is your business that is at stake, do something about it and participate in this. So we cannot imagine the range of organizations and individuals who participated in that. From the ones we know very well, the EFFs, the public knowledge, the coalition for the future that just emerged out of this, to the ones we don't know, to all the individuals who took their guitars and played this, the day the Lolcats died, videos and things like that, that's the sum of all of this. Seriously, one in something million phone calls to the CNAH, you think it would be only Wikipedia? Hey, this is me again. Thank you for this great presentation. I want to talk a little bit about something different. What you're mentioning is actually a conflict in culture. I see it as a conflict in culture. We have this conflict going on that the Internet is seen as a commercial tool by most of the people who make the decisions who are put in place by us. And for us, it's actually culture. So one thing I see really necessary is that we try to give explicit declaration of this culture and try to persuade and push our utopias of what the Internet is and what it is all about into public consciousness. So it's not only about killing Akta right now. Of course, it's the first thing we have to do. But later on, I think we should all think about how can we dissipate this idea of culture we have? How can we dissipate this idea of culture as broad and as wide as possible? Your Internet is showing. Well, yeah, I fully agree with that. And I think that there is no better way of achieving this than by using the Internet for what it is. I mean, the Internet is not Facebook. It's not Google. It's not Apple, right? The Internet is these thousands of blogs, is those thousands of IRC channels, is those thousands of memes and images, whichever medium is conveying them that are going dozens of times around the world. All this we create when we work towards the common objective such as killing Soapar, Pipa and Akta is really teaching the world about the Internet and about what the Internet is about. And I agree with you. And I hope I made it clear enough. Kicking Akta's ass in the European Parliament is a crucial victory because it will be of global scale. Because beyond the question of copyright, Kicking Akta would avoid that we create an Akta precedent when some governments could just gather around the table and decide that those international institutions do not really go the way they would like them to go, that those parliaments are too complicated to deal with, and just decide repressive policies together. So it is also important for that that we kick Akta. But in the end, the objective is to change society as a whole. That people who just use Facebook because they don't know what the Internet is about come to realize that Facebook is the modern equivalent of a TV that just collects all your life. That when Orwell wrote about Big Brother, he didn't invent something going as far into our privacy as Facebook. Everyone has to understand that. But I want to tell you this anecdote. Is that on a previous copyright fight we had in France, the Datsy Lo, the EUCD transposition, in 2005 and 2006, the rapporteur was a guy called Christian Vanest, who is on the right of the right of the right wing party, who is really, well, he was the first to acknowledge guilty of the new homophobia, not crime, but misdemeanor or whatever is under a crime in France. He's really a nasty guy. And I would never think I would hear something like that from this guy. When the Adopi debate began some years ago, he said publicly, well, you know, when I was working on the Datsy, I understood that something was happening. And I understood that from the fuyi creative, the creative chaos. I knew that something was happening. This guy was the most conservative, almost fascist people ever. And he was praising chaos as something that made him understand the real cultural diversity, the real social diversity, what the internet was really about. So I think that it is when we fight for it that we really demonstrate what the internet is all about. And if there are people around here from the Arab countries who recently uprooted, I think they won't deny that. See, there are more questions. There must be. What, no time for more questions? Oh, please, just one. Okay. So no more questions. Let's finish the discussion around drinks. Thank you very much.
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Toolbox And Strategies For Winning The "War On Sharing" In The EU: Decentralized citizen movements helped raise massive awareness on legislative and political processes such as SOPA/PIPA in the US, or ACTA on a global scale. How can citizens face these multiple attacks against our freedom online by proposing an alternative to repressive policies? How can we collectively put an end to the "war on sharing" waged against entertainment industries' best clients, in order to foster a vivid digital culture online while protecting a free, open and neutral Internet, and the lulz?
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10.5446/21404 (DOI)
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Hi. So can you all hear me well? And can you all see me well? Because I'm going to have to hang here near the computer because I have a Prezi that, so I don't have the possibility to use this little machine that other speakers use and, you know, walk, which is pretty cool to be able to walk and do this, but I'm going to have to be hiding behind my computer somehow. I hope this is okay with you guys. Let me know if you want me to move or if you can't see me well. So this is the title of my presentation. It's Syria, citizen empowerment against brutality. Here's all my information in case you want to contact me. I'm particularly active on Twitter at leila underscore NA, if you want to contact me, or through my Global Voices online profile, or through my regular blog, Leila Nashawati, or through my email, leilaNashawati at gmail.com. I'll share this again at the end of my presentation, and please, I mean, feel free to contact me throughout the conference or as soon as we are done if you come up with any questions regarding what we saw here. So I chose this title because we have already seen the degree of brutality, the Syrian institutions, the Syrian authorities are displaying against their people, and this is quite unprecedented, even within an area of the world where we have seen a lot of violence from the institutions, a lot of violence from the power structures. But even within this area, the case of Syria is particularly unprecedented, the degree they have reached in repressing citizen forms of expression. However, citizen narrative, citizen forms of expression keep emerging in very amazing ways, considering the very difficult dramatic context we are living in. So for years, we never heard anything about Syria in particular. For years, the government, the Syrian regime, allied with a wall of silence to isolate its citizens from one another and also to isolate the country from the world, so that I get asked a lot, so how come we never heard of the Syrian regime, and we never knew it was this brutal? Well, because there was a wall of silence around the country, and now this wall is broken, and I don't think there's a way back to the way things were, no matter how much. The government tries to repress citizen narrative, citizen forms of expression continue to emerge in unexpected, extremely creative ways. This silence, Syrians are very aware of. So this is a photo of citizens of a place in Syria called Kafar Nubil that has proved to be extremely creative in the messages they're sharing with the world in very rudimentary ways, we could say, very traditional ways, very extremely innovative. So every week we have a different message from the city of Kafar Nubil, which has suffered a lot of government repression in Syria. So this is a group of people from Kafar Nubil, this is a white banner, and they just wrote Kafar Nubil occupied, the occupied city of Kafar Nubil, Syria, the occupied town of Kafar Nubil. They're under occupation, and they're holding a white paper, and they're wearing gags to show the world how the silence, the silence of the world, and the silence within Syria has been what makes the isolation of Syrians possible, is what makes the government's actions even more ruthless, because there's always been this wall of silence against Syrians. This is a very powerful message telling the world how the silence affects Syrians in an extremely dramatic way. This is a video that also goes on the importance of silence and how it's been instrumentalized by the government, and this is a message from young activists to the silent majority, to the people who still are afraid in Syria to speak against the government. So this is a young Syrian telling another young Syrian, we need your voice. If we don't have your voice, we are lost. So at the end of this video, this young boy says your silence is their most powerful weapon. So I want you to take a look, and I found it with German subtitles. Do we have the sound okay? I'm afraid, I'm afraid of you. I'm afraid, if Hamza and Hajar are the children they're afraid of, you'll be afraid. I'm afraid, I'm afraid, I'm afraid, I'm afraid, I'm afraid, after 100 years of kunivez this young Syrian mother of mine will either be killed or returned to Syria or The criminal system? Let them change. What are we afraid of? Of murder? Of death? Of not fear? What are we afraid of? Of crime? Of their truth? Who are we afraid of? Why do we need to change? What are we afraid of? Of the sectarian? Of the sectarian? Of the sectarian? Of the sectarian? What are we afraid of? Of the sectarian? Of the sectarian? What are we afraid of? Of the sectarian? Of the sectarian? Who are we afraid of? Many of the sectarian youths are laughing at their lives. They don't want to accept you as a better person. We have a chance to change our future. What are we afraid of? Of you and the listeners. What are we afraid of? Of not fear? Do you want your family to live like you? Do you want to keep paying for your life? Do you want to keep going? Do you want to renew your faith and not fear? Do you want to stay the last of the world? What are we afraid of? There is nothing to be afraid of. Are you afraid of the best? You are also afraid of those who don't have families? What are we afraid of? Of the belief? Of the honor you gave me? What are we afraid of? After everything that has happened, are you afraid of? What are we afraid of? After 15 years of being in the desert, there is no fear. What are we afraid of? Are you afraid of death, martyrdom, and the destruction of your country? What are we afraid of? Of the people of the dead. I am not afraid of you, I am not afraid of you. You are afraid of me. I am not afraid of you. Did you like this video? So it's an example of a very powerful message shared in a very creative way. This has gone very viral through social media. So the regime has not stayed, of course, passive at these new forms of citizen expression. Facebook or Twitter or YouTube are not what's at stake, are not the enemy for repressive regimes. Freedom of expression is the enemy for these regimes. So any space where citizens find new room for expression, new room for communication, new room for organizing, that's going to be where regimes are going to be focusing their efforts, trying to repress citizen organization and communication within these new channels. So now we see how the government is trying to silence protesters, activists in every possible way, in every space where forms of expression are organized. So the Syrian regime has been brutally silencing protesters. This is an icon of the Syrian revolution. He's called Giyath Matar. He was very well known for handing flowers and water to soldiers in the neighborhood of Darayya in Damascus. So he became somehow a leader of the nonviolent resistance in Syria. So that's what the government is most afraid of. The government is afraid of nonviolent talk, nonviolent resistance, because that's what they cannot fight. They cannot produce any response that is not violent to any form of peaceful expression. So they go against these forms of expression of nonviolence and peaceful resistance in extremely violent ways. So this is Giyath Matar. He was killed. They kidnapped him and they returned his body to his family a couple days later. So there are silencing protesters in the streets. They're silencing all forms of citizen expression. They're silencing humor. This is a cartoon by Ali Fersat, a very well-known cartoonist from Syria. So this is a cartoon that shows Bashar al-Assad asking Gaddafi for a ride to whatever Gaddafi is going. This is a few months ago before Gaddafi got killed. So when he published this pic, this photo, this cartoon, a few days later he was kidnapped and he was brutally beaten and they broke both of his hands. So they kill protesters. They use very metaphorical ways to silence all forms of opposition with cartoonists, with people who write, with people who draw. It is very common that they break their hands as a metaphor of silencing their forms of production. They also silence music because music is a very powerful element of expression and resistance in the Arab world. If you see a very dramatic situation, people gathering, they still sing, they still dance. So this is a demonstration in Hamma. People singing this song called, come on, leave Bashar. We want you out. So it's a folklore song with very catchy beat, with very ironic lyrics. Like they say things like, freedom is knocking on the door and you Bashar cannot hear it, please go leave us alone. So this has been so viral that in every demonstration, in every country, in solidarity with the Syrian people, like I'm in Spain, we have a lot of demonstrations at the Syrian Embassy in Madrid. We sing this song and this song was popularized by singer Ibrahim Kashouz from Hamma. So this is Ibrahim Kashouz a few days after the huge demonstration in Hamma. They also kidnapped him and they cut his throat and ripped his vocal cords off. I'm sorry if this is disturbing for some of you, but this is Syria today. This is what happens to a singer, not even a member of the political opposition. This is a singer who is singing in the demonstrations. So they ripped his vocal cords off. But if you can see here, everybody now at demonstrations are there. You find more hands holding mobile phones than people almost. So this song has gone so viral that even if they killed Ibrahim Kashouz, may he rest in peace, they cannot stop his voice. They cannot stop the voice of the Syrian people. They keep trying to silence bloggers and journalists. Blogs have become a very powerful tool in the land of state-controlled narrative. So this is a friend of us called Razaan Razawi. She works for the Center of Media and Freedom of Expression in Syria. So her and all of her colleagues have been arrested and they're going to go through trial for accusations of betraying their country. And of course their only crime is to write to demand freedom of expression for their country. So everyone who demands free speech is a target in Syria at this point. So of course they're trying to silence protesters in very brutal ways. But at the same time they continue trying to fabricate their own narrative, their own state-controlled narrative. They've been doing that for decades through their official state TV, state channels like Sanaa and Dunia. They have done that for decades to create their own reality through their own controlled media. But now with all the contents we have floating the Internet, less and less people rely on state-controlled media. And more people have access to different forms of expression of what's happening. So just to give you a hint of how fabricated most of the videos and most of the contents by these state-controlled channels are, I'm going to show you a couple mistakes that these channels make. And they're making more and more mistakes because they're more and more desperate. So they do things very fast, they try to question activists' narratives so fast, sometimes in such a clumsy way that crazy things like the ones you're going to see, the ones I'm going to show you happen. So I want you to pay attention to this video. This video by state TV Dunia, is it Dunia? I don't know if it's Dunia or... yeah, Dunia. They show, allegedly, a crime committed by what they call terrorists. So we don't know if it's activists, we don't know if they actually committed this crime. We don't know exactly what the information is because Syrian state TV is very unreliable. But what we know is that we see a hand of a reporter, a journalist's hand, touching the stuff at the crime scene. So we all know when we work as journalists, you're not supposed to touch anything that's on the ground. And you can see how before the camera gets there, the journalist from the state TV is organizing stuff on the floor so that it looks good for the camera. And the presenter who speaks, shuts down in complete shock, like they caught us. They saw that we are fabricating and manipulating the scene. So look at how she stays quiet and she doesn't know what to say for the rest of the video. When she says, when she sees this reporter manipulating the proof, the evidence of the so-called crime by terrorists in Damascus. She stops talking. That shows they say victims of a terrorist attack by armed groups. And you can see two men comforting each other, maybe after losing a relative or maybe after being wounded themselves, like really caressing each other and hugging. But someone tells them, okay, you can go. We're done with recording. So they're like, okay, let's go. Okay? Like actors. So let's see. Pay attention to this detail. Okay, want to see this again? So they're there posing for the photograph and then someone tells them, okay, we're done. You can go. You don't have to be posing for this video anymore. Okay? Well, this is very common with Syrian state TV, but now we see how things really are in the country. We didn't used to see it before. So in spite of the attempts, more and more clumsy attempts by the government to control, to stop and silence activists and to fabricate their own narrative, their own state control narrative, citizen narrative at this point is unstoppable. I'm going to show you a couple examples of very creative things. This is a demonstration with this big poster that people are holding. It says oppression, corruption, despotism, demolition. This is the Syria of the current regime. So we're going to see what they do in the middle of the demonstration. I don't know why so much people can avoid these things and vulnerable people would be happy with it. The words of our society that is developed and sensible. They are three-series. So this is now, this was like last week. After all they've been through, see what they're doing, see what they're still doing out in the streets, they're taking to the streets, they're flirting the streets with these kind of very creative messages. They're also flirting the Internet, especially a lot of people living out of the country, are using Facebook and Twitter and other tools to stay updated on what's happening in the country. So I don't know, maybe we need to make this bigger. Let's see if I can make it bigger. I guess I can show you this, I can share this presentation with you guys on Twitter, but this is a list of the hashtags, of the tags, the keywords that people are using on Twitter that have become trending topic. So they're words decided by the Syrian community to bring attention to specific events related to demonstrations in Syria. So different words that have attracted worldwide attention through activism using these channels, these social media. So we have... Don't Trust Assad is one of them, one against the referendum. Bringing attention, maintaining attention to the Syrian struggle is vital so that the world does not forget about what's happening in Syria in a context of a lot of things happening worldwide. This is a very good example of activism that combines online with offline initiatives. So this is a photo created by a group called, by a community of Syrians, mostly abroad, but they work a lot with people inside of Syria. It's called, the Syrian people know their way, the Syrian people know where they're going. So they take inspiration in other peaceful demonstrations and nonviolent resistance from other parts of the world. Here they say, Chile, so defend yourself like Chileans do. So I'm going to show you their gallery. Okay, this is their photo gallery. They have very creative examples. So defend yourself like Chileans do. Let's see this other one. Yeah, like Chileans do. Let's see if they have more. This is all from Chile, but they have others where they say, defend yourself like Palestinians do. And different examples of forms of resistance where they take inspiration. So they take global inspiration from other mobilizations. These are other very creative art pieces that they have done. So they defend yourself like Tunisians did. Defend yourself like Egyptians did. Defend yourself like Chileans did. Okay, so they take inspiration from different mobilizations worldwide. And they're also very connected to the Syrian streets. They say they don't want to be these artists who are doing salon art. They want to be connected to the ground. They want to breathe the Syrian revolution and produce artistic videos, images, posters. So they have even designed graffitis that then you can see how they share them with Syrians on the ground. And you see these graffitis created by this group of designers. You see these graffitis on the wall with the face of Riyadh Matar and other martyrs of the Syrian revolution. So there's a strong connection between what they're doing, what they're designing, and the actual events on the streets so that they're not detached to the real thing happening in Syria. So it's a really great community that I really recommend. Unfortunately, it's all in Arabic. But the designs, I think, anybody can really connect with these kind of designs. Because it's very visual work they're doing. So this is the Facebook page, a little kid writing on the wall, I am not a slave, I'm a worker, not a slave. So different kinds of resistance against brutality. This is Yara Shamas. She was a very young girl who was arrested by the regime. She was only 21. So they remix things that already exist and create new forms of art for Syrians to use. Okay. And so it's Syrian Intifada is the URL on Facebook. It's Syrian people know their way, Syrian people know where they're going. And the Syrian struggle is so dramatic. And the violence they are facing is so dramatic that they have managed to attract global solidarity after years, after decades of silence over Syria. So there's a lot of campaigns that you can actually join if you guys are interested in contributing, in spreading the word about what's being done in participating, in getting involved, there are many ways to do so. This is a global solidarity campaign. So it's on Syrian CTEEN on YouTube. So I think you can still send videos, I'm not sure, to this channel called Syrian CTEEN on YouTube. So you can record yourself saying, I am in solidarity with the Syrian people, like Shandith. I am in solidarity with the Syrian people. I reject the brutality and killing that the Syrian authorities are committing against the Syrian people. Because silence is participation in this crime, I declare my participation in Syrian CTEEN on YouTube. This is another initiative called Global March Against Syrian Dictator. This is a very important initiative called Global March Against Syrian Dictator. Let me see. For over a decade, a dictator ruled the land of the iron fist. In 1982, he killed over 40,000 innocent civilians to crush the revolution. He killed more than 50,000 people in the people of fear for decades to come. On March 15, 2011, Syria's society had enough and the revolution ignited. Hundreds of thousands of Syrians from every background took to the streets in peaceful protests. Bashar al-Assad responded viciously and without mercy to the young and the old. In less than a year, he killed over 8,000 civilians, displaced 20,000 neighboring countries, and detained and tortured over 200,000 people. But one year later, Syrians continued to call for freedom and they also called for our help. I'm Canadian and I'll be joining the World Wide March for Syria. I'm Palestinian and I'll be joining the World Wide March for Syria. I'm Romanian and I'll be joining the Global March for Syria. I am Christian and I support the Global March for Syria. I'm from Kurdish and I'm from the Syrian Free Syrian Liberation Army. I'm from France and I'll be joining the Global March for Syria. I'll be joining the Global March for Syria. I'm Marz. I'm from Tunisia and I support the Global March for Syria. We're all Canadian and we'll be joining the Global March for Syria. With every passing moment, Syrians are giving their lives just to be free. Let's make a fresh in history. Join the Global March for Syria. This was on March 15, 16, 17, but a lot more marches and demonstrations and events and initiatives will continue to happen. So I really encourage you to stay tuned. Some more things that can be done. Well, stay informed. This is a new site for those of you who speak English. It's called ANA. They share news and updates straight from Syria, Activist News Association. I really trust them. They're really reliable and they have good sources on the ground to stay really focused on how things are developing. They share, I think, interesting information. If you want to spread the word about the Activist News Association, I think it's a pretty good site and work they're doing. So more things that can be done. Well, there are a lot of campaigns and initiatives to send help to Syrian refugees through different organizations like Human Rights Watch and the Amnesty International are doing reports on what's happening on the ground and there are also different campaigns to actually contribute economically with the refugees on the Turkish-Lebanese borders. So you can demonstrate at your Syrian embassy. We still have not managed to isolate the regime internationally. The Syrian ambassadors are still in European countries, continue to do their work in spite of the brutal repression against their own citizens. So I'm sure there are demonstrations here too in every country. I'm aware they have demonstrations at Syrian embassies. So pressure your political representatives for consistency within support of not only Syrian civil society, but everywhere in the Arab world and everywhere in the Middle East and North Africa, a lot of these regimes have been able to stay for so long because they had support from diplomatic support, economic support, political support. So it's time to start listening to citizens, to citizen demands, to citizen needs, to citizen demands for freedom, justice and dignity, and not to repressive governments that do not represent their societies and their peoples. So pressure your political representatives for consistency, diplomatically, economically, politically, and well something we need to keep doing is pressure Russia, which is the one big supporter of the Syrian regime to this day. Keep spreading the word, blog about it, tweet about it, like the movie The Network says, get mad. So please get mad about what's happening in this country and everywhere in the area. And now, before we finish, I would like to ask you for a little favor, if this is okay. And I'm going to ask you to raise your hands for the Syrian people. So I would like you to raise your hands like this, and maybe you can take, wait a second, maybe if you have a camera and want to also take a picture of each other and then share it on Twitter, because right now I'm afraid I don't have connection, but I'm going to share this. I'm going to share hands up for Syrian activists from Berlin, RP12, which is the tag for Republica, and then Free Syria. Hands up for Syrian activists, hands up for Free Syria, RP12 and Free Syria, so I'm going to take your picture now. See, when I do this, I always have like, again, hands up for Syria. And thank you very much. Thank you. So, a few questions. Hi. So, from Switzerland, a question about how the regime is preventing access to internet. We know from China and many other countries that this is obviously something they try to do. What's the stand in Syria, and what kind of technological solutions do you have to convey in that? Well, we have another conference coming after this one from an expert from the electronic frontier foundation. I think she's going to mention some of this, but they have been blocking sites for years on and off. Unfortunately, a lot of the technology these governments used to surveil citizen activity online, not only in Syria, but in the rest of the area, most of this technology is made in the US. So, now there seems to be an attempt from the US administration to control exports of this technology to repressive regimes such as Syria. And we'll see how that goes. It seems like a step in the right direction. Are there any more questions? Oh, right here. If I would get in contact with friends in Syria. With who? With friends in Syria. Friends. Are you okay? Yes, I'm okay. I didn't try it yet. Can I be kind of risk for them if I try to speak with them about the truth? Or do you think if ever the connection will be possible, what other people told me, it's not easy. I think that it will be hard to know something, what really cares. Do you think that a call from Europe or Germany can put people in risk? Yes, it can. Yes, it can. Nothing is safe communication wise at this point in Syria. Syrians are relying on Skype a lot. Skype is not safe either, but I guess it's a little safer than mobile phones. Especially when communications come from abroad, they're more controlled and more surveilled even than communications within the country. When people out of the country talk to our families in there, we have very casual conversations on average things. We don't ask about the situation on the ground. So yes, I would not recommend openly discussing these kind of issues on the phone with Syrians. This could actually endanger them. Another question? Do I see something in my hand? No, not right now, but Leila will be back later. That's exactly what it's all about. Thank you very much from here. I think we'll see you later on. Thank you very much.
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Over the last months, Syrians have struggled against a 41-year-old wall of fear. Activists have become more creative to ensure attention towards the situation in the country continues and have managed to create their own narrative in the land of state-controlled media. In this presentation we will see different examples of citizen expression in Syria, which keep growing despite attempts by the regime to silence them, and different initiatives in which citizens all over the world can take part in solidarity with the Syrian struggle for freedom.
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10.5446/21410 (DOI)
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Good afternoon. I'm Patricia from University of Siena in Italy. Before starting my talk, I would like to say just a few words about my university and my department. We started in 1992 and in Italy, my department, it is communication science, was quite an experiment at that time because we decided to mix people from communication, psychology, technology, design, and so engineering and we work all together, so still work all together and I will show you some of the results of our work, of our projects. But for me, it's important to say that this multidisciplinary is a value for us, so we really want to mix and to share and to exchange and I'm available to do this for you today, so even after my talk, if you want any information, I'm very happy to stay here with you. So the title of my talk is Beauty of Interaction. So I will try to say something about beauty, what is beauty for me and before starting, I would like to say that this work is, was started a few years ago in collaboration with other groups in particular to explain what beauty is, beauty and interaction is for me. I would like to start quoting Kei Soverbeke who was professor at the Technical University in Soven and very sadly passed away a few months ago but I'm very happy to share with you the work that I did with him and this is also a way to continue his dreams and his activity. So speaking about beauty and interaction, Kei's was used to say that design is about people, is about our way of living, our hopes, our dreams, our loneliness and joy, our sense of beauty and justice, it's about the social and the good, it's about being in the world and in this context it's a very poetic approach to the design of interactive technologies. We were and we still are convinced that meaning is in action, meaning is in interaction, it's not that we find something that we can find in the world, that's something that we can teach to our students, it's something that we construct together. So this is the main vision of this talk and the approach and instead of explaining this in words I would like to start with two videos and these videos will be commented just afterwards. So this is a lamp, an interactive lamp that was designed by a PhD students at the Technical University, Eindhoven and this is Philips Rose and you see the lamp, you don't see any switch and the lamp just invites you to explore, to touch, to stroke and sometimes the lamp doesn't know exactly what to do so it has to be in a sense reassured about what to do, where to direct the light. And you will see in a while there are different ways of interacting with this lamp. Mainly stroking and the material of this lamp is extremely pleasurable to stroke and to touch. So it's a learning process, the lamp and the user are interactive to learn user preferences so what is really needed at that time to have a good experience of reading. And now let me show another one, another lamp again, this is another student project, this is a master project. This is a different kind of lamp, again, you interact with the lamp, there are no switches around and you try to adapt the way to use it. But then you see sometimes the lamp doesn't want to collaborate at all so maybe you have to try again and try to convince. No, there is no way. Okay, so why people should buy a lamp like this, a lamp that maybe doesn't do what is expected to do. And the reason for this, I thought that this was a good example for this concept of beauty of interaction because these lamps are about opening their functionality to the action of the user, they are about exploring, they are about trying things. So they are open to our perceptual motor skills. But they are also about reading and they are also about feeling good about beauty, reading a good book maybe. So they are about emotional skills. As I said, they are about reading, so the cognitive is there. And there are also about values, values are personal but values are social, so they are about social skills. And this is what beauty of interaction is about, is a combination of these. And these lamps are physical hypotheses that show what is the value behind design for beauty in interaction. And this is something that we try to teach to our students. And so I want to show you other videos and other projects from the students. But before having a look at these videos, I would like to say that having the beauty in mind means that the designers have to create a context for an experience first of all. And so they don't have just to design a good product. They have to offer a context to enjoy whatever, a film or to work, sharing, staying together. But it is important to do this in a beautiful way. So using all our skills in a very natural way. And it is important that technology is embodied. So we use our body to interact with interactive technologies. And first of all, it is important that technology is experiential and respectful. Let me explain what I mean by respectful. And try to imagine this situation. You are in a shop. And the shop assistant threw the biscuit at your feet, just doing this. And you bent down and you began to pick up the crumbs. And after some fiddling, you managed to get your change out of his fist. So could you ever accept a behavior like this in a shop? Never, of course. But this is exactly what we accept when we use a vending machine. When we use a vending machine, we insert coins and sometimes we have to take the bottles doing something like that, put our hands in dirty holes. And, okay, I have quite an example of really an acceptable vending machine that we use every day. So starting from this example, we asked our students to design new vending machines having beauty in mind. And this is what they did. So So first of all, the vending machine tries to attract your attention, the machine that can't follow the movement of the person. And then also they were very much focused on the way in which the machine opened, because this is something that is really bad sometimes with some vending machines. And again, everything, also the gestures are extremely natural. I want that. I don't have to type numbers, for example, because typing is, of course, something that can lead to errors. And again, you can waste your money and so on and so forth. But the way in which the experience was reinterpreted by the students was quite interesting to see. And then there were, of course, other examples of you couldn't call these vending machines, but let me show what they tried. They tried to have a kind of expressive interaction with the machine that tries to give you something. And the first example is a machine that is a bit nervous and maybe scared about your touch. So the machine doesn't know exactly what to do, but at the end it gives the small nuts. And the other one is very poetic and beautiful. This is the second one. So, the second one is strange. It's not very convinced, so. So there is a way of having expressive technologies and a very simple, natural way to interact with such technologies. And everything should be extremely embodied, so we don't need necessarily interfaces that we design just to interact with the technologies. We can use our body and we can use the environment as it is possible to see from this example. This was another project from a master student who designed this system to listen to music. A little update about the technology that working with software. They used to fit up on the same old broken mind You picked you So, this is the context of of the work that I'm doing at the University of Siena. And these are some of the examples from the students' project. But what I'm trying to do now is to try to challenge this approach in different domains. And one of these, an extremely challenging domain for applying the beauty of interaction, is the health care. So the rehabilitation and care in general. So what is beauty in therapy and care? To me, this is really the experience of use that lead to a feeling of engagement and also to the hope of the recovery. We all know that when doing rehabilitation, for example, physical rehabilitation, is extremely boring. You have your problem and you have to repeat again and again the same movement. And people don't want to do this. And in particular, children don't want to do this. They get bored and that's it. And so why don't we try to make also rehabilitation a beautiful experience and engaging experience? The other point is that rehabilitation tools manifest disability. They are awful. Awful to wear, awful to touch. And they immediately manifest disability. So is there anything that we can do to avoid this? Is there anything to make them playful, engaging, surprising, nice to use, beautiful to use? And the other point to me that is very important is that rehabilitation usually focuses on impaired perceptual motor skills. And so what I'm trying to do is to recombine the other skills that are still intact in people who have, for example, physical or cognitive problems, and then to use them in combination without focusing on the disability itself. So this is the context. And when I try this work, few... Sorry, it is not easy to read the first question. But the question was, it is possible to design with... To have an aesthetically-minded design to develop rehabilitation tools. And yeah, there are some attempts. These are nice examples that I saw that I found on internet. And the first one, these are crutches that are made by ceramic. They are very nice to wear and to touch. They are very elegant. And these are other examples of these kind of tools that are, like, a bit fashion. But to me, what is important here is that the beauty is not only in appearance. The beauty is in interaction. So how can we design rehabilitation tools that are pleasurable to use? I started a few years ago, as I said, with this topic that I explored in different projects. In particular, I used... And I'm still using robots for autistic children, for example, for elderly people, and other kind of interactive tools. I will show you some examples of this. And this is the first example. I worked for a few, I would say, a couple of years in home care with elderly people, and in particular for people affected by dementia. And the problem they have, in particular, is isolation. It's the isolation. They don't communicate very much. They sit most of the day waiting for lunch and dinner, mainly. And that's it. And it's extremely difficult for them to get in contact with other people, to communicate with other people, because the language is impaired. And so, since they, in some way, realize this, they refuse to communicate with other people. So I had a team at that time that was... It was an international team of designers, and we started this project, and we developed what we call the rolling pins. They are cylinders, plastic tubes, mainly, that can communicate with each other. And they can produce different kind of feedbacks, sounds, lights, and vibrations. And what is interesting is that the system, that these rolling pins are used in two or three people, at least. So when you shake or you roll one of your rolling pins, that is a cylinder like this, the output of your action is reflected on the other pins. And whenever the two person make exactly the same kind of movement, the pins vibrate. So this means that you can perceive the perception of the other person. And when you tune each other, when the person tune each other, you can feel that you are doing exactly the same. And for the therapist, this is quite important when you are able to tune with another person, because this means that you are able to read the mind of another person. And this is something that people with dementia cannot do. So this is... Let me show you the system, how it works. Oops. Let's go again. Okay, so I tried this system with elderly people in this home care. And we did an experiment. We divided the people in two groups, and one group worked or tried the system in a condition where the two rolling pins didn't communicate each other, and the other group worked with the system in the condition where the rolling pin communicated each other. So this means that the person could feel the perception of the other one, so making the same kind of movement. And you can see the results of the... On the right, you have the therapist. And this is the first condition when the rolling pins don't communicate each other. You see, the person doesn't do anything, she refuses to put her hands on the rolling pin. But this is the condition in which the rolling pin communicates with the person. There's very little T faith in anyone, there's no T faith in anyone, and you can see how the person communicates with the whole system... One person doesn't communicate So, we analyzed all these videos with the therapist and the doctors. And what is interesting to see is that they interpreted the different movements, the choreographies of movement in a very specific way. They said that this is a kind of non-verbal dialogue where you express a kind of relaxation when you do something like that. So it's a very easy movement or anxiety and effort when they did the rotations. So, it was a way to communicate with the therapist about their internal states. And again, you can see here a combination of sensory motor skills and perceptual skills and visual and cognitive skills and social skills. So it's really a way to get in touch and to try to also to involve in the activity skills that usually are not very much practiced by these persons. So this system was really successful. It is still in use in this home care in the north of Italy. This is another example. It's another system for children with cognitive and physical disabilities. The system is called active surfaces. And the idea here and the beauty here was to work in the water because the water is really a fantastic context for the rehabilitation. In water, even people with physical disabilities can move autonomously. So children with physical disabilities can play with other children. They don't need any other support, they can move. And also children with cognitive disabilities can be, can play in this kind of environment because the water is extremely relaxing. So it helps to maintain the focus of attention during the activity. And so before this, before the system was developed and tried out in a real context, I asked my student to think about, to develop concepts of these kind of systems, having this idea of the beauty of interaction in mind. And you can see what they did and the very sophisticated techniques that we use for prototyping ideas. And we usedsudden transitions when we applied the Cute future systems for. This bird oferture incident as that. You are my angel You are my angel Dave! You think you're gonna save another girl Dave has a few photos And I can love you You talk to this girl You feel the end of the time You're hot I like to dream about you Like in my dark Every man is alone But I don't want you Don't be where you go Because I love you I don't want to love you No Dave You're hot I like to dream about you You got to believe You believe Dave You're hot I like to dream about you Like in my dark Every man is alone But I don't want you Don't be where you go Because I love you And I don't want to love you No Never want to love you Never Never never ever Won't love you And I feel you All my angel And she gets to love you So, it's just the pain So, it's just the pain You know? This is more or less the way in which we prototype ideas and we work with the doctors and the therapist It's extremely easy to develop concepts and to show to the people in a final system. And it was developed in the form of floating files instead of working on the floor of the swimming pool. And again, there are modules. There are tiles that communicate each other. And you can do different kinds of games, like the Scrabble games or Sequence games or matching colors and these kind of things. When you put the tiles in the right sequence, the configuration at the end lights up. So again, this is an example of combination of physical and cognitive skills. And also, children really love to play these kind of games. And it is a way to continue the therapy. Again, this is still in use in Siena, in a swimming pool in Siena. The second context in which I'm trying to challenge the idea of beauty of interaction is education. And of course, this is extremely important for us, because if you don't train people in designing with this idea, you don't have prototypes and system to try out. And there is no way to have a societal impact if you don't develop system like that. So to see if this idea of beauty of interaction can really have an impact on the society. And this is an example of a project that we did last year. It was a module. It was a design school, an international design school that was called Light Through Culture. And the idea was to wave technologies, light technologies, and to introduce them in a very rich cultural context. With the idea to learn together how to use light technologies to express meanings about history. And we didn't do the module at the university, but we did the module in a museum in Siena. That is a special place, because it was an hospital. And now it is a museum. It's a very big building. And we gave them a very difficult design brief. So we actually asked them to design an experiential route, trying to explore the fact that this museum is built on the Via Francigena. Via Francigena is a pilgrimage route that was used by pilgrims from France and UK to go to Rome. And Siena was one of the places where the pilgrims stopped and to rest a bit and then to continue their path toward Rome. And so the questions that we asked the student to respond were, are the tourists the new pilgrims? What they look for when they start a pilgrimage like this? Do they look for hope, for silence, for enlightenment? So again, it was a very poetic way of thinking about the history of this place. So as I said, we asked them to design this experiential route. And we tried to address their craftsmanship and their different cultural and educational background. We had six students from Eindhoven and six students from Siena with different backgrounds. And they took the full responsibility to design this path. And the school was organized in three phases, mainly. The first phase was about opening sensitivities. So we asked them to go around and to be inspired about the space, so about the smell, the gloom, the darkness. Just really stay there. The module lasted two weeks. And in two weeks, they had to design and develop the installation. And then we opened the exhibition to the public. And then they studied about, part of the module was dedicated to the history of the place. And then the students split in groups. And they started making, just playing with technologies, like technologies, and tried to see how to use arduino boards and sensors and actuators to build different installations. And the third phase was about the reflection, so opening the exhibition to the public and trying to involve visitors in discussions about what they visited, what they understood, which kind of experience they had from visiting the museum. And they did actually quite a good work. This is the path in the museum. So there were five different installations in the space. And I want to show the first one, that is this one, 0.0. And this is the introduction to the space. Who are, in this day and age, the new pilgrims? Are they the tourists? What are the insights? And what are the discoveries that could be made along the way? Enlightenment? Hope? Silence? Our story takes you on a personal pilgrimage through life. We came from the north on our way to Rome and finally reached Siena, on the way we got to know other pilgrims. And we are now sharing the difficulties of our journey through four spaces. So this is the first space that is quite interesting space. This was the morgue of the old hospital. And when people died, they stayed there for 24 hours before dispensing the blessing. And since there were no scientific instruments to establish the death with certainty, the doctors were used to put a bell attached to the ankle of the corpses. So if in 24 hours they didn't see any sound, people were dead. And this was the way in which they treated people. And this is the interpretation of the students of this space that was called the Room of Uncertain Death. It is called like that. So So the space is fully interactive and also the next one that is called the washing facility of the wet nurses. This is a washing facility that dates back to the medieval age and the water were collected in these basins, this washing facility and were used by the wet nurses to wash the clothes of the orphans that were hosted in this place. And the students interpreted this space in this way. So this is one of the corridors. They simulate the water leaking from the walls with the light. And this is, they simulated the water inside the washing facility with a smoke machine and everything is interactive. So the idea is that if you pretend to wash clothes, then when the clothes are cleaned, the water changes the color. So they reproduce also the sound of the space. So if you are interested in having a look at the video of the whole exhibition, the video is accessible there. And I want to finish my presentation going back to the vision of this work. And as I said, this was basically the idea of working with the beauty of interaction came from exploring and trying to develop a theoretical framework. And then now, after a few years, is something that we are really using and challenging in specific application domains. And the ambition is to create in our labs, in our universities, an innovation space where creativity can meld with research and development. And also as a way to develop new methodologies to teach and to learn and to design to understand human activity in the world. So this is really the vision. And there are some central themes. I'm sorry you cannot read this, but first of all, the focus of our work is the human activity. We don't work in the lab. We work in the real context of use. Sometimes the context are also quite challenging, working in the hospitals, in the schools, with people with different problems also in their life. Everything is, all the technologies are really embodied. The interaction is embodied. The interaction is extremely natural without any kind of interface rather than the body and the environment. Engagement is a key word. So we want to engage people. We want to create space for opportunities and for experiences for them. And interaction is the key point. So we see interaction as a narrative activity where people can put their meaning inside. And interaction is multi-modal in the sense that it has to incorporate several sensory modalities. And technology here is interpreted as augmentation. So we don't want to view technology as a way to model us and to understand our needs, but we want to develop these needs and the support in interaction, during the interaction. So the very closing slide of my talk is this one. I really like this piece from Masaito and Morey, and I would like to read this with you to close my speech. And he says that an individual's overall capacity to judge things changes completely depending on whether he possesses a sense of pathos of things, sensitivity to beauty, and compassionate empathy. These things change once we're calibrated as human beings. And this is the reason why we believe that design can really help in trying to compose this view and this framework. And I hope that we can also try with our students to bring this idea of the beauty of interaction in their design, for developing their design skills. Thank you very much for your attention.
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In our everyday living we inhabit complex technological spheres of life that require a novel and more 'ecological' understanding of our relationship to technology. New kinds of pervasive sensor-based and embedded technologies entail a very different understanding than traditional user interface design activities. People are confronted with new demands and increasingly complex technological infrastructures and ecologies. As designers we strive to manage such complexity and to develop systems that seduce our senses. As ordinary people we would like to get rid of such complexity and interact in the digital world with rich interaction possibilities as we do so well in the physical world, using our intuition, motivation and enchantment towards objects. The challenge is how to exploit this complexity and new possibilities for novel applications and experiences, which are inviting, witty and playful, original and fascinating, and last but not least, improve life and people on an individual or societal basis. The Aesthetics of Interaction will be the focus of the talk. Design cases will be presented to challenge the approach in different fields of application, from everyday life objects to the health care and rehabilitation domain.
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10.5446/21415 (DOI)
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It's a real, real honor to be here in front of you, to be here at Republica. It's a brilliant conference. I'm very thankful that I can represent not only myself, not only my country, but also the continent in some respects. And hopefully, as you get to know each other and as you get to know my story and I get to know yours, hopefully we can discover something new. So Time Magazine, famous magazine, brilliant magazine, and in January 1984, they ran a cover story. It speaks for itself, Africa's wars, coups, conflicts and corruption. And these three things dominated the discussion around the African continent. And the truth is that up to today, a lot of people still seem to associate this with the African continent. There's two main stereotypes you could say that personify people's ideas about the African continent. One, war, crisis, poverty, guns. You've seen it, you've heard it, I don't need to repeat it. The second is it more exotic, right? So beautiful vistas of gazelles, antelopes, everything you can imagine. And these are the main areas which seem to dominate trains of thought when it comes to the African continent. So much so that years later, you could say, 16 years later or so, the economist ran a very interesting, this is the year 2000, actually this month in the year 2000, they ran a cover story and made a very declarative statement on Africa, calling it the hopeless continent. And all this would really lead you to believe that if all this were true, that if all this actually summed up the sum total of all these people on this vast expanse, this continent, then what more is there really to learn? What more is there to know about Africa? Besides our uncle with a large inheritance which he seemed to leave you and contact you via his cousins on email, we've all been there, we've all gotten that. But there's so much more that's underrepresented, you could say. And I think one of the best ways to show and showcase this is with an analogy. And it has more meanings than one. If you remember NASA, big, big portrait of the world by night, covering the entire expanse of the earth, watching and looking for where the bright lights shine, where people are, where electricity is, civilization if you like. That's become an iconic image that describes the world. And if you look, you'll see for yourself that in more ways than one, Africa is the dark continent, an absence of light in this particular picture, bearing testament to that. And yet, if we look at some work that came out of Facebook last year as well, or in 2010 rather, by an intern in the data visualization department, and we look at the number of connections that were visualized on the Facebook network all across the world, we see a very interesting pattern and there's a gentleman who actually went to the extent of combining both photos and overlaying them to see what happened. It might not be as clear here, but we'll zoom in on Africa in a second. But what you find is a question bigger than NASA could ever present to you. And that is, if indeed there's no electricity, if indeed there is no light, and yet the presence of people is there, and the presence of some level of technology, then what gaps are we missing when Facebook shows us what it does with all those connections coming in and to Africa? If we look at Africa here, it's not as clear here, I apologize, but what you'll see when you overlay the two images is three or four hotspots. In sub-Saharan Africa, it's in West Africa, it's around Nigeria and Ghana. In East Africa, it's around Kenya and Tanzania, and in all through Southern Africa, it's present. And what this tells us is that there's more to this entire debate and there's more to the hopeless continent than meets the eye. And technology is the key to that entire debate. So if we look at some statistics that McKinsey did in a recent study a few years ago called the GDP of all these African countries combined came to $1.6 trillion. And this is close, and present day especially, much closer if not past Russia or Brazil. And if we look at the African consumer, their spending power, it was largely estimated to be around $860 million plus. Now of all the cities in Africa, there's over 52 cities with over a million people in each one of them. Fast forward to the year 2020, and the GDP has grown to $2.6 trillion, even amidst crises and as we've seen in the couple recent weeks, a double deep recession in a lot of developed countries. Consumer spending has grown tremendously to $1.4 trillion. And more Africans, 50% more have moved towards cities by this year. Now that among a lot of other factors is what led the economist 11 years later to come full circle and release this cover which some of you may have seen recently, which shared a new perspective on Africa and termed it as Africa rising. Now part of the reason, or one way to describe the reason Africa or the rising Africa, if you like, goes towards the title. So whether we call it tech Africa or the Silicon Savannah if you like, the name is not as important as the movement and as the series of changes that are taking place on the continent that leads not only from an economic point of view, but an innovation and business point of view globally that are going to shape this debate. So I think to sort of put some of this in context, we need to re-understand or get reacquainted with what the African continent is. And one of my favorite images to do that is an infographic by a gentleman called Kai Kraus and he looked at the true size of Africa. A lot of times Africa is just a passing idea in our minds and yet here we visualize and look and see exactly how many countries it can hold. I won't spell it out for you, China, India, Eastern Europe, Italy, Germany, France, Spain, the US. And if you look through the legend, there's a couple other countries as well. This is the size geographically of the continent and the numbers that I shared before cover some of the small idiosyncrasies behind it. Now if you look at the people beyond just this geographic expanse, it's people. There's 1.2 billion people on the African continent today. Over 620 million mobile phone subscribers, 140 million internet users and over 2,600 languages summed up in this one space. That's 2,600 local cultures to address. And so even the term African is as ambiguous as the term European, is as ambiguous as the term North American. I'm a Kenyan and then I'm an African in that order. And that's something which a lot of times no one might pay attention to but over the coming years as we begin to get a better view of Africa and Africa takes its presence on the world stage, we'll begin to see this. Now with all this said, there's one particular quote that sort of sums up that introduction to Africa. And I love it so much because I think it speaks not only to me but hopefully at the end of this presentation to you as well. And I look forward to engaging around it. Until lions have their historians, tales of the hunt will always glorify the hunter. And so the better educated you are, the better we understand what's coming from the African continent, the better we know what to expect and how to respond to it. Now, in 2002, there was over 49 million smartphones in Africa and now we've seen them grow to 620 million with 735 million by the end of this year. But numbers don't tell the true story. Numbers don't really get us acquainted with what's happening there. Now much of the developed world, you could say, isn't used to seeing phones like this. And now it's smartphones. It's the iPhone of all phones dominating conversations across the developed world. And yet this, the Nokia 1110, this in particular, known in Kenya as the Muleka Muizi, which is a very funny analogy around its flashlight, it's useful. And this is really, this is one of the highest-spelling smartphones by Nokia itself. And this really captures part of the sentiment of how many people have access to a mobile phone in Africa today is actually more than people with access to the radio, another level of mass media that we've come to become acquainted with. Now as we look towards this and get better acquainted with what Africa is doing in terms of mobile, we need to take a step back and look at how the entire world has experienced the internet up to today. Now this is a mobile, I mean this is a call box graveyard if you like. And this is a stage that entirely passed Africa, the stage of fixed lines and the age of experiencing the internet on a computer, all right, on a personal computer, on a PC or a Mac if you like, that entire stage is being questioned now, its relevance is being questioned and a lot of times it's been deemed unnecessary. And what we'll find with a lot of the innovation coming out of Africa is that it completely goes against the historical status quo in that you experience the internet through a PC and then some sort of handheld device, be it a laptop, be it a smartphone, be it a tablet and just going straight towards a mobile phone and seeing what can you do and what can you innovate in and around that. So one story in particular that I think sums this up is the story of the IDEOs, which is a Kenyan story like none other. So people always ask the question, what would happen if there was a $100 smartphone, it would change the world, it would change the way people consume information and data. And in Kenya it did. This $100 smartphone made by Chinese manufacturer Huawei came into the market almost unbeknownst to many, a little bit of a buzz but not much. And in the space of one year, completely turned the smartphone market in Kenya, Android, and got an entirely new segment of people aspiring for a smartphone, using a smartphone and a touchscreen one at that. Beginning what has started for Kenya, a revolution towards the smartphones and cost effective ones, competing on price and competing on what they can offer the consumer. Now it's going to continue to disrupt and bring about different levels of innovation to us, leaving the typical pattern, the typical state of things in question. According to studies by the London Business School, the World Bank and consultants at Deloitte, for every 10 additional mobile phones per 100 Africans, the GDP is expected to rise. So the actual economy of the country is expected to rise, possibly up to 1.2%. But none of these statistics really tell the story. None of these really speak to what's going on. And one of the best examples is M-Pesa. Now M for mobile and Pesa meaning money in Swahili, this is truly one of the things that has put Kenya and continues to put Africa on the global map. Using SMS technology allows two people, wherever they are in the country, to send and receive money from each other without any need of a bank or any sort of financial institution whatsoever. Now that may not sound too interesting until you hear exactly how this has grown and specifically how people have used it to change our country. So 37,000 agents across the country and 15 million people using this service, which basically means it's everything from I walk outside this room and find one man who is an agent or I go into a mall and find a retail store that's full of agents who can serve me and allow me to deposit money into my phone. But again, it's what people have done with it that's partly the reason it's gotten so successful. The technology behind it has been exported across the world and it's become one of the leading case studies in the most mature mobile money market with 17 million Kenyans out of a possible 40 using this service and transacting and doing business with it. Now if we take an example, I have a friend, he's an artist, his name is Cyrus and he makes, he doesn't like to call them glasses or sunglasses, but he makes pieces of art that you wear over your eyes if you like and he uses scrap metal and a whole host of different materials. Now he relies on people who are in what's called the Jua Kali sector, Jua Kali meaning hot sun in Swahili and what this is is it's the informal sector in Kenya employing about 8 million people. Now they typically work under the sun, wrought iron, metal, woodwork and it's a very high sector of the economy to place because of how informal and unregulated it is. And yet the way they use, the way supply and demand works in that sector, takes Cyrus's friend, the gentleman who helps him with these different pieces of metal and how he really finds what he turns into art. His name is Ezekio. Now Ezekio, for him to get his work, he goes into a certain market and he has to go there physically, select a number of things, arrange for delivery and then go back and wait for his materials to arrive for him to work on them. Now with Ampeza, how that's changed his workflow is through him being able now, just his phone, sending as little as 10 US cents if you like to as much as over just well over a thousand euros or a thousand four hundred dollars to any one of these suppliers and coordinating the supply and delivery. So what was previously just a cost of doing business, he does not have to leave any physical space to conduct business in quite the way anyone with a bank account, anyone with a checkbook would be able to. Doesn't sound like much but that's partly what's going to drive the next half a million jobs that are created in the informal sector every year. Now majority of artisans, majority of people in Kenya have been classified as the unbanked for a long time and this speaks to a lot of people in Africa as well, no access to financial services and yet something like Ampeza breaks this down to the point where regardless of the phone you have, regardless of the bit of technology you have, as long as it can send an SMS both ways, you have access to this. Now all those stories don't mean anything until you get a sense of how Kenyans are using this. This past December for example, in just the 30 days of December Kenyans sent amongst themselves over one billion euros in this person-to-person transfers, 30 days one billion euros. All right for a third world country and 15 million people that's not too bad and 60% of that is amongst each other while the other 40% is to businesses showing that for a market like this that's unlocked a whole new segment and created if you like disrupted banking and finance as we know it. Now that technology has been exported to a whole range of countries, Afghanistan, Haiti right now, some of the big examples, the US in some cases, Barclays just opened up something I believe a few weeks ago in the UK, an app called Pingit, allowing people to exchange goods and services through this app that mirrors Ampeza and how Ampeza works. And so what began as simply an experiment to get people to save, to get people to transact money amongst themselves has really been exported to a whole new level where people are now able to transact and rethink the entire level of financial services as they knew it. In Afghanistan, one of the most interesting examples, the police force all across the country would be paid using cash and so you have middlemen and because they are dispersed across the country you have challenges like the Taliban, it was a very sensitive way to get money to them. And so they were one of the first cases to implement Ampeza, all of these policemen have mobile phones and so it's possible to actually get direct access to them even though they will never have access to any sort of bank or financial services. Now one of the interesting things they found out of this was that as they began to send Ampeza to each one of these police officers now, they found on the payroll that 10% of the entire payroll were ghost workers. And so this money had just been going as cash and disappearing along the way and yet they never knew it. And so every one of these police officers afterwards gets a mysterious pay rise when they actually correct everything. And now you have more motivated people who are being paid almost better than the Taliban wondering how this could really have happened. And what that speaks to is that the amount that you're able to communicate through Ampeza is simple. It's one to one and all these people needed to do by cutting out the middleman was now go up to someone and withdraw. And that's I think one of the best examples so far of Ampeza really starting out Kenyan and going global after that. So one large payment innovation doesn't mean much for an entire continent unless you look deeper, unless you look for more stories, unless you look for more evidence behind the fact that Africa is actually exporting global technology. One specific way and this needs no reminder to republicans, there was someone here who elaborately shared this story last year and that was Patrick Meyer. What he was able to do alongside a group of bloggers and technologists across the world of Kenyan origin and some from different parts of the world who are connected to Kenya. In 2007, 2008, Kenya held what is today a disputed or contested election. And as a result of that, the country got into some unrest, you could say. And out of this started in what was just a blog post from someone asking, how are we going to know what's going on? You can't be playing the sound of music when people in town are rioting and chanting and so much unrest is going on and the media won't show it. So Ushahidi was a response to that. And Ushahidi has in the space of five years now, five, six years, has become one of the 50 most innovative companies in the world according to MIT's tech review and one of the five most innovative companies in media according to Fast Company. Now all they do, all this was and all that they improved on was if people have no access to technology and people have messages they wish to send, it could be Twitter, it could be SMS, it could be email, whatever means and whatever access you have, if you have a message you'd like to send, how can we gather everybody's message, visualize it and make decisions upon that? And this is actually the very first Ushahidi map, but now, I mean, from the Haiti earthquake to Snowmageddon in the US to almost every single major crisis in the world where people had a large amount of information they needed to make critical decisions, Ushahidi has actually played the role of coming through and visualizing and helping them make sense of that data. And this is one example of a company that's focused not only on using just technology but web technology to influence the way the world operates and shift the way we consume and make decisions on information. And so last year, they began a number of ambitious projects and two of them, SwiftDriven, CrowdMap, were touched on just slightly but speak to a very, very critical part of where the web is headed and this is all being shaped, this entire debate, this thinking is being shaped out of this technology company, this Not-For-Profit free and open source technology company in Nairobi. SwiftDriven, for anyone here, I bet if you've been trying to keep up with the stream of tweets at the event, it's been a bit difficult, you could say, to capture everything with tweets and that speaks to just our experience of the web or where at least that's going. The web is like drinking from a fire hose and to make sense of every RSS feed and every blog you ever subscribe to, every Twitter personality you follow, every email you receive and if you like every SMS, it would take you a while to say the least and a lot of us are caught in that attention span crisis of sorts. Now from this Ushahidi, based on the experience of mapping out crises where people are SMSing for help, for resources and needs, have taken to the web as their next challenge with SwiftDriven and what this is aiming to do is to take that entire challenge and represent it in a new light using algorithms and the like to distill and create a custom curated feed for you. The beta is out now, it might be private by the time I end this talk, but it's definitely something I'd say to pay attention to, especially over the coming months and years. Crowdmap on the other hand is a plug and play example of Ushahidi. Ushahidi is technical, it can be tricky to implement and yet with Crowdmap, in the same time it will take me to finish this talk, any one of you could have mapped out Republica and how many people are here and what they're interested in and if you got everyone in the room to participate, you could have a pretty interesting map. That's the kind of level of data and especially big data with what they're working with that's being shaped on the global stage thanks to their minds and what they're doing. Now this is a pretty brief screen grab of the platform which is a bit hard to come by if you ask, but I'm sure like they said it's private beta and it might be changing, but everything you can imagine regarding big data and where the web is headed in general, they are on the Kaspov and they're innovating around. Now their office and the hub where they operate from in Nairobi, the iHub, a place where I've spent quite a bit of time myself, is also at a much smaller level, less than M-Pesa, when M-Pesa creates this sort of fertile ground for disruption, what is the outcome? What do people respond with? One example is the iHub, a physical space in Nairobi that houses about 7,000 of Kenya's most creative people in technology, in business, early stage financing, design, you name it, there's a lot of brilliant people there. And this space, this hub has brought together the entire city and given it a nexus point on which to innovate, to test, to try out new and innovative apps and so on and really to create not only for the Kenyan market but for any market that has access to this kind of financial services like M-Pesa or to the mobile web like the rest of the continent. Now if you look at the rest of Africa, you might be wondering, there's not much going on outside of Kenya, but you would be wrong if you said that. Now some of the apps that are being made in places like the iHub and the M-Lab, there's two of them, are really remarkable in how they've been able to scale and how low tech they seem to be, at least from the outset. I'll pick a couple to share with you. My cow, I don't know how many farmers we have in the room and this caught me by surprise, but one of the most critical things about livestock farming specifically dairy is knowing when your cow is pregnant. Now it doesn't sound like much, but for a country which, you know, part of its bread basket, part of one of the real growth earners for the country's agriculture, this is incredibly useful information and to any farmer, small scale farmer mid-sized, to understand the entire gestation period of your cow, it's about nine months, is phenomenal. What iCow did is using a simple SMS solution, at least simple from the outset. It gives a farmer the ability not to use some sort of paper contraption to figure out and fill in and find their cow cycle, but to fill in a set of parameters about this bit of livestock. On average, if you look at each one of the cows, they give, I think it's 1.5 to 3 liters more on average as a result of this bit of technology. That's not saying much, but that has the potential to transform not only the African continent as it continues to succeed, but other emerging markets where agriculture and livestock and farming continues to be important. Koppokopo are connecting mobile money to the world and in more ways than one, what they're doing is changing the way we think of mobile money. I've been sending mobile money to my cab guy, the pizza hut, if you like, or the version of pizza hut or pizza chain, and all sorts of different businesses. And yet, I pay on time, I'm able to transact with all these large, large businesses, pay my water, pay utilities, and so on. But there's no way of these businesses acting on me as a person. To me, I'm just a payment that walked in and picked up a receipt. And what they're doing is they're casting the net out wide and allowing any small business to actually tap in and begin to act on the information that all these people seem to give. I give my mobile phone number so they can contact me and market to me. I also give my ID number so they can validate me and any other information about me and create a database. And more importantly, what it allows them to do is create a credit rating system for this entire mass of people sending, as you heard, billions of euros a month, or month on month, amongst themselves and to businesses, and allow them to act on that and actually build and innovate on top of this brand new layer in mobile money. Lastly, MFA, agriculture again. But for small scale farmers across the country, this would seem like not the best place for disruption. None of these are apps except Koppokopo, but these are there to operate exclusively on SMS. And what MFA does, it allows farmers geographically spread out to collectively negotiate and buy goods and supplies. It sounds like a problem which should be solved already. And yet with the mobile phone, what you're guaranteed of is a one to one ratio. And more importantly, a very personal way to contact each and every one of these people who cumulatively shape a lot of African economies. So in the 13 countries across the continent, you find a total of 35 hubs. Each one of these hubs is focused exclusively on technology amongst a range of other aspects. And what they're doing is mapping out, be it at a college level, at an academia level, or higher up, just seeking to disrupt the market. They're looking at applications, technology, and building to create some of the examples and hopefully better for their respective countries, showing that it's not exclusive to Kenya or East Africa, but it's something that's spreading. And it's something which, if this is all you've seen in a matter of months out of one country, what can you expect to see out of 35, out of 13? Now one example out of West Africa, which really, really caught my eye, has been MPEDIGRI. Now counterfeiters have a great advantage, it seems, outwitting the authorities and creating, be it counterfeit goods, or in this particular case, counterfeit medicines. Now every year the counterfeit industry in general accounts for $690 billion worth. And specifically for drugs and pharmaceuticals, it's $800 billion. In Africa, $100 billion. So you've got this large, large amount of fake medicinals which either contain traces or no dosage whatsoever. And the largest part affected by this is West Africa. Now what MPEDIGRI do is developed by a gentleman by the name of Bright Simmons, is they have sought to tackle this problem head on. And one of the most innovative ways to do it would be through the mobile phone. Again, it's ubiquitous. You've got, in some countries like South Africa, you've got more active SIM cards than the total population of the country. And so what this tells you is that if there's one way to reach people, there's one layer if you can successfully innovate on and scale, it's mobile. Now what they've been able to do is for every bit of medicine you get, you're able to see a code. And in seconds, you SMS that code to a short four digit number, and you get a response to whether that piece of medicine that you bought is actually legitimate. And this in the process, in the almost half dozen countries it's spread out to, just from an experiment, just from a proof of concept in Ghana. What this has shown is that meeting, it's doing better than just meeting the counterfeiters halfway, it's completely undercutting them and challenging Africans to ask and demand for goods that actually are legitimate, saving millions of dollars in the process. Now we've talked quite a bit about scale, and I think it would be unfair to discuss all of this without talking about what is arguably one of the continent's biggest social or social media related successes. Now Mixit is a social network founded in Cape Town in South Africa in Stellenbosch, and they continue to be a shining light for what's possible for the African market. Social network that started as an instant messenger client for feature phones, if you like. And now, whether it's your iPhone, whether it's a Blackberry, Windows phone, it's probably up next, they are completely spread out, and this is the number one social network in Africa by numbers, 10 million users, most of them in South Africa, tell me active users and 40 million users across the world. Large number of users in Indonesia, large number in Mexico as well, and some I believe also in Europe as well, Eastern Europe. Now Mixit is a story which many people have built off of and innovated around specifically in South Africa where the number of users on Mixit outnumber the ones on Facebook, that's set to change, especially across the continent. So given what we saw of the Facebook map, if they were to do that in present day, it would look a lot different than what it did at that time. Now one example of scale in Africa has to be an app that was built on to Mixit just two months ago. App is called Judge Me, not nothing original, similar to Hot or Not, one of those early internet web startups from the west. Now in the space of two months on Mixit, with this sandbox of 40 million people across the world, they got one million subscribers and over 100 million page views. Now that's not saying much in this part of the world. But you show me something else that's gotten a million Africans using that service, and now you're actually talking. One of the best ways to unlock that is typically to target feature phones and to target that level of the market and disrupt it. So these stories aren't one-offs. They're only the beginning, I could say, and if those hubs are anything to go by and the number of apps coming out of each and every one of those hubs speaks to a greater idea and that Africa isn't the hopeless continent, that Africa's walls aren't the only side of the coin to it, then really we've got to examine and see that Africa is really rising and the question is whether you'll rise with it. As one example, the most interesting one that came across and anybody here on Twitter might find this quite interesting. I know I did. There's a gentleman. He used to be a teacher, lives out in the Kenyan village, and came across Twitter one day. He saw it, loved the service, and in Kenya we have a couple of services by Twitter themselves and by Facebook that allow you just to send and receive via text. With Twitter, you do not have to be signed up on Twitter to receive updates from someone. Now, Chief Karyoki is the man I'm talking about and what he was able to do is in a constituency, in a district that electricity is not even guaranteed, let alone with every one of his constituents, he's been able to get an audience of just over 20,000 through his tweets. So he has a feature phone and all he does, just to explain it, is he writes these updates and informs the local people who have subscribed to his tweets. He has what are called Barazas, which is a gathering of people. Every month, he holds two. At each one of these two gatherings, he asks each one of the locals, whoever has a smartphone, sorry, not a smartphone, any phone, he tells them to send one text message. This one text message subscribes them to receive every update for free on their part. The network provider pays for this. What he's been able to get with this has been an entirely new group of people speaking with him. He talks about, I think he's foiled a robbery not too long ago by just texting and saying so and so, if there's thieves in this gentleman's house, we should do something. And then the entire village pretty much surrounded this house and were waiting to exact some measure of justice on this guy. But better still, I think what each one of these stories tells to is that scale, not only in Africa but the rest of the world, is something we've almost forgotten, something we think is lost in a world of WhatsApp and a lot of these other instant messaging tools and that's SMS. Building and starting from there and in some cases with voice, places where electricity is a big challenge. Working with SMS can actually unlock not only just the next million or the next 20,000 like for Chief Karyuki but possibly the next billion across all the emerging markets. Now Africa's weathered the financial storm of the global economic crisis and is said to become at least a lot of these hubs, as I mentioned, are said to become regional contenders. The 10 fastest growing economies of the next years are all African countries and according to the World Bank economies, 45% of Kenya's debt level is around 45% of its GDP. If Kenya was in Europe, it would be a top contender over the next 10 years. And what this tells you is that as you're thinking, as you're creating, as you're tweeting, as you're investing in the next level of business on this side of the globe, you cannot forget the southern hemisphere and more importantly, you cannot forget Africa. Thank you so much, your public. Thank you. Excellent. Thank you so much. That was just perfect for my eyes. Like I said in the intro, I was really trying to bring in people to tell this African story and we're really happy to have Patrick here to talk about Ushahidi but this full picture and just really telling people what's happening, I think you did a perfect job of that. Thank you so much. Now you also did a perfect job of timing so we have about 15 minutes left for question and answers so please, if there are questions for Mark, let's see your hands in the air. There's a gentleman in the back, please. So it's tricky getting that first question. I have zillions but I'll let the others go first. Can you give us an update on the ideas, the $80 smartphone, how many users are there currently? Right. So what he's asking about is the idea of smartphone and how many users. So the Sephardicum CEO at a gathering in January mentioned 300,000 but there's other estimates that would say that it's significantly higher than that. So that 300,000 is on the lower part but yeah, that's 300,000 and that went there eight, nine months ago. Claudia. Thank you very much for your presentation, that was really wonderful. I really liked it. I have two specific questions. One is about the user numbers for the agricultural apps, it wasn't really apps, it's services that you had iCow and the other one FFarm I think. Do you have any idea to what extent farmers are willing to use these tools in terms of numbers and the second question is your examples were very much concerned with service delivery, sending money and improving services in this respect. I would like to know how do you see the potential for using technology in governance issues. We talk a lot here at Republic about participation, accountability and these things and I think even in Germany most citizens are not really inclined to use technology and participate but I know that in the aid business a lot of people get very hyped about this and think this is the way to go and we need to use this technology to involve citizens so I would like to hear you view on this. Thank you. If you don't mind I'll answer the last question first. This is possibly another big hallmark for Kenya and that was last year Kenya became I believe it's the second country in Africa and the first in sub-Saharan Africa to open up all government data. What this has allowed is myself right now if I was to get a computer or anyone of people who are interested in taking deep dives into data and making visualizations or helping people understand what that data has, the Kenyan government has actually been digitizing a lot of this information and there's apps and tools now that allow for me for example to find each constituency in the country is allocated a fund so I can actually walk through the expenses of this fund like never before. No one had the power to do this, no one would want to go through the trouble of even finding this kind of information and now with a half decent connection to the internet I can access that and I can actually call up somebody, meet a local counselor, begin to ask questions, begin to interrogate what I'm seeing and that has been something which we began to see a whole range of different applications, tools and services built on that not only from Kenya but from the government as well, from the government as well. So I challenge anybody here to be honest, to give that a look and see what they can do there as well. Regarding your first question, I believe for iCOW I'm not entirely certain but I think it's important, it's quite a big learning curve. So even some research that came out this week that said farmers actually prefer to call over to text, long bit of research because a lot of assumptions are now being made in agriculture, oh well we'll just build this for them and now research like that is better informing not only Kenya's position but hopefully other African countries as well. Great, we've had three more questions in the meantime, I think we have space for four in total if you keep questions and answer short, it's you first please. Just a short question, last year I had a similar talk of Jessica Kula-Sao and I just wanted to know if you are connected to her in a way like an IHOP project or something like that, if you know each other or if you're working together. Yeah, so one of the startups that I'm involved with is a technology blog and so we do a lot around innovation startups, African tech and so we're collaborating with the IHOP working out of there and also with IHOP research which is the research division of the IHOP so yes, we've been friends for years. Thank you for your interesting talk. I actually have a question about the use of mobile phones in terms of like I read a very beautiful story that farmers in the countryside and boonies actually use phones for comparing the prices they will get for their harvest in different cities so it did change the way that the harvests were like marketed a lot and they obtain a lot higher prices. Now our smartphones also use family wise rather or group wise, is it like I don't know larger groups that use one phone or is it personal belonging like we use it, I think it's a different way how the tools are used isn't it? Sure, I'd say definitely on all phones in general it's typically someone, you know, the question of multiple SIM cards always arises so people will have more than one SIM card to more than one different provider and the phone is a very personal device and yet you know it's shared like in the example of Chief Karyoki what he said is that even if each home only had one person with one SIM card, there's three or four people who will use that phone, someone will send a text message or one actual innovation that was made for Africa if you like is what's called a please call me message. If I don't have air time and 96% of the continent is prepaid so air time runs out and I want to reach you, I can send you a free message that has an advert that's paid for by the telecommunications company that tells you to call me and sometimes in some countries you send, you know, maybe someone wants to know whether to bring bread home or not so I'll send you two and two is yes and one is no. So there's all sorts of different ways that they've built around that but to answer your question with smartphones in particular they become a lot more personal, you know, people have invested significantly in this and so it is more personal but with all phones, I mean if someone was to ask me, Mark, can I put my SIM card in your phone? I wouldn't think twice, I'd hand it to you. So there's a general level of it's accepted that you can ask me that and then it's more of a personal call. Okay, two last questions, Jens please and then the lady in the back. Just in the social media like Twitter is creating also a different layer of publicness of news. Sometimes you look on Twitter and then the eight o'clock news, you think what are they talking about? I know something totally different from my Twitter stream and I was following the Occupy Nigeria movement and I intensively and I followed a lot of the demonstrators, of the young demonstrators listening to the street, to the clashes, to what's going on and also Nigerian intellectuals who took over the chance to say it's not north against south, it's not Christians against Islam, it's another problem. So how do you think about the change of publicness of different layers of reality which are transported between the people? Do you see there any impact like for example if you maybe also know Occupy Nigeria as one example? Well obviously last year North Africa spoke for itself and it got to the point that they took action to the extent that this number of dictators were out of power. One interesting idea that I've been thinking about that I'm looking to write a piece about is that if you look at the 60s and 70s when Africa had between the 1960s, 1960s and 1970s, Africa had dozens of coup d'etats and that was acceptable somewhat to the world. The world was somehow alright with it. If you look in present day the coup d'etats frowned upon and people have outcries against it, but a social media upheaval is different and so maybe that's the new coup d'etat in present day. But specifically it's true to what my opinion of that is that's really opened up, like you said a new level of debate and examples in Kenya, this is a political year and almost no politician can afford not to be on Twitter, not to go that level of scrutiny from people. They're diaspora, obviously Africans abroad, a lot of them connected and then you have Africans in the country. So you get this balance of debate coming in and also debate being started locally and regionally. So I'd say you have different levels of society now getting acquainted. These companies who are saying we'll only solve your problem if you tweet us or we'll solve it faster if you tweet us. That's a Kenyan company, right? It's a Kenyan telecommunications provider. And so there's all these different ways that they're trying to get people to adopt technology and in the end I'd say it's definitely giving us a new spin. As far as politics is concerned, wait and see. This is again an election year for a number of countries in Africa and I think it's only a matter of time. A lady in the back please for the final question. So you mentioned the 2600 languages in Africa but it seems like a lot of the examples you gave are from Anglophone, English-speaking Africa. And I'm just curious to know what links are being made. I'm asking on behalf of some Muslim-Ecan friends who are geeks and journalists, what links can be made between French-speaking Africa, Portuguese-speaking Africa and some of what you've talked about. Thanks. Right. So I think for Lucophone Africa, I think in Mozambique, in a lot of African countries, I'd say Kenyans, people are trying their best to replicate Kenya's success. Kenya's a unique case in many ways but that doesn't stop them from trying to see if a lot of this will export and work in quite the same way. Now a lot of what I've said to be honest applies to many of the Anglophone countries. But I think the best way to determine what applies and what doesn't actually falls back to the question of the leadership of the country. And so for the ones that are democratic or autocratic but stable, that typically will determine the level to which technology can actually change the country. Ethiopia is a good example. Economically doing fantastic. But in terms of technology, because everything is so government-led, you find that it hasn't picked up in quite the way it could have if there was competition. So I'd say for Francophone Africa, for Lucophone Africa, it comes down to, and possibly all of them, it actually comes down to the leadership, to what has a direct effect on adoption of technology and innovation. Okay. If that's all. That's it. All right. Thank you very much. Thank you so much. Please give it up for Mark. Thank you so much.
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The narrative on Africa has long been led and dominated by stories of war, minerals and safaris. While most recently the narrative has shifted into a manhunt for bloodthirsty rebel leaders, a story not too distant from that of tyrannical and oppressive African leadership. Africa, you could say, has an image problem. The African people, however, with their indomitable spirit, their tenacity and their make-do attitude continue to be part of a new chapter in history through innovation, ingenuity and information technology.
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10.5446/21370 (DOI)
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Good afternoon everyone, it's hard to see you, but I hope that we can manage. I wanted to say that if you have any questions along that short presentation, don't hesitate to interrupt me. I have the big pleasure to introduce shortly the Open Cities application challenge, which is, I would say, done by experts from certain areas, being likewise non-experts in other areas. I'm also a professor here from Berlin from the Freie Universität Berlin, and we often talk about this gap between the technical experts and the domain experts. And here what we just do is to get into the area of open data, so where we add to the open source, to the open standards, to the open interface, to the open innovation ideas, the idea of opening the data not only from administration, but from organizations, even from enterprises if possible. And if you think about that idea to extend data and give it for anybody, for any use, then you need to have some tooling to cope with this data. You need to be able to search for the data, to find the data, to analyze the data, and simply we say for that you need a platform. And that platform has been developed by the Open Cities project, a European project that has started last year, last till next year. And one of the contributions of this European project is to have challenges put forward for crowdsourcing for open innovations, for applications based on open data. And that application challenge is about solving urban problems, so to improve the life of the citizens in Europe by using just open data sources from a European country. It doesn't need to be as of now to be open, but along the process of proposing an idea, an application, or prototyping such an application, you're invited to also helping to get hands on this data. So the challenge has been announced already at the Mobile World Congress, and will last a couple of more days. So it's not too late for you to get to know this challenge. It's really open for everyone, for the technicians and the non-technicians. And as we learned beforehand, maybe we are in particular looking forward to work with the non-technicians to get new solutions from individuals, from teams, even from companies, institutions, anyone. And it can be anything you have in mind. So also, it's data and software pretty close together. You can go for any device with which the application can be used. Not only mobile devices, I could of course show the one that many have, or can be computer, but it could be even, I was thinking maybe a Be My application, whatever, right? So be free to think about whatever anti-vice you have in your hand, or in your mind to make use of some data source that can be open and improve the life in the urban environment. So that's a really pan-European challenge, which is scheduled across the cities of the open cities projects together with affiliated partners, plus all other European cities. You are all invited to contribute, right? So what the European cities people do is they support you in launching that application on European levels. So we hope that you can get access to users from all over Europe, that we support you in promoting and publicizing your application to get your pitch for the application and so on. So in fact, once having completed the collection of proposals, we will get into selecting 10 finalists, which are going to get three minutes on stage for the elevator pitch in November 2012 on the Smart City Expo together with other open cities challenges. Not only for the applications, you're going to hear more about it. And then, well, there's really one winner, which is with a monetary award of 3,000 euro, but of course, together with the eternal fame, and that goes for all the winners and even for the applicants because you're going to do something better that hasn't been done before. So you can come up with an application that users already open data, just submit it. You can think about your app that you have already at hand and improve it by use of open data. Or you just have an idea and talk to the technicians, to the project partners, to other partners you have at hand, how to realize that application and please submit it then as well. As of now, you can take use of the open cities data sets. It's more than 700 data sets or some platform issues, sorry for that. So more than 700 data sets from different domains and from the different cities I have shown you beforehand. But please keep in mind that it's not restricted to these data sets. You can take whichever data set at best open and help to open this data set, right? So that is the Europe data catalog that we have established within the open cities projects. So you can go to dataopensities.net and then find the data by city or you can go for certain collaborations between people from the different partner sites. Or you can go for this one here to get back shortly. These are static data sets. So uploaded already on the platform or you can even think of online real time data from sensor networks as for example provided by our partners in Barcelona which have established sensor networks in the urban environments here about bike stations and of course further sensor networks can be used to contribute to this open cities challenge. Time is running. The timeline I said it was launched in March this year. It runs till end of June and we're going to have the finalists round in November at the Smart City Expo. So to be here in Berlin and to have the pleasure to introduce this challenge to you, of course I was also proud that this is in line with other challenges we had from Berlin and Germany. So we started already in 2011 with an apps for Berlin competition which had the finalists at the Always On festival. Then only in March this year we completed the apps for Germany competition and challenge where the winners have been presented at CBIT and well soon we hope to then announce the winner at the Smart City Expo in November. But please keep in mind that the deadline is end of June as of now it's the 59 days to go. I would say for disruptive new ideas it's enough time. So it doesn't need to be thought through till the very end. It can be ideas. It can be prototypes. It just help us improving the urban life. So that's it already from my side. I'm standing here on behalf of the whole project team. You see here the partners from different locations in Europe. Some of them are here so please pass by. Talk to us. I have here also some flyers which you could take with you about the challenges and of course we are all ready to talk to you if you have questions. Thank you very much.
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The re:innovate track highlights different perspectives on Open Innovation. This session presents challenges of the public administration for the civil society. Open Cities "Open Innovation Mechanisms in Smart Cities (Open Cities)" started as EU funded project in the end of 2010. Within the project the participating administrations, research institutions and companies support Open Government activities. The partners from the European major cities Helsinki, Berlin, Amsterdam, Paris, Rome, Barcelona and Bologna transfer methods of Open Innovation -- like Crowdsourcing, Open Data, Fibre to the Home and Open Sensor Networks -- to the public sector and validate the success of the methodologies within pilot projects. Open Cities App Challenge -- Prof. Dr. Ina Schieferdecker Within the scope of the Pan-Europian "Open Cities"-project the Berlin Senate Administration for Economics, Technology and Research supports the open call for the Open Cities App Challenge. This call is directed to all developers and organizations with innovative products or services that uses open data (from the Open Cities open data platform or the Open Cities open sensor platform or any other open data source) and solves a real problem in citizens' every day urban life. Prof. Dr. Ina Schieferdecker presents the challenge, informs about the terms and conditions and calls on to every interested developer to contribute. For further informations check here or the portal. Open Cities Crowdsourcing Challenge -- Esteve Almirall The second Open Cities Challenge that adresses the European audience targets developers and everybody who is interested or engaged in the field of Open Data. Open Cities asks them for their proposals on what kind of data the developers and interested activists would like to see released. This is something that has not been done before and aims to increase the attention and awareness for opening public data. Prof. Esteve Almirall from Barcelona will announce the challenge and presents background, terms and conditions of that call.
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10.5446/21375 (DOI)
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Good morning everybody. This is the first time I had an experience that before coming on stage a gentleman was asking me, take off your earrings and I said, is that the end? And he promised me that's the end, otherwise we were facing a problem. And I'm going to talk about freedom online and not freedom for gentlemen to ask me to take off stuff. Why freedom online? Why matters? Why we must protect it and how we are doing that? That is what is main in my address today. And I know that many of you in this campaign for internet freedom are quite active and please don't stop. We need you. I need you to give indeed the backing for a policy that is focused and faced on freedom online. The internet is the new frontier of freedom in western democracies but also around the world. It's not stopping in Europe. It's not stopping in the developed countries. It is all over the globe so to say. It's changing the politics. It's changing the policies, the economies in the world. And some find that change too disruptive. That it is too challenging and they want to stop it and therefore I need your activity. For we can't afford, we don't want to have that limited speed. But remember how many kinds of freedom we can promote and protect online. It's not only talking about fundamental freedoms like freedom of speech and right to privacy. That is quite clear. But it's also talking about the freedom to innovate. It is also talking about rewarded and recognized for your own bright ideas in the way you think it and you think fit. And the freedom of the internet architecture as a whole. So far more than just a couple of principles. Yes, the internet should be open and yes, it should be free. But that's not the same as being a lawless wild west. And that we have to discuss too. We have recently seen how many thousands of people are willing to protest against rules which they see as constraining the openness and innovation on the internet. And I have deep respect for them. It's a strong new political voice. And as a force for openness, I welcome it. Even if I do not always agree with everything it says on every subject. But that is democracy, isn't it? It is freedom of speech. It is activating a dialogue. We are now likely to be in a world without SOPA and without ECTA. You are hearing it correctly without the two. Now we find and we need to find solutions to make the internet a place of freedom, openness and innovation. Fit for all citizens. Not just for the techno avant-garde like you. And the fact is that sometimes online activities have real world implications. Unlike it or not, people sometimes use online tools to conspire for horrific crimes like murder or child abuse. And others launch cyber attacks to breach or destabilize internet systems. Attacks which increasingly impact on people's daily lives as ever more transactions go digital. I know that this is the tiny minority of online activity. And I know that we can't overreact. As in other fields of life, we must balance liberty and security. The two need to be in balance. But neither can we ignore it. And the internet has become too important to just leave its future to good fortune. That doesn't work. That is why we must recognize rights and responsibilities online for an online world that is an increasingly important part of our society. And today I would like to focus on the future, on the chance for internet freedom to unlock Europe's potential. Increasingly, people are realizing that the web is capable of powering seemingly infinite innovation. And that we don't have to be constrained by the habits of the past but can be released by the opportunities of the future. Isn't that nice? Opportunities of the future. And that whole industries, once based on limitation and control, could now be based on customer focus, sharing and interactivity. Freedom online can deliver that potential to innovate. But systems that are dated, closed or complex can strangle it. What can freedom online give us? For one thing, a huge economic boost, an open internet can power innovation, search productivity, and can put innovation tools into the hands of ordinary, enterprising people. And that's why I'm convinced, ladies and gentlemen, web entrepreneurs are the key to our future growth. And I want to make sure they have the tools to innovate. Web entrepreneurs. Those people can do amazing things if the only barrier was their creativity and imagination. We have no problem at all. But I know there are other barriers. Entrepreneurs need tools to network better. And I'm working on that. I promise you. They need credit and political recognition. They deserve, and a recent Tech All Stars competition is looking for Europe's hottest startup talent. And they need our universities to be innovation hubs. Inspiring, empowering the innovators of tomorrow. And I'm working on that too. And I'm also working on open standards for open markets. We still haven't completed our telecom single market. A recent study showed that this could be costing us as much as 110 billion euros per year. So this year we will engage with European standardization bodies and the industry to determine the best way forward. For standards that mean content providers and operators can get a uniform service offering. Avoid, duplicate charges and exploit economies of scale. We also need to preserve openness of access to internet service, what some call net neutrality. People need transparent offers so they know they are getting what they pay for. They need to be able to easily switch providers or deals if they don't like the service they are getting. And they need to always have the option of accessing the full unlimited best efforts internet if that's what they want. But most of all web entrepreneurs need us to identify and deal with the barriers that stand in their way of their online freedom. Obstacles like complicated and incompatible systems for identifying and paying and licensing like 27 different sets of rule books when there could be one. One single digital market so to say. And all those things can crush innovation and keep bright ideas confined in unprofitable national markets. Because freedom also means that freedom to innovate in business models. One by one different sectors are facing up to new online realities and to the decline of old ways of doing business and the rise of new opportunities. The music sector realized a long ago. Other sectors like audiovisual are now starting to. Our media futures forum is looking at how this applies to the media sector in general. Of course changing for the digital age doesn't mean always giving material away free of charge. But it does mean we need to be open to new approaches new ways to distribute new ways to be rewarded for work and new ways for people to access great online content easily. Sometimes people are prevented from making this change by out of date rules and practices like those on copyright licensing. Other times it's just that they need a change of mindset that they are too comfortable with old habits to realize the world has changed. Either way we need to wake up. We need to smell the coffee. This is why I am frustrated about the lack of progress in creating a genuine digital single market. And if we are really going to help a free internet and help web entrepreneurs in particular we must promote an open culture. And in particular I think public sector data is a gold mine just sitting there. If we unlock it, if we could boost creativity, boost the economy and boost democratic accountability and that is why we have proposed legal changes that will show the way forward on open data. Making data cheaper and easier to reuse meaning more data sets with less complicated conditions. It's not just about unlocking new data sets. It is about promoting a whole new attitude within governments about openness culture online, creating a new fuel for innovation within our single market. And I admit this would in one sense be a relatively modest step. But it's an important one affecting the change to an open mindset and it could be a prelude to the wider work needed on copyright reform. At the moment it is still just a proposal on open data. And before becoming law it needs the democratic scrutiny and approval of the European Parliament and the national governments in council. I'm convinced ladies and gentlemen of the benefits. I'm convinced of the public's appetite for change. And so I'm calling on those institutions to agree. The proposals swiftly and ambitiously. And if you have ideas for how we can make it more convincing to them please let me know. But of course there is another very significant thing we mean by freedom online. It is about freedom to express yourself. A fundamental right and a pillar of a democracy. We must defend it online and off. Last year Hungary introduced a new media law as you are aware. Significant parts were incompatible with European law. Not least because rules about registration and balanced reporting could have imposed heavy obligations on all kinds of online content from online forums to personal blogs. So I pushed for and achieved changes to those proposed rules. And since then Hungary's own constitutional court has ruled that the new law unconstitutionally limited freedom also for the written press. Both the European Commission and the Council of Europe continue to have concerns that this law is not fully compatible with our European norms. The Hungarian government needs to do more and we will follow it. I can assure you. It is an important area. Clearly there are high public expectations for the EU's ability to act. But equally we can only enforce fundamental rights in areas subject to EU law. So we need to think seriously about whether the EU has sufficient powers in this area. In the EU of course our freedom of speech is protected by law. All actions taken place within a framework of safeguards and legal protections as well as a well established political culture that favours openness. And that gives me confidence that problems that arise can be fixed through a combination of legal tools and political dialogue. And as you might know yesterday was UN World Press Freedom Day. A day to remind us that around the world people including journalists and bloggers do not always enjoy the same rights we have in the EU. One example is Enula Futulaya, an Azerbaijan journalist and human rights activist and this year the winner of the UNESCO's World Press Freedom Prize. And he is doing a great job. Indeed many don't always have the right to an open democratic debate nor the legal protection of the charter of fundamental rights nor safeguards like oversight and recourse. In spite of that indeed because of it in such places the right to express oneself is all the more important. And for those who struggle for democracy we just ensure they have a voice. The internet can give them that voice. We saw that with the Arab Spring. The internet alone didn't cause that uprising. It's much more complicated than that. We all are aware. But clearly online platforms gave protesters a means to organize and a harness for the power of a surging desire for democracy. In Egypt the government tried to turn off the internet in a failed attempt to silence this con. Elsewhere the Spotic government used communications technology as a tool of surveillance and repression. We cannot allow that happen. Where countries struggle for democracy I want to ensure there is no disconnect. And we will be doing that in many different ways by supporting those brave human right defenders who work against cyber censorship in undemocratic regimes through human rights guidelines to ensure EU companies play their part and through European and international coordination. There is one final point I'd like to make. And that is about freedom. Too often freedom and security are caricatured in incompatible alternatives. As so measures to ensure one can only be at the expense of the other. In fact the opposite is true. Because there is no freedom without security. These concepts are interdependent and they are complementary. And I may have the legal right to walk down a particular road at night. But am I truly free to do so if it's not safe? Likewise people aren't really going to use the internet freely unless they know they are in control of their privacy. That their personal data will be handled transparently and fairly. And that interdependence is why liberty and security are mentioned in the very same article. The very same sentence of the European Convention on Human Rights. On Wednesday, last Wednesday, we launched our strategy to create a better internet for kids. For me that is crucial. I think we have the responsibility for those vulnerable in our society. Safety is all the more important for the most vulnerable and assuring this is everyone's civic responsibility. And at the same time I realize that the online world can be a great place for kids to discover, to learn, to interact and to create. But only when they have the confidence to freely explore. There are two main strengths to my philosophy there. Number one, we must avoid crushing the openness and freedom that drives online innovation. To avoid collateral damage to the internet architecture. And second, we must acknowledge that we can never totally eliminate risk for children. We can just reduce them. Sadly, children will always face risk online just as they will always face risk like traffic in the real world. Rather, we need simple tools that educate and empower children and enable them to deal with those risks. Just as we do in the offline world, so to say. And I am pleased that the leading internet companies have joined a coalition to make the internet a better place for children. They are working together to develop solutions. To develop solutions before the end of the year to empower parents and the children. And that is my vision for a free and an open internet. At once a vehicle for innovation, a platform for free expression and a place to exercise the liberties ensured through safety and security. And the best thing about the internet is that it is open and intent to keep it that way is my strong belief and my line. Thank you. Thank you very much. Thank you very much. Hello, good morning. Thanks for your keynote. I have one specific question that basically addresses one of the, in my opinion, basic issues that the internet has. That all relevant infrastructures, especially the companies, are turning into monopolies. And for instance, we see companies like Google, Facebook and Apple battling with each other. They all rely on a network economy and they all turn into monopolies. And that the interdependence between, let's say, traditional media companies and those infrastructure companies is starting to become even more difficult. Now all those companies are buying for intents patents left and right and strengthening their monopoly position. And isn't that the opposite of what you are trying to achieve? That's basically the question. Thank you for your challenging remark and question. I'm pragmatic and I'm realistic. I'm aware of what is at stake. I don't need to explain to you with my past, in my first term in office in the commission, I was the one who had to deal with competition policy and I'm certain that most of you are aware that I was not only preaching that I'm against monopoly and misbehaving and abusing situations but that I was also acting. We should make a difference between how a monopoly, quote, unquote, is dealt with. And therefore, and sorry to take a bit more time to explain what anyhow my vision is, we need clear rules of the game. And only saying we don't like the US Google, by the way, Google and Facebook and Apple and they all are global companies with most cases head offices in the US. But anyhow they're global companies and they have to follow the rules of the game. And that is where I absolutely am acting if they are not following the rules of the game. And of course, telecom operators, the incumbents, but not only the incumbents are complaining that they are using their infrastructure. We should, for more than we are doing, also try to be active in the services and in the product that they are offering. I'm not the one who is fearing difficulties. I am the one who is trying to use all the open internet possibilities and opportunities. And what is at stake? And therefore I ask you, give me food for thought. For in itself, we are all aware that the products of the Googles and the Apples and the Facebooks are absolutely preferred by most of the citizens. So quite often people are complaining and when I'm looking, they do have the iPad, they do have the iPhone and they are on internet and they are using the Facebook. So we should be quite precise. What is at stake? And I'm not the one who is blocking services that are taking into account the rules of the game. And so far, I think that what is mentioned, following the rules of the game, and we have to do more, by the way, we have to do more to be transparent and precise in what are the rules of the game and working on that. Thank you. Are there any more questions? I also like to thank you for your introduction. It was quite interesting. I do have one question related basically to the previous one. You just asked for food of thought. So I think if we want to protect the internet and keep it in open place, wouldn't you agree that it's probably the best idea to make sure that there is no single party who can control it? So like in Egypt, where the government was able to take down the internet, I think that shows that no matter who is in control, it's a problem, whether it's companies or governments, there are a couple of efforts trying to basically create an infrastructure where nobody can control the internet. Do you think that is the direction things should take? In general, I couldn't agree more. But again, I'm coming back to the rules of the game. Then those users of internet and thanks heaven, there are quite a number, by the way, I'm still worried about a high number of European citizens that have never visited internet. Can you imagine? I just visited Italy and I got the latest figure. 41% of the Italian population has never ever visited the internet. And thanks heaven, the general figure in Europe is a bit more positive, but still is worrying. It is around 30%. And taking into account that our system with all those new technology challenges is based on that. I can't afford to accept those exclusive numbers in the traffic of internet, but I'm misusing your question. What is at stake that the rules of the game are there? And that it's not only that they are there, but that they are indeed taken into account. And that is a bit my worry. We also are talking about a copyright. If someone is asking me what in your portfolio is worrying most to issues, the role of the copyright not solved yet and not up to date, so to say, and that is connected with the rules of the game and that is connected with what are you accepting in the internet? Is there an authority needed yes or no? Well, we do have some experience in other fields in competition, but also in telecom and so on. So I'm not in favour for Big Brother is watching you if everybody is taking the rule not only for granted, but seriously. But having said that, we should be aware and the other one of my worry is the position of children. I think they are the vulnerable in the whole internet development and that we have to do quite a bit and therefore I'm grateful and looking forward to the result of that report of the 31 CEOs that will deliver hopefully practical solutions for having more trust and certainty. But all in all, and we learn from those countries and you were mentioning one, Egypt, but it is not the only one on the list, so to say there are quite a number. So we still have to be aware that there is a lot of abuse and misuse. It's not only positive news internet, it's also misused by certain regimes, so to say. So follow the rules of the game, for otherwise the game is over. It's just like football if there are no rules or if the rules are just tackled, then the game is not fun anymore. The next question is there. I would like to ask you two questions. Could you go into more detail on two issues. One is net neutrality. What are your intentions to make sure net neutrality will exist in the future? And the second is you mentioned that you will make sure EU companies will play their part in countries where there's struggle against dictatorship. How will you make sure that EU companies won't deliver technologies that enable surveillance in censored countries? Net neutrality. I will start discussions about net neutrality. Let's be clear that we are on the same wave, so to say, or on the same page, and that our definition of net neutrality is there. I follow the rule and I follow the definition of net neutrality, that it is possible for everyone to join and that indeed taking into account that there is a limitation on the capacity that we have to give the floor to everyone, but that there can be a follow in which that is given. We are preparing a proposal and I am absolutely certain that there will be a discussion afterwards and I'm looking forward to that discussion, but there is no special treatment for one and there should be competition. And that is main for if there is competition, it is up to you in your situation if you think that you are not treated in a decent way to just move to another one and that should be possible. So that is answer question one, question two. I'm taking this question to just push on the standardization, for we should indeed make far more global standardization efforts. Yesterday I had a cup of coffee with a minister of the Japanese government and we were pushing again, for we are talking about an issue that is global, it's not limited, it's not ring fence for Europe or US, it is really global. We need to have standardization, we need to be aware that we are losing time if we are doing that and that is giving an answer to your question too. For then it shouldn't be misused by certain companies in saying this is it and that's all that there is, no way. But we also should take into account and taking your question for another love baby, so to say, it's cloud computing and I'm certain that quite a number of you are interested in what's going on with cloud computing. We are preparing a strategy for cloud computing, for my main worry is that if we Europe, if we are not able to give our strategy, our thoughts and our philosophy about cloud computing, then we are in a position, that other ones, that for example the US is dictating how we should follow the line. Don't misunderstand me, I'm not pleading for a European cloud, but I'm pleading and more than pleading, I'm preparing for a huge discussion and a very interesting discussion, what Europe's position is in cloud computing. For me it is a tremendous challenge and it is connected with the citizens, it's not only talking about big companies, the multinationals or whatever, it's talking about small and medium sized companies, it's talking about the citizens. If you just have a cloud locker with you, the only one who have the locker key, then it is also connected with trust, security and with less cost pattern than we are used to. Hello, my name is Henrik, I'm an internet activist and journalist. I'm very happy to see an EU commissioner at an event like this, so thank you very much for being here and touching on so many important issues. One issue that I wanted to get a bit more into detail with is ACTA, because I think there's been a very strong disconnect between the sort of emotions and ways of expressing ourselves from, I think, a Polish blogger termed it, we the web kids, and sort of this movement and what happens on your turf in the EU commission, a language which came from the trade commissioner which seemed to be very one sided if you see it from the other perspective and vice versa, allegations of being undemocratic and I'm very happy to hear that you at least see this movement as a democratic movement. But I'm interested in hearing your personal experience of this process because personally I find that ACTA should have been dismissed solely on grounds of purpose and so I'm interested in how in the future we can ensure processes that hear both voices. Thank you. I was just thinking when you were mentioning I'm one of the web kids, I would love to be at the end of my term in office one of the web mothers, so okay. But then you will certainly face me, then you have to prove and that is, that makes sense. ACTA. First a general line if you allow me. I think that talking about movements and I'm a big believer in democracy, I don't need to explain that, we all are. We are looking forward to far more discussion and what did happen was the big movement in the outside world is facing not only Brussels, all the capitals so to say, but there is a difference in just voting with your feet and with the legal preparation in a democratic system. I'm not saying that one is better than the other, but both need each other. And what was for me and I'm talking on a personal base, what was the most important one is that this was a wake up call for any how Brussels. So it was not anymore, aren't they worried that we are doing our utmost and so on? No, it was knocking the boat and indeed a wake up call. Having said that and don't worry about ACTA anymore, I was quite explicit, I'm certain that when I'm back in Brussels that I will get a message that I was too explicit, but I'm always saying I'm Dutch so straightforward, come on. And I don't need a new term in office. Having ACTA itself, and that is what I'm asking you to think over. So keep ACTA away, but the content of ACTA was connected with this copyright as far as my responsibility was at stake. And I am one of those believers that artists, creators, writers, they need decent remuneration. If we don't give them a decent remuneration, then culture is over to say, and I will never forget that one of the big singers was coming over for a cup of coffee and that he was saying, Nelly, if you don't are aware that we need to get decent living. And he explained to me that he had already a very decent living. So he was not talking about himself, but about his success or so to say. And I'm aware of that. So copyright needs to be filled in and not filled in 10 years ago with that old-fashioned way, but with the new technology in mind. And what I'm worried about, and that is what ACTA is also approaching, but again, gone, but we have to solve the problem that is at stake, and that is the copyright, that we have to find a way in which, talking about a digital single market, so that means no borders anymore, but with talking about music, but also the audio visuals and so on and so forth, we are facing that it's all ring-fenced by the collective societies. Well, if I have enemies, and I can assure you I have a long list of enemies, on that list are the collective societies, and I can't care less for they are monopolist, and we are touching upon that one earlier, that it's not about protecting the artist and the writers and the creators, it is about protection that system, and perhaps it made sense a long time ago, but it doesn't make sense at this moment, and as long as we are not solving that problem, and as long as we are just looking in the real world that illegally downloading stuff is at the end of the day just cutting off the fees for the copyright for the artist, and just talking about Germany, 94, 95% of the artists in Germany are only getting 1,000 euros copyright on an annual base. Well, if we are aware of that, then there's something rotten in the state. That can't be the real world. So, let's fight for that. And Akta is food in the cold hands, and we know that is time consuming, and we know nearby what the outcome will be, but okay, but let's not stop our activity for solving the copyright, and the longer we wait, the more it is getting a normal attitude for it's not anymore, the younger generation that is illegally dealing with that stuff. It is also around my circle of friends, so to say, and I don't accept that, but we are to be blamed as long as we haven't taken the right decisions. So, a long story answer for your question. That demonstration in the streets is a wake up call for us that we are in a hurry, and that time is not our friend. Hi, sorry to bother again, but I can't kind of help but have to ask a question here, because you talk about copyright, and you say, you know, without copyright, there will be no more art and literature and music, and that kind of is a weird thing, because when copyright was introduced about, I don't know, four or five hundred years ago as a measure of censorship, because that is how it started in England, I believe. You would say there has been no art and literature and music until five hundred years ago? I mean, that's kind of a weird thing. I think the fact that you say that 95% of the people here in Germany don't get more than, say, a thousand euros for their creative works per year, and yet there is a huge amount of creative work being created. I think in itself it's proven enough that I'm not saying we don't need copyright, but if it comes to a choice between freedom of speech and copyright, I way prefer freedom of speech, because you know, I think the arts will do just fine without copyright. Anyhow, not everybody was applauding, so don't make the wrong decision that you get the whole audience on your side. Your example of a long time ago compared to now is not completely correct, and of course it's up to you to do that for what we are talking now is with new technologies where people can indeed be far more creative in their own way of just taking an artist's product and not giving a remuneration. I'm happy with, and I'm grateful to your question for it gives me an opportunity to correct myself a bit. I'm not a strong protector of copyright as copyright as a system. I'm in for more creative forms of remuneration. My only, for copyright is an instrument. If you know a better instrument, and by the way, with the technology development talking about cloud computing, there will be for me absolutely certain a proposal where we can tackle the copyright system in a better way than we did before. We see already with initiatives, Spotify, and there are a lot of examples where the industry is so creative that anyhow for the consumer and the connecting of the devices, it is possible to deal with it in a legal, in a proper way, so to say. So for me, it is, I think that everyone who is creative and who is just making something, service product or whatever, that at the end of the day, there is a decent remuneration for that. And it's nothing to do with freedom of speech. I'm a liberal, so I would curse in the church when I would say I'm not in favor for freedom of speech. And I sincerely hope that you got already from my acting so far that I am indeed not shy to act if that is needed. By the way, very interesting, but that is talking about freedom of speech. I asked a couple of wise people to prepare a report talking about freedom of speech. And they are absolutely, four of them, a former minister of justice of Germany, a former president of one of the Baltic states, and an acting professor and a former advocate general of the court in Luxembourg. They are preparing freedom of speech principles, and that will make a big rocking the boat also in the European parliament. For I don't accept any more that if one country is acting, not in line with our principles, that we just say, well, let's find out how we can just protect them. And so it's over. We should be aware that our democracy in Europe is based on principles and freedom of speech is one of a very important issue. So for me, it is not, there is only one way of copyright. Be creative and give us a hand, and the technology will give us a help. But it is, at the end of the day, not a free lunch. We have one last question over here. Hello. My name is Wolfgang Zenges, and I'm one of the co-initiators of the Cultural Commons Collecting Society. It's an initiative to found a new collecting society for free licenses and non-commercial creative commons licenses. And looking at the topics that you considered to look for new ideas in licensing and for copyright, would there be a chance to support such a project from your side, from your bureau? At the end of this session, come over and give me your card and let's discuss it if there is a ground to go on. Yeah. Okay. Thank you. Here is one. Yeah, the last question. Hello. I just wanted to address the copyright topic again because I want to clarify something that may not be clear to some of you, because copyright is not the same thing as the disputing art. Copyright is the right, the artist holds itself, and I think it's correct to hold on to that. But what we need is a reform of ways to distribute art, to make money, to guarantee artists that they can live off their art. And I think copyright is not the problem itself. It's the problem that the artists do not get directly reward for their work. And with your position on actor, for example, I think it is a very important thing to also consider citizens' worries that will come with the introduction of such new things like actor or outside the Europe, CISPA, other things are in the discussions as well. It's a global movement, I think. And I want to ask you what kind of efforts will you, does the EU intend to achieve reform on art distribution or rewarding artists better without taking freedom of speech or installing, for example, a filtering or surveillance system in the Diggleton world? Just make it quite clear and not giving hope for an issue that I can't fill in. For normally spoken, I'm following the line that I can be quite clear in what is within my responsibility and what's not. Copyright, whatever new form and so on is for me talking about a decent remuneration of a product or service that is already delivered. And that is if you are doing something for your living, then you are also expecting that you can earn a decent living out of it. Having said that, what you are touching upon is in general terms what could be done for an artist-friendly climate, if I get your question correct. That's not within my portfolio, number one. And that is not really what is in the portfolio of the European Commission, for you know that there is still quite a bit linking in the hands of the member states itself. So this is far more for member states itself. And I wouldn't touch upon the policy of the German government, neither of governments, for example, my government at home. Having said that, the European Commission is stimulating in the form of grants and in the form of pushing programs for artists too. But that is just a drop in the ocean of the issue that you are counting. But let's first solve the other problem. For that for me is main. And I promise you that I won't rest before we have done more. But I need your help, I need your backing and demonstrations like you did before. Would just give me a hand talking about pushing my colleagues in the college too.
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Internet has been a fantastic force for growth and innovation. Now that it has become a central feature of our lifes, some consider that Internet is too important to be left to its own devices. Commissioner Kroes will highlight that the Internet is an important expression of freedom and that a number of freedoms must be protected on the Internet. This also requires responsibility.
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10.5446/21380 (DOI)
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I've been asked to put the question to the audience, how many people have been travelling here with Deutsche Bahn? Thank you for travelling with Deutsche Bahn. And this was his joke originally. And how many were delayed? One, two, three, four. That's not that bad as we see it here. Okay, thanks for the introduction. And we're talking about 20 minutes about the rail monitor. We do it in two parts. I'm more about how we made it and how it was produced. I'm talking about the journalistic stuff. How you did it at Deutsche. The idea came up last year around this time. First to get the data out of the German railway corporation, Deutsche Bahn. And we first thought about to do a Freedom of Information Act request. And then we came up with the idea to scrape the website from Deutsche Bahn because we were quite sure they don't want to give us this information. But before I talk about this, I show you the video, how it's working. It's one minute, 30 seconds, so you get an idea how this application, which kind of features the God hand stuff, but it's not working with my remote. It now does. We made an English version, I think, one month after the German, because the Guardian was featuring it and we had quite a few international requests about it. So from the German railway website, they give you the information, at least in five minute steps, how late trains are going to be. And so we have a software scraper who's going there every few minutes for every train, which is on the tracks, and we get the information that, for example, it's 40 minutes late, and what's the reason for the delay. You can explore this in real, more or less in real time in this application or can go back in time and play it if you want for half a year. I think we got it from October 2011. You can filter the request for which train number, what kind of train type, is it a fast overnight train, for example, or the ICE, which is the fastest train, and can request it for which ranking for every train station. So that's basically how it works. And the scraper, the data we get from the website of Deutsche Bahn looks more or less like this for every train. We are scrapping, we are only scrapping the long distance trains, and that are about 1,000 a day, because I think Deutsche Bahn has about 25,000 connections every day if you have the local trains and S-Bahn, which are in the cities, the transportations. And the difference to the website of Deutsche Bahn is Deutsche Bahn only displays the next delay. They forget the delays before. So you can't do research on the Deutsche Bahn website about the delays from the day before or even one hour ago. So we collect for every station the delay, and so we have a huge data set now about maybe 300,000 connections, more or less, I think. In the beginning, the scraper was quite bad. It was not really functioning very well with the website of Deutsche Bahn, because this is a monster, and looks a little bit like it has been started up before the World Wide Web in the 70s, and it's changing IDs and stuff. But if you're interested in this, you can talk to our coder about it. He's heavily to talk to someone about it, because he's quite traumatized. That's what we now have for every train, a long-distance train, at least. And to get an idea what we have, what kind of data we've got, we first made some dive into the data. This is, I think, it was from August last year. We had about one month of scraped data at this point of time. And what you see here is the causes of delays. So how long it, in average, you have to wait if, for example, it's bad weather. This is about, if this is the cause of your delay, it's 60 minutes around about. And so we get an idea of what we can do, what we can tell with this data, because this is the second part of what we call data journalism. You have, first you get data, and you get more and more data, and then you get an idea what kind of stories are in there, and how you can tell them. And then we, it's, I call it, for me, it's like a process of writing an article, but we don't, we're not writing it with words, but with software. We're designing an application, we're designing an interface, and that's how we're telling the story. And when you write an article, for example, you have a story arc, you have an introduction, you tell your points, and then you have an end where you come to your conclusion, for example. You don't have this when you're designing a data journalism application, as please, I think so. You have a beginning, that's when the people come to the website and have the first impression of your data journalism application, and the best thing would be they understand it without any explanation. They know what to do with this application, so it's a lot about how to design the interface, the user interface, and of course the usability, how people can interact with this. But as I said before, I think there are a lot of similarities to writing an article, a story, but you're not using letters to present it on the screen, but you use symbols, you use UI elements and stuff. And here you see how we, our designer, who started to think about how to present this, how to design this map, what people can do to interact with the data, got ideas how people can interact. And I think the secret of a good application is to throw away at least 70 or 80% of the features you think an application should have. Because we had much more ideas what you can do with data, for example. Here we said we can integrate a visualization how the delays are developing over time. And we had a kind of certain budget, and it means we had a certain kind of time, and you have to throw away things because you don't have the money to develop them, and many are very confusing for the end user at least. Because if you're deep into the development of an application, you're very into the subject, and you know everything and every secret of your application, know how to use it. But the best is to take somebody who has never seen it before, sit him or her before the computer and let him or her use it, and just write on a piece of paper what he or she is saying about it, and you mostly learn they don't understand a lot of things, not in this way you thought they should. In the end, we came up with this, more or less with this design, which was in the end implemented. We had a lot of problems because of the torture wanted to have it in HTML5, which means we are not because of the iPad, because of the bad, bad iPad, and that means problems with Internet Explorer 2, which many people are still using, because up to Internet Explorer 9, it's a problem about JavaScript. Actually, it didn't work. It's a title and many workplaces. Yeah. Because they are still using IE7. So I'm happy in two years or so there will be no Internet Explorer 8 or 7 anymore, I hope, and then it's much more easier to develop cross-browser applications and cross-platform mobile and stuff. Mobile means you have to think about touch interfaces, too. It must work on a desktop PC or on a touch, using with touch, so it means, for example, don't make the buttons too small. Can you use a swipe, gestures, and stuff? Okay. That was the design in the end. Then we had a prototype for quite some time, which looked, I think, until three days before we launched, it looked like this, and then we had reworked the map completely. But it was when we had this, I think we had it in winter, we saw the first time this small and like little ants crawling over the map. It was a kind of huge moment for us because we first saw now how the application came together and how we can tell the story about it because now I think we're seeing now about 200 or 250 trains at once on this map, and you get an idea of the logistics of Deutsche Bahn, what they are doing every day, and it's quite impressive, I think. They want a lot of money for this, but they're doing quite a good job. In the end, we came to this kind of application, which now runs for, I think, six weeks and eight, and maybe a last technical thing about it or what has been important for us was we knew when we launched this application that a lot of people will come at once. That means we had a system which can deliver the data to display on the screen of every user, had to be delivered very fast. You have to optimize the data, you have to reduce it, and we were able to present now the data, you can more or less without any hesitation, you can just scroll through this time. These are things I think journalists haven't to, it's about the experience, how to interact with data, how fast you can deliver the data to the user. Before that it was text or maybe a photograph or then video, and now you have to deliver data as a part of journalism. I think for me that's the really interesting thing, and where's the fun in this, to do software development as a kind of journalism. So I give over now to Stefan who gives us an idea about the process at your paper. Yeah. Well, why did we do this? Germany's biggest broadsheet newspaper, and well, we're not actually in the software programming business, so we were quite happy when in July 2011 we met at Mezwerk Recherche Jarls conference in Hamburg. Well I was always interested in the stuff Lawrence was doing and his team was doing, and we were just chatting what we could do together, and you brought up the idea of there's this thing with train delays, and everybody's interested in train delays in Germany, and why don't we scrape Deutsche Bahn website. Well, my very own personal fetish is logistics and trains and cars, motorways, and so I'm really interested in this as a person, not as a journalist, and well, there were two things combined at this moment, and I said to Lawrence, well, why not try this thing out and talk about nine months from then on. Yeah. Just to give you, of course, the idea to visualize train data live or in the web is not new. Like Swiss trains, for example, was an inspiration for us. We had Stiftung Warn test, which is a consumer, what is it? Magazine. Foundation. Foundation who's testing stuff. They made a feature last year in spring. We learned afterwards they did the same thing. I think they scraped the website for one month or so. Or did it more or less classical print product article about it with visualizations like this, and then in last autumn, a single guy in Germany started Zugfinna, which is about basically doing the same thing as train monitor. When I saw this, I was getting the idea that there could be a story in it. Well, I like data journalism, but I always think there's got to be a story in it. Now you see how many pieces we did with the data that you guys scraped for us. It was about a dozen, two dozen stories we could extract of this data that's never been mined before. Well, there's some interesting things like the high-speed train network in Germany is the part of the network which has the most significant delays. Deutsche Bahn knew that, but nobody else knew that. We could scrape. Actually, there was it. You saw the red lines. This is Germany's high-speed railway system. We looked at the data, and it was quite complicated to look at the data in this way, but we got out, okay, this is the single most delayed... train connection in Germany here. This is between all the big cities. This is a good story, actually. We knew what to write. But this came after, well, half a year after you really started, after you really scraper really worked. So this was not that common for us to say, okay, we are going to invest a lot of money in you guys and you're going to do the scraping, and we don't know which story will come out. We didn't know until March of this year what story would come out. You started scraping in October. In March, we began diving into the data in a really very statistical way, and I had to think about all the things I learned at university about statistics and when are things significant and how many connections have to be counted until something gets significant data and so on. And in the end, we had some very good stories. Well, there's been the highway, the high-speed train links are a problem. We got the story that Deutsche Bahn isn't telling its customers the full truth about delays. We found some very serious bugs in the data. Like Deutsche Bahn says, when the train is late, seven minutes, they say it's five minutes because they want people to arrive at the train station in time so they don't have to wait and things like that. Never heard that before. There's been some clues. We got out of the data and our readers really appreciated that. We tried to get the print edition of that day in March. We published all that. We made all two pages, broadsheet, panorama, and the paper with four big pieces about what we found out. It was also very good cooperation between the online department, I'm the head of the online department, and the newspaper. It isn't very common in Germany these days. Well, it was really a good cooperation because our print Deutsche Bahn's expert confronted Deutsche Bahn with the findings we made. We made actually some very good stories out of it. We did publish the data. This is Google Fusion tables. You see everybody has access to this data we were working with and can do some sorting himself. We made an API, not we did, you did publish all the data as an API. Now we are experiencing that it doesn't stop with our stories and our coverage of this thing, but some people out there are working with the API and doing an iPhone and Android app. Some other guys did, one guy is trying to make a prognosis of how late is this train going to be based on what we got here. And they are all reading this stuff that is in the API. It's quite complicated. For us, the interesting thing was that we really learned a lot about data journalism. We didn't do that before. We were quite happy to have you on board as we wouldn't have been able to do that alone. It's really a big newspaper trying to get things right in the digital age. And it's the first project. Of course, now we are planning a second one and a third one. And we are trying to do it alone because I think as a newspaper we have to be able to do these things alone and to have all the knowledge in our house. For me as editor-in-chief, it's one of the best things of this is that everybody at Situatio now really understands that there is stories in data mining and data journalism and you can get ahead of the market by doing such stories and not only classical stories. Yeah. Well, I wanted to say something about the open data aspect on this. I wrote there that it's the same open data because for us it was the first time and I think not many people did this before a kind of real-time data journalism. That means we are providing now the data we are scraping more or less in real-time to other people using the API, the application programming interface. And we are not allowed because we are scraping the data from the Deutsche Bahn website which I think it's a public body. It's owned by the people in Germany. So they are obligated to do it themselves. They don't do it. So we did that for them. But we have not the rights to say you can reuse it for commercial purpose. I think it would be problematic. So we said you can reuse it but only for kind of research, for testing and not to sell for example a mobile application. But what we are hoping is that we give inspiration to Deutsche Bahn to open up there or to give to provide an own API because we think it's a huge opportunity for them to be transparent. And I think we would see great services built on this API. And as you told before, the one application for example they give a prediction about what your delay would be probably. We have half a year of delay. So we can say if you are traveling on Friday afternoon, you are probably going to be late seven minutes on this particular train. So we had more ideas I said before. We killed a lot of features to make it not too complicated. Yeah. I think we get signals that we shouldn't delay the program ourselves. Thank you for listening and traveling with us. And maybe we have time for two questions if somebody interested to put some. Oh. So much. My moment. The other one needs time. The other one needs time. Thank you for presenting this very interesting project. My name is Marianne. I want to know what your agenda with this tool is now. Now that you are running this on the URL, are you just waiting what happens or do you have any concrete? This is also interesting for a newspaper that you are programming a tool, a guy's programmer tool and you have to maintain it. Yeah. We are planning to maintain it. And perhaps if Deutsche Bahn is rethinking its policy concerning giving data to the public, we would adapt the tool or something like that. You constantly develop this. That's the point and we get no real budget for that, but that's another subject. What kind of feedback did you get from Deutsche Bahn? Well, we asked them before we published the articles. What they could tell us about where we found out. And they answered the questions. That's all. There was no problem at all. No problem at all. The only contact to the Bahn was before the publication of the article. And after the shift on variant testing, I think they got it that there are guys doing the scraping. I think as they are following a transparency policy as a company, it wouldn't have fit in their strategy to sue us or something like that. They didn't do that and they didn't react badly. So we didn't expect it. It was kind of an experiment. Did you release the scraper? I'd be interested because the software that Deutsche Bahn runs, runs worldwide, pretty much as far as I know. So I guess a bunch of people would be interested in that. You'd like to hack all of them. It's a quick win. I went. Just one last. Hi. Sorry, I'm quite high. What feedback did you get from your print colleagues? They were amazed. The return on invest? No, the return on invest wasn't the thing, print colleagues don't think about that. They were quite amazed because they never did anything like that. They were getting what digital journalism could be in the end. This is something everybody got to know in our big tower in the East of Munich. They looked at it and it's fun playing around with this thing. There's a panorama page in the paper. So really everybody got something out of it. They got the clue that there could be more than text and video and all that. Did you ask first for the data? No, not really. It's easier to ask for forgiveness. I'm going to take over here. Thank you. Hi. I'm Peter Kohlberg from Belgium. I see a lot of similarities between the German issues and the Belgian issues. We also have a railway company and they're also not that polite towards open data and stuff like that. Thanks. We started IRL. IRL is not for profit organization. Why is my slides not? So IRL is not for profit organization that focuses on transport data in Belgium. So who am I? I started recently like two months ago, started the Open Knowledge Foundation Belgium. We're trying to stimulate open data this year. I have a start-up. I'm not going to make publicity here, but we're the best real-time digital signage company in the world. So if you want to buy screens, come to me and I'll sell you everything. And everything that we do right now starts with our first NPO that started two years ago and it's called IRL. What happened? Well, in 2008 we had a mobile website, just a simple scraper, just like the German guys from Zugmonitor. And yeah, we send a letter, a nice letter to the SNCB or the NMBS, the national railway company of Belgium, stating that we just did this. It's easy to access on iPhone. It's something they lack because there was no such thing as a mobile website or let's say an app of some kind. But then two years later we got an answer on this letter. The letter was from the biggest lawyer company in Belgium stating that we had immediately to stop with everything that we were doing. We had a site with 30 visitors a day which made it possible to access the railway data on your mobile phone. And yeah, we just published this season the CIS letter online. This is what happened, both the Dutch people and the French people in Belgium published about this and the biggest newspapers that IRL has to stop. So let's give some context because Belgium, yeah, we're like these neighbors from there somewhere. But we're pretty much divided. We have the buses, we have flounders, we have Brussels and we have Wallony and each of these three regions have their own company. Clear? This is simple I think. And for the railway company it's even simpler. We just have one railway company. This was a problem to, oh wait, yeah, it's all these different organizations have to listen to different governments. We're maybe a little country but we have six governments. When, yeah, well there was a time that we didn't have a government or they told people that in foreign countries. But this wasn't true. We still had too much governments. So these four companies listen to different governments and each time you want to make the open data statement you will have to go to different governments. So we went to the Flemish government and now at this point they're already publishing or have a statement for open data inside their stuff. The Brussels government has already published open data now. The Wallony government don't even bother. The federal government is also working towards open data right now. But we also have some pressure from Europe and in 2005 we had to split the Belgian railway company because we only had one. This was a good point I thought because we only had one organization to go to see, to have a meeting and then to convince to do open data. But now we have the railway maintainer called Infraball. Then we have the organization that works with the trains, that drives the trains. This is a European decision. Everyone in Europe should do this. And then we have a third company, the holding. And these are talking to both of these or should be talking to both of these companies and with the government. So these are the three CEOs of these three companies. And we talk to all of these three companies. This takes a lot of time. And we talk to these guys and they say open data, this is awesome. Let's do this because then we have bear cells. The second one says, okay, let's do brainstorm sessions. And we've been doing digital creativity in brainstorm sessions. The problem, these guys don't have data. But they like open data. And that guy over there, that's looking like this. He says that all the data is from him. And no one should even bother asking for data. Not even this guy. This is the big buzz. He doesn't receive data from that guy. So it's not a problem of open data. It's even a problem of internal structure. IRL. We started an organization, a living lab. That's a cool word just for something that takes frustration from people, uses the not-for-profit organization, puts it into ideas, and maybe projects come out. These projects can fail. We had some projects that were really bad and people put some time in it. But whatever, these failed and these went back to frustration. Then we had some good projects, which actually some spin-offs were created from that. So, after four years of frustration, we're still online. This is a big point because we had a lot of lawyers asking for explanation and a lot of politicians do which ask for explanation. And these were all in my reexaminations. I'm not the best student or I wasn't the best student in the world. So I had a lot of reexaminations and I was doing these projects and I got sued and other stuff happened and I had to talk to politicians, to these companies. And a conclusion I did some extra years. At this moment, we have 30 active volunteers. We have 12 maintained data sets on data.IRL.be which is a restful API which publishes dynamic data and we have four spin-off projects. So the goal of the NPO, the Not For Profit Organization right now is organizing events, doing community building and we have some events like that like IRL Summer of Code which you can, which gathers students to work on these 12 data sets that we were talking about. These 12 data sets are about buses, trains and so on. Then we are maintaining and financing the data.IRL.be restful API. We are incubating startups, Flat Turtle, this is the company I was talking about before. That is digital signage. This uses data from inside the IRL NPO. First site is a dating site. That is a dating site for train users. So you can go to, you are on a train in Brussels, you see a pretty lady or a handsome guy. And when you get off, and you have been talking or not, when you get off, you just take your laptop, you say I will go to the first site. Oh, I saw a beautiful lady or a handsome guy with a brown jacket with a red scarf and maybe you will get back in touch after a while. We open data is now a startup which gathers data, open data or close data, inside an arrestful API to four third parties. Gandetta is a game in which you have to conquer districts from a city by just doing four square check-ins. And now we are taking this project to the neck level by adding mobile or transport information to it. And last but not least, we are a copyright management for free Libre and open source software. And we have a lot of volunteer projects. We are all doing this open source and you can go to gethub.com slash IRL and you will see all the software projects. So that was the IRL NPO. Thanks. Are there any questions? Meanwhile, I learned that heiser means husky in English. Is that right? I'm still heiser. In addition to your great entertaining presentation, there was a similar case in Berlin, some app developer developed an app for Berlin. It is called that app and he got problems with the Berlin public transfer authority as well. They forbid him to use to scrape the data and it was quite funny because they were so stupid to forbid an initiative like that. Maybe it's interesting because it's so similar. Yeah, indeed, we work together also with other people who do open data, open transport data, being non-official people. Like in the Netherlands, you also have something similar like Open OV and that's one guy who just opened up the entire country. This is amazing. And you also have a lot of different projects. Thanks. Another question? Okay, thank you. Okay, and now, to the end, Stefan Wehrmeier tells us about global public transport data. Thank you. After we've seen now two case studies, one for Germany, Deutsche Bahn and one for Belgium, I'm just going to give you a broad overview of what kind of public transport data is available in the whole world. Because there are more places that have public transport and if there's one company that is supposed to get all the data, of course, it's Google. And I don't know, most Germans don't know that probably, but if you go to Google Maps in some country that supports Google transit properly, you can not only see public transport lines on the map, but you can also do routing. In Germany, you can do routing from A to B with a car and you can walk. But in New York and many other places in the world, actually, these places, you can also use public transport routing on Google Maps directly on the map. Perfect. Because why is that? They get the data from the public transport providers. And the first step to do that was actually to define a format, the general transit feed specification. It used to be Google transit feed specification, but they changed that to be more general, I guess. And now this is a format that encompasses the locations of stops when a bus is coming, where is it going, and all the times in between. And so public transport providers can publish, they can create this data set in this format, give it to Google, and then the users can use it on Google Maps in the area of the public transport provider. A really neat idea and it works in many places. These places, perfect. But it doesn't work in Germany. Why is that? Because Germans, we don't like Google somehow. I mean, we don't like Street View, we don't like to give them data. And this is exactly the same problem here. The problem also is that if Google gets the data, they actually make a contract with a public transport provider about this data, and the data is not necessarily available for all. There's a site called GTFS data exchange, GTFS general transit feed specification, and this site collects all data sets in this format that is publicly available. So if you're a developer, check this site out, gtfs.dataexchange.com, and there you can download massive amounts of public transport data, unfortunately not from Germany, because we don't like it. We don't like open data in the public transport sector, unfortunately. But many other places like it. So we have seen here, the US is full of it. Basically every major city publishes data about public transport, and in Germany, we are lucky if we get the routes on Google Maps, but the data is not available there. So how do I come to this realization that there's so much data? Well, in 2009, I saw Maphummental. It's a project in the UK, where you can say, OK, this is basically my postcode, and how much time does it take me from which area to get to the central location? For example, if you want to arrive at the center of this dot at 9 in the morning, you can travel from around all the highlighted area. Really nice project, and it doesn't only work for London, as seen here, but also for the whole UK. So what I actually had just the brilliant idea, as I saw the TSUK monitor, I want to take this data and try to make something like, OK, I'm in Berlin, and where can I go in like five hours? Can I reach Dresden? Yes, of course. But can I reach also Hamburg? Yes, of course. But can I reach Düsseldorf? Maybe. And then you can see, OK, I have a slider, and now from this position in whole Germany, that's the next thing I think I'm going to try out. The problem is the data is not available. Maybe the data is available in the API that the Zutorch people talked about. But what I did is I scraped the data for Berlin, and if I had a network here, I would actually show you how it works. But it's called Mapnificent, and you can put your dot in the middle of Berlin and move it around, and it shows you how much time it takes to get around Berlin with public transport. You have a slider in the lower right corner, where you can say, OK, 15 minutes, 20 minutes, and then it shows you immediately how far you can go in that time. So what is it useful for? Well, I did it not only for Berlin, but also for San Francisco, Washington, New York, Los Angeles, Chicago, Miami, and basically a lot of other cities, and why? I just need to, because it's cool. I just wrote one program, and the data is available, and I just need to put more data into the program, and it just works. So this is like the power of open data and of open specifications that you just have to write the application once and run it with data from anywhere. And yeah, I'm really happy that it works so far. But as you can see, the US is overrepresented, and Europe is, you know, we have something in London, some parts Spain, France, even Italy, but Germany, the Berlin, the Boudot, I scraped myself. There's no open data for that. Anyway, so what you're going to do with that? I made a printed map. I actually thought about printing nice maps. You can just hang it in your home and see, OK, I have to go to, for example, Charlottenborg, how much time would it take me, and then I can see how the color is green. OK, that might mean 20 minutes or something. And yeah, I actually want to sell these maps, but I can't sell them for Berlin because the data I scraped, this data is actually not scraped, but under some weird contract from the BBG, and yeah, I can't sell it. This is really a problem for me. And I'm also a thought about here. This is also a nice project. I actually want to show a demo there, too. Can't do it now. This is from the Netherlands. They have one train company for everything and also one ticket, and here this is a nice visualization that shows them how far can you also go, but it shows you by deforming the Netherlands, actually. So the Netherlands is actually not that shape. I hope you see that. But it's actually transformed to form a circle so that you can see. Each circle represents, I don't know, 20 minutes or something, and it grows, and you can see immediately how far you can go. Actually the same thing for Berlin, and unfortunately it doesn't morph the shape of Berlin, but you can see, you can click on stations, and it shows you on a radial scale, basically, how far, how fast you can get to other stations. So for example, if you click on something like pregnancy or POTS-STEM, everything moves far out because it's far away, but if you click on Fridtisch-Stars, everything moves closer to the center because from Fridtisch-Stars you can get anywhere really fast. So it's also nice for mobility planning. This is a project I'm currently doing for Brandenburg for a planning company there, and they have like the youth in Brandenburg is really in a bad place because everybody is moving away from Brandenburg to Berlin probably, and the mobility situations there are really bad. So this is basically the situation. If you're at 7 p.m. in the evening, and you want to get from Pritzvark somewhere else, all the red parts are stations you could usually get to, but at 7 p.m. in the evening, you can only get like two other stations basically in this image. There are some more down there, but so you can have a nice visualization that the youth in Brandenburg has a really bad mobility planning, and it needs to be something to be done about that. So lobby work with these images makes it easier to understand how good the situation is. And I'm thinking about doing a startup that actually uses public transport data to bring that to more fields because public transport data is actually not only for going from A to B, but also can be used in many other contexts. For example, apartment search, where can I live so that I only need 20 minutes to work and 30 minutes to my girlfriend? So this is actually a really complex query, but it can be done with public transport data. It can show me the apartments that are available in this area, because it's not because it's like three kilometers away, but it's maybe just five minutes away. So time is really more important in this context, and public transport data can convey that. So my general theme here is there are lots of undiscovered possibilities. I hope I've shown you some things you haven't seen before. And the best app is the one that someone else builds with data. Someone else has opened. And I hope we see more open data, especially in Germany. Just two days ago, I was at an event from the Green Party and the VVG and the VVB were also there, but they weren't so happy about public open transport data. And yeah, maybe it will get better at some point, but there's still lots of lobby work in Berlin and in Germany that we have to do for that. But I'm still very hopeful that we see some good progress there in the future. All right, thank you.
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Millions of passengers use Germany's railway system every month - but which trains are often running late, what are the structural problems? Doing an interactive piece about that complex network is of great worth for both journalism and society. Stefan Plöchinger, editor-in-chief of Süddeutsche Zeitung's online news site, and Lorenz Matzat, co-founder of OpenDataCity, give an overview of the project: idea, process, obstacles, working with data, doing journalism with data and reactions. Pieter Colpaert will talk about Informing commuters in Belgium In 2008 our not-for profit organisation created a simple mobile web-app to look up train schedules, called iRail.be. As no other mobile app existed, this became a huge success, until we had some dispute over copyright in 2010. In 2012 our servers are still up and running, we started a legal structure supporting 30 volunteers, and we are promoting digital creativity using open transport data.
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10.5446/21381 (DOI)
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Thank you very much, Sandra. Hello, everybody. Good morning. I'm Susana. And I'm a former journalist myself, who got very frustrated 10 years ago from jumping from one story to another. Plus, I live in a country where bad things are happening. So you find it really, really hard to adhere to this basic journalistic principle not to get involved and remain at a certain distance, because journalism is about reflection. So I decided to found a watchdog organization that used journalistic skills, journalistic analytical investigations, and started to hunt the bad guys. We disclosed concrete cases about their misbehavior, about how they misspent public resources, how they were corrupt, or involved in illicit practices. And we used these concrete examples to drive a public debate to reform politics, to diminish space for corruption, and to just make society better as we hoped we would achieve it. As Mr. Kennedy, I've been also in Berlin, not that I would like to see myself as a piece of pastry, but as this charming mistake, I also come from a country, which is Slovakia, where in 1989, the walls started to crumble and eventually fell down. It was a time where enthusiasm flourished. People celebrated their newly gained freedoms. They celebrated that they could freely vote and elect their own politicians, and they were full of hopes for a better country. While people were celebrating, there were very powerful networks being formed in the background who saw this change especially as a way to gain profit, as a way to see possibilities and opportunities that normal citizens couldn't see at that time. They were able to look up front and they were able to anticipate what would be coming, a large privatization, a large amount of state property that were held by the communist state up till that moment, and they all wanted a piece or a share of this wealth and property. So they formed a very powerful networks, which gave them incredible advantage. They had control over public institutions, they had control over judiciary, they had very close ties to politics, which came with resources, it came with money, and it came with the power to form legislative frameworks and to take decisions in the name of the state. On the other hand, citizens, they didn't even know what was happening. When all these privatization deals were being set up, where all the plans were being formed about how to use gaps in the legislation, how to use context to politics to gain wealth, the citizens were not prepared to be equal partners in the debate. How can you be an equal partner in a debate when you don't even know what is happening? So information and open government in my eyes was really a game changer in a country that I come from because it balances power from the networks, from the powerful networks, little bit on the side of the citizens. When you know what is going on, when you can read documents from public administration, you can see traces and tracks of deals, you can see traces and tracks of relationships, and you can start being a partner in this debate who is much more powerful. The very charming thing about watching the state or working with the state is that public administration is all about bureaucracy. It's so bureaucratized that there are written rules for everything. So public administration really leaves tracks, leaves written tracks in documents because you have very detailed rules, set of rules and legislation for processes like public procurement, privatization, signing a contract with the state, prosecuting somebody, et cetera, et cetera. All these decisions have to follow certain written rules but also have to be written down and stamped. So by studying these documents, you can really discover a lot of stories behind, a lot of human stories with great impact. Corruption, nepotism or clientelism are usually phenomena that also come with rule breaking. It is really hard when you want to give an advantage to a certain person who should win a tender or privatize a property, not to do it without damaging other competitors or not to do it without breaking certain rules. So these are all factors that come in handy for citizens as me who are really trying to watch the state. But the most important challenge for us is really this power as an advantage to certain networks and certain groups. So how do we change it? How can we change it as citizens who don't have that money, who don't have those resources and who often don't have these capacities and don't have institutions, public institutions that are actually working for them but often in countries like Slovakia, the public institutions actually work for these powerful networks. What we discovered as an organization is that it is really, really hard to change politics with giving it good arguments about why the legislation should be better, why the politics should be more transparent and open, why politicians should be held accountable. When you produce research, when you produce good arguments, it is usually very hard to convince politicians because they have a certain advantage that they don't want to give up. They just don't want equality for everyone because suddenly they lose this advantage of getting tenders for themselves, getting privatized property for themselves, influencing judiciary or influencing state institutions. So how do we do that? We have to figure out the way how to change the reality for the players, how to make them feel damaged because only if they feel damaged, if they lose in a certain way in real life, if they feel the effects of their wrongdoings, then they start to change their behavior and they will be much more respectful to the frameworks and to the legislation. And I will show you concrete cases where we succeeded to do so in Slovakia. The second thing we found out is that it's always very important to exert pressure. Without pressure, politicians are not listening and they don't feel a need to propose solutions. So what I really believe is in power of examples, of concrete cases that make or that change talk about corruption from something abstract, something that doesn't touch our daily lives to something very tangible, very concrete. So this is my first story. In 2007, there was a notice board on the first floor of our Ministry of Construction and Development which carried an announcement about a huge tender. This tender was 110 million Euro big. It was a nine-year contract that was supposed to bring contractors this huge piece of business. It was published, the announcement was published behind closed doors and not surprisingly it was awarded to people who were very, very close to one political leader. These people started to fill the contract. They started to get the first money from supposed services that they delivered to the state and nobody knew about it. For a year and a half, nobody knew what was going on. Then journalists published information that this contract was awarded to people closer to a political leader. That it was published only on a notice board with an ministry, so no other competitors on the market knew about such an example, but nothing happened. This report brought no political response, no public response, no pressure whatsoever. So we as an organization decided that it would be very good to look closer into this tender and we used freedom of expression in our country and open data and started to request all the information connected to this tender that we could think of. So we requested contracts from the tender, we requested invoices, we requested proof of delivery, we requested all kinds of other documents that were possible and we decided to publish them online. What you can see here is a piece of story, a new story that was reported about these scandals and on the left side you can see four prototypes of logos that were developed under the contract of this tender. These logos were 33,000 euros each and they were supposed to be produced during 2,188 hours. These companies reported that they were working on these logos. This was only one example of a scandalous money that was requested under the standard from the state by the winning bidders. Another example came with very overpriced commercials in media, trainings that were never delivered or trainings that were attended only by one or two state officers, etc. etc. We produced our own findings. The information, detailed information was also published online as you can see on our website. When you go down, you can read through all invoices and you can open anything that interests you. All this information brought a very big change. Suddenly from the quietness, all the media started to go through these invoices with our help and they started to report daily on the scandal. So politicians suddenly couldn't look to the right or left without having to react to this tender and having to respond to questions of journalists. Very concrete questions about logos, about commercials, etc. etc. So the pressure in the society was slowly building. The tender became a way to talk during the television talk shows. It was made fun of by commentators. It was made fun of by famous people on television. So very soon the whole country knew that something was going on and the politicians had to really respond. Thanks to the analysis of these cases, we also had enough arguments to go to the EU commissioner responsible for EU funding in member states and we could also go to Olaf and present them with a very detailed report on what went wrong. Olaf picked up the case and started their own investigation. European Union exerted another pressure on Slovak political elite and very soon the minister had to resign. The contract was cancelled and European Union refused to cover the money from this tender under EU funding. So there was a very concrete damage that suddenly this powerful political network felt. They were prepared for getting a nine-year contract of 110 million euro to perform such a huge contract. You have to organize really well. You have to set up offshore companies around the world who would help you to wash the money. You have to involve tens and hundreds of people into the operation and suddenly it's gone. Suddenly the business is gone. So they felt the damage. What also this scandal helped was that it empowered citizens and media with concrete open data examples that helped them to set the agenda and to exert pressure on politicians. And because the politicians knew that it wasn't enough only to cancel this concrete tender, they had to come up with solutions and proposals. So what they did is that corruption became one of the main agendas for the next coming elections, parliamentary elections, and the new government who came out of these elections had to also propose some systemic changes into the country. And one of those were that all the contracts closed between private sector and the state will be published from the beginning of 2011. And we really do have a governmental website that publishes every single contract that is signed by the state and private sector. So we will not again find ourselves in such a situation that we will not know of a powerful contract in the background, but we can monitor these contracts when they are being signed and when it's in the early stage of development. You can ask afterwards, okay? So this was an example where such a concrete case produced a very big change in our society and gave power to citizens. But sometimes open data doesn't really carry concrete elements of corruption. It will not provide you with the concrete evidence of who took a certain amount of money from whom and how it was washed through circles of shore havens and etc. But open data is too corruption in my eyes what accounting was to Al Capone. It doesn't produce enough evidence to put somebody to jail, but it often produces enough evidence to see that something is really, really wrong and get the debate going. So sometimes it's really about realization that your ambitions can't be too high and the society can't be changed overnight, that it's a longer process and what is really important is to start to get the debate going on in a country. So I will show you another example when we started to analyze another tender for cleaning the roads in Slovakia and washing the snow. We started to look into different counties and see what companies in these counties proposed. What you see here is two pieces of paper that two companies submitted for two different tenders. Both of these bidders were proposing that they will clean the snow from the roads on two different places and these pieces of paper were supposed to confirm that they really own or that they really rented a mechanism, cars, that will allow them to clean the roads. But when we looked closer and you see the details, this is a detail from the first paper and the detail from the second paper, we found out that the two companies are actually putting the same numbers of car plates. So one company in a city A was saying that it will be cleaning the roads with the same mechanisms as the company B in a completely different city. So this is how they tricked and cheated in the tender. So this piece of evidence wasn't carrying tracks of corruption, but it was enough for us to report this, to get attention of the media and to get another huge tender and contract cancelled by Slovak authorities. So this is an example where open data can really empower you to set the agenda, not to get somebody to jail, but at least you save public resources by having a certain contract cancelled. Open government was, as I said, a huge shift of paradigm in our societies. It happened in legislation, but it happened in the, it didn't happen in the minds of people. So for example, this is an example where we requested information from a register of visitors at the Ministry of Education. We wanted to see who is coming to the ministry and who is visiting ministers. And this was the official answer. We got a photocopy of the front page and the back page of the book and nothing else. So this shows you that open data is a threat to power. They really try to avoid giving you information that is very sensitive. So that's why it's very important to live in a country where you have free judiciary, where you have good appeal mechanisms, and it sometimes really takes years and years to get to the information, but then you win. And as it was proven in our organization, it feels good after five years to have a headline in the newspaper saying that you won a Supreme Court case against the general prosecution or against the Ministry of Finance and etc. And what it helps you with is that next time the Ministry of Finance or the general prosecution will not rely on not getting you the information because they know that you will come around the corner and you will give it back to them. So what is when working with very well established networks who are powerful, it is important to be clever and to save our own time and resources. That's why we started to develop open data tools that would serve us, but also journalists and others. What you can see here is our application, an internet application that matches up data from official registrar of businesses in Slovakia and registrar of public tenders. So you can put in any name of a person, Slovak or whoever else, and the application will check you how many tenders did companies with activity of such a person won in the Slovak state. And I can see you a result of a very powerful oligarch in Slovakia who is known to sponsor one political party. And it is not surprising to find out that his company has received a public tender's worth of 266 million euros without value edit tax. What you can see thanks to the application as well is a concrete position of this person within the company. So you can see if he was a statutory organ, if he was a director or whatever else, it will also allow you to see which concrete institutions in the state donated these companies with or where he won the tenders. And one of the information that is very interesting and you can see it here is that one of his biggest tenders was within an office of the parliament to reconstruct the national heritage castle. And what is more interesting about it is to know when this tender happens. And it was under the government and under the direct leadership of a representative from this political party that the oligarch is known to sponsor. When you are a journalist and you want to dig in these cases a little further, you can go through a very thorough list of these tenders and you can open each one of them and check for conditions of the tender, check for what other bidders were part of this tender, check for the contract and see for yourself. Another tool that we started to build preventively is that we started to file freedom of information requests with very basic questions. We want to see who is getting donations from the state, who is winning tenders in the state, who is getting European Union funding or all kinds of other public support. We also want to know who sponsors politics, who advises politicians, who is in the chairmanship of companies, who is on boards that decide about subsidies, et cetera, et cetera. So this is an application that collects all this information already for more than 10 years. So when you are a journalist and you want to work on a corrupt case, you don't have to file your own freedom of information requests from Ministry of Finance, to the parliament, to government and wait and wait and wait and see a situation when the government or the parliament doesn't give you the information so you have to appeal, you have to go to court, you have to wait for years. But you can click on this website and you can save yourself time. And I can show you one example of this will ring a bell to you, company Siemens. And we can see what is in our application about Siemens. So what you can find here is all the public tenders that Siemens received in Slovakia over the last 10 years. You can go in the chart. You can see civic associations that carry Siemens names. You can see that people who were advising to politics were connected in some way to Siemens. You can see that a basketball club with the name of Siemens is receiving 2% of tax from Slovakia, that it also donates money to Slovak institutions, to Slovak ministries, especially Ministry of Interior. You can also see that it had debts in custom duty. And you can also see that it receives European Union funding for education of their own employees. So when you are an investigative journalist, you just saved couple of months of work receiving this information from the state. And you can proceed and work on your case on your own. So what I would like to stress is that you would like to stress is that when you do this kind of work, use the media. Get attention, set agenda, but also be patient. And don't try to bluntly copy projects from other settings that might not work in your country. Always listen to your own needs, to your own goals, and get inspiration from others. It helped us many times. But first see if the settings in your country wouldn't be actually working against such a project. So don't replicate blindly. And sometimes it is important, especially in countries like Slovakia, to be creative. When you want a certain information from government that you believe it should be there and it's not, you need to find creative ways how to get it when politicians refuse to give it to you. And one of such examples is a project. We believed that asset declarations of high politicians as the president, ministers, members of parliament should be available online. But we were really frustrated with getting to convince the parliament to pass a legislation that would allow us to gather this information. And we didn't get it. So we decided to form our own project. It's called Open Politics. And it contains voluntary asset declarations of politicians, very detailed ones. So they declare what property they have, what depths they have, where do they travel, who do they meet. And they do it just because they want to and just because we exerted enough pressure through the media and through the citizens to request such an information. After a couple of years of this project where it was really small and unwanted at the start, last year we had a prime minister of Slovakia voluntarily being part of the project. We had the speaker of the parliament. We had half of our government and a lot of members of parliament. And what was really interesting to see is that one of the MPs even asked us if he should include a property that he doesn't own officially, not on paper. He owns it behind the scenes through a secret agreement with a different person. And we said, of course, you have to put it in there. You want to be open and transparent. And then I wondered why he asked us. And what I found out is that once they put information up there and they distinguish themselves from others as being transparent and fair, they really fear that the competition would just tell on them that they are not so transparent and they are not such good guys. So he was actually taking a preventive step from being blamed. Thank you very much. Yeah? So I was told that we have space for questions. So thank you, Susanna. And I give you. Hi, my name is Nikol. And maybe I missed it at the beginning, but how do you get the first information about the contract which was only available inside the ministry? So did you have some kind of whistleblowing or something like that? Yes, it was not part of work of our organization, but the first initial information came to a journalist through a visa-blower, through a secret source. So sometimes it is true that you can't avoid using sources. But what I really wanted to highlight is that open data can liberate you from sources. Many times you find really interesting tracks in the open data itself. So when you are a desperate as a journalist, you don't have to turn to sources, but you can really browse through these registers and through the applications. It's true that this concrete initial information came from a source. But what was interesting and I tried to mention as well is that when the first report came out, really nothing happened. So it was a huge case, but for the first month and a half, nothing really happened with it. Thanks. Any other questions, comments? You mentioned that all contracts are transparent on your platform. Are all invoices of the government also are transparent? Yes. Well, there is an official governmental site that has all the contracts and invoices. Well, there was quite a resistance, especially from municipalities in Slovakia who claimed that publishing all the invoices would be too costly for them. So the state had to come with a compromise and it said that to a certain threshold, I think it's 3,000 euros, you can only publish a list of invoices and contracts, but above that you have to also put in a scan or a document in a machine readable format. So there is a governmental site, but we also produce together with transparency international Slovakia our own site that adds up to the functionality and allows us to work with the data a little bit more. Hi, Susanna. I wanted to ask you because I know in Czech Republic the corruption is really widespread. What, do you have a sister agency or Fair Play in Czech Republic? Would you work together because the problems are obviously similar and a lot of the roots? Yes, we were one country, right? So the problems are similar. Well, we don't, but we work with a lot of organisations also in Czech Republic and we were asked sometimes to also spread to Czech Republic, but you have a great organisation in Prague, which is doing good work. I must say that we are a little bit luckier than you. I was on the jury of a journalistic award in Prague this year and I found out that for example, when your media requested certain amount of information from the state, they had to pay a lot of money because the state said that it would cost hours and hours of work of their officers. So they charged, I think, 1000 euros for information about how much money gets certain highly positioned officials within state administration paid, which could never happen in Slovakia. So in a sense, we are lucky because we have a very progressive Freedom of Information Act that allows us to get information basically free of charge. So thanks a lot. Any other questions? Yes. Well, thanks. It's a great project. Did they ever turn up to you physically? What do you do then? Do you have security protection? I must say that I feel also lucky living in Slovakia. We are told to be this peaceful nation who doesn't lead wars. So I must say that I don't know how courageous we would be in settings as Russia or really harsh countries and I really admire everybody who is doing this kind of work there. So we have a lot of verbal harassment from governments. So when we produce our results, we are usually attacked on press conferences and they try to say that we are spies coming from foreign countries being financed by Jewish money of George Shorosh and these kind of powerful people. So the government is usually trying to attack us verbally. We had a couple of incidents where the office was robbed in a very strange way or we had an incident where we locked the door in the night and when we come back in the morning it was unlocked. It was closed but unlocked so it was clear that somebody was inside. So these kind of things happen but not nothing really life threatening and I hope it will stay that way. Who are you funded by? Yes, we are funded by Open Society Foundation which is established by George Shorosh to a big deal with institutional grants. We also receive help from Slovak citizens through 2% of tax which for example in last year brought 70,000 euros which is quite a lot. We also get funding from Slovak companies especially smaller. We also offer our own consultation and training and get paid for it. We get little sources from Slovak foundations, domestic sources but also other international foundations. But it's always open grant competitions so you submit your grant in an open competition that is actually published to everybody else and you get it or you don't.
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In Central and Eastern Europe opening government information was not only a logical step in gradual organic development of democracies. It was a radical game changer that shifted the power balance in these communities. Thanks to sharing comparable information as the ruling and economical elite citizen could suddenly become equal partners in dialogue and have gained tools to efficiently influence the public debate in favor of necessary reforms. Open government information became a threat to corrupt and nepotic networks deeply established in post communist societies. Not because they would carry direct evidence of corruption but because they documented favoritism, unfair conditions, manipulations with documents and serious flaws in the processes, law application and financial efficiency. This „evidence" was often sufficient to put a stop to a certain practice or at least demand political and legal consequences. Concrete investigations into political cases with use of newly gained right to information and government data became one of the most influential tools in reforming post-communist societies. Thanks to concrete and understandable stories it introduced societies to new paradigms, ethical and legal standards and brought evidence of destructive influence of corruption on our lives. Right to know and use government data became such an important principle that political representations do no dare to touch it. Post-communist societies paradoxically often enjoy higher legal standards and technological tools in transparency and open government than their western role models. Opening government data also liberated journalists and activists from often risky ways of using traditional sources. Our watchdog NGO -- Fair-Play Alliance has been at a forefront of these efforts and investigations. This talk will therefore explore concrete cases from our first-hand experience that have shaken political scene thanks to open information and IT tools and will explore how single cases/instances can lead to deeper reforms and less corruption. It will also analyze the vital prerequisites for efforts to hold governments accountable to avoid failures when replicating an inspiring project in different settings.
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10.5446/20843 (DOI)
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Hi, everybody. My name is Katie Jacobs-Stanton. I'm the vice president of international market development at Twitter. I'm super excited to be here at Republica today. It's the first time that Twitter has been here. And the main reason why we wanted to come to Republica and come to Berlin is to really thank you. Most of you in this audience have been early adopters of Twitter. You've been with us since the beginning. You've laid the foundation for Twitter in Germany and Twitter in Europe, and we really appreciate your feedback and your honesty. In fact, we know that Sasha Lobo was here earlier this week, and he's been a great advocate for us and given us a lot of good, honest feedback. And it's that honest feedback that makes us better. And so we encourage you to use the hashtag RP12 and then do a CC to our Twitter account at Twitter underscore DE. And our team is listening. We're listening in English and in German and probably in whatever language you're tweeting in. And we really want to hear from you and to continue to have this conversation. So I want to talk to you a little bit about Twitter, our vision as a company and as a product. Twitter brings you closer. What does that mean? Over the past couple of years, we've heard stories from our users around the world and stories about news breaking, about revolutions, about joys and tears when their favorite team wins or loses a particular game. We've heard stories about people after a disaster, people who are meeting their friends and family, people who are connecting. And what that has taught us is that Twitter brings you closer to what you most care about in real time. And before I share some of the stories that we're seeing, I want to share some of the high level pieces of information about Twitter. We're growing, we're global, and we're mobile. So first growth, we're growing fast. We have over 400 million unique visits to Twitter every month. We have over 4, sorry, we have over 140 million active users. And we're also up to about 340 million tweets a day. That's a lot of content. The conversations are growing. So just to give you some perspective of scale, so every three days or so, we're seeing about one billion tweets. We're processing almost one billion tweets. And so it took us originally three years, two months, and a day for us to reach that first billion tweet. So that's a lot of conversations going on around the world. Around the world, we're global. So over 70% of all of our accounts are outside of the United States. From the beginning, Twitter knew that we were a global company and that we needed to do a good job to help scale our business and our product to fit the international market. We're now available in 28 languages. We use a crowdsource model where we ask the community and volunteers from around the world in multiple languages. We have over 600,000 translators today who volunteer to make Twitter available in their languages. Some fun facts. We have one out of six accounts that are set to Spanish. It's one of our most active accounts after English. And what's really exciting for us is that we've seen Arabic grow as the fastest language ever on Twitter. We recently launched Twitter in four of the right to left languages, and Arabic, and Hebrew, and Farsi, and Urdu. And so it's very exciting to make sure that we reach every person on the planet and make Twitter as accessible and useful to them wherever they are. Japan was one of the first markets to adopt Twitter. They adopted Twitter early, mostly because everyone was on a mobile device, and they've become some of our most prolific tweeters. In fact, one of our jokes is that in Japanese and Chinese and Korean, all the double-bite languages, you can practically write a novel in 140 characters. We have three offices outside the US. We're a six-year-old company. We're in London and Dublin and Tokyo, and I'll talk a little bit more about more information later. Third, we're powered by mobile. Twitter was born on a mobile device. That's why we're at 140 characters. So we know how important mobile usage is around the world and how important it is to make sure that Twitter is accessible no matter what device you're using. If you're here in Berlin on your iPad with a Wi-Fi connection, or if you're in sub-Saharan Africa on a rudimentary Nokia phone, it's important that we're able to make sure that you can access and use and discover the value of Twitter. In fact, one out of six of our users actually signed up on a mobile device. There are millions of ways to use Twitter. Out of those 140 million active users, 60% of our users actually produce tweets and listen, whereas 40% are just listening. And what that has taught us is that you don't need to tweet to get value out of Twitter. Just by comparison, YouTube, only 1% of YouTube users will actually produce the content. The rest are listening and watching. So content, there's a lot of content on Twitter. And we wanted to share a little bit about who are the top content producers on Twitter. Politicians, no surprise. They want to connect with their electorate. They want to connect with their audiences. We've seen political leaders around the world join Twitter. It's not a matter of if, it's a matter of when. We certainly see this in the United States. We're seeing this in other markets. 2012 is a very important year globally for a lot of presidential elections. We've seen a lot of great activity happening in Mexico and France in particular. Athletes. We've seen athletes from around the world, especially the basketball players, the soccer players, handball players, tennis players. There's a lot of content from a lot of the athletes on Twitter. Humanitarians. We're seeing humanitarians in their agencies and organizations around the world using Twitter to help extend their brand, to help engage with audiences, to share their causes and to raise money. Entertainers from Justin Bieber to Matias Schweighhofer. We're seeing a lot of entertainers, movie stars, and musicians around the world join. And then TV shows. In the U.S. at least, 100% of the most popular TV shows are actually on Twitter. And they're doing a really good job about integrating and engaging the audience to participate in the shows. Today, we have roughly 38 heads of state or their government representatives on Twitter, from the White House, number 10, to Paul Gagami and Rwanda, to the Blue House in Korea. And we've seen a lot of this grow around the world. And people tweet in different ways. Some are very formal. The White House is pretty formal, pretty engaging. Paul Gagami, if you tweet to him today, he'll probably tweet to you right back. Another data point for you, roughly 80% of the G20 are on Twitter. The only five that are missing are Indonesia, Italy, Saudi Arabia, China, which government blocks us and doesn't allow us to participate, and Germany. And so one of the things that we're hopeful about Germany is maybe you guys can get Miracle on Twitter to trend using the hashtag Miracle on Twitter. I know our friend, Stefan Zivert, is up next, so maybe that was kind of unfair. But he's been doing a great job. And he's been one of the earliest adopters in terms of a lot of politicians on Twitter. And he's conducted two Twitter interviews. The second was just yesterday. So he's really doing a good job. But any extra help you can give us, that would be great. So while there's a lot of content coming from a lot of sources, Twitter is event driven. And we've seen huge spikes in conversations around sporting events. So what this chart shows is about six out of the 10 most active events discussed on Twitter are around a sporting event. The World Cup, the Copa, it could be the Super Bowl, and we've seen a lot of soccer games enjoy a lot of content and participation. Several of our other major events happened around TV shows. The BET Awards when Beyoncé was on MTV Awards and she rubbed her belly and became that she was pregnant, everyone rejoiced and had a conversation about it. And then the last one happened in Japan during New Year's Eve. And it's Japanese tradition and custom on New Year's Eve where people will call their friends and family and wish them a happy New Year. And now they're starting to tweak that. And just to give you a little bit of perspective and context, that Twitter has become this second screen for these events and how it's evolved. So just a few years ago for the Super Bowl, which is the big national football game in the United States where everyone tunes in in the U.S., we had about 27 tweets per second in 2008. That increased over 4,000 just last year. And this year we were over 12,000 tweets per second. So it's growing. So many of you, especially bloggers and newsmakers, you fully well understand the power of Twitter as Twitter bringing you closer to the news. You're finding out more and more in real time what's happening in the world. You can tune in at any time and see what journalists are saying, the professional journalists, the professional institutions as they break news. But what's also different is that you see more and more citizen journalists. Twitter has become this open source newsroom where people are able to find out what's going on in the world from the people who are right there. This has happened all over the world. Probably one of the most famous tweets happened with Elgonim in Egypt when he said, welcome back, hashtag Gen25. Sports. Sports has been huge on Twitter. Games, Twitter brings you closer to the arena, to the stadium, to the locker room, wherever you may be. And I wanted to share one example that happened just a couple months ago that wasn't necessarily about the game but was at one of the halftime events called the SpriteSlam. So the NBA had a slam dunking contest, you know, when you kind of jiggle your ball and you go up and you slam the basketball down the hoop. And they did this great contest. And they asked the audience, not just to tweet about it, but to actually influence the outcome of the contest. So they asked the audience to use hashtag SpriteSlam with the name of their favorite player. And what happened is that we saw something like 370,000 tweets in a matter of about 20 minutes during the course of this event. And at its very peak, it accounted for 15% of all worldwide tweets. So it was a pretty fun way for the NBA and for basketball fans to be able to, again, not just participate but to influence the outcome. The other thing that they did, which was really creative, is that they had this auto-tweet capability. So it was the NBA Backboard Cam, which literally gave you this 360 perspective of what it looked like for the athlete and the basketball player to dunk the ball. This chart reflects the difference in the number and the volume of hashtags when the organizers gave a very specific call to action. They said, you know, use SpriteSlam, you will influence the outcome of this game. And you can see how much it outperformed some of our other major hashtag events, including a freak earthquake on the east coast of the United States, as well as this mad lib type of hashtag, what will Gaga wear during the MTV Awards. Television. So Twitter brings you closer to TV in the sense that television has always been social. Since it's very inception, people were gathered around the living room with their friends, with their family, and watching their favorite show. And Twitter brings you closer because you get to participate in that conversation around your program. And I'll share some examples. The first example is about politics. So in the U.S., as many of you know, we're about to engage in a very heated election between Mitt Romney and President Obama. And during the primary campaigns, Fox News worked with us to help engage the audience. And so they had, I'm going to show you a clip, and what they did is that they had all the candidates up there. They asked the audience, is this candidate answering the question, and if they're answering the question, use hashtag answer. If they're dodging the question, use hashtag dodge. And in real time, you could feel the pulse of what people were thinking. Uh-oh. No sound. Well, the candidates are answering the questions. Tweet the candidates last name and hashtag answer if you think he's tackling the question, or hashtag dodge if you think he's avoiding the question. But we're going to take a break right here. Remember to send your thoughts on how the candidates are answering the questions via Twitter. Tweet the candidates last name and hashtag answer or hashtag dodge. Send me questions at atbredbear, include that hashtag SC debate. I don't know if your Twitter page is like mine. Mine is on fire. What have they, what's kind of been the consensus for the first hour of the debate? Let's take a look at this, because this is very interesting. We've got the green line here for Newt Gingrich, a white line for Rick Santorum, and an orange line for Mitt Romney. Let's drill down on this and take a look at Mitt Romney, where the biggest dodges were perceived to be. First of all, his answer is back and forth with Rick Santorum on this issue of felons and whether or not they should be allowed to vote. People thought that he was dodging that and look at the numbers here. And then on his tax records, he was seen as dodging that question so much that we couldn't actually record the number of people who were saying that he was dodging. The foreign policy, tweet me your questions at breathbearer, include hashtag SC debates after this break. At Mr. Whiteman, has no child left behind been a success or a failure? If latter, what needs to be done to change it? Let's go to John Roberts with an update on how the Twitter audience thought the candidates fared tonight. Hi, John. Hey, Newt Gingrich did very well on foreign policy. But Romney, as you can see, below the line, I'm going to tell you he spent most of the nights below the line, Rick Santorum, seen as giving good answers, as well as Rick Perry and Ron Paul. We've got to tell you, Ron Paul spent the entire night in the good answer section. And looking here at Newt Gingrich, Romney's record, he was a little more of a dodge than he was a good answer, the economy, getting good points, race getting very good points, foreign policy, pretty much the same thing. That's the way it came out tonight. It's actually quite funny to re-look at this now that we know who the candidate is going to be and how poorly he did. And here's a chart that you saw during this clip, and it shows the dodge versus the answer. And this is a really important chart. And what it taught all of us is that, you know, for newsmakers that we knew what would be on the front page of all the U.S. newspapers the next day, it would be all about the tax records. People had a very visceral reaction to that. Why isn't he releasing his tax records? And so that was one thing. The second thing is that Mitt Romney's team, they were very, very smart about it. They realized, okay, obviously, we need to listen, and we need to get out these tax records as soon as possible. And so they have become actually one of the strongest users of Twitter and Twitter analytics to be able to really get the most out of Twitter, to be able to amplify some of the positive news and try to squash some of the negative news using Twitter and just being a lot more proactive about how they communicate on our network. I'm going to show you another one, very small clip, too, that talks about how Twitter brings you closer with reality TV. And reality TV, for better or for worse, has become very popular, of course, in Germany, in the U.K., and in the U.S. And this is how these guys used it in order to get the, sorry, to get the population to participate in the show. Let's check in with our Twitter wall, shall we? You guys have been incredibly busy. Tell us, which judge do you agree with the most? Or least, use the hashtags on the screen right now to get on Twitter and let us know we love to hear from you. Now, here's the last performance. It's the final singer of the over 30s. So the X Factor has used this both to sort of tell us how are we doing, how are the judges doing, and they've also used this to help, again, influence the outcome. Who would you like to win? You know, tweet your vote for any of these different participants. If something is happening on television, it's already happening on Twitter. And what this chart reflects is sort of the conversations, the tweets that are happening related to some of these U.S. popular shows. And even if we stripped out the names, Glee, American Idol, and so forth, this would still work for Tatort. This would still work and be the case for DSDS and for Jeremy's Next Top Model. You see spikes about these television shows, you know, as they happen. And then if you even dive in more closely, you'll see spikes when, you know, the criminals revealed or sort of, you know, when the contestant has been nominated or elected or wins a certain prize. And so the conversations are on high speed during the episode. And then they taper off, of course, but they still happen midway. So that's all great, blah, blah, blah. That's all Twitter in the U.S. What about Twitter in Germany? What are you guys doing? So again, many of you have been with us for a long time, but I want to share something that you might know about Twitter in Germany. So this is a sketch that Jack Dorsey, our inventor, had of Twitter in the very early days. And he was challenged by trying to get a prototype of Twitter up in two weeks. And so he leaned on our first engineer and asked him to help prototype it. And that engineer, Florian Weber, was in Hamburg, Germany. And so he actually developed the very first prototype of Germany, working with several of our other colleagues. And so Twitter has these engineering roots here in Germany. And over the years, we've had challenges. We've had challenges of discovery. How do we help you as a user discover the most relevant and interesting real-time content for you? With a billion tweets every couple of days, that's a lot of content. The second challenge we've had is scale. Again, a lot of content. How do we help scale this so everybody can get the information they're looking for quickly? We've also had the challenge of content. There's a lot of content on there, a lot of English content on there. How do we make sure in Germany we're able to surface for you better German content? So we have a small team here in Germany. And they've been working really hard over the past couple of months, working with a number of the different TV stations, for example, to share a lot of the best practices that we've seen in other markets. And also to try to find and define the best types of integrations that might be most relevant in Germany and can even start here. So we work with ZDF and ARD and Prozieben. We've also done several sports integrations with Sports Show and with Sky. And they've been really good about trying to get hashtags on air and to involve the audience in a lot of these conversations. One thing that we started in Germany that we don't have in any other markets, actually, something we call the Sports One Box. And we were very lucky because we have this very passionate German engineer at Twitter in San Francisco who's a Dortmund fan. Any Dortmund fans? That was really easy. That's pandering. And what we realized that Germans love soccer. We talked to any German. They all have their favorite soccer club, their favorite soccer player, and everyone's got a pinion. And how do we make sure that we bring better soccer content onto our platform? So we launched this so you can get these real-time sports scores for the Bundesliga one. And we've seen great upticks so far. So not only do you see the scores, scores are great, but you see the conversations. You see when people are screaming to one another goal, and you see when people rejoice when there's a score and when they're really mad about whatever. And so one of the things we want to do is help scale this. And so again, this is something that we started here in Germany. We want to expand this to other sports. And we also want to help expand this to other markets. Here are some of the tweets that we've seen along the way. So a lot of good tweets from fans, from broadcasters, and then some behind-the-scenes types of tweets and pictures. And then politics. I've mentioned Stefan Zybert before, but we're seeing a lot of politicians actually take the lead on Twitter. As I mentioned earlier, it's not a matter of if. It's a matter of when these politicians are going to join. We're super excited today to see Chairman Gabriel join Twitter from the SPD. We know the Pirates and the Greens and all the political parties here in Germany have been active on Twitter. So again, we're really excited. Is Merkel on Twitter trending yet in Germany? Anyone know? Not yet. Okay, you guys still have work to do. I'm going to keep talking until it's trending. And then there's one more thing. So there's been a lot of speculation. There's been a lot of speculation about Twitter. And Jack Dorsey announced at DLD in January that we're building a team here in Germany. And we're really excited to confirm that we will have our office here in Berlin. So it's very exciting for us. And we're really looking forward to growing our team here. We have two employees who are here in the front row, Rowan Barnett, who's our market director who just literally joined last week. And this is his first week on the ground in Germany working for Twitter. And Issa Zunfeld, who's our partnerships manager, working with, again, the TV stations and the sports teams and the artists to help get them on Twitter. So we want to hear from you. I hope you've been tweeting some good ideas for us and some honest feedback. And we look forward to really building a business in a way that makes us proud here in Germany. Thank you. Dankeschön. Thank you very much, Katie. Are there any questions right now? Okay. I think we need a few microphones right now. Okay. Here first. Me first? Okay. Katie, over here, right side. As far as I'm working as an IT recruitment specialist, I would like to know how many people do you need in Berlin? Well played. It's a small team. You know, we're starting with a small team first. No specific numbers. But if you have great candidates, feel free to send them my way at kds at Twitter. Okay. The next one. Ah, there's the microphone still being searched. Ah, it's been found. Can we go boy, girl, boy, girl? Over there. Here I am. Right back here. Do you see me? Katie, no. Here I am. Waving doesn't help. All right. Anyway, still waving. Go ahead, man. All right. First of all, I'm a professional journalist and I want to say thank you to Twitter. I'm covering defense affairs and when looking at the Afghan war, Twitter is one of the fastest venues of information. I had sometimes information about suicide attacks and things like that before even the German command in Germany had this information. So that was pretty impressive. My question now, however, is when there will be a verified account for all of us? That's a great question. We have a small team that works with verification and what we've tried to do is put together a very clear process, verifying, you know, political leaders and brands and making sure we have athletes and journalists and people that often have a lot of influence. And it's one of our challenges this year because we take it so seriously. We can't possibly verify everybody with the small team that we have. We have a little over 800 employees, most of whom are based in San Francisco. So it's something that we are working on. We have a newsroom team that also works with journalists to help verify journalists. So there too, you know, for the journalists in the room and others, if, you know, again, just email me and our team and we'll happy to send you to our verification team for follow-up. I know the next question is over here. Yeah. Excuse me, I'm just wondering how many Twitter accounts are there in Germany? We don't break out our numbers in Germany or in any specific markets, but there are third parties that do report on some of our numbers and it's pretty easy to find that data. Can we go to... Great. Okay. I work for the foreign ministry and we're still pretty new with social media. So what would you suggest if we thought about using Twitter? What would you suggest to a ministry? Yeah, you should join. And what? Yeah. I've seen some great examples with foreign ministries in Sweden, Carl Bilt, in the UK, William Hague, and in the US with Secretary Clinton in the State Department. And the ways that they've been using has been a variety of different ways. You have to do what's comfortable for you. But first, to be able to represent foreign policy, you know, here's what the foreign minister thinks about the situation in Afghanistan, you know, whatever the issue might be. So the official statement, it's also engaging with citizens. It's engaging with their counterparts in other places, embassies and consulates around the world have been really active on Twitter. There was an issue last November when an Egyptian-American woman, Mona, was in Tyreir Square and she was beaten. And she was able to borrow a friend's phone and she tweeted about it. And within 20 minutes, Andy Carvin of NPR, Nick Kristoff of New York Times, they both had tweeted with the hashtag, free Mona. And within a few hours or so, the US Embassy in Egypt responded and said, we're aware of the situation, we're working behind the scenes, it's important for us to make sure that she gets freed. And it was a great way for an embassy to work proactively about a very serious situation on the ground. So that's just another way that you can use it. And I would say the last way is just general Q&As, William Hagan the UK does this, where every once in a while, UK in the house. And every once in a while, he will do this Q&A and have people say, ask me anything, any question. And as a foreign minister, you can kind of pick which questions and what sort of themes you want to answer. And it's just a very great way to be open and transparent and participatory. Hello, my name is Martin and once was a very happy poster user. And now I'm not very happy. So what's going on with posterers? You know, I don't have a good answer for you because I'm a little bit farther from posterers, but I'd be happy to take your feedback back to Sachin and the team. They just joined us a couple of weeks ago. So I think it might take some time to help with the integration and still support it. But if you can send some specific feedback, that'd be great. It might be. But we'll get your contact information and follow up with the posterers team. One of the last questions over here. Hello, my name is Marin. I'm a very heavy user of Twitter in Germany for three years now. And since I'm on Twitter, I hear speculations about the business model. So Facebook bought Instagram recently. Last night I read LinkedIn bought SlideShare. So when is Twitter going to be sold? No, Twitter is in it for the long term. We've worked very hard about building this business in a way that makes us proud. And we launched our advertising platform two years ago. And we've extended it to several international markets. And we're very pleased with its performance to date. What we've done differently is that we haven't really slept, not really, we haven't slept on ads somewhere on the page that try to get the user's attention. What we've tried to do is make sure that the advertising experience is woven into the fabric of the consumer experience in a good, positive, and useful way. And what we found as a result, that compared to a lot of digital and display and text ads, that the performance of Twitter, of promoted products on Twitter far exceeds that of some of the other offerings. So whereas a display ad you might have.01% click through, our average engagement rates are between 3% and 5%. And in fact, one of our best performing ads was from a German company from Volkswagen that announced the new Beetle. And when they started their campaign, they had a picture, they had a promoted trend, and they had promoted tweets, and they did a really good job. And they had 55% engagement on that effort. More people clicked on that ad than didn't. So we're really pleased with the way that the advertising business is growing for us, and we're going to continue to invest in it and continue to grow our global audience. Okay. I think one more question or... Oh, there's one question. Are you just trying to say hello to a friend? Okay. I don't know. One more question or not? Okay. What? Last one. Okay, just very quickly, I was wondering why you chose Berlin out of all the cities in Germany. What was so special about Berlin that made you base Twitter here? They're a great question. There are a lot of wonderful cities in Germany, Munich and Hamburg and Berlin. And the reason why we chose Berlin was because it's a center, it's the capital of Germany, and it's a hub in Europe of developers and creative artists. And there's so much great energy happening here. And much of what Twitter does is break down walls, and we really couldn't have found a better place for us than here in Berlin. I think that's it. Thank you.
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Twitter has more than 140 million users worldwide, 70% of which are outside of the US. The platform's user base has always been global, but its physical expansion is just getting started. Katie Stanton, VP of International for Twitter will talk about the company's approach to global growth - and how focusing on interest areas like news, sport, and TV has made Twitter an integral part of people's daily lives all over the world.
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10.5446/20788 (DOI)
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Good morning. It's a pleasure to be here and an honor to be at Republica. For the last thousand years, we, our mothers and our fathers, have been struggling for freedom of thought. We have sustained many horrible losses and some immense victories, and we are now at a very serious time. From the adoption of printing by Europeans in the 15th century, we began to be concerned primarily with access to printed material. The right to read and the right to publish were the central subjects of our struggle for freedom of thought for most of the last half millennium. The basic concern was for the right to read in private and to think and speak and act on the basis of a free and uncensored will. The primary antagonist for freedom of thought in the beginning of our struggle was the universal Catholic Church, an institution directed at the control of thought in the European world, based around weekly surveillance of the conduct and thoughts of every human being, based around the censorship of all reading material, and in the end, based upon the ability to predict and to punish unorthodox thought. The tools available for thought control in early modern Europe were poor, even by 20th century standards, but they worked. And for hundreds of years, the struggle primarily centered around that increasingly important first mass-manufactured article in Western culture, the book. Whether you could print them, possess them, traffic in them, read them, teach from them, without the permission or control of an entity empowered to punish thought. By the end of the 17th century, censorship of written material in Europe had begun to break down, first in the Netherlands, then in the UK, then afterwards in waves throughout the European world. And the book became an article of subversive commerce and began eating away at the control of thought. By the late 18th century, that struggle for the freedom of reading had begun to attack the substance of Christianity itself. And the European world trembled on the brink of the first great revolution of the mind. It spoke of liberte, egalité, fraternité, but actually it meant freedom to think differently. The ancien régime began to struggle against thinking. And we moved into the next phase of the struggle for freedom of thought, which presumed the possibility of unorthodox thinking and revolutionary acting. And for 200 years, we struggled with the consequences of those changes. That was then, and this is now. Now, we begin a new phase in the history of the human race. We are building a single nervous system which will embrace every human mind. We are less than two generations now from the moment at which every single human being will be connected to a single network in which all thoughts, plans, dreams, and actions will flow as nervous impulses in the network. And the fate of freedom of thought, indeed the fate of human freedom altogether, something that we have fought for for a thousand years, will depend upon the neuroanatomy of that network. Hours are the last generation of human brains that will be formed without contact with the net. From here on out, every human brain, by two generations from now every single human brain, will be formed from early life in direct connection to the network. Humanity will become a superorganism in which each of us is but a neuron in the brain. And we are describing now, now, all of us, now, this generation, unique in the history of the human race. In this generation, we will decide how that network is organized. Unfortunately, we are beginning badly. Here's the problem. We grew up to be consumers of media. That's what they taught us. We're consumers of media. Now, media is consuming us. The things we read, watch us read them. The things we listen to, listen to us, listen to them. We are tracked. We are monitored. We are predicted by the media we use. The process of the building of the network institutionalizes basic principles of information flow. It determines whether there is such a thing as anonymous reading. And it is determining against anonymous reading. Twenty years ago, I began working as a lawyer for a man called Philip Zimmerman, who had created a form of public key encryption for mass use called pretty good privacy. The effort to create pretty good privacy was the effort to retain the possibility of secrets in the late 20th century. Phil was trying to prevent government from reading everything. And as a result, he was at least threatened with prosecution by the United States government for sharing military secrets, which is what we called public key encryption back then. We said you shouldn't do this. There will be trillions of dollars of electronic commerce if everybody has strong encryption. Nobody was interested. But what was important about pretty good privacy, about the struggle for freedom that public key encryption in civil society represented, what was crucial, became clear when we began to win. In 1995, there was a debate at Harvard Law School, four of us discussing the future of public key encryption and its control. I was on the side, I suppose, of freedom. It's where I try to be. With me at that debate was a man called Daniel Weitzner, who now works in the White House making internet policy for the Obama administration. On the other side was the then deputy attorney general of the United States and a lawyer in private practice named Stuart Baker, who had been chief counsel to the national security agency, Our Listeners, and who was then in private life helping businesses to deal with the listeners. He then became later on the deputy for policy planning in the Department of Homeland Security in the United States and has had much to do with what happened in our network after 2001. At any rate, the four of us spent two pleasant hours debating the right to encrypt. And at the end, there was a little dinner party in the Harvard Faculty Club. And at the end, after all the food had been taken away and just the port and the walnuts were left on the table, Stuart said, all right, among us now that we're all in private, just us girls, I'll let our hair down. He didn't have much hair even then, but he let it down. We're not going to prosecute your client, Mr. Zimmerman, he said. Public key encryption will become available. We fought a long losing battle against it, but it was just a delaying tactic. And then he looked around the room and he said, but nobody cares about anonymity, do they? And a cold chill went up my spine and I thought, all right, Stuart, now I know you're going to spend the next 20 years trying to eliminate anonymity in human society and I'm going to try to stop you and we'll see how it goes. And it's going badly. We didn't build the net with anonymity built in. That was a mistake. Now we're paying for it. Our network assumes that you can be tracked everywhere. And we've taken the web and we've made Facebook out of it. We put one man in the middle of everything. We live our social lives, our private lives in the web and we share everything with our friends and also with our super friend. The one who reports to anybody who makes him, who pays him, who helps him or who gives him the hundred billion dollars he desires. We are creating a media that consume us and media loves it. The primary purpose of 21st century commerce is to predict how we can be made to buy. And the thing that people most want us to buy is debt. So we are going into debt. We're getting heavier, heavier with debt, heavier with doubt, heavier with all we need. We didn't know we needed until they told us we were thinking about it because they own the search box and we put our dreams in it. Everything we want, everything we hope, everything we'd like, everything we wish we knew about is in the search box and they own it. We are reported everywhere all the time. In the 20th century you had to build glubianca, you had to torture people, you had to threaten people, you had to press people to inform on their friends. I don't need to talk about that in Berlin. In the 21st century why bother? You just build social networking and everybody informs on everybody else for you. Why waste time and money having buildings full of little men who check who's in which photographs? Just tell everybody to tag their friends and bing, you're done. Ooh, did I use that word? Bing, you're done. There's a search box and they own it and we put our dreams in it and they eat them and they tell us who we are right back. If you like that, you'll love this and we do. They figure us out, the machines do. Every time you make a link, you're teaching the machine. Every time you make a link about someone else, you're teaching the machine about someone else. We need to build that network. We need to make that brain. This is humanity's highest purpose. We're fulfilling it, but we mustn't do it wrong. Once upon a time the technological mistakes were mistakes. We made them. They were the unintended consequences of our thoughtful behavior. That's not the way it is right now. The things that are going wrong are not mistakes, they're designs. They have purpose and the purpose is to make the human population readable. I was talking to a senior government official in the United States a few weeks ago. Our government has been misbehaving. We had rules. We made them after 9-11. They said we will keep databases about people and some of those people will be innocent. They won't be suspected of anything. The rules we made in 2001 said we will keep information about people not suspected of anything for a maximum of 180 days, then we will discard it. In March, in the middle of the night, on a Wednesday, after everything shut down, when it was raining, the Department of Justice and the Director of National Intelligence in the United States said, oh, we're changing those rules. This small change, we used to say we would keep information on people not suspected of anything for only 180 days maximum. We're changing that a little bit to five years, which is infinity. I joke with my lawyers I work with in New York. They only wrote five years in the press release because they couldn't get the sideways eight into the font for the press release. Otherwise, they'd have just said infinity, which is what they mean. So I was having a conversation with a senior government official I have known all these many years who works in the White House. And I said, you're changing American society. He said, well, we realize that we need a robust social graph of the United States. I said, you need a robust social graph of the United States. Yes, he said, I said, you mean the United States government is from now on going to keep a list of everybody every American knows. Do you think by any chance that should require a law? And he just laughed because they did it in a press release in the middle of the night on Wednesday when it was raining. We're going to live in a world unless we do something quickly in which our media consume us and spit in the government's cup. There will never have been any place like it before. And if we let it happen, there will never be any place different from it again. Humanity will all have been wired together and media will consume us and spit in the government's cup and the state will own our minds. The soon to be ex-president of France campaigned, as you will recall, last month on the proposition that there should be criminal penalties for repeat visiting of jihadi websites. That was a threat to criminalize reading in France. Well, he will be soon the ex-president of France, but that doesn't mean that that will be an ex-idea in France at all. The criminalization of reading is well advanced. In the United States, in what we call terrorism prosecutions, we now routinely see evidence of people's Google searches submitted as proof of their conspiratorial behavior. The act of seeking knowledge has become an overt act in conspiracy prosecutions. We are criminalizing thinking, reading, and research. We are doing this in so-called free societies. We're doing this in a place with the First Amendment. We are doing this despite everything our history teaches us because we're forgetting even as we learn. We don't have much time. The generation that grew up outside the net is the last generation that can fix it without force. Governments all over the world are falling in love with the idea of data mining their populations. I used to think that we were going to be fighting the Chinese Communist Party in the third decade of the 21st century. I didn't anticipate that we were going to be fighting the United States government and the government of the People's Republic of China. And when Mrs. Cruz is here on Friday, perhaps you'll ask her whether we're going to be fighting her too. Governments are falling in love with data mining because it really, really works. It's good. It's good for good things as well as evil things. It's good for helping government understand how to deliver services. It's good for government to understand what the problems are going to be. It's good for politicians to understand how voters are going to think. But it creates the possibility of kinds of social control that were previously very difficult, very expensive, and very cumbersome in very simple and efficient ways. It is no longer necessary to maintain enormous networks of informants, as I have pointed out. Shtazi gets a bargain now if it comes back because Zuckerberg does its work for it. But it's more than just the ease of surveillance. It's more than just the permanence of data. It's the relentlessness of living after the end of forgetting. Nothing ever goes away anymore. What isn't understood today will be understood tomorrow. The encrypted traffic you use today in relative security is simply waiting until there's enough of it for the crypto analysis to work, for the breakers to succeed in breaking it. We're going to have to redo all our security all the time, forever, because no encrypted packet is ever lost again. Nothing is unconnected infinitely, only finitely. Every piece of information can be retained, and everything eventually gets linked to something else. That's the rationale for the government official who says we need a robust social graph of the United States. Why do you need it? So the dots you don't connect today, you can connect tomorrow or next year or the year after next. Nothing is ever lost, nothing ever goes away, nothing is forgotten anymore. So the primary form of collection that should concern us most is media that spy on us while we use them. Books that watch us read them. Music that listens to us listen to it. Search boxes that report what we are searching for to whoever is searching for us and doesn't know us yet. There is a lot of talk about data coming out of Facebook. Is it coming to me? Is it coming to him? Is it coming to them? They want you to think that the threat is data coming out. You should know that the threat is code going in. For the last 15 years what has been happening in enterprise computing is the addition of that layer of analytics on top of the data warehouse that mostly goes in enterprise computing by the name of business intelligence. What it means is you have been building these vast data warehouses in your company for decade or two now. You have all the information about your own operations, your suppliers, your competitors, your customers. Now you want to make that data start to do tricks by adding it to all the open source data out there in the world and using it to tell you the answers to questions you didn't know you had. That's business intelligence. The real threat of Facebook is the BI layer on top of the Facebook warehouse. The Facebook data warehouse contains the behavior, not just the thinking but also the behavior of somewhere nearing a billion people. The business intelligence layer on top of it, which is just all that code they get to run covered by the terms of service that say they can run any code they want for improvement of the experience. The business intelligence layer on top of Facebook is where every intelligence service in the world wants to go. Imagine that you're a tiny little secret police organization in some not very important country. Let's put ourselves in their position. Just call them I don't know what, you know, Kyrgyzstan. You're a secret police. You're in the people business. Secret policing is people business. You have classes of people that you want. You want agents. You want sources. You have adversaries. And you have influence of bulls. That is people you can torture who are related to adversaries. Wives, husbands, fathers, daughters, you know, those people. So you're looking for classes of people. You don't know their names, but you know what they're like. You know who is recruitable for you as an agent. You know who are likely sources. You can give the social characteristics of your adversaries. And once you know your adversaries, you can find the influence of bulls. So what you want to do is run code inside Facebook. It will help you find the people that you want. It will show you the people whose behavior and whose social circles tell you that they are what you want by way of agents, sources, what the adversaries are and who you can torture to get to them. So you don't want data out of Facebook. The minute you take data out of Facebook, it is dead. You want to put code into Facebook and run it there and get the results. You want to cooperate. Facebook wants to be a media company. It wants to own the web. It wants you to punch like buttons. Like buttons are terrific even if you don't punch them because they're web bugs, because they show Facebook every other web page that you touch that has a like button on it, whether you punch it or you don't. They still get a record. The record is you read a page which had a like button on it. And either you said yes or you said no. And either way, you made data. You taught the machine. So media want to know you better than you know yourself. And we shouldn't let anybody do that. We fought for a thousand years for the internal space, the space where we read, think, reflect, and become unorthodox inside our own minds. That's the space that everybody wants to take away. Tell us your dreams. Tell us your thoughts. Tell us what you hope. Tell us what you fear. This is not weekly oricular confession. This is confession 24 by 7. The mobile robot that you carry around with you, the one that knows where you are all the time and listens to all your conversations, the one you hope isn't reporting in at headquarters, but it's only hope. The one that runs all that software you can't read, can't study, can't see, can't modify, and can't understand. That one. That one is taking your confession all the time. When you hold it up to your face from now on, it's going to know your heartbeat. That's an Android app right now. Microchanges in the color of your face reveal your heart rate. That's a little lie detector you're carrying around with you. Pretty soon I'll be able to sit in a classroom and watch the blood pressure of my students go up and down. In a law school classroom in the United States, that's really important information. But it's not just me, of course. It's everybody, right? Because it's just data and people will have access to it. The inside of your head becomes the outside of your face, becomes the inside of your smartphone, becomes the inside of the network, becomes the front of the file at headquarters. So we need free media or we lose freedom of thought. It's that simple. What does free media mean? Media that you can read, that you can think about, that you can add to, that you can participate in without being monitored, without being surveilled, without being reported in on. That's free media. If we don't have it, we lose freedom of thought, possibly forever. Having free media means having a network that behaves according to the needs of the people at the edge, not according to the needs of the servers in the middle. Making free media requires a network of peers, not a network of masters and servants, not a network of clients and servers, not a network where network operators control all the packets they move. This is not simple, but it's still possible. We require free technology. The last time I gave a political speech in Berlin, it was in 2004. It was called the Gedankens in Frey. I said we need three things, free software, free hardware, free bandwidth. Now we need them more. It's eight years later. We've made some mistakes. We're in more trouble. We haven't come forward. We've gone back. We need free software. That means software you can copy, modify, and redistribute. We need that because we need the software that runs the network to be modifiable by the people the network embraces. The death of Mr. Jobs is a positive event. I'm sorry to break it to you like that. He was a great artist and a moral monster. And he brought us closer to the end of freedom every single time he put something out because he hated sharing. It wasn't his fault. He was an artist. He hated sharing because he believed he invented everything, even though he didn't. Inside those fine little boxes with the lit up apples on them, I see all around the room is a bunch of free software tailored to give him control. Nothing illegal, nothing wrong. He obeyed the licenses. He screwed us every time he could, and he took everything we gave him, and he made beautiful stuff that controlled its users. Once upon a time there was a man here who built stuff in Berlin for Albert Speer. His name was Philip Johnson, and he was a wonderful artist and a moral monster. And he said he went to work building buildings for the Nazis because they had all the best graphics. And he meant it because he was an artist, as Mr. Jobs was an artist. But artistry is no guarantee of morality. We need free software. The tablets that you use that Mr. Jobs designed are made to control you. You can't change the software. It's hard even to do ordinary programming. It doesn't really matter. They're just tablets. We just use them. We're just consuming the glories of what they give us, but they're consuming you too. We live, as the science fiction we read when we were children, suggested we would among robots now. We live commensally with robots, but they don't have hands and feet. We're their hands and feet. We carry the robots around with us. They know everywhere we go. They see everything we see. We list everything we say they listen to, and there is no first law of robotics. They hurt us every day. And there's no programming to prevent it, so we need free software. Unless we control the software in the network, the network will in the end control us. We need free hardware. What that means is that when we buy an electronic something, it should be ours, not someone else's. We should be free to change it, to use it our way, to assure that it is not working for anyone other than ourselves. Of course, most of us will never change anything, but the fact that we can change it will keep us safe. Of course, we will never be the people that they most want to surveil. The man who will not be president of France, for sure, but who thought he would, now says that he was trapped and his political career was destroyed not because he raped a hotel housekeeper, but because he was set up by spying inside his smartphone. Maybe he's telling the truth, and maybe he isn't. But he's not wrong about the smartphone. Maybe it happened, maybe it didn't, but it will. We carry dangerous stuff around with us. Everywhere we go, it doesn't work for us. It works for someone else. We put up with it. We have to stop. We need free bandwidth. That means we need network operators who are common carriers, whose only job is to move the packet from A to B. They're merely pipes. They're not allowed to get involved. It used to be that when you shipped a thing from point A to point B, if the guy in the middle opened it up and looked inside it, he was committing a crime. Not anymore. In the United States, the House of Representatives voted last week that the network operators in the United States should be completely immunized against lawsuits for cooperating with illegal government spying so long as they do it, quote, in good faith, close quote. And capitalism means never having to say, you're sorry, you're always doing it in good faith. In good faith, all we wanted to do was make money, your honor, let us out. Okay, you're gone. We must have free bandwidth. We still own the electromagnetic spectrum. It still belongs to all of us. It doesn't belong to anybody else. Government is a trustee, not an owner. We have to have spectrum we control equal for everybody. Nobody's allowed to listen to anybody else. No inspecting, no checking, no record keeping. Those have to be the rules. Those have to be the rules in the same way that censorship had to go. If we don't have rules for free communication, we are reintroducing censorship whether we know it or not. So we have very little choice now. Our space has gotten smaller. Our opportunity for change has gotten less. We have to have free software. We have to have free hardware. We have to have free bandwidth. Only from them can we make free media. But we have to work on media too, directly, not intermittently, not offhand. We need to demand of media organizations that they obey primary ethics. A first law of media robotics, do no harm. The first rule is do not surveil the reader. We can't live in a world where every book reports every reader. If we are, we're living in libraries operated by the KGB. Well, Amazon.com. Or the KGB. Or both. You'll never know. The book, that wonderful printed article, that first commodity of mass capitalism, the book is dying. It's a shame, but it's dying. And the replacement is a box which either surveils the reader or it doesn't. You will remember that Amazon.com decided that a book by George Orwell could not be distributed in the United States for copyright reasons. They went and erased it out of all the little Amazon book reading devices where customers had purchased copies of animal farm. Oh, you may have bought it, but that doesn't mean you're allowed to read it. That's censorship. That's book burning. That's what we all lived through in the 20th century. We burned people, places and art. We fought. We killed tens of millions of people to bring an end to a world in which the state would burn books. And then we watched as it was done again and again. And now we are preparing to allow it to be done without matches everywhere, anytime. We must have media ethics and we have the power to enforce those ethics because we're still the people who pay the freight. We should not deal with people who sell surveilled books. We should not deal with people who sell surveilled music. We should not deal with movie companies that sell surveilled movies. We're going to have to say that even as we work on the technology because otherwise capitalism will move as fast as possible to make our efforts at freedom irrelevant and there are children growing up who will never know what freedom means. So we have to make a point about it. It will cost us a little bit. Not much, but a little bit. We will have to forego and make a few sacrifices in our lives to enforce ethics on media. But that's our role. Along with making free technology, that's our role. We are the last generation capable of understanding directly what the changes are because we have lived on both sides of them and we know. So we have a responsibility. You understand that? It's always a surprise to me, though it is deeply true, that of all the cities in the world I travel to, Berlin is the freest. You cannot wear a hat in the Hong Kong airport anymore. I found out last month trying to wear my hat in the Hong Kong airport. You're not allowed. It disrupts the facial recognition. There will be a new airport here. Will it be so heavily surveilled that you won't be allowed to wear a hat because it disrupts the facial recognition? We have a responsibility. We know. That's how Berlin became the freest city that I go to because we know, because we have a responsibility, because we remember, because we've been on both sides of the wall. That must not be lost now. If we forget, no other forgetting will ever happen. Everything will be remembered. Everything you read all through life. Everything you listened to. Everything you watched. Everything you searched for. Surely we can pass along to the next generation a world freer than that. Surely we must. What if we don't? What will they say when they realize that we lived at the end of a thousand years of struggling for freedom of thought? At the end, when we had almost everything, we gave it away for convenience, for social networking, because Mr. Zuckerberg asked us to, because we couldn't find a better way to talk to our friends, because we loved the beautiful, pretty things that felt so warm in the hand, because we didn't really care about the future of freedom of thought, because we considered that to be someone else's business, because we thought it was over, because we believed we were free, because we didn't think there was any struggling left to do. That's why we gave it all away. Is that what we're going to tell them? Is that what we're going to tell them? Free thought requires free media. Free media requires free technology. We require ethical treatment when we go to read, to write, to listen, and to watch. Those are the hallmarks of our politics. We need to keep those politics until we die, because if we don't, something else will die, something so precious that many, many, many of our fathers and mothers gave their lives for it, something so precious that we understood it to define what it meant to be human, it will die if we don't keep those politics for the rest of our lives. And if we do, then all the things we struggled for will get, because everywhere on earth, everybody will be able to read freely, because all the Einstein's in the street will be allowed to learn, because all the Stravinsky's will become composers, because all the Salk's will become research physicians, because humanity will be connected and every brain will be allowed to learn and no brain will be crushed for thinking wrong. Here at the moment where we get to pick, whether we carry through that great revolution we've been making bit by bloody bit for a thousand years, or whether we give it away for convenience, for simplicity of talking to our friends, for speed in search, and other really important stuff. I said in 2004 when I was here, and I say now, we can win. We can be the generation of people who completed the work of building freedom of thought. I didn't say then, and I must say now, that we are also potentially the generation that can lose. We can slip back into an inquisition worse than any inquisition that ever existed. It may not use as much torture, it may not be as bloody, but it will be more effective. And we mustn't, mustn't let that happen. Too many people fought for us, too many people died for us, too many people hoped and dreamed for what we can still make possible, we must not fail. Thank you very much. Let's learn how to take questions here. It's not going to be simple, but let's set a good example. Thank you. You put forward a very gruesome picture of the possible future. Could you name some organizations or groups in the United States that put forward action in your way, in your positive way of transforming a society? Not only in the United States, but around the world, we have organizations that are concerned with electronic civil liberties. The EFF, the Electronic Frontier Foundation in the United States, La Quarture du Net in France, Bits of Freedom in the Netherlands, and so on. Electronic civil liberties agitation is extraordinarily important. Pressure on governments to obey rules that came down from the 18th century regarding protection of human dignity and the prevention of state surveillance are crucially important. Unfortunately, electronic civil liberties work against governments are not enough. The Free Software Movement, the FSF, the Free Software Foundation in the United States, and the Free Software Foundation Europe headquartered in Germany are working in an important way to maintain that system of the anarchistic creation of software which has brought us so much technology we can control. That's crucially important. The Creative Commons movement, which is strongly entrenched, not only in the United States and Germany, but in more than 40 countries around the world, is also extraordinarily important because Creative Commons gives to creative workers alternatives to the kind of massive over control in the copyright system which makes surveillance media profitable. The Wikipedia is an extraordinarily important human institution, and we need to continue to support the Wikimedia Foundation as deeply as we can. Of the 100 most visited websites in the United States in a study conducted by the Wall Street Journal of 100 most visited websites in the United States, only one does not surveil its users. You can guess which one it is. It's Wikipedia. We have enormously important developments now going on throughout the world of higher education. As universities begin to realize that the costs of higher education must come down and that brains will grow in the web, the Universitat Obert de Catalunya, the walk is the most extraordinary online only university in the world right now. It will soon be competing with more extraordinary universities still. MITx, the Massachusetts institution of technologies, new program for web education will provide the highest quality technical education on earth for free to everybody everywhere all the time, building on existing MIT open courseware. Stanford is about to spin off a proprietary web learning structure which will be the Google of higher education if Stanford gets it lucky. We need to support free higher education on the web. Every European national ministry of education should be working on it. There are many places to look for free software, free hardware, free bandwidth and free media. There's no better place to look for free media right now on earth than this room. Everybody knows what they can do. They're doing it. We just have to make everybody else understand that if we stop or if we fail, freedom of thought will be the casualty and we'll regret it forever. We've had three more questions in the meantime. The gentleman with the microphone over here will begin. I'm sure there are more of you in the back. Raise your hands high. Maybe yours first, please. Thank you very much. I just wanted to ask a short question. Can Facebook, can iPhone and free media coexist on a long range? Probably not. But we don't have to worry too much. iPhone is just a product. Facebook's just a commercial version of a service. I said recently to a newspaper in New York that I thought Facebook would continue to exist for somewhere between 12 and 120 months. I still think that's correct. Federated social networking will become available. Federated social networking in a form which allows you to leave Facebook without leaving your friends will become available. Better forms of communication without a man in the middle will become available. The question will be, will people use them? Freedom Box is an attempt to produce a stack of software that will fit in a new generation of low-power, low-cost hardware servers the size of mobile phone chargers. And if we do that work right, we will be able to give billions of web servers to the net, which will serve the purpose of providing competing services that don't invade privacy and are compatible with existing services. But mobile phones get changed very frequently. So iPhone goes away. It's no big deal. And web services are much less unique than they appear right now. Facebook's a brand. It's not a thing that we need to worry about in any great particular. We just have to do it in as quickly as possible. Coexistence? Well, all I have to say about that is they're not going to coexist with freedom. So I'm not sure why I should coexist with them. Hi. I'm Chehid-ul-Alam from Bangladesh. Thank you for that wonderfully lucid, scintillating and hugely informative presentation. I was involved in introducing email to Bangladesh in the early 90s. And at that time, connectivity was very expensive. We were spending 30 US cents per kilobyte. So a megabyte of data would be $300. It's changed from then, but it's still very tightly constrained by the regulatory bodies. So we on the ground find it very difficult because the powers that be, the gatekeepers, have a vested interest in maintaining that. But in that gatekeeper nexus, there is also a nexus between governments in my country and governments in yours. And right now, the largest biometric data in the world is the census of Bangladesh. And the company that's providing it is a company that's directly linked to the CIA. So what do we as practitioners do to overcome very, very powerful entities? This is why I began by speaking about the United States government's recent behaviors. My colleagues at the Software Freedom Law Center in India have been spending a lot of time this past month trying to get a motion through the upper house of the Indian parliament to nullify Department of IT regulations on the censorship of the Indian net. And of course, the good news is the largest biometric database in the world will soon be the retinal scans that the Indian government are going to require if you want to have a propane gas cylinder or anything else like energy for your home. And the difficulty we've been having in talking to Indian government officials this month is that they say, well, if the Americans can do it, why can't we? Which is unfortunately true. The United States government has this winter lowered the bar around the world on internet freedom in the sense of data mining your society to the Chinese level. They fundamentally agreed. They're going to data mine the hell out of their populations, and they're going to encourage every other state on earth to do the same. So I'm entirely with you about the definition of the problem. We are not now any longer living in a place in a stage in our history where we can think in terms of a country at a time. Globalization has reached the point at which these questions of surveillance of society are now global questions. And we have to work on them under the assumption that no government will decide to be more virtuous than the superpowers. I don't know how we're going to deal with the Chinese Communist Party. I do not know. I know how we're going to deal with the American government. We're going to insist on our rights. We're going to do what it makes sense to do in the United States. We're going to litigate about it. We're going to push. We're going to shove. We're going to be everywhere, including in the street about it. And I suspect that's what's going to happen here, too. Unless we move the biggest of the societies on earth, we will have no hope of convincing smaller governments that they have to let go of their controls. So far as bandwidth is concerned, of course, we're going to have to use unregulated bandwidth. That is, we're going to have to build around 802.11 and Wi-Fi and any other thing that the rules don't prevent us from using. And how is that going to reach the poorest of the poor when the mobile phone system can be shaped to reach the poorest of the poor? I don't know. But I've got a little project with street children in Bangalore trying to figure it out. We have to. We have to work everywhere. If we don't, we're going to screw it up for humanity and we can't afford the risk. Thank you. The gentleman over here, please. Yes. Professor Moglen, I also want to thank you. I can tell you that I come from transforming freedom.org in Vienna. And some years ago, I saw you talking on a web video at FOSDEM. And there I saw you pointing out the role of Zimmerman, Frederick, and we tried to help him as well. But listening to you today, I see that this is just too slow, too little. And I'm a bit amazed at two things. The first is the academic system. Let's say the European one was founded by Plato and was closed down by FOSD about 1,000 years after. The second start of the European university was around the 11th century. And let's see if we get there to have it running as long as 1,000 years. So my question is, why is it not deeply in the self-structuring of academia to help the cause that you have talked about today? And why don't we have philanthropists helping our little projects running for three or 5,000 euros here and there, much more, let's say, efficiently, like maybe you would agree that Mr. Soros tries to do? Some years ago at Columbia, we tried to interest faculty in the state of preservation of the libraries. And I saw more distinguished scholars at my own university than at any other time in my 25 years there engaged politically. Their primary concern was the aging of the paper on which were printed the 19th century German Dr. Ott that conserved more philological research than any other literature on earth, right? But it was 19th century books they needed to preserve. The problem with academic life is that it is inherently conservative because it preserves the wisdom of the old. And that's a good thing to do, but the wisdom of the old is old. And it doesn't necessarily embrace the issues of the moment perfectly. I mentioned the walk because I think it's so important to support the university as it maneuvers itself towards the net and away from the forms of learning that have characterized the matriculatory university of the past. For the last thousand years, mostly we moved scholars to books. And the university grew up around that principle. It grew up around the principle that books are hard to move and people are easy, so you bring everybody to it. Now we live in a world in which it is much simpler to move knowledge to people. But the continuance of ignorance is the desire of businesses that sell knowledge. What we really need is to begin ourselves to help to turn the university system into something else, the something which allows everybody to learn and which demands unsurveilled learning. The commissioner for information society will be here. She should speak to that. That should be the great question of the European Commission. They know, they printed a report 18 months ago that said for the cost of 100 kilometers of road, you can scan one sixth of all the books in European libraries. That means for the cost of 600 kilometers of road, we could get them all. We built a lot of roads in a lot of places, including Greece in the past 10 years. And we could have scanned all the books in Europe at the same time and made them available to all humanity on an unsurveilled basis. If Mrs. Cruz wants to build a monument to herself, it isn't going to be as a Feifei de Politician. She's going to do it this way and you're going to ask her, I'm going to be on a plane on my way back across the Atlantic or I promise you I'd ask her myself. Ask her for me. Say it's not our fault, Evan wants to know. If you want to hurt somebody, hurt him. You should be changing the European university. You should be breaking it up into unsurveilled reading. You should be putting Google books and Amazon out of business. That's some North American Anglo-Saxon elbow capitalism thing. Why aren't we making knowledge free in Europe and assuring that it's unsurveilled? That would be the biggest step possible and it's within their power. Thank you so much. Brilliant. Thank you.
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Media that spy on and data-mine the public are capable of destroying humanity's most precious freedom: freedom of thought. Ensuring that media remain structured to support rather than suppress individual freedom and civic virtue requires us to achieve specific free technology and free culture goals. Our existing achievements in these directions are under assault from companies trying to bottleneck human communications or own our common culture, and states eager to control their subjects' minds. In this talk--one of a series beginning with "The dotCommunist Manifesto" and "Die Gedanken Sind Frei"--I offer some suggestions about how the Free World should meet the challenges of the next decade.
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