Okay, so let's pick up where we left off. We've been talking about alkali organometallics where you have organic compounds bonded to sodium. Thank you, Chris. Lithium, potassium, even magnesium, different column, but same idea. And so we talked about some various methods for accessing things like alkali-lithiums or grignard reagents. The first method that we mentioned is just direct reaction with metal, sort of like a reductive lithiation for organometallic chemistry. And really, you don't use this in the lab. This is not typical. This is the way they prepare commercial reagents, the cheap ones that you buy on huge scale, butylithium, methylithium, phenylithium, stuff like that. So that's not the kind of thing you would do in the lab. Traditionally, in organic synthesis, if you're making very complex organolithium reagents, you're usually most often using something like this. You do a lithium halogen exchange.  That's more commonly the way that you will make an alkylithium in the lab. There's another exchange reaction, tin lithium exchange, where you can take any sort of a standing compound, for example, this one. You couldn't have a halide here because the lone pairs on oxygen would push that out. But you can make these kinds of alpha-stannyl ethers and do lithium tin exchange if you want to make this kind of alkoxy alkyl lithium. So those are three common ways to get access to alkylithiums. And so the fourth way that we'll talk about that is very common is reductive lithiation. This is not an simple exchange reaction. And so here's the way this typically works. The basic idea is that if you take lithium wire, that's the way you buy lithium. You buy these coils of wire stored in oil so it's not in contact with air or oxygen. And then you simply mix that with naphthalene, very cheap.  You get something called lithium naphthalenide. Lithium naphthalenide. And so how do you think of what would you get if lithium dumped its electron into this system? How do you even depict that? We don't have a good depiction for that. Let me give you one way of thinking about that. I'll simply erase this bond here and I'll draw that pi bond as two electrons. And so now if we imagine dumping one extra electron, we can at least see where we might put that extra electron. And the problem is we have so many resonance structures we can draw that it just becomes that nobody draws it. So here's one resonance structure. Let's suppose I put that extra electron over here. Now you just imagine all the other resonance structures you can draw, maybe that would be a good exercise. And then you can get a sense for what lithium naphthalenide looks like. Okay, so it's very easy to make lithium naphthalenide just simply by mixing lithium wire with cheap naphthalene.  And the beauty of this reagent is that it's super easy to make just by stirring these two things together. And then any place on the planet where you have a thiophenyl group, like here, for example, you simply drip in this reagent and instantaneously you get conversion from thiophenyl to lithium. So here would be an example. You take this lithium naphthalenide reagent and for whatever reason I'm going to draw out this weird structure that kind of looks uncomfortable.  You've got an alkyl lithium that you couldn't make from a halide that you could or easily you couldn't make that from a halide or you don't have to go through some toxic tin species. Very easy to put, try to put two of these electrons closer on one carbon. I hope you did a better job. At least I want to be clear or whatever. There's an extra electron in there. You can draw the resonance structures. Now one of the problems with this is at the end of the reaction you've got just a ton of naphthalene left over. There's just a ton of naphthalene in there after this reaction is over. So in order to make it easier to remove that a lot of people start with this naphthalene derivative and then they can just wash it away with an acid wash at the end. You know it slightly changes the reduction potential, your ability to put a dump of electron in but the main point here is you just want an easy way to do an acid wash and get rid of all this greasy naphthalene that's going to junk up your column. Okay so here's what's cool.   We're not really talking a lot about radical mechanisms. You know as soon as I start talking about this naphthalene we have to start talking about donating an electron somewhere. So I'll give you one way to think about the initial structure. If you have a thiophenyl group attached to anything like T-butyl here's a way to think about what's going on. There's lithium cations floating around. They will coordinate to this sulfur and so if that dumps an electron into this benzene ring so let me just draw one of the double bonds in benzene as just two electrons. You can imagine that I could have drawn that as a pi bond and so what would happen if I put an extra electron in there? I put the lithium cation here. I put the extra electron over at one of these places and here's where I'll draw it like that. And now you can imagine this thing fragmenting. You can imagine this thing fragmenting in such a way that you would end up initially with a radical here on your carbon atom. And then fragmenting so I'd give one electron to here and I'm not going to show you how I get to that resonance structure but the resonance structure that I get to for this thiophenyl species is lithium thiophenoxide. So when you fragment this you get a carbon radical that desperately wants another electron and lithium is happy. The lithium naphthalenide is happy to dump an electron into a T-butyl radical and then I get this byproduct and that byproduct is floating around in your reaction mixture. It's not hurting you. Won't be more reactive than the alkyl lithium that you make. As a consequence of this, because the whole idea behind this is it involves formation of a radical intermediate that then gets converted into an anion, into an alkyl lithium, as you see this set of relative rates, do you get the fastest rates for reductive lithiation for tertiary alkyls? Remember tertiary alkyl lithiums tend to be much more reactive, screaming hot reactive than primary alkyl lithiums. But if you start with a thiophenyl, they form fastest. Alkyl lithiums form fastest when you have tertiary alkyl. That's faster than just primary. A thiophenyl is getting converted into primary alkyl lithiums and that's faster than, and in fact very hard to do this because it's very hard to make just a phenyl radical where there's a single electron in an orbital sticking off the side of a benzene ring. So this would be very, very slow to do just a thiophenyl ether conversion. Okay, so that's method number four, reductive lithiation. If you want to make an alkyl lithium, just put a thiophenyl somewhere, anywhere, hexane, t-butyl group, you'll be able to convert that into an alkyl lithium. Okay, so I'm going to come back to this idea of lithium halogen exchange. And you can make the same arguments for tin lithium exchange, but let me just remind you of the mechanism for this reaction. The important point behind this reaction right here, this exchange reaction and what makes it work is the fact that there's an equilibrium that favors this side and I want to talk about that equilibrium. Again, if you want to draw the mechanism for this reaction, it would look like this. You would have this initial eight formation of an eight complex, two bonds to the halogen. You'd have this iodate and now this bond, both of these bonds become nucleophilic and so you can imagine this attacking lithium and that's how you get the product. So, but let's forget the arrow pushing mechanism for now. I mean, I'd like you to know how to do that, but let's forget the arrow pushing mechanism and just focus on the thermodynamics here. What should we expect if we take a series of alkyl lithiums and we allow them to exchange? So somebody measured an entire series of compounds to figure out in which direction should this equilibrium be most powerfully directed? So everything here is compared to phenyl lithium formation. Let's go ahead and make a table where we look at the equilibrium constants for this reaction and I'm trying to write KEQ up here. I'm going to give you equilibrium constants for this process and so we're going to start off here with formation of vinyl lithium. And what we would find is that the equilibrium constant for this is very poor. Then finally phenyl lithium and I'm, let me try to be a little bit more space conscious here because I've got several compounds to show you. Cyclopropyl lithium, finally butyl lithium, not finally, but butyl lithium and then a secondary alkyl lithium. You're never going to make or work with cyclopentyl lithium but you might work with sec butyl lithium. That's a secondary alkyl lithium that's very common. So imagine taking away one of these carbons and just having a butyl, a secondary butyl group. So now this is a very powerful donor for lithium. So if you really want to drive lithium halogen exchange, go to a secondary alkyl lithium. If you want to drive lithium halogen exchange, you wouldn't just put in vinyl lithium, the equilibrium would lie on this side. Obviously if you put in phenyl lithium and phenyl iodide, you'd have a 1 to 1 equilibrium constant and if you really want to make a phenyl lithium, you start to use alkyl lithium. Butyl lithium will very, will, will drive this equilibrium toward phenyl lithium formation and finally the best would be a tertiary alkyl lithium. If you really want, and I don't have an actual number here, all I can say is it's greater than 10 million. It's greater than a secondary alkyl lithium. When you really see people want to absolutely drive alkyl lithium formation from a halide, they throw in T-butyl lithium as their reagent. So it's a pretty amazing, pretty amazing reaction and what's amazing is that this tin halogen exchange, the attack on iodide that I showed you, this attack of an alkyl lithium attacking some sort of a halide and I'll just write arrow here. Well, let me draw another alkyl group. This attack like this on iodine to make this iodate is faster than SN2. That's what may be strange to you. It's vastly faster than an SN2 reaction. So in other words, you don't get this happening. I don't even want to put a regular arrow. I'll put a dashed arrow there to try to give you an idea. You don't get SN2 in these types of processes. You keep the temperatures low. You'll just get straight up exchange of lithium per halogen. Let me try to switch pens here because I feel like I'm running out. Okay, so very powerful and very easy to simply add butylithium to your alkyl iodides and convert those into alkylithiums. Okay, let me show you what I feel is the most obvious way to make something reminiscent of a carbanion and that's deprotonation. Can we just take alkanes or organic compounds and deprotonate them? And what are the limitations? Mechanistically, that seems like the simplest mechanism to me is simply deprotonating CHs. And the term that we're going to use for that is medallation. And so let me go ahead and come back and remind you. Like if you wanted to simply deprotonate an alkane, you want to obey thermodynamics. If you simply wanted to make an alkylithium like this by deprotonating ethane, you have to remember, you need something more basic than ethane. If you really wanted thermodynamically to have a plausible process. And it's hard to think of things that are that much more basic than ethane. But it's not hard to think of things that are more basic than ethane. You could just take an alkylithium and it ought to be able just, butylithium ought to be able to thermodynamically deprotonate these protons, these sp2 hybridized, these protons on sp2 hybridized carbons. And that ought to be way more, it ought to be even more facile to deprotonate the end of an alkyne. Just using something that's more basic than an alkyne. And so what kinds of things can we use? So typically, I don't have room here. I misallocated my space here, but, you know, you could use an amide anion to deprotonate. So let me remind you of the pKa's for this. So, and really this is a pKa prime. pKa prime means what if I had a proton there instead of lithium, right? I can't ask about the pKa of this because this isn't an acid. But if I stuck the H back there and you consider them acid, now I can talk about the pKa and we call it the pKa prime. So the pKa for simple alkanes is about 50. We talked about these pKa's. pKa's for an sp2 hybridized vinyl group is about 41 to 42. So for a simple terminal alkyne, it's about 24. And then I want you to remember this later. The pKa for, and we talked about this, for just a simple amine. To deprotonate an amine, like diisopropyl amine to make LDA, that has a pKa of about 36. Okay, so this is the thermodynamics. Let's talk about a reaction that is just completely impractical. Basically what I'm telling you is that thermodynamically you can do this. And I'll draw the H there. What I've just told you is that it's thermodynamically favorable to deprotonate benzene rings with butylythium, right? By nine orders of magnitude, the equilibrium constant favors formation of the phenylithium. But you have never seen anybody deprotonate benzene with butylythium. You've never seen that. And the problem is not thermodynamics. The problem is kinetics. It is just too slow. So there's no problem. Of course you could draw the arrow pushing mechanism where you take these super nucleophilic electrons in this bond here and attack the proton. It's just too slow. Okay, so how acidic do things have to be before you can do just simple metallation? Just simple deprotonation reactions of alkane type compounds. And I'll show you an example of where it can be acidic enough. And it's right here. Probably if you took a sophomore organic chemistry course in the United States, one of the first alkyl anion reactions you learn about is deprotonating acetylides. Just direct deprotonation. And you don't have to be very basic to have good enough rates for deprotonation. You can take butylythium and deprotonate in alkyne. You could take even a grignard, which is traditionally very nucleophilic but not very basic. And even this occurs at a fast enough rate. That's what's astounding. Grignards are not super basic. They're very nucleophilic. But it's surprising that even a grignard reagent is basic enough to pull off that proton at convenient rates. And I don't want to draw that as a lone pair. I'll draw it out like this. And so the byproduct of this would be ethane. Okay, so of course the equilibrium is favorable. You can look at the pKa's over there and see that this equilibrium favors this side by 50 minus 24 by 26 orders of magnitude. But what's amazing is that the rates are good. So it's very easy to deprotonate alkynes. Surprisingly easy. That's the basis of a sonogashira coupling. So in a sonogashira coupling, you take alkynes and palladium and triethylamine and copper. And under those mildly basic conditions, you're deprotonating that alkyne. I'll show you a surprising sort of factoid. So if you take sodium ethoxide and ethanol as the solvent for this and you do this substitution reaction, you know, so what's the mechanism for this substitution to replace this chloride with an ethoxy group? What's completely amazing is that if you measure the rates, the rate is first order. There's a first order dependence on the concentration of sodium ethoxide. Why is it that if you add 10 times more sodium ethoxide, the rate gets 10 times faster? What that tells you for certain, it is not a simple SN1 reaction, right? For SN1 reactions, the rate has nothing to do with the nucleophile. It's how fast you form the carbocation. So it can't be an SN1 reaction, but it's also pretty unlikely that this is SN2 to attack at the tertiary center. It turns out that what's happening here is that the mechanism involves deprotonation initially to make this terminal alkyne. Who would have thought that? Nobody would have thought that, right? You wouldn't have thought that. I wouldn't have thought that. And now the loss of chloride is very fast. It's slow here to make a carbocation, but now way over there that a satellite anion makes it now fast to remove the chloride. And I'm going to go straight to a weird looking resonance structure. In other words, let me now use this with that negative charge and now this pi bond becomes very nucleophilic and it helps to push out that leaving group. And what you get is a carbene. That's now a carbene. This is weird. There's two, four, six electrons on this system. It's like a carbocation and a carb anion all on one carbon. And that reacts very quickly with nucleophile in solution. So you can draw it as the sodium ethoxide that's attacking or I'm not going to show all the steps but or ethanol attacking but that is now very quickly attacked. Not on this end but attacked back over here where the leaving group left. And so then you can redraw this and again I'm not going to show all the steps going back to this final product. So how do they know that this carbene is there? Well what they did is they ran this reaction in the presence of compounds that have double bonds and what they showed is they were able to get cyclopropanes instead, right? You can't explain this kind of reaction formation of these products without invoking a carbene. Unless you invoke a carbene you're not going to get to this. So that's how some other major piece of evidence that there's a carbene involved. Okay so very difficult to pull protons. There's not a problem thermodynamically with pulling protons off of sp2 centers. The problem is one of kinetics. So thermodynamically butylithium ought to be able to make things like this simply by deprotonating. With alkynes it is fast enough. You've got a huge thermodynamic favorability for pulling protons off the ends of alkynes and it's kinetically facile. So let me show you a trick, a simple trick for deprotonating, directly deprotonating sp2 hybridized, protons on sp2 hybridized carbons. And it's all about entropy. Well maybe not all about entropy. It's partly about entropy. And the basic idea is this. It has to do with prior coordination. And we're going to see this idea over and over and over again in aldol reactions and enol boronate chemistry. So let me start off by simply laying out a problem, a synthetic problem. And there used to not be a good solution to this problem. So if you wanted to do electrophilic aromatic substitution of phenol for example with a simple electrophile like methyl iodide, how would you do this? So first of all it's not easy to make methyl cations. You can under some conditions do Friedl crafts with methyl halides, but it's not easy to do this. And if you did some Friedl crafts thing, how do you stop from getting the para substituted product? So an electrophilic aromatic substitution, you get mixtures of ortho and para. And so here's how you get around this. The way you do this is you use deprotonation. And you use this oxygen atom in an indirect way to help you deprotonate that CH. So what you do is you first convert your phenol into some sort of an, not an ester, but an ester like derivative. You need something that's stable. So in this case they make a carbamate because the lone pairs on nitrogen are donating into the carbonyl. It makes it hard for things to attack that carbonyl. When you have that nitrogen next door, let's call it a carbamate. And this is one of the better derivatives for helping bases come in. This is one of the better functional groups for helping bases come in and deprotonate that. So when you treat this with butylithium, which is a good nucleophile and a good base, the fastest thing that happens is not for the carbon-lithium bond to attack the carbonyl. That's not the fastest thing that happens. The fastest thing that happens is that this lone pair comes in and attacks the lithium atom. In other words, these things start to associate with each other. And watch what happens when we do that. So there's my butylithium. It's now coordinated to oxygen. And I have to put the charges right here if I want this Lewis structure to be correct. If I put a third bond to oxygen, that's now an oxonium species with a positive charge there. But more importantly, the lithium is now a lithiate. And as soon as I draw that negative charge there, I realize, wow, in contrast to the butylithium I started with, now every single bond to this lithium is now more basic and more nucleophilic. That's what that negative charge tells me. It's now more reactive when it's coordinated than when it's just floating around. In other words, when it's close to these ortho positions, that carbon-lithium bond is now more basic. And so when it's coordinated, you have faster rates of deprotonation than you do when the butylithium is just floating around and colliding with stuff. So this is the intermediate that you get.  So you end up getting this, you know, the lithium that's dangling over here now re-coordinates, so I'm skipping that step. You can fill in that extra step on your own. And so now you get this intermediate that looks like this. And then there's a lithium. So in other words, in the final product, this oxygen is still coordinated to that lithium. And so now when you throw in your electrophile, like methyl iodide, this is very reactive with electrophiles, that carbon-lithium bond. It doesn't have to be methyl iodide, but you could use that as your electrophile if you wanted. So now you use this to attack whatever your electrophile is going to be, there's that nucleophilic carbon-lithium bond. There we go. And now at your leisure, you can hydrolyze that carbamate back down to an alcohol. So this is one common way to make methylation work. You take slow reactions and the simple trick of having a coordinating group that soups up the reactivity now speeds up reactions nearby. So we call that directed. And there's all kinds of groups you can have here. They generally involve, you know, five member, four, five member, six member type ring transition states to bring this basic bond close to the CH that you want to be programmed. Okay, so let's extend this idea of the importance of this type of pre-coordination a bit. What's the hybridization of these carbon atoms in ethane? Now SB3, what's the hybridization of these carbon atoms in an alkene? SB2, what's the hybridization of this carbon atom here in an alkyne? SB. So the more S character, right, 50% S character versus 25, the more S character, the easier it is to deprotonate. The more S character, the easier it is to deprotonate. The less P character, the easier it is to deprotonate. So let me just remind you of hybridization in a cyclopropane ring. When you look at the hybridization, in order to pinch down to make these 60 degree angles, you end up with these carbon, carbon bonds here being about, and SP5 seems weird, it's about 80% P character is the main, I don't even know if I'm doing the math right, but there's more P character than normal in this bond. What's important is if you're using extra P character to make these carbon, carbon bonds, you have less P character to make these bonds outside. The hybridization for these bonds outside is approximately SP2.2. It's closer to SP2 hybridized. Those bonds on the outside of a cyclopropane are more like this. It should be easier to deprotonate cyclopropanes than it is to deprotonate just a simple alkane. It looks SP3, but those aren't SP3. Okay, so keep that in mind. Okay, so we're going to talk about two reactions of oxyranes or epoxides, and let's go ahead and start off with this very traditional reaction. You take an epoxide and you treat this with a lithium amide base, and the question is what happens? So what happens with an epoxide and a lithium? So lithium amide, well, it's nucleophilic, it's basic, but you don't use lithium amides as nucleophiles. I can't think of any case you would purposely ever do that. When you use lithium amides, you're using them as bases, and here's the base-promoted reaction that you see in this case. It's an E2 elimination. Right, there's a pro here. Here's the leaving group. The carbon-oxygen bonds are leaving groups, and there's the proton that gets pulled off. So that's an E2 elimination, and lithium amide is a very powerful base. Here's what's going on in this reaction. In other words, it's not that this lithium amide comes along. What's the most basic part of this? It's the lone pair. It's not the nitrogen-lithium bond. It's the lone pair that's the most reactive part, but that's not the first thing that happens. The first thing that happens is that the lone pairs on this oxyrane come along and coordinate with that lithium. And when it does that, remember, let's keep track of our charge as I now have a positive charge on oxygen. What does that do, that positive charge on oxygen? It makes these carbon-oxygen bonds easier to break. It makes the oxygen a better leaving group. And at the same time that you're making an oxygen better, a better leaving group, let me finish the other part of this, you now make this nitrogen more basic. Every part of that nitrogen atom attached to that lithium now becomes more basic. So this bond is easier to cleave. This nitrogen atom is now more basic. And so now you have this accelerated deprotonation. The important part here about this is that you end up with a, there's a requirement for a syn elimination. And they've shown this by putting deuterium on one side and proton on the other. They've shown that in every case it's the proton on the same face as the epoxide that gets pulled off. It's not an anti-elimination like an E2, so it's not really an E2. E2's are anti. This is a syn elimination. Okay, so that's one reaction of epoxides with bases. And again, it looks kind of like an E2, so that doesn't really, that's not a mind bender. I didn't do a good job of drawing this proton here, so let me redraw that. There we go. Sorry for that crummy drawing. Oh, and I forgot to break this. There we go. Okay, so epoxides, you can do eliminations with them. You relieve ring strain. That's cool. So again, if you were able to resist the temptation to do an SN2 reaction on the epoxide, then that kind of made sense. Okay, let's talk about another reaction. And I'll start off by showing you the observation that led people to realize something cool is going on, something else cool goes on with epoxides and bases. Oh, here's another epoxide. It's not a five-membered ring. So when you treat this with lithium diethyl amide, you get the expected syn elimination product, this kind of thing that looks like an E2 elimination but is syn. Yield is only 16% for this. It's not very efficient. Turns out that the major product in this reaction is a bicyclo-octane system with two five-membered rings. So how do you explain that? There's something non-obvious that's going on. I hope you can immediately see that you're not going to explain that unless you can figure out how to make these CH2 groups on the other side reactive or something so reactive, maybe you're not making these reactive, but you're making something so reactive that it can react with those CH2 groups. That's the only way you're going to make a five, that kind of five-membered ring system. I'm going to redraw this epoxide in a different conformation to remind you that when you have eight and nine-membered rings, there's significant trans-annual interactions. It doesn't look like a stop sign. It looks more like this, and there's very bad bumping. If you have to cyclize an acyclic molecule to make an eight-membered ring, this is going to just screw you. It's going to kill those kinds of bumping interactions. But it also really enhances the possibility that things here will react on the other side. So you can imagine if you have some sort of an epoxide here, and you have an alkylithium, there's another competing reaction, but with things that are basic, amide bases in this case or potentially alkylithiums. So not only does the oxygen coordinate reversibly, but you can also get this deprotonation. Remember the CH bonds on the outside of strained three-membered rings are more acidic than normal, thermodynamically more acidic and kinetically more acidic than normal. And so you end up getting deprotonation of these CHs on epoxides. So you end up getting medallation on the epoxide ring, competing with that ring opening. This is a competitive process that competes with that ring opening. And so here's what I don't think you could have guessed, is that this pops open. I wouldn't have guessed that. I would never have guessed that. That this pops open. And when that pops open, it gives you what's called a carbenoid intermediate. It's not a carbene, because there's a lithium attached to where you would have had a carbanion. So eventually this coordinates with another lithium. Let me just leave that as an O minus for now, otherwise it'll be confusing. So you end up with this species. It's like, oh, it's a carbocation.  Well, but at least there's some, somewhere on here, there's a nucleophilic pair of electrons. So you relieve ring strain. You've got this very electron-rich carbon atom that relieves ring strain. So this is a carbenoid. It's sort of like this. It's not a carbene with an empty p orbital. A carbene would have an empty p orbital and a carbanion sticking out here, but there's no carbanion. There's a carbon-lithium bond. That's called a carbenoid intermediate. If you took away the lithium, that would be a carbene. So let me just label that carbenoid. And as you can tell, it's electron-deficient. That carbon only has six electrons. So these C-H bonds on the other side of the ring are poised to form a bond across that ring. So you add here and at the same time that you're donating into that empty p orbital, sorry, I'm on the wrong structure. Okay, here we go. There we go. So you've got this empty p orbital, very unhappy, very unhappy, take these electrons, transangular interact, and maybe I should readjust the shape of my ring to put these closer. I could reshape this so that the bond, this was, whatever, I don't even think I'm using the right carbon atoms. I'm not going to take the time to redraw this, but you could readjust the shape to where you could see that this is directly across from that. And then this nucleophilic bond at the same time can come and add to that and pull the proton off. You basically do a C-H insertion across the ring with this carbenoid. And who would have guessed that? You could never have guessed that in a million years. That's something where somebody has to show you that and then you go, holy cow, can it do that? Yeah. Okay, so, and again, that wasn't predicted, somebody stumbled on that reaction. Okay, I want to stop and try to debunk a fiction here by, in a disturbing way, by showing you some pictures. I hope I can boot up the projector here. So we can talk about the structures of these things that I've been drawing for you and how it's all a lie and how we're going to deal with that. Oh, cool. Okay, so when I show you these alkyl lithiums and things of that nature, how should we think about those? So I'm pretty sure if you've taken an undergraduate organic chemistry class in the United States that you were introduced to alkoxide and intermediates in a way that looks like this, this is an excellent way for you to help you understand the basicity and reactivity of the alkoxide because you were trained to think, oh, when I see it minus charge, I know that this is basic. And so, what's the better depiction of these? Now, I would argue maybe that this is better or if you get to a case of an enolate, what does an enolate look like? How should we depict these? Let me show you some crystal structures of these compounds so we can get a better idea of how to think about these, not just in the solid state but in solution. Here's the structure of potassium tbutoxide. So over here, if you've been using this depiction, how many bonds are there to potassium here? Zero over here. At least here, there's one. How many over here in the real structure? Three. You know, to me, one bond looks closer to reality than zero bonds, right? There is no such thing as free tbutoxide floating around. There's no such thing, not even close. Let's come down here and look at an enolate, a lithium enolate. We're going to talk a lot more about those later. How many bonds to lithium here? There's none. You know, even here, when I draw this, that's at least better than this. But in reality, you don't have one bond to lithium. You've got three at a minimum here in these types of systems. Here's the oxygen. Each oxygen is connected to how many lithiums? There are three lithiums. And each lithium is connected to three oxygen. This, in reality, are the kinds of structures you have in solution when you stir things around. Every single time that you run reactions and things don't make sense, come back and remember these pictures here. Okay, you might make some argument. Oh, well, of course, there's lone pairs all over these oxygens. That's why it's coordinating so heavily. That's why you get all this aggregation. I've got potassium, but I've got lone pairs everywhere. And the only way to make them happy is to have the lone pairs coordinate to something. So let's go down and look at an alkylithium. There's no lone pairs on carbon, right? When I draw an alkylithium like this, I don't have any lone pairs to talk about. And so how would I think about the structure of alkylithium in solution? In solution, not a crystal structure where you could be biased by some packing forces or lack of solvent. If you put this in THF, this is the structure of butylithium in THF. And there are many studies that show that this is true. And it's actually an equilibrium. It's like, what is going, like, how do you even, let me try to unwrap this structure for you. So each, here's, each butyl chain right here. And each butyl lithium, carbon-lithium bond is part of this sort of cubic lattice with four carbons and four lithiums, right? It's nothing like this, a free carb anion and a free lithium. How many bonds to lithium in the real structure here? There's four. There's not zero, there's four. Now in THF, of course, when you have lots of THF present, there's an equilibrium. You'll see this other just dimer of butyl lithium. But again, lithium in this dimer has four. So over here, you can see each lithium is bonded to three carbons. And over here, each lithium is bonded only two. It's an extra THF molecule that is helping the lithium to satisfy the octet rule, right? The lithium wants to satisfy the octet rule, yeah. What's the charge on lithium and how many male octets? If you do the formal charges here, you'd have minus three charge on lithium. So these are dative bonds I'm drawing. They're not charge-balanced. These are not true Lewis structures. In a Lewis structure, I'd have to put minus three on lithium. Okay, so how do we, let me just help you deconstruct this butyl lithium thing because it's disturbing to see this kind of stuff. And I don't know if this is going to make it more disturbing or less disturbing, but let's try to understand the reactivity of butyl lithium. When you look at butyl lithium, here's what you ought to be thinking. Oh my God, that bond is nucleophilic. That's what you ought to be thinking. And at the same time, you ought to be thinking, what the, this lithium only has two electrons and it wants eight. Lithium wants an octet of electrons just like every other second row atom. And so how are you going to make that happy? What you're going to do is you're going to take this super duper duper nucleophilic carbon lithium bond and you're going to use it to donate into the empty orbitals on lithium. Right, so now that's at least a little better. Okay, that's a little better. Now lithium at least has four electrons, but it still wants eight. And this is what's going to drive other butyl lithiums to attack this. You'll notice in that other structure I showed you, I never filled in the carbon hydrogen bonds. Now that I do that, how many bonds are there to carbon there? Right, if you have some sort of bias against carbon with five bonds, forget that bias. Right, there's nothing wrong with having, we've talked about this before. There's nothing wrong with five bonds to carbon. Just don't violate the octet rule. We have not violated the octet rule. This carbon still has eight electrons. There's eight electrons in this carbon atom and if I take these electrons and I share them between these two lithiums, I'm not adding extra electrons. I'm just sharing those electrons. So we don't, you know, this may be disturbing to you, but we have to get over that. And I'll show you one last picture here before we go back to the chalkboard type lectures, but just to move down a little lower in the periodic table to cuprates. So we're going to draw some cuprates in just a moment, but I want to remind you it's like this alkyl lithium thing. Like if you draw an alfennel cuprate or a fennel copper species, we don't draw it like this when we draw things above the arrow or mechanisms. But this is the structure of a fennel copper compound. Look, I've got this benzene ring and I've got two bonds to copper for each of these carbons. And here's the cuprate. So over here with a cuprate where there's two alkyls on copper, now look at this. It's like each carbon on the benzene ring that's bound to copper is also bound to a lithium atom. Okay, so the structures that we draw, when you draw a butyl lithium, are not right. They're not the correct structures. And I want you to keep that in mind. And I'll tell you how we should deal with that as we go along here. Okay, let me go ahead and show you how I would like you to deal with this. So if you go look up the structure of sodium t-butoxide or sodium methoxide, it's aggregates. It doesn't look like this. And yet, when we do arrow pushing, I want you to draw it as the monomer.   But I never want you to forget that these are aggregated in solution. You're going to be dealing when you do synthesis with compounds that have other oxygens and chelatable groups all over the place. Don't forget that that sodium is not happy with just those two electrons there. So when you draw mechanisms, just to deal with how should we draw mechanisms for things like this?  I don't want you to draw this. I don't even want to draw a regular arrow here because it hurts me to think about this. You're not going to simply have this dissociate into two components. If you calculated using Coulomb's Law what it costs you to pull a sodium away from an alkoxide, that's so energetically expensive it's not realistic to do this. There is nothing you can do with these lone pairs that you cannot also do with these lone pairs. So when I give you a sodium alkoxide or potassium tb-toxide leave it on there and do this, right? We don't have to dissociate the sodium or the potassium or the lithium first. It'll come off eventually. And when I ask you to do this stuff I'm fighting all of your previous training probably for drawing mechanisms but that's too bad. So you'll get an oxonium intermediate. Now you can dissociate the sodium. Now you're not pulling a minus away from a plus and depending on the concentration actually the bromide might come back in first, poke some electrons into sodium and then dissociate but we can simply draw it like this at least now we're not trying to separate a plus from a minus, right? That's what makes this so painful over here at least the most painful to me. Okay, so this is closer to the way you ought to be dealing with these types of reactions. This is the way I would like you to push arrows. Don't pop off the metal from the alkoxide. Just don't do that, okay? So here's what is also okay, what I would like you to be able to do for your arrow pushing. Frequently we'll come across things and it doesn't have to be butylythym, it could be a grignard reagent, right?  This is nothing like what's going on in solution. I just want to use a different pen color to say don't do that. Don't make it dissociate to give an alkyl anion. That's not what grignards look like. That's not what alkyl lithiums look like. If you want to do some sort of nucleophilic attack there's nothing you can do with this lone pair and the minus that you can't do with this. There you go, right? Just use the sigma bond to attack things. Right here there's a lone pair. That's the more nucleophilic component but there's no lone pair on carbon in butyl magnesium bromide or things of that nature. And now you can pick up the magnesium. So this is the way I would like you to push these types of electrons. Okay we don't have time to quite finish up. I'm going to talk a little bit more about enolates, right? I'm not going to, we're in this class, we're not going to draw all these complex aggregates. We're just going to draw a monomeric species. And I'll make you feel a little bit more comfortable with drawing a monomeric species when you draw lithium enolates. So when we come back on day we'll finish up on this and then hopefully move on to alkenes as nucleophiles. Yes?


Oh hoi hoi, and now we're gonna try and play a little SCP containment breach But online I think my best description of secret laboratory in the one time I played it and I Half the time couldn't figure out the controls for it, but in the one time I played it was containment breach but with Assholes, so, uh, let's uh, let's give that a try Hmm You say east official. Well, just go to the for this one, I guess What's the worst that could happen? This is gonna be so terrible, and I actually have no idea if my microphone is gonna be working for them or just for you or Find out one way or the other I understand this game has a lot of waiting involved, but We're gonna still try and see if we can do it. I'm probably supposed to be able to see Just say it's all Ah Some kind of new to this game is it normal for it to just take this long for anything to happen All I've got here is a black screen. Oh Is it truly you? Truly me. What do you mean? But there's the marine Yes, this is Dr. Samarian I'm actually recording this for I'm actually recording this for the YouTube, but uh, okay. Oh Oh It's alive.  I'm doing Okay, hello everyone And now Having trouble remembering to hit shift when I turn right So wait is e the button to activate things yes, got it And run inside Sure, I'm going to screw that up, but all right I'm sure I'm gonna screw that up in the moment, but yes You're probably going to get scared by the peanut because he pops out of nowhere every time By the way, that's alive Peanut 173. Oh, right 173. Yeah, I gotcha. Yeah Yeah, yeah, you know if peanut is alive Dog is alive and 049 is alive. I mean a 939 049. So let's go Vacuation shelter. Yeah, you know that this is a vacation. This is just a dead end. Yeah Yeah, it makes sense Okay 049 is dead 939 is alive Are those the only two we have to deal with or? Yeah, they're the 939 is alive and I mean Gotcha I should probably set this so I could is there like that the way to turn on I'm not gonna do it right now But is there a way to turn on like voice activated this whatever instead of a button? Oh Yeah, no, there's no Yeah, fair enough. That's it This is it again. Yeah, yeah, just hold shift. It's faster. I know I keep forgetting. I'm gonna probably continue to By the way, is there friend is there friendly fire in this game because I was worried about shooting you guys accidentally yes There's only fire, but there's not friendly fire on every server Gotcha, I just wanted to I wasn't sure if I was gonna shoot you so I just let you guys handle that one I've played a lot of containment rich yes, I know yeah, I've played this like one time before I usually describe this to people I usually describe this game to people as SCP containment breach, but with assholes generally You shot it Okay, that's pretty cool Boy, we don't die. Yes, that's generally a good hope Yeah, interesting Oh, yes, somebody's using intercom pretty much it okay We have one minute we should go now we need to run we're going to die. Come on.  Well, it was it was nice playing with you guys. I think I've got enough footage for at least one video there No That that was like that.  Yes, we are dead. I don't know if you can even hear us Yeah, I can only spectators can only hear each other They cannot hear they they can hear others that are alive, but they others that are alive can hear spectators Okay We should have never entered like containment zone I hope we spawn a scales insurgency Uh simerian dr. Simerian.  No Thank you very much for watching If you like the video, please scroll down and hit the subscribe button Then hit the notification bell next to that so you're notified when I upload a new video Then head on over to patreon.com Ford slash D. Simerian and pledge at any level like the people in the screen here already have It's nice to know that I'm not alone out here, and I'll see you all again on tuesday


German Defense Ministry admitted that the Bundeswehr will not be able to protect the country. The Bundeswehr is not able to protect Germany in the event of martial law. The country's Minister of Defense Boris Pistorius admitted, at the Congress of the Faction of the Social Democratic Party of Germany in the Bundestag, we do not have armed forces that are defensive. That is, they can protect against an offensive, brutally waged war, he said. According to Pistorius, Germany needs to invest more in modernization of the army as the country, among other things, has obligations towards other NATO members. The ministers stressed that the Bundeswehr must fill in the gaps that have arisen over the past 30 years. Among the shortcomings in the army, Pistorius listed the lack of personnel, equipment and weapons, which, after deliveries to Ukraine, must be replenished. And no matter how cynical it may sound to some, German weapons are now saving lives in Ukraine, he added. Last week, the German Ministry of Defense announced that, in addition to the 14 Leopard 2A6 tanks that are being prepared for shipment, they will supply Ukraine with four more vehicles of this model. The CEO of the German engineering concern Rheinmetall AG, Armin Papelger, said that Germany had delivered two air defense systems to Ukraine, Skynex and Skyranger, leaving its capital unprotected from air attacks. He also noted that in the event of a conflict on the territory of Germany, the country would not be able to defend itself without the help of the United States, since it lacks everything in all defense areas. At the same time, according to him, Kiev will not have enough tank supply by the West to capture the previously lost territories.


You know, but can we say that at least for right now that the truth is cloudy, can truth be cloudy? Sure. I mean, truth is also, it's also relative. There are personal truths and then there are universal truths, right?  Those are personal truths. They're true to you, but then you have universal truths like gravity, right? And so therein lies the conundrum. Sometimes personal truths can be conflated with universal truths, so we have to be mindful of that. But look, Lou, here, anybody who's in the government, and by the way, they can verify, knows I still hold a T at top secret security clearance. There's a reason. Okay? A, if I, the quickest way for me to have my security clearance revoked or suspended is A, if I provide an unauthorized disclosure, I provide classified information in an unauthorized manner. The other way is by lying. If I lie just like I can't talk about national secrets, I also can't lie to the American public because that also will hold to be held against me for security clearance reason. So I always have to write this very fine line and people just assume, oh, he's disinformation. I can't lie to the American people because I will have my security clearance removed because that is a site, what part of the psychological evaluation. If someone is a confirmed pathological liar, that is an indicator usually of some sort of psychological issues. Those people can't hold security clearances.


Wow, thank you very much Serge Ranganier and Maria Abek for these very beautiful speeches about Project Europa. We will now pass on to the first sessions of this European Theatre Forum under the common title Social Dimension of Theatre and Performing Arts. So let us introduce Ausa Ricard Dottir, Secretary General of IETM, the largest international network in the performing arts, one of the organizations that formed the European Theatre Forum Consortium. She will lead you through the morning sessions of the Social Dimension of Theatre and Performing Arts. Ausa, welcome. Good morning. Thank you very much, Dina and Ian, and thank you all the speakers of the opening sessions. It was lovely to hear the sound of the German language and as we will amongst other things be addressing language diversity. I briefly thought to myself if I should shift to my own mother tongue. But I'm going to save that for later. As you said, I represent IETM, one of the 12 networks which have jointly worked on preparing this forum for the last months. And the important topic at hand now is the one that we all share and burn for, whether we come from the networks, the European Commission, other stakeholder bodies or the sector at large. What makes the social dimension of the performing arts more fascinating now, more pressing and more important to digest, explore and work together towards concrete actions is the here and now we find ourselves within. A theatre that has for the last part been shut down for months, unable to do what it does best to connect with its audiences in the moment via thousands of theatres and venues and site specific locations across Europe. And this is what we are going to discuss today. How do we pave the way for a better stronger social conditions for the European performing arts. And I am happy to introduce to you our keynote speaker of the session, Gordon Tomka.  He is a professor of University of Arts in Belgrade, and his interest relate to the possibilities of crossing social, cultural and symbolic boundaries. In his keynote, he's going to look into the ways theater creates society and solidarity, and all the interesting avenues this open. Take it away, Gordon. Hello, Sam. And thank you to colleagues that spoke before me as a very motivating, inspiring and optimistic morning indeed. Let me share some words with you. It was a cold pre-industrial winter. But the trees cut neatly into logs were burning in his fireplace. His hands were holding a warm mug of tea. Tea that was picked by underpaid serfs and unpaid slaves in some distant lands and colonies. Prepared for him by his servants, just as was the food that his stomach was still digesting with the help of billions of bacteria in his gut. Yet, he wasn't thinking of slaves, servants, forests, colonies or his microbiome. He was thinking about truth and the ways he can take it from the cardinals, from the church without needing to share it with trees, women, bees, slaves or any of the numerous untrustworthy subjects surrounding him. As the warmth of the fireplace was traveling into his body, his mind was traveling outwards into the unknown, colonizing planes he didn't even know existed. His name was René Descartes, and he was alone together. Descartes is the father of an egocentric paranoid epistemology, a way of knowing that tries to know the world without contaminating itself with the suspicious juices of two of its epistemological arch enemies.  Second, bodies of the others. You simply cannot trust them. They're no match for a high quest of finding the truth. So, he trusted his senses just as much as he trusted his servants. However, paradoxically, these damn bodies, filled with liquids, pulsating, flimsy, shaking and quivering, so philosophically incompetent, are at the same time what makes that quest possible in the first place. These bodies kept him alive. Without them, he would be blind, deaf, hungry and cold. But sharing the cogito with them, oh no, that meant not only sharing the knowledge of the world, but also sharing its privileges, and he didn't like it. Everyone has a body, and everyone can feel cold and hunger, so everyone can claim they know the truth. We think, therefore, no, no, no way. So with the posture of the brave lieutenant, he declared, I now enter the theater of the world with my mask on, with my mask on, with my mask on.  Reserved. Reserved for a cold face of the objective scientist, unmistakable design of the robotic arm, absent look of the romantic artist and unbendable will of the superhero. Reserved for pre-stress concrete of a construction miracle, and for judges straight as an arrow. For log frames, matrices, evaluation forms, and application platforms. For everything that is built to last, to stand still, to prevail. Paranoid theater is an exclusive, sleek, cynical creature that dubs everything, but itself. Brave, alone, and against others. Individuality, invincibility, certainty. At the gates of it, crowds gather.  Maybe something like crabs or whatever is on sale. They are confused, neurotic, disposable and exotic. Entrance denied. Paranoid theater has a peculiar relationship to life. Anthropocentric, profit-centric and industrious. Life starts with sowing the seed, they say, with activation, with improvement. Land, women, pupils, citizens, plots, audiences, ideas, all reserves, all fertile, but passive. One needs to get things going with them, you know. But no, life waits for no one. Activation is colonization. Life is very amicable. It likes to hang out with friends. Germination, you know, is only a reshuffling, a reconfiguration, not the beginning, but the continuation. Life forms create more life forms because they can't live alone without others. But in the Cartesian theater, the paranoid theater, life is broken into pieces, dissected, hierarchized, analyzed and categorized, to the point of no return. When objects start floating in the weightless, seemingly material intellectual fluid. Abstract, fetishized and meaningless. Lonesome, de-territorialized and boring forms of life. Burgers, almonds and quinoa are delivered from the sky. Digital data lives in the cloud. Pork, not pig. People choose their destinies. Waste disappears without trace. Perhaps somewhere in the backstage, somewhere beyond the frontier of their private concrete territories. Equally troublesome is the paranoid staging of the society. Society is a neatly arranged collection of individual paranoid projections. Like a chain of fast food venues, people simply spring up in logical formations. Following a formula, respecting hierarchies, protecting paranoid boundaries. Continuous naturalizations of paranoid biological theories. I was five and he was six. We rode on horses made of sticks. He wore black and I wore white. He would always win the fight. Bang, bang, he shot me down. Bang, bang, I hit the ground. Bang, bang, that awful sound. Bang, bang, my baby shot me down.  Can it all work? It can all work. Can it all work? It can all work until the weekend comes. Until the night falls, until the doors close. And the ghosts of the excluded start haunting the paranoid spectator. Because life, life knows no curtains. Boundaries are leaking. Backstages of the world are spilling over. Our living worlds are getting denser and denser every day. Our societies are turning into gated bubbles. The roads we build bring back viruses. Smoke from our chimneys return home. China takes no more foreign garbage. We are encountering the limits of our certainty built on paranoia. An alternative to paranoid boundaries. An alternative to lone exclusive spaces. An alternative to paranoid theater. Do we know a different way? Yes. Oh, welcome to the curious theater. It's a different and undisciplined, brave and fragile. Uncertainly, but trustful. Made of bodies that move, that feel, that reveal. Bodies who come forth, who come together. Bodies that resonate. Eeking eyes and explosive hearts, sincere and utterly precarious. Alive. A pluriverse, a world with many worlds inside. This vulnerable, ephemeral and erroneous creation is not symphonic. It is music made of disagreement and trust. It's the noise of a forest. It's the silence at the crossroads. No universals, no unicodes, no metrics. Symbiosis without management. So curious theater is filled with talking trees, self-doubting critics, permeable mortars, welcoming smiles, migrating plants, inexplicable hopes, never ending deadlines, first texts of unknown playwrights, under research, huge symbiotic creatures, amazing tiny particles and composting piles. It is a slow, never-ending freefall of a snowflake. A silent rumble of moving continents. An invisible yet persistent growth of children. An absent presence of a distant loved one. It's not a freak show performed for the reaffirming joy of the paranoid normals. It is just what happens when everyone stops acting normal and gets theatrical. Light, night, falls on Bristol. At the deserted roof of a city garage, dancers stretch their limbs. Audiences find their way through cars, lifts and corridors into the open air. The rain starts and the dance begins. A wild dance, a weird dance, a dangerous dance. Concrete with white parking stripes, reincarnated as a dance floor. A theater slowly morphs into rave, dancing turns into resistance. It is a dance that transforms lines, dance that demands the space, space for moving limbs, for skins and bones, for breathing, for living. In the messy reality of Cairo and its metropolitan street life, between surprise and enchanted publics and moral control of the streets, one can find a peculiar and thought-provoking practice of open air theater. An artistic collective, Mahatat, knows the streets are overlooked by numerous law and order institutions. So their theater is quick.  All of a sudden, a theater is born. Unconventional, disturbing, entertaining. Nevertheless, it is a lasting and haunting reminder that streets belong to the people, to the laughter, to the solidarity. Finally, in the Colombian rainforest, silence is a sign. A sign of an upcoming danger. Paramilitaries, drug traffickers, gold diggers, illegal lodgers. They look for victims for unexploited resources for opportunities. These gangs profit from fear, from people hiding in their own houses. But not here. Silence they bring is a calling. It's time for theater. Women of this village come together outside their homes and start singing. A choir of resistance. A choir of dignity. A choir of life. Ana Julia Hidalgo, one of the leaders of the group proudly says, if they came to kill us, we will meet them as bodies that sing for life. They are still singing. So these tireless theaters represent a different political imagination. One then counts no losses and expects no wins. An imagination, not an expertise. A gut feeling, not big data. An embrace, not an expedition. Because no one knows exactly how the change will work. Because there are many right answers if there are enough questions. In the curious society, in the curious theater, society is about living next to a complete stranger. Feeling that we are inevitably dependent on others. That sooner or later, more or less often, we will end up in someone else's arms.  Making curious theater work is a work of care. Feeling care, sharing care. In the end of it all, we might learn how to live with bodies of our own and bodies of others together, weird again. Thank you for staying curious. To you, Ausem. Thank you, Goran. Thank you for those strong words, the poetry, the singing. And the food for thought for us in the coming days. I love the vision of the curious theater. Now, dear people, we move on, and we have three equally interesting workshops you can now join.  First up, working conditions in the performing arts. The contribution of the sector to social cohesion, economic development and international relations is recognized and celebrated. Yet, the working conditions of our professionals are challenging these days. And the situations vary greatly from country to country, which today stifles all potential for cross-border collaboration. This first working group will explore the possibilities of an EU-level action on working conditions for artists and cultural professionals. Daphne Tepper from uni Europa will moderate this important session, in which we will hear artist voices. We will learn about the main challenges that have been mapped by the sectorial networks and associations, and we will get to know the visions of members of the European Parliament and representatives from two national governments. This is session one. Session two, they call it co-create now. Young performing artists will shape Europe's culture in the future. And most of them study in theatre schools and academies. Experts from respective universities in Eastern and Western Europe will discuss challenges, too, and chances of international collaboration in higher theatre and performing arts studies. They will sketch developments and focus on current issues like the autonomous Republic of Learning that Budapest students and teachers installed during their recent campaign for academic freedom against the Hungarian government. In their discussion, the panellists will unfold a perspective on the future of higher education of young artists and work out proposals for meaningful European action. This is session two. And then the third workshop. We will discuss access and diversity in theatre and performing arts. How can the arts be more inclusive? We will try to name the challenges and think about funding and policy to ensure access for a diverse audience as well as representation on stage. Moderator Stefan Fischer-Fels from Assatee International will, and this is his words, have some fascinating guests. So these are the three sessions that you can now choose from. And now Tina and Ian will take over and explain to you how all this is going to happen. Thank you and see you later today. Hi again. So this is the point where we can briefly explain how the attendees get to the sessions. So on the forum platform, you have three. You are already in the auditorium. You will find there are three links to the three different Zoom sessions and a longer description of the content and speakers in each session. So you can choose which one will be the most interesting for you. For those following this first day of the European Theatre Forum through the live stream, the three simultaneous sessions will be live streamed on the same page of the European Theatre Forum's website. And the streamed videos of the three sessions will also be available online after the forum. So you will have the possibility to catch up on their content. We will also, as already Alza mentioned, have a FinTech plenary session. So join us at 12.45 to hear about the discussion in each session. And there will be also QA where you can join and you have the opportunity to speak with all the speakers.


I'm Dawn Pinnock and I proudly serve as the Commissioner for the New York City Department of Citywide Administrative Services, more commonly known as DECAS, and I'm so delighted to join all of you for this special announcement. DECAS is extremely proud of the work we are doing to make New York City's fleet safer, more efficient and environmentally sound. That's reflected in safety pilots like the one we're launching today. But before I continue, I would like to first thank Mayor Adams for his unwavering leadership and his support as we explore and roll out new safety features. Executive Director of Transportation Alternatives, Danny Harris, who has joined us today. Our entire fleet management team, especially Keith Kerman, who has been a visionary leader in fleet innovation. Our sister agencies that are participating in the Intelligent Speed Assistance Pilot, including the Parks Department, the Department of Transportation and Commissioner Rodriguez, who's been a long-standing supporter of our work, the Department of Environmental Protection, the Department of Correction, the Taxi and Limousine Commission, Housing Preservation and Development, the Mayor's Office of Operations, and the Business Integrity Commission. I'd also like to thank Lindsey Green, President and CEO of Brooklyn Navy Yard Corporation, for having us in her space today. And lastly, and certainly not least, I'd like to acknowledge our interns from the automotive high schools who are here with us today. They are truly all future leaders. Our city's fleet is critical to the work we do in service of all New Yorkers. With the new Intelligent Speed Assistance, ISA Technology, we can literally put a stop to speeding and making our fleet vehicles safer for pedestrians, motorists and cyclists. When installed, drivers who attempt to exceed the posted speed limit are thwarted by the technology and the car will automatically decelerate. It has the potential to save lives and restrict fleet operators from disregarding the rules. The active ISA retrofits we are adding to 50 fleet vehicles are part of this pilot, and they will help us reimagine the possibilities for the future. A future where fleet operators fortify their positions as standard bearers and set the tone for safe driving in New York City. It's just one of the many ways we are implementing new features and strategies to improve safety behind the wheel. With our defensive driving courses, telematics, surrounding dash cameras and vehicle safety systems, safety is at the heart of the city's fleet. We're already making strides. Excessive speeding by fleet operators is down 52% in the last two years, and injuries from crashes are down 20% during the same time period. We hope this pilot will build upon the success and reinforce New York City's position as the leader in fleet management. And with that, please join me in offering a warm welcome to someone who is setting the tone for innovation in all aspects of city government, our Mayor Eric Adams. We're interns here. Good look, good look, good look, like that. So I say it over and over again about every crisis and every issue that we face in the city, that there are many rivers that feed the sea of these crises. And so there are many rivers that feed the sea of traffic fatalities and crashes. And we have been constantly damning each river. We dam the river by getting Albany to re-institute or to put in place to 24-7 speed cameras. We're damming the river by enforcement. We're damming the river by going after those illegal dirt bikes that are just a terror on our streets. We're removing hundreds of those bikes and we're going to continue to do that. And we dam the river when we put in place technology that can let us monitor remotely if our drivers of our city fleet, if they are actually following the speed limit. Now we're going to improve on the damming of that river by allowing technology to gauge if they're speeding or not. Right now, it depends on the human interaction and sometimes the distractions on the road prevent the humans from staying within the speed limit. But now these new vehicles and this new technology that we're using is going to do just the opposite. It's going to kick and gear and continue to use technology to make it safer to make sure that we're able to lead from the front. I talk about how important it is to have a safe safety behind the wheel of a vehicle. This is another evolution of that. And traffic safety is public safety. Transportation alternative has been stated in this for years. It is a talking point that many of us embrace and to have this part of how we use our city fleet is going to send the right message. Today, the city is leading by example with the installation of intelligent speed assisted technology in 50 of our city fleet vehicles. If this is a successful pilot, we want to see this go throughout every vehicle that we are using in our city fleet. Unlike traditional speed governors, this intelligent governor's piece of equipment will adjust the vehicle speed as the vehicle travels through locations with different speed limits. I was impressed. I was asking a ton of questions like how did we know what's going on? And I was just impressed to see how this technology operate. It will ensure that speeding is impossible in city vehicles, restricting our vehicles maximum speed. It's going to be impossible to speed beyond the speed limit. Even as the speed limit changes from highway to the streets, we're going to ensure that the vehicle stays within the speed limits. Our fleet must always be focused on the road. That distraction is real. And sometime that distraction leads to people speeding beyond the limits. We see it in some of the visual remote technology that we're using. But now we are damming this river even better than what we thought we were damming when we did the first level of technology. And so we're urging New Yorkers to slow down. So we have to start with our fleet first. And we're going to push this narrative of driving slower. The number of real injuries and fatalities clearly you see the correlation between these injuries and fatalities are connected to aggressive fast driving. And we want to make sure that we again leave from the front. This adds on to the river that we're damming about intersections. $900 million, a thousand intersections. The Commissioner Rodriguez already 500 intersections towards our goal. We're sure we're going to reach the numbers that we want this year. But this is all part of how we dam the rivers, including the $4 million in campaign that we're using to constantly inform New Yorkers, no matter what language they speak. It is about how do we ensure safety is safety? No one fills it an easy notification when you tell a loved one that you lost someone due to traffic crashes. We want to do everything that we could possibly do, alleviate if not eradicate those crashes. And this is a mechanism that we're using. I'm looking forward to testing the product as we drive and stay within the 15 mile and hour speed limit here in this location. So good job, Dawn, using innovation for safety is something I talked about over and over again. And now we are moving forward with the implementation of it. This is how you get stuff done, Dawn. Thank you so much, Mr. Mayor. Next we have Executive Director for Transportation Alternatives, Danny Harris. Thank you, Mr. Mayor. Thank you, Commissioner Pinnock. Thank you, Commissioner Rodriguez. Thank you, Keith. Thank you to the entire DECAS team. On behalf of Transportation Alternatives and Families for Safe Streets, this is where we need to be, at groundbreaking and not vigils. And again, Mr. Mayor, under your leadership, we stand together under new groundbreaking, this without hard hats, but with groundbreaking new technology that again is leading the nation. We know that 80% of the fatalities on our roads in New York City occur because of speeding with 24-7 speed cameras. And now with this new technology, we're putting a stop to that. We're ensuring that no New Yorker, no matter wherever you live, from a three-month-old walking with their parents in a stroller to a 99-year-old on his way to a house of worship, have nothing to fear when they cross the streets in New York. Again, it's not just innovation for this city, it's an innovation for this nation. We have shown consistently in New York that whether it's protected bike lanes, whether it's city bike, whether it's 24-7 speed cameras, what happens in New York City is not just saving lives on our streets, but goes on to save lives around the rest of the country. So we look forward to seeing this pilot expand to every vehicle in the fleet and to more vehicles across New York City. Thank you so much for this opportunity. Excellent. Well, they may have some questions on the technology, so why don't we go on to whomever's going to answer those questions? If you have some questions on the technology, why don't we ask them on? Oh, so just walk me through how this technology works. Based on the posted speed limit, how does this technology know what the posted speed limit is in the area? At what point does it stop the cars at one or two miles per hour for the speed limit? Okay, hi. Keith Kerman, the Chief Fleet Officer for the city. So we have telematics in the cars, so we are tracking the vehicles as they drive through the city, and we have the speed limits overlaid over those telematics throughout the city. So as you drive the car, and you know, we set this for 15 mile hour zone, as you attempt to go over 15, the vehicle will not allow you to accelerate over 15.  It's it's what's really doing is it will not allow the car to accelerate once it's exceeded the speed limit. And that's how it works. We've been operating 50 of them for two to three weeks now, so we've already done 10,000 plus miles. We drove here in it, and so far so good. I'm going to have to stay here. You might take that. I'm here for you. So in this initial pilot, we're doing nine different agencies. The Commissioner Pinnock had mentioned those agencies, and we can get you that list. 16 different makes and models. So, you know, obviously cars are designed differently, so we want to test this across a broad variety of makes and models in six types, sedans, SUVs, pickups, vans, and then two types of trucks. So we want to test this in this broad variety of vehicles we have. The city fleet is complicated. We operate over 150 types of vehicles. So, you know, to roll something like this out, we have to be thoughtful and work it through and all the different types of vehicles. Well, the size of the city fleet and the city fleet is going to be decreasing. So it'll be smaller the next time we update on it, but is about 29,400 vehicles in total. About 5,000 of those are off-road equipment pieces, so about 24,500 on-road. You know, lots of what we call the city fleet are things like light towers and generators and forklifts. They're not the on-road vehicles that people associate with vehicles. And, you know, as the Mayor mentioned, we are going to do a test and assessment over the next six months. We've actually partnered with the United States Department of Transportation Volpe Center to do that. And we want, we think this is going to be successful. We may have to do some tweaks here or there. And then we're going to work to expand this technology throughout the city fleet. And to answer your question, exempted currently from this technology are emergency vehicles. And my vehicle at this time will be exempted as one of the use of emergency vehicles. But how my vehicles are used is determined by the police department dealing with the safety apparatus. They make that determination. I have a related question. And I guess it's a question of overall safety for city employees driving. You might think it's a stretch, but I think it's sort of all the same family. You know, a lot of city employees, cops, firefighters, they park in city lots with obstructed plates they use for abuse or misuse. Plackers, they, you know, and obstructing the plate is to evade speed camera tickets, red light cameras, and oftentimes tolls. So I don't know if the DCATs commission or the mayor, if there's any kind of initial enforcement, I know the previous mayor, had, I guess introduced some plan to prevent plackered abuse, but it just seems like it's sort of, you go around any city building, whether it's a precinct or a fire department, you'll see it's like shooting fish in a barrel, obstructed plates, plates that are folded over, literally taped over, or they're misusing placards. So if there's any future plans to better enforce this for city employees to not misuse their own personal vehicles. Yes, and what you do, you do it locally. Every precinct and every command has an ICO, an integrity control officer. We have been underutilizing the integrity control officers. I stated this before, and I had series of conversations with the chief of patrol, Chief Madri, that to ensure our product on the ground is at the level that we expected, it is important to have first front line supervision. And the integrity control officer, they are going to play a major role to do those visual observations, do inspections around their precincts to make sure that everyone is compliant. And there's no reason to have obstructed plates. There's no reason to put tape on your plate and do things that are inappropriate. We have to keep ourselves to our highest standard. If we expect it more from motorists, then we have to live up to that expectation. You can't enforce the law if you're breaking the law. And so it's our integrity control officers that we have had a series of meetings with them and stated that it's time to kick in gear, not need them to be on the front line to make sure our officers are doing what they're supposed to do. For those small numbers that are violated, because I go by priests all the time, I was in the PSA two days ago, none of those places were obstructed. I walked around, I looked at the plates, everyone was complying with the rules. So that new medical minority must understand that they are going to comply. Mr. Mayor, just wondering, you mentioned your car being classified as an emergency vehicle. Just wondering why it's classified that way and also what do you do in general, as far as instructing your detail to prevent speeding? I always tell them to do so because anything could happen in the city any time of night that may cause us to move at a non-traditional rapid speed. If I have an explosion, if I have a plane landing on the river, if I have any type of emergency, this is a real city with real problems and real issues. And I don't need for you to be at the scene saying, why did it take the mayor so long to get there? So we will be smart when we drive with this attachment or without this attachment, we're going to be safe as we move through the streets. But in a real rural like New York, there are moments when we have to get some place in the hurry to make these decisions that happen in the city. In the demo, he got some machinery. I'll be doing a couple of them at his place. Oh yeah, we are. Are we only doing one topic? I prefer not to. Because we got a one o'clock. We came all the way to that. I came from Inwood. You love us. We're going to see you off top, basically.  This is a nice day, I'll play. So you're not going to take off top? So I'm going to do that. Five up. Yes, coming back. New show. New show. Video of this. New show. Exactly. Here we come.


Everybody forced here ripping a box of 20 22 Donorous optic UFC hobby. So it's gonna be for whom on H. Thanks. Who I'm on. Good luck. See some nice color here inaugural edition Always loved seeing some new optic So my house, Juliana, Pena got a Max Griffin rated rookie auto Red Algemann sterling numbered 191 of 199 Carol Rosa Hello Donald Seroni black velocity is Alexa Grasso number 35 at 39 Really Carl? When was that? That was a little while ago, right? Got a hollow Colby Covington. Hello dominators. How's that came out of a young block of itch? Huh interesting Got a hollow Jose Aldo See some more color here last few packs Cowboy Nickname card there some more red this time is gonna be my speed Red numbered 83 of 199 and last pack This is the octagon Jose Martinez and a hollow BJ Penn Thanks again who mon for the order? Get these out to you shortly


I had a number of reasons for being grateful for the opportunity to do this. I think that the air and space forces are crucial to both strategic and conventional deterrence and that I think the mission is obviously the first reason. The situation we have in the world with regard to the threats that we face I think makes it very challenging for all the services but I think that the air force and the space force in particular have crucial jobs to do that we absolutely have to get right to protect the nation and I think given my background in national security that I was posture to hopefully help make that happen to make us more secure. The threat that runs through my career if you will perhaps more than any other is dedication and passion for protecting the American way of life and for protecting human rights more generally. The reason I was inspired to go into the military in the first place and to attend West Point and serve in the Army was the desire to defend freedom and after the Cold War ended I thought we had an opportunity to extend civil society if you will the rule of law more broadly and to be more effective at leading the world in that in that regard. I got involved in some human rights work and some human rights organizations because of that and some people see that as inconsistent I see it as totally consistent I think that that's why we have a military that's what our men and women in uniform our airmen and guardians in particular now for me that's what we're that's what we're trying to protect that's what we fight for and I think that's a noble undertaking you know I'm an engineer among other things and I believe in using data to understand problems and help you get to a good solution and make good decisions so if you look at the metrics for our performance of our systems and the adversaries what they're building to try to defeat us it's pretty clear to me and has been for some time that we need to invest in some advanced systems that are going to sustain our capability to defeat our adversaries. There's been a big emphasis on speed recently but if you're going in the wrong direction going fast doesn't help you and if you're going at a speed that's going to cause you to fall down and and not be able to get up that's not going to help you either. We're not in a sprint we're in a marathon and we need to we need to make sure we're going at a pace and a direction that's going to get us to where we need to be overall and the innovation we're looking for has to come from the operational community and is how they think about how to fight in the future as much or maybe not even more than it does from the technical community in terms of the technologies that they provide. We are in a national strategic long-term contest with a formidable adversary and what you do every day is important to that struggle and I'm very grateful that for all of our airman and guardians for volunteering to come into our military and help us in that struggle and I'll do everything I can to give you the tools you need to do your jobs as effectively as possible.


So I also plan on running for office all of the office actually have a question No, I actually have a good question. Come what another question for you anything else? Yo, big C big chief. Oh anything Hey, please everyone.  Academy's coming the next four days. So yeah My mega Academy Hold on. I know it's gone long, but I want to speak as we're 24 guys So I also plan on running for office all of the office. So if y'all have any questions for me I will accept him right now. Are you ready for sheriff? Why why? What is it? What is the difference with it for a sheriff? What were you saying sheriff and anything else that I feel like?  It's time for me to take things in my own damn hands. Okay, all right I have a question for you.  I have a lot of experience out in the field doing medical work There was no go and I was stationed in Berlin, please do not be offensive mcnoll team How can you be a combat medic with those? No, so anyway, I was out there I was out there on the front lines.  They ain't feeling good Okay, and then you get to the point where people start treating people like locals and that's a big-ass problem to me Okay So we got to do some things to be able to provide our EMS and our doctors with the tools that they need to be able To do their jobs the fullest being somebody who probably spends the most time in the hospital out of everybody else in the PD I think I know they're out there in the running and barrack actually is also up there in the running for that as this is I think I see you'd more than anybody by like Fair cormor do you there to get your stomach pumps and like new hearts? That's not fair And also I have parvo so I have a daily but either way Yes, that's why that's how I feel about Health care liaison any other question by any office. How could there be a health liaison when there's no EMS Well, there will be under my tutelage, but you're what you're his toots. I think he said it's too Um, thank you're so you're saying you're like with the hospital up there as well If you're if you're opening up the apartment no Duncan was implying I was running for health care liaison How would I run for office for health care? Oh Roy? I'm sorry. Why is got crossed there? Oh any other position they all want me asked questions for her answer doggy about that So if the dog if the dog is liberal with a Glock, then yes, I will shoot him. Okay. No more questions What's the rank structure gonna look like in the sheriff's department? Oh, it's going to be I'm still I'm still writing it up to kind of I guess finalize it But some form of a you'll have your sheriff you have your under sheriff and it's gonna be very similar It's gonna be kind of adjacent to the current LSPD rank structure There might be an extra rank in there, but you've got your your deputies that are gonna be parallel to officer I want to have the Rangers as part of the sheriff's office as well It's gonna be a hybrid sheriff's and park rangers office essentially It's gonna spin off of a wildlife cert and maybe some some day You know down the road if that splits off into its own department then so be it But I think that the best utilization of the sheriff's office as is is Having a wildlife cert and then kind of having the Rangers be Just part of the the rank structure of the sheriff's office. I mean, I'll be honest I don't like the rank senior deputy. I don't know why it just sounds it sounds boring and and dumb to me So we might have deputies and rangers, you know I'm still figuring it out finalizing it in my my vision for what the ranks structure would be But overall pretty similar question Corwin. Oh, how will you approach the sheriff title? If the rank is neutered to the point where you're the equivalent of another officer I feel like that would be a a Well, I mean, I feel like that would be a pretty big waste About the equivalent of maybe something more realistic like sergeant or lieutenant. Oh waste What about the equivalent of the captain waste? Wait, what's the question waste? Sheriff chief of police I could work But only it's a your sheriff position All the same rank is better safe. I mean, that's the only thing that makes sense, right? I mean, very realistically right now in a perfect world, you'd have a commissioner We don't have a commissioner But we what we do have we have a mayor who acts as the oversight amongst our all of our departments So really he is our acting commissioner. It just it works in different capacities what we have now But truthfully, it don't really make sense to have the the sheriff position of a department not be equivalent to Like the chief police or you know, if we had a game warden the rangers office And we had any other department where it's the Top of the rank structure for it to be equivalent as it is in most cities Actually in a lot of cities sheriff is higher, but I don't think that should be the case What are you gonna do about all the sand in sandy shores? Well, make sure there ain't no damn marijuana in it Well, you can't grow marijuana in the sand. Oh, they found a way. I don't know how but they found a way They felt a way to do a lot of Shorty anything else actually I have a question. No, actually I have a good question cornwood another question for you Okay Who wants to be a volunteer for my example who can take a beating here?  I'll take it. Not as your max. I'm bad maple. It's going into some trouble in the LSPD He's not he's not looking too good chief barrack and she just chief Ruby are sort of they're not they're not really seen His his worth right they're kind of seeing him as like this an officer and whatnot have some criticisms Some unnamed criticisms that I'm not gonna make up you can use your imagination and you you don't see it that way You think maple is one of the best and maybe he should have a rank of a ranger or lieutenant or sergeant within the BCSO Okay, how are you how are you gonna have this conversation with barrack?  How are you gonna convince him otherwise that maybe the maple has some better off over in the Blaine County?  No, I literally just said it's all up to you talking to bear So it's all up to him. So you're just gonna let him just well No, but here's the thing at the end of the day at the end of the day It's all up to you on what you want to do with maple here in the LSPD But if you don't see a position for him that I can see him doing up in the sheriff's office really damn well Then if you're willing I'd like to have him transfer if both of y'all want to if he wants to transfer and you're willing to let him Transfer then I'd love to have him because I think he you could do a hell of a job up They're doing specific role that I have for them as simple as that and you have a conversation Well Eric says, you know, I can't really stop him if he wants it if he wants to transfer I can't really stop him But he also doesn't like the fact that maple is going to get this rank just from transferring How are you gonna mend that wedge between the BCSO and the LSPD that is being created right there? Well, I mean it's simple. Okay, Barak, you know, I'll ask him right now. Barak. Why do you not like maple? Let me just make something up Okay, so you don't like his hair. Okay.  It's imaginary You know, don't worry.   Why you can't you guys work together on this wait? Well, Barak and I did work together on it. Look how it looks. Okay perception. Okay, who's complaining raise your hands I could give a rebuttal to that.  Who's complaining in this hypothetical Johnson and Aiden Okay, so yeah, I'm complaining.  Okay. I understand y'all are frustrated But there's a reason why I see maple in a specific position Well, I got a specific role for him if you got a problem, okay And if there's something specific with specific reasons you can come tell me about it Okay, but truthfully you don't see everything that I see. All right Just like I don't see everything that everybody else sees but bottom line is this if this is a vision that I have for Something if this is a vision that we have as a command as leadership then we're gonna go forth with it and Barak says, you know Like he didn't really he didn't really want this to happen, but it was out of his hands at that point Well, that's a that's a very important issue. Yeah, so how do you solve that and also flop with your rebuttal? Oh the rebuttal and it's zero disrespect to any it's a Barak in particular But the vote brought him to the position he's in from senior I feel like I feel like a lot of the PD was sort of inundated with the idea that I you know What changes of department and changes of structure people are gonna be in different positions Yeah, I mean yeah, that really has a man's a good point, right? Like I mean you don't just because of the change department don't really mean anybody's changing getting promoted or demoted off the rip, right? Some people inherently might but uh, I mean it's just like everybody else who's gotten promoted, right? Good night, McNulty. Good night, McNulty.  What are you gonna do about the people who are gonna obviously transfer for rank chasing? Because it's a brand new department with no sergeants no tenants, you know free real estate I can I can sniff out rank chasers like my own shits. Okay, every rank chaser in this room I'm not gonna do that. Actually, you know what? I'll tell you right now I don't think a single person in this room is a rank chaser. In fact, I'll go as far as in I think we barely have any rank chasers across old PD. There's a handful of them But some of which actually I ain't even seen come around very often no more probably because they didn't get their damn rank Yeah, oh Call them out. I think there's no need for that. No, I think you should come on I don't think we need to press this any further Yeah I'm gonna not do that because they ain't here to defend themselves a and b it don't help nobody, you know But I do know that there was no your response.    Oh Yeah, of course I pledge allegiance