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(20 points) Draw the product(s) of each SN rection shown below. For cach pair 0f reactions indicate which reaction would occur at greater Fate and explain why (assu...

Question

(20 points) Draw the product(s) of each SN rection shown below. For cach pair 0f reactions indicate which reaction would occur at greater Fate and explain why (assume all reactions occur the same temperature and concentrations of reactants).CH_CH_ONaHzOCH_CO_NaHzoNaCN(CHslzCoNaCN(CHs)zCo

(20 points) Draw the product(s) of each SN rection shown below. For cach pair 0f reactions indicate which reaction would occur at greater Fate and explain why (assume all reactions occur the same temperature and concentrations of reactants). CH_CH_ONa HzO CH_CO_Na Hzo NaCN (CHslzCo NaCN (CHs)zCo



Answers

Draw the major products obtained from the reaction of one equivalent of HBr with the following compounds. For each reaction, indicate the kinetic product and the thermodynamic product.

This is the answer to Chapter 21. Problem number 46 fromthe Smith Organic chemistry textbook. And this problem asks us to predict the products of three reactions. Um And so at first glance, the first thing that I see here is that each of these is the formation of a vinegary agent on then reaction of that vinegary agent with a court Neil compound. Um And so, uh, we should remember from this chapter that, uh the way that the book likes to form vinegary agents here is to react in alcohol. Hey, lied would try fennel phosgene on. Then treat that with beautiful lithium to get to the active Vidic species on. Then react that video species with a carbon compound. And indeed we see for each of these reactions, uh, it's it's literally that it's treatment with trifle phosgene followed by treatment with beautiful idiom, followed by treatment with a cardinal compound. Um, and so each of these products is going to be the out keen formed Bye reaction of the vig made from our starting material, um, and the carbon Neil that is always listed as the third re agent for each of these problems us are bearing that in mind that I'm a pretty much just becomes, ah, filling the pieces type deal. And so one strategy to approach this might be just too right. Um, the algal hey, lied the alcohol group from the alcohol hayride That's going to end up contributing the left half, as you might think of it of the product, um, and then writing Ah, the piece that's going to come from the carbon you'll compound. Um, so like that, uh, and then just just connecting them with a double bond. Um, and so that's one sort of easy way O r shortcut to arrive at these answers here. Once you've identified that, that's the process that that's going on, that it is formation of a video, ge Um and then just ah, video reaction. And so we can do the same thing for each of these one thing to bear in mind if you d'oh choose two approaches this way eyes Just that you're always going to lose. Ah, hydrogen here. Um, so you can see it's ch three ch two in the starting material, but ch three c h in the product here. So that is one thing to just just be mindful of as we solve these next two. And so using that, that same approach be is gonna look like this Eso there's the portion that comes from our starting material, and we can actually write that out of a CH if that makes it easier. Um, And then the portion that's gonna come from our third re agent in this sequence that were given, it's gonna be see age ch to see age too. C six h five c six each five. Um, and we can just connect them with with double bond there. Um and we should also note we're going to get the e and the Z I summer's here, So e n Z um, and of course, in a that's it's not really an issue, since the the right half of the molecule has identical substitue INTs. Um, so easy. You're gonna walk the same. There's not gonna not gonna be a difference there. Um, okay. And then for C, um, it's just gonna be more of the same here. So we're gonna form the video from our starting material and then reacted with this carbon Neil that were given is the third re agent s o following that seem sort of methodology. So, um, here we can just put ch uh, that's easier than just leaving it in. And typical line notation, um, and then we can draw again. The right half that's gonna come from our coward annual compound re Agent three. Here, it's gonna be ch ch two ch two ch three teach to see h two c h three time and again, we're just gonna connect these two by double bond. Um, and again, we should note that here is Well, we're going to see both the e and Z. So, sis and trains stereo chemistry around that double bond. Um, yeah. Okay. And so, uh, again, I think the key to solving this problem is just to look at the re agents and recognize that each of these is the formation of a vig, and then a physical reaction. And then once you've done that, you know that the product of vinegar reaction is always an AL keen. Um, and you know how the two pieces of these molecules his product molecules should be joining up so you can just draw out each piece and then connect them by a double bond. Or however it's easiest for you. Uh, yeah, but so that's the answer to Chapter 21. Problem number 46.

Yeah. Say this is over Timing having the structure. Thank you people. And see, it's three and meat on Bennett's. So we look at the molecule this part to know anything Can you paint from everything from your area? So you really should be one of the starting materials. So on this side, we can have on approximately and even look but a nuclear fuel. Qatar from the night is in on this company government. That's right. What? We You have yourself speed. Oh, a d a living look over there also So on This can be a pain. No, a positive When they started with, he's also we can think off from that a single for 18 that we want for on then this can be obtain from for giving. So this we can start from, uh, see, it's three seeing everyone home. Oh, lately you can drag with the boy G minus which will abstract this problem or itchy Do you think problem here which and But then you lose this, uh, see all you can. Bye. Yeah detail commit no living. See, It's cool. Great vote in one step. So with introduces here to group here so that gives. Oh, you did? Uh huh. Seemed everyone hold. It's No, this is the no treated with Yuria. I know it all. So is it collapse here? I'm at this living group. The writing the same thing in day amendments to us, everyone more. And it's too. And it's the usual, but cool me. So this money, we need more changing my old T minus mhm living eminence. And it's too. I see a job. No, no. Again. Yes, it does. When this company no inserting a day Secularization of the molecule. All right, boys. So this man, a deep throat condition will give Yeah, and it's Yeah, or age now, this problem being highly acidic. 80 minutes A model of water bombing, living timing That's mhm the knowledge

Here the cushion is draw the brothers fold in the aviation initiation. One step is gone. That is an inner Brennan conciliation. Foster on in debt Benton Dozen impurities fault. So this man's in days a link. Larayedh is actually very useful agent for the profession off all plus Ofcom bones you know it against. So here in every case, first step is for mission of benzene disintegrate. And second is it is student with some agent on by the new class our company's fault. So the first kiss, the product for these when it is stupid would see you were Finally benzene does include rate. This managed to grow is replaced by beer and Bruno avenging his phone. In the second case, first step is again for mission a lens in dazzling parade on. In the second step, it is treated with water and by dead three normal. It's different fault. Maybe so. Oh, so this managed to discovered drug Julie mentioned as a nuclear it first and after that district list, by which group and an order go, are the matter position really mean c? It is not just in gear, so see all other crops wilting in scene in the credit, but and it still is blessed by a flurry. Soon the burden is after these two steps. Flooring in pencil vintage, too, and a better position. Me talk. Single women see in the last one, benzene does a new glorious taken to Rome, agendas included on dhe. It is treated first, see you see, and by their CME group is introduced into been ticking and after that reduction is sticking his body into a new migrate. And what so the final product should be? Ben Genting here in tribute. See, it's two and two after the reduction off, seeing goop and and Dr Position Clothing, which was present in the tent. Leniency. So these are the final products phoned after this to stress Parmesan. Benzene doesn't operate and treated with Sandy.

Hillary when they were doing chapter eleven forty six. And this problem asked us to determine the products of a two D and indicate the same chemistry slips her with a So, eh, we have this. I left your foot compound. We know that this is Elektra. Found Why, for two reasons while they're leaving, rebound on it. So we know that unnatural file needs a leading group Two actors Electra file into. We're adding a card on which is very, very, very include Felix. So right away, we notice the nuclear file. Therefore, this must be the electoral file, so we can imagine that that's what we have. We have a leading group bound to this carbon. This karma's a primary carbons with two of these bonds being Caucasian. Deterrent is just I still partition with two new chance. She's sorry. One neutron to make massive, too. On DH. We have won our group, which is a non hydrogen and non hygiene isotope. Adam. So we know that s into mechanism can be allowed here following Garson to us and one rules. So we know that we can do one hundred eighty degree backside attack to make a new bond when you make a bond, you know, breakable. So the chlorine leaving group will fall off. Remember, Ki distinguishing feature in S and two mechanism is that you have an inversion of stereo chemistry. So how do we invert the steel chemistry here? Well, we can draw the product of a as one, two, three, four, five We have five carbons and now the chlorine is gonna be replaced for our new nuclear fall. Get this chlorine, um, byproducts here. But we needed to invert the stair chemistry's how don't commune risk their chemistry while changing the positions of any two. Adams on the molecule will invert your Sarah chemistry. So how I like to do it is I have to change the Adams or the substitutes that are coming out of the pages of wedge and into the pages to ashes. If you just change these two positions, you will invert stand chemistry. So in the study material, Hye Jin's coming outs, that means in a product deuterium should be coming out. And in the spring of two of the terms going in, that means in product, Hydra has be going in. So it's our substitution products here and B once again, You have similar reaction mechanism going on here. But if you guys Comptel, you have a cardinal kind a carb carb. And I am here being in Nikola Fall and you have your left foot carbon. So if I were to make my ass into reaction here, I'LL get the product of B one, two, three, four, five. But now the chlorine would be replaced for my nuclear fall. And then But here's the thing. Remember, too in a virtual state of chemistry changes substitutes off to change location of two substitutions. Well, that's on ly the case for Carl Carbons Carl Center's order Carl Carbon is our Carl center is is a carbon with four unique subsections so determined haijun are unique. They're different from each other on this guy here is unique to the corn is unique but and b, we have two hundred attached to this actual Philip Carbon. So this is not a Carl center. So there cannot be any inversion of chemistry stare chemistry here because there is no Syria chemistry here. But what does exist is we retain this their chemistry of these substitutes that downfield on the molecule because they're not involved in any chemistry there. Just hanging out here while all the chemistry is going on. Is it the terminal end of this molecule? So, see, let's see what we have. We have in a park side was equal protons in east side. And we have a strong nickel Follow carbon ionic al kind. So well, we can do is we can identify that the nuclear file will attack on opposites sides are Parkside and it will attack on the least sub student sides. So in this case, both of them are equally substituted so we can attack from either side. Equal probability. So they're here. We make upon you break upon. So this optional pop up hydrogen and water will pro Nate this oxygen to make an alcohol. So now we get or alcohol here and then you get Unical follow task here and then what you'LL get is and inversion of stare chemistry. Actually, So what you're doing here and she steers countries not inverters retained because it's not actually an s and two mechanisms. So hydrogen on the scientists here was carbon is here on this side. You have your method group in hiding down here. So this is one product, but with equal chance. Your card and I own an attack on this side making a bomb. You make upon you break a bond just gives old minus bo minds will be probed Nated bye water given alcohol and you get your AL kind product here, Then you get your methyl group coming out of the page, your highs and going into the page inside. Same thing. Imagine coming out of the cage metal going into the page. But if I want to flip this molecule around, I would see that I just formed identical structures to this. So these two products are identical. There's no difference between them. You're identical. Doesn't actually matter what so this attacks on. So now let's see for this example here. So once again, we have a coolant carbons. So fifty fifty chance you can't talk on this side or the side Really plump side. So if he attacks on the blue side, do you get the blue product? Remember your stare. Chemistry's retained and then on the green side and get on the green side. You get the green product. So now he may be a one ramble are these? The same products are these, and an tumors are where this world this is where your molecular model kids come in extreme use. So if you were to draw each of these and you flip them such that you're all kinds would overlap. So if I would take this and I would flip it such that this is all coming over like this one, I would see that when I flip this This carbon originally is coming out of the page. That means after flip it really going into the page. And it's sort of reporting this. So and the blue Carmen's coming out of the page. But when I flip this Cartman, we're going into the page. You can see the hygiene were coming out of the page while this hydrogen is going into the page and I would've flipped this side, this molecule, this molecule with carbon coming out of the page, methyl group coming out of the page. But flip it. They know they're going into the page, but in the blue it's coming out of the page. So clearly is a non identical, non super possible mirror images of each other. So these are what we call in an tumors, so their unique stare products


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