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Sure aue Your answets Lleony eacn proulem numtider. For each problem, design synthesis_ showing all of the reagents and products along the way_ You may use any inor...

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Sure aue Your answets Lleony eacn proulem numtider. For each problem, design synthesis_ showing all of the reagents and products along the way_ You may use any inorganic reagent and any organic reagent of two carbons or less_ONE STEP SYNTHESIS [20 points] Choose any FOUR of the five problerns below to answer. (Answers beyond the fourth do not count:)TWO STEP SYNTHESIS [10 points] Choose any TWO of the three problems below to answer. (Answers beyond the second do not count:)THREE STEP SYNTHESIS

sure aue Your answets Lleony eacn proulem numtider. For each problem, design synthesis_ showing all of the reagents and products along the way_ You may use any inorganic reagent and any organic reagent of two carbons or less_ ONE STEP SYNTHESIS [20 points] Choose any FOUR of the five problerns below to answer. (Answers beyond the fourth do not count:) TWO STEP SYNTHESIS [10 points] Choose any TWO of the three problems below to answer. (Answers beyond the second do not count:) THREE STEP SYNTHESIS [10 points] Choose any TWO of the three problems below to answer. (Answers beyond the second do not count:



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Outline a reaction sequence for synthesis of each of the following compounds from the indicated starting material and any other organic or inorganic reagents needed. a.CAN'T COPY THE FIGURE b.CAN'T COPY THE FIGURE c.CAN'T COPY THE FIGURE d.CAN'T COPY THE FIGURE e.CAN'T COPY THE FIGURE f.CAN'T COPY THE FIGURE

This is the answer to Chapter 11. Problem number 61 on this problem says, devise a synthesis of each compound from ethanol as the only organic starting material. Ah, and we're told we can use any other re agents that we need. Ah, And so for a, um, we are trying to get two this al kind all and so we're going Thio have to build ah, carbon chain on install functional groups at the proper locations. Okay, so to get started, um, we can do it on elimination reaction here s so we can use concentrated sulfuric acid and he, um and that is going to give us just this Al Keen. So I've seen, um, we can then Bram innate that using elemental bro mean you are, too. That's gonna give us to die, bro. Mo compound. Um and we can then treat that with two equivalents of sodium a mine, uh, to get to e al kind. Okay. And so now, from the al kind, we can start building, um, the rest of this molecule building the carbon chain. And so we can de protein eight with sodium hydride to get, uh, the satellite I on on. And then we can, um, use ethyl bromide. Ah, and I guess I should include I'll put it, put it down here. This ethyl bromide that we're using, uh, could be made from ethanol and PB or three. Ah, and that will give us Ethel Bromine. So it didn't say we were only allowed to start from ethanol. So there is a way to make something that we need from ethanol. Um, okay. Ah, So once we do that, we're gonna have this. All right. So, um, we can now, uh, d Protein ate this again with sodium hydride deep, roni, uh, and then used that satellite eye on as nuclear file to open this up oxide. Um, and then protein avian pox I water. Ah, and that is actually going to get us to our product. Um, so there we go. There's our product. Um, And that a pox side that to carbon a pox side there we could make from ethanol like this. There's our ethanol home. Ah, doing elimination, Consul, Ferric acid and heat. That's gonna give us the l keen treat that al keen with, um bro, mean, but with some water in it to get the addition of a bro mean And, um, an alcohol. Um, And then if we treat that with a strong base of sodium hydride Well, deep throat, Nate, the alcohol on it can attack and displace the roaming. And so that's how we're gonna get thehe Parkside that we need. Okay? And so everything is made from ethanol here. So then, for port B is his problem. Um, for part B, we are going to follow. Ah, um similar. Well, actually, we don't We don't really need to follow anything. So for part B, we can start from the product from part, eh? So we just went over how to make this. So this is the products from part, eh? Um and yes, I'll label this from a Yeah. Ah, and so we can just d protein ate this alcohol with sodium hydride. Um, that's gonna give us d protein ated alcohol. Now, if we react that with the effort Bromine that again, Uh, I went over how to make in part a of this problem. Uh, we will get the ethyl ether here. Thank you. Okay, So there we go. There's the answer to port. Be again. We started from the product from part A there. Ah, And then here's part A. We made a couple of things that we needed from from ethanol. Um, and used several reactions that we've learned in this chapter. Ah, and that's the answer to Chapter 11. Problem number 61.

Okay, This problem is asking us to synthesize thes products from my starting materials. So let's go ahead and start with the very 1st 1 So this very 1st 1 I recognize that I have a broken here. And then I formed an l came here. So the thing about that all keen is it's not particularly substituted, right. We only have to Hodgins associated with this carbon on the O'Kane. And then we have this carbon associated with this carbon on the key. So it's only a mono substitute, okay. And generally, with the formation of Hawking's in elimination or actions, I form the most substitute. Okey. So when I formed right here is not a very subsidy scheme. And we know that because my bro minutes attached to this carbon get If we're direct this with sodium hydroxide, for example of most likely forming cocaine right here, that would be a dice up signal came that would be the major product. So when you want to form a at least have a reaction that incorporate this model subsidy scheme and generate, that is as a favorable reaction. So also, judging by the fact that the last couple pages in the textbook at the last couple problems have been dealing with health and eliminations. I'm gonna do exactly that. I'm gonna wreck this compound with extra connected to 123 method groups fit. And by doing that, this next Gen will perform a substitution reaction. It will go ahead and attack that carbon, replacing that bro me. OK, it's just a substitution reaction. So what that does is it forms this ch three safe to ch two. And instead of that broken cakes to my carbon, I now have next gin with 123 method groups with a positive charge of nitrogen kit. And then, of course, I have the remainder of my compound street. Okay, so now I'm at my Hoffman inflammation point because I can just react this compound with silver oxide in water and that's going toe form a high drops that I am to be, ironically bonded with this compound right here. So let's go ahead and act out with silver Roc side A G 20 and water. That's conformed, they say. Was that compound the only difference being that my hydroxide is now ironically bonded to it? Okay, so let's go ahead. And to put that and then one would do is at a hydroxide ion right here. Okay, now I'll have to do is utilize heat. He is going to facilitate the Hoffman elimination reaction in which I d protein ate the carbon with the most Hodgins in the beta position. So this election right now, we can consider that Adam number zero. And then, um, here we have Alfa carbons, which are one away from that and then one away from that awful carbon right here and right here are my beta Karpin's. So this hydroxide is gonna go ahead and deep pregnant the carbon with the most number of hydrogen, which is this one and that will form my product. Okay, what about this one? So this one, Same exact thing. We recognize that we have a natural compound and we have this basically stretched out carbon train. Right now, that carbon chain is in the formation of a rain. We want to stretch it out in order to form that linear structure. So what I've been doing is recognized that I already have my 1234 carbons. And in my product, I also have 1234 apartments. So what I need to do is get rid of this nitrogen hoops is get rid of this nitrogen and in the process makes him double bonds. Okay, so what I'm gonna do is react this with C h three I in excess. Okay. And I'm gonna do that in basic conditions. It's OK to see or three. Okay, that will form it. This product, that should be a four carbon compound. Okay. And then I just had to methyl groups to it with a positive charge. Okay, so the purpose of doing that is to for my ammonium, so that can proceed with Hoffman elimination. Okay, so what I'm gonna do now is reacted with a g 20 and water, and I'll just do this on state. Same step with heat, and that's gonna form this. It's gonna go ahead. And deep protein ate my beta carbon, which is this one. So take off the hadron, move the electrons onto this bond and move the electrons onto that nitrogen to form in this compound where I have my O Keane here. The remainder my compound. So should be like should be over here. I'll just reach all this. So there's my talking. Here's my compound. And then the connection to my next year with 12 methyl groups. Okay, Right now, this what I just right here is not the same as this. I still need to get rid of that extra, because I still need a double about here. I still need to get rid of this nitrogen. So what I'm gonna do is same exact thing that I did before. I'm gonna racket with ch three I in excess, or just see FBI in general to make another method group there to have a positive charge. And then we can proceed with another Hoffman elimination. So that could take off you 100 on that to make an O Keane there. Right? So what I'm gonna do is ch three. I that's gonna add a methyl group to see history. I So I have now is the same thing just with an extra method group. So that means that I have a positive charge on the nitrogen and then using a G to wealth. So we're oxide in water with heat. I'm gonna go ahead and take off this 100 moving the electrons onto here and then moving on the electrons on that I just didn't as a leaving group, and then I should form my product, okay?

So taking a look at retro synthesis again, we describe this in the previous podcast were often given a target molecule on. What we needed to do is break it down into fit sentence, which are chemically non viable materials on. We then try and, uh, ground these materials in real life chemistry where we produce real life starting materials that we can react in order to generate that target molecule. So alcohols are important for organic compounds. They have the hydroxyl functional group, so we can easily synthesize and alcohol using green yard reaction. So we have the preparation off alcohol's using on Green Yard free agent so we can take a look at the first example here. So we have our starting material treacherous and data Caro you make are cut MGP off. That is our Green Yard re agent. However, we'll start with Ph we are. Then we will have pro for now. We'll start with Prepon one off. So taking a look at the second example we have here aromatic carbon I'll so firstly we have the on oxidation step to generate alcohol functional group. We make our synthetic cut, Then we generate our materials so we can. We've got a green yard re agent M g p r. And we also using formaldehyde. In this example, I was all starting materials taking a look at the next example will draw out starting material first. So what we'll do here is will make to synthetic cuts will cut off both of our being on groups. Of course, we have a green yard re agent in GPR. So looking at our final example here, starting off with an aromatic we'll make our synthetic cut here, draw retro synthesis sorrow. Then we draw Green Yard re agent M G P R, which will start with the female rang with the bro Mean attached on. We will need to introduce M g to the reaction vessel. We also need this alga hide on our actual starting materials will look slightly different to our sin. Thens the b r on two missile pro Plan one all

So we were taking a look at retro synthetic reactions are essentially given a target molecule and we're just having to like backwards. So we take a look at our first structure, my gosh, and that it can't draw actual synthesis. Arrow on. Now we draw our components where we have two missile Prepon, One island Bremer bending so sort of re agents that we're gonna be needing here is we're gonna be needing MGI andi e t 20 for this conversion to get to Phanom, magnesium bromide, new P, C, C and C H two c l to to get from our alcohol to our alga hide. Then we react these two together in the presence of e. T 20 on h 30 plus a Proton source than in the second step. We have PCC and ch two c l two. So in the next example we have we're making to synthetic cuts. It's moving straight onto our next example just to save a lot of time here. We've already discussed the sort of re agents that we need for these types of chemical reactions. So all we're going to be focusing on is the structures themselves to make us. And that's a cut green yard region on. This is generated using a alcohol starting material. Andi was a starting material. Also contains an alcohol. So I just chemically transforming our starting target molecule that we have into a primary alcohol. Because we can't achieve this chemical transformation here in Rabat to make a make or chemical cook. Now we can think about drawing are starting materials by one of our starting materials is in a box side. You just insult in a page and then on to our next example here in first of a chemical transformation into an alcoholic and we make our synthetic cut. Now we'll draw our materials ended up oxide. Well, we've seen this step before. We go from magnesium burn mind to just a bromide containing molecule. And then we used the alcohol form. Next example make a synthetic. It draws retros. And this is our Oh, and now we start to look at starting materials that we could use and this chemical transformation. So we know that we have to work backwards. So we start with our alcohol containing structure, convert this to grow me and containing structure that we combined to our green yard with the other material. We start with our alcohol containing structure and then we convert to Akita. So we have the next reality. Firstly, the chemical transformation from our key tone Thio alcohol We don't make a synthetic cup Another retros. And this is Sarah. Now we have our starting materials, but we need to work backwards for me. So of course we go via remain containing compound and then the alcohol containing compound. So this whole group was replaced with an alcohol group. In this the material that we have we are working with a primary alcohol final example. I believe we have a molecule that contains a foreman atom. It contains our benzene ring. So the first thing we do we draw our structure with appropriate functional group make us and data card here we're making to on our hydrocarbon chains. Well, as always, we go via berman containing molecule on any alcohol containing molecule


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