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Propose synthesis for ONLY THREE of the molecules below. Your carbon source must be 6 carbons or less (benzene is okay), and reagents added along the way may only h...

Question

Propose synthesis for ONLY THREE of the molecules below. Your carbon source must be 6 carbons or less (benzene is okay), and reagents added along the way may only have one functional group_ Draw a circle or box around the synthesis you want graded. More than one step will be needed (24 pts) NO2NHzNHz

Propose synthesis for ONLY THREE of the molecules below. Your carbon source must be 6 carbons or less (benzene is okay), and reagents added along the way may only have one functional group_ Draw a circle or box around the synthesis you want graded. More than one step will be needed (24 pts) NO2 NHz NHz



Answers

Devise a synthesis of each compound using a Heck reaction as one step. You may use benzene, CH$_2$ = CHCO$_2$Et, organic alcohols having two carbons or fewer, and any required inorganic reagents.

This problem asks us to synthesize each of these six molecules. Um, and we're told besides inorganic re agents, we can use hydrocarbons and hail IEDs with six or fewer carbons. Ah, we can use this metal vinyl, Esther. Um, and we're told that each synthesis has to use at least one of the carbon carbon bond forming reactions from the chapter. Okay. S o for a at to start will start from promo benzene er, and the first thing to do would be to nitrate the broom of benzene. Ah, and so nitric acid and concentrated. So fear Gassid is going to give us the nitrates in product. Okay, um, and when we reduce that s o hydrogen gas and palladium on carbon, when we reduce that, we will get the mean. So there's no good way to directly adding a mean to an aromatic ring s. So we had the nitro, um, group and then reduce it. Okay. S O. Now, if we treat this with sodium nitrate Ah, hydrochloric acid and then water. Um, we will replace the mean with a hydroxy group. It doesn't look good. Yeah. Okay. Ah. And so from here, um, we're gonna want to install arm Ethel Esther. And so to do that, um, strong base. So ah, sodium hydride to de protein ate that hydroxy group on and then methyl iodide to make the methyl ester. Okay, Um, now, Ah, as the problem says, we have to use one of the carbon carbon bond forming reactions from this chapter. And so we're going to make the lithium cooperate here in. So in order to do that, we will treat this molecule we've just made first with lithium metal. Ah, and then copper. I died, OK? And so, um, what we get from that is actually gonna beat this. So there will be two of these on a copper lithium center. Um, and now we just need to add the rest of the molecule as the alcohol. Hey, lied. Um And so, uh, the rest of the molecule looks like this. So 1234 23456 with a double bond here. Um, and so that's gonna be our carbon carbon bond forming reaction from this chapter. 123456 Okay, um And so the last thing that we need to do, um, is, uh, hydrate that Al Keen. And so to do that, um, we want the TV alcohol on the interior of molecule. So we're looking for the more Kafelnikov product here, and so we can just use a sulfuric acid in water. Yeah. Okay. Ah. And so we also should know that we would get to an anti murders here. Ah, and that is the product that we're looking for. Okay, uh, and so that's just a There are five more parts to this question, and so I am going to try to speed up and talk a little less and just draw the answer. So for B for be Well, start from this. Um, we need to add to hydroxy groups. So we'll do, uh, Diaz me, um tetroxide die hydroxy elation. Mmm. So 00 S 04 followed by in a h s 03 and water. Are those conditions okay, Um, TVs protect those two alcohols that we just installed. Okay, um, now we can again use the copper lithium chemistry from this chapter, just like in part A. And of course, um, this shouldn't be bro mean there. We go to these on a copper lithium center um, And now we just need to add the rest of the molecule here. And so the rest of this molecule looks like this. And so, um, that gets us to hear Ah. And so the last thing that we need to do is take those TBS groups off. Um, and so you can do that with T V f, which is Tetra Beautiful. Ammonium fluoride. You will commonly see it abbreviated tea bath. And so that will regenerate our hydroxy groups. Okay, so there we go. There's our final product for B. Um, see is thankfully a very short problem. So see, will start from this terminally ill kind. Um, we use canticle boring. Okay, um and so the product of that I was gonna look like this. Okay. And now we can do our carbon carbon bond forming a reaction. Okay, s So that's part. See, R D is going to also be pretty short. So again, I will start from bro mo benzine like we did in part a Ah. And this time we will use a Friedel crafts reaction toe. Add what we need, um, on and then from here, we can do Ah, heck coupling on ta Here, remember, is try Ethel me. That's another common abbreviation that you'll see. Um, okay. And so that's gonna get us to our final product for D, which looks like this. Okay. Okay. Um e and F are also pretty straightforward. So for E. Again, we'll start from bro Mo benzene. And this time, we'll actually just start with the couple in a reaction. Terrible looking six member drink. Try again. Okay. Uh, and then the last thing that we need to do here is the car bean type reaction that we learned. Ah, in this chapter. And so it's gonna be with this zinc copper species, okay? And so that forms, um, Psychlo Propane brain. Okay, Um, and we actually can include some sterile chemistry here, so that would look like this. Ah, and we get both in and humor. So we should say, Plus, in Antium er so we'll get a race ethnic mixture there. Okay. And lastly, part f um, so for part f again, we're gonna take advantage of the lithium copper chemistry that we learned in this chapter. So again, treatment with lithium and then copper I died gets us to hear on then we can do Ah, coupling reaction with an alcohol. He lied. Ah, and in this case of the alcohol hayride that we want is just gonna be bro mo cyclone vaccine. Okay? And so, um, gets us thio here. And the last thing that we need to do is install on a pox side where that out Keane is, um and so M c p B a is the re agent that we know that can do that. So there's our pock side. Um, and we would get to an anti murders here. Okay, so I do apologize for this being such a long video of these or six. A somewhat complex Synthe sees a so here in pitch for Z and F, Page three c and D on be here on page two and a on page one. And that's the answer to Chapter 26. Problem number 49

This is the answer to Chapter 11. Problem number 59 fromthe Smith Organic chemistry textbook. And this problem says, devise a synthesis of the key tone three hex unknown from ethyl bromide as three only organic starting material s. So all the carbons in three hacks unknown have to come from ethyl bromide on. We can use any other re agents that we need. Okay, Uh, and so to start, I'm gonna taken ethyl bromide. Um, and I am going to do an elimination reaction with potassium turkey talks ard, and that is gonna get me to the AL Keen here. Okay, then. So from that Al Keen, uh, we can know ruminate So elemental, bro. Mean, that's going to give us the dye bromide. Okay, um and so now we have the dye bromide. We can treat that with two equivalents of sodium a mine, and that is gonna get us to the al kind. Um, and now that we are to the AL kind now we can start forming new carbon carbon bonds so we can t protein ate this out kind with strong base. So sodium high, Dr. Um and that will get us this satellite eye on. Ah, And if we, uh, used the satellite, I on with effort bromide, Since this is where all the carbons have to come from, Ah will get a displacement on dso we end up with that. Okay. Ah, And so we now have a four carbon chain. Um, and we can just just repeat what we just did. So, sodium hydride again eyes gonna de protein eight Uh, the al kind like this now and so again, another equivalent of ethyl bromide is going to give us our six carbon chain, which is exactly what we need. So six carbon chain. So all of our carbons Aaron Place. Ah, And now, um, since we're trying to make, uh, three hex unknown, um, and our al kind is between carbons three and four. Um, and this molecule, it's metric, so we don't really need any further control than that. And so we can ah, just use water. So fear Gassid and mercury, so feet. Ah, and that is gonna get us to our key tone. 123 56 Key tone on carbon three. Okay. And so that's it. Um, yeah. And so since since we were limited Thio, starting only from ethyl bromide. We just had to get from ethyl bromide to ah, settling. And then from settling, we could d protein ate that to make the satellite eye on Ah, and then use that with two equivalents of ethyl bromide sequentially to build our six carbon chain on. Then just install Archy Tone, and that's the answer to.

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.

How could achieve the falling transformation starting from second fix that thing and our lady living reporter, what would the program trust, or rather, do schools Election van if ill will end in the end, the federation, which is the most able, uh, in addition, state reading this compound is most able, uh, because of the accommodation for double bonds. Wave with double ball with other verses full by production. Will have a six my burning. Oh, okay. And to off behind groups from those problems that the opposite sides off those hurdles. Okay, the Esther, the other right, will be on the same side off. Very So we're in the same position. Reach places, Hybrid zone With this position with other conditions, so does this. That Okay, okay.


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