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Design a synthesis for the molecule. The starting material canbe bromobenzene, cyclopentane, cyclobutane, or any molecule withthree carbons or less....

Question

Design a synthesis for the molecule. The starting material canbe bromobenzene, cyclopentane, cyclobutane, or any molecule withthree carbons or less.

Design a synthesis for the molecule. The starting material can be bromobenzene, cyclopentane, cyclobutane, or any molecule with three carbons or less.



Answers

Design a synthesis of each compound from alcohols having four carbons or fewer as the only organic starting materials. You may use any other inorganic reagents you choose.

This is the answer to Chapter 21. Problem number 65 fromthe Smith Organic chemistry Textbook. This problem says devise a synthesis of each compound from five hydroxy to Penton, known as the starting material on. We can also use alcohol is having three or fewer carbons and any required organic or inorganic free agents. Okay, s O starting from five hydroxy to pent known which have drawn here, um, to get to the product that we have here, Um, we need to add some carbons to this molecule. Ah, And basically, in order to do that, we're gonna use a graveyard re agent strategy. But before we do any of that, the very first thing that we need to do is protect our key tone So that Archy tone doesn't react during all these other steps. Um, and so that we can actually use a greater because remember, if we try toe, make a Grenier and we have a key tone present in the molecule that we're trying to make into a grin. You heard It's not gonna work. It's gonna quench itself, react with itself s o. We use ah, cyclic acid towel protecting strategy. So ethylene glycol and some acid eyes going to take us from our key tone to the cyclic ASA town. So this is now protected. Um, and we can pursue the strategy that we need for the rest of molecules. So the first thing is gonna be to use PVR three and convert this to the bromine. Um, And now now we can make the greener. And so actually, we're going to need I see you Samassa tone, um, as our carbon Neil to react with the graveyard. And we can make acid tone, um, from ice a proven all because remember, three carbon or fewer alcohols eso weaken just oxidizer mice appropriate home. And that is going to get us to ask toe. Okay, so we have a green your dory agent. Ah, and we will go ahead and react that with acid tune. Ah, and then work it up with water, as we always do with Grenier. Three agents. Ah, and so that is going to get us to hear no more. Okay, so we've added the carbons that we need. Um, and now, uh, we need to de protect our key tone. And so that is accomplished by acid tell hydraulics, sis. So little bit of acid and some water, uh, gets us back to the key tone. And so to get to our final product, we need to have an alcohol there. And so we can accomplish that. Uh, with any anyone reducing agent so you could do sodium for hydride. Uh, I'm going to do lithium aluminum hydride in that gets us to our final product for part A. Okay, so for part B, we're actually gonna start from an intermediate that we made in part A. So we will start from the protected bromide. Okay, so we have the protected bromide here. Um, and we are going to make this into a vinegary agent. And so remember, in order to do that, we need try fennel, phosgene. Ah, and then beautiful lithium to de protein. Eight. Uh, and so when we do that, we end up with this vinegary agent still protected Here. Um, and now Ah, we need, um a three carbon alba hide. Um, And so we will again, uh, make that by oxidizing the alcohol. Justus, We did in part a So one probe in all this time instead of two propane, all oxidized with P C c We get the alga hide that we need and so we can use that Alba hide with our vid agree agent And that is gonna get us Thio here. Oops. Move down a little bit so that, uh, we can see what's going on here. Okay, so we have our double bond here. Um, there we go. Uh, and this, of course, would be a mixture of e and Z. I summers, um, okay, but I've just drawn in his e, but that's fine. Um, and now, in order to get to our final product, we just need to de protect. And so h 30 plus or H plus in each to oh, same thing. Okay, so now we have our key tone. Uh, and we have our double bond here. Um, okay. And the problem tells us that this final product is going to be in Ian's. You make sure. And so using this rather have outlined here, this would be an e ends mixture. That's fine, because that's what the problem calls for. Okay, um and so this is another synthesis problem similar to an earlier one. Just highlighting the fact that we can do similar things using using a strategy of Green. You agree, Agent Oh, are using this strategy of a vinegary agent. So it's just different ways to make new carbon carbon bonds us apart. A we're gonna do with the graveyard strategy, Part B. We're going to do with a video strategy. Ah, and that is the answer to Chapter 21. Problem number 65.

This is the answer to Chapter 21. Problem number 64 from the Smith Organic Chemistry Textbook. And in this problem, we're asked to synthesize two molecules from given starting materials. Um, and basically, we're told we can, uh we can also use alcohol's with four carbons or less. But then we can also use any organic or inorganic re agents that we want, which I get, I guess would encompass all alcohol's regardless of Carbon county. Um, but okay, so anyway, so for a, um we're told to start from benzene. Um, and so Ah, benzene. Okay, um and so, um, basically, we're we're going to need thio put a handle on the benzene. Um, but also looking at the final product. Um, I see that there is a double bond in it. There's an AL keen on. And so, uh, my thinking is given the other problems in this chapter, let's construct that Al keen using a Vidic reaction. Um, of course, there are probably many different ways that you could make this molecule, but I think given the other problems in this chapter, that's probably what they're looking for. So we'll do it with Vidic. So In order to do that, we're going to make to this molecule in two parts and then join them with the video reaction. So we'll need to make a vinegary agent part. And we need to make a, um, Karmiel part. Ah. And so we can, Actually, since since his molecule it's symmetrical, we can actually make them from a common route for the first few steps. So the first thing we're gonna do, uh, would be to do a Friedel craft here in order to put a handle on this benzene. So we do a Friedel crafts with methyl chloride. That's ugly. That's gonna add a metal group. I mean, So now that we have that method group, um, we can oxidize it with K. M n o form came and a four I's gonna convert that method group into a carb oxalic acid. Um, and then if we treat that car box so Gassid with lithium aluminum hydride are we can get to the alcohol, and then we can oxidize that alcohol, uh, two. Um uh, now, the height. Um, sorry s o. I will do l A h year. Um, and then water work up. Uh, so that's going to reduce our car box. So weak acid that we made to the alcohol. Um, and then if we treat that alcohol with pyrenean chlor, chromite, pcc, we will get Yeah. Hi. And so that's one of our pieces. Um, as I said, we're gonna gonna make two pieces and connect them via video. Ge. And so remember, we need to make a video re agent, and we need to make ah, kee toner. Now the hide and we've made another heart. There s oh, now we can begin to look at making the second piece. Um, the Vidic piece. And so, in order to make the video piece, we're going to start from 123 from our third intermediate that we made above. So we'll actually start from that primary alcohol that we made. So there's our primary alcohol. So again we would start with benzene, do our freedom crafts, do our potassium permanganate oxidation on, then the lithium aluminum hydride reduction to get to this This, um, starting molecule for the second part here. Um and so we'll take that alcohol. This should be a familiar sequence by now from this chapter, so we'll treat this alcohol with pvr three to make the bromide in place of the alcohol. Ah, and the utility of that, of course, is we can then react the bromide with trifle phosgene and then beautiful lithium. And that's gonna get us to our video. Agree, Agent. So there's our bromide. You will do pH three p, followed by Buell E. And that is going to you get us to our video. Okay? And so now all that we have to do is combined vinegary agent that we just made with the Alba hide that we need right above it. Uh, and that's gonna give us our final product. PPH three plus al behind gives us final product. Um, and so that we would get we would get e and Z I summers here. Um, but the problem doesn't stipulate one way or another whether it matters if we get both or if they only want one. So this is fine. I mean, so that's the answer to port, eh? So then looking at part B, um, let's see. So what's Ah Oh, my, What a retold to make for part B. Um, okay. S 04 part B. We are told Oh to make a very similar molecule from benzene and fennel. Um, okay. Ah. And so, um, I will draw this again, draw our target out so that we can see what we're trying to make this. Yeah. Okay, um and so this is extremely similar to the molecule in part a. Again, there's an AL keen right there. Um and so probably the way to make this one is gonna be to follow the exact same, um, reasoning that we followed for party. So it will make a bid, agree, agent, out of 1/2 and we'll make, um, on alba hideout the other half. And then we'll do a video reaction to construct this molecule. Um, and so what that's going to look like, uh is, uh, Let's see. Okay, Um okay. So let's make the right side first. Eso will make our video first. Okay. So, uh, we're going to start from Finn. All here, remember? We were told we can start from fennel and benzene for this problem. Um, start from phenom. We will start with a freedom craft again. Now we've put a metal group on our starting for Nam. Um, we I can then make ah v meth oxide so we could use a strong base like sodium hydride. Um, and then some methanol ch 30 h are actually No, I apologize. Okay, so we would want to use ch three b r. So method bromide, Um, after treatment with a strong base S O that is going to get us where we want to be. Um, So we now have in the stocks side here. Okay, Um and so ah, we can then do a Ben's Ilic Brahma nation. So we'll use bro mean and light. Um, again, that because this is a narrow matic system who that's going to give us a bro mean at the Benz Ilic position here. So, uh, benzoyl extermination. Uh, and then, um from there, huh? We can make our vinegary agent. So remember, it's gonna be alcohol allied plus trifle, phosgene, and then beautiful lithium. So lithium on that will get us to here. Okay. And so obviously, this is going to be on the left side of our molecule. Okay, so there we go. So there is a riveting, um, and again, that's that's the left side of this molecule. So to construct the right side. Um, we will, uh, start from benzene. Uh, we'll do a free crafts onto benzene, uh, using this t beautiful chloride rather than methyl chloride. Um, okay. And so rather than adding a method group, obviously that's going to add a t. Beautiful. Okay, So once the T Beetle group is installed, um, we'll do another Friedel crafts this time with methyl chloride on. That's going thio obviously install a metal group pera to the TV to group. Um, and the point of doing that is that we can then, um, oxidized that with potassium permanganate. Oops. Okay, so, um, this is similar to the strategy that we followed to construct, um, half of molecule in part. Es eso t view group there. Uh, that's potassium permanganate is going to give us, um, oxidation to the carb oxalic acid here, a two benzoate position. Um, and then, um and I don't want to put this all on 1/3 page. So what I'm going to do is, um, sort of combined steps here. So lithium aluminum hydride and then a water work up eyes going to get us to the primary alcohol, um, and then treatment with PCC is going to get us to the Al Jihad. So after this, after the sequence pictured there, what we have is this album hide. Um and so obviously this is ready to react with the, um, the degree agent that we made right above it. And so the product of that reaction eyes going to be our desired product. Our final product here, Um, and again we would get e n z. I simmers. But again, the problem doesn't specify whether it wants one or the other or both s O. So that's fine. Um, yeah. And so that's the answer to be, Um, And again, the strategy here is just thio Identify that that you can cut this molecule these molecules into, um at the double bond. Um, and then identify that you could use a video to join the two pieces together on. Then go ahead and just make the two things that you need to your Vidic, the vinegary agent itself and, uh, carbon me over. Um And so that's the answer to Chapter 21. Problem number 64

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

Okay. This problem is asking us to synthesize this molecule, starting with a compound with no more than three carbons. Okay, so before even and consider what three carbonate, what's not? I'm going to consider what is attached to this album. So we have mild high, and then we have a nitrogen attached to the beta carbon of this album. So getting here's my, um out of number zero here is Alfa and here is Beta. So I see that I have a nitrogen attached to the beta carbon of this album Hide. And that's important because we can actually advance to beta carbons. Okay, so let's go ahead and consider this. If I have a three member compound, start off with, let's go ahead and make it my Alba hide something, have my album head to start off with. So let's just say I have and held ahead here. Remember, it's three carbons totals. I'm gonna have one, 23 carbons total. That's 123 So, considering that, let's go ahead and make it into this six carbon compound. So I have 123456 I need to add six more carbons, and luckily we just learned about, um, held auditions, which is basically distracting this compound with another molecule itself in basic conditions. So using sodium hydroxide, which is a strong base, I'm going to take off the Alfa hydrogen. Okay? And that's because it's the most acidic. And my base take off the alfa hydrogen, it moving the electrons onto this carbon. Could someone have? This is my intermediate in which I have this set of lone pairs on this carbon. Okay, so again, this is going to undergo erection with itself. So if I have another molecule of this album hide, I can go ahead and take these electrons and attack this carbon. That carbon is considered to be Electra Filic. This carbon is considered to be nuclear foot. When I attack that carbon, I'm gonna have to move the elections up to this oxygen that will result in the formation of this product in which I have my childhood and then connect to the Alfa Carbon. So this Alva carbon correspondents to this karma right there connected to this carbon. We have a connection to this carbon which is describing over here and connect that carbon we have in my auction with a negative charge. We have my hydrogen so that hydrogen corresponds to that one. And then connected to the carbon is what we have. My Essel group. So 12 carbons. Okay, so that's that. And then we have to undergo my algal edition portion of, um, action in which we basically have two protein ate this alcohol or the metal minus. Getting there is going to do that with water. And we formed water from the tote nation of my sodium hydroxide. So it'll form. This is my problem in which I have my molecule a bet. And then Captain Tat, Mr B, and I'll ride, for example. Okay, they don't have my auction with my proton, and then I'll have my two carbons over there. Okay, so that's where I'm at right now and again. I need to get Teoh right here. I need to eventually add this amine group to that beta carbon of my whole compound. So how do we do that? Well, in order to add a substantial into onto the beta carbon of a compound such as ah Carbonell compound, I need to get that beta carbon to be Electra Filic and to get that bit of carbon electrical? Look, I need to make it into an AL Keen, so I'm going to perform an Aldo Conversation direction in which I essentially get rid of this alcohol. And in the process of getting rid of that, I'm going to make an arcane right there. Okay, so I'm going to do that using a base again. So based is going to go ahead. And deep protein ate the Alva hydrogen. Okay, this is the Alfa 100 right there. And I take those electrons between the carbon and hydrogen and move them onto this single bond to make a double bond making a pain. And when I do that, I'm gonna have to move the electrons onto this alcohol to make it into a leaving group. So I should, For this is my product in which I have my head over here, my two other carbons and connected to the beta carbon start that awful carbon. I have the connection to my booking, and I have the two other carbon over here. Okay, so that is my molecule right now. So again, I still need to make this NH two group attached to that beta carbon. So getting debate a carbon right now is Here's Alfa. Here is beta. That's my beta carbon. That's my alpha beta and saturated Alba had in order to add something to that better carbon. All I need to do is use a nuclear file because I need to add on and they but the image to To that you manage to I'm going to use NH three that's gonna behave as my nuclear file and going to attack that beta carbon, that bit of carbons. Electra Filic, attack that beta carbon. I'm gonna have to move the electrons all the way up to this. Carbondale. Yes. That's going to form this intermediate in which you have my auction with a negative charge. My hydrogen over there. My okay in there and then my connection to my end H three deposit charge on the neck region just like this. Okay, so now we have to just basically fix this molecule. Want to get rid of this negative charge in the auction and to to get rid of this posit charge on that nitrogen? Okay, so that's going to undergo basically just a couple more reactions, but it's eventually going to end up as my academic product, which is as follows and it's to there. And then finally, finally my effort group over here. Okay, so if we compare this molecule to my starting material or what we wanted to get to, it's going to be the same thing. So that is the synthesis of that molecule.


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