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What acetylide anion and alkyl halide can be used to prepare each alkyne? Indicate all possibilities when more than one route will work.a. $left(mathrm{CH}_{3}ight)...

Question

What acetylide anion and alkyl halide can be used to prepare each alkyne? Indicate all possibilities when more than one route will work.a. $left(mathrm{CH}_{3}ight)_{2} mathrm{CH} mathrm{CH}_{2} mathrm{C} equiv mathrm{CH}$b. $mathrm{CH}_{3} mathrm{C} equiv mathrm{CCH}_{2} mathrm{CH}_{2} mathrm{CH}_{2} mathrm{CH}_{3}$c. $left(mathrm{CH}_{3}ight)_{3} mathrm{CC} equiv mathrm{CCH}_{2} mathrm{CH}_{3}$

What acetylide anion and alkyl halide can be used to prepare each alkyne? Indicate all possibilities when more than one route will work. a. $left(mathrm{CH}_{3} ight)_{2} mathrm{CH} mathrm{CH}_{2} mathrm{C} equiv mathrm{CH}$ b. $mathrm{CH}_{3} mathrm{C} equiv mathrm{CCH}_{2} mathrm{CH}_{2} mathrm{CH}_{2} mathrm{CH}_{3}$ c. $left(mathrm{CH}_{3} ight)_{3} mathrm{CC} equiv mathrm{CCH}_{2} mathrm{CH}_{3}$



Answers

What nucleophile is needed to convert (CH3hCHCH2CH2-Br to each product?
a. $(CH_3)_2CHCH_2CH_2 - SH$
b. $(CH_3)_2CHCH_2CH_2 - OCH_2CH_3$
c. $(CH3)_2CHCH_2CH_2 - OCOCH_3$
d. $(CH_3)_2CHCH_2CH_2 - C = CH$

This is the answer to Chapter 11. Problem number 17 Fromthe Smith Organic chemistry textbook. Ah, and this problem asks us what a satellite ion and alcohol he allied can be used to prepare each al kind. Ah, and we're told to indicate all possibilities when more than one route will work. Ah, and so, looking at a we have a terminal Al Qaeda here. Ah, and so there's really only one way that we can prepare this. Um, and to think about this, uh, we didn't think about cutting between, uh, the carbon that's participating in the triple bond and next carbon. And so, uh, this could look like this or this could be formed from this, I guess, is what I'm trying to say. So ch ch two aunts are alcohol Hale. I was gonna be here, so let's put a quarry in there. Um and then Ah, our satellite ion. So with negative charge there. Ah, and that's really the only the only possibility here, um, to form this eso um, looking at B b is an internal al kind. And so we can actually cut at either of two locations so we could cut there or we could cut there. And so this is going to give us two possibilities. Um, And so if we were to make the cut, um, on the left red squiggle that I drew, uh, our components would look like this. So methyl chloride would be our alcohol allied. Ah, and then are a satellite eye on would basically be the rest of the molecule ch two see age too ch to see h three. Uh, or we have the other possibility If we were to cut, um, on the right red squiggle that I drew, um, now, our satellite ion is going to be this one. So there's our satellite eye on ah, and then the rest of our molecule is going to be the alcohol highlights. So let's put a chlorine there on then. Ch two ch two ch two See? Age three. Okay. Um, and so looking at sea, she is almost a little bit of ah, trick question here. Um, so see, you look at it. And you think, um, okay, so we can do exactly what we did in B We can cut here, which is true, or we can cut here. Um, and that's actually not going to work. Ah, and the reason that the green squiggle doesn't work, um is because, uh, this would then be, um a tertiary alcohol. Hey, lied So tertiary. Alfio. Hey, Lied would eliminate. So if we were to try this reaction, what we would actually get would be an elimination reaction instead, Um, and we would not get our desired product. However, we can do to reaction the other way. Which is to say, we could cut along the red squiggle, and so that would give us this. Ah, satellite ion. So there's our satellite eye on um and then the rest of our molecule would be our alcohol. Hell, I'd so ch to see h three. So that works again. Three green squiggle that I drew here would not work because that tertiary al Kyohei light is too crowded to do this s and two reaction on DSO. Instead, we would get elimination. So for see, there's only one possibility, even though it's an internal out kind. And then a and B sort of followed the patterns that we would expect where a terminally ill kind is gonna have one possibility and the internal out kind will have to. Ah, and that's the answer to Chapter 11. Problem number 17

This is the answer to Chapter 11. Problem number 55 fromthe Smith Organic chemistry textbook. Ah, and this problem says what a satellite eye on are important me. What a satellite and I on and alcohol. Hail. I'd are needed to synthesize each Al Qaeda. Um, okay. And so we're working backwards. Ah, and basically, we need to think about where we could cut each of these molecules, uh, into unsettle. I'd eye on, uh, and the rest of the molecule on and then make the rest of the molecule in alcohol. Hey, Light. And so, for a that's gonna be pretty obvious since this is Ah, terminal terminal Al kind s o. The cut's gonna be right through that bond right there. Um, and I'll do the answers and green, um and so this is gonna be our satellite and I on and our alcohol hail ID will be the rest of the molecule. Uh, and so, uh, let's make it a bromide. Why not? Okay, so this is the answer to a, uh and that's exactly what we'll do for the other two. So then, for B, are we at first glance, have two options here is to where we could cut the molecule. But if we were to cut to the right of the al kind, we would then be using a tertiary alcohol. Hey, lied. Ah, And as we should know from this chapter, tertiary alcohol here, lives were gonna be too hysterically hindered to undergo these reactions on. So we'll cut to the left of the AL kind. Um, and, mate, uh, the alcohol. I hear what's use chlorine. Eso will make the methyl chloride. Ah, and then our satellite and I on will be the rest of this molecule. Yeah, okay on. So that's b and then for C uh, again, Same thing. Um, putting the alcohol alight on the ring again would be too hysterically hindered. So we'll cut to the right of this al kind. And so our a satellite eye on an eye on Will I have the ring on it? So there's that, and then the rest of our molecule will be the alcohol. Hey, light and let's use Ah, right on. Why not? So, um, Pro Bowl iodide. Okay. Uh, and so that's Ah, that's all of them. Um, and again to do this, we just need to sort of work backwards. Think about where we could cut these out kinds, um, and then keep in mind, like, for be that a tertiary out. They'll halo. It's not going to work then, so we'll have to. I select the bond to break. That's going to give us a methyl chloride instead of, um, a church sherry, I'll go hell like, and that's the answer to Chapter 11 problem number 55.

We won today. We're doing Chapter eleven point fifty eight. And this Palm asks us to use this. Cyril, I'm certain material or Ethel oxide on any uncle. Hey, light switches. Hydrocarbon axel. Use too arbitrary ch something x a certain materials for the generation of these four products. So let's start with a so a we have your i'LL kind born, But then we add one, two, three, four, five, six more carbons. One, two, three, four, five, six carbons. So how we do that? Well, you know, we can make the city line from priest forms such as fifty six. We make a serial line into a new profile by deep resonating it. And we add this alcohol, he allied with the appropriate number of carbon. So we already have these two carbons here from our starting material with these two carbons Here, Mr Material so need one, two, three, four, five stripy six, one, two, three, four, five, six carbons. One, two, three, four, five, six, one, two, three, four, five, six. So we know if you serve a serial line and deep urinating using sodium hydride, you won't get your one side of it. We d prone ated. Two former carbon I own one shouldn't if you were reacted with an electoral fluke. Alcohol allied with appropriate number of carbons Ever China was one too. Three four five six with highlight being broening or chlorine. You wouldn't get a nickel for look Attack to get a crown product being one, two, three, four, five, six Harm's institution which is product, eh? It has to be so be were doing the same thing as they were adding one, two, three, four, five, six carbons to one side. But in addition from this step now we're adding two more car bombs on the other side. So it's very similar to Pawn fifty six, actually what we just did so Mrs S O. B. So if I add carbons from one side first doesn't actually matter from which side you added on It is not to be the longest shortest sides Any side Azzam Sequential order you sequentially, Adam on. So let's just was sick of this problem was first ad this excited one because we already know how you do that. So one, two, three, four, five, six with a hey light and actually disarm his chlorine just emphasizing any Allied. One, two, three, four, five, six. But now, from this step, when it deep protein ate the other side of the cedar lined me Take away this proton to make carbon in on this location and then we can add are now two carbon source electro falls one too with any he lied and will use Ida in this case. So one, two, three, one, two, three, four, five, six, one, two. And this is your product. Hey, so now see from certain from cease to see what we have So we have actually one, two, three, four, five, six. Once again you're adding the same six carbon into one side of this out time for there are one two and alcohol. So it seems so if you see that we're adding to and alcohol But we can use any Uncle Halo. So some may see that once we get this product here weaken deep only the other side of this all kind And then we can add two carbons that we need on one side will be Hey, lied and other side will be in alcohol. And then you just get your two harms and alcohol product because you're here. I could get kicked off while we have a restriction for certain materials can only be in alcohol like this. Not outcome here like we have alcohol here. So let's see what other certain materials we can use. Well, we have two carbons in this ethylene oxide every of oxygen. So this also provides a number right number, Oxygen's and on carbons on DH, This actor's electro Felix These two carbons actors electro for the carbons because of the lecture on pulling density of oxygen. So it's pulling electron density away from these carbons making these election portal trumps electoral Filic susceptible, susceptible to nuclear flick attack from you're a serial line or from your al kind of carbon ion nickle fell. So for C, let's do thing things over. See, we're taking your line and we're adding six carbons to it for to make that one side. One, two, three, four, five, six CEO one, two, three, four, five, six But now we're gonna add so then high drive to make a carbon eye on. But in our electoral fall, this time is going to be this, uh, this, uh, ethylene oxide in the whole form. So your carbon on after this depot Nate's it carbon now And that can attack either side making bond you make upon your break about this pops open. So then you'LL be left with an old minus. But we need o h honey. New client neutralized old minus one. The past we used sand, water as well. So if you add water than you haven't alcohol at the very end and no charges left So you have your one two carbon and in your old age So this is for sea and then for D what do you have so for D? We are having one, two, three, four, five, six carbons just like in all other examples. And then we have into carbon oxygen just I can see. But then from the oxygen stepper adding two extra carbons. So now oxygen these actors nuclear fall So if I deponent is optional with all minus which would be a charged electoral a lot from rich nuclear fall which can add since attack some sort of alcohol a light. So for D let me write this in red. So for D, we actually need to redo all the steps of sea to get to this point because we had our six carbon, sir, a serial line. There were deep urinated and at the ethylene oxide to get this alcohol's never at this stuff. And I need to Deep Throat Nate this alcohol with any dip rotating agent X sodium hydride or in a minute and his two minus. And then we'LL get oh minus New glow fall and we need to attack and Elektra Fall So we needed to carbon electrode files one to carbon And we need a leaving group So could be any highlights of what to say bro Mean And then we'LL get in essence to nickel Filic attack with this Oh, and others two carbons Then we get our product d from sea.

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.


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