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Determine the mechanism (Sw2 vs Swl) and draw the product:ReactantsMechanism (Sn2 vs Sul]ProductlsHzoDMSOHODME~DME Dimethoxyethane...

Question

Determine the mechanism (Sw2 vs Swl) and draw the product:ReactantsMechanism (Sn2 vs Sul]ProductlsHzoDMSOHODME~DME Dimethoxyethane

Determine the mechanism (Sw2 vs Swl) and draw the product: Reactants Mechanism (Sn2 vs Sul] Productls Hzo DMSO HO DME ~DME Dimethoxyethane



Answers

Determine the mechanism of nucleophilic substitution of each reaction and draw the products, including stereochemistry.

This problem. We need to show how these two creating react and decide whether it's an s and one mechanism. Orin s into mechanism in the products. You have to show a specific Syrian chemistry if it exists. So the first need to safe is to identify what kind of a light it isthe. So this is a primary hey light, meaning that it's only going to react by innocent to mechanism. This is also a strong nuclear file. But since primary Alka highlight, it's going to react. Ryan s into you so it attacks in a concerted step, attacking the carbon and kicking out believing group in the same stuff. And our product is this. If this were a story of center, it would, er invert the stereo chemistry. But it's not so we don't have to worry about that party in part B. Our re agents are not in the days I and I am. So once again, you identify what kind of alcohol light it is, and this is secondary so it can do Ehsan one or s into. So then you look at the nuclear file and it's a strong nuclear file. So instead of favoring us in one at favors s and two. So once again it attacks in the conservatives. Concerted fashion, attacking in, kicking out, believing group in the same stuff and s into reactions. Invert the stereo chemistry where it was attacked. So you get this product and just make sure to pay attention to the serious industry there and seeing are free agents are ends this so once again, you identify what kind of awful Hey, light it is. This one is for Sherry, so it can only react by an s in one mechanism. The nuclear file is also weak, which favors us in one. But it's going to react right in s and one anyway because of her, she agrees he life. So the first step in and everyone reaction is federal assis. So the leaving through please by itself and then the nuclear file attacks is both front word in backward attack. But since there's no stereo stereo center here, uh, it form was one product, and the last death is a proton transfer between the substrate and another molecule of the solvent for nuclear file. In this case, that's consistent with the leveling effect because the strongest acid that can exist in solution is the person to call it So our final product for this one? Yes. This and the impregnated solve it or d. Our reaction is, and our nuclear file is water. Okay, so once again, you identify the Alfa. Highlight this awful Hey, light is also a tertiary, so it can only react fine. Us in one stuff. Nuclear file being weak also favors. And us in one reaction. So the first step, they meaning girl, please. And it produces a plane or caramel cat. I, um And in the next step, the CIA file attacks from front, side and back side. So it formed. Yeah, yes. Plus, it's the name TMR and Auntie Em are just means that the wedge in the dash were switched. And in the last step, another proton transfer occurs between the product and solve it. Hey, So our final product even my immediate about unequal mixture of both this and it's an anti armor because it was an essene. One reaction. You get receiving mixture of products

This is the answer to Chapter 12. Problem number 47 Fromthe Smith Organic chemistry Textbook in this problem asks us to draw a stepwise mechanism for the reduction of a pox side, a toe alcohol be using lithium aluminum hydride. And then we're also asked what product would be formed if lithium aluminum Ah, do Tara Reid were used as a re agent. Ah, and were asked to indicate the stereo chemistry of all stereo genic centers in the product using wedges and dashes. Okay, um and so, um, the entire point of this problem is, too, to hammer home the idea that lithium aluminum hydride does not deliver a hydrogen to the oxygen in this situation on that holds true for the reduction of key tones and Alba hides as well. So it delivers a high dried to it carbon never to an oxygen. Um and so with that in mind, here's the stepwise mechanism. It is fortunately a very short mechanism, so that's always pleasant. But so the hydride will be delivered to this carbon. Um, and now, in terms of stereo chemistry, since the pox side is on dashes and so is facing away from us the hydra. I just gonna be delivered on our side of this molecule so it's gonna end up on a wedge. Um and so you don't necessarily need to indicate the stereo chemistry there because it's not a stereo genic center anymore. Now that it has two hydrogen is on it. There's no Kat reality there. Remember, a requirement of Cairo ality is four different bonds. But waken indicated here, um, you know, just just to do it. So there's there's hydride that we just delivered. I'm in. So here on a dash is the alc oxide that now results from from that high drug delivery. So this oxygen has a negative charge. Three lone pairs. Um, it would like to make another bond. I mean, so here is where the water work up comes in. So whenever we use lithium aluminum hydride, we always tend to finish with a water work up. And this is the reason why So this oxygen one of the loan Paris Congrats. One of these hydrogen sze. And so now we've pro nated our Alcock side. Ah, and we have a neutral molecule. And indeed this is the final product that we were asked to draw the mechanism for. So here's our final product. Um, metal group put this hydrogen in here against for consistency. Um, and now we have our alcohol there. So, um, so that's part A. As I said, this is a very simple, straightforward mechanism. Um, and so if we were going to use lithium aluminum to tear eyed instead, eso part be here on the product would be exactly the same. Except where we delivered that hydride we would deliver. Um, e yes. It would be called a Dou te ride. Uh, so ah, were we delivered that hydride? We would instead have, uh, deuterium there. And so nothing else about the molecule changes. Our final product is the same. Sterile chemistries are the same, but here we now have a deuterium. And so again, the whole point here is to just hammer home the idea that lithium aluminum hydride delivers its hydride never to the oxygen, always to a carbon that is bound to the oxygen. Whether it's the reduction of a pox side like this reaction or the reduction of an alga Hideaki tone, it always works that way. And so that's the answer to Chapter 12. Problem number 47

This is the answer to Chapter 23. Problem number 59 Fromthe Smith Organic chemistry Textbook. This problem asked us to draw a stepwise mechanism showing how to alk elation. Products are formed in the following reaction. Okay. And so um, yeah, basically, what we have here is the LD A, um the dicer problem night is going to look, I like what I've drawn here. Ah, and so that is going to grab, uh, this proton. The electrons will go to this carbon. And so, um, are major intermediate here? Oops. Let's try that again. Okay, So our intermediate here, the main intermediate in this reaction is going to be this one. Ah, and so we have a lone pair and a negative charge. Ah, here now. And one thing that can happen is the direct calculation. So have our metal. I died. Uh, this loaned hair, uh, can crab the metal group. And so when that happens, we end up with one product. Okay. However, we can also get rearrangement, and so I'll draw draw the movement of those electrons in red just to distinguish them s o. The lone pair could also, uh, ad. And here um, and these electrons, I could go here like that to you that carbon. And so when that happens, um so really, this is a resident structure. So when that happens, we have this. So our double bond is now here, nor loan pair and negative charge are now here. Um and so from here, the exact same thing can happen. So these electrons can grab that metal group, and then we get alk elation on that carbon. Okay, so there we go. There's Thea stepwise mechanism that accounts for the formation of these two different products. So after the deep throat nation, we have this intermediate. That's rearrange or not on. If it doesn't rearrange, you get the top product. If it does re arrange, we get the bottom product. And that is the answer to Chapter 23. Problem number 59

This question would roaring the results when we're making some A settles. So first begins, be mixing propane al plus f inal. So Wiggins gets the heaviest Sesil. It's, uh it starts with the proof. Now we'll have seek age three c hate to. Okay, so this is almost criminal. Criminal would be okay, would be this, but we're not having that. Instead, we're going to have ah hydroxy group and we guns form our and they get on best be methanol. It's This is for me. And if we want to get the actual full of Seattle where going to be taking its hard from him and said Obey, uh, I drugs a group, this itself is going to get another national reacting. So you get this from full acetyl. That's right. On the 2nd 1 we have cyclo Penton own plus methanol. So if I said to him, that's the look. It's Cyclone Penton. So starts by drawing it. We have this to select a pencil and where guns be attacking this Keating Group, so we're going to get rid of this. Wigan's have bust a higher hydroxy group it and see him three because it's a methanol services be Hemi of Seattle. And then if we want to continue our reactions get be full of Seattle. We're going to hear from a hydroxy Teoh. Never. Here we go, another me fellow group, and this would be full Sesil.


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