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If anisole is allowed to sit in $mathrm{D}_{2} mathrm{O}$ that contains a small amount of $mathrm{D}_{2} mathrm{SO}_{4}$, what products will be formed?...

Question

If anisole is allowed to sit in $mathrm{D}_{2} mathrm{O}$ that contains a small amount of $mathrm{D}_{2} mathrm{SO}_{4}$, what products will be formed?

If anisole is allowed to sit in $mathrm{D}_{2} mathrm{O}$ that contains a small amount of $mathrm{D}_{2} mathrm{SO}_{4}$, what products will be formed?



Answers

What product is formed when each compound is treated with either LiAIH$_4$ (followed by H$_2$O), or
NaBH$_4$ in CH$_3$OH?

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

A stereo. Isom er are two or more compounds differing Onley in the spatial arrangement of the atoms. Therefore, they do not differ in where the method group might be or how long the parent compound is. But they differ in the different orientations based on a double bond or such as an al cane or a Cairo center, and how those bonds are arranged around the Cairo carbon. So our example that we're looking at is form Ethel to Hexi. There are four stereo. I simmers for this problem, and I have these four stereo I summers written out below. And so, as you can see, there's not much different. But as we go through, you'll see there is a little bit. So these 1st 2 the Al cane are the same. They're both trans. So if we're going to type out the name of for Merkel to hex ing read, put intrinsic parentheses. E, which indicates that the two already one since its situ INTs coming off of the out canes are on opposite sides. And so I'll go ahead and write for knuckle to tech scene and then another about the difference between these two trains molecules is the Carl Center. So as you can see, this 1st 1 goes in A s direction while the 2nd 1 goes in our direction. And how we know God is for we first assigned priority. So the hydrogen will always be priority for, and then you go based off. This one will be priority one, because it has the more carbons, and then this one will be priority to, and then this will be Priority three. And so what you want to do is get your priority one where it's staring out to our the page and that's usually represented by a wedge. And then going into the plane is represented by a dotted, wedged or alluring wedge. And so you want to manipulate it to where the front priority one to staring right at you and then you count it. And if it's going clockwise, then it's our and then if it's going counterclockwise, it's us. And so it might take a little bit practice. But as you can see, this one is us. And so B E. Because and then if we're going to the same thing with the 2nd 1 would be the same, except instead of s you would haven't are because when you label your priorities and then countem up, you'll realize that when you go 123 we'll be going in this direction. We'll be going in this direction. So be our. The same thing goes on with the next to but they the alcanzar in assist position. And so our third example is in a cyst. So it would be characterized us Z because the party one compound are on the same side and then the 1st 1 If you label your priorities are on the Cairo Center, you'll find that it is in S. And then it will also be for, after all, to heck sing. And then, if you do the same thing with Chris Carlson er on the 4th 1 you'll find that it is going in the our direction or going clockwise. And so it will be easy are Or and then those are your stereo. I summers

Going to look at Alba hides and key tones. So this functional group where we have our carbon carbon that is connected to other carbon atoms or even hydrogen atoms on either side, it offers quite interesting functionality. And we'll take a look at an example here. So when lithium aluminum hydride is treated with our starting material A, we have the following reactivity occur. So this is our starting material C two h five. So let's see, um, aluminum hydride hateful. What we then generate is alcohol groups. Where are original carbon aisles were so now called group from here and then we see an alcohol group Care C H 20 h.

Right. So talking about periodic acid and, uh, it's decomposition. First, we're going to start with this molecule, which it doesn't give you the structure of, but it gives you the name off, so let's be more than enough, and that will kind of be broken down. You have this bond being cleaved right there on that won't be broken down to two equivalents of this very basic he time. But that only takes one equivalent of, um, h i 04 That's moving on to be. Now we have a pretty similar structure this time. 123 a beauty in trial. All right, so this time we got some slightly different things going on. First off work, leaving not only this bond, but also this bond. So now we're gonna be using to e que of age i 04 Yeah, and that's going to produce. The products were going to equivalents of formaldehyde, plus one single equivalent of, uh, she needed of this most basic Itoen. And like I said, that's gonna take two equivalence moving on to see that's actually gonna have no reaction on you can tell because there's an extra CH between every of the older age groups. Ah, so there's no way the periodic acid could really interact with those. So moving on to D Ah, we now have this structure notice we have a No. A tree next to that Alfa Carbon s. So we have this bond in the middle being broken right there. Uh, now, this bond right here is not Birkin because there's too much of a carbon gap between this guy and that guy. So we don't to worry about any sort of cleavage from there. So what we're gonna get using just one equivalents of H I go for is we're going to gets first off this product that comes from the cleavage of home bond. And on the other side, you just going to gets that compound eso on moving on to party. We have a symmetric molecule here. So quick, moronic acid. You know, we're gonna be breaking to Bonds, right? We're breaking that one, and we're breaking that one. All right, So what we're going to be doing is adding to equivalence of pure out of Cassidy and what that's going to do this is going to produce, um, two equivalents off that as well as some formic acid in the form of ah, the most basic complexes. Like acid just like that. All right, um, so coming up here, I have to squeeze a little bit, but f we're going tohave this key toe or this Ah, contain here on the first and second carbon are gonna be alcohol's. All right, So using Just were only cleaving this one bond re there. Luckily, um, so using that one equivalents, we're gonna end up with a structure. Um, that's going to look like this. No, let me draw another bond off of there. Um, let me read you all that. I think I drew a little too far up. It's not like I mean, draw the entire molecule. Um, all right, there we go. That's a little better. And like I said, this is one equivalent of periodic acid. G again is gonna be no reaction on you can tell just because of the spacing there. Lastly age with Dee Rees Gross. You're gonna have this hygiene here, uh, from the outer hide with my reaction here. Ah, this time work. Leaving quite a few bonds specifically to bonds that we're gonna be Cleveland on this one and that one. Some. When we do that, we're gonna end up with, um, formaldehyde again. We're gonna end up with ah, formic acid, and we're gonna end up with a slightly more complex crab oxalic acid. Oh, uh, and lastly, this is going to be two equivalence of periodic acid simply because to bonds of being broken.


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