5

Draw a stepwise mechanism for the conversion of $eta$ -D-glucose to both anomers of $N$ -ethyl glucopyranoside, the reaction shown in Reaction [1]....

Question

Draw a stepwise mechanism for the conversion of $eta$ -D-glucose to both anomers of $N$ -ethyl glucopyranoside, the reaction shown in Reaction [1].

Draw a stepwise mechanism for the conversion of $eta$ -D-glucose to both anomers of $N$ -ethyl glucopyranoside, the reaction shown in Reaction [1].



Answers

Draw a stepwise mechanism for the conversion of trans-2-butene to the meso dibromide in
Figure 10.13.

This is the answer to Chapter 27. Problem number 57 from the Smith Organic Chemistry textbook. This problem asks for a stepwise mechanism for the carol rearrangement which we're told prepares a gamma Delta unsaturated karp Neal from a bay taquito, Esther and analytic alcohol in the presence of a base. Okay, now and so the first step here is gonna be deep pro nation of this electric alcohol by the base. Uh, so that's gonna look just like this. Okay, um, the next thing that will happen eyes going to be, um, attack of that nuclear file that we just formed on the beta Kato. Esther. Okay, um, so that will look like this. All right, um, and the intermediate that we form, that will be this one. Okay, s So we have this Tetra Hydro Intermediate. Um, And as we know from previous chapters, this will close back down. Ah, and kick out. Are this sock side? Ah, and so we're producing this product that I'm drawing here. Ah. And also, we would make a sock side which would then be pro donated by water. Ah, that's in this reaction on. And that's where the ethanol product would come from. I'm not going to draw that. I'm just gonna focus on the main organic product that we're making here. Ah, and so this intermediate I can now be be pro donated at this Alfa Carbon Alfa position. Eso another equivalent of base can come and grab this hydrogen. Ah, and form this. Uh, really? And so I'm gonna change the orientation, Uh, here, like this so that it's much easier to see. Ah, the Paris cyclic reaction that's gonna happen here. Okay, um and that Paris cyclic reaction is going to look like this. And so, uh, we've now made a six member ring. Good. Okay, um and so Oh, no. Right. OK, so this bond, uh, so we haven't made a six member during this Bond is broken. Sorry. I'm having having trouble reading my own writing. Okay, so No six member during here, Um, in fact, let me, uh, even in just this, more so that it's not confusing. There we go. Uh, Okay. Um okay. And so the next step now I's gonna be pro nation of this oxygen and so water do that. Okay, um, and now from here, um, we're going Thio have another Paris cyclic reaction Occur, Uh, and so that is going to look like this. Um, And so actually, uh, gonna change this orientation is well, so put the hydrogen here on this will look a little cleaner. There we go. Okay. S o that parasite click reaction takes place. Um, and we're gonna lose Seo to in this step. But again, I'm not gonna draw that, because really, I just want to focus on the main organic products here. Okay, Um and so the last thing that's gonna happen here, it's gonna be re formation of this Carbonell. And so base can come and t protein eight. Uh, this oxygen. Okay, um, electrons will move like this, like this. And so we're gonna have a lone pair in a negative charge on this carbon. Um, you know, I'm actually going to move this up, Um, just s so that I can fit everything on a single page here. Um, and so just the very last thing that's gonna happen is gonna be pro nation here. So again, water, uh, can protein eight. Ah, this loan pair and that is gonna get us to our final product. Okay, Um, yeah. Okay, so there we go. Stepwise mechanism for this Carol rearrangement again. It forms. Um ah. Gamma Delta unsaturated carbon new compound from a beta Kato, Esther and analytic alcohol using base. Um, we're also producing ethanol and CEO too. Ah, and I indicated at which steps that would be. But really, we're just trying to follow the main organic product here. Ah, and so that is Theano, sir, to Chapter 27. Problem number 57.

This is a two step mechanism, the first thin walls and elimination, which is followed by a substitution stem. Delhi mission opens the five member ring and make sell for a good nuclear fine. The base takes the proton the electron density shift to the next one, which results in the breakers off carbon sulfur bond. The intermediate is in second stage, which is substitution. The sulfur nuclear file displaces the chloride living group to form a six member ring. No first step is the two mechanism and the second step is assent to mechanism.

Under basic conditions with ethanol. This Nick, we filed an attack to generate this. That's your He'd roll intermediate. At this point, lone pair of electrons from the oxygen can come down. And if it were to keep us from ethanol group on a dockside group, we just get back to where we started. So the more interesting reaction path lies. If this carbon, carbon bond, bro, we would instead generate this. You know, late along with this die, Esther. That this you know late. Of course. Get protein ated to form the key tone form. Not at this position. If we have this a fox side in solution, we can actually Deep Roach, Nate, other proton on the more approachable, less Sterrett Clea hindered side which go on Tio react with Esther. We formed in the first step. You owe us this rearranged products. It's likely that this is going to use the major one from this step. Here, you see the base very easily. De protein ate the position in which the methyl is not there. Just because thes two protons are much more Serik lee available

We are doing this crazy cycle ization reaction starting with this, Michael. Except there also this my clicks out there. So a strong base we Can he impersonate the south position? Hershel, come back around and attack this electric file. Of course, at that position, it would not attack directly, but it would God this Michael position. Right now we have this carbon bond forming. When we have 1234567 seven member. Drink my job. These a little bit smaller. So the seven member green 1234 by 67 Carbon number seven now has this dangling esta group attached. Seven. We'll go. 12 one, two On the other side, we still have. He's that whole groups. It's now we can have our base again. Deeper Sneyd. One of these Alfa protons generate our nuclear file, which will come to attack this position Two trying to drive two dimensionally as I can. This carbon, as now forms new bond. Ready that carpet there. We still have a metal group. This position swell as Catholic youth at that position, since the way they have it drawn is this six member drain with that triangle kind of perk. Well, is this metal position at this side than the seven member drain happening here? Here we have our there. Here we have our you tell him. So if you notice these are all the exact same thing, Here's our seven member drink. Here's this little five member drink. This case, it helps for me. The highlight. This 500 ring here is actually this five member drain here. So, of course, the six members being shown on this side, it's actually this six member drain. John here. Hope that helps you visualize these two products are actually the same thing.


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