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Question 9 (10 points) Draw the arrow-pushing mechanism for the following reaction:HHHOOH...

Question

Question 9 (10 points) Draw the arrow-pushing mechanism for the following reaction:HHHOOH

Question 9 (10 points) Draw the arrow-pushing mechanism for the following reaction: H H HO OH



Answers

Draw the mechanism for the following reaction:

This is the answer to Chapter 11. Problem number 67 Fromthe Smith Organic chemistry textbook. Ah, and here were asked to draw a stepwise mechanism or about this intra molecular reaction. So we're going from one ring, 22 rings. Ah, and we have an AL kind and an alcohol on a double bond inside the ring on the double bun inside the ring actually isn't isn't going to do anything. Ah, and so this is gonna be a reaction featuring the alcohol in the alkaline. And so we have former gas it here. Ah, and the first step in this reaction is going to be form a gas it protein aiding this alcohol that's gonna look like this. So we now have the pro donated alcohol here. Okay. Uh, and so, uh, this carbon oxygen bond can break, and, uh, the H 20 here can leave as water. Oops. And so we now have a corporal cat eye on here. Um, and the electrons in the al kind can, uh, act as nuclear file. These electrons can a shift over here to the carbo cat eye on. And so that's gonna be how we form our second five members ring here, so we now have Ah, a fused by cyclic ring system. So these two rings, uh, so have our double bond there. Ah, And now have this here. Okay. And we'll have a corporal cat eye on on this Corben. Um, and so there's water in this system, uh, in the water is going to add to that carbo cat eye on. So this, um, So now, after that, we have this product, so there's a positive charge and only one lone pair, uh, on the oxygen here, Um, and so we can, um, use that form a tie on from the first step. Uh, so this guy's still floating around. Ah. Native charge there can come and grab a proton. And, uh, after that happens, we will be, um, in an eternal form. I'm actually gonna move this a little bit. Okay? So, as I said, we'll have Ah, the eternal here. And so from the e. No, um, we can, uh, essentially just talk to memorize. Um, but the actual mechanism for that is gonna look like this. So we have former gas it again. Uh, the electrons of this double bond will grab proton comm protein ated. And so we will be here with a carbo cat eye on here. And thes electrons can go here to form the new carbon oxygen double bond. Oops. That was wrong. Okay, carbon oxygen, double bond. The oxygen is gonna have a positive charge. And one lone pair. Uh, and so now all that has to happen is, uh we could say water. Or we could say, Ah, the con ticket base, Um, of that former gas it. So the form a tie on again, um, can come grab this proton use electrons can go like that. Ah, and then that's it. That gets us to our final product here. Okay, s so there. There it is. That's the stepwise mechanism for this reaction. Um, yeah. So it's ah, a pro nation water leaving, uh, the al kind acting as a nuclear fire on adding that carbo cat eye on to form a second ring. Ah, and then, um, water adding to carbon. Ah, that's that's the new location of the car boot cat eye on, uh, that added waters D protein ated. Um, and that's basically the eagle on. Then we just talked to him a rise from the eternal to the key tone. And that's the answer. And that's the answer to Chapter 11. Problem number six.

Hillary won. Today we're doing Chapter 23 form 60 Mistral masses to draw the stepwise mechanism for the falling reaction. So we have Is this on had a monocle here on DH? What we're doing is we're reacting with strong base. So after reaction of that strong base, what's gonna happen is that we're in a deep roomie, one of the protons using this option and I own and deep resonates this Alfa Croton making by your makeup on You're breaking bon and those two electrons and that signal bomb, they're going to go into that oxygen nucleus that on that carbon nucleus. So now you have and I only Corban on, which is very nuclear feel like and very reactive. So it's going too easily react with this election file that you add on one of these carbons making about your makeup on your break, a bond and the bonds in the break. No, What you have is one to carbon and another Fox and Anna are on, and I was auction. Ion can actually react with one of these electoral Filic Carbonell carbon centers to form an intra molecular cycle ization reaction in which you form a new signal bond making bonds. You break this, Cardinal Bond, This criminal bungle collapse back down And they needed kick off your leaving room being this death oxide. So then what you have is now the cyclical structure here with your cardinal here in office. Carbon all your ethanol. So long or actually, it's eat your minus. And that's where this acid comes in Because it was going pro, Nate. Everything and make everything neutralized to form your final product with ethanol.

With With him we live in I dried. First thing that Volker is thie nuclear Filic edition of this hydride source Both Then produce This is Tetra. He'd ral intermediate. He with him will be the counter ion to the oxide Then this chloride get kicked off she'll have to be with you Counter Ion It's now if produced and Alba hide that's all. The hide is very reactive. It will still react with another equivalence of with him Aluminum hydride Now, once we formed this tetra he'd roll into media will notice that there are no good leaving groups. So the Alcock side is going to stay as the species until we get Teo Step two, which is the crunching of this reaction. It's water, Of course. Now this step Harlock oxide can get pretty nated. You'll lose with young hydroxide and produce ethanol

What you understand the mechanism. This reaction. Let's examine the reaction first. The substrate is a tertiary Allied. Yeah, and the products consist of a substitution product put in an elimination product. Does your inner light can undergo substitution or elimination under my basic condition? No, either Off this product for mission involves a car, bucket and intermediate, which can be formed by the removal ofthe reminded post. Really, the Suri car look attend forms, and this car, like a ten, either takes Electron from the nuclear file to give a substitution product court. It can lose a bitter proton look at the elimination product.


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