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Give a detailed mechanism for the reaction below. (8 points)HzOBrz...

Question

Give a detailed mechanism for the reaction below. (8 points)HzOBrz

Give a detailed mechanism for the reaction below. (8 points) HzO Brz



Answers

Draw a stepwise, detailed mechanism for the following reaction.

This is the answer to Chapter 27. Problem number 55 from the Smith Organic Chemistry textbook. All right, in this problem, we're giving a reaction and asked to draw a stepwise detailed mechanism for it. Okay. And so what we have here is basically ah, four plus two cycle audition, and then intra molecular Imean formation. Um, and so the first step is gonna be that four plus to Psychlo addition on, so that is gonna look like this. Okay, um, and so that's gonna form our 2nd 6 member dring. Okay, s o, uh, there's the product of the four close to Psychlo Addition. Um, and so the next thing that's gonna happen, as I said, is gonna be an intra molecular Imean formation. And that is going to go like this s of the Knights General actors nuclear file and attack this carbon carbon. Um, the electrons of one of these bonds will go up to the oxygen, and then from from this point, it's pretty much just a just a standard Emmy in formation. So hopefully everybody recalls that, um, from previous chapters. Okay, um and so this nitrogen is gonna have to hydrogen zahn It's still the oxygen is gonna have three lone pairs. So have a natively charged oxygen and a positively charged nitrogen here, Um, and so we can just call the transfer off, um, one of the hydrogen from the nitrogen to the oxygen. We can just say proton transfer, so that will get us to hear. Okay, um and so we are told there is some mild acid, uh, you know, in the reaction conditions for this reaction on dso this oxygen, um, is gonna be pro nated by that mild acid. That's little Grab this proton. Okay, uh, and so now this oxygen's been pro donated, so it's gonna have a positive charge. Uhm. And so the nitrogen, um, the lone pair on the nitrogen can add in here and simultaneously. Uh, this oxygen with its to Hodgins can take off as a water. Um, and rather than try to cram stuff and below this, I'm just gonna put the last, um, couple pictures on a couple couple molecules on the next page s o the water that I was going to take off the night surgeons loan. Paris gonna add in? As I said. Ah. And so that is gonna get us to hear. Okay, Um and so from here, the only other thing that has to happen, um, is gonna be deep pro nation of that nitrogen. So let me move all of this down, okay? It's a deep pro nation of the nitrogen, the mean, um, and that can be accomplished by water. So no surgeon's gonna have positive charge here, since it has four bonds. Um, but there is water floating around in here. Ah, and so the final step is just gonna be this deep protein nation, and that is going to get us to our final product. Okay. Um, so, uh, yeah, Here's the last step again. Here's the rest of the mechanism on the first page. So it's ah, it's a four plus to Psychlo addition, followed by intra molecular Imean formation on. And that is theano, sir, to Chapter 27. Problem number 55

Hello, everyone. So they were doing Chapter 18 Problem 56. And this for masses to draw the supplies mechanism for the fallen reaction. So we have here is that we have some sort of electron donated benzene rank, and we have some sort of alcohol and meth. Oxy reacted with a strong acid. You guys know I was, like, two Ah, substitute and make a left statement saying, Let's hydrochloric acid. Sorry, lets us sulfuric acid equal h a. So now we see that H es Felipe Association Solutions. We have h plus ions and a minus. And we have alcoholic appear with long pair electrons. So right off the bat, we consider this alcohol will prone be pro Nate and pick up one of these protons and solution. Now we have urinated water, which is not very happy to be probably it. So what's gonna happen is that I want it will try to neutralize itself, and by doing so, it will just spontaneously fall off. And only that now we have our conjured base, which is a tch s 04 minus. Kathleen, you know, here we have a second couple cat on, but if we move this. Our group over here, They're for more stable church in Carvel Cat down. So we're gonna have some sort of Carvel cotton rearrangement of crying in order to make that secondary Carbo cata into a more stable tertiary carbo. Tada, No. Now we have this tertiary Carvel cad and here and then we have a very strong electoral father. And our benzene ring is a bench entering such that it has two electoral donating groups. So we know that we can go through some sort of electoral filic aromatic. It's substitution reaction e s reaction using the two electrons that are in the pie bond as our nuclear fall going through this carbon atom and picking up this, uh, hitting this carbon this carbon kata Internet ID here where No, we know that we're going through this carbon atom because there's a taxi is directing or so and pere on this. Our group is also directing or throw in Paris, so we know that we have a double direction, a crank here. We know that there's not gonna be any chemistry on this carbon because in between two groups and it's two hysterically to hinder, to have any sort of chemistry. And we know that if you want to do some sort of insure molecular Electra flick aromatics institution that this carbon is too far away and they'll be too much strain occurring if you have some sort of intra molecular civilization occurring here. However, the perfect handed that is indeed this carbon atom right adjacent to this hydrocarbon. And now we have this cardinal cat on on loss ofher mantis titty from our benzene ring on. So what we need to do is actually is regained. Some of that air Metis ity from our that we lost in our benzene earned make this more clear that this hydrogen is from this Adam. So it's a very large Hye Jin bonhomie clear that's belongs to this carbon here. And not only that, will this reaction was acid catalyzed. So so far, we have the conjugated base, but we need to reform our ass a catalyst. So in order to do that well, we can pick up this proton here making about you make about your break about this bond will break and it is going to reform Ara Metis ity onto our benzene ring, stabilising it and reform our age to us off for and we form water in the first step right here, and we reef and reform our product of interest.

So this question is us too. Brothy detail mechanism off this reaction. So with H plus, again, the first step would be a problem. Nate, off the alcohol over here and generate arse onem iron, um, which make it become a good living group and the departure off water will generate. But this couple car tire now, the migration of this bond. So here. Well, Jerry, the next intermediate. In order to do that, we have the label. The cab on 12 3456 It's a six member of ring again. This is three far 566 connick, two one. And this too. And one has a method group. And two now has the, uh, of have scalpel cata now as ovo to minus. Well, then attack this hydrogen and that will found the brought us

This question, as a strong mechanism of this reaction is the first step would be, as usual, attack off the lamp air, oxygen on the product. Jerry, the ox Oranje tie in over here and then breaking this month will generate the alcohol. And the cab broke a tie in Over here. And at this case, CIA three c 00 minus. We will attack a broader. This one. Come back here and that will form the orb in over here.


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