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CM Provide a detailed stepwise mechanism for the acid-catalyzed condensation reaction between cyclohexanone and HzNOH:Provide the structure of the major organic pro...

Question

CM Provide a detailed stepwise mechanism for the acid-catalyzed condensation reaction between cyclohexanone and HzNOH:Provide the structure of the major organic product in Ihe rcaction below (shou stcp by step neuction sequencekCHl(aree) 40wvethe produc of each step andthestnicture ofthe final product inthe eaction sequenceomoHOChpon 4 Ep Htsh Roomnd

CM Provide a detailed stepwise mechanism for the acid-catalyzed condensation reaction between cyclohexanone and HzNOH: Provide the structure of the major organic product in Ihe rcaction below (shou stcp by step neuction sequencek CHl(aree) 40 wvethe produc of each step andthestnicture ofthe final product inthe eaction sequence omo HOChpon 4 Ep Htsh Roo mnd



Answers

The Stork enamine reaction and the intramolecular aldol reaction can be carried out in sequence to allow the synthesis of cyclohexenones. For example, reaction of the pyrrolidine enamine of cyclohexanone with 3-buten-2-one, followed by enamine hydrolysis and base treatment, yields the product indicated. Write each step, and show the mechanism of each.

Here's the structure of diet used by donation off conjugated directing with PR Right there. Possible structure complete initial dating Aaron Final Growth which formed after the reaction with immediate traffic with a transgender on that Z and draw problems Mexico each other the problems. That or effectively you could put 71 all those problems or charge on this cover. It was just a construction off with they produced. Yeah, by the domination over dating. So new religion would be one rose or from in the first case, this cover over dating is a this'll dating in the that is experience. With respect to this double tomorrow, the second option is for information off this problem and that can be achieved by the reaction the second begin on. This problem will be coordinated on configurations around work. Double bonds can where work and give CIS or trans a charge. What? Or another perfect keep with offline In the first case, with their attention of this government and yeah, a woman also can the island system for Prince Iceman or this is a problem our partners should be through this product also, or scared of ice cream

Continuing our work with all kinds and all kinds. These are double and triple bonds, respectively. Here we're focusing on a mechanism. So I drew up my starting materials first. So what we see is up Oxygen atom will take a proton than what we have is a protein ated starting material on a minus. So in the next step, we see the loss of this group that is Ah, a wage to positive than what we have is the following. So everybody primary carbon cat ion There is our positive charge. It's moving onto the final steps. So we take our parliament Copycat ion What we see is a shift. We go through a transition state that I'll draw over here. So when we have transition, states were often used dashed bonds and that's not too reference thes stereo chemistry in three D space. That is to tell us what bonds are breaking and what bonds are being made. Transition state with a double dagger. Now what we have is instead of a primary carbon Qatar and we now have a tertiary carbon cattle, which is a lot more stable due to that migration. This is not a tertiary Carver Catalan. So in the 2nd and 3rd step that we looked at the ionization and the rearrangement may may occur Simultaneously done What we see in the final step is that we have Proton here. So we have a base Welcome. And take that proton on then what we do is we form an Al Keen. Ah, Now we form to miss out to beauty.

This is the answer to Chapter 20. Problem number 77 fromthe Smith Organic chemistry textbook. This problem says reaction of occitania with metal. Magnesium bromide followed by water, uh, forms a compound that shows a strong absorption in its eye. Our spectrum at 30. 632 100. Ah, and then we're given and it more data, um, and asked to draw the structure of the product into red a mechanism that illustrates the products formation. Okay, um and so the first thing to do here, eyes to look at this I r um, And hopefully we know by now on, I R peak between 32 3600 is gonna be from an alcohol from a no h I still even alcohol in this molecule. Um, okay. And then looking at the anymore data eso we have, Ah, 0.94 ppm. Triplet. That integrates to three. So that is gonna be a meth A group. Um, next to a methylene group, uh, our next signal eyes a multiplayer that integrates to two. So this is a methylene. The next signal also integrates the two. This is also probably a methylene group. We have a single it that integrates toe one a 2.24 p p. M. S. So I'm gonna tentatively say that this is the hydrogen on our alcohol. Ah, and then we have, ah, 3.63 ppm triplet. That integrates to two. So this is, um, another methylene. And I'm gonna say that this is the methylene that is bound to the alcohol. And that's why it's so far downfield, because it's d shielded by the alcohol. Um, and so looking at Aah these five signals that we have, um I'm going to say that the structure of our product is this. So, uh, one beautiful. Um, and then as far as, ah, a mechanism that illustrates its formation. I'll do that over here on the left. It's a pretty straightforward mechanism. So we have the occitania, um, metal. Magnesium bromide is going thio act his nuclear file and add to the carbon that's bound to the oxygen here. The carbon oxygen bond will break in. Those electrons will go to the oxygen. Ah, And so after that first step, we're here, um, with the alc oxide hoops. And so, uh, there is, of course, a negative charge here. Um, And then, uh, the water, The quenching step is just gonna protein ate that Alcock side that we just made. So rather than try to squeeze, squeeze it in right there, I'll put it down here. Okay, on. So there we go. There's the mechanism that accounts for this product. As I said, it's a pretty straightforward mechanism. Ah, and that's the answer to Chapter 20. Problem number 77.

So, in order to tackle this question, when should know what is mechanism Now? Basically, make any self is the past description off any chemical reaction Step by step description, description off a media action that is called mechanism. Secondly, you know when three beauty dine, that is CS two double bond ch See it from the Taliban ch two. Okay, so this is a 13 butor dying. 1234 So 13 butor dying? No. When it's very sided to it. Hydrogen bromide. What happens? You know the bill bond Abstract hydrogen from which were So what do you get is we'll get this car book at him ch teau double bond ch Then ch positively charged so positively charged C h two. Yeah, it's nothing but ch three You can see So these bombs a ch three. Okay, now this. Undergo faster. Take off br minus br minus and you'll get a printout. So what is the platform that is CS two double born ch name ch br ch three. Okay, so this is form fast. And now whatever this against a cargo Nieman one is from Okay, so that undergo rearrangements. See, it's ch ch three plus. So this double bond make it's my greater or here and he'll get another a resonance or economical structure that is ch two glass then ch the long ch ch three. Now on this on this reaction is a little bit slow. Oh, br minus will attack. I will get the product as br ch two ch double bond ch ch. Three So this is oh, one, uh against a 1234 So this is one bro mo one but almost butte toe in. And this is 1234 So this is three Brahma Butte in three drama beauty one in now, according to say safe through You know this one Bram Hope to building form is as a major blocked as per se gypsy because these polyphony carbon it's more substituted on this one. Promise form is a lesser product, but actually this car bucatini is form around, you can say, and indeed percent they indeed, percent on this card book a day in his form around 2%. And that's why the first one is a major plug. And second when he said minor plot


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