What reagents should be used to prepare the following compound...

Question

What reagents should be used to prepare the following compounds?

c.

Accepted Answer

All right. Hello everyone. So this question is asking us what reactants and reagents are necessary to synthesize the following compound via an enemy intermediate. All right. So first, what is the role of the enemy intermediate in this overall synthesis? Now, the given compound can be produced via the conjugate addition of an alpha beta unsaturated carbonel compound. So essentially the enemy intermediate can be used to create a new carbon carbon bond to the beta carbon of the alpha beta unsaturated carbo compound. Now recall here that enemys are the product of a car bono compound with a secondary Amin. So taking acetone here just for the sake of example and combining this with a secondary amen. In this reaction, the carbon compound undergoes condensation resulting in the removal of water and the formation of the enemy. So because the static amine is secondary, it only has one proton attached to nitrogen. There is now going to be a single bond between the carbon carbon and the nitrogen of the secondary amine. However, there's now going to be a double bond in between that carbon carbon and the one next to it or at least it was the carbon carbon in the beginning. Now, the resulting amine therefore is going to be nucleic but specifically at the beta carbon relative to the nitrogen of the enemy itself. And that's convenient because that allows us to establish that new carbon carbon bond between the beta carbon of the enemy and the beta carbon of the alpha beta unsaturated carbon compound. So from there, the enemy can easily be hydrolyzed under acidic conditions to restore the original carbel. And so all this is to say that now we can go ahead and talk about how to separate the target product into the starting ketone. And the alpha beta unsaturated carbonel compound lets look at the gibbon. Now, considering the target product that we have. In this case, we can pretty easily separate this into two distinct car bono compounds because we have one key toone outside of a ring and another as an ocho group branching off of the ring itself. These are two groups that we can go ahead and separate from each other where one of them is the starting ketone and the other is the alpha beta unsaturated compound or alpha beta unsaturated car bono compound to be specific. So here we can say that the ketone inside of the ring is the starting ketone or our starting material. And the carbon chain branching off of the ring is the alpha beta unsaturated compound. This is convenient because we do have two carbons in between both car bottles outside of the rink. And so it's these two carbons that are going to be or that are going to have a double bond in between them in the structure of the alpha beta unsaturated compound. So we can go ahead and separate our starting materials. And from here, lets talk about our synthesis. So the first step is the formation of the enemy. So we can take cyclone though, before we continue with the synthesis, I do just want to point out that there is a different way to split the target product into the two organic starting materials. Specifically, you could separate the carbons that I've labeled alpha and beta to create a different ketone and a different alpha beta unsaturated carbon. But for this example, lets go ahead and proceed with Cyclin. So we have cyclops, anone and a secondary amine reacting with trace acid to eliminate water and ultimately produce the enemy. So now there's going to be a single bond between the carbon carbon and nitrogen. Nitrogen retains the art group that it has. And now theres going to be a double bond between the initial carbonel carbon and the one next to it. All right. So from here, we can introduce nucleic edition of the alpha beta unsaturated compound and with regards to the mechanism, just to showcase the structure of the intermediate and explain it. The pi bond in between the two carbons of the enemy is going to use its pi electrons to go ahead and establish a bond with the beta carbon, the beta carbon of the other compound. So from there, a new bond is established between them, a new bond is established between them. But now there's going to be a double bond in between carbon and nitrogen just for the sake of making sure that the carbon atom nitrogen is attached to is not going to have an incomplete octet. But from here, we move on to the final step, which is the hydrolysis of the enemy intermediate. So we introduce some HC in the presence of water to restore the original car bal. And we also have an ammonium ion stemming from that secondary amy, but there you have it. So on the bottom of the screen here, I'm just going to go ahead and rewrite the synthesis just so that you can see it as it's depicted in the answer choices. So we have our ketone and our secondary a mean to start off. And in the first step, we had trace acid to go ahead and produce that enemy, followed by nucleic edition with the alpha beta unsaturated ketone. And then lastly, we used some HCL diluted in water to hydrolyze the enemy intermediate and restore the original carbona. And so with that being said, thank you so very much for watching. And I hope you found this helpful

What reagents should be used to prepare the following compounds?
c.

Key Concepts

Reagents in Organic Synthesis

Functional Groups

Reaction Mechanisms

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