Show how the following products might be synthesized from suit...

Question

Show how the following products might be synthesized from suitable Michael donors and acceptors.

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Accepted Answer

Hello everyone. So in this video, we want to show how this given compound here can be prepared using my donor and micro acceptor starring materials. So first of all, let's go into some details about what the micro reaction is. So this is a nucleic addition of a micro donor which is usually a stabilized Enel on a micro acceptor which is usually an alpha beta unsaturated carbon neal, it's ac C bond formation reaction. So let's go ahead and first paste a general mechanism for a michael addition reaction show hydris out myself here. So let's explain the drawing that I have going on again. This is the general myre action reaction. So first, here we have a my donor again, that's usually a stabilized elite and then we have a base to remove our alpha hydrogen. So this here is going to be where the alpha carbon is. So the alpha hydrogen is the hydrogens that this alpha carbon contains. So we have a base here that just depos this alpha carbon or alpha hydrogen. So we create the stabilized en ate here and it's stabilized by these two Carboni groups right next to it. Then this E A will go ahead and RT with our micro acceptor. So this over here again, this is usually an alpha beta unsaturated carbon neal. So beta carbons and Carboni carbons are both electrolytic. But our weak base are going to react with our beta carbons which give us a conjugate addition product. And then Shan basis will react at the carbon neo carbon which gives you a direct addition. So in our case here, we want an attack at the beta carbon. So taking a look at this, my acceptor here, this is our alpha carbon. This is our beta and we see here that definitely we do react at the beta carbon. All right. And the Carboni groups do like to reform. So here in this intermediate, we see that there's three lump pairs on this oxygen but to create or to reform our carb group, one of these on pair will come down creating a pi bond. And this pipe bod here will create a negative charge on this carbon here because we have an addition or we have an additional formal charge and that results from our lone pair here. All right. And once we get this negatively charged carbon, of course, we have our lone pairs taking up this proton here from H2O so that it can go ahead and lead us to our final product. Again, this is just the general reaction here. But all these R groups could be either hydrogens or really linear long linear chain. So the meal condition product contains a 15 di carbon part, the newly formed carbon carbon bond. As we can see from this general reaction is the C two C three bond. And the bond that was broken during the reaction is the C three C four pi bond. So to begin properly, by identifying our micro donor and micro acceptor, we have to disconnect our final product here at the C two and C three bond. So let's first number, our carbons here starting off from the left, we have 1234 and five. Again, we're disconnecting at the C two. So this carbon here and C three bond, that means it's this bond here. So if we were to break it apart, what we can get from this is going to be first our micro donor. So we have our H three C then double bond O then a coo E T. And of course, we have to make sure we don't lose any carbons or gain any random carbons. And this is also why we also labeled these carbons like soap. All right. And then again, this is our Michael donor and then from a meter, we have a Carboni group, of course. And this pi bond here again, this is our Michael acceptor. All right. So let's kind of draw a brief overview of what our reaction should be looking like. Let's do this down below. Let's go ahead and scroll down for more space here. All right. Again, I'll go ahead and start off by drawing the Michael donor. So we have a stabilized in. So we have this extra long pair on our carbon that bears a negative one formal charge. And then we have our alpha beta unsaturated carbonyl group here. So we have a carbon group and then we have this pyon at the end. So the stabilized innate is our my donor. And of course, by default, the other one will be our micro acceptor. All right. So what's gonna happen is, of course, the lone pair will go ahead and react at our beta carbon. Again, this is our alpha and it's our beta carbon at the way at the end. So it does react there. And what we get is see. So we have a Caro group here. Our coo E T group comes down, continue our chain. This original Carboni group from the micro acceptor will become a negatively charged auction group. And once we get that, we've already said that the carbon neal group likes to reform, then the pipe bomb will create a negative charge on our carbon. And after step one being hydrolysis and then finally do carboxyl, we will get our final product. Again, we have hydrolysis coming in. First, second reaction will be a decarboxylate. Again, that leads us to our final product with two Carboni groups at the end. All right. So this again is going to be my finalized general reaction and the micro donor is over on the left and the micro acceptor is over to the right. Again, the micro donor is going to be a stabilized elate and the micro acceptor is going to be a alpha beta unsaturated Carboni.

Show how the following products might be synthesized from suitable Michael donors and acceptors.
(c)

Key Concepts

Michael Addition

Michael Donors and Acceptors

Carbonyl Chemistry

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