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.

(a)

Accepted Answer

Hello everyone. So in this video, I want to show how we get this compound by using a micro donor and micro scepter star material. So Michael addition is the new go feel like edition of a micro donor. Usually being an active meddling on a micro sector which is usually an alpha beta unsaturated carbon. Um It is a carbon carbon bond formation reaction. So we're gonna go ahead and give a general mechanism first and then we can apply that to our understanding and do it for this product there. So starting off with my Michael donor, we have a die ketone. So we'll have an R one group here, ketone group, another ketone group here and an R two group, the central carbon will have a proton like. So, so we can bring in any base. We'll just use hydroxide because it's the most popular we know hydroxide has a negative one from a charge since this oxygen has three long pairs. So what's gonna happen is that are negatively charged oxygen grabs a proton and forms a long pair on the central carbon. So basically home molecule remains intact except for the central carbon. So we're just gonna go ahead and redraw that again, we have our lone pair here with a negative one from a charge on this carbon. Now, we're gonna go ahead and use this lone pair to form a pi bond. Then of course, the central carbon between the carbon option will need to relieve itself. So papa and will break and form a lone pair on the oxygen. So what we get is sort of like resonance structures. Then we have our one group with the double bound oxygen, we have a new pipe bond, their single bound auction with a new lone pair giving it a negative one formal charge are two group remains unchanged. Now, the fun part comes along where we're bringing our Michael Aceptar. So earlier here, this was our Michael donor and then this right here or rather what we're going to bring in is when we add in our Michael specter. So joy General Michael Aceptar. So how maybe an R- three group, we'll just call it a pipe on there. And then our four group here with a ketone group. All right. And now we can go ahead and label this is our Michael aceptar. All right. So what's gonna happen now is that the pi bond that we created in our starting region here? That's going to go ahead and attack right over here, this carbon between the carbon carbon double bond. Because why is that because our pie or lone pair between the um on are negatively charged oxygen will want to reform our carbon Neil. So once we reform that, of course, this carbon needs to be relieved. That's why this pipeline comes in and attacks that this micro sector, carbon carbon double bound. And then between our in our Michael sector because we attack this carbon, we're gonna go ahead and break this pi bond to create a another pi bond on closer to the carbon, no carbon. And of course, this carbon carbon must be relieved. So then this little bound will go ahead and form a lone pair on the oxygen. Alright. So following along with our arrow pushing, so now our micro donor, so the original region that we use in this mechanism that remains intact, we're sort of just shifting it a little bit. So our two group with the, the bound oxygen will go ahead and move on the left side making space for michaela sector that we're attaching. So we have our pie volunteer Singapore oxygen and then we have three lone pairs and a negative one formal charge. So we accept that carbon nails like to reform. So one of our lone pairs here are going to go ahead and come down to form a pi bond. Then this double bound right here is gonna go ahead and form a negative charge on this carbon because it bears a lone pair on this carbon here. So we fall again, our arrow pushing. We've seen the left side of the molecule that remains intact. So our one group, so about oxygen, Our two group sub abound oxygen. And there are three groups. This carbon continue, our three group will not have this lone pair bearing a negative one formal charge. And then our double bond oxygen there. And lastly our our four group. So now what happens is that we pollinate our carbon with a negative one formal charge using water. So this lone pair is gonna go ahead and grab that proton breaking the oxygen hygiene double bond. So we get our final product again, are one group, double bound oxygen, our two group, double bound oxygen, our three group here are four group, double bound oxygen. So the Michael addition product contains a 15 die carbon Neil part. The newly formed carbon carbon bond is the C two C three bond. The bond that was broken during the reaction is a C three C four pi bond. So to identify the starring Michael donor and Michael sector, we have to go ahead and disconnect the C two and C three bond. So we're gonna go ahead and label it as originally given reagent. So our first carbon here, second tier 3rd, 4th and 5th race that, that we're disconnecting at the C two C three. So we're disconnecting right over here. So adding in my retros of this arrows and moving down here, my Michael donor is going to be well, on the left side of molecule remains intact. So we'll basically kind of read all that double bound oxygen, another double bound oxygen and our method group there. So again, this is my Michael donor Michael Scepter, then is going to have a fennel group with the double bound there. A key chain group here and another final group on the right. And this is my Michael aceptar. So how it forms our product then is let's see, we have a negative charge on this carbon right over here. What's going to happen is that that lone pair will go ahead and attack right over here. The long or the pipe on between the two carbons will go ahead and break and form a new pipe on there. This carbon carbon will relieve itself forming a lone pair on the oxygen. So what we do is we follow the arrow pushing here is that will form a bigger molecule we're connecting Michael donor and receptor. So get this double bound oxygen coming down to the left. We have the rest of the Michael donor. We just have metal groups actually for this part. Alright. And they were adding in the Michael sector. So we have the final group, newly formed pi bond oxygen with three lone pairs negative one formal charge and the remaining and last final group. So what's gonna happen then is that we do in hydraulics sis which should lead us to our final product. So again, left side remained intact. two Around oxygen going down bound oxygen and metal going to the right. We have our final group, another final group at the end and double bound oxygen. Alright, so all this here is going to be how we're gonna get from our micro donor Michael Scepter to our final product here.

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

Key Concepts

Michael Addition

Michael Donors and Acceptors

Synthesis Strategies in Organic Chemistry

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