How could the following compounds be synthesized using a Diels...

Question

How could the following compounds be synthesized using a Diels–Alder reaction?

a. Chemical structure of a compound with a carbon ring and functional groups, illustrating a Diels-Alder reaction synthesis.

Accepted Answer

All right. Hi, everyone. So for this question, let's determine the way that the given molecule may be created via a deals alder reaction. Now recall really quickly that the deals all the reaction can also be referred to as a four plus two psycho edition and every deals all the reaction needs two distinct components in order for the reaction to work, right, to proceed. The first of which is a dying, specifically a conjugated, dying and also a Diop. So here, right, if we take this generic diane right here, beta 13 dying, the main point is that the dying itself must be conjugated, there must only be one sigma bond in between each double bond and the Diago file. On the other hand, it can be either an all keen or an all kind, but it also has to have a pipe on. And so the Dienno file has a high affinity for the dying and so it will interact with it in a concerted mechanism. So let's go ahead and showcase how that happens like discussed previously, right? The Dyan A file has a high affinity for the dying itself. So in the first step the dienno file is going to interact with the dying and create a sort of chain reaction. But before I do so, I want to revisit the term four plus two psycho addition. And I want to point out here that my dying has four carbons which I'm labeling one through four. And my Diana file has two additional carpets which I'm going to label five and six. Let's keep this in mind. But like I said previously, the pi bond of the dienno is going to start by interacting with the da. And in this case, I've depicted the pi bond of my dienno moving towards carbon one of the diane write these pi electrons so that forces the pi bond already in between carbons one and two to shift in between carbons two and three instead. And then right, the pipe bond between carbons three and four is going to shift and it's going to interact with carbon five of the dienno itself. Now, after all this is said and done, the term cyclo addition becomes a bit more relevant, right? Because after this concerted mechanism of interactions between the pi electrons of the died and Diop we end up with a six member ring. And in, in addition to there being a six member ring, there must be a double bond in between carbons two and three. So here is your end product. Now, it's important to mention that in the example, I went over, I did not have any substituents, but you must consider the substituents that might be attached to the six number ring that forms after it deals alder reaction. And what you'll notice here is that in the very center of the given molecule is a ring that looks just like the one we drew in our generic reaction or our example reaction, except we do have a few substituents. So at this point, we can go ahead and make a split because we can go ahead and actually separate the four carbons from our dying from the two of our Diop. So let's go ahead and start with the actual d and I'm going to scroll down a little bit to give myself some space. But here I'm going to start off by drawing my actual dying because if you look at the double bond in between carbons two and three of the given molecule of the final product, then the double bonds of the starting dying would actually be on either side of the double bond in the product. So here I'm drawing that conjugated system, right? I've got two double bonds separated by a single bond. And here I'm going to go ahead and attach my substituents because I have a benzene ring on position two or carbon two. There we go. And I have an EO group on position three. I'm not happy with the angle. So let me just, there we go. But now that the dying has been established, we can go ahead and apply the same logic to the D or F because in my Dian Ahi, right, I'm going to have a double bond in this case. And I'm also going to have a few substituents which I'm going to go ahead and draw in case I forget them. But here is your answer, right? These are your two resulting products because if we go ahead and reapply the same arrow pushing mechanism that we discussed in the example reaction here, we will generate the same product because our Dian Ahi is going to interact with one of the outer carbons in the dying and that is going to cause a cascade just like the one we discussed previously. And so that right after reacting in the presence of heat is going to yield a six member ring uniting both the dying and the dying of art. So here are the substituents of the actual dienno. And here are the substituents of the day and there you have it. So here is your final answer. So with that being said, if you stuck around to the end, thank you so very much for watching. And I hope you found this helpful.

How could the following compounds be synthesized using a Diels–Alder reaction?
a.

Key Concepts

Diels–Alder Reaction

Conjugated Dienes

Dienophiles

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