Show how you would make the following compounds from a suitabl...

Question

Show how you would make the following compounds from a suitable cyclic alkene.

(e)

Accepted Answer

everyone and welcome back into this video, We are going to learn how to solve the following problem. Show how to synthesize the compound shown below from a cyclic AL keen. We understand that the start that the material that we want to synthesize is an alcohol because there's a presence of that alcohol group. And we want to propose a possible AL king for its synthesis because we're interested in an AL king. We want to think about the dehydration of that alcohol and what kind of al kinds we may form. There are two beta hydrants because there are two beta positions. Notice that this is the alpha carbon because it has the carbon alcohol group. Right? This is the main alcohol. So the adjacent positions are the beta positions. And if we remove these beta hydrants, we will get to possible al Kane's one of them. We'll have a six member ring with the double bond at this position. Right? Because we're moving this beta hygiene creating a double bond and then getting rid of water when this alcohol group gets protein ated. That would be our first possibility. And our second possibility is to remove this beta hygiene to place a double bond at this position. So we would get our next possibility where double bond is at this position. And then here we can just add our five member dring. Right? So these are two possible Elkins and we're going to think which one of the two are we going to choose. Now this one is not really good for us because notice that if we protein eight that we can get to secondary carbon, Karen's plus rearrangement of one of the cardboard Karen. So this is not really good. The two positions are equally substituted and this gives us a mixture of products for sure. However, if we think about this elk in this position is more substituted than this one, so it's not really symmetrical in terms of an alky meaning this is a good choice for us. As long as the two carbons are not equally substituted, we can think about hydration of such an alcohol. Among my apologies, hydration of such an alky into producing alcohol. Right? So this is not a good choice because the two positions are equally substituted and we are likely to get a mixture of products. Now thinking about this al keen, we noticed that we are going to add our alcohol to a less substituted position. Right? We are forming carbon oxygen bond at this position. Right? It's less substituted, it only has one alcohol substitution. This position has to alcohol substitutions and it's essentially more substituted. And we're going to add hydrogen over here because hydrogen is added to a more substituted position. Such an addition is called the N. C. Cognitive edition because this is the ante Markovic of addition. We call that the more cognitive school says that hydrogen must be added to a less substituted position. But because we're reversing that rule, we're saying this is ante Markovic of addition because hydrogen is actually added to a more substituted position. So to produce that anti Markov nick of regional chemistry, we cannot simply use an acid catalyzed hydration, right? Because an acid catalyzed hydration. Let's write it down and asset catalyzed hydration. It follows the more cosmic up through. But here, if we want to reverse that, we cannot use an acid catalyzed hydration. Keep in mind that an acid catalyzed hydration as H two S 04 and water right here. However, we are using the anti more cognitive edition and recall that this can be achieved by using Borough hydration oxidation. So what are the reagents needed for borough hydration oxidation? If you recall? They are number one boring in the presence of tetra hydro ferrin and number two addition of hydrogen peroxide and hydroxide. So now we know everything that we need. We have analyzed our beta positions. We said there were two Elkins, we are going to choose the one that is not symmetrical and we understand that the addition follows the ante Markovic of re geochemistry meaning we need to use borrow hydration oxidation and we are simply ready to draw our general reaction scheme. If we start with our six member ring Control and the Jason five member ring, right? This is basically our starting material. And we said that we want to produce a double bond at this position because it's not symmetrical and the set of regions that we are utilizing that's boring and tetra hydro ferrin followed by hydrogen peroxide and hydroxide. And it was said that based on the fact that this is an similar cosmic of addition. The alcohol group will be added to the less substituted substituted carbon and hydrogen will be added to the more substituted carbon. So we are going to draw our found product. We're just going to say that The 6th member Drang will have that alcohol and this position, which is less substituted hygiene will be added here. Right? So there's no need to show an implicit hygiene. We may just show our five members rain. So this is our final product. We may say that the cyclic al King that we have proposed is on the left with where hydration oxidation. This essentially gives us our final product. Now the correct answer choice to this multiple choice question is C However, if you have any questions, don't have states, leave a comment down below in the comment section and thank you for watching

Show how you would make the following compounds from a suitable cyclic alkene.
(e)

Key Concepts

Cyclic Alkenes

Reactions of Alkenes

Functional Group Interconversion

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