Predict the products, including stereochemistry where appropri...

Question

Predict the products, including stereochemistry where appropriate, for the m-chloroperoxybenzoic acid epoxidations of the following alkenes.

c. cis-cyclodecene

d. trans-cyclodecene

Accepted Answer

Hey everyone and welcome back in today's video, we are going to tackle the following problem provide the products for the jeep oxidation reactions of the following Elkins through meta chloral proxy Brunswick acid include stereo chemistry where applicable. If we look at this problem, we have two parts to solve A and B. And we will look at them simultaneously because in A were given cycle noting and in B we are using trans Cyclone in as our starting material. So because there are cis trans high summer, we are just going to draw both of them simultaneously. Cyclone in implies that we have a nine member drinks. We can draw a nine member drink first of all. And because for part A we have this version of it. We make, we want to make sure that the double bomb is added to this position so we may add it here. So the to al hill groups are on the same side of the double bond. Now, in contrast, if we think about the trans eyes murmur again, we want to make sure that we draw a nine member ring and we can place our double bond at the transposition. So I suppose we're adding it here because the two alcohol groups are on opposite sides with respect to the double bond. So these are our eyes murders. This is the cis alK in and this is the trans one. Well done. So now we want to indicate the presence of meta chloral proxy benzoate acid, which as you may recall is often shortened S M C B B A. The common solvent that we're using is die chloral methane. So we may also add that. And now let's think about it as the problem suggests we have an iP oxidation reaction. So we are going to break that double bond and we will add any epoxy group. In other words, will be forming two carbon oxygen bonds and this will be like a cyclic ether which we call epoxy side. Same thing goes here. Right. But the most important thing about this problem is to make sure that stereo chemistry is obeyed. And that makes sense because if you look at the cis elkin, the reaction of methyl chloride peroxide, benzoyl hysteria specific meaning we are retaining that sis arrangement. Let's start by drawing our ring. So we understand what that means. In particular if we withdraw our ring without the double bond. Since as you know, we are breaking that pi bond, we need to make sure that do to the fact that this is this arrangement. We're also adding oxygen insists arrangement. Such that we're going to add oxygen on T wedges. So that is pointing up and that means the two hydrogen atoms will be pointing down each in sis arrangement. So notice how es ist version of an alkaline actually produces a sis compound or boxes in particular. And it's also important to understand that this is a cis miso compound. You may wish to see how there's a horizontal line of symmetry and one part of the molecule is symmetrical to the remaining parts. So it's a meso compound we're not thinking about in and tumors here due to that internal plane of symmetry. So there's only one product formed and we may say that this is our major and the only product for the first reaction. Now moving on to the second reaction because this is a trans AL king, we will be performing performing a trans edition and the Parkside will have trans arrangement. Now, this is very important to understand if we have a reaction between a trans al king and meta closer approximations OIC acid. We understand that this would be syn addition because in particular meta chlor approximations OIC acid performs a syn addition. The products will be a very scenic. Therefore, there will be two products a pair of an anti immerse. Right? So if we know that we are essentially going to add oxygen to these two carbon atoms to form any pox side, we're going to break the pi bond. So we may start by redrawing the structure. And now this is where we have to be careful we have this in addition. So let's suppose that oxygen is added to these two carbon atoms. And we understand that because we start with a trans arrangement, we also want to make sure that this compound also shows a trans arrangement. What we can do here, we can essentially think about changing the positions of these two AL kill bonds. Right. We may essentially state that one of them is pointing away from us so basically dashed and the other one over here is wedged. So if we perform that, we may simply see something like this. There will be a wedge at this position indicating that this part is pointing up and then at the remaining position we said ok that this was a solid line, but this position should be pointing down. So we clearly see that this is a trans arrangement, right? And it makes perfect sense because one alcohol group is pointing up, the other one is pointing down, which implies that this is trans and we may also add those implicit hae jin's if you wish, we may someplace show that one hygiene is pointing down here and the other one is pointing up now, similarly to that structure. As we previously said, if we have a trans al caine, we have seen addition, we're forming a systemic mixture of finance, commerce, so our next product would be an end to more of the first one. So if we draw it, we may not think about the addition of that oxygen. Again, we will add it on to solid lines but now, because it's an anti armor, we will essentially reverse the spatial arrangement of these two alcohol groups. If this was pointing up Now, this bond will be pointing down from a wedge to a dash. So we're getting this kind of looking bond and for the remaining part we are going to add a watch because originally we had a dash, so this would be our in and humor. We may simply say that this is again a trans arrangement, right? And we may similarly add those implicit hydrogen atoms. One of them is over here pointing up and the other one is pointing down. So we now clearly see that these two are in and commerce. We have two products for reaction. Be we may now conclude that the correct answer to this multiple choice question is C. However, if you have any questions, don't have states, leave your comment down below in the comment section and thank you for watching.

Predict the products, including stereochemistry where appropriate, for the m-chloroperoxybenzoic acid epoxidations of the following alkenes.
c. cis-cyclodecene
d. trans-cyclodecene

Key Concepts

Epoxidation

Stereochemistry

Cycloalkenes

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