Show how you would use anhydrides to synthesize the following com...

Question

Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.

(a) n-octyl formate 
(b) n-octyl acetate

Accepted Answer

Hey everyone and welcome back in today's video, we are going to show how you would synthesize the following compounds using anhydride, a isopropyl format and be isopropyl acetate. If we draw the two structures a isopropyl format essential implies that you have an isopropyl group Bonded to Form eight. So that would be oxygen. Carbonell group and hydrogen. That's our Esther. Right? So that's the first structure that we want to synthesize and be the main difference is that we have isopropyl acetate. So if we drew an isopropyl group because it's an acid eight instead of having hydrant here, we will have a methyl group. Okay, that's our other Esther that we want to synthesize. And if you recall whenever we react and high tribes with alcohols, we can say alcohol plus and high tribe. This gives us an answer. So thinking about this reaction, we can simply break down our Esther in each case and we may notice that we can easily get our carbon compounds or carbon parts that will correspond to an high tribes. And the remaining part over here corresponds to our alcohol. So in each case we are starting with an alcohol which is isopropyl alcohol. So for a we have our isopropyl alcohol and we simply need to think about the remaining part of the molecule that we God right? Essentially. For the first part we have our form eight oxygen, let's draw it in a way. Such that hydrant is pointing to the left. So now we have oxygen over here and we want to turn an anti tried out of it and it's very easy to do. So we can essentially add another carbonell group because an anti tribe must have a carbon group on it to oxygen followed by another carbon group. Right? And essentially here we can just add a metal group or whichever group you prefer. Doesn't really matter. So this would work for us. And let's see how the reaction takes place. The lumpy and oxygen from the alcohol will attack format. In particular, this carbon ill is more reactive than this one because it's an AL to hide. Right? And al the heights are more reactive than ketones. We are going to break our pi bond, restore it, followed by the loss of the leaving group. We have auction over here. So we are going to produce our car box late and iron. That's why it doesn't really matter which group you had here because this is your leaving group. And then when you D protein ate it, you're going to D protein eight. This hydrogen. You will gather the desired product. You can simply notice that if you drew a format oxygen double bonded, then you would have your hydrogen. And on the left side you're essentially adding this oxygen from the alcohol which contains an isopropyl group. So this is how we get isopropyl form eight. This will be our final product. So we got our synthesis and we can simply say that this is our reaction scheme for a And similarly, if we think about reaction be, we already know which alcohol to use. Once again we broke that bond and we noticed that the remaining fragment that corresponds and alcohol of course, as we said before this auction actually belongs to our alcohol. Right? So when we are breaking our structure apart, we get our isopropyl alcohol. Plus now thinking about anhydride, we already know one part of our and high tried that would be carbonell group. We may simply notice that there is a metal group now. So instead of having hydrogen here, we're going to add a metal group. And how old that we have to do. We just need to add oxygen, another carbon ill group. And once again, any substitution that you want to use here. Let's suppose that we are just going with a metal group, we don't want to make this site more reactive so we can just use a metal group. We don't want to use hydrogen because we want to make sure it's a key tone part. And now once again, what's happening here is that the lone parent oxygen will attack. Now it doesn't matter which carbon ill because they're equivalent to each other. We're breaking the pi bond, restoring it. That's for by the loss of the leaving group and we are getting our product we of course need to d protein eight that hydrogen from the alcohol. And if you notice you can just draw your carbonell oxygen on one end, you have that metal group and on the other end you're bonding this oxygen, which contains an isopropyl group. So this is how you're getting isopropyl acetate and that would be it. We got our synthesis schemes. We have shown how to get the required products. We are simply using isopropyl alcohol in each case and using two different and high tries to get our two products. That said, we may conclude that the correct answer to the small cultures question is C However, if you have any questions, don't hesitate, sleep very comment down below and thank you for watching.

Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride. (a) n-octyl formate (b) n-octyl acetate

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