A reaction for converting ketones to lactones, called the Baeyer–Villiger reaction,
is used in the manufacture of plastics and pharmaceu- ticals. 3-Chloroperbenzoic acid is shock-sensitive, how- ever, and prone to explode. Also, 3-chlorobenzoic acid is a waste product. An alternative process being developed uses hydrogen peroxide and a catalyst consisting of tin deposited within a solid support. The catalyst is readily recovered from the reaction mixture. (a) What would you expect to be the other product of oxidation of the ketone to lactone by hydrogen peroxide?

Question

A reaction for converting ketones to lactones, called the Baeyer–Villiger reaction,

Chemical reaction showing ketone and 3-Chloroperbenzoic acid forming lactone and 3-Chlorobenzoic acid.

is used in the manufacture of plastics and pharmaceu- ticals. 3-Chloroperbenzoic acid is shock-sensitive, how- ever, and prone to explode. Also, 3-chlorobenzoic acid is a waste product. An alternative process being developed uses hydrogen peroxide and a catalyst consisting of tin deposited within a solid support. The catalyst is readily recovered from the reaction mixture. (a) What would you expect to be the other product of oxidation of the ketone to lactone by hydrogen peroxide?

Accepted Answer

Hello. Everyone send this video. We're dealing with a beer Villager reaction here and were given this example of this reaction. We see here that we're going from this ketone dealing with this acid to not get a lot done. So, same exact thing here with this ketone here, we're reacting with hydrogen peroxide. And when we asked being asked, what's the product that yields from this reaction? So when we add a hydrogen peroxide, we will insert an oxygen atom at the most highly or the most highly substituted carbon. So, you see out of all these different carbons here on our six member ring, you see here the one that's most sub situated is going to be one with our methyl group, which just this one carbon right over here, I'll go ahead and mark that as well and its sub situated because it only has one substitution of metal. The other ones don't have any. It's just consisting of two other high jeans. So we'll go ahead and add an oxygen atom into this carbon here or in place of this carbon here, I will go ahead and expand this ring. So right now we have six member in this ring, will now have a december seven member ring also go ahead and number this. So we remember where the methyl group goes. So starting off with our carbon that consists of a carbon auction double bond. So we'll start numbering up here. So 12345 and six. So now let's go ahead and draw out the seven med. Moving. So we're basically putting the oxygen here, we'll continue with our drawing. All right? So now let's see. We're preparing the method group at So we have 12, 345 and six, and I just didn't include the auction because we didn't consider it in this story material here. So we said that carbon to has this mental group. So we see um carbon number two over here. So that's where we'll go ahead and add that method group. So then this right here is going to be the product that results from this fallen reaction. Alright, guys, thank you all so much for watching.

Verified Solution

Key Concepts

Baeyer–Villiger Reaction

Oxidation and Reduction

Catalysis