Oxidation of Alcohols

[MedPR]

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Tertiary alcohols can't be oxidized, since there is no hydrogen to remove.

Primary alcohol is oxidized to an aldehyde, which is further oxidized to a carboxylic acid.

Secondary alcohol is oxidized to ketone, but can the ketone be further oxidized to an ester?

 

[MT Headed]

Yes.

 

[SaintJude]

The Baeyer-Villiger Oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts ketones to esters
Can be carried out with peracids, like MCPBA.

But don't think this is on the MCAT!

 

[MedPR]

The Baeyer-Villiger Oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts ketones to esters
Can be carried out with peracids, like MCPBA.

But don't think this is on the MCAT!

Baeyer-Villiger is in TBR 🙁

 

[SaintJude]

I had a passage on my last Kaplan Practice Exam No. 4 about Bayer-Villiger oxidation from ketone --> esters. Passage-based but didn't do well on it. Anyone have some salient points about this mechanism they'd like to share?

 

[thestrokes14]

Secondary alcohols cannot be oxidized to form esters....they only form ketones. It would be unproductive to think about whether they can in some obscure reaction because if this question were a discrete question, the answer would be an oxidation to a KETONE every single time. If you are trying to predict passages, I don't see this being a very good passage topic either.