Question

Oxidation of ketones?

I know ketones are impossible to oxidise at normal conditions, but I heard they can be oxidised at specific conditions. What conditions are they, and what happens to the ketone?

Answer 1

Well, I believe they can be oxidized UNDER HIGHLY OXIDIZING conditions....

Explanation:

We take acetone, in which the ipso carbon is `stackrel(+II)C`...

This is in equilibrium with the enol...

`H_3C-C(=O)CH_3 rightleftharpoonsH_2C=C(-O-H)CH_3`

I presume, under strongly oxidizing conditions, the enol could be oxidized to give `CO_2` and `HO(O=)C-CH_3` i.e. `stackrel(+IV)CO_2` and `stackrel(+III)C`.... These conditions would probably include a hot acidic medium, and some vigorous oxidant such as `HMnO_4`, or `H_2Cr_2O_7`...

As far as I know, this oxidation is without much synthetic utility in that you are breaking `C-C` bonds...something which you usually do not want to do.