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Topic: oxidation of tertiary alcohols  (Read 3912 times)

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Offline eunChae

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oxidation of tertiary alcohols
« on: April 02, 2010, 01:29:44 PM »
Why are tertiary alcohols resistent to oxidation? (to aldehydes or carboxylic acids)

I know why they cannot be oxidized to ketone when we use chromic acid.(Because at the step of leaving of chromate ester,there is no available hydrogen atom to be eliminated.)

But what about the other reagents? Is there any standard procedure to oxidize tertiary alcohols to ketone,carboxylic acid or aldehyde?

Thanks in advance...

Offline Schrödinger

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Re: oxidation of tertiary alcohols
« Reply #1 on: April 02, 2010, 03:30:37 PM »
What happens to the molecule when you oxidise a tertialy alcohol? Does the hydrocarbon chain remain intact?
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Offline hobobot

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Re: oxidation of tertiary alcohols
« Reply #2 on: April 05, 2010, 09:01:38 PM »
When in doubt....add Hot HNO3.

It's one of the few things powerful enough to cleave the C-C bonds. If you do this to acetone you would end up with acetic acid and CO2. (I don't know the mechanism)

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