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Topic: Arenes oxidation with KMnO4  (Read 3133 times)

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Offline Rutherford

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Arenes oxidation with KMnO4
« on: February 09, 2013, 10:53:29 AM »
In the picture attached there are two arenes: tert-butylbenzene and durene. Which one of them is not readily oxidized with KMnO4 and why?

Offline discodermolide

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Re: Arenes oxidation with KMnO4
« Reply #1 on: February 09, 2013, 10:58:43 AM »
What do you get when you treat toluene with KMnO4?
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Offline Rutherford

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Re: Arenes oxidation with KMnO4
« Reply #2 on: February 09, 2013, 11:05:28 AM »
Benzoic acid. How to apply this here?

Offline discodermolide

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Re: Arenes oxidation with KMnO4
« Reply #3 on: February 09, 2013, 11:10:54 AM »
Well toluene has a methyl group directly attached to the ring and is easily oxidised. So knowing that what happens here?
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Offline Rutherford

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Re: Arenes oxidation with KMnO4
« Reply #4 on: February 09, 2013, 11:15:09 AM »
Durene should be readily oxidized then. Why is that so? Why is the methyl group important?

Offline discodermolide

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Re: Arenes oxidation with KMnO4
« Reply #5 on: February 09, 2013, 11:26:09 AM »
As far as I remember it is a radical type process and requires the hydrogen atom.
see:
http://dspace.nitrkl.ac.in/dspace/bitstream/2080/871/1/oxidation.pdf
« Last Edit: February 09, 2013, 11:49:07 AM by discodermolide »
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Offline Rutherford

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Re: Arenes oxidation with KMnO4
« Reply #6 on: February 09, 2013, 11:30:35 AM »
Thanks for the link, I shall examine it now.

Offline Pranav

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Re: Arenes oxidation with KMnO4
« Reply #7 on: February 09, 2013, 11:44:28 AM »
I do not know the exact mechanism but tertiary groups aren't oxidised by KMnO4.

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