Topic: Arenes oxidation with KMnO4 (Read 3961 times)

Rutherford · « **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?

discodermolide · « **Reply #1 on:** February 09, 2013, 10:58:43 AM »

What do you get when you treat toluene with KMnO₄?

Rutherford · « **Reply #2 on:** February 09, 2013, 11:05:28 AM »

Benzoic acid. How to apply this here?

discodermolide · « **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?

Rutherford · « **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?

discodermolide · « **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

Rutherford · « **Reply #6 on:** February 09, 2013, 11:30:35 AM »

Thanks for the link, I shall examine it now.

Pranav · « **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.