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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Rutherford on February 09, 2013, 10:53:29 AM

Title: Arenes oxidation with KMnO4
Post by: 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?

Title: Re: Arenes oxidation with KMnO4
Post by: discodermolide on February 09, 2013, 10:58:43 AM

What do you get when you treat toluene with KMnO₄?

Title: Re: Arenes oxidation with KMnO4
Post by: Rutherford on February 09, 2013, 11:05:28 AM

Benzoic acid. How to apply this here?

Title: Re: Arenes oxidation with KMnO4
Post by: discodermolide 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?

Title: Re: Arenes oxidation with KMnO4
Post by: Rutherford on February 09, 2013, 11:15:09 AM

Durene should be readily oxidized then. Why is that so? Why is the methyl group important?

Title: Re: Arenes oxidation with KMnO4
Post by: discodermolide 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 (http://dspace.nitrkl.ac.in/dspace/bitstream/2080/871/1/oxidation.pdf)

Title: Re: Arenes oxidation with KMnO4
Post by: Rutherford on February 09, 2013, 11:30:35 AM

Thanks for the link, I shall examine it now.

Title: Re: Arenes oxidation with KMnO4
Post by: Pranav on February 09, 2013, 11:44:28 AM

I do not know the exact mechanism but tertiary groups aren't oxidised by KMnO4.