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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: shalikadm on June 02, 2012, 02:39:31 AM

Title: About oxidation of alkylbenzene ?
Post by: shalikadm on June 02, 2012, 02:39:31 AM

We have taught that there must be a directly bound H atom to the C atom which is bound to the benzene ring to oxidize alkylbezene(benzene ring-CH₃) with strong oxidants (H⁺/KHmO₄ heat )unlike non-alkylebenzene(benzene ring-C≡CH)

1.Do we need such thing (a directly bound H atom to the C atom which is bound to the benzene ring) to oxidize alkylbezene with alkaline KMnO₄ to get benzoate ion ?

2.It says that we can oxidize toluene with soft oxidants (MnO₂) to get benzaldehyde.Can we get benzaldehyde from any  alkyl or non-alkyl benzene with soft oxidants ?

Title: Re: About oxidation of alkylbenzene ?
Post by: discodermolide on June 02, 2012, 02:48:29 AM

Quote from: shalikadm on June 02, 2012, 02:39:31 AM

We have taught that there must be a directly bound H atom to the C atom which is bound to the benzene ring to oxidize alkylbezene(benzene ring-CH₃) with strong oxidants (H⁺/KHmO₄ heat )unlike non-alkylebenzene(benzene ring-C≡CH)

1.Do we need such thing (a directly bound H atom to the C atom which is bound to the benzene ring) to oxidize alkylbezene with alkaline KMnO₄ to get benzoate ion ?

2.It says that we can oxidize toluene with soft oxidants (MnO₂) to get benzaldehyde.Can we get benzaldehyde from any  alkyl or non-alkyl benzene with soft oxidants ?

1. Yes you require a CH species on the carbon attached to the aromatic ring.
2. The benzylic carbon atom will be the one which is oxidized, all other things being equal. MnO₂ should do this and stop without further oxidation to the acid.

Title: Re: About oxidation of alkylbenzene ?
Post by: shalikadm on June 02, 2012, 02:53:46 AM

thanks for the quick reply

Title: Re: About oxidation of alkylbenzene ?
Post by: canadapolar on June 04, 2012, 04:23:58 AM

Thank you, this was helpful for me, too.