The Student Room Group

Oxidation of Alkyl substituent attached to benzene

Can somebody tell the product when this compound is oxidised?
benzoic acid
Reply 2
Original post by BobbJo
benzoic acid


If we have methyl benzene or any alkyl benzene or secondary alkyl attached to benzene as above, oxidation is possible.... ?

If we have a tertiary alkyl attached, e.g in tert-butylbenzene, oxidation not possible????
Original post by googie3
If we have methyl benzene or any alkyl benzene or secondary alkyl attached to benzene as above, oxidation is possible.... ?

If we have a tertiary alkyl attached, e.g in tert-butylbenzene, oxidation not possible????

yes and yes
Reply 4
Thank you...

One more thing, why no reaction between HBr and phenol?
Original post by BobbJo
yes and yes
Original post by googie3
Thank you...

One more thing, why no reaction between HBr and phenol?

Br- nucleophile repelled by the ring electrons
Addition reaction would break the very stable ring structure
Reply 6
Original post by BobbJo
Br- nucleophile repelled by the ring electrons
Addition reaction would break the very stable ring structure


so this means substituting OH of phenol is hard...?
Reply 7
Original post by googie3
so this means substituting OH of phenol is hard...?

is there any example where OH of phenol gets substituted?
Original post by googie3
so this means substituting OH of phenol is hard...?


Yes. C-O bond is strengthened by overlap of lone pair of electrons on O over the ring.

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