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Topic: Bromination with catalyst  (Read 3515 times)

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Offline kelaklub

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Bromination with catalyst
« on: May 15, 2006, 06:02:44 PM »
In the following problem the answer is stated as choice A.

Is this because the amino group is more electron withdrawing than the methyl (alkyl) group, and therefore activates the ring for a ortho or para attack? Am I wording my thoughts correctly?

I know the only other choice that might make sense for this reaction is choice B, but that is in meta to the amino group. Any help would be appreciated. Thanks.

Offline Will

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Re: Bromination with catalyst
« Reply #1 on: May 15, 2006, 06:47:09 PM »
You're on the right lines, but both the functional groups are electron repelling (electron 'releasing'), but the -NH2 group is more electron releasing since the -CH3 has a very weak positive inductive effect, and the -NH2 has a lone pair of electrons which can overlap with the delocalised ring of electrons in benzene.
Since the -NH2 is more strongly ortho/para dircting than the -CH3 the bromination will occur at the carbon next to the amine substituted carbon.

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