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Topic: C8H8O2 to C8H6O2Br2  (Read 2803 times)

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Offline owlpower

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C8H8O2 to C8H6O2Br2
« on: July 13, 2016, 06:51:07 AM »
When 4,methylbenzoic acid reacts with Br2(aq), why doesn't C8H8O2Br2 form? I thought the positions of CH3 (2,4 directing) and COOH (1,3 directing) will support Bromination.

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Offline sjb

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Re: C8H8O2 to C8H6O2Br2
« Reply #1 on: July 13, 2016, 07:49:35 AM »
Quote from: owlpower on July 13, 2016, 06:51:07 AM
When 4-methylbenzoic acid reacts with Br2(aq), why doesn't C8H8O2Br2 form? I thought the positions of CH3 (2,4 directing) and COOH (1,3 directing) will support Bromination.

Other reactions may compete. Are either methyl or carboxylic acid strong activators?
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Offline owlpower

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Re: C8H8O2 to C8H6O2Br2
« Reply #2 on: July 13, 2016, 08:43:20 AM »
CH3 is an activator (electron donating) and COOH is not (electron withdrawing). Thus they will support bromination due to their relative positions, correct?

What other reactions could possibly occur? I can only think of free radical sub for CH3.
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Offline AWK

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Re: C8H8O2 to C8H6O2Br2
« Reply #3 on: July 13, 2016, 01:54:20 PM »
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Offline Enthalpy

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Re: C8H8O2 to C8H6O2Br2
« Reply #4 on: July 17, 2016, 02:44:00 PM »
The first message doesn't mention any catalyst. Does bromine react at the aromatic ring then ? Or rather at the methyl? Thanks!
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