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Topic: light bromination of m-methylbenzyl alcohol - which direction?  (Read 1467 times)

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Offline txxplc110

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light bromination of m-methylbenzyl alcohol - which direction?
« on: January 07, 2024, 03:09:16 PM »
Hi, I am wondering which groups will be substituted during bromination under light irradiation (UV). Is it possible for a -CH2 group to be substituted as well as a methyl group? Will one bromine atom be substituted, or will all hydrogen atoms in those positions be exchanged?
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Offline Hunter2

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Re: light bromination of m-methylbenzyl alcohol - which direction?
« Reply #1 on: January 07, 2024, 03:37:21 PM »
Probably you get m-Tribrominemethyl-benzoic acid bromide.

CBr3-C6H4-CO-Br
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Offline rolnor

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Re: light bromination of m-methylbenzyl alcohol - which direction?
« Reply #2 on: January 08, 2024, 07:53:45 AM »
I think its hard to make a tribromomethyl, its stericaly crowded. And I dont see why you would get a acyl bromide?
I think you get m-bromomethylbenzylbromide in a mixture with m-bromomethylbenzyl alcohol. Some of the hydroxymethyl will be converted to a bromomethyl by the hydrogen bromide released in the bromination of the methyl group.
« Last Edit: January 08, 2024, 10:12:42 AM by rolnor »
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Offline Hunter2

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Re: light bromination of m-methylbenzyl alcohol - which direction?
« Reply #3 on: January 08, 2024, 11:23:06 AM »
I thought bromine is an oxidiser and  react with R-CH2OH to R--CHBrOH + HBr
This will release another HBr because of Erlenmeyer rule to R-CHO, I am not sure the aldehyde can converted  to acid Bromide.
For the methyl group probably you are right and get only 1 bromomethyl BrCH2-R'.
« Last Edit: January 08, 2024, 12:33:47 PM by Hunter2 »
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