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Topic: Why are brominations so commonly done in glacial acetic acid?  (Read 1407 times)

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Offline Zensation

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Why are brominations so commonly done in glacial acetic acid?
« on: February 18, 2014, 11:52:57 PM »
Almost every bromination I have seen whether using elemental bromide or N-Bromosuccinimide take place in glacial acetic acid.

Is there a reason for this? Solubility reasons? Why not some other acids?

Offline clarkstill

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Re: Why are brominations so commonly done in glacial acetic acid?
« Reply #1 on: February 19, 2014, 02:31:02 AM »
I guess it's polar and protic so good at stabilizing the bromonium ion, but not a good enough nucleophile to compete with Br-.  Aqueous acids are out, as water would attack the bromonium ion.  I'm sure it would also work fine in neat stronger acids (TFA, TfOH etc.) but AcOH is a little milder.

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