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I want to know about the reaction mechanism of haloform reaction in acidic condition. I am following a persons doctoral thesis where he used acid medium haloform reaction but unfortunately he has not given any references.

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    $\begingroup$ Do you have a link to the thesis? $\endgroup$
    – user15489
    Jun 1 '15 at 10:14
  • $\begingroup$ Please give necessary references, it took me for a surprise and I'm interested to know more. $\endgroup$ Aug 17 '18 at 3:25
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In the book by Clayden et al. you can find a very nice description of the mechanism of the halogenation of enols and the haloform reaction on pp. 533-536. Especially on p. 536 the authors give the mechanistic details of the acid catalysed halogenation of enols and some reasons why multiple halogenation steps on the same carbon atom (as happens in the haloform reaction) occur easily under base catalysis but do usually not occur under acidic conditions. Since I lack the time to write it up myself (and since the authors already did a marvelous job at describing it) I simply post the relevant passage here:

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