Why are acyl chlorides so reactive?

1 Answer
anor277
Jul 21, 2016

Because they contain (i) an unsaturated carbon centre, and (ii) a potential leaving group in the chloride ion.

Explanation:

The business end of an acyl halide, #RC(=O)X (X=Cl, Br)#, contains a reactive #sp_2# hybridized carbon, and a potential leaving group in the chloride ion. If I ever wanted to perform an esterification reaction, I would always boil up my starting carboxylic acid with thionyl chloride, to give the acid chloride, which would easily react with added alcohol or amine in the presence of a non-nucleophilic base.

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