When reacting an acyl chloride with methanol, the chloride leaving group leaves, but later acts as a base? why? Isn't chloride only a nucleophile?

1 Answer
Dec 30, 2017

It is hard to see from where you are coming....

Explanation:

An acyl halide is a reactive species, and typically WE ADD a non-nucleophilic base to remove the #HCl# generated.

#RC(=O)Cl +HOR' stackrel(Et_3N)rarr RC(=O)OR' + Et_3N*HCl#

And, here, triethylamine hydrochloride precipitates from solution to give the ESTER in solution....such reactions exclude water given that water could act on the acyl halide....

#RC(=O)Cl +H_2Orarr RC(=O)OH + HCluarr#