Acid Derivatives - Nucleophilic substitution

There entry is about another nucleophilic substitution mechanism. It should not be surprising that there are more than one type of nucleophilic substitution mechanism. This is because the reaction, nucleophilic substitution, is a very broad classification of reactions.

However, the nucleophilic substitution mechanism of acid derivatives (e.g. acid chlorides, esters and amides) is different from the nucleophilic substitution of alkyl halides.

In this entry, I will highlight the mechanism for the reaction between acid chloride and water. This reaction is a hydrolysis reaction and it occurs faster than the hydrolysis reaction of alkyl halides. This is because the electron deficient carbon of the acid chloride is more exposed than that of alkyl halide.

The following picture is the illustration of the nucleophilic substitution reaction between acid chloride and water (hydrolysis reaction). A video to describe how to draw (or describe) the mechanism is found below.

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Article written by Kwok YL 2009.}

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