Reaction of an acid chloride with water yields which product?

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Multiple Choice

Reaction of an acid chloride with water yields which product?

Acid chlorides hydrolyze readily in water. Water acts as a nucleophile, attacking the carbonyl carbon of the acid chloride and displacing the chloride as Cl−. This forms a tetrahedral intermediate that, after proton transfers, collapses to the carboxylic acid, with HCl as a byproduct. So the product is a carboxylic acid (RCOOH). This differs from reactions with alcohols, which replace Cl with OR to give an ester, or with amines, which give an amide. The key is that water hydrolyzes the acid chloride to the carboxylic acid.

Acid chlorides hydrolyze readily in water. Water acts as a nucleophile, attacking the carbonyl carbon of the acid chloride and displacing the chloride as Cl−. This forms a tetrahedral intermediate that, after proton transfers, collapses to the carboxylic acid, with HCl as a byproduct. So the product is a carboxylic acid (RCOOH).

This differs from reactions with alcohols, which replace Cl with OR to give an ester, or with amines, which give an amide. The key is that water hydrolyzes the acid chloride to the carboxylic acid.

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