Which reagents convert an acid chloride to a carboxylic acid?

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Multiple Choice

Which reagents convert an acid chloride to a carboxylic acid?

Hydrolysis of an acyl chloride by water is the direct way to form a carboxylic acid. The carbonyl carbon in the acid chloride is highly susceptible to nucleophilic attack by water, and the chloride is a good leaving group. After water adds and chloride leaves, you get the carboxylic acid along with HCl as a byproduct. In equation form: R-COCl + H2O → R-COOH + HCl. Other options don’t achieve this transformation by themselves: converting a carboxylic acid to its chloride uses SOCl2, not the reverse; and simply adding a base to a carboxylic acid won’t convert an acid chloride into a carboxylic acid. So the reagent that directly gives a carboxylic acid from an acid chloride is water.

Hydrolysis of an acyl chloride by water is the direct way to form a carboxylic acid. The carbonyl carbon in the acid chloride is highly susceptible to nucleophilic attack by water, and the chloride is a good leaving group. After water adds and chloride leaves, you get the carboxylic acid along with HCl as a byproduct. In equation form: R-COCl + H2O → R-COOH + HCl. Other options don’t achieve this transformation by themselves: converting a carboxylic acid to its chloride uses SOCl2, not the reverse; and simply adding a base to a carboxylic acid won’t convert an acid chloride into a carboxylic acid. So the reagent that directly gives a carboxylic acid from an acid chloride is water.

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