Reactions of Acyl Chlorides with Alcohols

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Page ID: 3796

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This page gives you the facts and a simple, uncluttered mechanism for the nucleophilic addition / elimination reaction between acyl chlorides (acid chlorides) and alcohols.

Ethanoyl chloride is taken as a typical acyl chloride. Any other acyl chloride will behave in the same way. Simply replace the \(CH_3\) group in what follows by anything else you want. Similarly, ethanol is taken as a typical alcohol. If you are interested in another alcohol, you can replace the \(CH_3CH_2\) group by any other alkyl group.

The reaction between ethanoyl chloride and ethanol

Ethanoyl chloride reacts instantly with cold ethanol. There is a very exothermic reaction in which a steamy acidic gas is given off (hydrogen chloride). Ethyl ethanoate (an ester) is formed.

The mechanism

The first stage (the addition stage of the reaction) involves a nucleophilic attack on the fairly positive carbon atom by one of the lone pairs on the oxygen of an ethanol molecule.