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The reactions of ethanoyl chloride
Reaction with water
This reaction is responsible for the fact that acyl chlorides fume in moist air. Water in the air reacts with the acyl chloride producing hydrogen chloride gas. This highly soluble gas causes small droplets of water to form in the air and these are seen as fumes. The other product is the parent carboxylic acid:
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Water is acting as a nucleophile.
Reaction with ethanol
Acyl chlorides react with alcohols to produce an ester and hydrogen chloride gas. The alcohol molecule is the nucleophile here, as it has a lone pair of electrons on the oxygen. It is this oxygen atom which is attracted to, and becomes attached to, the positively charged carbon atom in the acyl chloride:
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Reaction with ammonia
Ammonia is the nucleophile in this reaction, with the lone pair on the nitrogen being attracted to the positive carbon atom in the acyl chloride. It forms a bond to this atom leaving an amide (ethanamide) and hydrogen chloride gas:
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