33.2 Esters

Learning objectives

33.2.1Preparation of esters• Recall preparation of esters: (a) reaction of alcohols with acyl chlorides using the formation of ethyl ethanoate and phenyl benzoate; as examples

An alcohol reacts with an acyl chloride to form an ester. The alcohol supplies the alkyl-O part and the acyl chloride supplies the acid-derived carbonyl part; HCl is released.

Name the two fragments before writing the product. The reaction is usually rapid at room temperature and is not the reversible equilibrium route used for direct acid/alcohol esterification.

Ethanol + ethanoyl chloride -> ethyl ethanoate + HCl. Phenol + benzoyl chloride -> phenyl benzoate + HCl.

Do not swap the two ester names or write water as the by-product; acyl-chloride esterification produces hydrogen chloride.

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—33.3 Acyl chloridesRead