Chemistry A2 · Carboxylic acids and derivatives. The idea in plain words, the rules to remember, the mistake to avoid and a worked example, written and checked by Mega Lecture.
An ester is made quickly at room temperature when an alcohol or a phenol reacts with an acyl chloride. Hydrogen chloride is the other product. Two examples to know are ethyl ethanoate, from ethanol and ethanoyl chloride, and phenyl benzoate, from phenol and benzoyl chloride.
For phenols this is the method to use. Phenol gives very little ester with a carboxylic acid, because the lone pair on its oxygen is delocalised into the ring, which makes phenol a weak nucleophile. An acyl chloride is reactive enough to work.
To find the ester, join the oxygen of the –OH compound to the C=O carbon of the acyl chloride and remove HCl. The mechanism is addition–elimination.
Mixing up the two halves of the ester. Phenyl ethanoate (phenol + ethanoyl chloride) is CH3COOC6H5; methyl benzoate (methanol + benzoyl chloride) is C6H5COOCH3.
Answer: 5.94 g of phenyl benzoate
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