Warming a phenol with a carboxylic acid gives an ester only with difficulty, whereas an alcohol reacts readily. This is because
Correct answer: B. the phenolic oxygen donates its lone pair into the ring, making it a poorer nucleophile
- A. phenols contain no hydroxyl group
- B. the phenolic oxygen donates its lone pair into the ring, making it a poorer nucleophile
- C. phenols are stronger bases than alcohols
- D. esters cannot contain a benzene ring
Explanation
Delocalisation of the oxygen lone pair into the aromatic system, the very effect that makes phenol acidic, leaves that oxygen less available to attack the carbonyl carbon of an acid. Phenyl esters are therefore prepared using more reactive acyl chlorides or anhydrides instead. The same delocalisation also shortens and strengthens the carbon to oxygen bond in phenol.
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About Phenols
Phenols contain a hydroxyl group directly bonded to an aromatic ring, making them more acidic than alcohols because the phenoxide ion is resonance-stabilised. Reactions include ionisation with bases, electrophilic substitution, bromination, nitration and oxidation, with attention to the difference between phenols and aliphatic alcohols.
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535 free Alcohols and Phenols MCQs from Chemistry, each with the correct answer and an explanation. Unlimited attempts, no account needed.
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