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Which of the following compounds will show significant intermolecular hydrogen bonding? (JEE Mains 2021) (a) o-nitrophenol (b) p-hydroxyacetanilide (HO-C6H4-NHCOCH3) (c) a sterically hindered phenol with bulky tert-butyl groups

1. (b) only
2. (c) only
3. (a) and (b) only
4. (a), (b) and (c)

Correct answer: (b) only

Solution

o-Nitrophenol: the -OH and ortho -NO2 are geometrically close and form a strong intramolecular H-bond, so it cannot participate significantly in intermolecular H-bonding (this is why it has a lower boiling point than p-nitrophenol). The sterically hindered phenol: bulky tert-butyl groups around the -OH prevent close approach of other molecules, blocking intermolecular H-bonding. p-Hydroxyacetanilide: para arrangement prevents intramolecular H-bonding; both the -OH and -NHCO- groups form intermolecular H-bonds readily.

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