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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ap105

Which statements about nitrophenols are correct?

  1. A4-Nitrophenol is more acidic than phenol because the nitro group stabilises the phenoxide ion by both and effects.
  2. B4-Nitrophenol is not steam volatile because its molecules are associated through intermolecular hydrogen bonding.
  3. C3-Nitrophenol is more acidic than phenol, the nitro group acting only through its effect.
  4. D2-Nitrophenol has a higher melting point than 4-nitrophenol because of intramolecular hydrogen bonding.

Answer: A, B, C

In the para isomer, the negative charge on oxygen is delocalised onto the nitro group, and in the meta isomer only the inductive effect operates, but both are more acidic than phenol. The para isomer is associated by intermolecular hydrogen bonding and is not steam volatile. Intramolecular hydrogen bonding in the ortho isomer reduces association, so its melting point (about 318 K) is lower, not higher, than that of the para isomer (about 387 K).
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