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JEE Main levelSingle correct optionDifficulty 2 of 3ap117

Phenol is nitrated with dilute at 298 K, giving a mixture of two mononitrophenols that can be separated by steam distillation. The compound that distils over with the steam and the reason are

  1. A4-nitrophenol, because of intramolecular hydrogen bonding
  2. B2-nitrophenol, because of intramolecular hydrogen bonding
  3. C2-nitrophenol, because of extensive intermolecular hydrogen bonding
  4. D4-nitrophenol, because it is the more acidic isomer

Answer: B

In 2-nitrophenol the group is hydrogen bonded to the adjacent group inside the same molecule, so there is little association with water or other molecules and the compound is steam volatile. 4-Nitrophenol forms intermolecular hydrogen bonds, is less volatile, and stays behind.
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