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JEE Main levelSingle correct optionDifficulty 2 of 3ap097

Phenol is nitrated with dilute at 298 K, giving a mixture of two mononitrophenols. When the mixture is steam distilled, the compound that distils over is

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

Answer: B

In 2-nitrophenol the OH forms an intramolecular hydrogen bond with the adjacent , so the molecules do not associate and the compound is steam volatile. In 4-nitrophenol the molecules are linked by intermolecular hydrogen bonds, which lowers volatility. The ortho isomer therefore distils with steam.
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