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JEE Advanced levelSingle correct optionDifficulty 3 of 3cb213

Which comparison of o-nitrophenol and p-nitrophenol is correct?

  1. Ao-Nitrophenol has the higher boiling point and the higher solubility in water
  2. Bp-Nitrophenol has the higher boiling point but the lower solubility in water
  3. Cp-Nitrophenol has the higher boiling point and the higher solubility in water
  4. Do-Nitrophenol has the lower boiling point but the higher solubility in water

Answer: C

o-Nitrophenol forms an intramolecular hydrogen bond, so its OH is not available to associate with other molecules or with water. It is therefore more volatile and less soluble in water. p-Nitrophenol forms intermolecular hydrogen bonds with itself (raising the boiling point) and with water (raising solubility).
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