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JEE Main levelSingle correct optionDifficulty 2 of 3g2196

4-Nitrophenol is much more soluble in water than 2-nitrophenol. This is because

  1. A4-nitrophenol is non-polar
  2. B2-nitrophenol has no hydroxyl group
  3. C2-nitrophenol has an intramolecular hydrogen bond, while 4-nitrophenol hydrogen-bonds with water
  4. D2-nitrophenol is more acidic and ionises completely

Answer: C

In 2-nitrophenol the and the adjacent are close enough to form an intramolecular hydrogen bond, so the hydroxyl is unavailable for water. In 4-nitrophenol this is impossible, and the and groups hydrogen-bond with water, which raises solubility.
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