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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2145

4-Methylphenol (p-cresol) is treated with dilute at low temperature. The major mononitration product is

  1. A4-methyl-2,6-dinitrophenol
  2. B4-(nitromethyl)phenol
  3. C4-methyl-2-nitrophenol
  4. D4-methyl-3-nitrophenol

Answer: C

The para position is already occupied by the methyl group. The hydroxyl group is the stronger activator and directs ortho to itself, so the nitro group enters ortho to . Dilute acid at low temperature stops at mononitration.
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