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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g1109

Which of the following phenols are stronger acids than phenol?

  1. A3-nitrophenol
  2. B4-chlorophenol
  3. C4-aminophenol
  4. D4-nitrophenol

Answer: A, B, D

The nitro groups withdraw electrons (-I at the meta position, -I and -M at the para position) and stabilise the phenoxide ion. Chlorine at the para position is net electron withdrawing, because -I outweighs +M. The group at the para position is a strong +M donor and makes the phenol a weaker acid (pKa 10.3 against 9.99).
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