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JEE Main levelSingle correct optionDifficulty 2 of 3ap119

The values are: phenol 9.95, 3-nitrophenol 8.36, 4-nitrophenol 7.15. The best explanation of why 4-nitrophenol is more acidic than 3-nitrophenol is that

  1. Athe nitro group exerts a stronger effect at the meta position than at the para position
  2. B4-nitrophenol forms intramolecular hydrogen bonds that release the proton more readily
  3. Cthe nitro group at the para position donates electrons by effect
  4. Din the 4-nitrophenoxide ion the negative charge is delocalised onto the nitro group by resonance, which cannot happen from the meta position

Answer: D

A nitro group para to the oxygen can accept the negative charge of the phenoxide through resonance () in addition to its effect. At the meta position only the inductive effect operates, so the acidity increase (9.95 to 8.36) is smaller than for para (9.95 to 7.15).
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