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JEE Advanced levelSingle correct optionDifficulty 3 of 3g1271

The compound shown is compared with 4-nitrophenol and with phenol. Which order of acidity (decreasing from left to right) is correct?

  1. Acompound shown > 4-nitrophenol > phenol
  2. B4-nitrophenol > phenol > compound shown
  3. Ccompound shown > phenol > 4-nitrophenol
  4. D4-nitrophenol > compound shown > phenol

Answer: D

In the compound shown, steric inhibition of resonance twists the nitro group out of plane, so it is a weaker acid than 4-nitrophenol. It is still a stronger acid than phenol, as the nitro group still withdraws by induction and some conjugation remains. Order: 4-nitrophenol (7.2) > compound shown (8.3) > phenol (10.0).
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