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JEE Main levelSingle correct optionDifficulty 2 of 3g1081

Arrange in decreasing order of acidity: (I) 4-nitrophenol, (II) 3,5-dimethyl-4-nitrophenol, (III) phenol.

  1. A
  2. B
  3. C
  4. D

Answer: B

In 3,5-dimethyl-4-nitrophenol the two methyl groups flank the nitro group and twist it out of the ring plane (steric inhibition of resonance), so its -M effect is lost. It is therefore a weaker acid than 4-nitrophenol. It still keeps the -I effect of , so it is a stronger acid than phenol. The order is I > II > III.
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