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JEE Main levelOne or more correct optionsDifficulty 2 of 3g2227

The compound shown is a nitrophenol. Select ALL the correct statements about it.

  1. AIts anion is stabilised by the -M effect of the nitro group.
  2. BIts pKa is lower than that of its ortho isomer.
  3. CIt is more acidic than phenol.
  4. DIt is less acidic than its para isomer.

Answer: C, D

m-Nitrophenol has pKa about 8.4, lower than phenol (10.0) because of the -I effect of NO2, so the first statement holds. The para isomer (pKa 7.2) is stronger since -M also operates, so the second holds. At the meta position the nitro group cannot delocalise the phenoxide charge (no -M effect), so the third is false; the ortho isomer (7.2) is also more acidic than meta, so the fourth is false.
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