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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g2233

The compound shown is an ortho-substituted phenol. Select ALL the correct statements.

  1. AThe nitro group acts on the phenoxide only by -I and not by -M.
  2. BIt is steam volatile because of intramolecular hydrogen bonding.
  3. CIt is more acidic than phenol.
  4. DIt has a lower boiling point than its para isomer.

Answer: B, C, D

o-Nitrophenol forms an intramolecular O-H...O hydrogen bond, which makes it steam volatile and lower boiling and less water soluble than the para isomer (intermolecular H-bonding). It is more acidic than phenol (pKa 7.2 vs 10.0) due to -I and -M. The statement that the nitro group has no -M effect is false: at the ortho position it exerts both -I and -M.
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