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JEE Advanced levelSingle correct optionDifficulty 3 of 3g2093

4-Nitroaniline (pKaH 1.0) is a weaker base than 3-nitroaniline (pKaH 2.5) mainly because

  1. Athe nitro group is a donor at the para position
  2. Bthe amino group in 4-nitroaniline is sp hybridised
  3. Cthe nitro group at the para position withdraws electrons from the amino N by the effect (in addition to ), while at the meta position only the effect operates
  4. Dthe meta isomer forms stronger hydrogen bonds with the solvent through the nitro group

Answer: C

A group conjugates with the amino group only when it is at the ortho or para position (resonance form with positive charge on N and negative charge on the nitro O atoms). At meta only the weaker effect operates, so 3-nitroaniline is the stronger base.
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