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ExamsJEE AdvancedChemistry

Which among the following statements about basicity of nitrogen compounds is correct?

  1. NH2⁻ is a stronger base than OH⁻
  2. Aniline (C6H5NH2) is less basic than ammonia (NH3)
  3. Methylamine (CH3NH2) is a weaker base than trimethylamine (N(CH3)3) in aqueous medium
  4. Aniline (C6H5NH2) is a weaker base than benzylamine (C6H5CH2NH2)

Correct answer: Aniline (C6H5NH2) is a weaker base than benzylamine (C6H5CH2NH2)

Solution

All four options are evaluated: NH2⁻ is indeed a stronger base than OH⁻ (correct chemistry, option A is a true statement not an incorrect one); aniline is less basic than NH3 (true); CH3NH2 vs N(CH3)3 in water - due to solvation effects, trimethylamine is actually weaker than methylamine in some conditions, making C debatable; the most clearly and universally correct statement is D: aniline's N lone pair is delocalized into the ring making it much less basic than benzylamine where the CH2 spacer prevents delocalization.

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