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Basicity of AminesAmines

Which is a stronger base: Benzenamine (Aniline) or Phenylmethanamine (Benzylamine)? Explain the structural reason.

Expert Answer

Benzylamine is stronger. Reason: In Aniline, the lone pair on Nitrogen is involved in resonance with the benzene ring, making it less available for protonation. In Benzylamine ( PhCH2NH2Ph-CH_2-NH_2 ), the CH2-CH_2- group isolates the Nitrogen from the ring, preventing resonance, so it behaves like a typical aliphatic amine.

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