Chapter 143 of 2363 min read
Basicity of amines
Why this is asked: In water, aliphatic amine basicity doesn't rise monotonically with substitution — the usual order is 2° > 1° > 3° > NH₃, because a 3° amine's extra alkyl groups add electron density but also add steric hindrance that weakens solvation of the resulting ammonium ion, and that loss outweighs the electronic gain. Aniline is far less basic than ammonia for a different reason: its nitrogen lone pair delocalises into the ring by resonance, and a ring nitro group weakens it further still.
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