I keep getting “Basicity of amines” questions wrong in Amines & Biomolecules. What's the trap?
thinking aniline is more basic than an alkylamine.
The usual trap: thinking aniline is more basic than an alkylamine. How to avoid it: aniline's lone pair is tied up in the ring → weaker base. Go back to the definition — amines are basic because the nitrogen lone pair can accept a proton; aliphatic amines are more basic than ammonia, aniline is less.
Key point
Basicity of amines
Common mistake
thinking aniline is more basic than an alkylamine.
Memory tip
aniline's lone pair is tied up in the ring → weaker base.
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