The compound shown is an aromatic amine. Which one of the structures shown is a stronger base than it in water?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

The compound shown is aniline, whose lone pair is delocalised into the ring. Cyclohexylamine has an alkyl-substituted, localised lone pair and is far more basic. 4-Nitroaniline, diphenylamine and acetanilide all have the nitrogen lone pair withdrawn further, so they are weaker bases than aniline.

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