Four anilines are shown beside the options (the drawn compound is aniline). Which structure is the weakest base?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

A para nitro group withdraws the nitrogen lone pair by -I and -M, so p-nitroaniline (pKaH about 1.0) is the weakest. p-Chloroaniline is 4.0, aniline 4.6, p-toluidine 5.1 and p-anisidine 5.3.

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