Arrange in decreasing order of basicity in water: (I) cyclohexanamine, (II) aniline, (III) N-phenylethanamide (acetanilide).

A $III > II > I$
B $I > II > III$
C $I > III > II$
D $II > I > III$

Answer: B

In cyclohexanamine the nitrogen lone pair is localised and +I-enriched. In aniline it is delocalised into the ring. In acetanilide it is delocalised towards the carbonyl group as well as the ring, so it is the least available. The order is I > II > III.

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Arrange in decreasing order of basicity in water: (I) cyclohexanamine, (II) aniline, (III) N-phenylethanamide (acetanilide).

Answer: B

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