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JEE Main levelSingle correct optionDifficulty 2 of 3g2073

Arrange in decreasing order of basic strength in aqueous solution (approximate pKaH: benzylamine 9.3, aniline 4.6, acetanilide about $- 1$ ): benzylamine, aniline, acetanilide.

Aacetanilide > aniline > benzylamine
Baniline > benzylamine > acetanilide
Cbenzylamine > acetanilide > aniline
Dbenzylamine > aniline > acetanilide

Answer: D

Benzylamine has a localised lone pair (pKaH 9.3). Aniline's lone pair is delocalised into the ring (4.6). In acetanilide,

C X_{6} H X_{5} NHCOCH X_{3}

, the lone pair is delocalised onto the carbonyl as well and is a very weak base.

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