Which of the following compounds is most basic?
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Answer
(2) [figure]
Solution
In aniline, p-nitroaniline and acetanilide the lone pair on N is delocalised into the benzene ring (and in acetanilide also onto the C=O group); the -NO2 group withdraws electrons further.
In benzylamine (C6H5CH2NH2) the -NH2 group is attached to an sp3 carbon, so its lone pair is not delocalised – it behaves like an alkylamine.
As per NCERT, pKb of benzylamine = 4.70 while that of aniline = 9.38.
∴ Basic strength: benzylamine > aniline > p-nitroaniline, acetanilide
Answer: (2)