General Organic ChemistryHard

Question

Amongst the following , the most basic compound is :

Options

A.benzylamine
B.aniline
C.acetanilide
D.p-nitroaniline

Solution


      (a)                  (b)               (c)                     (d)
In (b) and (d) ,lp of gp. enters in resonance with benzene ring, hence are not readily available for protonation. In (c) , it enters in resonance with gp.(lp - π bond interaction)
In (a), lp of - can′t enter in resonance and so is available for protonation most easily,i.e., why benzylamine is most basic .

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