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Question
Arrange the following:
In increasing order of basic strength:
Aniline, p-nitroaniline and p-toluidine
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Solution
In p-toluidine, the presence of an electron-donating −CH3 group increases the electron density on the N-atom. Thus, p-toluidine is more basic than aniline.
On the other hand, the presence of electron-withdrawing −NO2 group decreases the electron density over the N-atom in p-nitroaniline. Thus, p-nitroaniline is less basic than aniline.
Hence, the increasing order of the basic strengths of the given compounds is as follows:
p-Nitroaniline < Aniline < p-Toluidine
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