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13.4     Arrange the following:

                 (iii) In increasing order of basic strength:

                 (a) Aniline, p-nitroaniline and p-toluidine

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Structure of the following compounds-

In p-toluidine, the methyl group increases the electron density at the N atom (+I effect of methyl), so it is more basic than aniline. In p-nitroaniline, the nitro group is an electron withdrawing group, so it decreases the electron density from N atom, so it is less basic than aniline.

 

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