Which of the following is more basic than aniline?

1. benzylamine
2. diphenylamine
3. triphenylamine
4. p-nitroaniline

Solution

Benzyl amine is more basic than aniline because the benzyl group is an electron-donating group on account of the + I effect. So, it is capable of increasing the electron density of $\mathrm{N}$ of the $-\mathrm{NH}_2$ group. Thus, because of the higher electron density, the rate of donation of a free pair of electrons is increased, i.e., the basic character is higher. Phenyl and nitro groups are electron attractive groups, so they are able to decrease the electron density of $\mathrm{N}$ of $-\mathrm{NH}_2$ group. Hence, they are less basic than aniline. NOTE Benzylamine has localised lone pair therefore it is more basic.

Asked in: MHT CET Full Test 10

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