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Question

The correct order of basic strength of given aniline is:

A
o - nitroaniline > p - nitroaniline > m - nitroaniline
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B
m - nitroaniline > p - nitroaniline > o - nitroaniline
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C
m - nitroaniline > o - nitroaniline > p - nitroaniline
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D
o - nitroaniline > m - nitroaniline > p - nitroaniline
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Solution

The correct option is D m - nitroaniline > p - nitroaniline > o - nitroaniline
The pKa values of m - nitroaniline, p - nitroaniline and o - nitroaniline isomers are 2.5, 1.0 and -0.3 respectively.

Due to the presence of the electron-withdrawing nitro group, the delocalization of the lone pair of electron is improved. This effect is observed in para and ortho position.

In the ortho position, a very close inductive effect of the nitro group is also observed. (ortho effect) Hence, o - nitroaniline is less basic than p - nitroaniline.

In m - nitroaniline, only the inductive effect is present.

The decreasing order of basicity is m - nitroaniline > p - nitroaniline > o - nitroaniline.

Option B is correct.

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