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Question

Decreasing order of basicity of the three isomers of nitro aniline is:

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

The correct option is C m-nitroaniline > p-nitroaniline > o-nitroaniline
Nitro group is an electron-withdrawing group. It mainly withdraws electrons from the ortho and para positions by -M effect. Therefore para isomer is less basic than meta isomer.

Ortho substituted anilines are generally weaker bases than aniline irrespective of the electron releasing or electron- withdrawing nature of the substituent. This is due to ortho effect.

Hence decreasing order of basicity of the isomers of nitroaniline: m - nitroaniline > p - nitroaniline > o - nitroaniline
Hence, (c) is the correct option.

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