The correct order of base strength of the following amines is

The correct order of base strength of the following amines is

  1. A

    o – nitroaniline > p – nitroaniline > m – nitroaniline

  2. B

    m – nitroaniline > p – nitroaniline > o – nitroaniline

  3. C

    m – nitroaniline > o – nitroaniline > p – nitroaniline

  4. D

    o – nitroaniline > m – nitroaniline > p – nitroaniline

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    Solution:

    • 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.
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