Which of the following orders is correct regarding basicity of indicated molecules?

Which of the following orders is correct regarding basicity of indicated molecules?

  1. A

    N,N-Dimethyltoluidine >p-toluidine > aniline >p-nitroaniline 

  2. B

     Aniline >N,N-dimethyl- p-toluidine >p-toluidine > aniline 

  3. C

    p-Toluidine >N,N-dimethyl- p-toluidine > aniline >p-nitroaniline 

  4. D

    N,N-Dimethyltoluidine > aniline >p-toluidine >p-nitroaniline 

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    Solution:

    Aniline is a weaker base. It is a Lewis base, i.e. the lone pair present on nitrogen can be given to the Lewis acids. The electron-releasing group present at the para position increases the electron density on nitrogen and thus makes it more basic. For example, para-toluidine is more basic than aniline. On the other hand, the presence of electron-withdrawing group decreases the electron density on nitrogen and hence makes it less basic. For example, p-nitroaniline is less basic than aniline

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