Which of the following orders is true regarding the basic nature of −NH2 group?
A
o−Toluidine>Aniline>o−Nitroaniline
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B
o−Toluidine<Aniline>o−Nitroaniline
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C
o−Toluidine<Aniline<o−Nitroaniline
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D
o−Toluidine>Aniline<o−Nitroaniline
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Solution
The correct option is Bo−Toluidine<Aniline>o−Nitroaniline The correct order of basic strength of aromatic amines is o−Toluidine<Aniline>o−Nitroaniline.
Aniline is more basic than ortho nitro aniline because the presence of electron withdrawing nitro group decreases the ease with which N can donate a lonepair of electrons.
o-Toluidine is less basic than aniline because whenever a substituent is present in the ortho position, it decreases its basicity.