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Q.

Which of the following orders is true regarding the basic nature of NH2 group?

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a

o-Toluidine >Aniline< o-Nitroaniline

b

ο-Toluidine >Aniline> ο-Nitroaniline

c

o-Toluidine < Aniline > o-Nitroaniline

d

o-Toluidine < Aniline < o-Nitroaniline

answer is B.

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Detailed Solution

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.

Electron-releasing group increases the availability of lone pair of electrons on nitrogen while electron attracting group decreases this availability.

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