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Question

Account for the following:
$$p{K}_{b}$$ of aniline is more than that of methylamine.


Solution

In aniline due to resonance, the lone pair of electrons on the $$N-$$atom are delocalized over the benzene ring. Due to this, electron density on the nitrogen decreases. On the other hand, in $${CH}_{3}-{NH}_{2}$$, +I effect of $${CH}_{3}$$ increases the electron density on the $$N-$$atom. Consequently, aniline is a weaker base than methylamine and hence its $$p{K}_{b}$$ value is higher than that of methylamine.

Chemistry

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