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Question

Account for the following:
pKb of aniline is more than that of methylamine.

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Solution

In aniline due to resonance, the lone pair of electrons on the Natom are delocalized over the benzene ring. Due to this, electron density on the nitrogen decreases. On the other hand, in CH3NH2, +I effect of CH3 increases the electron density on the Natom. Consequently, aniline is a weaker base than methylamine and hence its pKb value is higher than that of methylamine.

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