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Question
Account for the following.
pKb of aniline is more than that of methylamine.
Solution
In aniline, the lone pair of electrons on the N-atom is delocalized over the benzene ring. As a result electron density on the nitrogen decreases. In contrast in CH3NH2, the +I effect of CH3 increases the electron density on the N-atom. Therefore, aniline is a weaker base than methylamine and hence its pKb value is more than that of methyl amine.
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\[\begin{array}{cc}
\phantom{.}\ce{CH3}\\
|\phantom{..}\\
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\phantom{.}|\phantom{.....}|\phantom{........}\\
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\end{array}\]
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