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Amines as Bases

The basicity ...

Question

The basicity of aniline is weaker in comparison to that of methylamine due to:

A

hyperconjugative effect of

M e -

group

M e N H_{2}

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B

resonance effect of phenyl group in aniline

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C

lower molecular weight of methyl amine compared to that of aniline

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D

resonance effect of

- N H_{2}

group in

M e N H_{2}

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Solution

The correct option is A resonance effect of phenyl group in aniline
The lone pair of electrons, present in N-atom in aniline involve in ring resonance. So it is less basic than methyl amine.

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Q. The activating effect of

- N H C O C H_{3}

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Q. Assertion :p-Anisidine is weaker base than aniline. Reason:

- O C H_{3}

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p K b

of aniline is more than that of methylamine. Reason: In aniline, the lone pair of electrons on the

N

atom is delocalized over the benzene ring. As a result, the electron density of nitrogen decreases. In contrast, in

{C H}_{3} {N H}_{2} (+ I)

{C H}_{3}

increases the electron density on the

N

atom. Therefore, aniline is a weaker base than methylamine and hence its

p K_{b}

value is higher than that of methylamine.

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