Which is more basic in nature? Benzyl amine or aniline.

What is base?

According to Lewis theory of acids and bases, a base is the one which has the availability of electrons to donate to an acid. Here, we need to find the stronger base among benzyl amine and aniline.

A stronger base will be the one whose electrons are easily available for donation.

Structure of given compound

The structure of aniline and benzyl amine is:

Aniline

In case of aniline, a lone pair of electrons is present on nitrogen atom (N) and this nitrogen atom is attached to a sp² hybridised carbon of the benzene ring. The lone pair of electrons present on nitrogen will involve in resonance with the benzene ring as:So, it is clear that due to resonance present in aniline, lone pair of electrons are delocalised over the benzene ring and hence will be less available for donation.

Benzyl amine

In case of benzyl amine, a lone pair of electrons is again present on nitrogen (N). But here, nitrogen is attached to a sp³ hybridised carbon and not to the benzene ring. Hence, lone pairs of electrons on nitrogen are not involved in any resonance with the benzene ring. Therefore, lone pairs of electrons are localised here on nitrogen atoms and will be readily available for donation.

Thus, benzyl amine is a stronger base than aniline.

Conclusion

Hence, benzyl amine is a stronger base than aniline because the lone pair of electrons on the nitrogen atom in aniline is delocalised over the benzene ring, and are not available for protonation.

Read More: Acidic character order of Haloform

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