Question

Arrange the following in the increasing order of basicity.

• A. Pyrrole
• B. Pyridine
• C. Aniline
• D. Benzylamine

Answer 1

Pyrrole is least basic because lone pair is involved in aromaticity. The lone pair of electrons in aniline is involved in resonance. $N$ in pyridine is $s{p}^2$ hybridized whereas for benzylamine it is $s{p}^3$ hybridized.
So, the order for basicity follows as:
Pyrrole<aniline<pyridine<benzylamine