MolSynapsequestion bank

MolSynapse / Question bank / Amines and Aromatic Nitrogen Compounds / Basicity of amines

JEE Main levelSingle correct optionDifficulty 2 of 3nc026

Pyridine is a much stronger base than pyrrole because:

Apyridine is nonaromatic
Bthe nitrogen lone pair of pyrrole is part of the aromatic sextet, while that of pyridine lies in an sp2 orbital in the ring plane
Cpyrrole has no nitrogen atom
Dthe nitrogen of pyridine is sp3 hybridised

Answer: B

In pyrrole the lone pair is delocalised in the pi system and protonation would destroy aromaticity, so pyrrole is only very weakly basic. In pyridine the lone pair is in an sp2 orbital perpendicular to the pi cloud, free for protonation without loss of aromaticity.

Practice Amines and Aromatic Nitrogen Compounds More on Basicity of amines

Previous questionNext question

More questions on Basicity of amines

Given that, in aqueous solution, the order of basicity of methylamines is (CH3)2NH > CH3NH2 > (CH3)3N > NH3, which pair correctly explains w... JEE Main level
Among the following, the weakest base is: JEE Main level
The correct order of decreasing basicity is: JEE Main level
Which of the following are weaker bases than ammonia in water? JEE Main level
Which statements are correct? JEE Main level
Guanidine, (H2N)2C=NH, is a very strong organic base because: JEE Main level