MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry II: Acids and Bases / Basic strength of amines and heterocycles
NEET levelSingle correct optionDifficulty 1 of 3g2060

Pyrrole is practically non-basic because

  1. Athe lone pair on nitrogen is part of the aromatic sextet and protonation on N would destroy aromaticity
  2. Bit has no nitrogen atom
  3. Cits nitrogen is sp hybridised and sterically hindered
  4. Dit contains a carbonyl group that withdraws the lone pair

Answer: A

Pyrrole needs the N lone pair to complete its six pi electrons (4 from the two C=C plus 2 from N). Using it for bonding to would break aromaticity, so pyrrole is an extremely weak base.
Practice General Organic Chemistry II: Acids and Bases More on Basic strength of amines and heterocycles

More questions on Basic strength of amines and heterocycles