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JEE Main levelSingle correct optionDifficulty 2 of 3g1239

The compound shown is a far weaker base than pyridine mainly because

  1. Aits nitrogen is sp3 hybridised and sterically hindered
  2. Bits nitrogen lone pair is part of the aromatic sextet, so protonation would destroy aromaticity
  3. Cits nitrogen lone pair lies in the ring plane in an sp2 orbital
  4. Dit has fewer carbon atoms than pyridine

Answer: B

The compound shown is pyrrole. Its nitrogen lone pair is part of the aromatic sextet, so protonation on nitrogen would use up that pair and destroy the aromaticity. In pyridine the lone pair lies in the ring plane and is available.
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