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The nitrogen lone pair in the compound shown is used in the aromatic sextet. What does this imply for its basicity compared with pyridine?

  1. AIt is a much weaker base because protonation would destroy the aromatic sextet
  2. BIt is a stronger base because the N-H bond is polar
  3. CIt is equally basic because both are aromatic heterocycles
  4. DIt is a stronger base because nitrogen is sp3 hybridised

Answer: A

The compound shown is pyrrole. Its nitrogen lone pair is part of the six pi electrons, so protonation on nitrogen would break aromaticity; the conjugate acid has a very low pKa. In pyridine the lone pair lies in the plane in an sp2 orbital and is free for protonation.
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