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JEE Main levelOne or more correct optionsDifficulty 2 of 3g2086

In which of the following is the nitrogen lone pair a part of the aromatic pi sextet (so that it is not the site of protonation)?

  1. AN-1 of pyrrole
  2. BN-1 (the N-H) of 1H-imidazole
  3. CN-3 (the N without H) of 1H-imidazole
  4. DN of pyridine

Answer: A, B

In pyrrole and at the N-H nitrogen of imidazole, the lone pair is donated into the ring to give six pi electrons. In pyridine and at N-3 of imidazole the nitrogen has a double bond in the ring, contributing one p electron, and the lone pair is in an in-plane sp orbital available for protonation.
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