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JEE Main levelOne or more correct optionsDifficulty 2 of 3nc228

Select all the correct statements about the compound shown.

  1. AThe nitrogen lone pair lies in the plane of the ring and is not part of the aromatic sextet
  2. BIt is a weaker base than piperidine
  3. CIt is a stronger base than pyrrole
  4. DThe nitrogen lone pair contributes two electrons to the six pi electrons of the ring

Answer: A, B, C

The compound shown is pyridine. Its lone pair is in an sp2 orbital in the ring plane and the ring pi sextet comes from the carbons and the pyridine-type nitrogen's p electron, so the lone pair is free to accept a proton. Pyridine (conjugate acid pKa about 5) is weaker than the sp3 amine piperidine (about 11) but far stronger than pyrrole, whose lone pair is part of the sextet.
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