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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g1163

Which of the following statements are correct?

  1. AIn pyridine the lone pair on nitrogen lies in the plane of the ring and is not part of the aromatic sextet.
  2. BPyrrole is a stronger base than pyridine.
  3. CPyrrole N-H is much more acidic than the N-H of pyrrolidine because the pyrrolide anion is aromatic.
  4. DIn furan one lone pair of oxygen is part of the aromatic sextet.

Answer: A, C, D

Statements 1, 3 and 4 are true: pyridine's sp2 lone pair is outside the pi system; pyrrolide keeps a 6 pi electron sextet after deprotonation; furan's oxygen supplies 2 pi electrons from one lone pair. Statement 2 is false because pyrrole's lone pair is tied up in the sextet, so it is a far weaker base than pyridine.
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