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Which of the following is the most basic?

  1. Apyrrole
  2. Bacetamide
  3. C
  4. Dpyridine

Answer: D

Pyrrole nitrogen lone pair is part of the aromatic sextet and acetamide lone pair is delocalised onto C=O, so both are very weakly basic. Pyridine has its lone pair in an sp2 orbital in the plane of the ring and is more basic than aniline (pKb about 8.8 against 9.4).
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