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JEE Main levelSingle correct optionDifficulty 2 of 3g3091

Pyrrole is heated with chloroform and sodium ethoxide (Ciamician-Dennstedt rearrangement). The main product is

  1. A3-Chloropyridine
  2. B2-Chloropyridine
  3. C2-Chloropyrrole
  4. DPyridine-3-carbaldehyde

Answer: A

Dichlorocarbene adds across the C2=C3 bond of pyrrole to give a dichlorocyclopropane fused to the ring. This opens with loss of and ring expansion by one atom, giving the six-membered pyridine ring. The remaining chlorine ends up on the new ring carbon, which lies at position 3 of the pyridine.
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