In 5-membered heterocycles like pyrrole and furan, electrophilic substitution preferentially occurs at the C-2 (alpha) position rather than the C-3 (beta) position. Why?

Question

Prashant Kotian · Accepted Answer

Correct answer: C. Attack at C-2 generates an intermediate that delocalizes the positive charge over three atoms, including the heteroatom (giving full octets). C-3 attack generates an intermediate with only two delocalized resonance structures.

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