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2,3-Dihydrobenzofuran is heated with excess concentrated HI. The major product formed in this reaction is:

Options

  1. A2-(2-Iodophenyl)ethanol
  2. B1-Iodo-2-(2-iodoethyl)benzene
  3. C2-(2-Iodoethyl)phenol
  4. DNo reaction occurs, 2,3-dihydrobenzofuran is recovered

Correct answer

C. 2-(2-Iodoethyl)phenol

Step-by-step solution

2,3-Dihydrobenzofuran is a bicyclic compound containing a cyclic ether fused to a benzene ring. The ether oxygen is bonded to an sp^2 hybridized aromatic carbon (aryl-oxygen bond) and an sp^3 hybridized aliphatic carbon (alkyl-oxygen bond). When treated with concentrated HI and heated, ether cleavage occurs. The aryl-oxygen bond has partial double bond character due to the delocalization of the oxygen's lone pair into the aromatic ring, making it strong and resistant to cleavage. Therefore, the cleavage exclusively

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