JEE Advanced · 2014 · 25 May 2014 · Paper 2 · Chapter_pending

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The major product in the following reaction is
  1. (A)(see structure)
  2. (B)(see structure)
  3. (C)(see structure)
  4. (D)(see structure)
    ✓ Correct

Answer: (D)

Solution

This is an acid-catalyzed intramolecular cyclization reaction. The alkene undergoes protonation followed by nucleophilic attack by the hydroxyl group to form a five-membered cyclic ether (tetrahydrofuran derivative). The tertiary carbocation intermediate is stabilized, and the ring closure is favored due to the formation of a stable five-membered ring. The product is the substituted tetrahydrofuran shown in option (D).

JEE Advanced · 2014 · 25 May 2014 · Paper 2 · Single correct option

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