MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms IV: Elimination / E2 mechanism and anti-periplanar requirement
JEE Advanced levelSingle correct optionDifficulty 3 of 3o4032

2,2-Dimethylcyclohexanol is treated with in pyridine. The major alkene is formed by

  1. AE2 anti elimination without rearrangement, giving 3,3-dimethylcyclohexene
  2. BE1 with a methyl shift, giving 1,2-dimethylcyclohexene
  3. CE2 anti elimination without rearrangement, giving 1,2-dimethylcyclohexene
  4. DE1 without rearrangement, giving 1,6-dimethylcyclohexene

Answer: A

With /pyridine the OH is converted to , a good leaving group, and pyridine acts as the base in an E2 anti elimination. No carbocation forms, so no methyl shift occurs; the only beta-hydrogens are on C-6, so 3,3-dimethylcyclohexene results (unlike with hot ).
Practice Organic Reaction Mechanisms IV: Elimination More on E2 mechanism and anti-periplanar requirement
Previous questionNext question

More questions on E2 mechanism and anti-periplanar requirement