MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / SN2 mechanism, rate, stereochemistry, steric effects
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3098

Select the correct statements about SN2 reactions of cyclic halides.

  1. A1-Bromobicyclo[2.2.1]heptane is inert to SN2 because the backside of the C-Br carbon lies inside the cage and is shielded by the skeleton.
  2. BBromocyclopropane is far less reactive than bromocyclopentane because the SN2 transition state needs an sp2-like carbon with wide angles, which increases the angle strain in the three-membered ring.
  3. CIn a conformationally locked bromocyclohexane, an axial bromine is displaced faster than an otherwise identical equatorial bromine, because the nucleophile then approaches from the less hindered equatorial direction.
  4. D1-Bromo-1-methylcyclohexane reacts with in acetone mainly by SN2 to give 1-iodo-1-methylcyclohexane.

Answer: A, B, C

The first three statements are standard consequences of the geometry of the SN2 transition state: angle strain for the cyclopropyl ring, impossible inversion at a bridgehead, and less hindered backside approach to an axial leaving group. The last is false because the carbon is tertiary and cannot be reached by a nucleophile in SN2.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on SN2 mechanism, rate, stereochemistry, steric effects

More questions on SN2 mechanism, rate, stereochemistry, steric effects