MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / Neighbouring group participation
NEET levelSingle correct optionDifficulty 1 of 3o3119

In neighbouring group participation, the nucleophile attacks the carbon twice in succession, each time from the side opposite to the group being displaced. The net stereochemical result at that carbon is

  1. Acomplete racemisation
  2. Bformation of a meso compound in every case
  3. Cretention of configuration
  4. Dinversion of configuration

Answer: C

Each backside attack inverts the carbon. Two successive inversions restore the original spatial arrangement, so the overall result is retention of configuration.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on Neighbouring group participation

More questions on Neighbouring group participation