MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms IV: Elimination / Substitution vs elimination competition
JEE Advanced levelSingle correct optionDifficulty 3 of 3o4165

(R)-2-Bromobutane reacts with in DMF by a single SN2 step. The major product and its configuration are

  1. A(S)-2-azidobutane
  2. B(R)-2-azidobutane
  3. Cracemic 2-azidobutane
  4. Dbut-1-ene

Answer: A

Azide is a good nucleophile and weak base in a polar aprotic solvent, so SN2 dominates with backside attack and inversion. In both the bromide and the azide the substituent has top priority, followed by ethyl, methyl, H, so the descriptor changes from R to S.
Practice Organic Reaction Mechanisms IV: Elimination More on Substitution vs elimination competition

More questions on Substitution vs elimination competition