MolSynapsequestion bank
MolSynapse / Question bank / Haloalkanes and Haloarenes / Stereochemical outcomes of substitution
JEE Main levelSingle correct optionDifficulty 2 of 3hx045

(S)-1-Bromo-2-methylbutane reacts with in DMSO by at the carbon. The product 3-methylpentanenitrile is

  1. A(S)-3-methylpentanenitrile, because the stereocentre is not the reacting carbon
  2. Bracemic 3-methylpentanenitrile
  3. C(R)-3-methylpentanenitrile, because always inverts the label
  4. Dan achiral product

Answer: A

The reacting carbon () is not a stereocentre, so the bonds to the stereocentre are untouched and its spatial arrangement is retained. Priorities at the stereocentre: in the substrate and in the product (at the second sphere, (N,N,N) beats (H,H,H)). The order is unchanged, so the label remains (S).
Practice Haloalkanes and Haloarenes More on Stereochemical outcomes of substitution

More questions on Stereochemical outcomes of substitution