MolSynapsequestion bank
MolSynapse / Question bank / Haloalkanes and Haloarenes / SN2 stereochemistry on drawn chiral halides
JEE Main levelSingle correct optionDifficulty 2 of 3hx232

The enantiopure chloride shown reacts with in DMF by SN2 to give the thiol. Give the CIP descriptor of the product.

  1. AR
  2. BS
  3. CA racemic mixture, written (RS)
  4. DNo stereocentre remains

Answer: B

The reactant is (R)-2-chlorobutane. In the thiol the priorities are , the same rank order as , so inversion of geometry flips the label: the product is (S)-butane-2-thiol (RDKit: C[C@H](S)CC is S).
Practice Haloalkanes and Haloarenes More on SN2 stereochemistry on drawn chiral halides

More questions on SN2 stereochemistry on drawn chiral halides