MolSynapsequestion bank
MolSynapse / Question bank / Haloalkanes and Haloarenes / SN2 stereochemistry on drawn chiral halides
JEE Main levelSingle correct optionDifficulty 2 of 3hx225

The primary bromide shown reacts with aqueous by SN2. Which structure is the substitution product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: B

Substitution occurs at the CH2Br carbon, which is not the stereocentre. The stereocentre (C-2 of 1-bromo-2-methylbutane) is untouched, so its spatial arrangement is retained and the product is the corresponding 2-methylbutan-1-ol with the same geometry. The enantiomeric alcohol would require a bond to the stereocentre to break; the tertiary alcohol would need a rearranged cation; the alkene is an elimination product.
Practice Haloalkanes and Haloarenes More on SN2 stereochemistry on drawn chiral halides

More questions on SN2 stereochemistry on drawn chiral halides