In the following monobromination reaction, the number of possible chiral products is
(see structure)
(1.0 mole) (enantiomerically pure)
Answer: 5
Solution
The substrate is (2S)-butane (enantiomerically pure 2-butanol or similar chiral starting material). Monobromination can occur at different positions. Bromination at C-1 gives a chiral product (new stereocenter). Bromination at C-2 (where the existing chiral center is) can give two diastereomers. Bromination at C-3 gives another chiral product (new stereocenter). Bromination at C-4 gives a chiral product. Considering all possible positions and the stereochemistry, there are 5 distinct chiral products (excluding achiral meso forms).
JEE Advanced · 2016 · 22 May 2016 · Paper 1 · Integer answer
