What would be the expected product or products of (R)-3-chlorobut-1-ene with HBr?

Question

Quizplus · Accepted Answer

(R)-3-chlorobut-1-ene is a chiral compound, therefore any reaction with an achiral reagent such as HBr will result in a diastereomeric mixture. The product(s) will have two stereocenters: the original chiral center at the 3 position and a new stereocenter at the 2 position where the bromine was added. The (2R,3R) and (2S,3R) stereoisomers will be formed in approximately equal amounts, leading to a diastereomeric mixture as the major product. Option A and B represent individual stereoisomers, which cannot be formed separately in this reaction. Option D represents a meso compound, which cannot be formed from a chiral starting material and an achiral reagent.

What Would Be the Expected Product or Products of (R)-3-Chlorobut-1-Ene