Consider the stereoisomers of 2,3-dibromobutane. Which of the following statements accurately descri — Haloalkanes and Haloarenes Chemistry Question
Question
Consider the stereoisomers of 2,3-dibromobutane. Which of the following statements accurately describe their stereochemical properties?
💡 Solution & Explanation
2,3-dibromobutane has two similar chiral centers. A) True. The (2R, 3S) configuration is identical to the (2S, 3R) configuration because the molecule has an internal plane of symmetry. This internal compensation makes the meso form achiral and optically inactive. B) True. Diastereomers are stereoisomers that are not mirror images. The meso form is not a mirror image of either the pure (2R, 3R) [d-isomer] or the (2S, 3S) [l-isomer], hence they are diastereomeric. C) False. A meso compound is a distinct, pure substance with its own physical properties (melting point, boiling point, etc.). A racemic mixture is a 1:1 mixture of two enantiomers, which interacts differently in the solid state and thus generally has a different melting point compared to the pure meso compound. D) True. The three stereoisomers are the (2R, 3R) enantiomer, the (2S, 3S) enantiomer, and the meso compound.