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Exercise · Q22

Q.2,3-Dibromobutane has two stereocentres. State which combination of configurations, (2R,3R)(2R,3R), (2S,3S)(2S,3S) or (2R,3S)(2R,3S), gives a meso (achiral) compound, and explain why the other two are a pair of enantiomers.

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2,3-Dibromobutane's two stereocentres, C2 and C3, carry an identical set of substituents as each other (each is attached to Br\text{Br}, H\text{H}, a methyl group, and the other stereocentre), which is what makes a meso possibility available here. In the (2R,3S)(2R,3S) (equivalently written (2S,3R)(2S,3R), since the molecule is symmetric) combination, one half of the molecule is the mirror image of the other half, related by an internal mirror plane running between C2 and C3 -- the molecule is therefore superimposable on its own mirror image and is achiral, despite containing two stereocentres; this is the meso compound. In the (2R,3R)(2R,3R) and (2S,3S)(2S,3S) combinations, both stereocentres share the same handedness, there is no such internal mirror plane …

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