Q.2,3-Dibromobutane has two stereocentres. State which combination of configurations, , or , gives a meso (achiral) compound, and explain why the other two are a pair of enantiomers.
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Start your 14-day free trial to unlock the full solution →2,3-Dibromobutane's two stereocentres, C2 and C3, carry an identical set of substituents as each other (each is attached to , , a methyl group, and the other stereocentre), which is what makes a meso possibility available here. In the (equivalently written , 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 and combinations, both stereocentres share the same handedness, there is no such internal mirror plane …
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