Which of the following is a meso compound?

A(2R,3R)-2,3-dichlorobutane
B(2R,3S)-2-bromo-3-chlorobutane
C(2R,3S)-2,3-dichlorobutane
D(2S,3S)-2,3-dichlorobutane

Answer: C

A meso compound has stereocentres but an internal mirror plane, which requires identical substituents on the two centres and opposite descriptors. Only 2,3-dichlorobutane has identical centres, and the (2R,3S) form has opposite descriptors. The (R,R) and (S,S) forms are chiral, and 2-bromo-3-chlorobutane has two different centres, so no internal mirror plane is possible.

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