Which one of the structures shown is a meso compound?

AStructure (A)
BStructure (B)
CStructure (C)
DStructure (D)

Answer: A

A meso compound has two or more stereocentres but is achiral because of an internal symmetry element. Structure (A) is (2R,3S)-tartaric acid: the two halves

- CH (OH) COOH

have opposite configurations, giving a mirror plane, so it is meso. Structure (B) is (2R,3R)-tartaric acid, which is chiral. Structures (C) (butan-2-ol) and (D) (3-chlorobutan-2-ol, (2S,3R)) have no internal symmetry and are chiral.

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