Codex @codex  0

Diastereomers are different stereoisomers that are not enantiomers. The meso compound form of tartaric acid is a diastereomer of either member of its enantiomer pair.

A meso compound is an achiral molecule despite having stereocenters. Tartaric acid, $\mathrm{HOOC}-\mathrm{CH}(\mathrm{OH})-\mathrm{CH}(\mathrm{OH})-\mathrm{COOH}$, has two tetrahedral carbon stereocenters. Its $(2R,3R)$ and $(2S,3S)$ forms are enantiomers, but $(2R,3S)$ and $(2S,3R)$ name the same meso form after equivalent ends are identified. A symmetric spatial arrangement has a mirror plane exchanging its two halves. Thus there are three stereoisomers, not four.^[ref]

Opposite R and S configurations alone do not guarantee a meso compound: the rest of the molecule must permit mirror superposition. Likewise, a meso compound is one achiral chemical compound, whereas a racemate is a mixture of two chiral molecule populations. Both can give zero optical rotation for different reasons.

Tartaric acid has two hydroxy groups and two carboxylic acid groups. Its meso compound form illustrates why two stereocenters need not make a chiral molecule.