Meso compound 2026-10-14
A meso compound is an achiral molecule despite having stereocenters. Tartaric acid, , has two tetrahedral carbon stereocenters. Its and forms are enantiomers, but and 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]
5.7 Meso Compounds. McMurry, Organic Chemistry, §5.7, Figure 5.12: meso-tartaric acid and its symmetry plane
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.
Racemate 2026-10-14
A racemate contains the same amount of substance of each member of an enantiomer pair. Their equal and opposite contributions cancel in ordinary solution polarimetry under identical conditions. Zero net optical rotation therefore does not establish achirality of the individual molecules.[ref]
5.8 Racemic Mixtures and the Resolution of Enantiomers. McMurry, Organic Chemistry, §5.8: equal enantiomer populations and cancelling optical rotations