Illustrated Glossary of Organic Chemistry

Stereospecific: A reaction in which the stereochemistry of the reactants controls the outcome of the reaction. In general, one stereoisomer of certain reactant produces one stereoisomer of a certain product, whereas a different stereoisomer of the same reactant produces a different stereoisomer of the same product.

The addition of molecular bromine to 2-butene is stereospecific. The addition of molecular bromine to (E)-2-butene gives meso-2,3-dibromobutane...



  ...whereas addition of molecular bromine to (Z)-2-butene gives a racemic mixture of (2S,3S)-2,3-dibromobutane plus (2R,3R)-2,3-dibromobutane: