Stereospecificity

[1][2][3] In contrast, stereoselectivity[1][2] is the property of a reactant mixture where a non-stereospecific mechanism allows for the formation of multiple products, but where one (or a subset) of the products is favored by factors, such as steric access, that are independent of the mechanism.

Given a single, stereoisomerically pure starting material, a stereospecific mechanism will give 100% of a particular stereoisomer (or no reaction), although loss of stereochemical integrity can easily occur through competing mechanisms with different stereochemical outcomes.

A stereoselective process will normally give multiple products even if only one mechanism is operating on an isomerically pure starting material.

The choice of mechanism adopted by a particular reactant combination depends on other factors (steric access to the reaction centre in the substrate, nucleophile, solvent, temperature).

[4] This addition remains stereospecific even if the starting alkene is not isomerically pure, as the products' stereochemistry will match the reactants'.