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When stereoisomeric starting materials are used in a reaction, a stereospecific reaction results in a product from one reactant that is a stereoisomer of the product from the other.
While a stereoselective reaction chooses products from among those produced by the same, non-specific mechanism acting on a particular reactant, a stereospecific mechanism specifies the stereochemical outcome of a given reactant. A stereospecific mechanism, given a single, stereoisomeric ally pure starting material, will produce 100% of a specific stereoisomer (or no reaction), yet stereochemical integrity can readily be lost due to competing processes that produce distinct stereochemical results. Even if only one mechanism is at work on an isomerically pure starting material, a stereoselective process will typically yield numerous products. The term "stereospecific reaction" is ambiguous because the word "reaction" itself can refer to either the end product of a reactant mixture that may proceed through multiple competing, specific and non-specific mechanisms, or it can refer to a single-mechanism transformation (such as the Diels-Alder reaction), which could be stereospecific. The phrase stereospecific reaction is frequently used incorrectly to refer to a highly stereoselective reaction in the latter sense. Chiral synthesis is based on a mix of stereoselective and stereospecific transformations, where the optical activity of a chemical molecule is conserved. Stereospecific transformations are used to interconvert existing stereocenters.
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