Stereospecific reaction

A reaction in which the stereochemistry of the reactants determines the stereochemistry of the products. Different stereoisomeric reactants therefore produce different stereoisomeric products.

Stereospecificity: A relationship in which different stereoisomeric reactants yield different stereoisomeric products through a reaction. This broader property describes the defining reactant-to-product relationship.
Stereochemistry: The study of the three-dimensional arrangement of atoms in molecules and its effects on chemical behavior. Stereospecific reactions depend on three-dimensional molecular arrangements.
Walden inversion: Inversion of configuration at a tetrahedral stereocenter during a chemical reaction. It is the characteristic stereochemical result of an SN2 substitution.
Stereoselectivity: The preferential formation of one stereoisomer over other possible stereoisomers in a reaction. A reaction may be stereoselective without mapping each reactant stereoisomer to a distinct product.
SN2 reaction: A nucleophilic substitution reaction that occurs in one step, with bond formation and bond breaking happening together. Backside attack inverts configuration at the reacting stereocenter.
Stereoisomerism: Isomerism between molecules with the same connectivity but different spatial arrangements of atoms. The reactants and products can differ as stereoisomers without changing connectivity.
Anti-periplanar geometry: An arrangement in which two bonds lie in the same plane and point in opposite directions. This alignment enables the stereospecific elimination characteristic of many E2 reactions.
Stereoconvergent reaction: A reaction in which different stereoisomeric reactants yield the same stereoisomeric product. It contrasts with stereospecific mapping, where reactant stereochemistry changes the product stereochemistry.
E2 reaction: A concerted elimination in which a base removes a proton as a leaving group departs. The required antiperiplanar arrangement makes substrate geometry determine alkene geometry.
Enantiomer: One of a pair of stereoisomers that are nonsuperimposable mirror images. Enantiomeric reactants can follow pathways that produce different stereoisomeric products.

Linked from 9 pages