SN2
The SN2 reaction is a type of reaction mechanism that is common in organic chemistry. In this mechanism, one bond is broken and one bond is formed synchronously, i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism. Since two reacting species are involved in the slow (rate-determining) step, this leads to the term substitution nucleophilic (bi-molecular) or SN2, the other major kind is SN1. Many other more specialized mechanisms describe substitution reactions.
The reaction type is so common that it has other names, e.g. "bimolecular nucleophilic substitution", or, among inorganic chemists, "associative substitution" or "interchange mechanism".
The reaction most often occurs at an aliphatic sp3 carbon center with an electronegative, stable leaving group attached to it (often denoted X), which is frequently a halide atom. The breaking of the C–X bond and the formation of the new bond (often denoted C–Y or C–Nu) occur simultaneously through a transition state in which a carbon under nucleophilic attack is pentacoordinate, and approximately sp2hybridised. The nucleophile attacks the carbon at 180° to the leaving group, since this provides the best overlap between the nucleophile's lone pair and the C–X σ* antibonding orbital. The leaving group is then pushed off the opposite side and the product is formed with inversion of the tetrahedral geometry at the central atom.
If the substrate under nucleophilic attack is chiral, this often leads to inversion of configuration (stereochemistry), called a Walden inversion.
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