Home Wikituition Browse all terms Categories
Random term
Organic Chemistry

Nucleophilic Substitution

A reaction in which a nucleophile replaces a leaving group attached to a saturated carbon.

Formula / equation Nu⁻ + R–X → R–Nu + X⁻
Unit Dimensionless

In depth

The reaction is the principal route for converting haloalkanes into alcohols, ethers, amines and nitriles. It proceeds by either the concerted SN2 pathway or the stepwise SN1 pathway, with substrate structure, nucleophile strength and solvent determining which dominates.

Examples in the real world

Bromoethane with aqueous hydroxide giving ethanol; with cyanide giving propanenitrile.