The Williamson ether synthesis is a chemical reaction involving an alcohol and a halide compound that forms an ether. The alkoxide ion from the alcohol component reacts with a primary alkyl halide, resulting in the generation of an ether compound.
The mechanism of the Williamson ether synthesis follows an SN2 reaction, which is a mechanism that involves a simultaneous breaking and formation of bonds. The synthesis of esters in this particular reaction breaks off the non-alkyl halide section and fuses the alkoxide ion to the halide. An example of a reaction using the Williamson ether synthesis mechanism is the production of diethyl ether from sodium ethoxide and chloroethane.
Alkoxide ions are very reactive, which creates a need to prepare the substance just moments before its mixture to the alkyl halide. Some industries and laboratories reduce the rate of reaction by using protic and apolar solvents such as N,N-dimethylformamide and acetonitrile.
Considered one of the most common ways of producing ethers, the Williamson ether synthesis is used in both laboratory and industrial settings.
The organic reaction was named after Alexander Williamson, who developed the mechanism in 1850. His discovery paved the way for the confirmation of the ether structure. In his experiments, Williamson experimented with sulfuric acid and alcohol to produce an ether.