Williamson ether synthesis

Overview: The general form of the Williamson ether synthesis mechanism is as follows: Placing an alcohol in sodium metal forms the alcoxide plus hydrogen gas (because it forms hydrogen, keep this away from any flame or it will explode!). The alcoxide can then be added to a suitable alkyl halide (primary or secondary) to form the ether via an SN2 mechanism. An example of the Williamson ether synthesis: