Alcohol in reaction with active metal sodium gives sodium alkoxide. sodium alkoxide on reaction with an alkyl halide gives ether. It is known as Williamson’s ether synthesis helps to synthesize aliphatic, aromatic, symmetrical, unsymmetrical ethers.
ROH + Na = RONa + ½ H2
RONa + R – X = R – O – R + NaX
RONa + R’ – X = R – O – R’ + Nax
CH3CH2OH + Na = CH3CH2ONa + ½ H2
CH3CH2ONa + CH3 – Br = CH3CH2 – O – CH3 + NaBr