The hydrogen atom of a hydroxyl group is ionizable and can be replaced by other substituents as illustrated in the reactions below. The first reaction shows simple alcohols with sodium (and sodium hydride). The second reaction shows the isotopic exchange that occurs when mixing an alcohol with deuterium oxide (heavy water). This exchange, which is catalyzed by acid or base, is rapid under normal conditions because it is difficult to avoid traces of these catalysts in most experimental systems.
Williamson Ether Synthesis
Alkyl substitution of the hydroxyl group creates ethers. This reaction provides examples of both strong electrophilic substitution (first equation below) and weak electrophilic substitution (second equation). The latter SN2 reaction is known as the Williamson ether synthesis and is generally only used with 1º alkyl halide reactants because the strong alkoxide base leads to E2 elimination with 2º and 3º alkyl halides.
16. Show how you would use the Williamson Ether synthesis to make 1-ethoxy-2-methylpropane from isobutyl alcohol and ethanol.