Introduction to Preparation of Ethers
Ethers are generally prepared from alcohols or their conjugate bases. One significant procedure, proceeds by an SN2 reaction of an alkoxide nucleophile with an alkyl halide that is known as the Williamson Ether Synthesis. Reactions no.1 and no.2 below are two illustrations of this procedure. When applied to unsymmetrical ether, as in this example, there are two distinct combinations of reactants are possible. Of these one is generally better than the other. Because alkoxide anions are strong bases, the chances of a competing E2 elimination must all the time be considered. Bearing in mind the issues which favor substitution over elimination, a 1º-alkyl halide should be selected like a preferred reactant when possible. So, reaction no.1 gives a cleaner and better yield of benzyl isopropyl ether than does reaction no.2, which generates considerable elimination product.
After the oxymercuration reaction, a second usual ether synthesis, alkoxymercuration is patterned. Reactions no.3 and no.4 are examples of this two-step procedure. Note: the alcohol reactant is employed as the solvent, and a trifluoroacetate mercury (II) salt is employed in preference to the acetate (trifluoroacetate anion is a poorer nucleophile than acetate). The technique of alkoxymercuration is identical to that of oxymercuration, by an initial anti-addition of the mercuric alcohol and species being followed by reductive demercuration.
Acid-catalyzed dehydration of small 1 º-alcohol constitutes a specialized technique of preparing symmetrical ethers. As displayed in the following two equations, the success of this technique depends on the temperature. At 110º to 130 ºC the alcohol's SN2 reaction, conjugate acid leads to an ether product. At higher temperatures (over 150 ºC) E2 elimination happens.
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