402ETHERS, EPOXIDES, AND SULFIDES16.3An ether can function only as a proton acceptor in a hydrogen bond, but an alcohol can be either aproton acceptor or a donor. The only hydrogen bond possible between an ether and an alcohol istherefore the one shown:16.4The compound is 1,4-dioxane; it has a six-membered ring and two oxygens separated by CH2—CH2units.16.5Protonation of the carbon–carbon double bond leads to the more stable carbocation.Methanol acts as a nucleophile to capture tert-butyl cation.Deprotonation of the alkyloxonium ion leads to formation of tert-butyl methyl ether.16.6Both alkyl groups in benzyl ethyl ether are primary, thus either may come from the alkyl halide in aWilliamson ether synthesis. The two routes to benzyl ethyl ether are16.7(b)A primary carbon and a secondary carbon are attached to the ether oxygen. The secondary car-bon can only be derived from the alkoxide, because secondary alkyl halides cannot be used in
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