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Dolbier HW Solutions 308 - 402 ETHERS EPOXIDES AND SULFIDES...

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402 ETHERS, EPOXIDES, AND SULFIDES 16.3 An ether can function only as a proton acceptor in a hydrogen bond, but an alcohol can be either a proton acceptor or a donor. The only hydrogen bond possible between an ether and an alcohol is therefore the one shown: 16.4 The compound is 1,4-dioxane; it has a six-membered ring and two oxygens separated by CH 2 CH 2 units. 16.5 Protonation 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. 16.6 Both alkyl groups in benzyl ethyl ether are primary, thus either may come from the alkyl halide in a Williamson ether synthesis. The two routes to benzyl ethyl ether are 16.7 ( 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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