The intramolecular Williamson synthesis is 9-7 Synthesis of Ethers:Alcohols and Mineral Acid ethers by both oeeg296mucbenthaoa826eeotento8ec on-nucleophilic acids yields ethers when reacted with Sherhands of Fther Syrhels tehabereepoainmn2ticnofwatarocu听 G1O1-0 snt山is ofa Mised E山ee 2LC CICCHC 0 rsalso form by alcoholysis. 9-8 Reactions of Ethers ss 一一 8 8 The intramolecular Williamson synthesis is stereospecific. Since the Williamson synthesis is a SN2 substitution reaction, an inversion of configuration occurs at the carbon bearing the leaving group. The leaving group must be on the opposite side of the molecule from the attacking nucleophile in order for the reaction to occur. 9-7 Synthesis of Ethers: Alcohols and Mineral Acid Alcohols give ethers by both SN2 and SN1 mechanisms. Strong nucleophilic acids (HBr, HI) yield haloalkanes when reacted with alcohols. Strong non-nucleophilic acids yields ethers when reacted with alcohols. At higher temperatures, an E2 elimination of water occurs with the subsequent production of alkenes. Secondary and tertiary alcohols form ethers through an SN1 reaction with a second molecule of the alcohol trapping the carbocation. The E1 pathway becomes dominate at higher temperatures. Mixed ethers containing one tertiary and one primary or secondary alcohol can be prepared in the presence of dilute acid. The tertiary carbocation is trapped by the less hindered alcohol. Ethers also form by alcoholysis. This occurs by simply dissolving a tertiary or secondary haloalkane in an alcohol and waiting until the SN1 process is complete. 9-8 Reactions of Ethers Ethers are usually inert, however, they do react slowly with oxygen to form hydroperoxides and peroxides which can decompose explosively