Chapter 18 - SN1 is based on forming the more stable...

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Sheet1 Page 1 Chapter 18: Ethers and Epoxides Synthesis of Ethers: symmetrical: sulfuric acid catalyzed, SN2 mechanism Williamson: use less hindered portion as alkyl halide, more hindered as alkoxide -use NaH to form an alkoxide ion and add alkyl halide -may use Ag2O, no need to preform the alkoxide intermediate SN2 reaction (forms more stable product than E2) Alkoxymercuration: basically oxymercuration using (CF3CO2)2Hg as the reagent, adds on -oR rather than -OH will form a racemic mixture Acidic Cleavage: HBr or HI can be used to cleave ethers Primary and Secondary: SN2, Br attacks less hindered site
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Unformatted text preview: SN1 is based on forming the more stable carbocation Epoxides: Synthesis: treatment of an alkene with a peroxyacid (RCOOOH) such as M-CPBA (concerted) intramolecular williamson synthesis: 1.trans halohydrin formation 2.treatment with pase to deprotonate alcohol SN2 mechanism Ring Opening: Acid: SN1 or SN2 SN2 nucleophilic attack occurs at less substituted site SN1 attack occurs at more substituted site, 100% inversion due to ion pair effect Base: SN2 or E2, Grignard E2 occurs rarely, because it yields a less stable product Sheet1 Page 2 Thiols and Sulfides...
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This note was uploaded on 04/26/2009 for the course CHEM 227 taught by Professor Santander during the Fall '08 term at Texas A&M.

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Chapter 18 - SN1 is based on forming the more stable...

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