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14: Ethers, Epoxides and Thioethers

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  • After reading this chapter and completing ALL the exercises, a student can be able to

    • predict relative boiling points and solubilities of ethers (refer to section 15.1)

    • explain how ether solvents stabilize electrophilic reagents (refer to section 15.1)

    • determine the structures of ethers from their spectra, and explain their characteristic absorptions and fragmentations (refer to section 15.2)

    • devise efficient laboratory synthesis of ethers and epoxides, including:

           a)    Williamson ether synthesis (refer to section 15.3)

           b)    alkoximercuration-demercuration (refer to section 15.4)

           c)    peroxyacid epoxidation (refer to Chapter 9 section 12)

           d)    base-promoted cyclization of halohydrins (refer to section 15.7)

    • predict the products or reactions of ethers and epoxides, including:

           a)    acidic cleavage of ethers (refer to section 15.5)

           b)    opening of epoxides (refer to section 15.8)

           c)    reactions of epoxides with organometallic reagents (refer to section 15.10)

    • explain how Crown ethers solvate metal cations (refer to section 15.10)

    • explain the reaction of epoxy monomers to form the adhesive resin (refer to section 15.11)

    • describe the structure and reactive of sulfides (refer to section 15.12)

    • use your knowledge of chemical reactivity to propose mechanisms and products for similar reactions you have never seen before (chapters to date)

    • propose multiple-step syntheses using all of the reactions studied through this chapter (chapters to date)

    Please note: IUPAC nomenclature and important common names of alcohols were explained in Chapter 3.

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