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18.13: Summary of Reactions

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    459838
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    18 • Summary of Reactions 18 • Summary of Reactions
    1. Synthesis of ethers (Section 18.2)
      1. Williamson ether synthesis
        An alkoxide ion reacts with an alkyl halide (R dash C H 2 X) to yield an ether (R O C H 2 R dash) and a halide ion.
    • Alkoxymercuration/demercuration
      Tetramethylethylene reacts with alcohol and mercury(2) acetate, then sodium borohydride in an oxymercuration-demercuration reaction, forming an ether product.
    • Reactions of ethers
      1. Cleavage by HBr or HI (Section 18.3)
        The reaction of R O R' with H X and H 2 O produces R X and R dash O H.
    • Acid-catalyzed epoxide opening (Section 18.5)
      Ethylene oxide reacts with hydronium ion to forms ethylene glycol, also known as 1,2-ethanediol. The reaction is called an acid-catalyzed epoxide opening reaction.
      Ethylene oxide in the presence of hydrogen bromide yields 2-bromoethanol via the opening of the epoxide ring.
    • Base-catalyzed epoxide opening (Section 18.5)
      Ethylene oxide reacts with a strong base (R O minus) and an alcohol (R O H), to form an ether compound. Stereochemistry is specified.
      A Grignard reagent (R M g X) reacts with ethylene oxide in ether, then with hydronium ion to produce alcohol. R C H 2 C H 2 O H.
    • Synthesis of thiols (Section 18.7)
      R C H 2 B r reacts with dithiooxamide in the first step and water and sodium hydroxide in the second step to yield R C H 2 S H.
    • Oxidation of thiols to disulfides (Section 18.7)
      Two thiols react with iodine and water to yield a disulfide compound (R S - S R).
    • Synthesis of sulfides (Section 18.7)
      A thiolate anion reacts with an alkyl bromide to yield an alkyl thioether compound along with bromide ion.
    • Oxidation of sulfides to sulfoxides and sulfones (Section 18.7)
      Sulfide reacts with hydrogen peroxide to form a product in which sulfur is double-bonded to an oxygen atom and singly bonded with R and R dash groups.
      Sulfoxide reacts with R C O 3 H to form a product in which sulfur is double-bonded with two oxygen atoms and singly bonded with R and R dash groups.

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