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Organic Chemistry

Summary of Reactions

Organic ChemistrySummary of Reactions

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.
    2. Alkoxymercuration/demercuration
      Tetramethylethylene reacts with alcohol and mercury(2) acetate, then sodium borohydride in an oxymercuration-demercuration reaction, forming an ether product.
  2. 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.
    2. 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.
    3. 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.
  3. 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.
  4. Oxidation of thiols to disulfides (Section 18.7)
    Two thiols react with iodine and water to yield a disulfide compound (R S - S R).
  5. Synthesis of sulfides (Section 18.7)
    A thiolate anion reacts with an alkyl bromide to yield an alkyl thioether compound along with bromide ion.
  6. 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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