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Organic Chemistry

Summary of Reactions

Organic ChemistrySummary of Reactions
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8 • Summary of Reactions

8 • Summary of Reactions

No stereochemistry is implied unless specifically indicated with wedged, solid, and dashed lines.

  1. Addition reactions of alkenes
    1. Addition of HCl, HBr, and HI (Section 7.7 and Section 7.8)
       Markovnikov regiochemistry occurs, with H adding to the less highly substituted alkene carbon and halogen adding to the more highly substituted carbon.
    2. Addition of halogens Cl2 and Br2 (Section 8.2)
       Anti addition is observed through a halonium ion intermediate.
    3. Halohydrin formation (Section 8.3)
       Markovnikov regiochemistry and anti stereochemistry occur.
    4. Addition of water by oxymercuration–demercuration (Section 8.4)
       Markovnikov regiochemistry occurs.
    5. Addition of water by hydroboration–oxidation (Section 8.5)
       Non-Markovnikov syn addition occurs.
    6. Catalytic hydrogenation (Section 8.6)
       Syn addition occurs.
    7. Epoxidation with a peroxyacid (Section 8.7)
       Syn addition occurs.
    8. Hydroxylation with OsO4 (Section 8.7)
       Syn addition occurs.
    9. Addition of carbenes to yield cyclopropanes (Section 8.9)

      (1) Dichlorocarbene addition

      (2) Simmons–Smith reaction

  2. Hydroxylation by acid-catalyzed epoxide hydrolysis (Section 8.7)
     Anti stereochemistry occurs.
  3. Oxidative cleavage of alkenes (Section 8.8)
    1. Reaction with ozone followed by zinc in acetic acid
    2. Reaction with KMnO4 in acidic solution
  4. Cleavage of 1,2-diols (Section 8.8)
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