organic chemistry quiz


Chapter 10: Radical Reactions


  • Understand homolysis of covalent bonds and the use of single-barbed arrows to show the movement of unpaired electrons.
  • Radical halogenation of alkanes (know reaction and radical mechanism)
  • Understand selectivity in radical halogenation of alkanes
  • Understand stability of radicals and how homolytic bond dissociation energies relate to radical stability.
  • Be able to predict the stereochemical outcome of a radical halogenation reaction.
  • Radical addition of HBr to alkenes (know reaction and radical mechanism)


Chapter 8: Alkenes and Alkynes II


*Note: Make sure to understand stereochemistry and regiochemistry of reactions whenever applicable.


  • Addition of hydrogen halides to alkenes (know reaction, mechanism, Markovnikov’s rule, etc.)
  • Acid-catalyzed hydration of alkenes (know reaction and mechanism, and possibility of rearrangements)
  • Oxymercuration-demercuration of alkenes (know reaction, and mechanism for the oxymercuration step)
  • Hydroboration/oxidation of alkenes (know reaction, and know mechanism and stoichiometry for the hydroboration step)
  • Addition of Br2 and Cl2 to alkenes in non-nucleophilic solvent (know reaction and mechanism)
  • Addition of Br2 and Cl2 to alkenes in nucleophilic solvent (know reaction and mechanism)
  • Carbene insertion reactions to synthesize cyclopropanes (know reactions and reagent systems used to carry out these reactions as discussed in lecture)
  • Syn-1,2 dihydroxylation of alkenes with OsO4 or with cold, basic KMnO4 (know reactions)
  • Oxidative cleavage of alkenes with hot, basic KMnO4 (know reaction)
  • Oxidative cleavage of alkenes with ozone (know reaction)



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