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)