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)