Lewis Structure
Hybridization and Shape
Formal Charge
Resonance Structures
Constitutional Isomers
Nomenclature
Conformational Analysis
Newman Projection

Chapter 3 Alkenes and Alkynes

Nomenclature
Intermediates and transition states
Preparation of alkenes and alkynes
Reagents and reactions of alkenes and alkynes

Chapter 4 Stereochemistry

Chirality
Stereoisomers
Symmetry
Optical Activity
Synthesis

Chapter 5 Rings

Rings and strain
Stereochemistry of cyclohexane
Bicyclic compounds

Chapter 6 Nucleophilic substitution and Elimination reactions

SN2, SN1, E2, and E1 reactions
Mechanisms
Solvents
Reaction rates and rate laws
Stereochemistry

Chapter 7 Equilibria

Equilibrium
Intermediate
Transition state
Activation energy
Exothermic and endothermic reactions

Chapter 8 & 9Addition to alkenes & alkynes

Intermediates and transition states
Multi-step synthesis
Retrosynthetic analysis
Reagents and reactions of alkenes and alkynes

Chapter 10 Free Radicals

Radical stability and reactivity
Mechanisms (initiation, propagation, and termination)
Intermediates
Addition of HX to alkenes and aklynes

Summary of Reactions by Type

Substitution Reactions

SN2      Inversion of configuration
              Primary and secondary alkyl with good leaving group
              Strong nucleophile
              Polar aprotic solvent

SN1      Racimization (via carbocation)
              Tertiary alkyl with good leaving group
              Polar protic solvent and Heat

Radical Racimization (via radical)
              Radical Stability (just like carbocation)
              Requires initiation, propagation, and termination

Elimination Reactions

E2          Dehydrohalogenation
               Zaitsev product with small base
               Hoffman product with bulky base
               Secondary and tertiary alkyl with good leaving group
               Strong base and heat

E1          Dehydrohalogenation
               Formation of most stable alkene
               Carbocation rearragement (Hydride or alkyl shift)
               Tertiary alkyl with leaving group
               Weak base and heat

H2O      Formation of most stable alkene
               Carbocation rearragement (Hydride or alkyl shift)
               Catalytic acid and heat

 Addition reactions to alkene

Syn addition      hydrogenation
                           Diol formation with OsO4/Na2SO3
                           Epoxide formation
                           Hydroboration followed by oxidation

Anti addition     X2 addition
                           Hydronium addition and variation
                           Epoxide formation followed by addition of Nu

Markovnikov  Hydration reaction
                           Oxymercuration/demercuration
                           HX addition

Anit-
Markovnikov Hydroboration/Oxydation reaction
                          Radical additon of HX

Addition Reacations to Alkynes

Syn                   Hydrogenation reaction

Anti                  Dissolved electron
                           X2 addition

Markovnikov  HX addition

Alkene and Alkyne Cleavage via Oxidation

Alkene              1) KMnO4/OH?, Heat 2) H3O+
                           Form ketones, carboxylic acids, CO2

                            1) O3 2) Zn, HOAc
                            Form ketone, aldehyde

Alkyne               1) KMnO4/OH?, Heat 2) H3O+
                            Form carboxylic acid, formic acid

                            1) O3 2) Zn, HOAc
                            Form carboxylic acids, CO2

C-C Bond Forming Reactions

Alkylation of alkynide anions ? primary alkyl halides, epoxides
Reaction of lithium dialkylcuprates (Gillman’s reagent)
Cationic Polymerization reactions of aklenes
Radical Polymerization reactions of aklenes

Miscellaneous Reactions

Ketone with PCl5
Terminal alkynes with strong base
Formation of alkyl tosylates
Deprotonation of alcohols