CHEM 2423 Course Objectives


Section numbers reference "Organic Chemistry" Wade, 4th ed.


R = review

O = optional

2 = secondary emphasis


1. Introduction and Review

R              1-1              The Origins of Organic Chemistry

R              1-2              Principles of Atomic Structure

R              1-3              Bond Formation: The Octet Rule

R              1-4              Lewis Structures

R              1-5              Multiple Bonding

R              1-5              Electronegativity and Bond Polarity

R              1-6              Formal Charges

R              1-7              Summary: Common Bonding Patterns in Organic Compounds and Ions

R              1-8              Ionic Structures

R              1-9              Resonance

R              1-10            Structural Formulas

R              1-11            Molecular Formulas and Empirical Formulas

R              1-12            Arrhenius Acids and Bases

R              1-13            Brönsted-Lowry Acids and Bases

R              1-14            Lewis Acids and Bases


2. Structure and Properrties of Organic Molecules

R              2-1     Wave Properties of Electrons in Orbitals

R              2-2     Molecular Orbitals

R              2-3     Pi Bonding

R              2-4     Hybridization and Molecular Shapes

R              2-5     Drawing Three-Dimensional Molecules

R              2-6     General Rules of Hybridization and Geometry

R              2-7      Rotation of Single Bonds

R              2-8     Rigidity of Double Bonds

R              2-9     Constitutional Isomerism

R              2-10    Stereoisomerism

R              2-11    Polarity of Bonds and Molecules

R              2-12    Intermolecular Attractions and Repulsions

R              2-13    Polarity Effects on Solubilities

R              2-14    Hydrocarbons

R              2-15    Organic Compounds Containing Oxygen

                 R     2-16    Organic Compounds Containing Nitrogen


3. Structure and Stereochemistry of Alkanes

                  3-1     Classification of Hydrocarbons

                  3-2     Molecular Formulas of Alkanes

                  3-3     Nomenclature of Alkanes

                  3-4     Physical Properties of Alkanes

                  3-5     Uses and Sources of Alkanes

                  3-6     Reactions of Alkanes

                  3-7     Structure and Conformations of Alkanes

                  3-8     Conformations of Butane

                  3-9     Conformations of Higher Alkanes

                  3-10    Cycloalkanes

                  3-11    Cis-trans Isomerism in Cycloalkanes

                  3-12    Stabilities of Cycloalkanes; Ring Strain

                  3-13    Cyclohexane Conformations

                  3-14    Conformations of Monosubstituted Cyclohexanes

                  3-15    Conformations of Disubstituted Cyclohexanes

                  3-16    Bicyclic Molecules


4. The Study of Chemical Reactions

                 4-2     Chlorination of Methane

                 4-3     The Free-Radical Chain Reaction

                 4-4     Equilibrium Constants and Free Energy

                 4-5     Enthalpy and Entropy

                 4-6     Bond Dissociation Energies

                 4-7     Calculation of Enthalpy Changes in Chlorination

                 4-8     Kinetics and the Rate Equation

                 4-9     Activation Energy and the Temperature Dependence of Rates

                 4-10    Transition States

                 4-11    Rates of Multistep Reactions

                 4-12    Isotope Effects

                 4-13    Temperature Dependence of Halogenation

                 4-14    Halogenation of Higher Alkanes

                 4-15    The Hammond Postulate

                 4-16    Reactive Intermediates


5. Stereochemistry

                 5-2       Chirality

                 5-3       (R) and (S) Nomenclature of Chiral Carbon Atoms

                 5-4       Optical Activity

                 5-5       Biological Discrimination of Enantiomers

                 5-6       Racemic Mixtures

                 5-7       Enantiomeric Excess and Optical Purity

                 5-8       Chirality of Conformationally Mobile Systems                     

                 5-9       Chiral Compounds Without Chiral Carbon Atoms

                 5-10     Fischer Projections

                  5-11      Diastereomers

                  5-12      Stereochemistry of Molecules with Two or More Chiral Carbon Atoms

                  5-13      Meso Compounds

                  5-14      Absolute and Relative Configurations

                  5-15      Physical Properties of Diasteromers

                  5-16      Resolution of Enantiomers

                  5-17      Stereochemistry of Chemical Reactions: An Overview


6. Alkyl Halides: Nucleophilic Substitution and Elimination

                 6-2       Nomenclature of Alkyl Halides

                 6-3       Common Uses of Alkyl Halides

                 6-4       Structure of Alkyl Halides

                 6-5       Physical Properties of Alkyl Halides

                 6-6       Preparation of Alkyl Halides

                 6-7       Reactions of Alkyl Halides: Substitution and Elimination

                 6-8       Second-Order Nucleophilic Substitution: The SN2 Reaction

                 6-9       Generality of the SN2 Reaction

                 6-10      Factors Affecting SN2 Reactions: Strength of the Nucleophile

                 6-11      Reactivity of the Substrate in SN2 Reactions

                 6-12      Stereochemistry of the SN2 Reaction

                 6- 13     First-Order Nucleophilic Substitution: The SNI Reaction

                 6- 14     Stereochemistry of the SNI Reaction

                 6-15      Rearrangements in SNI Reactions

                 6-16      Comparison of SNI and SN2 Reactions

                 6-17      First-Order Elimination: The E1 Reaction

                 6-18      Second-Order Elimination: The E2 Reaction

                 6-19      Positional Orientation of Elimination: The Saytzeff Rule

                 6-20      Stereochemistry of the E2 Reaction

                 6-21      Comparison of El and E2 Elimination Mechanisms

                 6-22      Substitution Versus Elimination


7. Structure and Synthesis of Alkenes

                 7-2        The Orbital Description of the Alkene Double Bond

                 7-3        Elements of Unsaturation

                 7-4        Nomenclature of Alkenes

                 7-5        Nomenclature of Cis-Trans Isomers

                 7-6        Commercial Importance of Alkenes

                 7-7        Stability of Alkenes

                 7-8        Physical Properties of Alkenes

                 7-9        Alkene Synthesis by Elimination of Alkyl Halides

                 7-10      Alkene Synthesis by Dehydration of Alcohols

                 7-11      Alkene Synthesis: High-Temperature industrial Methods


8. Reactions of Alkenes

                  8-1        Reactivity of the Carbon-Carbon Double Bond

                  8-2        Electrophilic Addition to Alkenes

                  8-3        Addition of Hydrogen Halides to Alkenes

                  8-4        Addition of Water: Hydration of Alkenes

                  8-5        Indirect Hydration of Alkenes

                  8-8        Catalytic Hydrogenation of Alkenes

O              8-9        Addition of Carbenes to Alkenes

                  8-10      Addition of Halogens to Alkenes

                  8-11      Formation of Halohydrins

                  8-12      Epoxidation of Alkenes

                  8-14      Syn Hydroxylation of Alkenes

                  8-15      Oxidative Cleavage of Alkenes

                  8-16      Polymerization of Alkenes


9. Alkynes

                 9-2     Nomenclature of Alkynes

                 9-3     Physical Properties of Alkynes

                 9-4     Commercial Importance of Alkynes

                 9-5     Electronic Structure Of AlkYnes

                 9-6     Acidity of Alkynes

                 9-7     Synthesis of Alkynes from Acetylides

                 9-8      Synthesis of Alkynes by Elimination Reactions

                 9-9      Addition Reactions of Alkynes

                 9-10    Oxidation of Alkynes


15. Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

                 15-2     Stabilities of Dienes

                 15-3     Molecular Orbital Picture of a Conjugated System

                 15-4     Allylic Cations

                 15-5     1,2- and 1,4-Addition to Conjugated Dienes

                 15-6     Kinetic vs Thermodynamic Control in the Addition of HBr to 1,3-Butadiene

                 15-7     Allylic Radicals

                 15-8     Molecular Orbitals of the Allylic System

                 15-9     Electronic Configurations of the Allyl Radical, Cation, and Anion

                 15-10    SN2 Displacement Reactions of Allylic Halides and Tosylates

                 15-11    The Diels -Alder Reaction

                 15-12    The Diels- Alder as an Example of a Pericyclic Reaction


16. Aromatic Compounds

                 16-1     The Discovery of Benzene

                 16-2     The Structure and Properties of Benzene

                 16-3     The Molecular Orbitals of Benzene

                 16-4     The Molecular Orbital Picture of Cyclobutadiene

                 16-5     Aromatic, Antiaromatic, and Nonaromatic Compounds

                 16-6     Huckel's Rule

                 16-7     Molecular Orbital Derivation of Hiickel's Rule

                 16-8     Aromatic Ions

2               16-9     Heterocyclic Aromatic Compounds

2               16-10   Polynuclear Aromatic Hydrocarbons

2               16-11    Fused Heterocyclic Compounds

                 16-12   Nomenclature of Benzene Derivatives

                 16-13   Physical Properties of Benzene and Its Derivatives

                 16-14   Spectroscopy of Aromatic Compounds


17. Reactions of Aromatic Compounds

                 17-1    Electrophilic Aromatic Substitution

                 17-2    Halogenation of Benzene

                 17-3    Nitration of Benzene

                 17-4    Sulfonation of Benzene

                 17-5    Nitration of Toluene: The Effect of Alkyl Substitution

                 17-6    Activating, Ortho, Para-Directing Substituents

                 17-7    Deactivating, Meta-Directing Substituents

                 17-8    Halogen Substituents: Deactivating, but Ortho, Para-Directing

                 17-9    Effects of More than One Substituent on Electrophilic Aromatic Subst.

                 17-10   The Friedel-CraftsAlkylation

                 17-11   The Friedel-Crafts Acylation

                 17-12   Nucleophilic Aromatic Substitution

                 17-13   Addition Reactions of Benzene Derivatives

                 17-14   Side-Chain Reactions of Benzene Derivatives