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