Chapter 1. Covalent Bonds and Shapes of Molecules

1. Molecular Structure
   1. Illustration - A Detailed Look at the Structure of Methane
   2. A Chemist's Representation of the Methane Structure
   3. Review of the Electronic Structure of Atoms
2. Bonding Theories
   1. Lewis Model
      1. Examples -- Filled Outer Shells
      2. Formal Charge
      3. Multiple Bonds
   2. Molecular Orbital Models
3. Bonding Concepts
   1. Ionic vs. Covalent Bonds
   2. Electronegativity and Bond Polarity
   3. Resonance
   4. s (sigma) vs. p (pi) Bonds
4. Shaped of Molecules
   1. VSEPR Predictions
   2. Hybrid Orbitals
5. Introduction to Functional Groups

Chapter 2. Alkanes and Cycloalkanes

1. Alkanes
   1. Drawing Alkane Structures
   2. Constitutional Isomerism
   3. Nomenclature
   4. Classification of C and H Types
2. Cycloalkanes
   1. Monocyclic Alkanes
   2. Bicyclic Alkanes
3. Conformations of Alkanes
   1. Newman Projections
   2. Conformational Analysis of Ethane
   3. Butane and Gauche Conformations
4. Cycloalkanes -- Special Issues
   1. Conformations of Cyclohexane
      1. Drawing Chair Conformations
      2. Ring "Flipping"
      3. Analysis of Substituted Cyclohexanes
   2. Cis-Trans Isomerism in Cycloalkanes
5. Physical Properties of Alkanes
6. Reactions of Alkanes
   1. Oxidation (Combustion)
   2. Halogenation (Discussed in Chapter 7)
7. Sources of Alkanes

Chapter 3. Chirality

1. Enantiomers
   1. Definition
   2. Stereocenters
   3. R/S Nomenclature
2. Properties of Enantiomers
   1. Optical Activity
   2. Physical Properties
3. Molecules with Two or More Stereocenters
4. Resolution of Racemic Mixtures

Chapter 4. Acids and Bases

1. Brønsted Theory
   1. Definitions -- Conjugate Acid-Base Pairs
   2. Use of Acidity Constants
2. Explaining Trends in Acidity (and Basicity)
   1. Inductive Effects
   2. Resonance Effects
3. Lewis Acids and Bases

Chapter 5. Alkenes I

1. Structure and Bonding
   1. Valence Bond Picture
   2. Molecular Orbital Diagram
   3. Bond Lengths and Strengths
2. Alkene Nomenclature
   1. Basics
   2. Compounds with More than One Double Bond
   3. Cyclic Alkenes
   4. Some Common Names
3. Naturally-Occurring Alkenes: Examples

Chapter 6. Alkenes II

1. Electrophilic Additions to Alkenes
   1. Addition of HX; First Look at a Detailed Reaction Mechanism
   2. Hydration of Alkenes
   3. Oxymercuration/Demercuration
   4. Addition of Br-Br and Cl-Cl
   5. Halohydrin Reactions
2. Other Types of Additions
   1. Hydroboration
   2. Addition of H-H (Reduction of Alkenes)
3. Oxidations of Alkenes
   1. Formation of Glycols
   2. Ozonolysis
   3. Oxidation/Reduction Reactions in Organic Chemistry
4. Reactions Involving Stereocenters

Chapter 7. Haloalkanes, Alkanes, and Arenes

1. Nomenclature
2. Physical Properties of Alkyl Halides
3. Common or Interesting Alkyl Halides
4. Preparation of Alkyl Halides
   1. Halogenation of Alkanes
      1. Regioselectivity
      2. Mechanism -- Free Radical Chain Reaction
      3. Hammond's Postulate
   2. Allylic Halogenation
      1. Allylic Radicals
      2. N-bromosuccinamide Reactions (NBS)

Chapter 8. Nucleophilic Substitution and Beta-Elimination

1. Substitution Reactions
   1. SN2 Reactions
   2. SN1 Reactions
   3. Related Concepts and Terms
2. Elimination Reactions
   1. E2 Reactions
   2. E1 Reaction
3. Competing Reactions/Predicting Reactivity: SN2, SN1, E1, or E2?
4. Special Topics
   1. Neighboring-Group Participation
   2. Phase-Transfer Catalysis

Chapter 9. Alcohols and Thiols

1. Nomenclature
2. Properties
   1. Hydrogen Bonding
   2. Solubility
   3. Acidity
3. Preparations of Alcohols
4. Reactions of Alcohols
   1. Preparation of Alkoxide Ions
   2. Substitution Reactions
   3. Elimination Reactions
   4. Oxidations
5. Special Reactions of 1,2-Diols
6. Reactions of Thiols

Chapter 10. Alkynes

1. Structure and Bonding
2. Nomenclature
3. Preparations of Alkynes
   1. Double Elimination
   2. Use of Acetylide Anions
4. Reactions of Alkynes
   1. Reduction
   2. Hydroboration
   3. Electrophilic Additions
   4. Acidity of Terminal Alkynes

Chapter 11. Ethers, Epoxides, and Sulfides

1. Ethers
   1. Nomenclature
   2. Properties
   3. Preparations
   4. Reaction
2. Epoxides
   1. Properties
   2. Preparations
   3. Reaction
3. Sulfides
4. Crown Ethers
5. Use of Ethers as Protecting Groups

Chapter 13. Nuclear Magnetic Resonance (NMR) Spectroscopy

1. Physical Basis
2. Chemical Shift
3. Spin-Spin Splitting
4. Integration
5. Interpreting Proton NMR Spectra
6. Effect of Stereocenters
7. Instrumentation
8. 13-C NMR

Ch 13 section not covered: The DEPT Method (section 13.13).