Lecture Outlines

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
      4. Lewis Models with S or P
    2. Quantum Mechanical Bonding Issues
      1. Molecular Orbitals
      2. sigma vs. pi Bonds
      3. Hybrid Atomic Orbitals
  3. Bonding Concepts
    1. Ionic vs. Covalent Bonds
    2. Electronegativity and Bond Polarity
    3. Resonance
  4. Shapes of Molecules
    1. VSEPR Predictions
    2. More Hybrid Orbitals
  5. Introduction to Functional Groups

Chapter 2. Alkanes and Cycloalkanes

  1. Alkanes
    1. 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. Conformations and Structures of Cycloalkanes
    1. Rings with Fewer than Six Carbon Atoms
    2. Cyclohexane Conformations
      1. Drawing Chair Conformations
      2. Ring "Flipping"
      3. Analysis of Substituted Cyclohexanes
    3. Cis-Trans Isomerism in Cycloalkanes
  5. Physical Properties of Alkanes
  6. Reactions of Alkanes
    1. Oxidation (Combustion)
    2. Halogenation (Discussed in Chapter 8)
  7. Sources of Alkanes

Chapter 3. Chirality

  1. Enantiomers
    1. Definition
    2. Stereocenters
    3. R/S Nomenclature
    4. Fischer Projections
  2. Properties of Enantiomers
    1. Optical Activity
    2. Physical Properties
    3. Chemical Reactivity
  3. Molecules with Two or More Stereocenters
  4. Resolution of Racemic Mixtures
Sections not covered: 3.8, 3.9B, 3.9C.

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. Very Weak C-H Acidity
  4. Lewis Acids and Bases
  5. Reaction Coordinate Diagrams

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
Sections not covered: Index of Hydrogen Deficiency, p. 193.

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/Reduction
    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
  5. Relative Stability of Alkenes
Sections not covered: 6.7C.

Chapter 7. Alkynes

  1. Structure and Bonding
  2. Nomenclature
  3. Acidity of Terminal Alkynes
  4. Preparations of Alkynes
    1. Double Elimination
    2. Use of Acetylide Anions
  5. Reactions of Alkynes
    1. Reduction
    2. Hydroboration
    3. Electrophilic Additions
Sections not covered: 7.8B

Chapter 8. Haloalkanes, Halogenation, and Radical Reactions

  1. Nomenclature
  2. Physical Properties of Alkyl Halides
  3. Common or Interesting Alkyl Halides
  4. Preparation of Alkyl Halides
    1. Preparations from Alkenes and Alkynes
    2. Halogenation of Alkanes
      1. Regioselectivity
      2. Mechanism - Free Radical Chain Reaction
      3. Hammond's Postulate
    3. Allylic Halogenation
      1. Allylic Radicals
      2. N-bromosuccinamide Reactions (NBS)
    4. Radical Addition of HBr to Alkenes
  5. Autooxidation Reactions

Chapter 9. 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. Leaving Groups
  5. Special Topic: Neighboring-Group Participation
      Phase-Transfer Catalysis ~~>

Chapter 10. Alcohols and Thiols

  1. Nomenclature
  2. Properties
    1. BP/MP Trends
    2. Solubility
  3. Preparations of Alcohols
  4. Reactions of Alcohols
    1. Preparation of Alkoxide Ions
    2. Substitution Reactions
    3. Preparation of Sulfonates
    4. Elimination Reactions
    5. Oxidations
  5. Special Reactions of 1,2-Diols
  6. Reactions of Thiols
Sections not covered: 10.8D

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. Protecting/Deprotection of Alcohols

Chapter 12. Infrared (IR) Spectroscopy

  1. Physical Basis for IR Spectroscopy
  2. Vibrational Modes
    1. Examples
    2. Signal Intensity
    3. Frequency Trends
  3. Group Frequencies