Lecture Outlines

Chapter 1. Structure Determines Properties

  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. Lewis Bonding Model
    1. Examples - Filled Outer Shells
    2. Formal Charge
    3. Multiple Bonds
  3. Bonding Concepts
    1. Ionic vs. Covalent Bonds
    2. Electronegativity and Bond Polarity
    3. Resonance
  4. Shapes of Molecules
    1. VSEPR Predictions
    2. Polarity of Molecules
  5. Representations of Chemical Structures
  6. Constitutional Isomerism
  7. Acids and Bases
    1. Brønsted Theory
      1. Definitions - Conjugate Acid-Base Pairs
      2. Use of Acidity Constants
    2. Lewis Acids and Bases

Chapter 2. Alkanes and Cycloalkanes: Introduction to Hydrocarbons

  1. Bonding and Classes of Hydrocarbons
    1. Examples of Alkanes, Alkenes, and Alkynes
    2. Quantum-mechanical Bonding Ideas
      1. Hybrid Orbital Concept
      2. Molecular Orbital (M.O.)Model
      3. Distinction between M.O. and Valence Bond Models
      4. Sigma Bonds vs. Pi Bonds
  2. Alkane Nomenclature
    1. Acyclic Alkanes
    2. Cycloalkanes
  3. Physical Properties of Alkanes
  4. Reactions of Alkanes
    1. Halogenation (Discussed in Chapter 4)
    2. Combustion
    3. Oxidation-Reduction Reactions in Organic Chemistry
  5. Sources of Hydrocarbons

Chapter 3. Alkanes and Cycloalkanes: Conformations and cis-trans Stereochemistry

  1. Conformations of Alkanes
    1. Newman Projections
    2. Conformational Analysis of Ethane
    3. Butane and Gauche Conformations
  2. 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
  3. Bicyclic and Spiro Compounds

Chapter 4. Alcohols and Alkyl Halides

  1. Nomenclature
  2. Properties
  3. Preparation of Alkyl Halides
    1. From Alcohols and HCl or HBr
      1. Reaction Summary
      2. SN1 Reaction Mechanism
      3. SN2 Reaction Mechanism
    2. From Alcohols and SOCl2 or PBr3
    3. From Alkanes and Cl2 or Br2
      1. Reaction Summary
      2. Regioselectivity
      3. Mechanism - Free Radical Chain Reaction
      4. Hammond's Postulate

Chapter 5. Structure and Preparation of Alkenes: Elimination Reactions

  1. Alkene Nomenclature
    1. Basics (and Cahn-Ingold-Prelog Priority Rules)
    2. Multiple Double Bonds
    3. Cycloalkenes
    4. Common Names
    5. Enols
  2. Alkene Structure and Bonding
  3. Relative Stability of Alkenes
  4. Elimination Reactions
    1. As Preparations of Alkenes
    2. The E1 Mechanism
    3. The E2 Mechanism

Chapter 6. Addition Reactions of Alkenes

  1. Electrophilic Additions to Alkenes
    1. Addition of HX
    2. Addition of H2SO4
    3. Acid-catalyzed Addition of HOH
    4. Addition of Br-Br and Cl-Cl
    5. Halohydrin Formation
  2. Other Alkene Addition Reactions
    1. Addition of H-H (Reduction of Alkenes)
    2. Free-radical Addition of HBr
    3. Hydroboration
  3. Oxidations of Alkenes
    1. Formation of Epoxides
    2. Ozonolysis
  4. Polymerization of Alkenes
    1. Cationic Polymerizations
    2. Free-radical Polymerizations

Chapter 7. Stereochemistry

  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
    1. Use of a Chiral Resolving Agent to Make Diastereomers
    2. Kinetic Resolution using a Chiral Catalyst

Chapter 8. Nucleophilic Substitution

  1. SN2 Reactions
    1. Rate Law
    2. Stereochemistry
    3. Nucleophiles and Nucleophilicity
    4. Common Solvents
    5. Steric Effect
  2. SN1 Reactions
    1. Stereochemistry
    2. Rate Law
    3. Carbocation Chemistry
    4. Solvolysis Reactions
  3. Sulfonate Leaving Groups
  4. Competing Elimination Reactions

Chapter 9. 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 (Hydrogenation)
    2. Hydration
    3. Electrophilic Additions

Chapter 10. Conjugation in Alkadienes and Allylic Systems

  1. Allylic Systems
    1. Resonance-stabilized Intermediates
    2. SN1 Reactions
    3. SN2 Reactions
    4. Halogenation
  2. Dienes
    1. Special Stability of Conjugated Dienes
    2. Bonding in Cumulated Dienes
    3. Preparation of Dienes
    4. Reactions of Dienes
      1. Electrophilic Additions (Kinetic vs. Thermodynamic Control)
      2. Diels-Alder Reaction

Chapter 11. Arenes and Aromaticity

  1. Examples of Aromatic Compounds
  2. Benzene
    1. Structure and Bonding Issues
    2. Bonding Models
  3. Hükel's Criteria for Aromaticity and Anti-Aromaticity
    1. Hükel Rules
    2. Hydrocarbon Examples
    3. MO Diagrams and Frost Circles
    4. Heterocyclic Examples
  4. Nomenclature of Substituted Benzenes
    1. Monosubstituted Benzenes
    2. Disubstituted Benzenes
    3. Polysubstituted Benzenes
  5. Reductions of Benzene Rings
  6. Reactions at Benzylic Carbons
    1. Similarities to Allylic Reactions
    2. Oxidations

Chapter 12. Reactions of Arenes: Electrophilic Aromatic Substitution

  1. Overview: Reactions with Benzene
  2. Mechanisms
    1. Bromination (and Chlorination)
    2. Nitration
    3. Sulfonation
    4. Friedel-Crafts Alkylation and Acylation
    5. Other Alkylations
  3. Directing Effects with Substituted Benzenes
    1. o,p Directors: Phenol Example
    2. m Directors: Nitrobenzene Example
  4. Activating vs. Deactivating Groups
    1. Electron Donors - Activating
    2. Electron Withdrawers - Deactivating
    3. Borderline Cases - Halogens
    4. Multiple Substitutent Effects
    5. Synthetic Considerations
  5. Beyond Benzene Derivatives
    1. Napthalene
    2. Heterocyclic Aromatics