Lecture Outlines

Chapter 13. Nuclear Magnetic Resonance (NMR) Spectroscopy

  1. Physical Basis
    1. Nuclear Magnetic Resonance
    2. Chemical Shift
    3. Spin-Spin Splitting
    4. Signal Integration
  2. Interpreting Proton NMR Spectra
    1. Index of Hydrogen Deficiency
    2. Example
  3. Instrumentation
  4. Topicity of Atoms or Groups
  5. Fast Chemical Exchange
  6. Instrumentation
  7. 13-C NMR

Chapter 15. Organometallic Compounds

  1. Carbon-Metal Bonds
  2. Classical Organometallic Reagents
    1. Grignard Reagents
    2. Organo Lithium Reagents
    3. Gilman Reagents
  3. Reactions Involving Carbenes

Chapter 16. Aldehydes and Ketones

  1. Nomenclature
  2. Structure and Bonding
  3. Preparation of Aldehydes and Ketones
  4. Reactions
    1. Addition Reactions
    2. The Wittig Reaction
    3. Reactions alpha to the Carbonyl Carbon
    4. Oxidations
    5. Reductions

Chapter 17. Carboxylic Acids

  1. Structure and Bonding
  2. Nomenclature
  3. Properties
  4. Preparations of Carboxylic Acids
    1. Oxidation of Alcohols
    2. Grignard Reactions
  5. Reactions
    1. Reductions
    2. Esterification
    3. Acid Chloride Formation
    4. Decarboxylation

Chapter 18. Carboxylic Acid Derivatives

  1. Nomenclature and Examples
  2. Nucleophilic Acyl Substitution Reactions
  3. Preparations and Reactions
    1. Acid Chlorides
    2. Acid Anhydrides
    3. Esters
    4. Amides
    5. Nitriles

Chapter 14. Mass Spectrometry

  1. Principles and Instrumentation
  2. Analysis of Mass Spectra
    1. Molecular Ion
    2. Fragmentation Patterns
    3. Isotope Patterns

Chapter 19. Enolate Anions and Enamines (Carbonyl Condensation Reactions and Rections of alpha-beta-Unsaturated Carbonyl Compounds)

  1. Enolates and Enamines
  2. Aldol Reaction
    1. Mechanism
    2. Use in Synthesis
    3. Intramolecular Aldol Reactions
  3. Condensations with Esters
    1. Claisen Condensation
    2. Diekmann Condensation
    3. Crossed Claisen Condensatsions
    4. Hydrolysis and Decarboxylation
  4. Reactions with Enamines
  5. Acetoacetic Ester Synthesis and Malonic Ester Synthesis
  6. Conjugate Additions to alpha-beta-Unsaturated Carbonyl Compounds

Chapter 20. Dienes, Conjugated Systems, and Pericyclic Reactions

  1. Special Stability of Conjugated Dienes
    1. Evidence from Heats of Reactions
    2. Resonance View
    3. Molecular Orbital View
  2. Electrophilic Additions to Conjugated Dienes
    1. Reaction and Mechanism
    2. Thermodynamic vs. Kinetic Control
  3. Pericyclic Reactions
    1. Diels-Alder Reaction
    2. Cope and Claisen Rearrangements
  4. UV-Visible Spectroscopy
    1. Physical Basis / Alkene Example
    2. Other Examples
    3. Typical Use

Chapter 21. Benzene and the Concept of Aromaticity

  1. Examples of Aromatic Compounds
  2. Benzene
    1. Structure and Bonding Issues
    2. Bonding Models
  3. Huckel's Criteria for Aromaticity
    1. The Rules
    2. Why 4n+2?
    3. Heterocyclic Examples
    4. Polycyclic Aromatics
  4. Nomenclature
    1. Monosubstituted Benzenes
    2. Disubstituted Benzenes
  5. Selected Reactions of Phenols and Reactions at Benzylic Positions
    1. Reactions of Phenols
    2. Reactions at Benzylic Positions
  6. NMR Spectroscopy of Benzene Derivatives

Chapter 22. Reactions of Benzene and its Derivatives

  1. Electrophilic Aromatic Substitution Reactions
    1. Reactions of Benzene
    2. Mechanisms
    3. Directing Effects
    4. Activating and Deactivating Groups
  2. Useful Reactions of Benzene Substituents
  3. Nucleophilic Aromatic Substitution Reactions
    1. Addition-Elimination Mechanism
    2. Benzyne Intermediate Mechanism

Chapter 23. Amines

  1. Nomenclature and Examples
    1. Aliphatic Amines
    2. Aromatic Amines
    3. Alkaloids
  2. Properties
  3. Preparations of Amines
    1. Alkylation of Ammonia and Amines
    2. Reductions of Amides and Nitriles
    3. From Epoxides Hofmann Rearrangement ~~!>
    4. Reductive Amination of Aldehydes and Ketones
    5. Reduction of Amides
    6. Reduction of Nitrobenzenes
  4. Reactions of Amines
    1. Alkylation and Acylation
    2. Imine and Enamine Formation
    3. Two Special Elimination Reactions
    4. Reactions with Nitrous Acid
    5. Reactions of Aryl Diazonium Salts

Chapter 24. Catalytic C-C Bond Formation

  1. Review of C-C Bond Forming Reactions
  2. Palladium-Catalyzed Coupling Reactions
    1. Heck Reaction
    2. Suzuki Coupling
    3. Stille Coupling
    4. Sonoashira Coupling
  3. Alkene Metathesis
Skip section 24.4 (Catalytic Allylic Alkylation)

Chapter 29. Polymer Chemistry

  1. Introduction
  2. Polymer Notation
  3. Polymer Characteristics
  4. Polymerization Reactions
    1. Step Growth
    2. Chain Growth
    3. Ring-Opening Metathesis