CONTENTS
Chapter
1: Introduction to Structure and Models of Bonding
Intent and Purpose.
1.1 A Review of Basic Bonding Concepts.
1.2
A More Modern Theory of Organic Bonding
1.3 Orbital Mixing – Building Larger Molecules
1.4 Bonding and Structure of Reactive Intermediates
1.5
A Very Quick Look at Organometallic and Inorganic Bonding
Chapter
2: Strain and Stability
Intent and Purpose
2.1
Thermochemistry of Stable Molecules
2.2
Thermochemistry of Reactive Intermediates
2.3
Relationships between Structure and Energetics; Basic Conformational Analysis
2.4
Electronic Effects
2.5 Highly Strained Molecules
2.6
Molecular Mechanics
Chapter
3: Solutions and Noncovalent Binding Forces
Intent and Purpose
3.1
Solvent and Solution Properties
3.2
Binding Forces
3.3 Computational Modeling of Solvation
Chapter
4: Molecular Recognition and Supramolecular Chemistry
Intent and Purpose
4.1 Thermodynamic Analyses of Binding
Phenomena
4.2 Molecular Recognition
4.3 Supramolecular Chemistry
Chapter
5: Acid-Base Chemistry
Intent and Purpose
5.1 Brønsted Acid and Base Chemistry
5.2 Aqueous Solutions
5.3 Nonaqueous Systems
5.4 Predicting Acid Strength
5.5 Acids-Bases of Bioorganic Interest
5.6 Lewis Acids/Bases and Electrophiles/Nucleophiles
Chapter
6: Stereochemistry
Intent and Purpose
6.1 Stereogenicity
and Stereoisomerism
6.2 Symmetry and Stereochemistry
6.3 Topicity Relationships
6.4 Reaction Stereochemistry: Stereoselectivity and Stereospecificity
6.5 Symmetry and Timescale
6.6 Topological and Supramolecular Stereochemistry
6.7 Stereochemical Issues in Polymer Chemistry
6.8 Stereochemical Issues in Chemical Biology
Summary and Outlook
Chapter
7: Energy Surfaces and Kinetic Analyses
Intent and Purpose:
7.1
Energy Surfaces and Related Concepts
7.2 Transition State Theory (TST), and Related Topics
7.3 Postulates and Principles Related to Kinetic Analysis
7.4 Kinetic
Experiments
7.5
Complex Reactions - Deciphering Mechanisms
7.6 Methods for Following Kinetics
7.7 Calculating Rate Constants
7.8 Considering Multiple Reaction Coordinates
Summary and Outlook
Chapter
8: Experiments Related to Thermodynamics and Kinetics
Intent and Purpose
8.1 Isotope Effects
8.2 Substituent
Effects
8.3 Hammett Plots, The Most Common LFER. A General Method for Examining Changes in Charges During a Reaction
8.4 Other Linear Free Energy Relationships
8.5 Acid/Base Related
Effects / Brønsted Relationships
8.6 Why do Linear
Free Energy Relationships Work?
8.7
Summary of Linear Free Energy Relationships
8.8 Miscellaneous Experiments for Studying Mechanisms
Chapter
9: Catalysis
Intent and Purpose
9.1 General Principles of Catalysis
9.2 Forms of Catalysis
9.3 Brønsted Acid/Base Catalysis
9.4 Enzymatic Catalysis
Chapter 10: Organic Reaction Mechanisms Part 1: Reactions Involving Additions and/or Eliminations
Intent and Purpose
10.1
Predicting Organic Reactivity
10.2 Hydration of
Carbonyl Structures
10.3
Electrophilic Addition of Water to Alkenes and Alkynes: Hydration
10.5 Electrophilic
Addition of Halogens to Alkenes
10.6
Hydroboration
10.7 Epoxidation
10.8
Nucleophilic Additions to Carbonyl Compounds
10.9 Nucleophilic Additions to Olefins
10.10
Radical Additions to Unsaturated Systems
10.11
Carbene Additions and Insertions
10.13
Elimination Reactions for Aliphatic Systems, Formation of Alkenes
10.14
Eliminations from Radical Intermediates
10.15
Addition of Nitrogen Nucleophiles To Carbonyl Structures, Followed by
Elimination
10.16 Addition of Carbon Nucleophiles, Followed by Elimination – The Wittig Reaction
10.18
Electrophilic Aromatic Substitution
10.19 Nucleophilic Aromatic Substitution
10.22
Radical Aromatic Substitutions
Chapter 11: Organic
Reaction Mechanisms Part II: Substitutions at Aliphatic Centers and Thermal
Isomerizations/Rearrangements
Intent
and Purpose
11.1
Tautomerization
11.2 a-Halogenation
11.3 a-Alkylations
11.4 The Aldol Reaction
11.5 Nucleophilic Aliphatic Substitution Reactions
11.6 Substitution – Radical - Nucleophilic
11.7 Radical Aliphatic Substitutions
11.8 Migrations to Electrophilic Carbon
11.9 Migrations to Electrophilic Heteroatoms
11.10 The
Favorskii Rearrangement and Other Carbanion Rearrangements
11.11
Rearrangements Involving Radicals
11.12
Rearrangements and Isomerizations Involving Biradicals
Intent and Purpose:
12.1
The Basics of Organometallic Complexes
12.2
Common Organometallic Reactions
12.3 Combining the
Individual Reactions into Overall Transformations and Cycles
Chapter
13. Organic Polymer
and Materials Chemistry
Intent
and Purpose
13.1 Structural Issues in Materials Chemistry
13.2
Common Polymerization Mechanisms
Intent and Purpose
14.1
Introductory Quantum Mechanics
14.2 Calculational Methods - Solving the Schrödinger Equation for Complex Systems
14.3 A Brief Overview of the Implementation and Results of HMOT
14.4 Perturbation Theory - Orbital Mixing Rules
14.5 Some Topics in Organic
Chemistry for Which Molecular Orbital Theory Lends Important Insights
14.6 Organometallic Complexes
Intent and Purpose
15.1 Background
15.2 A Detailed Analysis of Two Simple Cycloadditions
15.3. Cycloadditions
15.4 Electrocyclic Reactions
15.5 Sigmatropic Rearrangements
15.6 Chelotropic Reactions
15.7 In Summary, Applying the Rules
Summary
and Outlook
Intent and Purpose
16.1 Photophysical Processes – the Jablonski Diagram
16.2 Bimolecular Photophysical
Processes
16.3 Photochemical Reactions
16.4 Chemiluminescence
16.5
Singlet Oxygen
Chapter
17: Electronic Organic Materials
Intent and Purpose
17.1 Theory
17.2 Conducting Polymers
17.3 Organic Magnetic Materials
17.4 Superconductivity
17.5 Nonlinear Optics (NLO)
17.6 Photoresists
17.7
Summary