Perspectives On Structure And Mechanism In Organic Chemistry - 98 edition

PART I. CONCEPTS AND MODELS IN ORGANIC CHEMISTRY.

Models of Atomic and Molecular Structure.
Bonding and Molecular Geometry.
Complementary Descriptions of the Double Bond.
Conclusion.

PART II. STEREOCHEMISTRY.

Introduction.
Stereoisomerism.
Manifestations of Stereoisomerism.

PART III. CONFORMATIONAL ANALYSIS AND MOLECULAR MECHANICS.

Molecular Conformation.
Conformational Analysis.
Molecular Mechanics.
Molecular Strain and Limits to Molecular Stability.

PART IV. APPLICATIONS OF MOLECULAR ORBITAL THEORY AND VALENCE BOND THEORY.

Introduction to Molecular Orbital Theory.
Armoaticity.
Quantitative Methods Using Valence Bond Theory.
Additional Molecular Orbital Methods.

PART V. REACTIVE INTERMEDIATES.

Potential Energy Surfaces, Reaction Coordinate Diagrams, and Reactive Intermediates.
Reactive Intermediates with Neutral, Electron Deficient Carbon Atoms.
Intermediates with Charged Carbon Atoms.
Conclusion.

PART VI. METHODS OF STUDYING ORGANIC REACTIONS.

Molecular Change and Reaction Mechanisms.
Tools to Determine Reaction Mechanisms.
Applications of Kinetics in Studying Reaction Mechanisms.
Arrhenius Theory and Transition-State Theory.
Kinetic Isotope Effects.
Substituent Effects and Linear Free Energy Relationships.

PART VII. ACID-BASE CATALYZED REACTIONS.

Acidity and Basicity of Organic Compounds.
Acid and Base Catalysis of Chemical Reactions.
Acid and Base Catalysis of Carbonyl Compounds and Carboxylic Acid Derivatives.

PART VIII. SUBSTITUTION REACTIONS.

Introduction.
Nucleophilic Aliphatic Substitution.
Electrophilic Aromatic Substitution.
Nuceophilic Aromatic and Vinylic Substitution.
Conclusion.

PART IX. ADDITION REACTIONS.

Introduction.
Addition of Halogens to Alkenes.
Other Addition Reactions.

PART X. ELIMINATION REACTIONS.

Introduction.
Dehydrohalogenation and Related 1,2-Elimination Reactions.
Other 1,2-Elimination Reactions.

PART XI. CONCERTED REACTIONS.

Introduction.
Electrocyclic Transformations.
Sigmatropic Reactions.
Cycloaddition Reactions.
Other Concerted Reactions.
A Generalized Selection Rule for Pericyclic Reactions.
Alternative Conceptual Models for Concerted Reactions.

PART XII. PHOTOCHEMISTRY.

Introduction.
Properties of Excited States.
Representative Photochemical Reactions.
Some Applications of Organic Photochemistry.

References for Problems.
Indices.