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T H E MECHANISM OF HOMOGENEOUS O R G A N I C R E A C T I O N S FROM T H E PHYSICAL-CHEMICAL S T A N D P O I N T BY
FRANCIS OWEN R I C E ASSOCIATE PROFESSOR OF CHEMISTRY IN THE JOHNS HOPKINS UNIVERSITY
A. C. S. M O N O G R A P H NO. 39 TABLE OF CONTENTS CHAPTER I CHAPTER II
CHAPTER VII
INTRODUCTION REACTION VELOCITY
Orders of Reactions—Simultaneous Reactions— Opposing' Reactions—Consecutive Reactions— Side Reactions—Analytical Procedure—Errors of Measurement—Reaction Velocity and Temperature—Mechanism of Organic Reactions— Summary CHAPTER I I I
ADDITION COMPOUND FORMATION
Existence of Addition Compounds—Measurement of Compound Formation—Chemical Constitution and Addition Compound Formation— Double Compound Formation and Ionization—Electronic Theory and Complex Compounds—Catalytic Activity and Double Compound Formation—Carbonyl Chloride as Solvent—Interpretation of Freezing Point Data— Double Compound Formation with Alurninium Chloride—Double Compounds with Other Metallic Haiides CHAPTER IV
THEORETICAL
Arrhenius Hypothesis — Radiation Hypothesis — Skrabal's Hypothesis — Activity Hypothesis — Dry Hydrogen Ion Hypothesis — Catalysis CHAPTER V
ISOMERIC CHANGE
Nitrocamphor—Keto-Enol Isomerism—Analysis of Keto-Enol Mixtures—Keto-Enol Equilibrium—Ferric Chloride Reaction—Benzoyl Acetoacetic Ester—Malonic Ester—Structure and Keto-Enol Equilibrium—Solvent and KetoEnol Equilibrium—Temperature and KetoEnol Equilibrium—Isolation of Keto-Enol Isomers—Catalysis in Keto-Enol Change—Reactions of Keto-Enol Isomers—Halogenation of Keto-Enol Isomers—Geometric Isomers—Acetylchloroaminobenzene CHAPTER VI
HYDROLYTIC REACTIONS
Hydration of Acid Anhydrides—Lactones— Ester Hydrolysis—Complex Formation in Ester Hydrolysis—Esters of Strong Acids—Substitution and Rate of Hydrolysis—Hydrolysis of Amides—Hydrolysis of Sucrose—Esterification About 225 Pages
ALIPHATIC HYDROCARBONS
Halogenation of Paraffin Hydrocarbons—Oxidation of Paraffin Hydrocarbons—Other Reactions of Paraffin Hydrocarbons—Halogenation of Ethylene—Halogenation of Ethylene Linkage—Addition of Halogen Acids to Ethylene Linkage—Ethylene and Halogens in Aqueous Solution—Oxidation of the Ethylene Linkage—Nitration of Unsaturated Aliphatic Hydrocarbons—Sulfonation of Ethylene—Hydration of Acetylene CHAPTER VIII REACTIONS OF BENZENE AND DERIVATIVES
Physical Properties and Directive Influence— Substitution in Benzene Derivatives—Temperature and Benzene Substitution—Solvent and Benzene Substitution—Catalysts and Benzene Substitution—-Chlorination of Benzene— Reactions of Disubstituted Benzene Derivatives—Analysis of Mixtures of Isomers—Bromination of Benzene Derivatives—Other Studies of Directive Influence—Sulfonation of Aromatic Compounds—Nitration of Aromatic Hydrocarbons—Nitration of Phenol—Nitration of Other Aromatic Compounds CHAPTER IX
GENERAL REACTIONS
Friedel and Crafts Reaction-1—Acetal Formation—Condensation of Aldehydes to Esters— Other Reactions of Aldehydes—Cannizzaro's Reaction—Condensation of Benzaldehyde to Benzoin—Transformation of Benzil to Benzilic Acid—Preparation o f Hydroxy Aldehydes— The Perkin Condensation—The Claisen Condensation—The Michael Reaction—Hoesch's Synthesis—The Hell-Volhard Reaction
CHAPTER X
SPECIAL TOPICS
The Walden Inversion—The Beckmann Inversion—Other Molecular Rearrangements— The Mechanism of Halogenation—Structure and Chemical Reactivity—Chemical Reactivity in the Acetal Reaction—Chemical Reactivity of Alcohols—Chemical Reactivity of Haiides— Chemical Reactivity of Ketones—Chemical Reactivity of Cyclic Acetals—Homogeneous Gas Reactions
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