Organicum

Preface to the First German EditionPreface to the Fifth German EditionPreface to the First English EditionA. Introduction to Laboratory Technique 1. Means and Methods for the Performance of Organic Chemical Reactions 1.1. Types of Glass and Glass Joints 1.2. Vessels 1.3. Condensers 1.4. Standard Apparatus for Organic Reactions 1.5. Stirring and Shaking 1.6. Metering and Introduction of Gases 1.7. Heating and Cooling 1.8. Working Under Pressure 1.9. Working Under Reduced Pressure 1.10. Drying 2. Separating Processes 2.1. Filtration and Centrifuging 2.2. Crystallization 2.3. Distillation and Rectification 2.4. Sublimation 2.5. Extraction and Distribution or Partition 2.6. Adsorption and Adsorption Chromatography 3. The Determination of the Physical Properties of Organic Compounds 3.1. Melting Point 3.2. Boiling Point 3.3. Density 3.4. Refractometry 3.5. Polarimetry 3.6. Absorption Spectroscopy 4. Storage of Chemicals, Destruction of Dangerous Wastes 4.1. Storage of Chemicals 4.2. Wastes and their Destruction 5. Basic Equipment 6. Literature ReferencesB. The Literature of Organic Chemistry; Report Writing 1. Reference Literature 2. Periodical Literature 3. Patent Literature 4. Handbooks, Collections of Methods, Progress Reports 5. Books of Tables 6. Textbooks 7. Report Writing 8. Literature ReferenceC. Some General Principles 1. Classification of Organic Chemical Reactions 1.1. According to the Reaction Path 1.2. According to the Nature of the Bond Rearrangement 1.3. According to the Number of Molecules Involved in the Rate-Determining Steps of the Reactions 2. The Acid-Base Concept 3. The Time Factor in Organic Chemical Reactions 3.1. Successive Reactions 3.2. Competing Reactions 4. The Influence of Substituents on the Electron Density Distribution and on the Reactivity of Organic Molecules 4.1. The Distribution of the Electron Density in Organic Molecules 4.2. The Influence of Substituents on the Reactivity of Organic Compounds. The Hammett Equation 5. Literature References 6. AbbreviationsD. Organic Preparative Section On the Use of Experimental Details and Tables 1. Radical Substitution 1.1. Production and Stability of Radicals 1.2. Reactions of Free Radicals. Radical Chain Reactions 1.3. Reactivity and Selectivity in Radical Substitutions 1.4. Detection of Radicals and Indications of Radical Reactions 1.5. Radical Halogenations 1.6. Oxidations with Molecular Oxygen 1.7. Other Radical Substitution Reactions 1.8. Literature References 2. Nucleophilic Substitution on a Saturated Carbon Atom 2.1. General Course and Molecularity of the Reaction 2.2. Factors Affecting the Course of Nucleophilic Substitution Reactions 2.3. Relationship Between Type of Substitution and Substitution Products 2.4. Nucleophilic Substitution in Alcohols and Ethers 2.5. Nucleophilic Substitution in Alkyl Halides and Sulphates and Alkanesulphonates 2.6. Literature References 3. Elimination with the Formation of Multiple C—C Bonds 3.1. Ionic Eliminations 3.2. Thermal cis-Eliminations 3.3. Literature References 4. Additions to Non-Activated Multiple C—C Bonds 4.1. Electrophilic Addition to Alkenes and Alkynes 4.2. Nucleophilic Addition 4.3. Radical Addition 4.4. Catalytic Hydrogénation 4.5. Literature References 5. Electrophilic and Nucleophilic Substitution in Aromatics 5.1. Electrophilic Aromatic Substitution 5.2. Nucleophilic Aromatic Substitution 5.3. Literature References 6. Oxidation and Dehydrogenation 6.1. General Features 6.2. Oxidation of Methyl and Méthylène Groups 6.3. Oxidation of Primary and Secondary Alcohols and Aldehydes 6.4. Quinones by Oxidation 6.5. Oxidations with C—C Cleavage 6.6. Dehydrogenation of Hydrocarbons and Hydroaromatics 6.7. Literature References 7. Reactions of Carbonyl Compounds 7.1. Reactions of Carbonyl Compounds with Bases 7.2. Reactions of Carbonyl Compounds with C—H Acidic Compounds 7.3. Reactions of Carbonyl Compounds with Cryptobases 7.4. Reactions of Vinylogous Carbonyl Compounds 7.5. Literature References 8. Reactions of other Hetero-Analogous Carbonyl Compounds 8.1. Reduction of Nitro Compounds and Nitroso Compounds 8.2. Reactions of Nitrous Acid 8.3. Reactions of the Diazonium Salts 8.4. Some Reactions of Aliphatic Diazo Compounds 8.5. Reactions of Sulphonic Acid Derivatives 8.6. Literature References 9. Rearrangements 9.1. Nucleophilic 1,2-Rearrangements 9.2. Aromatic Rearrangements 9.3. Literature ReferencesE. The Identification of Organic Substances 1. Preliminary Tests and Detection of Functional Groups 1.1. Preliminary Tests 1.2. Testing for Functional Groups 2. Preparation of Derivatives 2.1. Ethers 2.2. Aldehydes and Ketones 2.3. Alcohols 2.4. Amines 2.5. Amino-Acids 2.6. Carboxylic Acids 2.7. Amides and Nitriles 2.8. Carboxylic Acid Esters 2.9. Halogenohydrocarbons 2.10. Hydrocarbons 2.11. Nitro and Nitroso Compounds 2.12. Thiols and Thiophenols 2.13. Phenols 2.14. Sulphonic Acids 3. Separation of Mixtures 4. Problems for Practice 5. Literature References 6. Tables for the Characterization of Organic CompoundsF. Properties, Purification, and Preparation of Important Reagents, Solvents, and Auxiliaries (Reagent Appendix)G. The Toxieity of Important ChemicalsAppendix to Organicum Review of Common Methods for the Preparation of Important Classes of Compounds (Method Index)Index