Becker / Berger / Domschke Organicum

Practical Handbook of Organic Chemistry
1. Auflage 2013
ISBN: 978-1-4831-4628-7
Verlag: Elsevier Science & Techn.
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, 768 Seiten, Web PDF

Organicum: Practical Handbook of Organic Chemistry focuses on the theory, laboratory practice, and aspects of technical use related to organic chemistry. This book discusses the standard apparatus for organic reactions, heating of inflammable liquids, performance of a simple distillation, and partition chromatography in separating columns. The time factor in organic chemical reactions, distribution of the electron density in organic molecules, and synthesis of ethers from alkoxides or phenoxides are also elaborated. This text likewise covers the mechanism of electrophilic aromatic substitution, quinones from aromatic hydrocarbons, and reduction of carbonyl compounds by means of complex hydrides. Other topics include the reaction with ammoniacal solution of a silver salt, preparation of the dimedone derivatives, and saturated aliphatic hydrocarbons. This publication is suitable for chemists and researchers conducting work in organic chemistry.

Autoren/Hrsg.

Becker, Heinz

Berger, Werner

Domschke, Günter

Inhaltsverzeichnis

1;Front Cover;1
2;Organicum: Practical Handbook of Organic Chemistry;4
3;Copyright Page;5
4;Table of Contents;6
5;Preface to the First German Edition;18
6;Preface to the Fifth German Edition;19
7;Preface to the First English Edition;20
8;PART A: INTRODUCTION TO LABORATORY TECHNIQUE;22
8.1;Chapter 1. Means and Methods for the Performance of Organic Chemical Reactions;24
8.1.1;1.1. Types of Glass and Glass Joints;24
8.1.2;1.2. Vessels;26
8.1.3;1.3. Condensers;27
8.1.4;1.4. Standard Apparatus for Organic Reactions;30
8.1.5;1.5. Stirring and Shaking;32
8.1.6;1.6. Metering and Introduction of Gases;34
8.1.7;1.7. Heating and Cooling;37
8.1.8;1.8. Working under Pressure;42
8.1.9;1.9. Working under Reduced Pressure;46
8.1.10;1.10. Drying;51
8.2;Chapter 2. Separating Processes;56
8.2.1;2.1. Filtration and Centrifuging;56
8.2.2;2.2. Crystallization;59
8.2.3;2.3. Distillation and Rectification;63
8.2.4;2.4. Sublimation;86
8.2.5;2.5. Extraction and Distribution or Partition;87
8.2.6;2.6. Adsorption and Adsorption Chromatography;101
8.3;Chapter 3. The Determination of the Physical Properties of Organic Compounds;108
8.3.1;3.1. Melting Point;108
8.3.2;3.2. Boiling Point;111
8.3.3;3.3. Density;113
8.3.4;3.4. Refractometry;114
8.3.5;3.5. Polarimetry;115
8.3.6;3.6. Absorption Spectroscopy;117
8.4;Chapter 4. Storage of Chemicals, Destruction of Dangerous Wastes*);133
8.4.1;4.1. Storage of Chemicals;133
8.4.2;4.2. Wastes and their Destruction;135
8.5;Chapter 5. Basic Equipment;136
8.6;Chapter 6. Literature References;138
8.6.1;Handling chemicals; safety†);138
8.6.2;Working with small amounts of substance;138
8.6.3;Distillation and rectification;139
8.6.4;Partition;139
8.6.5;Chromatography;139
8.6.6;Paper chromatography;139
8.6.7;Thin-layer chromatography;139
8.6.8;Gas chromatography;139
8.6.9;Spectroscopy in the visible and UV region;139
8.6.10;IR spectroscopy;140
8.6.11;NMR spectroscopy;140
9;PART B: THE LITERATURE OF ORGANIC CHEMISTRY; REPORT WRITING;142
9.1;Chapter 1. Reference Literature;144
9.2;Chapter 2. Periodical Literature;146
9.3;Chapter 3. Patent Literature;147
9.4;Chapter 4. Handbooks, Collections of Methods, Progress Reports;147
9.5;Chapter 5. Books of Tables;149
9.6;Chapter 6. Textbooks;149
9.6.1;Textbooks of Organic Chemistry;149
9.6.2;Textbooks of Theoretical Organic Chemistry;150
9.6.3;Textbooks of Industrial Organic Chemistry;151
9.7;Chapter 7. Report Writing;151
9.8;Chapter 8. Literature Reference;152
10;PART C: SOME GENERAL PRINCIPLES;154
10.1;Chapter 1. Classification of Organic Chemical Reactions;156
10.1.1;1.1. According to the Reaction Path;156
10.1.2;1.2. According to the Nature of the Bond Rearrangement;156
10.1.3;1.3. According to the Number of Molecules Involved in the Rate-determining Steps of the Reactions;158
10.2;Chapter 2. The Acid-Base Concept;158
10.3;Chapter 3. The Time Factor in Organic Chemical Reactions;161
10.3.1;3.1. Successive Reactions;162
10.3.2;3.2. Competing Reactions;164
10.4;Chapter 4. The Influence of Substituents on the Electron Density Distribution and on the Reactivity of Organic Molecules;165
10.4.1;4.1. The Distribution of the Electron Density in Organic Molecules;165
10.4.2;4.2. The Influence of Substituents on the Reactivity of Organic Compounds. The Hammett Equation;171
10.5;Chapter 5. Literature References;176
10.6;Chapter 6. Abbreviations;177
11;PART D: ORGANIC PREPARATIVE SECTION;178
11.1;On the Use of Experimental Details and Tables;180
11.2;Chapter 1. Radical Substitution;181
11.2.1;1.1. Production and Stability of Radicals;181
11.2.2;1.2. Reactions of Free Radicals. Radical Chain Reactions;184
11.2.3;1.3. Reactivity and Selectivity in Radical Substitutions;186
11.2.4;1.4. Detection of Radicals and Indications of Radical Reactions;189
11.2.5;1.5. Radical Halogenations;189
11.2.6;1.6. Oxidations with Molecular Oxygen;198
11.2.7;1.7. Other Radical Substitution Reactions;201
11.2.8;1.8. Literature References;202
11.3;Chapter 2. Nucleophilic Substitution on a Saturated Carbon Atom;203
11.3.1;2.1. General Course and Molecularity of the Reaction;203
11.3.2;2.2. Factors Affecting the Course of NucleophiHc Substitution Reactions;207
11.3.3;2.3. Relationship between Type of Substitution and Substitution Productsf);214
11.3.4;2.4. Nucleophilic Substitution in Alcohols and Ethers;215
11.3.5;2.5. Nucleophilic Substitution in Alkyl Halides and Sulphates and Alkanesulphonates;225
11.3.6;2.6. Literature References;249
11.4;Chapter 3. Elimination with the Formation of Multiple C–C Bonds;251
11.4.1;3.1. Ionic Eliminations;251
11.4.2;3.2. Thermal cis-Eliminations;274
11.4.3;3.3 Literature References;278
11.5;Chapter 4. Additions to Non-activated Multiple C–C Bonds;280
11.5.1;4.1. Electrophilic Addition to Alkenes and Alkynes;280
11.5.2;4.2. Nucleophilic Addition;307
11.5.3;4.3. Radical Addition;311
11.5.4;4.4. A Catalytic Hydrogenation;317
11.5.5;4.5. Literature References;326
11.6;Chapter 5. Electrophilìc and Nucleophilic Substitution in Aromatics;328
11.6.1;5.1. Electrophilic Aromatic Substitution;330
11.6.2;5.2. Nucleophilic Aromatic Substitution;373
11.6.3;5.3. Literature References;379
11.7;Chapter 6. Oxidation and Dehydrogenation;382
11.7.1;6.1. General Features;382
11.7.2;6.2. Oxidation of Methyl and Méthylène Groups;383
11.7.3;6.3. Oxidation of Primary and Secondary Alcohols and Aldehydes;393
11.7.4;6.4. Quinones by Oxidation;400
11.7.5;6.5. Oxidations with C–C cleavage;405
11.7.6;6.6. Dehydrogenation of Hydrocarbons and Hydroaromatics;411
11.7.7;6.7. Literature References;416
11.8;Chapter 7. Reactions of Carbonyl Compounds;420
11.8.1;7.1. Reactions of Carbonyl Compounds with Bases;422
11.8.2;7.2. Reactions of Carbonyl Compounds with C– H Acidic Compounds;490
11.8.3;7.3. Reactions of Carbonyl Compounds with Cryptobases;535
11.8.4;7.4. Reactions of Vinylogous Carbonyl Compounds;554
11.8.5;7.5. Literature References;566
11.9;Chapter 8. Reactions of other Hetero-analogous Carbonyl Compounds;570
11.9.1;8.1. Reduction of Nitro Compounds and Nitroso Compounds;571
11.9.2;8.2. Reactions of Nitrous Acid;576
11.9.3;8.3. Reactions of the Diazonium Salts;582
11.9.4;8.4. Some Reactions of Aliphatic Diazo Compounds;593
11.9.5;8.5. Reactions of Sulphonic Acid Derivatives;600
11.9.6;8.6. Literature References;605
11.10;Chapter 9. Rearrangements;607
11.10.1;9.1. Nucleophilic 1,2-Rearrangements;607
11.10.2;9.2. Aromatic Rearrangements;626
11.10.3;9.3. Literature References;628
12;PART E: THE IDENTIFICATION OF ORGANIC SUBSTANCES;630
13;Chapter 1. Preliminary Tests and Detection of Functional Groups;632
13.1;1.1. Preliminary Tests;633
13.2;1.2. Testing for Functional Groups;637
14;Chapter 2. Preparation of Derivatives;647
14.1;2.1. Ethers;648
14.2;2.2. Aldehydes and Ketones;648
14.3;2.3. Alcohols;650
14.4;2.4. Amines;652
14.5;2.5. Amino-acids;653
14.6;2.6. Carboxylic Acids;654
14.7;2.7. Amides and Nitriles;655
14.8;2.8. Carboxylic Acid Esters;656
14.9;2.9. Halogenohydrocarbons;657
14.10;2.10. Hydrocarbons;657
14.11;2.11. Nitro and Nitroso Compounds;659
14.12;2.12. Thiols and Thiophenols;659
14.13;2.13. Phenols;660
14.14;2.14. Sulphonic Acids;661
15;Chapter 3. Separation of Mixtures;662
16;Chapter 4. Problems for Practice;662
17;Chapter 5. Literature References;663
18;Chapter 6. Tables for the Characterization of Organic Compounds;664
18.1;Alcohols;664
18.2;Aldehydes;666
18.3;Amines (primary and secondary);668
18.4;Amines (tertiary);670
18.5;Amino-acids;671
18.6;Carbohydrates;673
18.7;Carboxylic Adds;674
18.8;Hal ides (aliphatic);676
18.9;Halides (aromatic);677
18.10;Hal ides (polyhalides);678
18.11;Hydrocarbons (aliphatic and cycloaliphatic);679
18.12;Hydrocarbons (alkenes and alkynes);680
18.13;Hydrocarbons (aromatic);681
18.14;Ketones;682
18.15;Phenols;684
18.16;Quinones;686
18.17;Sulphonic Acids;686
18.18;Thiols and Thiophenols;687
19;PART F: PROPERTIES, PURIFICATION, AND PREPARATION OF IMPORTANT REAGENTS, SOLVENTS, AND AUXILIARIES (REAGENT APPENDIX)†);688
19.1;Literature References;712
20;PART G: THE TOXICITY OF IMPORTANT CHEMICALS†);714
20.1;Review of the Toxicity of Important Laboratory Chemicals;717
21;APPENDIX TO ORGANICUM;720
21.1;Review of Common Methods for the Preparation of Important Classes of Compounds (Methods Index);722
22;Index;732