Chapter 1 Introduction 1
1.1 General Rules for Organic Chemistry Laboratory 1
1.2 Safe Laboratory Practice and First Aid in Case of an Accident 2
1.2.1 Prevention of Fires and First Aid in Case of a Fire 2
1.2.2 Prevention of Explosions 3
1.2.3 First Aid for Cuts and Scalds 3
1.2.4 Prevention of Damages from Hazardous Chemicals and First Aid for Chemical Burns 3
1.2.5 Toxicity and Safety Data of Chemicals 4
1.2.6 Disposal of Chemical Wastes 7
1.3 Information Sources for Experimental Organic Chemistry 8
1.3.1 Important Handbooks and Dictionaries 8
1.3.2 Important Journals Involving Organic Experiment 9
1.3.3 Important Online Resources 10
1.4 Common Glassware and Apparatus 10
1.4.1 Names and Uses of Common Glassware 10
1.4.2 Cleaning and Drying Glassware 14
1.4.3 Common Organic Lab Apparatus 15
1.4.4 Assembling and Disassembling Apparatus 18
1.5 Preparation and Notebook for the Laboratory 21
1.5.1 Laboratory Preparation Note 22
1.5.2 Experimental Record 22
1.5.3 Sample Calculation for Notebook Records 23
1.5.4 Laboratory Notebook Formats 24
1.5.5 Experimental Report 27
Chapter 2 Basic Techniques for Organic Experiments 29
2.1 Working on Glass Tubes 29
2.1.1 Cutting and Bending Glass Tubes 29
2.1.2 Stretching Glass Tubes 30
2.2 Weighing,Measuring and Transferring Reagents 31
2.2.1 Measuring and Transferring Liquids 31
2.2.2 Weighing Methods 33
2.3 Heating,Cooling and Stirring Methods 34
2.3.1 Heating Methods and Precautions 34
2.3.2 Cooling Methods and Coolants 36
2.3.3 Stirring Methods and Equipment 36
2.4 Extraction 38
2.4.1 Liquid-Liquid Extraction 38
2.4.2 Liquid-Solid Extraction 39
2.5 Drying and Drying Agents 40
2.5.1 Drying Organic Liquids 40
2.5.2 Drying Solids 43
2.6 Gas Traps 43
2.7 Separating and Purifying Liquid Compounds 44
2.7.1 Simple Distillation 44
2.7.2 Fractional Distillation 47
2.7.3 Vacuum Distillation 49
2.7.4 Steam Distillation 54
2.8 Separating and Purifying Solid Compounds 56
2.8.1 Filtration Apparatus and Techniques 56
2.8.2 Centrifugation and Decanting Solutions 59
2.8.3 Evaporating Solvents 59
2.8.4 Decolorizing Carbon 60
2.8.5 Recrvstallization 61
2.8.6 Sublimation 63
2.9 Chromatography 64
2.9.1 Column Chromatography 65
2.9.2 Thin-Layer Chromatography(TLC) 68
2.9.3 Gas Chromatography(GC) 71
2.9.4 High-Performance Liquid Chromatography(HPLC) 74
2.10 Measuring Physical Constants of Organic Compounds 76
2.10.1 Melting Point 76
2.10.2 Boiling Point 80
2.10.3 Refractive Index 81
2.10.4 Optical Rotation and Specific Rotation 84
2.10.5 Relative Density 86
2.11 Spectroscopic Identification of Organic Compounds 87
2.11.1 Infrared(IR) Spectroscopy 87
2.11.2 Nuclear Magnetic Resonance(NMR) Spectroscopy 93
2.11.3 Ultra-Violet-Visible(UV-Vis) Spectroscopy 98
2.12 Manipulation Techniques for Air-Sensitive Compounds 101
2.12.1 General Introduction 101
2.12.2 Basic Techniques for Handling Air-Sensitive Compounds 102
Chapter 3 Basic Experiments 104
3.1 Simple and Fractional Distillations:Separation of a Cyclohexane-Toluene Mixture（环己烷－甲苯混合物） 104
3.2 Intramolecular Dehydration of Alcohols:Preparation of Cyclohexene（环己烯） 108
3.3 Intermolecular Dehydration of Alcohols:Preparation of Dibutyl Ether（正丁醚） 113
3.4 The SN2 Reaction:Preparation of 1-Bromobutane（1－溴丁烷） 118
3.5 Decarboxylation of Dicarboxylic Acids:Preparation of Cyclopentanone（环戊酮） 123
3.6 Oxidation of Secondary Alcohols to Ketones:Preparation of Cyclohexanone（环己酮） 126
3.7 Oxidation of Primary Alcohols to Aldehydes:Preparation of Benzaldehyde（苯甲醛） 131
3.8 Fischer Esterification of Carboxylic Acids:n-Butyl Acetate（乙酸正丁酯） 134
3.9 Acetylation of Salicylic Acid:Preparation of Acetylsalicylic Acid（乙酰水杨酸） 140
3.10 Amidation of Carboxylic Acids:Preparation of Acetanilide（乙酰苯胺） 143
3.11 Friedel-Crafts Reaction:Preparation of Acetophenone（苯乙酮） 148
3.12 The Claisen Ester Condensation:Preparation of Ethyl Acetoacetate（乙酰乙酸乙酯） 154
3.13 Perkin Condensation:Preparation of Cinnamic Acid（肉桂酸） 160
3.14 Cannizzaro Reaction:Preparation of Benzyl Alcohol（苯甲醇）and Benzoic Acid（苯甲酸） 166
3.15 Carbene Additions with Phase-Transfer Catalysis:Preparation of 7,7-Dichlorobicyclo［4.1.0］heptane（7，7－二氯双环［4.1.0］庚烷） 170
3.16 Nitration Reaction:Preparation of p-Nitroaniline（对硝基苯胺） 175
3.17 Skraup Reaction:Preparation of Quinoline（喹啉） 179
3.18 Electrochemical Synthesis:Preparation of Iodoform（碘仿） 184
3.19 Extraction:Isolation of Caffeine from Tea Leaves 186
3.20 Thin-Layer and Column Chromatography:Isolation of a Red Pigment from Red Chilli 190
Chapter 4 Comprehensive Experiments 193
4.1 Preparation of 5-n-Butylmalonyl Urea（5-n-Butylbarbituric Acid，正丁基巴比妥酸） 193
4.2 Diels-Alder Reaction:Microwave-Assisted Preparation of 9,10-Dihydroanthracene-9,10-α,β-Succinic Anhydride（9，10－二氢蒽－9，10－α，β－丁二酸酐） 196
4.3 Grignard Reaction:Preparation of Methyl Triphenylmethyl Ether（甲基三苯甲基醚） 199
4.4 Organometallic Chemistry:Preparation of n-Butyllithium（正丁基锂）and Titration of its Concentration 202
Chapter 5 Self-Designing Experiments 206
5.1 Identification of Functional Compounds 206
5.2 Microwave-Assisted Preparation of Acetaminophenol（醋氨酚） 207
Chapter 6 Investigative Experiments 209
6.1 Studies on Synthetic Conditions for Preparation of Isopentyl Acetate（乙酸异戊酯） 209
6.2 Preparation ofα-and β-D-Glucose Pentaacetates（五乙酸葡萄糖酯） 211
6.3 Preparation of 9,9-Bis(methoxymethyl)fluorene（9，9－双（甲氧基甲基）芴） 212
6.4 Preparation and Resolution of Racemic 1,1'-Bi-2-naphthol（1，1'－联－2－萘酚） 214
References 220
Appendix 221
Index 226
Vocabulary 229
Periodic Table of the Elements 235