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Chapter 1 Introduction of Experimental Organic Chemistry1
1.1The Role of Experimental Organic Chemistry1
1.2General Rules for the Organic Chemistry Experiments2
1.3Safety in the Organic Chemistry Laboratory3
1.4Pre-lab Reports£¬Notebooks and Lab Reports in the Laboratory8
1.5Common Laboratory Glassware and Equipment15
1.6The Literature of Organic Chemistry18
1.7Green Chemistry in the Organic Laboratory21 Chapter 2 Basic Operations of Organic Chemistry Experiments25
2.1Heating and Cooling25
2.2Drying Organic Solutions and Solids28
2.3Filtration31
2.4Simple Distillation and Boiling Point33
2.5Fractional Distillation36
2.6Steam Distillation38
2.7Vacuum Distillation41
2.8Extraction and Washing44
2.9Recrystallization48
2.10Sublimation53
2.11Measurement of the Melting Point55
2.12Refluxing58
2.13Stirring Methods61
2.14Water-free and Air-free Operation62
2.15Chromatography Techniques64 Chapter 3 Fundamental Experiments80
3.1Unsaturated Hydrocarbons80
Exp.1Preparation of Cyclohexene80
Exp.2Preparation of Phenylacetylene82
3.2Alkyl Halides85
Exp.3Preparation of 1-Bromobutane85
Exp.4Preparation of 2-Chloro-2-methylbutane89
3.3Alcohols,Phenols and Ethers92
Exp.5Preparation of 2-Methyl-2-butanol92
Exp.6Preparation of Triphenylmethanol96
Exp.7Preparation of Di-n-butyl Ether100
Exp.8Preparation of Ethyl Phenyl Ether103
Exp.9Preparation of o-tert-Butylhydroquinone106
3.4Aldehydes and Ketones109
Exp.10Preparation of Cyclohexanone109
Exp.11Preparation of Acetophenone112
Exp.12Preparation of Benzaldehyde115
3.5Carboxylic Acids118
Exp.13Preparation of Benzoic Acid118
Exp.14Preparation of Cinnamic Acid121
Exp.15Preparation of Hexane-1,6-dionic Acid124
3.6Carboxylic Acid Derivatives127
Exp.16Preparation of Ethyl Acetate127
Exp.17Preparation of n-Dibutyl Phthalate130
3.7Nitrogen-containing Compounds133
Exp.18Preparation of Acetanilide133
Exp.19Preparation of Methyl Orange135
3.8Heterocyclic Compounds138
Exp.20Preparation of 8-Hydroxyquinoline138
Exp.21Extraction and Separation of Caffeine from Tea Leaves141 Chapter 4 Comprehensive Experiments14
4Exp.1Preparation of Benzyl Alcohol and Benzoic Acid144
Exp.2Preparation of Benzil and Thin-layer Chromatography147
Exp.3Preparation of Acetylferrocene and Column Chromatography150
Exp.4Preparation of Ethyl Acetoacetate by the Claisen Condensation Reaction154
Exp.5Synthesis and Characterization of Aspirin157
Exp.6Multi-step Synthesis of Sulfanilamide161
Exp.7A Solvent Free Cannizzaro Reaction and Thin-layer Chromatography166
Exp.8Preparation of 4-Vinylbenzoic Acid by a Wittig Reaction169
Exp.9Preparation of Dimedone via the Robinson Annulation172
Exp.10Preparation of Cinnamic Acid by the Knoevenagel Condensation175
Exp.11Microwave-assisted Preparation of Benzoic Acid and Ethyl Benzoate178 Chapter 5 Experiments from Research and Literature183
Exp.1Synthesis of 3-Substituted Isoindolin-1-ones by Solvent-free Grinding Reaction183
Exp.2Electroorganic Synthesis of Nitriles185
Exp.3Ultrasonic Assisted Green Protocol for the Synthesis of N,N′-bis Phenylsulfamide187
Exp.4Clean Synthesis in Water:Uncatalysed Preparation of Ylidenemalononitriles188
Exp.5Transition-metal-catalyzed Convenient Synthesis of Internal Alkyne190
Exp.6N-Heterocyclic Carbene Catalyzed Intramolecular Benzoin Condensation to Access 9,10-Phenanthraquinone192
Exp.7Optical Resolution of (±)-(S)-Methyl-(S)-phenylsulfoximine with ( )-L-Camphorsulfonic Acid194
Exp.8Synthesis of Benzyl Acetate in Room Temperature Ionic Liquids197
Exp.9Green Synthesis of 4-Bromoaniline200
Exp.10Pinacol Rearrangement and Photochemical Synthesis of Benzopinacol204 Chapter 6 Study Guide of Some Typical Experiments207
Exp.1Preparation of Cyclohexene (Miniscale Reaction)207
Exp.2Preparation of 1-Bromobutane209
Exp.3Preparation of Acetyl Ferrocene and Column Chromatography212
Exp.4Preparation of Acetylaniline 215
Exp.5Preparation of 2-Methyl-2-butanol217
Exp.6Preparation of Benzil and Thin-layer Chromatography220
Exp.7Preparation of Cinnamic Acid223
Exp.8Preparation of Benzoic Acid and Ethyl Benzoate225
Exp.9Preparation of Benzoic Acid and Benzyl Alcohol229 Appendix 232 References235