Lab Manual for Organic Chemistry: A Short Course

Description

The Laboratory Manual, with the assistance of co-author T.K. Vinod at Western Illinois University, includes an experiment on green chemistry, pre-laboratory exercises, and safety instructions. Contents Preface Introduction: To the Student Experiment 1: Melting Point Determination: Purity and Identity of Crystalline Organic Compounds 1: How are Melting Points Used? 2: General Technique for Melting Point Determination 3: Objectives of the Experiment 4: The Melting Point Apparatus and Tubes 5: Determination of Melting Points 6: Identification of an Unknown Prelab Exercise Experiment 1 Lab Report Experiment 1 Experiment 2: Recrystallization: Purification of Crystalline Organic Compounds 1: General Principles 2: Apparatus for Hot Filtration and Vacuum Filtration 3: Reflux Apparatus 4: Recrystallization of Acetanilide 5: Recrystallization of p-Dibromobenzene Prelab Exercise Experiment 2 Lab Report Experiment 2 Experiment 3: Distillation: Separation and Purification of Organic Liquids 1: General Principles 2: Objectives of This Experiment 3: Distillation of Hexane 4: Separation of a Binary Mixture by Simple Distillation 5: Separation of a Binary Mixture by Using a Fractionating Column Prelab Exercise Experiment 3 Lab Report Experiment 3 Experiment 4: Extraction: A Separation and Isolation Technique 1: General Principles 2: Practical Considerations 3: Use of the Separatory Funnel 4: Separation of a Three-Component Mixture by Extraction Prelab Exercise Experiment 4 Lab Report Experiment 4 Experiment 5: Isolation of Natural Products: Caffeine and Eugenol Part A. Caffeine (Extraction and Sublimation) Part B. Eugenol (Steam Distillation) Prelab Exercise Experiment 5 Lab Report Experiment 5 Experiment 6: Chromatography: Column, Thin-Layer, Gas-Liquid, and Paper Part A. Column Chromatography Part B. Thin-Layer Chromatography (TLC) Part C. Gas-Liquid Chromatography (GLC) Part D. Paper Chromatography Prelab Exercise Experiment 6 Lab Report Experiment 6 Experiment 7: Conformations of Alkanes and Cycloalkanes: An Exercise with Molecular Models and Computer Modeling The Models Definitions Part A. The Conformations of Acyclic Molecules Part B. The Conformations of the Cyclohexane Ring Part C. Computer Modeling: Conformations of Acyclic Molecules Part D. Computer Modeling: Conformations of the Cyclohexane Ring Prelab Exercise Experiment 7 Lab Report Experiment 7 Experiment 8: Preparation of Alkenes from Cyclohexanol or 2-Methyl-2-butanol, and Tests for Unsaturation Part A. Cyclohexene from Cyclohexanol Part B. Dehydration of 2-Methyl-2-butanol Part C. Tests for Unsaturation Prelab Exercise Experiment 8 Lab Report Experiment 8 Experiment 9: Cis-Trans Isomerism in Alkenes: Models and Experiments Principles Part A. Cis-Trans Isomerism Illustrated with Models Part B. The Interconversion of Cis-Trans Isomers Prelab Exercise Experiment 9 Lab Report Experiment 9 Experiment 10: Cycloadditions: The Diels-Alder Reaction Part A. The Cyclopentadiene-Maleic Anhydride Adduct Part B. The 1,3-Butadiene-Maleic Anhydride Adduct Part C. The Cyclopentadiene-1,4-Benzoquinone Adduct Prelab Exercise Experiment 10 Lab Report Experiment 10 Experiment 11: Electrophilic Aromatic Substitution 1: General Principles Part A. Directing Effects of Benzene Ring Substituents Part B. Activating Power of Benzene Ring Substituents Prelab Exercise Experiment 11 Lab Report Experiment 11 Experiment 12: Stereoisomerism: Principles Illustrated with Molecular Models, Computer Modeling and Experiments Part A. Principles Illustrated with Models Part B. Principles Illustrated with Computer Models Part C. Special Behavior of Chiral Meolecules Prelab Exercise Experiment 12 Lab Report Experiment 12 Experiment 13: Alkyl Halides: Structure and Reactivity in Nucleophilic Substitutions Part A. Preparation of Alkyl Halides from Alcohols Part B. Reactivity of Halides toward Silver Nitrate Part C. Reactivity of Halides toward Sodium Iodide Prelab Exercise Experiment 13 Lab Report Experiment 13 Experiment 14: The Hydroxyl Group: Reactions of Alcohols and Phenols 1: Solubility in Water 2: Reaction with Sodium (Optional) 3: The Lucas Test 4: The Bordwell-Wellman Test 5: Esters 6: The Acidity of Phenols 7: Reaction of Phenol with Bromine Water 8: Reaction of Phenols and Enols with Ferric Chloride Prelab Exercise Experiment 14 Lab Report Experiment 14 Experiment 15: Reactions of Aldehydes and Ketones Part A. Oxidation Part B. Addition Reactions Part C. Reactions of Enolate Anions Part D. An Unknown Prelab Exercise Experiment 15 Lab Report Experiment 15 Experiment 16: Oxidation of Alcohols and Reduction of Ketones Part A. Oxidation Part B. Reduction Prelab Exercise Experiment 16 Lab Report Experiment 16 Experiment 17: Oxidation of Aldehydes to Carboxylic Acids: A Green Chemistry Experiment Preparation of Benzoic Acid Prelab Exercise Experiment 17 Lab Report Experiment 17 Experiment 18: Two Ways to Synthesize a Carboxylic Acid Part A. The Grignard Method Part B. Hydrolysis of a Nitrile Prelab Exercise Experiment 18 Lab Report Experiment 18 Experiment 19: Reactions of Carboxylic Acids and Their Derivatives Part A. Carboxylic Acid Salts Part B. Acyl Halides and Acid Anhydrides Part C. Esters Part D. Amides Prelab Exercise Experiment 19 Lab Report Experiment 19 Experiment 20: Esters: Synthesis and Saponification of Methyl Benzoate Part A. Synthesis of Methyl Benzoate Part B. Saponification of Methyl Benzoate Prelab Exercise Experiment 20 Lab Report Experiment 20 Experiment 21: Synthesis of Aspirin (Acetylsalicylic Acid) Prelab Exercise Experiment 21 Lab Report Experiment 21 Experiment 22: Amines and Diazonium Compounds Part A. Preparation of a Primary Aromatic Amine Part B. Reactions of Amines Part C. Preparation and Reactions of Diazonium Compounds Prelab Exercise Experiment 22 Lab Report Experiment 22 Experiment 23: Preparation of Sulfanilamide: A Multistep Synthesis 1: Sulfa Drugs 2: Plan of the Synthesis 3: Synthesis of Sulfanilamide Prelab Exercise Experiment 23 Lab Report Experiment 23 Experiment 24: Dyes and Dyeing 1: Color and Conjugation 2: Dyes and Fabrics 3: Direct, or Substantive, Dyes 4: Mordant Dyes 5: Developed, or Ingrain, Dyes 6: Vat Dyes 7: Phenolphthalein Indicators Prelab Exercise Experiment 24 Lab Report Experiment 24 Experiment 25: Infrared and NMR Spectroscopy 1: Introduction 2: Instrumentation 3: Sample Preparation Part A. Infrared Spectroscopy Part B. NMR Spectroscopy Prelab Exercise Experiment 25 Lab Report Experiment 25 Experiment 26: Synthesis of a Heterocycle: 2-Amino-4,6-Dimethylpyrimidine Prelab Exercise Experiment 26 Lab Report Experiment 26 Experiment 27: Storage and Release of Light Energy: Benzopinacol and Luminol Part A. Benzopinacol from Benzophenone Part B. Oxidation of Luminol Prelab Exercise Experiment 27 Lab Report Experiment 27 Experiment 28: Synthetic Polymers Part A. Addition (Chain-Growth) Polymers Part B. Condensation (Step-Growth) Polymers Prelab Exercise Experiment 28 Lab Report Experiment 28 Experiment 29: Fats and Oils; Soaps and Detergents Part A. Properties of Glycerides Part B. Preparation of Soap from a Fat Part C. Properties of Soap and Syndets Prelab Exercise Experiment 29 Lab Report Experiment 29 Experiment 30: Reactions of Carbohydrates Part A. Reducing and Nonreducing Carbohydrates Part B. Hydrolysis of Disaccharides and Polysaccharides Part C. Cellulose Acetate Prelab Exercise Experiment 30 Lab Report Experiment 30 Experiment 31: Amino Acids and Proteins Part A. Solubility and Amphoteric Properties Part B. Reaction with Nitrous Acid Part C. The Biuret Test Part D. The Xanthoproteic Test Part E. Derivatives of Amino Acids Part F. Protein Composition Prelab Exercise Experiment 31 Lab Report Experiment 31 Appendices Appendix A. Some Useful Atomic Weights Appendix B. Boiling Points and Densities of Some Common Organic Liquids Appendix C. Concentrations of Common Reagents Appendix D. Preparation of Special Reagents Appendix E. Chemicals Required for Each Experiment Appendix F. Suggested Equipment for Each Student Index