Multiscale Operational Organic Chemistry

John W. Lehman received his Ph.D. in chemistry from the University of Colorado in Boulder. He has taught chemistry for 35 years at Lake Superior State University, a small university in Michigan's scenic Upper Peninsula. In recognition of his teaching skills, he received the State of Michigan's Teaching Excellence Award in 1990. In 2001 he funded a chemistry scholarship to help bring outstanding students into the chemistry program at Lake Superior State University. His groundbreaking lab text, Operational Organic Chemistry, was first published in 1981, and he has written three additional books for the organic chemistry laboratory.

• Preface To the Instructor Acknowledgments  Introduction Problem Solving in the Organic Chemistry Laboratory Scientific Methodology Organization of This Book A Guide to Success in the Organic Chemistry Lab  Laboratory Safety Safety Standards Protecting Yourself Preventing Laboratory Accidents Reacting to Accidents: First Aid Reacting to Accidents: Fire Chemical Hazards Finding and Using Chemical Safety Information  Chemistry and the Environment Disposal of Hazardous Wastes Green Chemistry  Part I Mastering the Operations 1. Learning Basic Operations. The Effect of pH on a Food Preservative 2. Extraction and Evaporation. Separating the Components of “Panacetin” 3. Recrystallization and Melting-Point Measurement. Identifying a Constituent of “Panacetin” 4. Heating Under Reflux. Synthesis of Salicylic Acid from Wintergreen Oil 5. Simple Distillation, Gas Chromatography. Preparation of Synthetic Banana Oil 6. Fractional Distillation. Separation of Petroleum Hydrocarbons 7. Addition, Sublimation. A Green Synthesis of Camphor 8. Boiling Point, Refractive Index. Identification of a Petroleum Hydrocarbon 9. Column Chromatography, UV-VIS Spectrometry. Isolation and Isomerization of Lycopene from Tomato Paste10. Steam Distillation, Infrared Spectrometry. Isolation and Identification of the Major Constituent of Clove Oil11. Thin-Layer Chromatography, NMR Spectrometry. Identification of Unknown Ketones 12. Vacuum Distillation, Optical Rotation. The Optical Activity of a-Pinene: A Chemical Mystery  Part II Correlated Laboratory Experiments 13. Investigation of a Chemical Bond by Infrared Spectrometry 14. Properties of Common Functional Groups 15. Thin-Layer Chromatographic Analysis of Drug Components 16. Separation of an Alkane Clathrate 17. Isomers and Isomerization Reactions 18. Structures and Properties of Stereoisomers 19. Bridgehead Reactivity in an SN1Solvolysis Reaction 20. Reaction of Iodoethane with Sodium Saccharin, an Ambident Nucleophile 21. Dehydration of Methylcyclohexanols and the Evelyn Effect 22. Testing Markovnikov’s Rule 23. Stereochemistry of Bromine Addition to trans-Cinnamic Acid 24. A Green Synthesis of Adipic Acid 25. Preparation of Bromotriphenylmethane and the Trityl Free Radical 26. Chain-Growth Polymerization of Styrene and Methyl Methacrylate 27. Synthesis of Ethanol by Fermentation 28. Reaction of Butanols with Hydrobromic Acid 29. Borohydride Reduction of Vanillin to Vanillyl Alcohol 30. Synthesis of Triphenylmethanol and the TritylCarbocation 31. An Unexpected Reaction of 2,3-Dimethyl-2,3-butanediol 32. Identification of a Conjugated Diene from Eucalyptus Oil 33. Spectral Identification of Monoterpenes 34. Synthesis and Spectral Analysis of Aspirin 35. Directive Effects in the Bromination of Vanillin 36. Mechanism of the Nitration of Arenes by Nitronium Fluoborate 37. Friedel–Crafts Acylation of Anisole 38. Determination of the Structure of a Natural Product in Anise Oil 39. Identification of an Oxygen-Containing Organic Compound 40. Oxidation of the Insect Repellent “6-12” 41. Isomerization of a Cyclic Ketone 42. A Wittig Reaction of trans-Cinnamaldehyde43. Effect of Reaction Conditions on the Condensation of Furfural with Cyclopentanone 44. Electronic Effect of a para-Iodo Substituent 45. Synthesis and Identification of an Unknown Carboxylic Acid 46. Preparation of the Insect Repellent N,N-Diethyl-metatoluamide47. Synthesis of Dimedone and Measurement of Its Tautomeric Equilibrium Constant 48. Preparation of Para Red and Related Azo Dyes 49. Reaction of Phthalimide with Sodium Hypochlorite 50. Identification of an Unknown Amine 51. Preparation and Mass Spectrum of 2-Phenylindole 52. Nucleophilic Strength and Reactivity in SNAr Reactions 53. Structure of an Unknown D-Hexose 54. Fatty Acid Content of Commercial Cooking Oils 55. Structure of an Unknown Dipeptide 56. Multistep Synthesis of Benzilic Acid from Benzaldehyde 57. Using the Chemical Literature in an Organic Synthesis 58. A Research Project in Organic Chemistry  Part III Minilabs1. Making Useful Laboratory Items 2. Extraction of Iodine by Dichloromethane 3. Purification of an Unknown Compound by Recrystallization 4. Developing and Testing a Hypothesis 5. Preparation of Acetate Esters 6. Gas Chromatographic Analysis of Commercial Xylene 7. Isolation of an Expectorant from Cough Capsules 8. A Missing-Label Puzzle 9. Paper Chromatography of Dyes in Commercial Drink Mixes 10. Gas Chromatographic Analysis of an Essential Oil from Orange Peel 11. Identification of an Unknown Felt-Tip Pen Ink by TLC 12. Optical Rotation of Turpentine 13. The Structures of Organic Molecules 14. Who Else Has My Compound? 15. Isomers and Molecular Structure 16. Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions 17. An SN1 Reaction of Bromotriphenylmethane 18. Preparation and Properties of a Gaseous Alkene 19. Addition of Iodine to a-Pinene 20. Unsaturation in Commercial Products 21. Free-Radical Stability 22. The Nylon Rope Trick 23. Nucleophilic Substitution Rates of Alcohols 24. Photoreduction of Benzophenone 25. Oxidation of Alcohols by Potassium Permanganate 26. Preparation of a Fluorescent Dye 27. Diels–Alder Reaction of Maleic Anhydride and Furan 28. Identification of an Unknown Arene by NMR Spectrometry 29. Interpretation of a Mass Spectrum 30. Nitration of Naphthalene 31. Preparation of Carbocations by the Friedel–Crafts Reaction 32. Air Oxidation of Fluorene to 9-Fluorenone 33. A Nucleophilic Addition–Elimination Reaction of Benzil 34. Preparation of Aldol Condensation Products 35. A Spontaneous Reaction of Benzaldehyde 36. Acid–Base Strengths of Organic Compounds 37. Hydrolysis Rates of Esters 38. Preparation of Benzamide 39. Synthesis of Dimedone Derivatives of Benzaldehyde 40. A Diazonium Salt Reaction of 2-Aminobenzoic Acid 41. Beckmann Rearrangement of Benzophenone Oxime 42. Dyeing with Indigo 43. Reactions of Monosaccharides with Phenols 44. Isolation of Trimyristin from Nutmeg 45. Preparation of a Soap Using a Phase-Transfer Catalyst 46. Isolation of a Protein from Milk  Part IV Qualitative Organic AnalysisAn Overview of Qual Organic  Preliminary Work Purification Measurement of Physical Constants Physical Examination Ignition Test  Classification Solubility Tests Classification Tests  Spectral Analysis Infrared Spectra NMR Spectra  Identification List of Possibilities Additional Tests and Data Preparation of Derivatives Report  Exercises  Part V Laboratory OperationsA) Basic Operations 1. Cleaning and Drying Glassware 2. Using Specialized Glassware 3. Using Glass Rod and Tubing 4. Weighing 5. Measuring Volume 6. Making Transfers  B) Operations for Conducting Chemical Reactions 7. Heating 8. Cooling 9. Temperature Monitoring 10. Mixing 11. Addition of Reactants 12. Excluding Water from Reaction Mixtures 13. Excluding Air from Reaction Mixtures 14. Trapping Gases  C) Separation Operations 15. Gravity Filtration 16. Vacuum Filtration 17. Centrifugation 18. Extraction 19. Evaporation 20. Steam Distillation 21. Column Chromatography 22. Thin-Layer Chromatography 23. Paper Chromatography  D) Washing and Drying Operations 24. Washing Liquids 25. Drying Liquids 26. Washing and Drying Solids 27. Cleaning and Drying Gases  E) Purification Operations 28. Recrystallization 29. Sublimation 30. Simple Distillation 31. Vacuum Distillation 32. Fractional Distillation  F) Measuring Physical Constants 33. Melting Point 34. Boiling Point 35. Refractive Index 36. Optical Rotation  G. Instrumental Analysis 37. Gas Chromatography 38. High-Performance Liquid Chromatography39. Infrared Spectrometry 40. Nuclear Magnetic Resonance Spectrometry41. Ultraviolet–Visible Spectrometry 42. Mass Spectrometry  Appendixes and BibliographyI Laboratory Equipment II Keeping a Laboratory Notebook III Writing a Laboratory Report IV Calculations for Organic Synthesis V Planning an ExperimentVI Properties of Organic Compounds VII The Chemical Literature  Bibliography Index