Introduction to Organic Laboratory Techniques

Part I: INTRODUCTION TO BASIC LABORATORY TECHNIQUES. Experiment 1. Solubility. Experiment 2. Crystallization. Experiment 3. Extraction. Experiment 4. Chromatography. Experiment 5. Simple and Fractional Distillation. Experiment 6. Infrared Spectroscopy and Boiling-Point Determination. Essay: Aspirin. Experiment 7. Acetylsalicylic Acid. Essay: Analgesics. Experiment 8. Acetanilide. Experiment 9. Acetaminophen. Essay: Identification of Drugs. Experiment 10. TLC Analysis of Analgesic Drugs. Essay: Caffeine. Experiment 11. Isolation of Caffeine. Experiment 11A. Isolation of Caffeine from Tea Leaves. Experiment 11B. Isolation of Caffeine from a Tea Bag. Essay: Esters -- Flavors and Fragrances. Experiment 12. Isopentyl Acetate (Banana Oil). Experiment 13. Methyl Salicylate (Oil of Wintergreen). Essay: Terpenes and Phenylpropanoids. Experiment 14. Isolation of Eugenol from Cloves. Essay: Stereochemical Theory of Odor. Experiment 15. Spearmint and Caraway Oil: (+)- and (-)- Carvones. Essay: The Chemistry of Vision. Experiment 16. Isolation of Chlorophyll and Carotenoid Pigments from Spinach. Essay: Ethanol and Fermentation Chemistry. Experiment 17. Ethanol from Sucrose. Part II: INTRODUCTION TO MOLECULAR MODELING. Essay: Molecular Modeling and Molecular Mechanics. Experiment 18. An Introduction to Molecular Modeling. Experiment 18A. The Conformations of n-Butane: Local Minima. Experiment 18B. Cyclohexane Chair and Boat Conformations. Experiment 18C. Substituted Cyclohexane Rings. Experiment 18D. cis- and trans-2-Butene. Essay: Computational Chemistry -- Ab initio and Semiempirical Methods. Experiment 19. Computational Chemistry. Experiment 19A. Heats of Formation: Isomerism, Tautomerism, and Regioselectivity. Experiment 19B. Heats of Reactions: SN1 Reaction Rates. Experiment 19C. Density-Electrostatic Potential. Maps -- Acidities of Carboxylic Acids. Experiment 19D. Density -- Electrostatic Potential Maps: Carbocations. Experiment 19E. Density -- LUMO Maps: Reactivities of Carbonyl Groups. Part III: PROPERTIES AND REACTIONS OF ORGANIC COMPOUNDS. Experiment 20. Reactivities of Some Alkyl Halides. Experiment 21. Nucleophilic Substitution Reactions: Competing Nucleophiles. Experiment 21A. Competing Nucleophiles with 1-Butanol or 2-Butanol. Experiment 21B. Competing Nucleophiles with 2-Methyl-2-Propanol. Experiment 21C. Analysis. Experiment 22. Hydrolysis of Some Alkyl Chlorides Experiment 23. Synthesis of n-Butyl Bromide and t-Pentyl Chloride. Experiment 23A. n-Butyl Bromide. Experiment 23B. t-Pentyl Chloride. Experiment 24. 4-Methylcyclohexene Experiment 25. Phase-Transfer Catalysis: Addition of Dichlorocarbene to Cyclohexene Essay: Fats and Oils. Experiment 26. Methyl Stearate from Methyl Oleate. Essay: Soaps and Detergents. Experiment 27. Preparation of Soap. Experiment 28. Preparation of a Detergent. Essay: Petroleum and Fossil Fuels. Experiment 29. Gas Chromatographic Analysis of Gasolines. Essay: Detection of Alcohol: The Breathalyzer. Experiment 30. Chromic Acid Oxidation of Alcohols Experiment 30A. Chromic Acid Oxidation of Alcohols -- Visible Spectrophotometer Method. Experiment 30B. Chromic Acid Oxidation of Alcohols -- UV-VIS Spectrophotometer Method. Essay: Green Chemistry. Experiment 31. Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination. Experiment 31A. Chiral Reduction of Ethyl Acetoacetate. Experiment 31B. NMR Determination of the Optical Purity of (S)-Ethyl 3-Hydroxybutanoate. Experiment 32. Nitration of Aromatic Compounds Using a Recyclable Catalyst. Experiment 33. An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol. Experiment 34. Multi-Step Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid. Experiment 34A. Preparation of Benzoin by Thiamine Catalysis Experiment 34B. Preparation of Benzil. Experiment 34C. Preparation of Benzilic Acid. Experiment 35. Tetraphenylcyclopentadienone. Experiment 36. Triphenylmethanol and Benzoic Acid. Experiment 36A. Triphenylmethanol. Experiment 36B. Benzoic Acid. Experiment 37. Resolution of (+/-)-alpha-Phenylethylamine and Determination of Optical Purity. Experiment 37A. Resolution of (+/-)-alpha-Phenylethylamine. Experiment 37B. Determination of Optical Purity Using NMR and a Chiral Resolving Agent. Experiment 38. The Aldol Condensation Reaction: Preparation of Benzalacetophenones Chalcones). Experiment 39. Preparation of an alpha,beta-Unsaturated Ketone via Michael and Aldol Condensation Reactions. Experiment 40. Enamine Reactions: 2-Acetylcyclohexanone. Experiment 41. 1,4-Diphenyl-1,3-Butadiene. Experiment 42. Relative Reactivities of Several Aromatic Compounds. Experiment 43. Nitration of Methyl Benzoate. Essay: Local Anesthetics. Experiment 44. Benzocaine. Essay: Pheromones: Insect Attractants and Repellents. Experiment 45. N,N-Diethyl-m-Toluamide: The Insect Repellent "OFF". Essay: Sulfa Drugs. Experiment 46. Sulfa Drugs: Preparation of Sulfanilamide. Essay: Food Colors. Experiment 47. Chromatography of Some Dye Mixtures. Essay: Polymers and Plastics. Experiment 48. Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene. Experiment 48A. Polyesters. Experiment 48B. Polyamide (Nylon). Experiment 48C. Polystyrene. Experiment 48D. Infrared Spectra of Polymer Samples. Essay: Diels-Alder Reactions and Insecticides. Experiment 49. The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride. Experiment 50. Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone. Experiment 50A. Photoreduction of Benzophenone. Experiment 50B. Synthesis of beta-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol. Essay: Fireflies and Photochemistry. Experiment 51. Luminol. Essay: The Chemistry of Sweeteners. Experiment 52. Carbohydrates. Experiment 53. Analysis of a Diet Soft Drink by HPLC. Essay: Chemistry of Milk. Experiment 54. Isolation of Casein and Lactose from Milk. Experiment 54A. Isolation of Casein from Milk. Experiment 54B. Isolation of Lactose from Milk. Part IV: IDENTIFICATION OF ORGANIC SUBSTANCES. Experiment 55. Identification of Unknowns. Experiment 55A. Solubility Tests. Experiment 55B. Tests for the Elements (N, S, X). Experiment 55C. Tests for Unsaturation. Experiment 55D. Aldehydes and Ketones. Experiment 55E. Carboxylic Acids. Experiment 55F. Phenols. Experiment 55G. Amines. Experiment 55H. Alcohols. Experiment 55I. Esters. Part V: PROJECT-BASED EXPERIMENTS. Experiment 56. Preparation of a C-4 or C-5 Acetate Ester. Experiment 57. A Separation and Purification Scheme. Experiment 57A. Extractions with a separatory funnel. Experiment 57B. Extractions with a Screw-Cap centrifuge tube. Experiment 58. Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, or Fennel. Experiment 58A. Isolation of Essential Oils by Steam Distillation. Experiment 58B. Identification of the Constituents of Essential Oils by Gas Chromatography-Mass Spectrometry. Experiment 58C. Investigation of the Essential Oils of Herbs and Spices-Mini-Research Project. Experiment 59. Friedel-Crafts Acylation. Experiment 60. The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry. Experiment 61. Carbonation of an Unknown Aromatic Halide. Experiment 62. The Aldehyde Enigma. Experiment 63. Synthesis of Substituted Chalcones: A Guided-Inquiry Experience. Experiment 64. Michael and Aldol Condensation Reactions. Experiment 65. Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem. Experiment 66. An Oxidation Puzzle. Part VI: THE TECHNIQUES. Technique 1. Laboratory Safety. Technique 2. The Laboratory Notebook, Calculations, and Laboratory Records. Technique 3. Laboratory Glassware: Care and Cleaning. Technique 4. How to Find Data for Compounds: Handbooks and Catalogues. Technique 5. Measurement of Volume and Weight. Technique 6. Heating and Cooling Methods. Technique 7. Reaction Methods. Technique 8. Filtration. Technique 9. Physical Constants of Solids: The Melting Point. Technique 10. Solubility. Technique 11. Crystallization: Purification of Solids. Technique 12. Extractions, Separations, and Drying Agents. Technique 13. Physical Constants of Liquids: The Boiling Point and Density. Technique 14. Simple Distillation. Technique 15. Fractional Distillation, Azeotropes. Technique 16. Vacuum Distillation, Manometers. Technique 17. Sublimation. Technique 18. Steam Distillation. Technique 19. Column Chromatography. Technique 20. Thin-Layer Chromatography. Technique 21. High-Performance Liquid Chromatography (HPLC). Technique 22. Gas Chromatography. Technique 23. Polarimetry. Technique 24. Refractometry. Technique 25. Infrared Spectroscopy. Technique 26. Nuclear Magnetic Resonance Spectroscopy (Proton NMR). Technique 27. Carbon-13 Nuclear Magnetic Resonance Spectroscopy. Technique 28. Mass Spectrometry. Technique 29. Guide to the Chemical Literature. Appendix 1: Tables of Unknowns and Derivatives. Appendix 2: Procedure for Preparing Derivatives. Appendix 3: Index of Spectra.