Introduction to Organic Laboratory Techniques

Introduction. WELCOME TO ORGANIC CHEMISTRY. Laboratory Safety. Organization of the Textbook. Advance Preparation. Budgeting Time. Purpose. Part One: 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 Catalogs. 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: 6 Mass Spectrometry. Technique 29: Guide to the Chemical Literature. Part Two: Introduction to Basic Laboratory Techniques. Experiment 1: Solubility. Experiment 2: Crystallization. Experiment 3: Extraction. Experiment 4: A Separation and Purification Scheme. Experiment 4A: Extractions with a Separatory Funnel. Experiment 5: Chromatography. Experiment 5A: Thin-Layer Chromatography. Experiment 5B: Selecting the Correct Solvent for Thin-Layer Chromatography. Experiment 5C: Monitoring a Reaction with Thin Layer Chromatography. Experiment 5D: Column Chromatography. Experiment 6: Simple and Fractional Distillation. Experiment 7: Infrared Spectroscopy and Boiling-Point Determination. Experiment 8: Acetylsalicylic Acid. Experiment 9: Acetaminophen. Experiment 10: TLC Analysis of Analgesic Drugs. Experiment 11: Isolation of Caffeine. Experiment 11A: Extraction of Caffeine from Tea. Experiment 11B: Isolation of Caffeine from a Tea Bag. Experiment 12: Isopentyl Acetate (Banana Oil). Experiment 13: Isolation of Eugenol from Cloves. Experiment 14: Spearmint and Caraway Oil: (+)- and (-)-Carvones. Experiment 15: Isolation of Chlorophyll and Carotenoid Pigments from Spinach. Experiment 16: Ethanol from Sucrose. Part Three: Introduction to Molecular Modeling. Experiment 17: An Introduction to Molecular Modeling. Experiment 17A: The Conformations of n-Butane: Local Minima. Experiment 17B: Cyclohexane Chair and Boat Conformations. Experiment 17C: Substituted Cyclohexane Rings (Critical Thinking Exercise). Experiment 17D: cis- and trans-2-Butene. Experiment 18: Computational Chemistry. Experiment 18A: Heats of Formation: Isomerism, Tautomerism, and Regioselectivity. Experiment 18B: Heats of Reaction: SN1 Reaction Rates. Experiment 18C: Density-Electrostatic Potential Maps: Acidities of Carboxylic Acids. Experiment 18D: Density-Electrostatic Potential Maps: Carbocations. Experiment 18E: Density-LUMO Maps: Reactivities of Carbonyl Groups. Part Four: Preparations and Reactions of Organic Compounds. Experiment 19: Reactivities of Some Alkyl Halides. Experiment 20: Nucleophilic Substitution Reactions: Competing Nucleophiles. Experiment 20A: Competitive Nucleophiles with 1-Butanol or 2-Butanol. Experiment 20B: Competitive Nucleophiles with 2-Methyl-2-Propanol. Experiment 20C: Analysis. Experiment 21: Synthesis of n-Butyl Bromide and t-Pentyl Chloride. Experiment 21A: n-Butyl Bromide. Experiment 21B: t-Pentyl Chloride. Experiment 22: 4-Methylcyclohexene. Experiment 23: Methyl Stearate from Methyl Oleate. Experiment 24: Gas-Chromatographic Analysis of Gasolines. Experiment 25: Biodiesel. Experiment 25A: Biodiesel from Coconut Oil. Experiment 25B: Biodiesel from Other Oils. Experiment 25C: Analysis of Biodiesel. Experiment 26: Ethanol from Corn. Experiment 27: Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination. Experiment 27A: Chiral Reduction of Ethyl Acetoacetate. Experiment 27B: NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate. Experiment 28: Nitration of Aromatic Compounds Using a Recyclable Catalyst. Experiment 29: Reduction of Ketones Using Carrots as Biological Reducing Agents. Experiment 30: Resolution of (+)-a-Phenylethylamine and Determination of Optical Purity. Experiment 30A: Resolution of (+)-a-Phenylethylamine. Experiment 30B: Determination of Optical Purity Using NMR and a Chiral Resolving Agent. Experiment 31: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol. Experiment 32: Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid. Experiment 32A: Preparation of Benzoin by Thiamine Catalysis. Experiment 32B: Preparation of Benzil. Experiment 32C: Preparation of Benzilic Acid. Experiment 33: Triphenylmethanol and Benzoic Acid. Experiment 33A: Triphenylmethanol. Experiment 33B: Benzoic Acid. Experiment 34: Aqueous-Based Organozinc Reactions. Experiment 35: Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes using a Palladium Catalyst. Experiment 36: Grubbs Catalyzed Metathesis of Eugenol with 1,4-Butenediol to Prepare a Natural Product. Experiment 37: The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones). Experiment 38: A Green Enantioselective Aldol Condensation Reaction. Experiment 39: Preparation of an a,b-Unsaturated Ketone via Michael and Aldol Condensation Reactions. Experiment 40: Preparation of Triphenylpyridine. Experiment 41: 1,4-Diphenyl-1,3-Butadiene. Experiment 42: Relative Reactivities of Several Aromatic Compounds. Experiment 43: Nitration of Methyl Benzoate. Experiment 44: Benzocaine. Experiment 45: N,N-Diethyl-m-toluamide: The Insect Repellent "OFF". Experiment 46: Sulfa Drugs: Preparation of Sulfanilamide. Experiment 47: Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene. Experiment 49A: Polyesters. Experiment 49B: Polyamide (Nylon). Experiment 49C: Polystyrene. Experiment 49D: Infrared Spectra of Polymer Samples. Experiment 48: Ring-Opening Metathesis Polymerization (ROMP) Using a Grubbs Catalyst: A Three-Step Synthesis of a Polymer. Experiment 48A: Diels-Alder Reaction of Furan and Maleic Anhydride. Experiment 48B: Ring Opening of Anhydride in Methanol. Experiment 48C: Ring-Opening Metathesis Polymerization (ROMP). Experiment 48A: Diels-Adler Reaction. Experiment 48B: Conversion of the Diels-Adler Adduct to the Diester. Experiment 48C: Synthesizing the Polymer by Ring-Opening Metathesis Polymerization (ROMP). Experiment 49: The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride. Experiment 50: Diels-Alder Reaction with Anthracene-9-methanol. Experiment 51: Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone. Experiment 51A: Photoreduction of Benzophenone. Experiment 51B: Synthesis of b-Benzpinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol. Experiment 52: Luminol. Experiment 53: Analysis of A Diet Soft Drink by HPLC. Experiment 54: Carbohydrates. Part Four: Identification of Organic Substances. Experiment 55: Identification of Unknowns. Experiment 55A: Solubility Tests. Experiment 55B: Tests of 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 Six: Project-Based Experiments. Experiment 56: Preparation of a C-4 or C-5 Acetate Ester. Experiment 57: Isolation of Essential Oils from Allspice, Caraway, Cinnamon, Cloves, Cumin, Fennel, or Star Anise. Experiment 57A: Isolation of Essential Oils by Steam Distillation. Experiment 57B: Identification of the Constituents of Essential Oils by Gas Chromatography-Mass Spectrometry. Experiment 57C: Investigation of the Essential Oils of Herbs and Spices-A Mini-Research Project. Experiment 58: Competing Nucleophiles in SN1 and SN2 Reactions: Investigations Using 2-Pentanol and 3-Pentanol. 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: Green Epoxidation of Chalcones. Experiment 65: Cyclopropanation Reactions on Chalcones. Experiment 66: Michael and Aldol Condensation Reactions. Experiment 67: Esterification Reactions of Vanillin: The Use of NMR to Determine at Structure. Experiment 68: An Oxidation Puzzle. Part Seven: Essays. Essay 1: Aspirin. Essay 2: Analgesics. Essay 3: Identification of Drugs. Essay 4: Caffeine. Essay 5: Esters-Flavors and Fragrances. Essay 6: Terpenes and Phenylpropanoids. Essay 7: Stereochemical Theory of Odor. Essay 8: The Chemistry of Vision. Essay 9: Ethanol and Fermentation Chemistry. Essay 10: Molecular Modeling and Molecular Mechanics. Essay 11: Computational Chemistry-ab Intio and Semiempirical Methods. Essay 12: Fats and Oils. Essay 13: Petroleum and Fossil Fuels. Essay 14: Biofuels. Essay 15: Green Chemistry. Essay 16: Local Anesthetics. Essay 17: Pheromones: Insect Attractants. Essay 18: Sulfa Drugs. Essay 19: Polymers and Plastics. Essay 20: Diels-Alder Reaction and Insecticides. Essay 21: Fireflies and Photochemistry. Essay 22: The Chemistry of Sweeteners. Appendices. Appendix 1: Tables of Unknowns and Derivatives. Appendix 2: Procedures for Preparing Derivatives. Appendix 3 Index of Spectra.