A Microscale Approach to Organic Laboratory Techniques Book

PART I: INTRODUCTION TO BASIC LABORATORY TECHNIQUES. Experiment 1: Introduction to Microscale Laboratory. Experiment 2: Solubility. Experiment 3: Crystallization. Experiment 4: Extraction. Experiment 5: A Separation and Purification Scheme. Experiment 6: Chromatography. Experiment 7: Simple and Fractional Distillation. Experiment 8: Infrared Spectroscopy and Boiling Point Determination. ESSAY: Aspirin. Experiment 9: Acetylsalicylic Acid. ESSAY: Analgesics. Experiment 10: Isolation of the Active Ingredient in an Analgesic Drug. Experiment 11: Acetaminophen. ESSAY: Identification of Drugs. Experiment 12: TLC Analysis of Analgesic Drugs. ESSAY: Caffeine. Experiment 13: Isolation of Caffeine. ESSAY: Esters — Flavors and Fragrances. Experiment 14: Isopentyl Acetate (Banana Oil). ESSAY: Terpenes and Phenylpropanoids. Experiment 15: Essential Oils: Extraction of Oil of Cloves by Steam Distillation. Essay: Stereochemical Theory of Odor. Experiment 16: Spearmint and Caraway Oil: (+)- and (-)- Carvones. Essay: The Chemistry of Vision. Experiment 17: Isolation of Chlorophyll and Carotenoid Pigments from Spinach. Essay: Ethanol and Fermentation Chemistry. Experiment 18 Ethanol from Sucrose. PART II: INTRODUCTION TO MOLECULAR MODELING. ESSAY: Molecular Modeling and Molecular Mechanics. Experiment 19: An Introduction to Molecular Modeling. ESSAY: Computational Chemistry — Ab initio and Semiempirical Methods. Experiment 20: Computational Chemistry. PART III: PROPERTIES AND REACTIONS OF ORGANIC COMPOUNDS. Experiment 21: Reactivities of Some Alkyl Halides. Experiment 22: Nucleophilic Substitution Reactions: Competing Nucleophiles. Experiment 23: Synthesis of n-Butyl Bromide and t-Pentyl Chloride. Experiment 24: 4-Methylcyclohexene. ESSAY: Fats and Oils. Experiment 25: Methyl Stearate from Methyl Oleate. ESSAY: Petroleum and Fossil Fuels. Experiment 26: Gas Chromatographic Analysis of Gasolines. ESSAY: Biofuels. Experiment 27: Biodiesel. ESSAY: Green Chemistry. Experiment 28: Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination Using a Chiral Shift Reagent. Experiment 29: Nitration of Aromatic Compounds Using a Recyclable Catalyst. Experiment 30: Resolution of (?????Phenylethylamine and Determination of Optical Purity. Experiment 31: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol. Experiment 32: Multi-Step Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid. Experiment 33: Triphenylmethanol and Benzoic Acid. Experiment 34: Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium Catalyst. Experiment 35: Grubbs-Catalyzed Metathesis of Eugenol with 1,4-Butanediol to Prepare a Natural Product. Experiment 36: Aqueous-based Organozinc Reactions. Experiment 37: The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones). Experiment 38: Preparation of an ???-Unsaturated Ketone via Michael and Aldol Condensation Reactions. Experiment 39: The Wittig Reaction: Preparation of 1,4-Diphenyl-1,3-butadiene. Experiment 40: Relative Reactivities of Several Aromatic Compounds. Experiment 41: Nitration of Methyl Benzoate. ESSAY: Local Anesthetics. Experiment 42: Benzocaine. Experiment 43: Methyl Salicylate (Oil of Wintergreen). ESSAY: Pheromones: Insect Attractants and Repellents. Experiment 44: N,N-Diethyl-m-toluamide: The Insect Repellent "OFF." ESSAY: Sulfa Drugs. Experiment 45: Sulfa Drugs: Preparation of Sulfanilamide. Essay: Polymers and Plastics. Experiment 46: Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene. Essay: Diels-Alder Reactions and Insecticides. Experiment 47: The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride. Experiment 48: Diels-Alder Reaction with Anthracene-9-methanol. Experiment 49: Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone. ESSAY:Fireflies and Photochemistry. Experiment 50: Luminol. ESSAY: The Chemistry of Sweeteners. Experiment 51: Analysis of a Diet Soft Drink by HPLC. PART IV: IDENTIFICATION OF ORGANIC SUBSTANCES. Experiment 52: Identification of Unknowns. PART V: PROJECT-BASED EXPERIMENTS. Experiment 53: Preparation of a C-4 or C-5 Acetate Ester. Experiment 54: Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, Fennel, or Star Anise. Experiment 55: Competing Nucleophiles in SN1 and SN2 Reactions: Investigations using 2-Pentanol and 3-Pentanol. Experiment 56: Friedel-Crafts Acylation. Experiment 57: The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry. Experiment 58: The Use of Organozinc Reagents in Synthesis: An Exercise in Synthesis and Structure Proof by Spectroscopy. Experiment 59: Synthesis of Naproxen by Palladium Catalysis. Experiment 60: The Aldehyde Enigma. Experiment 61: Synthesis of Substituted Chalcones: A Guided-Inquiry Experience. Experiment 62: Green Epoxidation of Chalcones. Experiment 63: Cyclopropanation of Chalcones. 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. Technique 27: Carbon-13 Nuclear Magnetic Resonance Spectroscopy Technique 28: Mass Spectrometry. Technique 29: Guide to the Chemical Literature. APPENDICES: Appendix 1: Tables of Unknowns and Derivatives. Appendix 2: Procedures for Preparing Derivatives. Appendix 3: Index of Spectra.