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Part One: INTRODUCTION TO BASIC LABORATORY TECHNIQUES. Experiment 1: Introduction to Microscale Laboratory. Experiment 2: Solubility. Experiment 3: Crystallization. Experiment 4: Extraction. Experiment 5: Chromatography. Experiment 6: Simple and Fractional Distillation. Experiment 6A: Simple and Fractional Distillation (Semi-Microscale Procedure). Experiment 6B: Simple and Fractional Distillation (Microscale Procedure). Experiment 7: Infrared Spectroscopy and Boiling-Point Elevation. Essay Aspirin. Experiment 8: Acetylsalicylic Acid. Essay Analgesics. Experiment 9: Isolation of the Active Ingredient in an Analgesic Drug. Experiment 10: Acetaminophen. Experiment 10A: Acetaminophen (Microscale Procedure). Experiment 10B: Acetaminophen (Semi-Microscale Procedure). Essay Identification of Drugs. Experiment 11: TLC Analysis of Analgesic Drugs. Essay Caffeine. Experiment 12: Isolation of Caffeine from Tea or Coffee. Experiment 12A: Extraction of Caffeine from Tea with Methylene Chloride. Experiment 12B: Extraction of Caffeine from Tea or Coffee Using Solid Phase Extraction (SPE). Essay Esters!XFlavors and Fragrances. Experiment 13: Isopentyl Acetate (Banana Oil). Experiment 13A: Isopentyl Acetate (Microscale Procedure). Experiment 12B: Isopentyl Acetate (Semi-Microscale Procedure). Essay Terpenes and Phenylpropanoids. Experiment 14: Essential Oils: Extractions of Oil from Cloves by Steam Distillation and Liquid Carbon Dioxide. Experiment 14A: Oil of Cloves (Microscale Procedure). Experiment 14B: Oil of Cloves (Semi-Microscale Procedure). Experiment 14C: Extraction of Oil of Cloves with Liquid Carbon Dioxide. 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 Two: 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!Vab Initio and Semiempirical Methods. Experiment 19: Computational Chemistry. Experiment 19A: Heats of Formation: Isomerism, Tautomerism, and Regioselectivity. Experiment 19B: Heats of Reaction: SN1 Reaction Rates. Experiment 19C: Density!VElectrostatic Potential Maps!XAcidities of Carboxylic Acids. Experiment 19D: Density!VElectrostatic Potential Maps: Carbocations. Experiment 19E: Density!VLUMO Maps: Reactivities of Carbonyl Groups. Part Three: PREPARATIONS AND REACTIONS OF ORGANIC COMPOUNDS. Experiment 20: Reactivities of Some Alkyl Halides. Experiment 21: Nucleophilic Substitution Reactions: Competing Nucleophiles. Experiment 21A: Competitive Nucleophiles with 1-Butanol or 2-Butanol. Experiment 21B: Competitive 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: n-Butyl Bromide (Semi-Microscale Procedure). Experiment 23C: t-Pentyl Chloride (Microscale Procedure). Experiment 23D: t-Pentyl Chloride (Semi-Microscale Procedure). Experiment 23E: t-Pentyl Chloride (Macroscale Procedure). Experiment 24: Elimination Reactions: Dehydration and Dehydrohalogenation. Experiment 24A: Dehydration of 1-Butanol and 2-Butanol. Experiment 24B: Dehydrobromination of 1-Bromobutane and 2-Bromobutane. Experiment 25: 4-Methylcyclohexene. Experiment 25A: 4-Methylcyclohexene (Microscale Procedure). Experiment 25B: 4-Methylcyclohexene (Semi-Microscale Procedure). Experiment 26: Phase-Transfer Catalysis: Addition of Dichlorocarbene to Cyclohexene. Experiment 27: Relative Reactivities of Several Aromatic Compounds. Experiment 28: Nitration of Methyl Benzoate. Essay Fats and Oils. Experiment 29: Methyl Stearate from Methyl Oleate. Essay Soaps and Detergents. Experiment 30: Preparation of a Soap. Experiment 31: Preparation of a Detergent. Essay Petroleum and Fossil Fuels. Experiment 32: Gas-Chromatographic Analysis of Gasolines. Essay Green Chemistry. Experiment 33: Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination. Experiment 33A: Chiral Reduction of Ethyl Acetoacetate. Experiment 33B: NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate. Experiment 34: Nitration of Aromatic Compounds Using a Recyclable Catalyst. Experiment 35: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol. Experiment 36: Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid. Experiment 36A: Preparation of Benzoin by Thiamine Catalysis. Experiment 36B: Preparation of Benzil. Experiment 36C: Preparation of Benzilic Acid. Experiment 37: Tetraphenylcyclopentadienone. Experiment 38: Triphenylmethanol and Benzoic Acid. Experiment 38A: Triphenylmethanol. Experiment 38B: Benzoic Acid. Experiment 39: Aqueous-Based Organozinc Reactions. Experiment 40: Resolution of (+)- a-Phenylethylamine and Determination of Optical Purity. Experiment 40A: Resolution of (+)-a-Phenylethylamine. Experiment 40B: Determination of Optical Purity Using NMR and a Chiral Resolving Agent. Experiment 41: The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones). Experiment 42: Preparation of an a,ss-Unsaturated Ketone via Michael and Aldol Condensation Reactions. Experiment 43: Enamine Reactions: 2-Acetylcyclohexanone. Experiment 44: 1,4-Diphenyl-1,3-butadiene. Experiment 44A: Benzyltriphenylphosphonium Chloride. Experiment 44B: Preparation of 1,4-diphenyl-1,3-butadiene Using Sodium Ethoxide To generate the Yilde. Experiment 44C: Preparation of 1,4-diphenyl-1,3-butadiene Using Potassium Phosphate To Generate the Yilde. Essay Local Anesthetics. Experiment 45: Benzocaine. Experiment 46: Methyl Salicylate (Oil of Wintergreen). Essay Pheromones: Insect Attractants and Repellants. Experiment 47: N,N-Diethyl-m-toluamide: The Insect Repellent "OFF." Essay Sulfa Drugs. Experiment 48: Sulfa Drugs: Preparation of Sulfanilamide. Essay Polymers and Plastics. Experiment 49: Preparation of Properties of Polymers: Polyester, Nylon, and Polystyrene. Experiment 49A: Polyesters. Experiment 49B: Polyamide (Nylon). Experiment 49C: Polystyrene. Experiment 49D: Infrared Spectra of Polymer Samples. Essay Diels!VAlder Reaction and Insecticides. Experiment 50: The Diels!VAlder Reaction of Cyclopentadiene with Maleic Anhydride. Experiment 51: Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone. Experiment 51A: Photoreduction of Benzophenone. Experiment 51B: Synthesis of ?O-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol. Essay Fireflies and Photochemistry. Experiment 52: Luminol. Essay The Chemistry of Sweeteners. Experiment 53: Analysis of A Diet Soft Drink by HPLC. Part Four: IDENTIFICATION OF ORGANIC SUBSTANCES. Experiment 54: Identification of Unknowns. Experiment 54A: Solubility Tests. Experiment 54B: Tests of the Elements (N, S, X). Experiment 54C: Tests for Unsaturation. Experiment 54D: Aldehydes and Ketones. Experiment 54E: Carboxylic Acids. Experiment 54F: Phenols. Experiment 54G: Amines. Experiment 54H: Alcohols. Experiment 54I: Esters. Part Five: PROJECT-BASED EXPERIMENTS. Experiment 55: A Separation and Purification Scheme. Experiment 56: Preparation of a C-4 or C-5 Acetate Ester. Experiment 57: Extraction of Essential Oils from Caraway, Cinnamon, Cloves, Cumin, or Fennel by Steam Distillation and Liquid Carbon Dioxide. Experiment 57A: Isolation of Essential Oils by Steam Distillation. Experiment 57B: Identification of the Constituents of Essential Oils by Gas Chromatography!VMass Spectrometry. Experiment 57C: Investigation of the Essential Oils of Herbs and Spices!XA Mini-Research Project. Experiment 57D: Extraction of an Essential Oil with Liquid Carbon Dioxide [New for 4e]. Experiment 58: Competing Nucleophiles in SN1 and SN2 Reactions: Investigations Using 2-Pentanol and 3-Pentanol. Experiment 59: Friedel!VCrafts Acylation. Experiment 60: The Analysis of Antihistamine Drugs by Gas Chromatography!VMass Spectrometry. Experiment 61: The Use of Organozinc Reagents in Synthesis: An Exercise in Synthesis and Structure Proof by Spectroscopy. 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 Six: 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. Appendices: Appendix 1. Tables of Unknowns and Derivatives. Appendix 2. Procedures for Preparing Derivatives. Appendix 3. Index of Spectra.Vom Verlag:
In this laboratory textbook for students of organic chemistry, experiments are designed to utilize microscale glassware and equipment. The textbook features a large number of traditional organic reactions and syntheses, as well as the isolation of natural products and experiments with a biological or health sciences focus. The organization of the text is based on essays and topics of current interest. The lab manual contains a comprehensive treatment of laboratory techniques.
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