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1 Contents Preface vii PART 1 Introduction to Basic Laboratory Techniques 1 1 Introduction to Microscale Laboratory 2 2 Solubility 12 3 Crystallization 22 3A Semimicroscale and Hirsch 23 3B Microscale 26 3C Selecting a Solvent to Crystallize a 28 3D Mixture Melting Points 29 3E Critical Thinking Application 30 4 Extraction 34 4A Extraction of Caffeine 35 4B Distribution of a Solute Two Immiscible Solvents 37 4C How Do You One Is the Organic Layer? 38 4D Use of Extraction to Isolate a Neutral Compound from a Mixture an Acid or Base Impurity 39 4E Critical Thinking Application 41 5 A Separation and Purification 44 6 Chromatography 47 6A Thin-Layer Chromatography 48 6B Selecting the Correct Solvent for Thin-Layer Chromatography 50 6C Monitoring a Reaction with Thin-Layer Chromatography 51 6D Chromatography 52 7 Simple and Fractional Distillation 56 7A Simple and Fractional Distillation (Semimicroscale Procedure) 58 7B Simple and Fractional Distillation (Microscale Procedure) 62 8 Infrared Spectroscopy and Determination 64 Essay Aspirin 68 9 Acetylsalicylic Acid 71 Essay Isolation of the Active Ingredient in an Drug Acetaminophen 83 Acetaminophen (Microscale Procedure) 84 Acetaminophen (Semimicroscale Procedure) 86 Essay Identification of Drugs TLC Analysis of Analgesie Drugs 91 ) 2013 Cengage Learning. All Rights May not be scanned, copied or or posted to a publicly accessible Website, in or in part. XV A microscale approach to organic laboratory techniques 2013 digitalisiert durch: IDS Basel Bern
2 xvi Contents Essay Caffeine Isolation of Caffeine from Tea or Coffee A Extraction of Caffeine from Tea with Methylene Chloride B Extraction of Caffeine from Tea or Coffee Using Solid Phase Extraction (SPE) 105 Essay and Fragrances Isopentyl Acetate (Banana A Isopentyl Acetate (Microscale Procedure) B Isopentyl Acetate (Semimicroscale Procedure) 115 Essay and Phenylpropanoids Essential Extraction of Oil of Cloves by Distillation A Oil of Cloves (Microscale Procedure) B Oil of Cloves (Semimicroscale Procedure) 125 Essay Theory of Odor and Caraway Oil: (+)- and (-)-Carvones 131 Essay The of Vision Isolation of Chlorophyll and Carotenoid Pigments from Spinach 144 Essay Ethanol and Fermentation Chemistry Ethanol from Sucrose Introduction to Molecular Modeling 159 Essay Molecular Modeling and Molecular Mechanics An Introduction to Molecular Modeling A The Conformations of Minima B Cyclohexane Chair and Boat Conformations C Cyclohexane Rings (Critical Thinking Exercises) D and 168 Essay Methods 170 Initio and 20 Computational Chemistry A Heats of Formation: Isomerism, and Regioselectivity B Heats of Reaction: Reaction Rates C Density-Electrostatic Potential Acidities of Carboxylic Acids D Density-Electrostatic Potential Maps: Carbocations E Maps: Reactivities of Carbonyl Groups 182 PART 3 Properties and Reactions of Organic Compounds Reactivities Nucleophilic Substitution Reactions: Nucleophiles A Nucleophiles with or B Competitive Nucleophiles with 2-Methyl-2-Propanol C Analysis Synthesis of Bromide and Chloride A Bromide B n-butyl Bromide (Semimicroscale Procedure) C Chloride (Microscale Procedure) D Chloride (Semimicroscale Procedure) E Chloride (Macroseale Procedure) Cengage Learning. All Rights Reserved. May not be scanned, copied or or posted to a accessible Website, in or in
3 Contents xvii A 4-Methylcyclohexene (Microscale Procedure) B 4-Methylcyclohexene (Semimicroscale Procedure) 212 Essay Methyl Stearate from Methyl Oleate 220 Essay Petroleum and Fossil Analysis of 234 Essay Biofuels Biodiesel A Biodiesel from Coconut Oil B Biodiesel from Other Oils C Analysis of Biodiesel 246 Essay Green Chemistry Chiral Reduction of Acetoacetate; Optical Purity Determination A Chiral Reduction of Ethyl Acetoacetate B NMR Determination of the Optical Purity of Ethyl (S)-3- Hydroxybutanoate Nitration of Aromatic Compounds Using a Recyclable Catalyst Resolution of and Determination of Optical Purity A Resolution of B Determination of Optical Purity Using NMR and a Chiral Resolving Agent An Oxidation-Reduction Camphor, Isoborneol Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid A of Benzoin by Thiamine Catalysis B Preparation of C Preparation of Benzilic Acid Triphenylmethanol and Benzoic Acid A Triphenylmethanol B Benzoic Acid Sonogashira Coupling of Aromatic Compounds with Alkynes using a Palladium Catalyst Grubbs-Catalyzed Metathesis of Eugenol with to Prepare a Natural Product Aqueous-Based Organozinc Reactions The Condensation Reaction: Preparation of Benzalacetophenones Preparation of an Ketone via Michael and Aldol Condensation Reactions A Chloride (Wittig Salt) B Preparation of 1,4-Diphenyl-1,3-Butadiene Using Ethoxide to Generate the C Preparation of Using Potassium Phosphate to Generate the Ylide Relative Reactivities of Several Aromatic Compounds Nitration of Methyl Benzoate Cengage Learning. All Rights Reserved. May not be scanned, copied or duplicated, or posted to a accessible Website, in or in part.
4 iii Contents Essay Anesthetics Benzocaine Methyl Salicylate (Oil of Wintergreen) 372 Essay Insect Attractants and Repellents The Insect Repellent "OFF" 384 Essay Drugs Sulfa Drugs: Preparation of Sulfanilamide 392 Essay Polymers and Plastics Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene A Polyesters B Polyamide (Nylon) C Polystyrene D Infrared Spectra of Polymer Samples 412 Essay and Insecticides The Reaction of Cyclopentadiene with Maleic Anhydride The Diels-Alder Reaction with Anthracene-9-methanol Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone A Photoreduction of Benzophenone B Synthesis of The Rearrangement of Benzpinacol 435 Essay Fireflies and Photochemistry Essay The Chemistry of Sweeteners Analysis of a Diet Soft Drink by HPLC 450 PART 4 Identification of Organic Substances Identification of Unknowns A Solubility Tests B Tests for the Elements (N, S, X) C Tests for Unsaturation D Aldehydes and Ketones E Carboxylic Acids 483 Phenols G Amines H 491 Esters 496 PART 5 Project-Based Experiments Preparation of a C-4 or C-5 Acetate Ester Extraction of Essential Oils from Cinnamon, Cloves, Fennel, or Star Anise by Distillation A Isolation of Essential Oils by Steam Distillation B Identification of the Constituents of Essential Oils by Gas Spectrometry C Investigation of the Essential Oils of Herbs and Project Nucleophiles in and Reactions: Investigations Using and 514 ) 2013 Cengage Learning. All Rights Reserved. May not be scanned, copied or or posted to a accessible Website, in or in
5 Contents x: 56 Friedel-Crafts Acylation The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry The of Organozinc Reagents in Synthesis: An Exercise in Synthesis and Structure Proof by Spectroscopy Synthesis of Naproxen by Palladium Catalysis Aldehyde Disproportionation: A Structure Proof Problem Synthesis of Substituted Chalcones: A Experience Green Epoxidation of Chalcones Cyclopropanation of Chalcones Michael and Aldol Condensation Reactions Esterification Reactions of Vanillin: The Use of NMR to a Structure Proof Problem An Oxidation Puzzle 571 PART 6 The Techniques Laboratory Safety The Laboratory Notebook, Calculations, and Laboratory Records Laboratory Glassware: Care and Cleaning How to Find Data for Compounds: Handbooks and Catalogs Measurement of Volume and Weight and Cooling Methods Reaction Methods Filtration Physical Constants of Solids: The Melting Point Solubility Crystallization: Purification of Solids Extractions, Separations, and Drying Agents Physical Constants of Liquids: The Boiling Point and Density Simple Distillation Fractional Distillation, Azeotropes Vacuum Distillation, Manometers Sublimation Steam Distillation Chromatography Thin-Layer Chromatography High-Performance Liquid Chromatography (HPLC) Gas Chromatography Refractometry Spectroscopy Nuclear Magnetic Resonance Spectroscopy (Proton NMR) Nuclear Magnetic Resonance Spectroscopy Mass Spectrometry Guide to the Chemical Literature 969 Appendices Tables of Unknowns and Derivatives Procedures for Preparing Derivatives Index of Spectra ) 2013 Cengage Learning. All Rights Reserved. May not be scanned, copied or or posted to a accessible Website, in or in part.
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