Introduction Welcome to Organic Chemistry Laboratory Safety Organization of the Textbook Advance Preparation Budgeting Time Purpose The Techniques

Transcription

1 Introduction Welcome to Organic Chemistry Laboratory Safety Organization of the Textbook Advance Preparation Budgeting Time Purpose 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 Heating 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 Column Chromatography Thin-Layer Chromatography High-Performance Liquid Chromatography (HPLC) Gas Chromatography Polarimetry Refractometry Infrared Spectroscopy Nuclear Magnetic Resonance Spectroscopy (Proton NMR) Carbon-13 Nuclear Magnetic Resonance Spectroscopy 6 Mass Spectrometry Guide to the Chemical Literature Introduction to Basic Laboratory Techniques Solubility Crystallization Extraction

2 A Separation and Purification Scheme Extractions with a Separatory Funnel Chromatography Thin-Layer Chromatography Selecting the Correct Solvent for Thin-Layer Chromatography Monitoring a Reaction with Thin Layer Chromatography Column Chromatography Simple and Fractional Distillation Infrared Spectroscopy and Boiling-Point Determination Acetylsalicylic Acid Acetaminophen TLC Analysis of Analgesic Drugs Isolation of Caffeine Extraction of Caffeine from Tea Isolation of Caffeine from a Tea Bag Isopentyl Acetate (Banana Oil) Isolation of Eugenol from Cloves Spearmint and Caraway Oil (+)- and (-)-Carvones Isolation of Chlorophyll and Carotenoid Pigments from Spinach Ethanol from Sucrose Introduction to Molecular Modeling An Introduction to Molecular Modeling The Conformations of n-butane Local Minima Cyclohexane Chair and Boat Conformations Substituted Cyclohexane Rings (Critical Thinking Exercise) cis- and trans-2-butene Computational Chemistry Heats of Formation Isomerism, Tautomerism, and Regioselectivity Heats of Reaction SN1 Reaction Rates DensityûElectrostatic Potential Maps Acidities of Carboxylic Acids DensityûElectrostatic Potential Maps Carbocations DensityûLUMO Maps Reactivities of Carbonyl Groups Preparations and Reactions of Organic Compounds Reactivities of Some Alkyl Halides Nucleophilic Substitution Reactions Competing Nucleophiles Competitive Nucleophiles with 1-Butanol or 2-Butanol Competitive Nucleophiles with 2-Methyl-2-Propanol Analysis Synthesis of n-butyl Bromide and t-pentyl Chloride n-butyl Bromide t-pentyl Chloride

3 4-Methylcyclohexene Methyl Stearate from Methyl Oleate Gas-Chromatographic Analysis of Gasolines Biodiesel Biodiesel from Coconut Oil Biodiesel from Other Oils Analysis of Biodiesel Ethanol from Corn Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination Chiral Reduction of Ethyl Acetoacetate NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate Nitration of Aromatic Compounds Using a Recyclable Catalyst Reduction of Ketones Using Carrots as Biological Reducing Agents Resolution of (±)-a-phenylethylamine and Determination of Optical Purity Resolution of (±)-a-phenylethylamine Determination of Optical Purity Using NMR and a Chiral Resolving Agent An Oxidation-Reduction Scheme Borneol, Camphor, Isoborneol Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid Preparation of Benzoin by Thiamine Catalysis Preparation of Benzil Preparation of Benzilic Acid Triphenylmethanol and Benzoic Acid Triphenylmethanol Benzoic Acid Aqueous-Based Organozinc Reactions Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes using a Palladium Catalyst Grubbs Catalyzed Metathesis of Eugenol with 1,4-Butenediol to Prepare a Natural Product The Aldol Condensation Reaction Preparation of Benzalacetophenones (Chalcones) A Green Enantioselective Aldol Condensation Reaction Preparation of an a,b-unsaturated Ketone via Michael and Aldol Condensation Reactions Preparation of Triphenylpyridine 1,4-Diphenyl-1,3-Butadiene Relative Reactivities of Several Aromatic Compounds Nitration of Methyl Benzoate Benzocaine N,N-Diethyl-m-toluamide: The Insect Repellent "OFF" Sulfa Drugs: Preparation of Sulfanilamide Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene Polyesters

4 Polyamide (Nylon) Polystyrene Infrared Spectra of Polymer Samples Ring-Opening Metathesis Polymerization (ROMP) Using a Grubbs Catalyst: A Three-Step Synthesis of a Polymer Diels-Alder Reaction of Furan and Maleic Anhydride Ring Opening of Anhydride in Methanol Ring-Opening Metathesis Polymerization (ROMP) Diels-Adler Reaction Conversion of the Diels-Adler Adduct to the Diester Synthesizing the Polymer by Ring-Opening Metathesis Polymerization (ROMP) The DielsûAlder Reaction of Cyclopentadiene with Maleic Anhydride Diels-Alder Reaction with Anthracene-9-methanol Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone Photoreduction of Benzophenone Synthesis of b-benzpinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol Luminol Analysis of A Diet Soft Drink by HPLC Carbohydrates Identification of Organic Substances Identification of Unknowns Solubility Tests Tests of the Elements (N, S, X) Tests for Unsaturation Aldehydes and Ketones Carboxylic Acids Phenols Amines Alcohols Esters Project-Based Experiments Preparation of a C-4 or C-5 Acetate Ester Isolation of Essential Oils from Allspice, Caraway, Cinnamon, Cloves, Cumin, Fennel, or Star Anise Isolation of Essential Oils by Steam Distillation Identification of the Constituents of Essential Oils by Gas ChromatographyûMass Spectrometry Investigation of the Essential Oils of Herbs and SpicesùA Mini-Research Project Competing Nucleophiles in SN1 and SN2 Reactions Investigations Using 2-Pentanol and 3-Pentanol FriedelûCrafts Acylation The Analysis of Antihistamine Drugs by Gas ChromatographyûMass Spectrometry

5 Carbonation of an Unknown Aromatic Halide A Guided-Inquiry Experience Green Epoxidation of Chalcones Cyclopropanation Reactions on Chalcones Michael and Aldol Condensation Reactions Esterification Reactions of Vanillin The Use of NMR to Determine at Structure An Oxidation Puzzle Essays Aspirin Analgesics Identification of Drugs Caffeine EstersùFlavors and Fragrances Terpenes and Phenylpropanoids Stereochemical Theory of Odor The Chemistry of Vision Ethanol and Fermentation Chemistry Molecular Modeling and Molecular Mechanics Computational Chemistryùab Intio and Semiempirical Methods Fats and Oils Petroleum and Fossil Fuels Biofuels Green Chemistry Local Anesthetics Pheromones Sulfa Drugs Polymers and Plastics Diels-Alder Reaction and Insecticides Fireflies and Photochemistry The Chemistry of Sweeteners Appendices Tables of Unknowns and Derivatives Procedures for Preparing Derivatives Index of Spectra Table of Contents provided by Blackwell's Book Services and R.R. Bowker. Used with permission.