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| Introduction | |
| Welcome to Organic Chemistry | |
| Laboratory Safety | |
| Organization of the Textbook | |
| Advance Preparation | |
| Budgeting Time | |
| Purpose | |
| Introduction to Basic Laboratory Techniques | |
| Solubility | |
| Crystallization | |
| Extraction | |
| A Separation and Purification Scheme | |
| Extractions with a Separatory Funnel | |
| Extractions with a Screw-Cap Centrifuge Tube | |
| 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 Essay | |
| Aspirin | |
| Acetylsalicylic Acid | |
| Essay | |
| Analgesics | |
| Acetaminophen | |
| Essay | |
| Identification of Drugs | |
| TLC Analysis of Analgesic Drugs | |
| Essay | |
| Caffeine | |
| Isolation of Caffeine | |
| Extraction of Caffeine from Tea | |
| Isolation of Caffeine from a Tea Bag | |
| Essay | |
| Esters--Flavors and Fragrances | |
| Isopentyl Acetate (Banana Oil) | |
| Essay, Terpenes and Phenylpropanoids | |
| Isolation of Eugenol from Cloves | |
| Essay | |
| Stereochemical Theory of Odor | |
| Spearmint and Caraway Oil: (+)- and (-)- Carvones | |
| Essay | |
| The Chemistry of Vision | |
| Isolation of Chlorophyll and Carotenoid Pigments from Spinach | |
| Essay: Ethanol and Fermentation Chemistry | |
| Ethanol from Sucrose | |
| Introduction to Molecular Modeling | |
| Essay: Molecular Modeling and Molecular Mechanics | |
| 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 | |
| Essay: Computational Chemistry - Ab initio and Semiempirical Methods | |
| Computational Chemistry | |
| Heats of Formation: Isomerism, Tautomerism, and Regioselectivity | |
| Heats of Reactions: SN1 Reaction Rates | |
| Density-Electrostatic Potential | |
| Maps: Acidities of Carboxylic Acids | |
| Density -Electrostatic Potential Maps: Carbocations | |
| Density -LUMO Maps: Reactivities of Carbonyl Groups | |
| Preparations and Reactions of Organic Compounds | |
| Reactivities of Some Alkyl Halides | |
| Nucleophilic Substitution Reactions: Competing Nucleophiles | |
| Competing Nucleophiles with 1-Butanol or 2-Butanol | |
| Competing Nucleophiles with 2-Methyl-2-Propanol | |
| Analysis | |
| Synthesis of n-Butyl Bromide and t-Pentyl Chloride | |
| n-Butyl Bromide | |
| t-Pentyl Chloride | |
| 4-Methylcyclohexene Essay | |
| Fats and Oils | |
| Methyl Stearate from Methyl Oleate | |
| Essay: Petroleum and Fossil Fuels | |
| Gas Chromatographic Analysis of Gasolines | |
| Essay: Biofuels | |
| Biodiesel | |
| Biodiesel from Coconut Oil | |
| Biodiesel from Other Oils | |
| Analysis of Biodiesel | |
| Ethanol from Corn | |
| Essay: Green Chemistry | |
| 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 (+/-)-alpha-Phenylethylamine and Determination of Optical Purity | |
| Resolution of (+/-)-alpha-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 ?,?-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 | |
| Essay | |
| Local Anesthetics | |
| Benzocaine | |
| Essay | |
| Pheromones: Insect Attractants and Repellants | |
| N,N-Diethyl-m-toluamide: The Insect Repellent "OFF." | |
| Essay: Sulfa Drugs | |
| Sulfa Drugs: Preparation of Sulfanilamide | |
| Essay: Polymers and Plastics | |
| Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene | |
| Polyesters | |
| 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) Essay | |
| Diels-Alder Reaction and Insecticides | |
| The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride | |
| Diels-Adler Reaction with Anthracine-9-Methanol | |
| Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone | |
| Photoreduction of Benzophenone | |
| Synthesis of ?-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol | |
| Essay | |
| Fireflies and Photochemistry | |
| Luminol | |
| Essay | |
| The Chemistry of Sweeteners | |
| Carbohydrates | |
| Analysis of a Diet Soft Drink by HPLC | |
| Identification of Organic Substances | |
| Identification of Unknowns | |
| Solubility Tests | |
| Tests for 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 Chromatography-Mass Spectrometry | |
| Investigation of the Essential Oils of Herbs and Spices-Mini-Research Project | |
| Competing Nucleophiles in SN1 and SN2 | |
| Reactions: Investigations Using 2-Pentanol and 3-Pentanol | |
| Friedel-Crafts Acylation | |
| The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry | |
| Carbonation of an Unknown Aromatic Halide | |
| The Aldehyde Enigma | |
| Synthesis of Substituted Chalcones: A Guided-Inquiry Experience | |
| Green Epoxidation of Chalcones | |
| Cyclopropanation Reactions of Chalcones | |
| Michael and Aldol Condensation Reactions | |
| Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem | |
| An Oxidation Puzzle | |
| The Techniques | |
| Laboratory Safety | |
| The Laboratory Notebook, Calculations, and Laboratory Records | |
| Laboratory Glassware: Care and Cleaning | |
| How to Find Data for Compounds: Handbooks and Catalogues | |
| 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 | |
| Tables of Unknowns and Derivatives | |
| Procedure for Preparing Derivatives | |
| Index of Spectra | |
| Table of Contents provided by Publisher. All Rights Reserved. |
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