Introduction to Basic Laboratory Techniques Solubility Crystallization Extraction Chromatography Simple and Fractional Distillation Infrared

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1 Introduction to Basic Laboratory Techniques Solubility Crystallization Extraction Chromatography Simple and Fractional Distillation Infrared Spectroscopy and Boiling-Point Determination Essay: Aspirin Acetylsalicylic Acid Essay: Analgesics Acetanilide Acetaminophen Essay: Identification of Drugs TLC Analysis of Analgesic Drugs Essay: Caffeine Isolation of Caffeine Experiment Isolation of Caffeine from Tea Leaves Experiment Isolation of Caffeine from a Tea Bag Essay: Esters -- Flavors and Fragrances Isopentyl Acetate (Banana Oil) Methyl Salicylate (Oil of Wintergreen) 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 cis- and trans-2-butene Essay: Computational Chemistry -- Ab initio and Semiempirical Methods Computational Chemistry Heats of Formation: Isomerism, Tautomerism, and Regioselectivity

2 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 Properties 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 Hydrolysis of Some Alkyl Chlorides Synthesis of n-butyl Bromide and t-pentyl Chloride n-butyl Bromide t-pentyl Chloride 4-Methylcyclohexene Phase-Transfer Catalysis: Addition of Dichlorocarbene to Cyclohexene Essay: Fats and Oils Methyl Stearate from Methyl Oleate Essay: Soaps and Detergents Preparation of Soap Preparation of a Detergent Essay: Petroleum and Fossil Fuels Gas Chromatographic Analysis of Gasolines Essay: Detection of Alcohol: The Breathalyzer Chromic Acid Oxidation of Alcohols Chromic Acid Oxidation of Alcohols -- Visible Spectrophotometer Method Chromic Acid Oxidation of Alcohols -- UV-VIS Spectrophotometer Method Essay: Green Chemistry Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination Chiral Reduction of Ethyl Acetoacetate NMR Determination of the Optical Purity of (S)-Ethyl 3-Hydroxybutanoate Nitration of Aromatic Compounds Using a Recyclable Catalyst An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol Multi-Step Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid Preparation of Benzoin by Thiamine Catalysis Preparation of Benzil Preparation of Benzilic Acid Tetraphenylcyclopentadienone Triphenylmethanol and Benzoic Acid Triphenylmethanol Benzoic Acid

3 Resolution of (+/-)-alpha-phenylethylamine and Determination of Optical Purity Resolution of (+/-)-alpha-phenylethylamine Determination of Optical Purity Using NMR and a Chiral Resolving Agent The Aldol Condensation Reaction: Preparation of Benzalacetophenones Chalcones) Preparation of an alpha,beta-unsaturated Ketone via Michael and Aldol Condensation Reactions Enamine Reactions: 2-Acetylcyclohexanone 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 Repellents N,N-Diethyl-m-Toluamide: The Insect Repellent "OFF" Essay: Sulfa Drugs Sulfa Drugs: Preparation of Sulfanilamide Essay: Food Colors Chromatography of Some Dye Mixtures Essay: Polymers and Plastics Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene Polyesters Polyamide (Nylon) Polystyrene Infrared Spectra of Polymer Samples Essay: Diels-Alder Reactions and Insecticides The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone Photoreduction of Benzophenone Synthesis of beta-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 Essay: Chemistry of Milk Isolation of Casein and Lactose from Milk Isolation of Casein from Milk Isolation of Lactose from Milk Identification of Organic Substances Identification of Unknowns

4 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 A Separation and Purification Scheme Extractions with a separatory funnel Extractions with a Screw-Cap centrifuge tube Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, or Fennel 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 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 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

5 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 Mass Spectrometry Guide to the Chemical Literature Tables of Unknowns and Derivatives Procedure for Preparing Derivatives Index of Spectra. Table of Contents provided by Blackwell's Book Services and R.R. Bowker. Used with permission.

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