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Introduction | |
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Welcome to Organic Chemistry | |
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Laboratory Safety | |
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Organization of the Textbook | |
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Advance Preparation | |
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Budgeting Time | |
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Purpose | |
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Introduction to Basic Laboratory Techniques | |
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Solubility | |
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Crystallization | |
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Extraction | |
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A Separation and Purification Scheme | |
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Extractions with a Separatory Funnel | |
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Extractions with a Screw-Cap Centrifuge Tube | |
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Chromatography | |
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Thin-Layer Chromatography | |
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Selecting the Correct Solvent for Thin-Layer Chromatography | |
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Monitoring a Reaction with Thin Layer Chromatography | |
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Column Chromatography | |
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Simple and Fractional Distillation | |
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Infrared Spectroscopy and Boiling-Point Determination Essay | |
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Aspirin | |
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Acetylsalicylic Acid | |
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Essay | |
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Analgesics | |
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Acetaminophen | |
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Essay | |
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Identification of Drugs | |
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TLC Analysis of Analgesic Drugs | |
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Essay | |
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Caffeine | |
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Isolation of Caffeine | |
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Extraction of Caffeine from Tea | |
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Isolation of Caffeine from a Tea Bag | |
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Essay | |
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Esters--Flavors and Fragrances | |
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Isopentyl Acetate (Banana Oil) | |
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Essay, Terpenes and Phenylpropanoids | |
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Isolation of Eugenol from Cloves | |
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Essay | |
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Stereochemical Theory of Odor | |
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Spearmint and Caraway Oil: (+)- and (-)- Carvones | |
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Essay | |
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The Chemistry of Vision | |
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Isolation of Chlorophyll and Carotenoid Pigments from Spinach | |
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Essay: Ethanol and Fermentation Chemistry | |
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Ethanol from Sucrose | |
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Introduction to Molecular Modeling | |
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Essay: Molecular Modeling and Molecular Mechanics | |
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An Introduction to Molecular Modeling | |
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The Conformations of n-Butane: Local Minima | |
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Cyclohexane Chair and Boat Conformations | |
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Substituted Cyclohexane Rings (Critical Thinking Exercise) | |
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cis- and trans-2-Butene | |
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Essay: Computational Chemistry - Ab initio and Semiempirical Methods | |
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Computational Chemistry | |
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Heats of Formation: Isomerism, Tautomerism, and Regioselectivity | |
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Heats of Reactions: SN1 Reaction Rates | |
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Density-Electrostatic Potential | |
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Maps: Acidities of Carboxylic Acids | |
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Density -Electrostatic Potential Maps: Carbocations | |
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Density -LUMO Maps: Reactivities of Carbonyl Groups | |
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Preparations and Reactions of Organic Compounds | |
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Reactivities of Some Alkyl Halides | |
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Nucleophilic Substitution Reactions: Competing Nucleophiles | |
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Competing Nucleophiles with 1-Butanol or 2-Butanol | |
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Competing Nucleophiles with 2-Methyl-2-Propanol | |
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Analysis | |
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Synthesis of n-Butyl Bromide and t-Pentyl Chloride | |
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n-Butyl Bromide | |
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t-Pentyl Chloride | |
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4-Methylcyclohexene Essay | |
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Fats and Oils | |
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Methyl Stearate from Methyl Oleate | |
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Essay: Petroleum and Fossil Fuels | |
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Gas Chromatographic Analysis of Gasolines | |
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Essay: Biofuels | |
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Biodiesel | |
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Biodiesel from Coconut Oil | |
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Biodiesel from Other Oils | |
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Analysis of Biodiesel | |
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Ethanol from Corn | |
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Essay: Green Chemistry | |
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Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination | |
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Chiral Reduction of Ethyl Acetoacetate | |
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NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate | |
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Nitration of Aromatic Compounds Using a Recyclable Catalyst | |
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Reduction of Ketones Using Carrots as Biological Reducing Agents | |
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Resolution of (+/-)-alpha-Phenylethylamine and Determination of Optical Purity | |
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Resolution of (+/-)-alpha-Phenylethylamine | |
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Determination of Optical Purity Using NMR and a Chiral Resolving Agent | |
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An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol | |
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Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid | |
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Preparation of Benzoin by Thiamine Catalysis | |
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Preparation of Benzil | |
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Preparation of Benzilic Acid | |
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Triphenylmethanol and Benzoic Acid | |
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Triphenylmethanol | |
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Benzoic Acid | |
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Aqueous-Based Organozinc Reactions | |
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Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium Catalyst | |
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Grubbs Catalyzed Metathesis of Eugenol with 1,4-Butenediol to Prepare a Natural Product | |
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The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones) | |
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A Green Enantioselective Aldol Condensation Reaction | |
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Preparation of an ?,?-Unsaturated Ketone via Michael and Aldol Condensation Reactions | |
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Preparation of Triphenylpyridine | |
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1,4-Diphenyl-1,3-Butadiene | |
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Relative Reactivities of Several Aromatic Compounds | |
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Nitration of Methyl Benzoate | |
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Essay | |
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Local Anesthetics | |
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Benzocaine | |
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Essay | |
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Pheromones: Insect Attractants and Repellants | |
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N,N-Diethyl-m-toluamide: The Insect Repellent "OFF." | |
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Essay: Sulfa Drugs | |
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Sulfa Drugs: Preparation of Sulfanilamide | |
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Essay: Polymers and Plastics | |
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Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene | |
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Polyesters | |
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Polyamide (Nylon) | |
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Polystyrene | |
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Infrared Spectra of Polymer Samples | |
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Ring-Opening Metathesis Polymerization (ROMP) | |
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Using a Grubbs Catalyst: A Three Step Synthesis of a Polymer | |
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Diels-Alder Reaction of Furan and Maleic Anhydride | |
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Ring Opening of Anhydride in Methanol | |
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Ring-Opening Metathesis Polymerization (ROMP) | |
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Diels-Adler Reaction | |
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Conversion of the Diels-Adler Adduct to the Diester | |
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Synthesizing the Polymer by Ring-Opening Metathesis Polymerization (ROMP) Essay | |
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Diels-Alder Reaction and Insecticides | |
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The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride | |
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Diels-Adler Reaction with Anthracine-9-Methanol | |
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Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone | |
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Photoreduction of Benzophenone | |
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Synthesis of ?-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol | |
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Essay | |
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Fireflies and Photochemistry | |
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Luminol | |
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Essay | |
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The Chemistry of Sweeteners | |
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Carbohydrates | |
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Analysis of a Diet Soft Drink by HPLC | |
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Identification of Organic Substances | |
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Identification of Unknowns | |
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Solubility Tests | |
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Tests for the Elements (N, S, X) | |
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Tests for Unsaturation | |
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Aldehydes and Ketones | |
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Carboxylic Acids | |
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Phenols | |
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Amines | |
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Alcohols | |
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Esters | |
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Project-Based Experiments | |
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Preparation of a C-4 or C-5 Acetate Ester | |
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Isolation of Essential Oils from Allspice, Caraway, Cinnamon, Cloves, Cumin, Fennel, or Star Anise | |
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Isolation of Essential Oils by Steam Distillation | |
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Identification of the Constituents of Essential Oils by Gas Chromatography-Mass Spectrometry | |
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Investigation of the Essential Oils of Herbs and Spices-Mini-Research Project | |
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Competing Nucleophiles in SN1 and SN2 | |
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Reactions: Investigations Using 2-Pentanol and 3-Pentanol | |
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Friedel-Crafts Acylation | |
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The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry | |
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Carbonation of an Unknown Aromatic Halide | |
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The Aldehyde Enigma | |
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Synthesis of Substituted Chalcones: A Guided-Inquiry Experience | |
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Green Epoxidation of Chalcones | |
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Cyclopropanation Reactions of Chalcones | |
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Michael and Aldol Condensation Reactions | |
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Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem | |
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An Oxidation Puzzle | |
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The Techniques | |
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Laboratory Safety | |
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The Laboratory Notebook, Calculations, and Laboratory Records | |
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Laboratory Glassware: Care and Cleaning | |
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How to Find Data for Compounds: Handbooks and Catalogues | |
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Measurement of Volume and Weight | |
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Heating and Cooling Methods | |
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Reaction Methods | |
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Filtration | |
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Physical Constants of Solids: The Melting Point | |
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Solubility | |
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Crystallization: Purification of Solids | |
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Extractions, Separations, and Drying Agents | |
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Physical Constants of Liquids: The Boiling Point and Density | |
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Simple Distillation | |
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Fractional Distillation, Azeotropes | |
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Vacuum Distillation, Manometers | |
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Sublimation | |
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Steam Distillation | |
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Column Chromatography | |
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Thin-Layer Chromatography | |
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High-Performance Liquid Chromatography (HPLC) | |
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Gas Chromatography | |
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Polarimetry | |
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Refractometry | |
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Infrared Spectroscopy | |
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Nuclear Magnetic Resonance Spectroscopy (Proton NMR) | |
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Carbon-13 Nuclear Magnetic Resonance Spectroscopy | |
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6 Mass Spectrometry | |
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Guide to the Chemical Literature | |
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Tables of Unknowns and Derivatives | |
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Procedure for Preparing Derivatives | |
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Index of Spectra | |