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Preface | |
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Introduction: Welcome to Organic Chemistry! | |
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Laboratory Safety | |
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Safety Guidelines | |
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Right-to-Know Laws | |
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Common Solvents | |
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Carcinogenic Substances | |
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References | |
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Advance Preparation and Laboratory Records | |
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The Notebook | |
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Notebook Format | |
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Laboratory Reports | |
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Submission of Samples | |
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Laboratory Glassware | |
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Cleaning Glassware | |
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Drying Glassware | |
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Ground-glass Joints | |
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Connecting Ground-glass Joints | |
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Capping Flasks, Conical Vials, and Openings | |
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Separating Ground-glass Joints | |
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Etching Glassware | |
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Attaching Rubber Tubing to Equipment | |
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Description of Equipment | |
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How to Find Data for Compounds: Handbooks and Catalogs | |
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CRC Handbook of Chemistry and Physics | |
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Lange's Handbook of Chemistry | |
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The Merck Index | |
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Aldrich Handbook of Fine Chemicals | |
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Strategy for Finding Information: Summary | |
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Problems | |
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Measurement of Volume and Weight | |
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Graduated Cylinders | |
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Dispensing Pumps | |
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Graduated Pipets | |
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Pasteur Pipets | |
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Syringes | |
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Automatic Pipets | |
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Measuring Volumes with Conical Vials, Beakers, and Erlenmeyer Flasks | |
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Balances | |
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Problems | |
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Heating and Cooling Methods | |
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Heating Mantles | |
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Hot plates | |
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Water Bath with Hot Plate/Stirrer | |
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Oil Bath with Hot Plate/Stirrer | |
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Aluminum Block with Hot Plate/Stirrer | |
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Sand Bath with Hot Plate/Stirrer | |
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Flames | |
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Steam Baths | |
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Cold Baths | |
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Problems | |
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Reaction Methods | |
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Assembling the Apparatus | |
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Heating under Reflux | |
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Stirring Methods | |
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Boiling Stones | |
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Addition of Liquid Reagents | |
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Drying Tubes | |
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Reactions Conducted under an Inert Atmosphere | |
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Capturing Noxious Gases | |
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Collecting Gaseous Products | |
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Evaporation of Solvents | |
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Rotary Evaporator | |
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Problems | |
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Filtration | |
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Gravity Filtration | |
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Filter Paper | |
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Vacuum Filtration | |
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Filtering Media | |
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The Aspirator | |
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Filter-Tip Pipet | |
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Craig Tubes | |
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Centrifugation | |
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Problems | |
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Physical Constants of Solids: The Melting Point | |
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Physical Properties | |
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The Melting Point | |
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Melting-Point Theory | |
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Mixture Melting Points | |
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Packing the Melting-Point Tube | |
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Determining the Melting Point--The Thiele Tube | |
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Determining the Melting Point--Electrical Instruments | |
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Decomposition, Discoloration, Softening, Shrinkage, and Sublimation | |
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Thermometer Calibration | |
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Problems | |
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Solubility | |
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Definition of Solubility | |
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Predicting Solubility Behavior | |
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Organic Solvents | |
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Problems | |
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Crystallization: Purification of Solids | |
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Theory | |
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Solubility | |
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Theory of Crystallization | |
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Macroscale Crystallization | |
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Macroscale Crystallization | |
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Microscale Crystallization | |
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Microscale Crystallization | |
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Additional Experimental Considerations: Macroscale and Microscale | |
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Selecting a Solvent | |
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Testing Solvents for Crystallization | |
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Decolorization | |
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Inducing Crystallization | |
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Drying Crystals | |
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Mixed Solvents | |
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Problems | |
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Extractions, Separations, and Drying Agents | |
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Theory | |
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Extraction | |
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Distribution Coefficient | |
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Choosing an Extraction Method and a Solvent | |
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Macroscale Extraction | |
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The Separatory Funnel | |
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Microscale Extraction | |
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The Conical Vial--Separating the Lower Layer | |
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The Conical Vial--Separating the Upper Layer | |
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The Screw-Cap Centrifuge Tube | |
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Additional Experimental Considerations: Macroscale and Microscale | |
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How Do You Determine Which One Is the Organic Layer? | |
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Drying Agents | |
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Emulsions | |
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Purification and Separation Methods | |
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Continuous Extraction Methods | |
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Continuous Solid-Liquid Extraction | |
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Continuous Liquid-Liquid Extraction | |
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Problems | |
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Physical Constants of Liquids: The Boiling Point and Density | |
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Boiling Points and Thermometer Corrections | |
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The Boiling Point | |
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Determining the Boiling Point--Microscale Methods | |
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Determining the Boiling Point--Other Methods | |
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Thermometer Stem Corrections | |
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Density | |
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Density | |
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Problems | |
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Simple Distillation | |
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The Evolution of Distillation Equipment | |
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Theory | |
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Distillation Theory | |
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Macroscale Distillation | |
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Simple Distillation--Macroscale Methods | |
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Microscale Distillation | |
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Simple Distillation--Microscale Methods | |
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Semimicroscale Distillation | |
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Simple Distillation--Semimicroscale Methods | |
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Problems | |
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Fractional Distillation; Azeotropes | |
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Theory | |
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Differences between Simple and Fractional Distillation | |
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Vapor-Liquid Composition Diagrams | |
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Raoult's Law | |
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Column Efficiency | |
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Types of Fractionating Columns and Packings | |
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Macroscale Distillation | |
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Fractional Distillation--Macroscale Methods | |
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Microscale Distillation | |
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Fractional Distillation--Microscale Methods | |
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Azeotropes | |
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Nonideal Solutions: Azeotropes | |
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Azeotropic Distillation: Applications | |
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Problems | |
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Vacuum Distillation; Manometers | |
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Theory | |
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The Effect of Pressure on Boiling Point | |
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Macroscale Distillation | |
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Vacuum Distillation--Macroscale Methods | |
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Vacuum Distillation: Stepwise Macroscale Directions | |
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Microscale Distillation | |
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Vacuum Distillation--Microscale Methods | |
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Simplified Microscale Apparatus | |
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Vacuum Distillation: Stepwise Microscale Directions | |
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Rotary Fraction Collectors | |
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Bulb-to-Bulb Distillation | |
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Semimicroscale Distillation | |
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Vacuum Distillation--Semimicroscale Methods | |
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Vacuum Pump Methods | |
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The Mechanical Vacuum Pump | |
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Manometers | |
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The Closed-End Manometer | |
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Connecting and Using a Manometer | |
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Problems | |
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Sublimation | |
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Theory | |
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Vapor Pressure Behavior of Solids and Liquids | |
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Sublimation Behavior of Solids | |
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Vacuum Sublimation | |
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Advantages of Sublimation | |
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Macroscale and Microscale Sublimation | |
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Sublimation--Methods | |
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Sublimation--Specific Directions | |
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Problems | |
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Steam Distillation | |
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Theory | |
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Differences between Distillation of Miscible and Immiscible Mixtures | |
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Immiscible Mixtures: Calculations | |
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Macroscale Distillation | |
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Steam Distillation--Macroscale Methods | |
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Microscale Distillation | |
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Steam Distillation--Microscale Methods | |
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Semimicroscale Distillation | |
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Steam Distillation--Semimicroscale Methods | |
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Problems | |
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Column Chromatography | |
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Adsorbents | |
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Interactions | |
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Principle of Column Chromatographic Separation | |
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Parameters Affecting Separation | |
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Packing the Column: Typical Problems | |
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Packing the Column: Preparing the Support Base | |
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Packing the Column: Depositing the Adsorbent--Dry Pack Methods | |
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Packing the Column: Depositing the Adsorbent--The Slurry Method | |
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Applying the Sample to the Column | |
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Elution Techniques | |
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Reservoirs | |
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Monitoring the Column | |
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Tailing | |
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Recovering the Separated Compounds | |
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Decolorization by Column Chromatography | |
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Gel Chromatography | |
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Flash Chromatography | |
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References | |
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Problems | |
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Thin-Layer Chromatography | |
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Principles of Thin-Layer Chromatography | |
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Commercially Prepared TLC Plates | |
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Preparation of Thin-Layer Slides and Plates | |
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Sample Application: Spotting the Plates | |
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Developing (Running) TLC Plates | |
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Choosing a Solvent for Development | |
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Visualization Methods | |
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Preparative Plates | |
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The R[subscript f] Value | |
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Thin-Layer Chromatography Applied in Organic Chemistry | |
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Paper Chromatography | |
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Problems | |
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High-Performance Liquid Chromatography (HPLC) | |
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Adsorbents and Columns | |
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Column Dimensions | |
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Solvents | |
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Detectors | |
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Presentation of Data | |
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Reference | |
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Problems | |
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Gas Chromatography | |
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The Gas Chromatograph | |
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The Column | |
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Principles of Separation | |
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Factors Affecting Separation | |
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Advantages of Gas Chromatography | |
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Monitoring the Column (The Detector) | |
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Retention Time | |
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Poor Resolution and Tailing | |
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Qualitative Analysis | |
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Collecting the Sample | |
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Quantitative Analysis | |
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Treatment of Data: Chromatograms Produced by Modern Data Stations | |
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Gas Chromatography-Mass Spectrometry (GC-MS) | |
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Problems | |
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Polarimetry | |
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Nature of Polarized Light | |
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The Polarimeter | |
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The Sample Cells | |
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Operation of the Polarimeter | |
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Optical Purity | |
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Problems | |
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Refractometry | |
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The Refractive Index | |
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The Abbe Refractometer | |
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Cleaning the Refractometer | |
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Temperature Corrections | |
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Problems | |
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Infrared Spectroscopy | |
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Sample Preparation and Recording the Spectrum | |
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Introduction | |
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Liquid Samples--NaCl Plates | |
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Liquid Samples--AgCl Plates | |
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Solid Samples--Dry Film | |
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Solid Samples--KBr Pellets and Nujol Mulls | |
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Solid Samples--Solution Spectra | |
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Recording the Spectrum | |
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Calibration | |
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Infrared Spectroscopy | |
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Uses of the Infrared Spectrum | |
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Modes of Vibration | |
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What to Look for in Examining Infrared Spectra | |
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Correlation Charts and Tables | |
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Analyzing a Spectrum (or What You Can Tell at a Glance) | |
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Survey of the Important Functional Groups | |
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References | |
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Problems | |
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Nuclear Magnetic Resonance Spectroscopy (Proton NMR) | |
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Preparing a Sample for NMR Spectroscopy | |
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Routine Sample Preparation Using Deuterated Chloroform | |
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Nonroutine Sample Preparation | |
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Reference Substances | |
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Nuclear Magnetic Resonance ([superscript 1] HNMR) | |
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The Chemical Shift | |
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Chemical Equivalence--Integrals | |
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Chemical Environment and Chemical Shift | |
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Local Diamagnetic Shielding | |
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Anisotropy | |
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Spin-Spin Splitting (n + 1 Rule) | |
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The Coupling Constant | |
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Magnetic Equivalence | |
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Spectra at Higher Field Strength | |
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Aromatic Compounds--Substituted Benzene Rings | |
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Protons Attached to Atoms Other Than Carbon | |
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Chemical Shift Reagents | |
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References | |
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Problems | |
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Carbon-13 Nuclear Magnetic Resonance Spectroscopy | |
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Preparing a Sample for Carbon-13 NMR | |
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Carbon-13 Chemical Shifts | |
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Proton-Coupled [superscript 13]C Spectra--Spin-Spin Splitting of Carbon-13 Signals | |
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Proton-Decoupled [superscript 13]C Spectra | |
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Some Sample Spectra--Equivalent Carbons | |
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Nuclear Overhauser Enhancement (NOE) | |
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Compounds with Aromatic Rings | |
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References | |
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Problems | |
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Mass Spectrometry | |
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The Mass Spectrum | |
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Molecular Formula Determination | |
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Detecting Halogens | |
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Fragmentation Patterns | |
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Interpreted Mass Spectra | |
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Rearrangement Reactions | |
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References | |
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Computational Chemistry | |
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Molecular Mechanics | |
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Molecular Mechanics | |
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Minimization and Conformation | |
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Limitations of Molecular Mechanics | |
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Current Implementations | |
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Ab initio and Semiempirical Methods | |
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Quantum Mechanical Calculations | |
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Ab Initio and Semiempirical Calculations | |
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Solving the Schrodinger Equation | |
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Basis Set Orbitals | |
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Semiempirical Methods | |
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Picking a Basis Set for Ab Initio Calculations | |
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Heats of Formation | |
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Graphical Models and Visualization | |
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Surfaces | |
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Mapping Properties onto a Density Surface | |
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References | |
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Guide to the Chemical Literature | |
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Locating Physical Constants: Handbooks | |
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General Synthetic Methods | |
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Searching the Chemical Literature | |
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Collections of Spectra | |
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Advanced Textbooks | |
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Specific Synthetic Methods | |
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Advanced Laboratory Methods | |
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Reaction Mechanisms | |
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Organic Qualitative Analysis | |
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Beilstein and Chemical Abstracts | |
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Computer Online Searching | |
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Scientific Journals | |
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Topics of Current Interest | |
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How to Conduct a Literature Search | |
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Problems | |
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Index | |