Organic Laboratory Techniques
INTRODUCTION TO THE ORGANIC LABORATORY Safety in the Laboratory / The Laboratory Notebook / Laboratory Equipment 1. CRYSTALLIZATION Solvents for Crystallization / Steps in Crystallization / Supplemental Procedures 2. MELTING POINTS Characteristics of Melting Points / Melting-Point Apparatus / Steps in Determining a Melting Point / Supplemental Procedures 3. EXTRACTION Immiscible Liquids / Distribution Coefficients / Extraction Solvents / Chemically Active Extraction / Steps in Extractions / Additional Techniques Used in Extractions / Other Extraction Techniques 4. DRYING ORGANIC SOLUTIONS Extraction with Aqueous Sodium Chloride / Solid Inorganic Drying Agents / Procedure for Using Solid Inorganic Drying Agents / Azeotropic Drying 5. SIMPLE DISTILLATION Characteristics of Distillation / Steps in a Simple Distillation / Microscale and Semi-Microscale Distillation 6. FRACTIONAL DISTILLATION Efficiency of the Fractionation Column / Steps in Fractional Distillation / Microscale Fractional Distillation 7. VACUUM DISTILLATION Boiling Point and Pressure / Apparatus for Simple Vacuum Distillation / Steps in Vacuum Distillation 8. STEAM DISTILLATION Characteristics of Steam Distillation / Calculation of the Amount of Water Needed in a Steam Distillation / Apparatus for Steam Distillation 9. SUBLIMATION Atmospheric Sublimation / Vacuum Sublimation 10. REFRACTIVE INDEX Correcting for Temperature Differences / Steps in Using a Refractometer 11. COLUMN CHROMATOGRAPHY Gravity Column Chromatography. Flash Chromatography (Macroscale) / Flash Chromatography (Microscale) / High-Performance Liquid Chromatography (HPLC) 12. THIN LAYER CHROMATOGRAPHY The RF Value / Equipment for TLC / Steps in a TLC Analysis / A Related Technique: Paper Chromatography 13. GAS CHROMATOGRAPHY Gas Chromatography / The Gas Chromatograph / Steps in a GC Analysis / Problems Encountered in GC / Uses of Gas Chromatograms 14. CARRYING OUT TYPICAL REACTIONS Stirring / Heating Reaction Mixtures / Controlling Exothermic Reactions / Adding Reagents to a Reaction Mixture. Excluding Moisture from a Reaction Mixture / Setting Up a Three-Neck Reaction Flask / Hydrogen Halide Gas Traps 15. INFRARED SPECTROSCOPY The Infrared Spectrum / Absorption of Infrared Radiation / Interpreting Infrared Spectra / Identifying Types of Compounds / Preparing a Sample for an Infrared Spectrum / Instrumentation 16. PROTON NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY The NMR Spectrum / Interpreting NMR Spectra / Use of Deuterium in Proton NMR Spectroscopy / NMR Spectra of Unknowns / The NMR Spectrometer / Preparing Samples for NMR Spectra 17. THE CHEMICAL LITERATURE Introduction to the Chemical Literature / Secondary Literature / Primary Literature / APPENDIX I. COMMONLY USED CALCULATIONS / Molarity / Normality / Dilutions / Percent Concentrations / Percent Yields and Theoretical Yields / APPENDIX II / ELEMENTAL ANALYSES / Determining the Empirical Formula / Determining the Molecular Formula / Interpreting the Results of Elemental Analysis / Degree of Unsaturation / APPENDIX III. HEALTH HAZARDS OF COMPOUNDS USED IN ORGANIC CHEMISTRY / Where to Find Chemical Hazard Information / Understanding Health Hazard Warnings