The synthetic organic chemist's companion

Abstract

Preface. Acknowledgments. 1. Searching the Literature. 1.1. Commercial availability. 1.2. Literature preparations. 2. Reagents. 2.1. Short path distillation. 2.2. Ampules. 2.3. Reagent solutions. 2.4. Titration. 2.5. Reagent storage. 2.6. Subtle reagent variations. 2.7. Dangerous reagents. 2.8. Reagent properties. 3. Gases. 3.1. Lecture bottles. 3.2. Tanks or cylinders. 3.3. Gas safety. 4. Reactions on a Small Scale - 1-25 mmol. 4.1. Reaction flasks. 4.2. Stirring. 4.3. Glass joints. 4.4. Inert atmosphere. 4.5. Apparatus for addition. 4.6. Condensers. 4.7. Other equipment and considerations. 5. Temperature Control. 5.1. Heating. 5.2. Cooling. 6. Solvents. 6.1. Selection. 6.2. Purity. 6.3. Degassing. 6.4. Ammonia. 7. The Research Notebook. 8. Conducting the Reaction Itself. 8.1. Reagents supplied as dispersions. 8.2. Azeotropic drying. 8.3. Stoichiometry. 8.4. Syringe and inert atmosphere techniques. 8.5. General procedure for transfer of materials by syringe. 8.6. Addition. 8.7. Special techniques. 8.7.1.Water removal. 8.7.2.Reactions above atmospheric pressure. 8.7.3.Reagent gases. 8.7.4.Ultrasonication. 8.8 Quenching . 8.9. Specialized reagents. 8.9.1. Diazomethane. 8.9.2. Lithium aluminum hydride. 8.9.3.Hydrogen peroxide. 8.10. Reaction time vs. purification time. 9. Following the Reaction. 9.1. Thin layer chromatography (TLC). 9.1.1. Cutting glass TLC plates. 9.1.2. Spotting TLC plates. 9.1.3. Eluting TLC plates. 9.1.4. Visualizing TLC plates. 9.2. Gas chromatography (GC). 9.3. High pressure liquid chromatography (HPLC). 9.4. NMR spectroscopy. 10. Working Up Reactions. 10.1. Solvent extracation. 10.2. Drying organic solutions. 10.3. Specialized work-ups. 10.3.1. Reactions producing triphenylphosphine oxide. 10.3.2. Reactions involving boron compounds. 10.3.3. Reactions involving copper salts. 10.3.4. Reactions involving aluminum reagents. 10.3.5. Reactions involving tin reagents. 11. Evaporation. 12. Vacuum Systems. 12.1. Vacuum sources. 12.2. Vacuum manifolds. 12.3. Vacuum gauges. 13. Purification of Products. 13.1. Distillation. 13.2. Silica gel chromatography. 13.3. Flash column chromatography. 13.4. Gradients. 13.5. Special absorbents. 13.5.1. Triethylamine-treated silica gel. 13.5.2. Oxalic acid-coated silica gel. 13.5.3. Silver nitrate-impregnated silica gel. 13.5.4. Other sorbents. 13.6. Preparative gas chromatography. 14. Methods for Structure Elucidation. 14.1. Nuclear magnetic resonance spectroscopy. 14.2. Infrared spectroscopy (IR). 14.3. Ultravilolet spectroscopy (UV). 14.4. Combustion analysis. 14.5. Mass spectrometry. 14.6. Crystallography. 15. Cleaning Up After the Reaction. 16. Specific Examples. 16.1. The experimental. 16.2. The Org. Syn. Prep. 16.3. Comparison. 17. Strategies for Reaction Organization. Appendices. 1. NMR spectral data of common contaminants of organic reaction products. 2. Synthetic solvent selection chart. 3. Recipes for TLC stains. 4. Mixotropic series. 5. Stuck joints. 6. Acidities of organic functional groups. 7. Acidities of organic functional groups in DMSO. 8. Web resources for synthetic chemistry.