The Synthetic Organic Chemist's Companion

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.

Michael C. Pirrung, PhD, is a Professor of Chemistry and UC Presidential Chair at the University of California-Riverside. He received his PhD in organic chemistry at UC-Berkeley in 1980 under the direction of Clayton Heathcock and did postdoctoral work with Gilbert Stork at Columbia as an NSF postdoctoral fellow. He is a member and is on the Steering Committee for the Chemical Genomics IGERT Program and has served on the Editorial Boards of the Journal of Combinatorial Chemistry, QSAR and Combinatorial Science, and Chemistry and Biology.

"There is a wealth of practical advice on both everyday lab practices and also special problems ... the book is an excellent reminder of a number of key considerations and techniques for organic lab veterans. The book is written in a concise, easy-to-read style, and it includes numerous illustrations." (Journal of Natural Products, 2011) …this is an excellent book for an academic synthetic laboratory to have available as required reading for each new student (undergraduate or graduate) as they being their training in synthetic organic chemistry." (Journal of Medicinal Chemistry, February 2008) "Learning tricks from Pirrung will be useful for undergraduate students and lab technicians." (CHOICE, January 2008) "I am certain that he [the author] will find well-worn copies in many labs, read and reread by both experienced and inexperienced chemists…" (Journal of Chemical Education, November 2007)