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The Synthetic Organic Chemist's Companion

ISBN: 978-0-470-10707-2
208 pages
July 2007
The Synthetic Organic Chemist
The Organic Chemists' Companion provides a practical, hands-on resource for students and practitioners of organic synthesis. It presents the fundamentals and guides the reader through the entire process of organic synthesis. It includes basic instructions on everything from on handling reagents, gases, and solvents to conducting and working up/purifying reactions as well as applying analytical techniques to identify the reaction product.
  • Packed with data and practical tips and organized for quick reference
  • Includes guidelines for literature searches to help readers find additional information
  • Features colour photos, drawings, charts, graphs, and tables to complement the information
  • Includes real-life examples showing how to apply the information.
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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.

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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.
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  • Covers practical synthetic chemistry the way it is practiced in research labs today, and addresses topics such as SciFinder and related searching, microwave chemistry, ultrasonication, and solvent purification without distillation
  • Takes the experimenter from the initial commercial compound and literature search all the way through to the full characterization of the pure product
  • Follows the process that the chemist goes through, from initiating to completing a synthetic experiment
  • Includes guidelines for literature searches, handling and preparing reagents, gases, solvents, specific details for small scale reactions, conducting the reaction (including temperature control), following up (working up) the reaction ((including evaporation, vacuum, and purification), and identifying the product (including spectroscopy).
  • Packed with practical tips, data, and real-life examples
  • Includes numerous illustrations, lists, tables, and charts, including a solvent selection chart that makes information instantly accessible
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"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)

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