Handbook of Synthetic Organic Chemistry - 2nd Edition - ISBN: 9780128095812, 9780128095041

Handbook of Synthetic Organic Chemistry

2nd Edition

Authors: Michael Pirrung
eBook ISBN: 9780128095041
Paperback ISBN: 9780128095812
Imprint: Academic Press
Published Date: 30th August 2016
Page Count: 288
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Description

Handbook of Synthetic Organic Chemistry, Second Edition updates and expands the author’s popular 2007 work, Synthetic Organic Chemist’s Companion. This new handbook provides valuable, practical guidance; incorporates corrections, and includes coverage on important topics, such as lyophylization, crystallization, precipitation, HPLC detectors, gases, and microwave reactions.

The book maintains the useful organization of the author’s earlier work, beginning with a basic overview and walking through every practical step of the process of organic synthesis, from reagents, solvents, and temperature control, to documentation, implementation, purification, and analytical methods for the product.

From planning and setting up reactions, to recording them, the book provides insight and valuable guidance into every step of the process.

Key Features

  • Contains practical information for every part of the process that are coupled with engaging, real-world examples
  • Presents useful guidance for conducting literature searches, handling and preparing reagents, working up the reaction, and identifying the product
  • Presents valuable coverage of conventional and microwave temperature control, paper and electronic research notebooks, eluent selection, Schlenk lines, purification methods and determination, chiral chromatography, chemical safety, and more

Readership

Organic chemistry researchers and advanced students

Table of Contents

  • Foreword
  • Preface to the First Edition
  • Preface to the Second Edition
  • Acknowledgments
  • 1. Safety
    • 1.1. Training
    • 1.2. Safety Data Sheets
    • 1.3. Safety Pictograms
    • 1.4. Personal Protective Equipment
    • 1.5. General
  • 2. Searching the Literature
    • 2.1. Commercial Availability
    • 2.2. Literature Preparations
    • 2.3. Experimental Procedures
    • 2.4. Other Electronic Resources for Synthetic Chemistry
  • 3. Reagents
    • 3.1. Short-Path Distillation
    • 3.2. Ampules
    • 3.3. Reagent Solutions
    • 3.4. Titration
    • 3.5. Reagent Storage
    • 3.6. Subtle Reagent Variations
    • 3.7. Dangerous Reagents
    • 3.8. Reagent Properties
  • 4. Gases
    • 4.1. Lecture Bottles/Small Cylinders
    • 4.2. Tanks or Cylinders
    • 4.3. Gas Safety
  • 5. Reactions on a Small Scale—1–25mmol
    • 5.1. Reaction Flasks
    • 5.2. Stirring
    • 5.3. Glass Joints
    • 5.4. Inert Atmosphere
    • 5.5. Apparatus for Addition
    • 5.6. Condensers
    • 5.7. Other Equipment and Considerations
  • 6. Temperature Control
    • 6.1. Heating
    • 6.2. Cooling
  • 7. Solvents
    • 7.1. Selection
    • 7.2. Purity
    • 7.3. Degassing
    • 7.4. Ammonia
  • 8. The Research Notebook
    • 8.1. Paper Notebooks
    • 8.2. Electronic Notebooks
  • 9. Conducting the Reaction Itself
    • 9.1. Reagents Supplied as Dispersions
    • 9.2. Azeotropic Drying
    • 9.3. Stoichiometry
    • 9.4. Syringe and Inert Atmosphere Techniques
    • 9.5. General Procedure for Transfer of Materials by Syringe
    • 9.6. Addition
    • 9.7. Special Techniques
    • 9.8. Unattended Reactions
    • 9.9. Quenching
    • 9.10. Specialized Reagents
    • 9.11. Checklist
    • 9.12. Reaction Time Versus Purification Time
  • 10. Following the Reaction
    • 10.1. Thin Layer Chromatography
    • 10.2. Gas Chromatography
    • 10.3. High Performance Liquid Chromatography
    • 10.4. Nuclear Magnetic Resonance Spectroscopy
  • 11. Working Up Reactions
    • 11.1. Solvent Extraction
    • 11.2. Drying Organic Solutions
    • 11.3. Specialized Workups
    • 11.4. Destroying Reagents
  • 12. Evaporation
  • 13. Vacuum Systems
    • 13.1. Vacuum Sources
    • 13.2. Vacuum Manifolds
    • 13.3. Vacuum Gauges
  • 14. Purification of Products
    • 14.1. Distillation
    • 14.2. Silica Gel Chromatography
    • 14.3. Flash Column Chromatography
    • 14.4. Gradients
    • 14.5. Special Adsorbents
    • 14.6. Preparative Gas Chromatography
    • 14.7. Precipitation
    • 14.8. Trituration
    • 14.9. Crystallization
    • 14.10. Yields
  • 15. Methods for Structure Elucidation
    • 15.1. Nuclear Magnetic Resonance Spectroscopy
    • 15.2. Infrared Spectroscopy
    • 15.3. Ultraviolet Spectroscopy
    • 15.4. Combustion Analysis
    • 15.5. Mass Spectrometry
    • 15.6. Optical Rotation
    • 15.7. Chiral Chromatography
    • 15.8. Crystal Growth for X-Ray
    • 15.9. Novel Compound Characterization
  • 16. Cleaning Up After the Reaction
    • 16.1. Waste Disposal
    • 16.2. Cleaning Equipment
  • 17. Specific Example
    • 17.1. The Experimental
    • 17.2. The Org. Syn. Prep
    • 17.3. Comparison
  • 18. Strategies for Reaction Optimization
  • Appendix 1. Safety Protocols
  • Appendix 2. Synthetic Solvent Selection Chart
  • Appendix 3. Solvent Miscibility
  • Appendix 4. Freezing Points of Common Organic Solvents
  • Appendix 5. Toxicities of Common Organic Solvents
  • Appendix 6. Recipes for TLC Stains
  • Appendix 7. NMR Spectral Data of Common Contaminants of Organic and Organometallic Reaction Products
  • Appendix 8. Acidities of Organic Functional Groups
  • Appendix 9. Acidities of Organic Functional Groups in DMSO
  • Appendix 10. Stuck Joints
  • Index

Details

No. of pages:
288
Language:
English
Copyright:
© Academic Press 2017
Published:
Imprint:
Academic Press
eBook ISBN:
9780128095041
Paperback ISBN:
9780128095812

About the Author

Michael Pirrung

Michael Pirrung, Ph.D., was trained as a synthetic organic chemist at UT-Austin, UC-Berkeley, and Columbia University with eminent synthetic chemists Clayton Heathcock and Gilbert Stork. His independent career began in the 1980s at Stanford University and the biotech start-up company Affymax. In 1990, he joined Duke University where he founded and directed the Program in Biological Chemistry. In 2004, he joined the UC-Riverside Chemistry department as UC Presidential Chair, and in 2012 became Distinguished Professor. He has been a visiting professor at UC-Berkeley, Baylor College of Medicine, Oxford, UC-San Diego, UC-Irvine, and Caltech. He has trained over 100 graduate students and postdoctoral fellows. He has held Hertz, Sloan, and Guggenheim fellowships and a NSF Presidential Young Investigator Award. He has over 170 peer-reviewed publications, more than 40 US and international patents, and has authored six books. The scope of his research has been broad, including natural product total synthesis, photochemical methods development, mechanistic enzymology, rhodium carbenoid chemistry, microarrays, combinatorial chemistry, and medicinal chemistry. His current work emphasizes peptide chemistry. His microarray work has been particularly recognized, with the 1991 AAAS-Newcomb Cleveland Prize, the 1993 Intellectual Property Owners Distinguished Inventor Award, the 2004 Chemical Pioneer Award of the American Institute of Chemists, and the 2006 European Inventor of the Year (for small and medium-sized enterprises). His editorial board service includes Cell Chemical Biology and Journal of Combinatorial Chemistry. He has worked extensively with development-stage and Fortune 500 companies as a consultant or scientific advisory board member. He also has an active practice as an expert witness for litigation in nucleic acid diagnostics and generic drugs.

Affiliations and Expertise

University of California, Riverside, USA