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Keep Smiling

The synthetic organic chemist's companion / Michael C. Pirrung.

By: Material type: TextTextPublication details: Hoboken, N.J. : Wiley-Interscience, 2007Description: xiii, 198 p. ill. (some col.) ; 23 cmISBN:
  • 9780470107072 (cloth)
Subject(s): DDC classification:
  • 547.2 22 P672
Contents:
Table of Contents Preface Acknowledgments Table of Contents 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
List(s) this item appears in: Chemistry
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Includes bibliographical references (p. 187-188) and index

Table of Contents
Preface
Acknowledgments
Table of Contents
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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