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Summary

Part I: TOOLS FOR THE ORGANIC LABORATORY. 1. Emergency Procedures and Safe Laboratory Practices. 2. General Laboratory Procedures. 3. Examination of Pure Compounds. 4. Chromatography. 5. Crystallization and Filtration. 6. Extraction and Drying. 7. Distillation and Related Techniques. 8. Introduction to Spectroscopy; Organic Structure Determination. 9. Nuclear Magnetic Resonance Spectroscopy. 10. Infrared Spectroscopy. 11. Mass Spectrometry. 12. Ultraviolet Visible Spectroscopy. 13. Special Laboratory Procedures. 14. The Organic Chemical Literature. Part II: EXPERIMENTS. 1. Introduction to Organic Microtechniques. 2. Determination of Melting Point. 3. Thin-Layer Chromatography of Analgesics. 4. Column Chromatography. 5. High Performance Liquid Chromatography; Natural Products from Spices. 6. Natural Products by Extraction; Trimyristin and Cholesterol. 7. Caffeine; Isolation of an Alkaloid. 8. Solubility Properties of Covalent Molecules and Their Ionic Salts. 9. Extraction and Crystallization; Acid-Base Properties. 10. Extraction and Crystallization; Acid-Base Properties. 11. Raoult's Law; Gas Chromatography. 12. Fractional Distillation; Gas Chromatography. 13. Free Radical Halogenation; Relative Reactivity by Product Analysis. 14. 2-Chloro-2-methylbutane (tert-Amyl Chloride). 15. Kinetic Investigation of Unimolecular Solvolysis. 16. Methylcyclohexenes; Alcohol Dehydration. 17. Resolution of a Racemic Modification. 18. Diphenylacetylene from Stilbene. 19. Introduction to Infrared Spectroscopy. 20. Divalent Carbon Intermediates; Phase Transfer Catalysis. 21. Homophthalic Acid; Oxidative Cleavage of a Double Bond. 22. Triphenylcarbinol; Addition of a Grignard Reagent to a Ketone. 23. Benzoic Acid; Carbonation of a Grignard Reagent. 24. Rates of Conversion of Alcohols to Alkyl Bromides. 25. The Diels-Alder Reaction of Maleic Anhydride and 1,3-Diphenylisobenzofuran. 26. Oxidation of (-)-Borneol to (-)-Camphor; Specific Rotation. 27. Oxidation of Alcohols to Aldehydes and Ketones. 28. Catalytic Hydrogenation. 29. Kinetic and Thermodynamic Reaction Conditions. 30. Heat of Reaction; Measurement of Resonance Energy. 31. Introduction to Nuclear Magnetic Resonance Spectroscopy. 32. Acetanilide to p Nitroaniline. 33. Aminoacetophenone; Selective Reduction of Nitro. 34. 4-Methylbenzophenone; Friedel-Crafts Acylation. 35. Photoreduction of Aromatic Ketones. 36. Carbocation Rearrangements; Benzopinacolone. 37. Aryl Migratory Aptitudes in Carbocation Rearrangements. 38. Borohydride Reduction of 9-fluorenone. 39. Hydroboration-Oxidation of 1-Hexene. 40. Synthetic Organic Polymers. 41. Electronic Effects of Substituents in Reactions; Acidity Constant Determination. 42. Acetylsalicylic Acid; Preparation of Aspirin. 43. Fischer Esterification. 44. Capryl Chloride and Capramide. 45. Chemiluminescence. 46. Synthesis of Sulfa Drugs; Using a Protected Amino Group. 47. Benzyl Alcohol; Complex Metal Hydride Reductions. 48. 9-Benzal- and 9-Benzylfluorene; Aldol and Cannizzaro Type Reactions. 49. Hexaphenylbenzene; Aldol and Diels-Alder Reactions. 50. Conjugate (Michael) Addition to á, '-Unsaturated Carbonyl. 51. Synthetic Dyes. 52. Forensic Chemistry; Detecting Traces of Blood. 53. Phenanthridone; Beckmann Rearrangement to a Heterocycle. 54. Qualitative Organic Analysis; Classification Tests. 55. Chemical and Spectral Analysis; Unknown Identification. 56. Spectroscopic Identification of an Unknown. Appendix. Answers to Selected Chapter Exercises. Index.

Tools For The Organic Laboratory
Emergency Procedures and Safe Laboratory Practices
General Laboratory Procedures
Examination of Pure Compounds
Chromatography
Crystallization and Filtration
Extraction and Drying
Distillation and Related Techniques
Introduction to Spectroscopy; Organic Structure Determination
Nuclear Magnetic Resonance Spectroscopy
Infrared Spectroscopy
Mass Spectrometry
Ultraviolet Visible Spectroscopy
Special Laboratory Procedures
The Organic Chemical Literature.
Experiments
Introduction to Organic Microtechniques
Determination of Melting Point
Thin-Layer Chromatography of Analgesics
Column Chromatography
High Performance Liquid Chromatography; Natural Products from Spices
Natural Products by Extraction; Trimyristin and Cholesterol
Caffeine; Isolation of an Alkaloid
Solubility Properties of Covalent Molecules and Their Ionic Salts
Extraction and Crystallization; Acid-Base Properties
Extraction and Crystallization; Acid-Base Properties
Raoult's Law; Gas Chromatography
Fractional Distillation; Gas Chromatography
Free Radical Halogenation; Relative Reactivity by Product Analysis
2-Chloro-2-methylbutane (tert-Amyl Chloride)
Kinetic Investigation of Unimolecular Solvolysis
Methylcyclohexenes; Alcohol Dehydration
Resolution of a Racemic Modification
Diphenylacetylene from Stilbene
Introduction to Infrared Spectroscopy
Divalent Carbon Intermediates; Phase Transfer Catalysis
Homophthalic Acid; Oxidative Cleavage of a Double Bond
Triphenylcarbinol; Addition of a Grignard Reagent to a Ketone
Benzoic Acid; Carbonation of a Grignard Reagent
Rates of Conversion of Alcohols to Alkyl Bromides
The Diels-Alder Reaction of Maleic Anhydride and 1,3-Diphenylisobenzofuran
Oxidation of (-)-Borneol to (-)-Camphor; Specific Rotation
Oxidation of Alcohols to Aldehydes and Ketones
Catalytic Hydrogenation
Kinetic and Thermodynamic Reaction Conditions
Heat of Reaction; Measurement of Resonance Energy
Introduction to Nuclear Magnetic Resonance Spectroscopy
Acetanilide to p Nitroaniline
Aminoacetophenone; Selective Reduction of Nitro
4-Methylbenzophenone; Friedel-Crafts Acylation
Photoreduction of Aromatic Ketones
Carbocation Rearrangements; Benzopinacolone
Aryl Migratory Aptitudes in Carbocation Rearrangements
Borohydride Reduction of 9-fluorenone
Hydroboration-Oxidation of 1-Hexene
Synthetic Organic Polymers
Electronic Effects of Substituents in Reactions; Acidity Constant Determination
Acetylsalicylic Acid; Preparation of Aspirin
Fischer Esterification
Capryl Chloride and Capramide
Chemiluminescence
Synthesis of Sulfa Drugs; Using a Protected Amino Group
Benzyl Alcohol; Complex Metal Hydride Reductions
9-Benzal- and 9-Benzylfluorene; Aldol and Cannizzaro Type Reactions
Hexaphenylbenzene; Aldol and Diels-Alder Reactions
Conjugate (Michael) Addition to ß, G-Unsaturated Carbonyl
Synthetic Dyes
Forensic Chemistry; Detecting Traces of Blood
Phenanthridone; Beckmann Rearrangement to a Heterocycle
Qualitative Organic Analysis; Classification Tests
Chemical and Spectral Analysis; Unknown Identification
Spectroscopic Identification of an Unknown
Appendix
Answers to Selected Chapter Exercises
Index
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