Lehman, John W. 　著

内容

目次

Preface. Introduction. I. MASTERING THE OPERATIONS. 1. Learning BasicOperations. The Effect of pH on a Food Preservative. 2. Extraction andEvaporation. Separating the Components of "Panacetin." 3. Recrystallizationand Melting-Point Measurement. Identifying a Constituent of "Panacetin." 4.Heating under Reflux. Synthesis of Salicylic Acid from Wintergreen Oil. 5.Simple Distillation, Gas Chromatography. Preparation of Synthetic Banana Oil.6. Fractional Distillation. Separation of Petroleum Hydrocarbons. 7.Addition, Mixing, Sublimation. Preparation of Camphor. 8. Boiling Point,Refractive Index. Identification of a Petroleum Hydrocarbon. 9. ColumnChromatography, UV-VIS Spectrometry. Isolation and Isomerization of Lycopenefrom Tomato Paste. 10. Steam Distillation, Infrared Spectrometry. Isolationand Identification of the Major Constituent of Clove Oil. 11. Thin-LayerChromatography, NMR Spectrometry. Identification of Unknown Ketones. 12.Vacuum Distillation, Optical Rotation. Optical Activity of a-Pinene. II.CORRELATED LABORATORY EXPERIMENTS. 13. Investigation of a Chemical Bond byInfrared Spectrometry. 14. Properties of Common Functional Groups. 15.Thin-Layer Chromatographic Analysis of Drug Components. 16. Separation of anAlkane Clathrate. 17. Isomers and Isomerization Reactions. 18. Structuresand Properties of Stereoisomers. 19. Bridgehead Reactivity in an SN1Solvolysis Reaction. 20. Reaction of Iodoethane with Saccharin, an AmbidentNucleophile. 21. Dehydration of Methylcyclohexanols. 22. Synthesis of7,7-Dichloronorcarane Using a Phase-Transfer Catalyst. 23. Stereochemistryof the Addition of Bromine to trans-Cinnamic Acid. 24. Hydration of aDifunctional Alkyne. 25. Preparation of Bromotriphenylmethane and the TritylFree Radical. 26. Chain-Growth Polymerization of Styrene and MethylMethacrylate. 27. Synthesis of Ethanol by Fermentation. 28. Reaction ofButanols with Hydrobromic Acid. 29. Borohydride Reduction of Vanillin toVanillyl Alcohol. 30. Synthesis of Triphenylmethanol and the TritylCarbocation. 31. Identification of a Conjugated Diene from Eucalyptus Oil.32. Spectral Identification of Monoterpenoids. 33. Synthesis and SpectralAnalysis of Aspirin. 34. Preparation of Nonbenzenoid Aromatic Compounds.35. Mechanism of the Nitration of Arenes by Nitronium Fluoborate. 36.Friedel-Crafts Acylation of Anisole. 37. Structure of a Natural Product inAnise Oil. 38. Identification of an Oxygen-Containing Organic Compound. 39.Wittig Synthesis of 1,4-Diphenyl-1,3-Butadiene. 40. Effect of ReactionConditions on the Condensation of Furfural with Cyclopentanone. 41. HaloformOxidation of 4'-Methoxyacetophenone. 42. Electronic Effect of a para-IodoSubstituent. 43. Synthesis and Identification of an Unknown Carboxylic Acid.44. Preparation of the Insect Repellent N,N-Diethyl-meta-toluamide. 45.Synthesis of 2-Acetylcyclohexanone by the Stork Reaction. 46. Synthesis ofDimedone and Measurement of its Tautomeric Equilibrium Constant. 47.Preparation of Para Red and Related Azo Dyes. 48. Reaction of Phthalimidewith Sodium Hypochlorite. 49. Identification of an Unknown Amine. 50.Preparation and Mass Spectrum of 2-Phenylindole. 51. Nucleophilic Strengthand Reactivity in SNAr Reactions. 52. Structure of an Unknown d-Hexose. 53.Fatty Acid Content of Commercial Cooking Oils. 54. Structure of an UnknownDipeptide. 55. Multistep Synthesis of Benzilic Acid from Benzaldehyde. 56.Using the Chemical Literature in an Organic Synthesis. 57. A ResearchProject in Organic Chemistry. III. MINILABS. 1. Making Useful LaboratoryItems. 2. Extraction of Iodine by Dichloromethane. 3. Purification of anUnknown Compound by Recrystallization. 4. Developing and Testing aHypothesis. 5. Preparation of Acetate Esters. 6. Gas ChromatographicAnalysis of Commercial Xylene. 7. Isolation of Caffeine from No-Doz Tablets.8. A Missing-Label Puzzle. 9. Paper Chromatography of Dyes in CommercialDrink Mixes. 10. Gas Chromatographic Analysis of an Essential Oil fromOrange Peel. 11. Identification of an Unknown Felt-Tip-Pen Ink by TLC. 12.Optical Rotation of Turpentine. 13. The Structures of Organic Molecules.14. Who Else Has My Compound? 15. Isomers and Molecular Structure. 16.Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions. 17. AnSN1 Reaction of Bromotriphenylmethane. 18. Preparation and Properties of aGaseous Alkene. 19. Addition of Iodine to a-Pinene. 20. Unsaturation inCommercial Products. 21. Free-Radical Stability. 22. The Nylon Rope Trick.23. Nucleophilic Substitution Rates of Alcohols. 24. Photoreduction ofBenzophenone. 25. Oxidation of Alcohols by Potassium Permanganate. 26.Preparation of a Fluorescent Dye. 27. Diels-Alder Reaction of MaleicAnhydride and Furan. 28. Identification of an Unknown Arene by NMRSpectrometry. 29. Interpretation of a Mass Spectrum. 30. Nitration ofNaphthalene. 31. Preparation of Carbocations by the Friedel-Crafts Reaction.32. Air Oxidation of Fluorene to 9-Fluorenone. 33. A NucleophilicAddition-Elimination Reaction of Benzil. 34. Preparation of AldolCondensation Products. 35. A Spontaneous Reaction of Benzaldehyde. 36.Acid-Base Strengths of Organic Compounds. 37. Hydrolysis Rates of Esters.38. Preparation of Benzamide. 39. Synthesis of Dimedone Derivatives ofBenzaldehyde. 40. A Diazonium Salt Reaction of 2-Aminobenzoic Acid. 41.Beckmann Rearrangement of Benzophenone Oxime. 42. Dyeing with Indigo. 43.Reaction of Monosaccharides with Phenols. 44. Extraction of Trimyristin fromNutmeg. 45. Preparation of a Soap Using a Phase-Transfer Catalyst. 46.Isolation of a Protein from Milk. IV. QUALITATIVE ORGANIC ANALYSIS. AnOverview of Qual Organic. Preliminary Work. Purification. Measurement ofPhysical Constants. Physical Examination. Ignition Test. Classification.Solubility Tests. Classification Tests. Spectral Analysis. InfraredSpectra. NMR Spectra. Identification. List of Possibilities. AdditionalTests and Data. Preparation of Derivatives. Exercises. V. THE OPERATIONS.A. Basic Operations. Cleaning and Drying Glassware. Using SpecializedGlassware. Using Glass Rod and Tubing. Weighing. Measuring Volume. MakingTransfers. B. Operations for Conducting Chemical Reactions. Heating.Cooling. Temperature Monitoring. Mixing. Addition of Reactants. C.Separation Operations. Gravity Filtration. Vacuum Filtration.Centrifugation. Extraction. Evaporation. Steam Distillation. ColumnChromatography. Thin-Layer Chromatography. Paper Chromatography. D. Washingand Drying Operations. Washing Liquids. Drying Liquids. Drying Solids.Drying and Trapping Gases. E. Purification Operations. Recrystallization.Sublimation. Simple Distillation. Vacuum Distillation. FractionalDistillation. F. Measuring Physical Constants. Melting Point. BoilingPoint. Refractive Index. Optical Rotation. G. Instrumental Analysis. GasChromatography. High-Performance Liquid Chromatography. InfraredSpectrometry. Nuclear Magnetic Resonance Spectrometry. Ultraviolet-VisibleSpectrometry. Mass Spectrometry. Appendixes and Bibliography. Index.