This text for the two-semester introductory organic chemistry lab offers a series of clear and concise experiments that encourage accurate observation and deductive reasoning. A focus on biochemical and biomedical applications renders the narrative ideal for the mainstream organic chemistry laboratory. Emphasis is also placed on safety and the disposal of hazardous waste. Pre-lab exercises, marginal notes, clear line drawings, and questions help retain student interest and comprehension from lesson to lesson. The Ninth Edition includes "In This Experiment" objectives that clarify the goals of procedures. Optional, additional "For Further Investigation" features offer an in-depth exploration of the chemical principles presented.
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Ken Williamson is retired from Mt. Holyoke College where he taught the organic chemistry laboratory course. He is an established authority on microscale techniques and regularly holds workshops and travels to campuses in the U.S., Canada, and Europe to demonstrate the use of microscale.Review:
1. Introduction 2. Laboratory Safety and Waste Disposal Techniques 3. Crystallization 4. Melting Points, Boiling Points, and Refractive Indices 5. Distillation 6. Steam Distillation 7. Vacuum Distillation and Sublimation 8. Extraction of Acids and Bases and the Isolation of Caffeine from Coffee, Tea, and Cola Syrup 9. Thin-Layer Chromatography: Analysis of Analgesics and Isolation of Lycopene from Tomato Paste 10. Column Chromatography: Acetylferrocene, Cholesteryl Acetate, and Fluorenone 11. Alkenes from Alcohols: Analysis of a Mixture by Gas Chromatography 12. Infrared Spectroscopy 13. Nuclear Magnetic Resonance Spectroscopy 14. Ultraviolet Spectroscopy and Mass Spectrometry 15. Molecular Mechanics and Computational Chemistry Elimination, Substitution and Addition 16. The SN2 Reaction: 1-Bromobutane 17. Nucleophilic Substitution Reactions of Alkyl Halides 18. Alkanes and Alkenes: Radical Initiated Chlorination of 1-Chlorobutane; Reactions of Alkanes and Alkenes 19. Alkenes from Alcohols: Cyclohexene from Cyclohexanol 20. Bromination and Debromination: Purification of Cholesterol 21. Dichlorocarbene Oxidation and Reduction 22. Oxidation: Cyclohexanol to Cyclohexanone; Cyclohexanone to Adipic Acid 23. Pulegone from Citronellol: Oxidation with Pyridinium Chlorochromate 24. Oxidative Coupling of Alkynes: 2,7-Dimethyl-3,5-octadiyn-2,7-diol 25. Catalytic Hydrogenation 26. Sodium Borohydride Reduction of 2-Methylcyclohexanone: A Problem in Conformational Analysis 27. Epoxidation of Cholesterol Aromatic Substitution and Elimination 28. Nitration of Methyl Benzoate 29. Friedel-Crafts Alkylation of Benzene and Dimethoxybenzene; Host-Guest Chemistry 30. Alkylation of Mesitylene 31. Reactions of Triphenylmethyl Carbocation, Carbanion, and Radical 32. The Friedel-Crafts Reaction: Anthraquinone and Anthracene 33. Friedel-Crafts Acylation of Ferrocene: Acetylferrocene 34. 1,2,3,4-Tetraphenylnaphthalene via Benzyne 35. Triptycene via Benzyne Reactions of aldehydes and Ketones 36. Aldehydes and Ketones 37. Dibenzalacetone by the Aldol Condensation 38. Grignard Synthesis of Triphenylmethanol and Benzoic Acid 39. The Wittig and Wittig-Horner Reaction Reactions of Carboxylic Acids, Esters and Amines 40. Esterification and Hydrolysis 41. Acetylsalicylic Acid (Aspirin) 42. Malonic Ester Synthesis of a Barbiturate 43. Amines 44. Separation and Purification of the Components of an Analgesic Tablet: Aspirin, Caffeine, and Acetaminophen 45. The Sandmeyer Reaction: 1-Bromo-4-chlorobenzene, 2-Iodobenzoic Acid, and 4-Chlorotoluene 46. Sulfanilamide from Nitrobenzene 47. Dyes and Dyeing 48. Martius Yellow The Diels-Alder and Related Reactions 49. Diels-Alder Reaction 50. Ferrocene, [Bis(cyclopentadienyl)iron] 51. p-Terphenyl by the Diels-Alder Reaction 52. Tetraphenylcyclopentadienone 53. Hexaphenylbenzene and Dimethyl Tetraphenylphthalate Derivatives of 1,2-Diphenylethane: A Multistep Synthesis 54. The Benzoin Condensation: Cyanide Ion and Thiamine Catalyzed 55. Nitric Acid Oxidation. Preparation of Benzil from Benzoin. Synthesis of a Heterocycle: Diphenylquinoxaline 56. Borohydride Reduction of a Ketone: Hydrobenzoin from Benzil 57. Synthesis of 2,2-Dimethyl-1,5-dioxolane. The Acetonide Derivative of a Vicinal Diol 58. 1,4-Addition: Reductive Acetylation of Benzil 59. Synthesis of an Alkyne from an Alkene. Bromination and Dehydrobromination: Stilbene and Diphenylacetylene 60. The Perkin Reaction: Synthesis of alpha-Phenylcinnamic Acid Photochemistry 61. Decarboxylation: Synthesis of cis-Stilbene Photochemistry 62. Chemiluminescence: Syntheses of Cyalume and Luminol 63. Photochemistry: The Synthesis of Benzopinacol Natural Product Chemistry and Biochemistry 64. Carbohydrates and Sweeteners 65. Biosynthesis of Ethanol 66. Enzymatic Reactions: A Chiral Alcohol from a Ketone and Enzymatic Resolution of DL-Alanine 67. Isolation of Lycopene and beta-Carotene 68. The Synthesis of Natural Products: Pseudopellitierene and Camphor 69. Polymers: Synthesis and Recycling 70. Qualitative Organic Analysis 71. Searching the Chemical Literature
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