Key Features of This Edition: Provides information on safety, glassware, lab cleanup, collection and disposal of waste, preparation of the laboratory notebook, and use of the chemical literature. Provides clear instructions on how to perform the procedures that are used. Appeals to the esthetic dimension by offering experiments in a variety of scales –from micro scale to semi-micro and to 5- and 10-gram scale. Includes descriptions of the interpretation of IR, UV/Vis, NMR and mass spectra. Gives procedures for the isolation of organic compounds from familiar materials such as nutmeg, cloves, citrus rind, tea, cola, NoDoz, aspirin, ibuprofen, milk and gallstones. Gives "recipes" for the preparation of organic compounds that illustrate many of the reactions that are discussed in the lecture part of the course. Gives procedures for the preparation of compounds with interesting properties: compounds that produce light, change color when heated, have different colors in different solvents, or turn blue in the sun. Includes the famous "bootstrap synthesis": the preparation of two molecules from one. Includes procedures for the preparation of 7 different compounds from vanillin.

CONTENTS PART 1. LABORATORY OPERATIONS Preface 1.Safety 2.Glassware Used in the Organic Chemistry Lab 3.Cleaning Up 4.Collection and Disposal of Waste 5.TheLaboratory Notebook 6.The Chemical Literature 7.Tables 8.Filtration 9.Recrystallization 10. Distillation 11. Reduced-Pressure Distillation 12. Distillation of Mixtures of Two Immiscible Liquids; Steam Distillation 13. Sublimation 14. Extraction by Solvents 15. Chromatography 16. Removal of Water 17. Boiling Point 18. Melting Point 19. Density 20. Index of Refraction 21. Optical Activity 22. Molecular Weight 23. Solubility 24. Infrared Absorption Spectrometry 25. Ultraviolet-Visible Absorption Spectrometry 26. Nuclear Magnetic Resonance Spectrometry 27. Mass Spectrometry 28. Qualitative Tests for the Elements 29. Qualitative Characterization Tests: Tests for Functional Groups 30. Characterization Through Formation of Derivatives 31. Assembling the Apparatus 32. Temperature Control 33. Methods of Heating and Cooling 34. Stirring 35. Addition of Reagents 36. Control of Evolved Gases 37. Concentration 38. Use of an Inert Atmosphere 39. Working Up the Reaction PART 2. EXPERIMENTS Isolations and Purifications E1. Isolation of Cholesterol from Gallstones E2. Isolation of Lactose from Powdered Milk E3. Isolation of Acetylsalicylic Acid from Aspirin Tablets E4. Isolation of Ibuprofen from Ibuprofen Tablets E5. Isolation of Caffeine from Tea and NoDoz E6. Isolation of Piperine from Back Pepper E7. Isolation of Trimyristin from Nutmeg E8. Isolation of Clove Oil from Cloves E9. Isolation of Eugenol from Clove Oil E10. Isolation of (R)-(+)-Limonene from Grapefruit or Orange Peel Ell. Isolation of (R)-(-)- or (S)-(+)-Carvone from Oil of Spearmint or Oil of Caraway E12. Resolution of alpha-Phenylethylamine by (R), (R)-(+)-Tartaric Acid Transformations E13. Adamantane from endo-Tetrahydrodicyclopentadiene via the Thiourea Clathrate E14. cis-Dibenzoylethyelene from trans-1,2-Dibenzoylethylene E15. Cyclohexanol from Cyclohexene E16. Cyclohexanol from Cyclohexanone E17. Cyclohexene from Cyclohexanol E18. Dehydration of 2-Methylcyclohexanol: A Variation E19. Cyclohexyl Bromide from Cyclohexanol E20. Cyclohexanone from Cyclohexanol E21. Addition of Dichlorocarbene to Cyclohexene E22. Addition of Dichlorocarbene to Styrene: A Variation E23. Addition of Dichlorocarbene to 1,5-Cyclooctadiene: Another Variation E24. Isoamyl Bromide from Isoamyl Alcohol E25. n-Butyl Bromide from n-Butyl Alcohol: A Variation E26. tert-Butyl Chloride from tert-Butyl Alcohol E27. tert-Amyl Chloride from tert-Amyl Alcohol: A Variation E28. Competitive Nucleophilic Substition of Butyl Alcohols by Bromide and Chloride Ion E29. Kinetics of the Hydrolysis of tert-Butyl Chloride E30. Isoamyl Acetate from Isoamyl Bromide and Potassium Acetate E31. Isoamyl Acetate from Isoamyl Alcohol and Acetic Acid; The Fischer Esterification E32. Cholesteryl Benzoate from Cholesterol E33. alpha-D-Glucose Pentaacetate from Glucose E34.beta-D-Glucose Pentaacetate from Glucose E35. Acetylation of Glucose in N-Methylimidazole: A Variation E36. Preparation of Methyl Benzoate, Oil of Niobe E37. Aliphatic Alcohols: Preparation by Grignard Synthesis E38. Preparation of Triphenylmethanol from Benzophenone E39. Preparation of Triphenylmethanol from Methyl Benzoate E40. Preparation of Triphenylmethanol from Dimethyl Carbonate E41. Preparation of Aniline from Nitrobenzene E42. Acetanilide from Aniline E43. N,N-Diethyl-m-Toluamide from m-Toluic Acid; A Mosquito Repellent: "Off" E44. Methyl m-Nitrobenzoate from Methyl Benzoate E45. p-Bromoacetanilide from Acetanilide E46. 2,4-Dinitrobenzene from Nitrobenzene E47. 2,4-Dinitroaniline E48. 2,4-Dinitrophenylhydrazine E49. 2,4-Dinitrodiphenylamine E50. 2,4-Dinitrophenylpiperidine E51. 4-Substituted 2,4-Dinitrophenylanilines: A Variation E52. Benzenediazonium Cloride from Aniline E53. p-Nitrobenzenediazonium Sulfate from p-Nitroaniline E54.Chlorobenzene from Benzenediazonium Chloride E55. Acetylvanillin from Vanillin E56. 5-Bromovanillin from Vanillin E57. 5-Nitrovanillin from Vanillin E58. Vanillin Oxime from Vanillin E59. Vanillin Semicarbazone from Vanillin E60. Vanillyl Alcohol from Vanillin E61. Vanillideneacetone from Vanillin E62. Benzenediazonium Chloride and beta-Naphthol: 1-Phenylazo-2-Naphthol (Sudan I) E63. p-Nitrobenzenediazonium Sulfate and Phenol: p-(4-nitrobenzeneazo)-phenol E64. p-Nitrobenzenediazonium Sulfate and beta-Naphthol: 1-(p-nitrophenylazo-2-naphthol (Para Red; American Flag Red) E65. p-Nitrobenzenediazonium Sulfate and Dimethylaniline: p-(4-Nitrobenzeneazo)-N,N-Dimethylaniline E66. Butadiene (from 3-Sulfolene) and Maleic Anhydride E67. Cyclopentadiene and Maleic Anhydride E68. Furan and Maleic Anhydride E69. alpha-Phellandrene and Maleic Anhydride E70. The Preparation of trans-Stilbene E71. Preparation of trans,trans-1,4-Diphenylbutadiene: A Variation E72. Acetylsalicylic Acid from Salicylic Acid: Preparation of Aspirin E73. p-Acetamidophenol from p-Aminophenol: Preparation of Tylenol E74. p-Ethoxyacetanilide from p-Ethoxyaniline: Preparation of Phenacetin E75. p-Ethoxyacetanilide from p-Acetamidophenol: Another Preparation of Phenacetin E76. 2-Nitrophenacetin from Phenacetin E77. Preparation of Methyl Salicylate: Oil of Wintergreen E78. 3-Nonenoic Acid from Heptaldehyde and Malonic Acid E79. Coconut Aldehyde from 3-Nonenoic Acid E80. Thiamine-Catalyzed Formation of Benzoin from Benzaldehyde E81. 1-Benzylnicotinamide Chloride from Nicotinamide E82. 1-Benzyldihydronicotinamide f rom 1-Benzylnicotinamide Chloride E83. Reduction of Malachite Green by 1-Benzyldihydronicotinamide E84. Dixanthylene from Xanthone E85. Dianthraquinone from Anthrone via 9-Bromoanthrone E86. A Photochromic Compound: 2-(2,4-Dinitrobenzl)pyridine E87. A Chemiluminescent Compound: Luminol Synthetic Sequences E88. Cholesterol Dibromide from Cholesterol E89. 5alpha, 6beta-Dibromocholestane-3-one from Cholesterol Dibromide E90. delta5-Cholestene-3-one from 5alpha, 6beta-Dibromocholestane-3-one E91. delta4-Cholestene-3-one from delta5-Cholestene-3-one E92. Benzoin from Benzaldehyde E93. Benzil brom Benzoin E94. Dibenzylketone from Phenylacetic Acid E95. Tetraphenylcyclopentadienone from Benzil and Dibenzyl Ketone E96. p-Acetamidobenzenesulfonyl Chloride from Acetanilide E97. p-Acetamidobenzenesulfonamide from p-Acetamidobenzenesulfonyl Chloride E98. Sulfanilamide from p-Acetamidobenzenesulfonamide E99. Ethyldioxyazobenzene from p-Phenetidine E100. Diethyldioxyazobenzene from Ethyldioxyazobenzene E101. p-Phenetidine from Diethyldioxyazobenzene E102. 2-Chloro-4-Bromoacetanilide from 4-Bromoacetanilide E103. 2-Chloro-4-bromoaniline from 2-Chloro-4-bromoacetanilide E104. 2-Chloro-4-bromo-6-iodoaniline from 2-Chloro-4-bromoaniline E105. 1-Bromo-3-Chloro-5-Iodobenzene from 2-Chloro-4-Bromo-6-Iodoaniline E106. 1,4-Diemthylpyridinium Iodide from 4-Methylpyridine and Methyl Iodide E107. Preparation of 4-(p-Hydroxystyryl)-1-Methylpyridinium Iodide from 1,4-Dimethylpyridinium Iodide and p-Hydroxybenzaldehyde E108. 1-Methyl-4-{(Oxocyclohexadienylidene)-Ethylidene}-1,4-Dihydropyridine (MOED) from 4-(p-Hydroxystyryl)-1-Methylpyridinium Iodide Appendices General Subject Index Chemical Substances Index

Includes bibliographies and indexes.