Description
Like its previous five editions, this book is ideally suited for use in a sophomore-level laboratory course in organic chemistry.
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.
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
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