Techniques and Experiments For Organic Chemistry, 6e
by Ault
ISBN: | Copyright 1998
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This truly comprehensive yet compact lab manual offers a wide range of excellent experiments in a variety of scales _x0013_ from micro to semi micro. Clear instructions and safety information is also included, as well as recipes for the preparation of organic compounds and procedures for the preparation of compounds with interesting properties. Safety instructions are included throughout.
Published under the University Science Books imprint
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| Preface to the Sixth Edition (pg. xix) | |
| Preface to the Fifth Edition (pg. xxi) | |
| PART 1 Laboratory Operations (pg. 1) | |
| Preliminary Topics (pg. 3) | |
| 1. Safety (pg. 3) | |
| 2. Glassware Used in the Organic Chemistry Laboratory (pg. 16) | |
| 3. Cleaning Up (pg. 21) | |
| 4. Collection and Disposal of Waste (pg. 24) | |
| 5. The Laboratory Notebook (pg. 26) | |
| 6. The Chemical Literature (pg. 31) | |
| 7. Tables (pg. 38) | |
| Separation of Substances;Purification of Substances (pg. 43) | |
| 8. Filtration (pg. 44) | |
| 9. Recrystallization (pg. 48) | |
| 10. Distillation (pg. 62) | |
| 11. Reduced-Pressure Distillation (pg. 80) | |
| 12. Distillation of Mixtures of Two Immiscible Liquids; Steam Distillation (pg. 87) | |
| 13. Sublimation (pg. 90) | |
| 14. Extraction by Solvents (pg. 92) | |
| 15. Chromatography (pg. 109) | |
| 16. Removal of Water; Drying (pg. 129) | |
| Determinationof Physical Properties (pg. 137) | |
| 17. Boiling Point (pg. 138) | |
| 18. Melting Point (pg. 150) | |
| 19. Density; Specific Gravity (pg. 159) | |
| 20. Index of Refraction (pg. 161) | |
| 21. Optical Activity (pg. 163) | |
| 22. Molecular Weight (pg. 168) | |
| 23. Solubility (pg. 169) | |
| 24. Infrared Absorption Spectrometry (pg. 182) | |
| 25. Ultraviolet-Visible Absorption Spectrometry (pg. 201) | |
| 26. Nuclear Magnetic Resonance Spectrometry (pg. 207) | |
| 27. Mass Spectrometry (pg. 231) | |
| Determination of Chemical Properties: Qualitative Organic Analysis (pg. 239) | |
| 28. Qualitative Tests for the Elements (pg. 241) | |
| 29. Qualitative Characterization Tests: Tests for the Functional Groups (pg. 247) | |
| 30. Characterization Through Formation of Derivatives (pg. 266) | |
| Apparatus and Techniques For Chemical Reactions (pg. 299) | |
| 31. Assembling the Apparatus (pg. 299) | |
| 32. Temperature Control (pg. 302) | |
| 33. Methods of Heating and Cooling (pg. 305) | |
| 34. Stirring (pg. 310) | |
| 35. Addition of Reagents (pg. 313) | |
| 36. Control of Evolved Gases (pg. 315) | |
| 37. Concentration; Evaporation (pg. 317) | |
| 38. Use of an Inert Atmosphere (pg. 318) | |
| 39. Working Up the Reaction; Isolation of the Product (pg. 319) | |
| PART 2 Experiments (pg. 325) | |
| Isolations and Purifications (pg. 327) | |
| E1. Isolation of Cholesterol from Gallstones (pg. 327) | |
| E2. Isolation of Lactose from Powdered Milk (pg. 329) | |
| E3. Isolation of Acetylsalicylic Acid from Aspirin Tablets (pg. 332) | |
| E4. Isolation of Ibuprofen from Ibuprofen Tablets (pg. 335) | |
| E5. Isolation of Caffeine from Tea and NoDoz (pg. 337) | |
| E6. Isolation of Piperine from Black Pepper (pg. 340) | |
| E7. Isolation of Trimyristin from Nutmeg (pg. 342) | |
| ES. Isolation of Clove Oil from Cloves (pg. 344) | |
| E9. Isolation of Eugenol from Clove Oil (pg. 346) | |
| E10. Isolation of {R)-{+)-Limonene from Grapefruit or Orange Peel (pg. 347) | |
| E11. Isolation of (R)-(-)- or (S)-(+)Carvone from Oil of Spearmint or Oil of Caraway (pg. 350) | |
| E12. Resolution of a-Phenylethylamine by {R),{R)-{+)-Tartaric Acid (pg. 355) | |
| Transformations (pg. 363) | |
| E13. Adamantane from endo-Tetrahydrodicyclopentadienevia the Thiourea Clathrate (pg. 364) | |
| E14. cis-Dibenzoylethyelene from trans-1 ,2-Dibenzoylethylene (pg. 367) | |
| E15. Cyclohexanol from Cyclohexene (pg. 371) | |
| E16. Cyclohexanol from Cyclohexanone (pg. 373) | |
| E17. Cyclohexene from Cyclohexanol (pg. 376) | |
| E18. Dehydration of 2-Methylcyclohexanol: A Variation (pg. 381) | |
| E19. Cyclohexyl Bromide from Cyclohexanol (pg. 384) | |
| E20. Cyclohexanone from Cyclohexanol (pg. 387) | |
| E21. Addition of Dichlorocarbene to Cyclohexene (pg. 392) | |
| E22. Addition of Dichlorocarbene to Styrene: A Variation (pg. 394) | |
| E23. Addition of Dichlorocarbene to 1,5-Cyclooctadiene: Another Variation (pg. 395) | |
| E24. Isoamyl Bromide from Isoamyl Alcohol (pg. 398) | |
| E25. n-Butyl Bromide from n-Butyl Alcohol: A Variation (pg. 402) | |
| E26. tert-Butyl Chloride from tert-Butyl Alcohol (pg. 403) | |
| E27. tert-Amyl Chloride from tert-Amyl Alcohol: A Variation (pg. 406) | |
| E28. Competitive Nucleophilic Substitution of Butyl Alcohols by Bromide and Chloride lon (pg. 407) | |
| E29. Kinetics of the Hydrolysis of tert ButylChloride (pg. 410) | |
| E30. Isoamyl Acetate from Isoamyl Bromide and Potassium Acetate (pg. 421) | |
| E31. Isoamyl Acetate from Isoamyl Alcohol and Acetic Acid; The Fischer Esterification (pg. 424) | |
| E32. Cholesteryl Benzoate from Cholesterol (pg. 428) | |
| E33. a-o-Giucose Pentaacetate from Glucose (pg. 433) | |
| E34. ~-o-Giucose Pentaacetate from Glucose (pg. 433) | |
| E35. Acetylation of Glucose in N-Methylimidazole: A Variation (pg. 434) | |
| E36. Preparation of Methyl Benzoate, Oil of Niobe (pg. 436) | |
| E37. Aliphatic Alcohols: Preparation by Grignard Synthesis (pg. 440) | |
| E38. Preparation of Triphenylmethanol from Benzophenone (pg. 446) | |
| E39. Preparation of Triphenylmethanol from Methyl Benzoate (pg. 448) | |
| E40. Preparation of Triphenylmethanol from Dimethyl Carbonate (pg. 451) | |
| E41. Preparation of Aniline from Nitrobenzene (pg. 454) | |
| E42. Acetanilide from Aniline (pg. 457) | |
| E43. N,N-Diethyl-m-Toluamide from m-Toluic Acid; A Mosquito Repellent: "Off" (pg. 461) | |
| E44. Methyl m-Nitrobenzoate from Methyl Benzoate (pg. 464) | |
| E45. p-Bromoacetanilide from Acetanilide (pg. 466) | |
| E46. 2,4-Dinitrobromobenzene from Bromobenzene (pg. 469) | |
| E47. 2,4-Dinitroaniline (pg. 473) | |
| E48. 2,4-Dinitrophenylhydrazine (pg. 474) | |
| E49. 2,4-Dinitrodiphenylamine (pg. 475) | |
| ESO. 2,4-Dinitrophenylpiperidine (pg. 477) | |
| E51. 4-Substituted 2,4-Dinitrophenylanilines: A Variation (pg. 478) | |
| E52. Benzenediazonium Chloride from Aniline (pg. 481) | |
| E53. p-Nitrobenzenediazonium Sulfate from p-Nitroaniline (pg. 482) | |
| E54. Chlorobenzene from Benzenediazonium Chloride (pg. 483) | |
| E55. Acetylvanillin from Vanillin (pg. 486) | |
| E56. 5-Bromovanillin from Vanillin (pg. 487) | |
| E57. 5-Nitrovanillin from Vanillin (pg. 489) | |
| E58. Vanillin Oxime from Vanillin (pg. 490) | |
| E59. Vanillin Semicarbazone from Vanillin (pg. 491) | |
| E60. Vanillyl Alcohol from Vanillin (pg. 493) | |
| E61. Vanillideneacetone from Vanillin (pg. 494) | |
| E62. Benzenediazonium Chloride and f3-Naphthol: 1-Phenylazo-2-Naphthol {Sudan I) (pg. 499) | |
| E63. p-Nitrobenzenediazonium Sulfate and Phenol: p-(4-nitrobenzeneazo )ยท phenol (pg. 502) | |
| E64. p-Nitrobenzenediazonium Sulfate and p-Naphthol:1-(p-nitrophenylazo )-2-naphthol (Para Red; American Flag Red) (pg. 503) | |
| E65. p-Nitrobenzenediazonium Sulfate and Dimethylaniline: p-{ 4-n itrobenzeneazo )-N,N Dimethylaniline (pg. 505) | |
| E66. Butadiene (from 3-Sulfolene) and Maleic Anhydride (pg. 508) | |
| E67. Cyclopentadiene and Maleic Anhydride (pg. 510) | |
| E68. Furan and Maleic Anhydride (pg. 514) | |
| E69. a.-Phellandrene and Maleic Anhydride (pg. 515) | |
| E70. The Preparation of trans-Stilbene (pg. 519) | |
| E71. Preparation of trans,trans-1 ,4-Diphenylbutadiene: A Variation (pg. 524) | |
| E72. Acetylsalicylic Acid from Salicylic Acid: Preparation of Aspirin (pg. 527) | |
| E73. p-Acetamidophenol from p-Aminophenol:Preparation of Tylenol (pg. 529) | |
| E7 4. p-Ethoxyacetanilide from p-Ethoxyaniline:Preparation of Phenacetin (pg. 531) | |
| E75. p-Ethoxyacetanilide fromp-Acetamidophenol: Another Preparation of Phenacetin (pg. 535) | |
| E76. 2-Nitrophenacetin from Phenacetin (pg. 536) | |
| E77. Preparation of Methyl Salicylate: Oil of Wintergreen (pg. 538) | |
| E78. 3-Nonenoic Acid from Heptaldehyde and Malonic Acid (pg. 541) | |
| E79. Coconut Aldehyde from 3-Nonenoic Acid (pg. 543) | |
| E80. Thiamine-Catalyzed Formation of Benzoin from Benzaldehyde (pg. 546) | |
| E81. 1-Benzylnicotinamide Chloride from Nicotinamide (pg. 554) | |
| E82. 1-Benzyldihydronicotinamide from 1-Benzylnicotinamide Chloride (pg. 556) | |
| E83. Reduction of Malachite Green by 1-Benzyldihydronicotinamide (pg. 557) | |
| E84. Dixanthylene from Xanthone (pg. 560) | |
| E85. Dianthraquinone from Anthrone via 9-Bromoanthrone (pg. 561) | |
| E86. A Photochromic Compound:2-(2,4-Dinitrobenzyl)pyridine (pg. 564) | |
| E87. A Chemiluminescent Compound: Luminol (pg. 567) | |
| Synthetic Sequences:Experiments that Use a Sequence of Reactions (pg. 571) | |
| E88. Cholesterol Dibromide from Cholesterol (pg. 580) | |
| E89. 5a,6~-Dibromocholestane-3-one from Cholesterol Dibromide (pg. 582) | |
| E90. ~5-Cholestene-3-one from 5a,6p Dibromocholestane-3-one (pg. 583) | |
| E91. A4-Cholestene-3-one from A5-Cholestene-3-one (pg. 587) | |
| E92. Benzoin from Benzaldehyde (pg. 591) | |
| E93. Benzil from Benzoin (pg. 592) | |
| E94. Dibenzylketone from Phenylacetic Acid (pg. 593) | |
| E95. Tetraphenylcyclopentadienone from Benzil and Dibenzyl Ketone (pg. 595) | |
| E96. p-Acetamidobenzenesulfonyl Chloride from Acetanilide (pg. 602) | |
| E97. p-Acetamidobenzenesulfonamide from p-AcetamidobenzenesulfonylChloride (pg. 604) | |
| E98. Sulfanilamide from~Acetamidobenzenesulfonamide (pg. 605) | |
| E99. Ethyldioxyazobenzene from p-Phenetidine (pg. 608) | |
| E100. Diethyldioxyazobenzene from Ethyldioxyazobenzene (pg. 610) | |
| E1 01. p-Phenetidine from diethyldioxyazobenzene (pg. 611) | |
| E102. 2-Chloro-4-Bromoacetanilide from 4-Bromoacetanilide (pg. 617) | |
| E103. 2-Chloro-4-bromoaniline from 2-Chloro-4-bromoacetanilide (pg. 620) | |
| E104. 2-Ch loro-4-bromo-6-iodoani I i ne from 2-Chloro-4-bromoaniline (pg. 622) | |
| E105. 1-Bromo-3-Chloro-5-lodobenzene from 2-Chloro-4-Bromo-6-lodoaniline (pg. 624) | |
| E106. 1 ,4-Dimethylpyridinium Iodide from 4-Methylpyridine and Methyl Iodide (pg. 629) | |
| E107. Preparation of 4-(p-Hydroxystyryi)-1-Methylpyridinium Iodide from1 ,4-Dimethylpyridinium Iodide andp-Hydroxybenzaldehyde (pg. 630) | |
| E108. 1-Methyi-4-[(0xocyclohexadienylidene)Ethylidene]-1 ,4-Dihydropyridine(MOED) from 4-(p-Hydroxystyryi)-1-Methylpyridinium Iodide (pg. 632) | |
| Appendix (pg. 635) | |
| Chemical Substance Index (pg. 647) | |
| General Subject Index (pg. 655) | |
Addison Ault
Addison Ault is Professor Emeritus at Cornell College, where he taught in the chemistry department for fifty years before retiring in 2012. Professor Ault inspired generations of students and countless colleagues with his infectious joy and his passion for organic chemistry. He received his PhD in chemistry from Harvard University, and is the author or co-author of four books, including the 4th edition of Techniques and Experiments for Organic Chemistry.|
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