Techniques and Experiments
for Organic Chemistry

Sixth Edition

Addison Ault, Cornell College


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