Techniques and Experiments For Organic Chemistry / Edition 6

by Addison Ault

Overview

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.

Product Details

ISBN-13:	2900935702766
Publication date:	08/12/1998
Pages:	600
Product dimensions:	6.50(w) x 1.50(h) x 9.50(d)

Table of Contents

PART 1. LABORATORY OPERATIONSPreface1.Safety2.Glassware Used in the Organic Chemistry Lab3.Cleaning Up4.Collection and Disposal of Waste5.TheLaboratory Notebook6.The Chemical Literature7.Tables8.Filtration9.Recrystallization10. Distillation11. Reduced-Pressure Distillation12. Distillation of Mixtures of Two Immiscible Liquids; Steam Distillation13. Sublimation14. Extraction by Solvents15. Chromatography16. Removal of Water17. Boiling Point18. Melting Point19. Density20. Index of Refraction21. Optical Activity22. Molecular Weight23. Solubility24. Infrared Absorption Spectrometry25. Ultraviolet-Visible Absorption Spectrometry26. Nuclear Magnetic Resonance Spectrometry27. Mass Spectrometry28. Qualitative Tests for the Elements29. Qualitative Characterization Tests: Tests for Functional Groups30. Characterization Through Formation of Derivatives31. Assembling the Apparatus32. Temperature Control33. Methods of Heating and Cooling34. Stirring35. Addition of Reagents36. Control of Evolved Gases37. Concentration38. Use of an Inert Atmosphere39. Working Up the ReactionPART 2. EXPERIMENTSIsolations and PurificationsE1. Isolation of Cholesterol from GallstonesE2. Isolation of Lactose from Powdered MilkE3. Isolation of Acetylsalicylic Acid from Aspirin TabletsE4. Isolation of Ibuprofen from Ibuprofen TabletsE5. Isolation of Caffeine from Tea and NoDozE6. Isolation of Piperine from Back PepperE7. Isolation of Trimyristin from NutmegE8. Isolation of Clove Oil from ClovesE9. Isolation of Eugenol from Clove OilE10. Isolation of (R)-(+)-Limonene from Grapefruit or Orange PeelEll. Isolation of (R)-(-)- or (S)-(+)-Carvone from Oil of Spearmint or Oil of CarawayE12. Resolution of alpha-Phenylethylamine by (R), (R)-(+)-Tartaric AcidTransformationsE13. Adamantane from endo-Tetrahydrodicyclopentadiene via the Thiourea ClathrateE14. cis-Dibenzoylethyelene from trans-1,2-DibenzoylethyleneE15. Cyclohexanol from CyclohexeneE16. Cyclohexanol from CyclohexanoneE17. Cyclohexene from CyclohexanolE18. Dehydration of 2-Methylcyclohexanol: A VariationE19. Cyclohexyl Bromide from CyclohexanolE20. Cyclohexanone from CyclohexanolE21. Addition of Dichlorocarbene to CyclohexeneE22. Addition of Dichlorocarbene to Styrene: A VariationE23. Addition of Dichlorocarbene to 1,5-Cyclooctadiene: Another VariationE24. Isoamyl Bromide from Isoamyl AlcoholE25. n-Butyl Bromide from n-Butyl Alcohol: A VariationE26. tert-Butyl Chloride from tert-Butyl AlcoholE27. tert-Amyl Chloride from tert-Amyl Alcohol: A VariationE28. Competitive Nucleophilic Substition of Butyl Alcohols by Bromide and Chloride IonE29. Kinetics of the Hydrolysis of tert-Butyl ChlorideE30. Isoamyl Acetate from Isoamyl Bromide and Potassium AcetateE31. Isoamyl Acetate from Isoamyl Alcohol and Acetic Acid; The Fischer EsterificationE32. Cholesteryl Benzoate from CholesterolE33. alpha-D-Glucose Pentaacetate from GlucoseE34.beta-D-Glucose Pentaacetate from GlucoseE35. Acetylation of Glucose in N-Methylimidazole: A VariationE36. Preparation of Methyl Benzoate, Oil of NiobeE37. Aliphatic Alcohols: Preparation by Grignard SynthesisE38. Preparation of Triphenylmethanol from BenzophenoneE39. Preparation of Triphenylmethanol from Methyl BenzoateE40. Preparation of Triphenylmethanol from Dimethyl CarbonateE41. Preparation of Aniline from NitrobenzeneE42. Acetanilide from AnilineE43. N,N-Diethyl-m-Toluamide from m-Toluic Acid; A Mosquito Repellent: "Off"E44. Methyl m-Nitrobenzoate from Methyl BenzoateE45. p-Bromoacetanilide from AcetanilideE46. 2,4-Dinitrobenzene from NitrobenzeneE47. 2,4-DinitroanilineE48. 2,4-DinitrophenylhydrazineE49. 2,4-DinitrodiphenylamineE50. 2,4-DinitrophenylpiperidineE51. 4-Substituted 2,4-Dinitrophenylanilines: A VariationE52. Benzenediazonium Cloride from AnilineE53. p-Nitrobenzenediazonium Sulfate from p-NitroanilineE54.Chlorobenzene from Benzenediazonium ChlorideE55. Acetylvanillin from VanillinE56. 5-Bromovanillin from VanillinE57. 5-Nitrovanillin from VanillinE58. Vanillin Oxime from VanillinE59. Vanillin Semicarbazone from VanillinE60. Vanillyl Alcohol from VanillinE61. Vanillideneacetone from VanillinE62. Benzenediazonium Chloride and beta-Naphthol: 1-Phenylazo-2-Naphthol (Sudan I)E63. p-Nitrobenzenediazonium Sulfate and Phenol: p-(4-nitrobenzeneazo)-phenolE64. 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-DimethylanilineE66. Butadiene (from 3-Sulfolene) and Maleic AnhydrideE67. Cyclopentadiene and Maleic AnhydrideE68. Furan and Maleic AnhydrideE69. alpha-Phellandrene and Maleic AnhydrideE70. The Preparation of trans-StilbeneE71. Preparation of trans,trans-1,4-Diphenylbutadiene: A VariationE72. Acetylsalicylic Acid from Salicylic Acid: Preparation of AspirinE73. p-Acetamidophenol from p-Aminophenol: Preparation of TylenolE74. p-Ethoxyacetanilide from p-Ethoxyaniline: Preparation of PhenacetinE75. p-Ethoxyacetanilide from p-Acetamidophenol: Another Preparation of PhenacetinE76. 2-Nitrophenacetin from PhenacetinE77. Preparation of Methyl Salicylate: Oil of WintergreenE78. 3-Nonenoic Acid from Heptaldehyde and Malonic AcidE79. Coconut Aldehyde from 3-Nonenoic AcidE80. Thiamine-Catalyzed Formation of Benzoin from BenzaldehydeE81. 1-Benzylnicotinamide Chloride from NicotinamideE82. 1-Benzyldihydronicotinamide f rom 1-Benzylnicotinamide ChlorideE83. Reduction of Malachite Green by 1-BenzyldihydronicotinamideE84. Dixanthylene from XanthoneE85. Dianthraquinone from Anthrone via 9-BromoanthroneE86. A Photochromic Compound: 2-(2,4-Dinitrobenzl)pyridineE87. A Chemiluminescent Compound: LuminolSynthetic SequencesE88. Cholesterol Dibromide from CholesterolE89. 5alpha, 6beta-Dibromocholestane-3-one from Cholesterol DibromideE90. delta5-Cholestene-3-one from 5alpha, 6beta-Dibromocholestane-3-oneE91. delta4-Cholestene-3-one from delta5-Cholestene-3-oneE92. Benzoin from BenzaldehydeE93. Benzil brom BenzoinE94. Dibenzylketone from Phenylacetic AcidE95. Tetraphenylcyclopentadienone from Benzil and Dibenzyl KetoneE96. p-Acetamidobenzenesulfonyl Chloride from AcetanilideE97. p-Acetamidobenzenesulfonamide from p-Acetamidobenzenesulfonyl ChlorideE98. Sulfanilamide from p-AcetamidobenzenesulfonamideE99. Ethyldioxyazobenzene from p-PhenetidineE100. Diethyldioxyazobenzene from EthyldioxyazobenzeneE101. p-Phenetidine from DiethyldioxyazobenzeneE102. 2-Chloro-4-Bromoacetanilide from 4-BromoacetanilideE103. 2-Chloro-4-bromoaniline from 2-Chloro-4-bromoacetanilideE104. 2-Chloro-4-bromo-6-iodoaniline from 2-Chloro-4-bromoanilineE105. 1-Bromo-3-Chloro-5-Iodobenzene from 2-Chloro-4-Bromo-6-IodoanilineE106. 1,4-Diemthylpyridinium Iodide from 4-Methylpyridine and Methyl IodideE107. Preparation of 4-(p-Hydroxystyryl)-1-Methylpyridinium Iodide from 1,4-Dimethylpyridinium Iodide and p-HydroxybenzaldehydeE108. 1-Methyl-4-{(Oxocyclohexadienylidene)-Ethylidene}-1,4-Dihydropyridine (MOED) from 4-(p-Hydroxystyryl)-1-Methylpyridinium IodideAppendicesGeneral Subject IndexChemical Substances Index

Editorial Reviews

Ault's text merits careful consideration by organic chemistry laboratory instructors.

Science Books & Films

Those familiar with previous edition of Addison Ault's book will be pleased to see that the sixth edition is still an excellent text for the introductory organic chemistry laboratory...Ault's book is full of experiments that use "interesting" compounds, compounds with which students are likely to be familiar. Those new to Ault's text will find a well written laboratory manual that clearly reflects that author's years of experience. It is thorough, describing all the common lab techniques in Part 1 and giving concise, well-written directions for experiments in Part 2. The experiments provide an excellent representation of all the important reactions in a typical course. In fact, for most types of reactions there are several experiments from which to choose. Most experiments are written at the few- to several-gram scale, so that waste is minimized, but the esthetics of organic chemistry is maintained... Ault's book is an excellent text.

Journal of Chemical Education

Embraced by the inside covers' periodic table of elements and table of solutions of acids, the new edition of this introductory text continues to describe laboratory operations in its first part, and experiments in the second. Revisions by Ault (Cornell U.) include detailed instructions for the disposal of waste, and experiments with more interesting compounds (e.g. seven reactions of vanillin, and isolating ibuprofin from ibuprofin tablets). Conscious of costs, microscale experiments are included but not to the point where minuscule amounts of material will preclude the aesthetic pleasure of watching crystals form or distillates collect. Annotation c. by Book News, Inc., Portland, Or.

Booknews