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Macroscale and Microscale Organic Experiments

By Kenneth L. Williamson, Katherine M. Masters

7th Edition © 2017
Discipline:Chemistry
Course:Organic Chemistry
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Now featuring new themed Modules experiments with real world applications, this Seventh Edition of the market leader for the full-year organic laboratory course derives many experiments and procedures from the classic Feiser lab text, giving it an unsurpassed reputation for solid, authoritative content. This proven manual offers a flexible mix of macroscale and microscale options for most experiments, emphasizing safety and allowing instructors to save on the purchase and disposal of expensive, sometimes hazardous, organic chemicals. Macroscale versions for less costly experiments allow students to get experience working with conventionally-sized glassware.

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About this product

Now featuring new themed Modules experiments with real world applications, this Seventh Edition of the market leader for the full-year organic laboratory course derives many experiments and procedures from the classic Feiser lab text, giving it an unsurpassed reputation for solid, authoritative content. This proven manual offers a flexible mix of macroscale and microscale options for most experiments, emphasizing safety and allowing instructors to save on the purchase and disposal of expensive, sometimes hazardous, organic chemicals. Macroscale versions for less costly experiments allow students to get experience working with conventionally-sized glassware.

GREENER CHEMISTRY. Experiments that stress greener chemistry appear throughout the manual and are identified with a green chemistry icon. For example, the use of household bleach is explored as an alternative to the toxic chromium ion as an oxidizing agent for cyclohexanol.

AN EMPHASIS ON LABORATORY SAFETY. The laboratory safety chapter includes material on working with closed systems and laboratory courtesy.

A STRONG MASS SPECTROMETRY CHAPTER. The chapter on mass spectrometry describes time-of-flight and mass quadrupole analyzers and includes sections on GC-MS and computer-aided spectral identification, as well as ESI and MALDI ionization.

BIOASSAY EXPERIMENTS. The manual's bioassay experiments include a bioassay of eugenol isolated from cloves.

Table of contents

Chapters

Cover Page
Title Page
Copyright Page
Dedication
Preface.
Acknowledgment
Organic Experiments and Waste Disposal
Chapter 1. Introduction*Preview this chapter
Chapter 2. Laboratory Safety, Courtesy, and Waste Disposal
Chapter 3. Melting Points and Boiling Points
Chapter 4. Recrystallization
Chapter 5. Distillation
Chapter 6. Steam Distillation, Vacuum Distillation, and Sublimation
Chapter 7. Extraction
Chapter 8. Thin-Layer Chromatography: Analyzing Analgesics and Isolating Lycopene from Tomato Paste
Chapter 9. Column Chromatography: Fluorenone, Cholesteryl Acetate, Acetylferrocene, and Plant Pigments
Chapter 10. Gas Chromatography: Analyzing Alkene Isomers
Chapter 11. Infrared Spectroscopy
Chapter 12. Nuclear Magnetic Resonance Spectroscopy
Chapter 13. Mass Spectrometry
Chapter 14. Ultraviolet Spectroscopy, Refractive Indices, and Qualitative Instrumental Organic Analysis
Chapter 15. Computational Chemistry
Chapter 16. The SN2 Reaction: 1-Bromobutane
Chapter 17. Nucleophilic Substitution Reactions of Alkyl Halides
Chapter 18. Radical Initiated Chlorination of 1-Chlorobutane
Chapter 19. Alkenes from Alcohols: Cyclohexene from Cyclohexanol
Chapter 20. Bromination and Debromination: Purification of Cholesterol
Chapter 21. Dichlorocarbene
Chapter 22. Oxidation: Cyclohexanol to Cyclohexanone; Cyclohexanone to Adipic Acid
Chapter 23. The Cannizzaro Reaction: Simultaneous Synthesis of an Alcohol and an Acid in the Absence of Solvent
Chapter 24. Oxidative Coupling of Alkynes: 2,7-Dimethyl-3,5-octadiyn-2,7-diol
Chapter 25. Catalytic Hydrogenation
Chapter 26. Sodium Borohydride Reduction of 2-Methylcyclohexanone: A Problem in Conformational Analysis
Chapter 27. Epoxidation of Cholesterol
Chapter 28. Nitration of Methyl Benzoate
Chapter 29. Friedel–Crafts Alkylation of Benzene and Dimethoxybenzene; Host-Guest Chemistry
Chapter 30. Alkylation of Mesitylene
Chapter 31. The Friedel–Crafts Reaction: Anthraquinone and Anthracene
Chapter 32. Friedel–Crafts Acylation of Ferrocene: Acetylferrocene
Chapter 33. Reactions of Triphenylmethyl Carbocation, Carbanion, and Radical
Chapter 34. 1,2,3,4-Tetraphenylnaphthalene via Benzyne
Chapter 35. Triptycene via Benzyne
Chapter 36. Aldehydes and Ketones
Chapter 37. Dibenzalacetone by the Aldol Condensation
Chapter 38. Grignard Synthesis of Triphenylmethanol and Benzoic Acid
Chapter 39. The Wittig and Wittig–Horner Reactions
Chapter 40. Esterification and Hydrolysis
Chapter 41. Acetylsalicylic Acid (Aspirin)
Chapter 42. Malonic Ester of a Barbiturate
Chapter 43. Amines
Chapter 44. The Sandmeyer Reaction: 1-Bromo-4-chlorobenzene, 2-Iodobenzoic Acid, and 4-Chlorotoluene
Chapter 45. Synthesis and Bioassay of Sulfanilamide and Derivatives
Chapter 46. Dyes and Dyeing
Chapter 47. Martius Yellow
Chapter 48. Diels–Alder Reaction
Chapter 49. Ferrocene [Bis(cyclopentadienyl)iron]
Chapter 50. A Diels–Alder Reaction Puzzle: The Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride
Chapter 51. Tetraphenylcyclopentadienone
Chapter 52. Hexaphenylbenzene and Dimethyl Tetraphenylphthalate
Chapter 53. The Benzoin Condensation: Catalysis by the Cyanide Ion and Thiamine
Chapter 54. Nitric Acid Oxidation; Preparation of Benzil from Benzoin; and Synthesis of a Heterocycle: Diphenylquinoxaline
Chapter 55. The Borohydride Reduction of a Ketone: Hydrobenzoin from Benzil
Chapter 56. The Synthesis of 2,2-Dimethyl-1,5-Dioxolane: The Acetonide Derivative of a Vicinal Diol
Chapter 57. 1,4-Addition: Reductive Acetylation of Benzil
Chapter 58. The Synthesis of an Alkyne from an Alkene by Bromination and Dehydrobromination: Stilbene and Diphenylacetylene
Chapter 59. The Perkin Reaction: Synthesis of α-Phenylcinnamic Acid and Its Decarboxylation to cis-Stilbene
Chapter 60. Multicomponent Reactions: The Aqueous Passerini Reaction
Chapter 61. Chemiluminescence: Syntheses of Cyalume and Luminol
Chapter 62. Photochemistry: The Synthesis of Benzopinacol
Chapter 63. Carbohydrates and Sweeteners
Chapter 64. Virstatin, a Possible Treatment for Cholera
Chapter 65. Biosynthesis of Ethanol and Enzymatic Reactions
Chapter 66. The Synthesis of Natural Products: The Sex Attractant of the Cockroach and Camphor
Chapter 67. Polymers: Synthesis and Recycling
Agricultural Science Module
Food Science Module
Textile Module
Forensics Module
Chrysanthemic Acid: A Team Project
Writing Module
Chapter 68. Searching the Chemical Literature
Show more

Chapter 1. IntroductionPreview this chapter ↗

Experimental Organic Chemistry
Preview this section ↗
Experimental Organic Chemistry ↗
Equipment for Experimental Organic Chemistry ↗
Check-In of Lab Equipment ↗
Transfer of Liquids and Solids ↗
Weighing and Measuring ↗
Tares ↗
Washing and Drying Laboratory Equipment ↗
Miscellaneous Cleanup ↗
The Laboratory Notebook ↗

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