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Macroscale and Microscale Organic Experiments 7th Edition

Kenneth L. Williamson | Katherine M. Masters

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  • ISBN-10: 1305884191
  • ISBN-13: 9781305884199
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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.

Kenneth L. Williamson, Mount Holyoke College, Emeritus

Ken Williamson is retired from Mt. Holyoke College where he taught the organic chemistry laboratory course. He is an established authority on microscale techniques and regularly holds workshops and travels to campuses in the U.S., Canada, and Europe to demonstrate the use of microscale.

Katherine M. Masters, Pennsylvania State University

A PhD from Pennsylvania State University, Katherine Masters is director of the organic chemistry laboratory courses at Penn State.

Created by teaching chemists, OWLv2 is a powerful online learning system for chemistry with a unique Mastery Learning approach, which allows students to practice at their own pace, receive meaningful feedback and access a variety of learning resources to help them master chemistry and achieve better grades.

Learn about OWLv2!
  • 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.
  • COMPREHENSIVE COVERAGE. Material is offered on diffuse reflectance IR analysis, capillary GC, and temperature programming.
  • PREMIUM WEBSITE. A Premium Website includes glassware-specific videos with pre-lab, gradable exercises.

Macroscale and Microscale Organic Experiments


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

Cengage provides a range of supplements that are updated in coordination with the main title selection. For more information about these supplements, contact your Learning Consultant.


Online Instructor's Resource Manual

ISBN: 9781305884120
Available on the Instructor’s Companion Website, this Instructor’s Resource Manual provides a variety of additional resources

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