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Macroscale and Microscale Organic Experiments

Macroscale and Microscale Organic Experiments - 5th edition

Macroscale and Microscale Organic Experiments - 5th edition

ISBN13: 9780618590674

ISBN10: 0618590676

Macroscale and Microscale Organic Experiments by Kenneth Williamson, Robert Minard and Katherine M. Masters - ISBN 9780618590674
Cover type: Hardback
Edition: 5TH 07
Copyright: 2007
Publisher: Houghton Mifflin Harcourt
Published: 2007
International: No
Macroscale and Microscale Organic Experiments by Kenneth Williamson, Robert Minard and Katherine M. Masters - ISBN 9780618590674

ISBN13: 9780618590674

ISBN10: 0618590676

Cover type: Hardback
Edition: 5TH 07

List price: $120.00

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The market leader for the full-year organic laboratory, this manual derives many experiments and procedures from the classic Feiser lab text, giving it an unsurpassed reputation for solid, authoritative content. The Williamson/Minard/Masters manual's flexible mix of macroscale and microscale options for most experiments allows instructors to save on the purchase and disposal of expensive, sometimes hazardous organic chemicals. Macroscale versions can be used for less costly experiments, giving students experience working with conventionally sized glassware.

The Fifth Edition of the manual includes new experiments that stress greener chemistry, revised content in computational chemistry, and more information on laboratory safety procedures.

  • New! 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.
  • New! The laboratory safety chapter now includes material on working with closed systems and laboratory courtesy.
  • New! 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.
  • New! Bioassay experiments include a bioassay of eugenol isolated from cloves.
  • New! Material is now offered on diffuse reflectance IR analysis, capillary GC, and temperature programming.
  • Revised! The place of organic chemistry labwork has been put in a broader context via reorganization of and revisions to the first fifteen chapters dealing with basic lab methods, computational chemistry, and instrumental methods.
  • Revised! Computational chemistry, which allows students to determine the precise structure of molecules, has been extensively revised to provide extended coverage of ab initio and semi-empirical models and calculations.
  • Revised! The discussions of NMR theory and the interpretation of 1HNMR spectra have been updated.
  • The In this experiment... section appears before selected microscale experiments and presents the overarching objective of the experiment, keeping students from getting bogged down in the details of experimental procedures.
  • For Further Investigation procedures appear in selected experiments. These are optional, additional procedures that can be assigned to further explore the chemical principle being presented.
  • A Cleaning Up section appears at the end of every experiment and instructs students on how to dispose of all the by-products used in the experiment. Other pedagogical features include pre-lab exercises, marginal notes, clear line drawings, and end-of-chapter questions.

Table of Contents

Table of Contents

I. Introduction

1. Introduction
2. Laboratory Safety, Courtesy, and Waste Disposal

II. 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 Isolation of Lycopene from Tomato Paste
9. Column Chromatography Fluorenone, Acetylferrocene, Cholesteryl Acetate, 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 Chemistry
15. Computational Chemistry

III. 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

IV. Oxidation and Reduction

22. Oxidation Cyclohexanol to Cyclohexanone; Cyclohexanone to Adipic Acid
23. Pulegone from Citronellol Oxidation with Pyridinium Chlorochromate
24. Oxidative Coupling of Alkynes 2,7-Dimethyl-3,5-octadiyn-2,7-diol
25. Catalytic Hydrogenation
26. Borohydride Reduction of 2-Methylcyclohexanone A Problem in Conformational Analysis
27. Epoxidation of Cholesterol

V. 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. Reactions of Triphenylmethyl Carbocation, Carbanion, and Radical
32. The Friedel-Crafts Reaction Anthraquinone and Anthracene
33. Friedel-Crafts Acylation of Ferrocene Acetylferrocene
34. 1,2,3,4-Tetraphenylnaphthalene via Benzyne
35. Triptycene via Benzyne

VI. 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

VII. Reactions of Carboxylic Acids, Esters, and Amines

40. Esterification and Hydrolysis
41. Acetylsalicylic Acid (Aspirin)
42. Malonic Ester of a Barbiturate
43. Amines

VIII. Derivatives of 1,2-Diphenylethane A Multistep Process

44. The Sandmeyer Reaction 1-Bromo-4-chlorobenzene, 2-Iodobenzoic Acid, and 4-Chlorotoluene
45. Sulfanilamide from Nitrobenzene
46. Dyes and Dyeing
47. Martius Yellow

IX. The Diels-Alder and Related Reactions

48. Diels-Alder Reaction
49. Ferrocene [Bis(cyclopentadienyl)iron]
50. p-Terphenyl by the Diels-Alder Reaction
51. Tetraphenylcyclopentadienone
52. Hexaphenylbenzene and Dimethyl Tetraphenylphthalate

X. Derivatives of 1,2-Diphenylethane A Multistep Synthesis

53. The Benzoin Condensation Cyanide Ion and Thiamine Catalyzed
54. Nitric Acid Oxidation. Preparation of Benzil from Benzoin. Synthesis of a Heterocycle Diphenylquinoxaline
55. Borohydride Reduction of a Ketone Hydrobenzoin from Benzil
56. Synthesis of 2,2-Dimethyl-1,5-dioxolane. The Acetonide Derivative of a Vicinal Diol
57. 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 -Phenylcinnamic Acid
60. Decarboxylation Synthesis of cis-Stilbene

XI. Photochemistry

61. Chemiluminescence Syntheses of Cyalume and Luminol
62. Photochemistry The Synthesis of Benzopinacol

XII. Natural Product Chemistry and Biochemistry

63. Carbohydrates and Sweeteners
64. Biosynthesis of Ethanol
65. Enzymatic Reactions A Chiral Alcohol from a Ketone and Enzymatic Resolution of dl-Alanine
66. The Synthesis of Natural Products Pseudopellitierene and Camphor
67. Polymers Synthesis and Recycling

XIII. Searching the Chemical Literature

68. Searching the Chemical Literature

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