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.

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.

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

Introduction 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. 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. 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 andBioessay of Sulfanilamide and Derivatives 46. Dyes and Dyeing 47. Martius Yellow 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 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. Decarboxylation: Synthesis of cis-Stilbene Photochemistry 61. Chemiluminescence: Syntheses of Cyalume and Luminol 62. Photochemistry: The Synthesis of Benzopinacol 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 68. Searching the Chemical Literature