Organic Experiments

Ken Williamson retired from Mt. Holyoke College where he taught the organic chemistry laboratory course. He was an established authority on microscale techniques and regularly held workshops and traveled to campuses in the U.S., Canada, and Europe to demonstrate the use of microscale. Katherine Masters is a Teaching Professor of Chemistry, a Laboratory Director, and Assistant Head for Student Engagement at Penn State University. She has developed numerous courses, including two new lab experiences for undergraduates that focus on research in academia and in industry. Her passion is curriculum development—creating new and updated materials to better engage students in their learning.

• 1. Introduction.2. Laboratory Safety, Courtesy, and Waste Disposal.3. Melting Points and Boiling Points.4. Recrystallization.5. Distillation.6. Steam Distillation, Vacuum Distillation, and Sublimation.7. Extraction.8. Thin-Layer Chromatography: Analyzing Analgesics and Isolating Lycopene from Tomato Paste.9. Column Chromatography: Fluorenone, Cholesteryl Acetate, Acetylferrocene, and Plant Pigments.10. Gas Chromatography: Analyzing Alkene Isomers.11. Infrared Spectroscopy.12. Nuclear Magnetic Resonance Spectroscopy.13. Mass Spectrometry.14. Ultraviolet Spectroscopy, Refractive Indices, and Qualitative Instrumental Organic Analysis.15. Computational Chemistry.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.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.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.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.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 Bioassay 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.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. The 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. 1,4-Addition: Reductive Acetylation of Benzil.58. The Synthesis of an Alkyne from an Alkene; Bromination and Dehydrobromination: Stilbene and Diphenylacetylene.59. The Perkin Reaction: Synthesis of a-Phenylcinnamic Acid and Its Decarboxylation to cis-Stilbene.60. Multicomponent Reactions: The Aqueous Passerini Reaction.61. Chemiluminescence: Syntheses of Cyalume and Luminol.62. Photochemistry: The Synthesis of Benzopinacol.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.68. Searching the Chemical Literature.

1. Introduction. 2. Laboratory Safety, Courtesy, and Waste Disposal. 3. Melting Points and Boiling Points. 4. Recrystallization. 5. Distillation. 6. Steam Distillation, Vacuum Distillation, and Sublimation. 7. Extraction. 8. Thin-Layer Chromatography: Analyzing Analgesics and Isolating Lycopene from Tomato Paste. 9. Column Chromatography: Fluorenone, Cholesteryl Acetate, Acetylferrocene, and Plant Pigments. 10. Gas Chromatography: Analyzing Alkene Isomers. 11. Infrared Spectroscopy. 12. Nuclear Magnetic Resonance Spectroscopy. 13. Mass Spectrometry. 14. Ultraviolet Spectroscopy, Refractive Indices, and Qualitative Instrumental Organic Analysis. 15. Computational Chemistry. 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. 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. 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. 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. 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 Bioassay 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. 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. The 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. 1,4-Addition: Reductive Acetylation of Benzil. 58. The Synthesis of an Alkyne from an Alkene; Bromination and Dehydrobromination: Stilbene and Diphenylacetylene. 59. The Perkin Reaction: Synthesis of a-Phenylcinnamic Acid and Its Decarboxylation to cis-Stilbene. 60. Multicomponent Reactions: The Aqueous Passerini Reaction. 61. Chemiluminescence: Syntheses of Cyalume and Luminol. 62. Photochemistry: The Synthesis of Benzopinacol. 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. 68. Searching the Chemical Literature.