Operational Organic Chemistry

To the Instructor.


Introduction.


Laboratory Safety.
I. MASTERING THE OPERATIONS.

1. Learning Basic Operations. The Effect of pH on a Food Preservative.
2. Extraction and Evaporation. Separating the Components of Panacetin.
3. Recrystallization and Melting Point Measurement. Identifying a Constituent of Panacetin.
4. Heating under Reflux. Synthesis of Salicylic Acid from Wintergreen Oil.
5. Simple Distillation, Gas Chromatography. Preparation of Synthetic Banana Oil.
6. Fractional Distillation. Separation of Petroleum Hydrocarbons.
7. Addition, Mixing, Sublimation. Preparation of Camphor.
8. Boiling Point, Refractive Index. Identification of a Petroleum Hydrocarbon.
9. Column Chromatography, UV-VIS Spectrometry. Isolation and Isomerization of Lycopene from Tomato Paste.
10. Steam Distillation, Infrared Spectrometry. Isolation and Identification of the Major Constituent of Clove Oil.
11. Thin-Layer Chromatography, NMR Spectrometry. Identification of Unknown Ketones.
12. Vacuum Distillation, Optical Rotation. Optical Activity of ...a-Pinene.
II. CORRELATED LABORATORY EXPERIMENTS.

13. Investigation of a Chemical Bond by Infrared Spectrometry.
14. Properties of Common Functional Groups.
15. Thin-Layer Chromatographic Analysis of Drug Components.
16. Separation of an Alkane Clathrate.
17. Isomers and Isomerization Reactions.
18. Structures and Properties of Stereoisomers.
19. Bridgehead Reactivity in an SN1 Solvolysis Reaction.
20. Reaction of Iodoethane with Sodium Saccharin, an Ambident Nucleophile.
21. Dehydration of Methylcyclohexanols.
22. Synthesis of 7,7-Dichloronorcarane Using a Phase-Transfer Catalyst.
23. Stereochemistry of the Addition of Bromine to trans-Cinnamic Acid.
24. Hydration of a Difunctional Alkyne.
25. Preparation of Bromotriphenylmethane and the Trityl Free Radical.
26. Chain-Growth Polymerization of Styrene and Methyl Methacrylate.
27. Synthesis of Ethanol by Fermentation.
28. The Reaction of Butanols with Hydrobromic Acid.
29. Borohydride Reduction of Vanillin.
30. Multistep Synthesis of Cyclopentanol from Cyclohexanol.
31. Synthesis of Triphenylmethanol and the Trityl Carbocation.
32. Identification of a Conjugated Diene from Eucalyptus Oil.
33. Spectral Identification of Terpenoids.
34. Synthesis and Spectral Analysis of Aspirin.
35. Preparation of Nonbenzenoid Aromatic Compounds.
36. Mechanism of the Nitration of Arenes by Nitronium Fluoborate.
37. Friedel-Crafts Acylation of Anisole.
38. Structure of a Natural Product in Anise Oil.
39. Identification of an Oxygen-Containing Organic Compound.
40. Wittig Synthesis of 1,4-Diphenyl-1,3-Butadiene.
41. Effect of Reaction Conditions on the Condensation of Furfural with Cyclopentanone.
42. Haloform Oxidation of 4'-Methoxyacetophenone.
43. Electronic Effect of a para-Iodo Substituent.
44. Synthesis and Identification of an Unknown Carboxylic Acid.
45. Preparation of the Insect Repellent N, N- Diethyl-m-Toluamide.
46. Synthesis of 2-Acetylcyclohexanone by the Stork Enamine Reaction.
47. Synthesis of Dimedone and Measurement of Its Tautomeric Equilibrium Constant.
48. Preparation of Para Red and Related Azo Dyes.
49. Reaction of Phthalimide with Sodium Hypochlorite.
50. Identification of an Unknown Amine.
51. Preparation and Mass Spectrum of 2-Phenylindole.
52. Nucleophilic Strength and Reactivity in SNAr Reactions.
53. Structure of an Unknown D-Hexose.
54. Fatty Acid Content of Commercial Cooking Oils.
55. Structure of an Unknown Dipeptide.
56. Multistep Synthesis of Benzilic Acid from Benzaldehyde.
57. Using the Chemical Literature in an Organic Synthesis.
58. A Research Project in Organic Chemistry.
III. MINILABS.

1. Making Useful Laboratory Items.
2. Extraction of Iodine by Dichloromethane.
3. Purification of an Unknown Compound by Recrystallization.
4. Developing and Testing a Hypothesis.
5. Preparation of Acetate Esters.
6. Gas Chromatographic Analysis of Commercial Xylene.
7. Isolation of Caffeine from No-Doz Tablets.
8. A Missing Label Puzzle.
9. Paper Chromatography of Dyes in Commercial Drink Mixes.
10. Gas Chromatographic Analysis of an Essential Oil from Orange Peel.
11. Identification of an Unknown Felt-Tip Pen Ink by TLC.
12. Optical Rotation of Turpentine.
13. The Structures of Organic Molecules.
14. Who Else Has My Compound?
15. Isomers and Molecular Structure.
16. Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions.
17. An SN1 Reaction of Bromotriphenylmethane.
18. Preparation and Properties of a Gaseous Alkene.
19. Addition of Iodine to ...a-Pinene.
20. Unsaturation in Commercial Products.
21. Free-Radical Bromination of Hydrocarbons.
22. The Nylon Rope Trick.
23. Nucleophilic Substitution Rates of Alcohols.
24. Photoreduction of Benzophenone to Benzopinacol.
25. Oxidation of Alcohols by Potassium Permanganate.
26. Preparation of a Fluorescent Dye.
27. Diels-Alder Reaction of Maleic Anhydride and Furan.
28. Identification of an Unknown Arene by NMR Spectrometry
29. Interpretation of a Mass Spectrum.
30. Nitration of Naphthalene.
31. Preparation of Trityl Cations by the Friedel-Crafts Reaction.
32. Air Oxidation of Fluorene to 9-Fluorenone.
33. A Nucleophilic Addition-Elimination Reaction of Benzil.
34. Preparation of Aldol Condensation Products.
35. A Spontaneous Reaction of Benzaldehyde.
36. Acid/Base Strengths of Organic Compounds.
37. Hydrolysis Rates of Esters.
38. Preparation of Benzamide.
39. Synthesis of Dimedone Derivatives of Benzaldehyde.
40. A Diazonium Salt Reaction of 2-Aminobenzoic Acid.
41. Beckmann Rearrangement of Benzophenone Oxime.
42. Dyeing with Indigo.
43. Reaction of Monosaccharides with Phenols.
44. Extraction of Trimyristin from Nutmeg.
45. Preparation of a Soap Using a Phase-Transfer Catalyst
46. Isolation of Protein from Milk.
IV. QUALITATIVE ORGANIC ANALYSIS.

An Overview of Qual Organic.
Preliminary Work.
Classification.
Spectral Analysis.
Identification.
Exercises.
V. THE OPERATIONS.

1. Cleaning and Drying Glassware.
2. Using Standard-Taper Glassware.
3. Using Glass Rod and Tubing.
4.Weighing.
5.Measuring Volume.
6. Heating.
7. Cooling.
8. Temperature Monitoring.
9. Mixing.
10. Addition of Reactants.
11. Gravity Filtration.
12. Vacuum Filtration.
13. Extraction.
14. Evaporation.
15. Steam Distillation.
16. Column Chromatography.
17. Thin-Layer Chromatography.
18. Paper Chromatography.
19. Washing Liquids.
20. Drying Liquids.
21. Drying Solids.
22. Drying and Trapping Gases.
23. Recrystallization.
24. Sublimation.
25. Simple Distillation.
26. Vacuum Distillation.
27. Fractional Distillation.
28. Melting Point.
29. Boiling Point.
30. Refractive Index.
31. Optical Rotation.
32. Gas Chromatography.
33. High Performance Liquid Chromatography.
34. Infrared Spectrometry.
35. Nuclear Magnetic Resonance Spectrometry.
36. Ultraviolet-Visible Spectrometry.
37. Mass Spectrometry.
APPENDIXES.

I. Laboratory Equipment.
II. Keeping a Laboratory Notebook.
III. Writing a Laboratory Report.
IV. Calculations for Organic Synthesis.
V. Planning an Experiment.
VI. Properties of Organic Compounds.
VII. The Chemical Literature.
Bibliography.
Index.