Includes indexes.

pt. 1. Introduction to basic laboratory techniques -- 1. Introduction to microscale laboratory -- 2. Solubility -- 3. Crystallization -- 3A. Semimicroscale crystallization, Erlenmeyer flask and Hirsch funnel -- 3B. Microscale crystallization, Craig tube -- 3C. Selecting a solvent to crystallize a substance -- 3D. Mixture melting points -- 3E. Critical thinking application -- 4. Extraction -- 4A. Extraction of caffeine -- 4B. Distribution of a solute between two immiscible solvents -- 4C. How do you determine which one is the organic layer? -- 4D. Use of extraction to isolate a neutral compound from a mixture containing an acid or base impurity -- 4E. Critical thinking application -- 5. Chromatography -- 5A. Thin-layer chromatography -- 5B. Selecting the correct solvent for thin-layer chromatography -- 5C. Monitoring a reaction with thin-layer chromatography -- 5D. Column chromatography -- 6. Simple and fractional distillation -- 6A. Simple and fractional distillation (semimicroscale procedure) -- 6B. Simple and fractional distillation (microscale procedure) -- 7. Infrared spectroscopy and boiling-point determination -- Essay : aspirin -- 8. Acetylsalicylic acid -- Essay : analgesics -- 9. Isolation of the active ingredient in an analgesic drug --

10 Acetaminophen -- 10A. Acetaminophen (microscale procedure) -- 10B. Acetaminophen (semimicroscale procedure) -- Essay : identification of drugs -- 11. TLC analysis of analgesic drugs -- Essay : caffeine -- 12. Isolation of caffeine from tea or coffee -- 12A. Extraction of caffeine from tea with methylene chloride -- 12B. Extraction of caffeine from tea or coffee using solid phase extraction (SPE) -- Essay : esters, flavors and fragrances -- 13. Isopentyl acetate (banana oil) -- 13A. Isopentyl acetate (microscale procedure) -- 13B. Isopentyl acetate (semimicroscale procedure) -- Essay : terpenes and phenylpropanoids -- 14. Essential oils : extraction of oil of cloves by steam distillation and liquid carbon dioxide -- 14A. Oil of cloves (microscale procedure) -- 14B. Oil of cloves (semimicroscale procedure) -- 14C. Extraction of oil of cloves with liquid carbon dioxide, a demonstration -- Essay : stereochemical theory of odor -- 15. Spearmint and caraway oil : (+)- and (-)-carvones -- Essay : the chemistry of vision -- 16. Isolation of chlorophyll and carotenoid pigments from spinach -- Essay : ethanol and fermentation chemistry -- 17. Ethanol from sucrose --

pt. 2. Introduction to molecular modeling -- Essay : molecular modeling and molecular mechanics -- 18. An introduction to molecular modeling -- 18A. The conformation of n-butane : local minima -- 18B. Cyclohexane chair and boat conformations -- 18C. Substituted cyclohexane rings -- 18D. cis- and trans-2-butene -- Essay : computational chemistry, ab Initio and semiempirical methods -- 19. Computational chemistry -- 19A. Heats of formation : isomerism, tautomerism, and regioselectivity -- 19B. Heats of reaction : SN1 reaction rates -- 19C. Density-electrostatic potential maps, acidities of caboxylic acids -- 19D. Density-electrostatic potential maps : carbocations -- 19E. Density-LUMO maps : reactivities of carbonyl groups --

pt. 3. Properties and reactions of organic compounds -- 20. Reactivities of some alkyl halides -- 21. Nucleophilic substitution reactions : competing nucleophiles -- 21A. Competitive nucleophiles with 1-butanol or 2-butanol -- 21B. Competitive nucleophiles with 2-methyl-2-propanol -- 21C. Analysis -- 22. Hydrolysis of some alkyl chlorides -- 23. Synthesis of n-butyl bromide and t-pentyl chloride -- 23A. n-butyl bromide -- 23B. N-butyl bromide (semimicroscale procedure) -- 23C. t-pentyl chloride (microscale procedure) -- 23D. t-pentyl chloride (semimicroscale procedure) -- 23E. t-pentyl chloride (macroscale procedure)-- 24. Elimination reactions : dehydration and dehydrohalogenation -- 24A. Dehydration of 1-butanol and 2-butanol -- 24B. Dehydrobromination of 1-bromobutane and 2-bromobutane -- 25. 4-methylcyclohexene -- 25A. 4-methylcyclohexene (microscale procedure) -- 25B. 4-methylcyclohexene (semimicroscale) -- 26. Phase-transfer catalysis : addition of dichlorocarbene to cyclohexene -- 27. Relative reactivities of several aromatic compounds -- 28. Nitration of methyl benzoate -- Essay : fats and oils -- 29. Methyl stearate from methyl oleate -- Essay : soaps and detergents --

30. Preparation of soap -- 31. Preparation of a detergent -- Essay : petroleum and fossil fuels -- 32. Gas-chromatographic analysis of gasolines -- Essay : green chemistry -- 33. Chiral reduction of ethyl acetoacetate ; optical purity determination -- 33A. Chiral reduction of ethyl acetoacetate -- 33B. NMR determination of the optical purity of ethyl (S)-3-hydroxybutanoate -- 34. Nitration of aromatic compounds using a recyclable catalyst -- 35. An oxidation-reduction scheme : borneol, camphor, isoborneol -- 36. Multistep reaction sequences : the conversion of benzaldehyde to benzilic acid -- 36A. Preparation of benzoin by thiamine catalysis -- 36B. Preparation of benzil -- 36C. Preparation of benzilic acid -- 37. Tetraphenylcyclopentadienone -- 38. Triphenylmethanol and benzoic acid -- 38A. Triphenylmethanol -- 38B. Benzoic acid -- 39. Aqueous-based organozinc reactions -- 40. Resolution of (±)-(alpha)-phenylethylanime and determination of optical purity -- 40A. Resolution of (±)-(alpha)-phenylethylanime -- 40B. Determination of optical purity using NMR and a chiral resolving agent -- 41. The aldol condensation reaction : preparation of benzalacetophenones (chalcones) --

42. Preparation of an (alpha), (beta)-unsaturated ketone via Michael and aldol condensation reactions -- 43. Enamine reactions : 2-acetylcyclohexanone -- 44. 1,4-diphenyl-1,3-butadiene --- 44A. Benzyltriphenylphosphonium chloride (Wittig salt) -- 44B. Preparation of 1,4-diphenyl-1,3-butadiene using sodium ethoxide to generate the ylide -- 44C. Preparation of 1,4-diphenyl-1,3-butadiene using potassium phosphate to generate the ylide - Essay : local anesthetics -- 45. Benzocaine -- 46. Methyl salicylate (oil of wintergreen) -- Essay : pheromones : insect attractants and repellents -- 47. N,N-diethyl-m-toluamide : the insect repellent "OFF" -- Essay : sulfa drugs -- 48. Sulfa drugs : preparation of sulfanilamide -- Essay : polymers and plastics -- 49. Preparation and properties of polymers : polyester, nylon, and polystyrene -- 49A. Polyesters -- 49B. Polyamide (nylon) -- 49C. Polystyrene -- 49D. Infrared spectra of polymer samples -- Essay : Diels-Alder reaction and insecticides -- 50. The Diels-Alder reaction of cyclopentadiene with maleic anhydride -- 51. Photoreduction of benzophenone and rearrangement of benzpinacol to benzopinacolone -- 51A. Photoreduction of benzophenone -- 51B. Synthesis of (beta)-benzopinacolone : the acid-catalyzed rearrangement of benzpinacol -- Essay : fireflies and photochemistry -- 52. Luminol -- Essay : the chemistry of sweeteners -- 53. Analysis of a diet soft drink by HPLC --

pt. 4. Identification of organic substances -- 54. Identification of unknowns -- 54A. Solubility tests -- 54B. Tests for the elements (N, S, X) -- 54C. Tests for unsaturation -- 54D. Aldehydes and ketones -- 54E. Carboxylic acids -- 54F. Phenols -- 54G. Amines -- 54H. Alcohols -- 54I. Esters --

pt. 5. Project-based experiments -- 55. A separation and purification scheme -- 56. Preparation of a C-4 or C-5 acetate ester -- 57. Extraction of essential oils from caraway, cinnamon, cloves, cumin, or fennel by steam distillation -- 57A. Isolation of essential oils by steam distillation -- 57B. Identification of the constituents of essential oils by gas chromatography-mass spectrometry -- 57C. Investigation of the essential oils of herbs and spices, a mini-research project -- 58. Competing nucleophiles in SN1 and SN2 reactions : investigations using 2-pentanol and 3-pentanol -- 59. Friedel-crafts acylation -- 60. The analysis of antihistamine drugs by gas chromatography-mass spectrometry -- 62. The use of organozinc reagents in synthesis : an exercise in synthesis and structure proof by spectroscopy -- 62. The aldehyde enigma -- 63. Synthesis of substituted chalcones : a guided-inquiry experience -- 64. Michael and aldol condensation reactions -- 65. Esterification reactions of vanillin : the use of NMR to solve a structure proof problem -- 66. An oxidation puzzle --

pt. 6. The techniques -- 1. Laboratory safety -- 2. The laboratory notebook, calculations, and laboratory records -- 3. Laboratory glassware : care and cleaning -- 4. How to find data for compounds : handbooks and catalogs -- 5. Measurement of volume and weight -- 6. Heating and cooling methods -- 7. Reaction methods -- 8. Filtration -- 9. Physical constants of solids : the melting point -- 10. Solubility -- 11. Crystallization : purification of solids -- 12. Extractions, separations, and drying agents -- 13. Physical constants of liquids : the boiling point and density -- 14. Simple distillation -- 15. Fractional distillation, azeotropes -- 16. Vacuum distillation, manometers -- 17. Sublimation -- 18. Steam distillation -- 19. Column chromatography -- 20. Thin-layer chromatography -- 21. High-performance liquid chromatography (HPLC) -- 22. Gas chromatography -- 23. Polarimetry -- 24. Refractometry -- 25. Infrared spectroscopy -- 26. Nuclear magnetic resonance spectroscopy (Proton NMR) -- 27. Carbon-13 nuclear magnetic resonance spectroscopy -- 28. Mass spectroscopy -- 29. Guide to the chemical literature --

Appendices -- 1. Tables of unknowns and derivatives -- 2. Procedures for preparing derivatives -- 3. Index of spectra.