A Microscale Approach to Organic Laboratory Techniques

PART I: INTRODUCTION TO BASIC LABORATORY TECHNIQUES.
Experiment 1: Introduction to Microscale Laboratory.
Experiment 2: Solubility.
Experiment 3: Crystallization.
Experiment 4: Extraction.
Experiment 5: A Separation and Purification Scheme.
Experiment 6: Chromatography.
Experiment 7: Simple and Fractional Distillation.
Experiment 8: Infrared Spectroscopy and Boiling Point Determination.
ESSAY: Aspirin.
Experiment 9: Acetylsalicylic Acid.
ESSAY: Analgesics.
Experiment 10: Isolation of the Active Ingredient in an Analgesic Drug.
Experiment 11: Acetaminophen.
ESSAY: Identification of Drugs.
Experiment 12: TLC Analysis of Analgesic Drugs.
ESSAY: Caffeine.
Experiment 13: Isolation of Caffeine.
ESSAY: Esters -- Flavors and Fragrances.
Experiment 14: Isopentyl Acetate (Banana Oil).
ESSAY: Terpenes and Phenylpropanoids.
Experiment 15: Essential Oils: Extraction of Oil of Cloves by Steam Distillation.
Essay: Stereochemical Theory of Odor.
Experiment 16: Spearmint and Caraway Oil: (+)- and (-)- Carvones.
Essay: The Chemistry of Vision.
Experiment 17: Isolation of Chlorophyll and Carotenoid Pigments from Spinach.
Essay: Ethanol and Fermentation Chemistry.
Experiment 18 Ethanol from Sucrose.
PART II: INTRODUCTION TO MOLECULAR MODELING.
ESSAY: Molecular Modeling and Molecular Mechanics.
Experiment 19: An Introduction to Molecular Modeling.
ESSAY: Computational Chemistry -- Ab initio and Semiempirical Methods.
Experiment 20: Computational Chemistry.
PART III: PROPERTIES AND REACTIONS OF ORGANIC COMPOUNDS.
Experiment 21: Reactivities of Some Alkyl Halides.
Experiment 22: Nucleophilic Substitution Reactions: Competing Nucleophiles.
Experiment 23: Synthesis of n-Butyl Bromide and t-Pentyl Chloride.
Experiment 24: 4-Methylcyclohexene.
ESSAY: Fats and Oils.
Experiment 25: Methyl Stearate from Methyl Oleate.
ESSAY: Petroleum and Fossil Fuels.
Experiment 26: Gas Chromatographic Analysis of Gasolines.
ESSAY: Biofuels.
Experiment 27: Biodiesel.
ESSAY: Green Chemistry.
Experiment 28: Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination Using a Chiral Shift Reagent.
Experiment 29: Nitration of Aromatic Compounds Using a Recyclable Catalyst.
Experiment 30: Resolution of (Phenylethylamine and Determination of Optical Purity.
Experiment 31: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol.
Experiment 32: Multi-Step Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid.
Experiment 33: Triphenylmethanol and Benzoic Acid.
Experiment 34: Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium Catalyst.
Experiment 35: Grubbs-Catalyzed Metathesis of Eugenol with 1,4-Butanediol to Prepare a Natural Product.
Experiment 36: Aqueous-based Organozinc Reactions.
Experiment 37: The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones).
Experiment 38: Preparation of an -Unsaturated Ketone via Michael and Aldol Condensation Reactions.
Experiment 39: The Wittig Reaction: Preparation of 1,4-Diphenyl-1,3-butadiene.
Experiment 40: Relative Reactivities of Several Aromatic Compounds.
Experiment 41: Nitration of Methyl Benzoate.
ESSAY: Local Anesthetics.
Experiment 42: Benzocaine.
Experiment 43: Methyl Salicylate (Oil of Wintergreen).
ESSAY: Pheromones: Insect Attractants and Repellents.
Experiment 44: N,N-Diethyl-m-toluamide: The Insect Repellent \"OFF.\"
ESSAY: Sulfa Drugs.
Experiment 45: Sulfa Drugs: Preparation of Sulfanilamide.
Essay: Polymers and Plastics.
Experiment 46: Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene.
Essay: Diels-Alder Reactions and Insecticides.
Experiment 47: The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride.
Experiment 48: Diels-Alder Reaction with Anthracene-9-methanol.
Experiment 49: Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone.
ESSAY:Fireflies and Photochemistry.
Experiment 50: Luminol.
ESSAY: The Chemistry of Sweeteners.
Experiment 51: Analysis of a Diet Soft Drink by HPLC.
PART IV: IDENTIFICATION OF ORGANIC SUBSTANCES.
Experiment 52: Identification of Unknowns.
PART V: PROJECT-BASED EXPERIMENTS.
Experiment 53: Preparation of a C-4 or C-5 Acetate Ester.
Experiment 54: Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, Fennel, or Star Anise.
Experiment 55: Competing Nucleophiles in SN1 and SN2 Reactions: Investigations using 2-Pentanol and 3-Pentanol.
Experiment 56: Friedel-Crafts Acylation.
Experiment 57: The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry.
Experiment 58: The Use of Organozinc Reagents in Synthesis: An Exercise in Synthesis and Structure Proof by Spectroscopy.
Experiment 59: Synthesis of Naproxen by Palladium Catalysis.
Experiment 60: The Aldehyde Enigma.
Experiment 61: Synthesis of Substituted Chalcones: A Guided-Inquiry Experience.
Experiment 62: Green Epoxidation of Chalcones.
Experiment 63: Cyclopropanation of Chalcones.
Experiment 64: Michael and Aldol Condensation Reactions.
Experiment 65: Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem.
Experiment 66: An Oxidation Puzzle.
PART VI: THE TECHNIQUES.
Technique 1: Laboratory Safety.
Technique 2: The Laboratory Notebook, Calculations, and Laboratory Records.
Technique 3: Laboratory Glassware: Care and Cleaning.
Technique 4: How to Find Data for Compounds: Handbooks and Catalogues.
Technique 5: Measurement of Volume and Weight.
Technique 6: Heating and Cooling Methods.
Technique 7: Reaction Methods.
Technique 8: Filtration.
Technique 9: Physical Constants of Solids: The Melting Point.
Technique 10: Solubility.
Technique 11: Crystallization: Purification of Solids.
Technique 12: Extractions, Separations, and Drying Agents.
Technique 13: Physical Constants of Liquids: The Boiling Point and Density.
Technique 14: Simple Distillation.
Technique 15: Fractional Distillation, Azeotropes.
Technique 16: Vacuum Distillation, Manometers.
Technique 17: Sublimation.
Technique 18: Steam Distillation.
Technique 19: Column Chromatography.
Technique 20: Thin-Layer Chromatography.
Technique 21: High-Performance Liquid Chromatography (HPLC).
Technique 22: Gas Chromatography.
Technique 23: Polarimetry.
Technique 24: Refractometry.
Technique 25: Infrared Spectroscopy.
Technique 26: Nuclear Magnetic Resonance Spectroscopy.
Technique 27: Carbon-13 Nuclear Magnetic Resonance Spectroscopy
Technique 28: Mass Spectrometry.
Technique 29: Guide to the Chemical Literature.
APPENDICES:
Appendix 1: Tables of Unknowns and Derivatives.
Appendix 2: Procedures for Preparing Derivatives.
Appendix 3: Index of Spectra.