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Introduction.WELCOME TO ORGANIC CHEMISTRY.Laboratory Safety. Organization of the Textbook. Advance Preparation. Budgeting Time. Purpose.
Part One: 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 Catalogs.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 (Proton NMR).Technique
27: Carbon-13 Nuclear Magnetic Resonance Spectroscopy.Technique
28: 6 Mass Spectrometry.Technique
29: Guide to the Chemical Literature.
Part Two: Introduction to Basic Laboratory Techniques.Experiment
1: Solubility.Experiment
2: Crystallization.Experiment
3: Extraction.Experiment
4: A Separation and Purification Scheme.Experiment 4A: Extractions with a Separatory Funnel.Experiment
5: Chromatography.Experiment 5A: Thin-Layer Chromatography.Experiment 5B: Selecting the Correct Solvent for Thin-Layer Chromatography.Experiment 5C: Monitoring a Reaction with Thin Layer Chromatography.Experiment 5D: Column Chromatography.Experiment
6: Simple and Fractional Distillation.Experiment
7: Infrared Spectroscopy and Boiling-Point Determination.Experiment
8: Acetylsalicylic Acid.Experiment
9: Acetaminophen.Experiment
10: TLC Analysis of Analgesic Drugs.Experiment
11: Isolation of Caffeine.Experiment 11A: Extraction of Caffeine from Tea.Experiment 11B: Isolation of Caffeine from a Tea Bag.Experiment
12: Isopentyl Acetate (Banana Oil).Experiment
13: Isolation of Eugenol from Cloves.Experiment
14: Spearmint and Caraway Oil: (+)- and (-)-Carvones.Experiment
15: Isolation of Chlorophyll and Carotenoid Pigments from Spinach.Experiment
16: Ethanol from Sucrose.
Part Three: Introduction to Molecular Modeling.Experiment
17: An Introduction to Molecular Modeling.Experiment 17A: The Conformations of n-Butane: Local Minima.Experiment 17B: Cyclohexane Chair and Boat Conformations.Experiment 17C: Substituted Cyclohexane Rings (Critical Thinking Exercise).Experiment 17D: cis- and trans-2-Butene.Experiment
18: Computational Chemistry.Experiment 18A: Heats of Formation: Isomerism, Tautomerism, and Regioselectivity.Experiment 18B: Heats of Reaction: SN1 Reaction Rates.Experiment 18C: Density-Electrostatic Potential Maps: Acidities of Carboxylic Acids.Experiment 18D: Density-Electrostatic Potential Maps: Carbocations.Experiment 18E: Density-LUMO Maps: Reactivities of Carbonyl Groups.
Part Four: Preparations and Reactions of Organic Compounds.Experiment
19: Reactivities of Some Alkyl Halides.Experiment
20: Nucleophilic Substitution Reactions: Competing Nucleophiles.Experiment 20A: Competitive Nucleophiles with 1-Butanol or 2-Butanol.Experiment 20B: Competitive Nucleophiles with 2-Methyl-2-Propanol.Experiment 20C: Analysis.Experiment
21: Synthesis of n-Butyl Bromide and t-Pentyl Chloride.Experiment 21A: n-Butyl Bromide.Experiment 21B: t-Pentyl Chloride.Experiment
22: 4-Methylcyclohexene.Experiment
23: Methyl Stearate from Methyl Oleate.Experiment
24: Gas-Chromatographic Analysis of Gasolines.Experiment
25: Biodiesel.Experiment 25A: Biodiesel from Coconut Oil.Experiment 25B: Biodiesel from Other Oils.Experiment 25C: Analysis of Biodiesel.Experiment
26: Ethanol from Corn.Experiment
27: Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination.Experiment 27A: Chiral Reduction of Ethyl Acetoacetate.Experiment 27B: NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate.Experiment
28: Nitration of Aromatic Compounds Using a Recyclable Catalyst.Experiment
29: Reduction of Ketones Using Carrots as Biological Reducing Agents.Experiment
30: Resolution of (±)-a-Phenylethylamine and Determination of Optical Purity.Experiment 30A: Resolution of (±)-a-Phenylethylamine.Experiment 30B: Determination of Optical Purity Using NMR and a Chiral Resolving Agent.Experiment
31: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol.Experiment
32: Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid.Experiment 32A: Preparation of Benzoin by Thiamine Catalysis.Experiment 32B: Preparation of Benzil.Experiment 32C: Preparation of Benzilic Acid.Experiment
33: Triphenylmethanol and Benzoic Acid.Experiment 33A: Triphenylmethanol.Experiment 33B: Benzoic Acid.Experiment
34: Aqueous-Based Organozinc Reactions.Experiment
35: Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes using a Palladium Catalyst.Experiment
36: Grubbs Catalyzed Metathesis of Eugenol with 1,4-Butenediol to Prepare a Natural Product.Experiment
37: The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones).Experiment
38: A Green Enantioselective Aldol Condensation Reaction.Experiment
39: Preparation of an a,b-Unsaturated Ketone via Michael and Aldol Condensation Reactions.Experiment
40: Preparation of Triphenylpyridine.Experiment
41: 1,4-Diphenyl-1,3-Butadiene.Experiment
42: Relative Reactivities of Several Aromatic Compounds.Experiment
43: Nitration of Methyl Benzoate.Experiment
44: Benzocaine.Experiment
45: N,N-Diethyl-m-toluamide: The Insect Repellent OFF".Experiment
46: Sulfa Drugs: Preparation of Sulfanilamide.Experiment
47: Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene.Experiment 49A: Polyesters.Experiment 49B: Polyamide (Nylon).Experiment 49C: Polystyrene.Experiment 49D: Infrared Spectra of Polymer Samples.Experiment
48: Ring-Opening Metathesis Polymerization (ROMP) Using a Grubbs Catalyst: A Three-Step Synthesis of a Polymer.Experiment 48A: Diels-Alder Reaction of Furan and Maleic Anhydride.Experiment 48B: Ring Opening of Anhydride in Methanol.Experiment 48C: Ring-Opening Metathesis Polymerization (ROMP).Experiment 48A: Diels-Adler Reaction.Experiment 48B: Conversion of the Diels-Adler Adduct to the Diester.Experiment 48C: Synthesizing the Polymer by Ring-Opening Metathesis Polymerization (ROMP).Experiment
49: The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride.Experiment
50: Diels-Alder Reaction with Anthracene-9-methanol.Experiment
51: Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone.Experiment 51A: Photoreduction of Benzophenone.Experiment 51B: Synthesis of b-Benzpinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol.Experiment
52: Luminol.Experiment
53: Analysis of A Diet Soft Drink by HPLC.Experiment
54: Carbohydrates.
Part Four: Identification of Organic Substances.Experiment
55: Identification of Unknowns.Experiment 55A: Solubility Tests.Experiment 55B: Tests of the Elements (N, S, X).Experiment 55C: Tests for Unsaturation.Experiment 55D: Aldehydes and Ketones.Experiment 55E: Carboxylic Acids.Experiment 55F: Phenols.Experiment 55G: Amines.Experiment 55H: Alcohols.Experiment 55I: Esters.
Part Six: Project-Based Experiments.Experiment
56: Preparation of a C-4 or C-5 Acetate Ester.Experiment
57: Isolation of Essential Oils from Allspice, Caraway, Cinnamon, Cloves, Cumin, Fennel, or Star Anise.Experiment 57A: Isolation of Essential Oils by Steam Distillation.Experiment 57B: Identification of the Constituents of Essential Oils by Gas Chromatography-Mass Spectrometry.Experiment 57C: Investigation of the Essential Oils of Herbs and Spices--A Mini-Research Project.Experiment
58: Competing Nucleophiles in SN1 and SN2 Reactions: Investigations Using 2-Pentanol and 3-Pentanol.Experiment
59: Friedel-Crafts Acylation.Experiment
60: The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry.Experiment
61: Carbonation of an Unknown Aromatic Halide.Experiment 62 The Aldehyde Enigma.Experiment 63 Synthesis of Substituted Chalcones: A Guided-Inquiry Experience.Experiment
64: Green Epoxidation of Chalcones.Experiment
65: Cyclopropanation Reactions on Chalcones.Experiment
66: Michael and Aldol Condensation Reactions.Experiment
67: Esterification Reactions of Vanillin: The Use of NMR to Determine at Structure.Experiment
68: An Oxidation Puzzle.
Part Seven: Essays.Essay
1: Aspirin.Essay
2: Analgesics.Essay
3: Identification of Drugs.Essay
4: Caffeine.Essay
5: Esters--Flavors and Fragrances.Essay
6: Terpenes and Phenylpropanoids.Essay
7: Stereochemical Theory of Odor.Essay
8: The Chemistry of Vision.Essay
9: Ethanol and Fermentation Chemistry.Essay
10: Molecular Modeling and Molecular Mechanics.Essay
11: Computational Chemistry--ab Intio and Semiempirical Methods.Essay
12: Fats and Oils.Essay
13: Petroleum and Fossil Fuels.Essay
14: Biofuels.Essay
15: Green Chemistry.Essay
16: Local Anesthetics.Essay
17: Pheromones: Insect Attractants.Essay
18: Sulfa Drugs.Essay
19: Polymers and Plastics.Essay
20: Diels-Alder Reaction and Insecticides.Essay
21: Fireflies and Photochemistry.Essay
22: The Chemistry of Sweeteners.Appendices.Appendix
1: Tables of Unknowns and Derivatives.Appendix
2: Procedures for Preparing Derivatives.Appendix 3 Index of Spectra."