Introduction to Organic Laboratory Techniques : A Small Scale Approach
by Pavia, Donald L.; Lampman, Gary M.; Kriz, George S.; Engel, Randall G.Edition: 2nd
Format: Hardcover
Pub. Date: 2004-03-12
Publisher(s): Brooks Cole
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Summary
Part I: INTRODUCTION TO BASIC LABORATORY TECHNIQUES. Experiment 1. Solubility. Experiment 2. Crystallization. Experiment 3. Extraction. Experiment 4. Chromatography. Experiment 5. Simple and Fractional Distillation. Experiment 6. Infrared Spectroscopy and Boiling-Point Determination. Essay: Aspirin. Experiment 7. Acetylsalicylic Acid. Essay: Analgesics. Experiment 8. Acetanilide. Experiment 9. Acetaminophen. Essay: Identification of Drugs. Experiment 10. TLC Analysis of Analgesic Drugs. Essay: Caffeine. Experiment 11. Isolation of Caffeine. Experiment 11A. Isolation of Caffeine from Tea Leaves. Experiment 11B. Isolation of Caffeine from a Tea Bag. Essay: Esters -- Flavors and Fragrances. Experiment 12. Isopentyl Acetate (Banana Oil). Experiment 13. Methyl Salicylate (Oil of Wintergreen). Essay: Terpenes and Phenylpropanoids. Experiment 14. Isolation of Eugenol from Cloves. Essay: Stereochemical Theory of Odor. Experiment 15. Spearmint and Caraway Oil: (+)- and (-)- Carvones. Essay: The Chemistry of Vision. Experiment 16. Isolation of Chlorophyll and Carotenoid Pigments from Spinach. Essay: Ethanol and Fermentation Chemistry. Experiment 17. Ethanol from Sucrose. Part II: INTRODUCTION TO MOLECULAR MODELING. Essay: Molecular Modeling and Molecular Mechanics. Experiment 18. An Introduction to Molecular Modeling. Experiment 18A. The Conformations of n-Butane: Local Minima. Experiment 18B. Cyclohexane Chair and Boat Conformations. Experiment 18C. Substituted Cyclohexane Rings. Experiment 18D. cis- and trans-2-Butene. Essay: Computational Chemistry -- Ab initio and Semiempirical Methods. Experiment 19. Computational Chemistry. Experiment 19A. Heats of Formation: Isomerism, Tautomerism, and Regioselectivity. Experiment 19B. Heats of Reactions: SN1 Reaction Rates. Experiment 19C. Density-Electrostatic Potential. Maps -- Acidities of Carboxylic Acids. Experiment 19D. Density -- Electrostatic Potential Maps: Carbocations. Experiment 19E. Density -- LUMO Maps: Reactivities of Carbonyl Groups. Part III: PROPERTIES AND REACTIONS OF ORGANIC COMPOUNDS. Experiment 20. Reactivities of Some Alkyl Halides. Experiment 21. Nucleophilic Substitution Reactions: Competing Nucleophiles. Experiment 21A. Competing Nucleophiles with 1-Butanol or 2-Butanol. Experiment 21B. Competing Nucleophiles with 2-Methyl-2-Propanol. Experiment 21C. Analysis. Experiment 22. Hydrolysis of Some Alkyl Chlorides Experiment 23. Synthesis of n-Butyl Bromide and t-Pentyl Chloride. Experiment 23A. n-Butyl Bromide. Experiment 23B. t-Pentyl Chloride. Experiment 24. 4-Methylcyclohexene Experiment 25. Phase-Transfer Catalysis: Addition of Dichlorocarbene to Cyclohexene Essay: Fats and Oils. Experiment 26. Methyl Stearate from Methyl Oleate. Essay: Soaps and Detergents. Experiment 27. Preparation of Soap. Experiment 28. Preparation of a Detergent. Essay: Petroleum and Fossil Fuels. Experiment 29. Gas Chromatographic Analysis of Gasolines. Essay: Detection of Alcohol: The Breathalyzer. Experiment 30. Chromic Acid Oxidation of Alcohols Experiment 30A. Chromic Acid Oxidation of Alcohols -- Visible Spectrophotometer Method. Experiment 30B. Chromic Acid Oxidation of Alcohols -- UV-VIS Spectrophotometer Method. Essay: Green Chemistry. Experiment 31. Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination. Experiment 31A. Chiral Reduction of Ethyl Acetoacetate. Experiment 31B. NMR Determination of the Optical Purity of (S)-Ethyl 3-Hydroxybutanoate. Experiment 32. Nitration of Aromatic Compounds Using a Recyclable Catalyst. Experiment 33. An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol. Experiment 34. Multi-Step Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid. Experiment 34A. Preparation of Benzoin by Thiamine Catalysis Experiment 34B. Preparation of Benzil. Experiment 34C. Preparation of Benzilic Acid. Experiment 35. Tetraphenylcyclopentadienone. Experiment 36. Triphenylmethanol and Benzoic Acid. Experiment 36A. Triphenylmethanol. Experiment 36
Table of Contents
| Introduction to Basic Laboratory Techniques | |
| Solubility | |
| Crystallization | |
| Extraction | |
| Chromatography | |
| Simple and Fractional Distillation | |
| Infrared Spectroscopy and Boiling-Point Determination | |
| Essay: Aspirin | |
| Acetylsalicylic Acid | |
| Essay: Analgesics | |
| Acetanilide | |
| Acetaminophen | |
| Essay: Identification of Drugs | |
| TLC Analysis of Analgesic Drugs | |
| Essay: Caffeine | |
| Isolation of Caffeine | |
| Experiment | |
| Isolation of Caffeine from Tea Leaves | |
| Experiment | |
| Isolation of Caffeine from a Tea Bag | |
| Essay: Esters -- Flavors and Fragrances | |
| Isopentyl Acetate (Banana Oil) | |
| Methyl Salicylate (Oil of Wintergreen) | |
| Essay: Terpenes and Phenylpropanoids | |
| Isolation of Eugenol from Cloves | |
| Essay: Stereochemical Theory of Odor | |
| Spearmint and Caraway Oil: (+)- and (-)- Carvones | |
| Essay: The Chemistry of Vision | |
| Isolation of Chlorophyll and Carotenoid Pigments from Spinach | |
| Essay: Ethanol and Fermentation Chemistry | |
| Ethanol from Sucrose | |
| Introduction to Molecular Modeling | |
| Essay: Molecular Modeling and Molecular Mechanics | |
| An Introduction to Molecular Modeling | |
| The Conformations of n-Butane: Local Minima | |
| Cyclohexane Chair and Boat Conformations | |
| Substituted Cyclohexane Rings | |
| cis- and trans-2-Butene | |
| Essay: Computational Chemistry -- Ab initio and Semiempirical Methods | |
| Computational Chemistry | |
| Heats of Formation: Isomerism, Tautomerism, and Regioselectivity | |
| Heats of Reactions: SN1 Reaction Rates | |
| Density-Electrostatic Potential | |
| Maps -- Acidities of Carboxylic Acids | |
| Density -- Electrostatic Potential Maps: Carbocations | |
| Density -- LUMO Maps: Reactivities of Carbonyl Groups | |
| Properties and Reactions of Organic Compounds | |
| Reactivities of Some Alkyl Halides | |
| Nucleophilic Substitution Reactions: Competing Nucleophiles | |
| Competing Nucleophiles with 1-Butanol or 2-Butanol | |
| Competing Nucleophiles with 2-Methyl-2-Propanol | |
| Analysis | |
| Hydrolysis of Some Alkyl Chlorides | |
| Synthesis of n-Butyl Bromide and t-Pentyl Chloride | |
| n-Butyl Bromide | |
| t-Pentyl Chloride | |
| 4-Methylcyclohexene | |
| Phase-Transfer Catalysis: Addition of Dichlorocarbene to Cyclohexene Essay: Fats and Oils | |
| Methyl Stearate from Methyl Oleate | |
| Essay: Soaps and Detergents | |
| Preparation of Soap | |
| Preparation of a Detergent | |
| Essay: Petroleum and Fossil Fuels | |
| Gas Chromatographic Analysis of Gasolines | |
| Essay: Detection of Alcohol: The Breathalyzer | |
| Chromic Acid Oxidation of Alcohols | |
| Chromic Acid Oxidation of Alcohols -- Visible Spectrophotometer Method | |
| Chromic Acid Oxidation of Alcohols -- UV-VIS Spectrophotometer Method | |
| Essay: Green Chemistry | |
| Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination | |
| Chiral Reduction of Ethyl Acetoacetate | |
| NMR Determination of the Optical Purity of (S)-Ethyl 3-Hydroxybutanoate | |
| Nitration of Aromatic Compounds Using a Recyclable Catalyst | |
| An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol | |
| Multi-Step Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid | |
| Preparation of Benzoin by Thiamine Catalysis | |
| Preparation of Benzil | |
| Preparation of Benzilic Acid | |
| Tetraphenylcyclopentadienone | |
| Triphenylmethanol and Benzoic Acid | |
| Triphenylmethanol | |
| Benzoic Acid | |
| Resolution of (+/-)-alpha-Phenylethylamine and Determination of Optical Purity | |
| Resolution of (+/-)-alpha-Phenylethylamine | |
| Determination of Optical Purity Using NMR and a Chiral Resolving Agent | |
| The Aldol Condensation Reaction: Preparation of Benzalacetophenones Chalcones) | |
| Preparation of an alpha,beta-Unsaturated Ketone via Michael and Aldol Condensation Reactions | |
| Enamine Reactions: 2-Acetylcyclohexanone | |
| 1,4-Diphenyl-1,3-Butadiene | |
| Relative Reactivities of Several Aromatic Compounds | |
| Nitration of Methyl Benzoate | |
| Essay: Local Anesthetics | |
| Benzocaine | |
| Essay: Pheromones: Insect Attractants and Repellents | |
| N,N-Diethyl-m-Toluamide: The Insect Repellent "OFF" | |
| Essay: Sulfa Drugs | |
| Sulfa Drugs: Preparation of Sulfanilamide | |
| Essay: Food Colors | |
| Chromatography of Some Dye Mixtures | |
| Essay: Polymers and Plastics | |
| Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene | |
| Polyesters | |
| Polyamide (Nylon) | |
| Polystyrene | |
| Infrared Spectra of Polymer Samples | |
| Essay: Diels-Alder Reactions and Insecticides | |
| The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride | |
| Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone | |
| Photoreduction of Benzophenone | |
| Synthesis of beta-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol | |
| Essay: Fireflies and Photochemistry | |
| Luminol | |
| Essay: The Chemistry of Sweeteners | |
| Carbohydrates | |
| Analysis of a Diet Soft Drink by HPLC | |
| Essay: Chemistry of Milk | |
| Isolation of Casein and Lactose from Milk | |
| Isolation of Casein from Milk | |
| Isolation of Lactose from Milk | |
| Identification of Organic Substances | |
| Identification of Unknowns | |
| Solubility Tests | |
| Tests for the Elements (N, S, X) | |
| Tests for Unsaturation | |
| Aldehydes and Ketones | |
| Carboxylic Acids | |
| Phenols | |
| Amines | |
| Alcohols | |
| Esters | |
| Project-Based Experiments | |
| Preparation of a C-4 or C-5 Acetate Ester | |
| A Separation and Purification Scheme | |
| Extractions with a separatory funnel | |
| Extractions with a Screw-Cap centrifuge tube | |
| Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, or Fennel | |
| Isolation of Essential Oils by Steam Distillation | |
| Identification of the Constituents of Essential Oils by Gas Chromatography-Mass Spectrometry | |
| Investigation of the Essential Oils of Herbs and Spices-Mini-Research Project | |
| Friedel-Crafts Acylation | |
| The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry | |
| Carbonation of an Unknown Aromatic Halide | |
| The Aldehyde Enigma | |
| Synthesis of Substituted Chalcones: A Guided-Inquiry Experience | |
| Michael and Aldol Condensation Reactions | |
| Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem | |
| An Oxidation Puzzle | |
| The Techniques | |
| Laboratory Safety | |
| The Laboratory Notebook, Calculations, and Laboratory Records | |
| Laboratory Glassware: Care and Cleaning | |
| How to Find Data for Compounds: Handbooks and Catalogues | |
| Measurement of Volume and Weight | |
| Heating and Cooling Methods | |
| Reaction Methods | |
| Filtration | |
| Physical Constants of Solids: The Melting Point | |
| Solubility | |
| Crystallization: Purification of Solids | |
| Extractions, Separations, and Drying Agents | |
| Physical Constants of Liquids: The Boiling Point and Density | |
| Simple Distillation | |
| Fractional Distillation, Azeotropes | |
| Vacuum Distillation, Manometers | |
| Sublimation | |
| Steam Distillation | |
| Column Chromatography | |
| Thin-Layer Chromatography | |
| High-Performance Liquid Chromatography (HPLC) | |
| Gas Chromatography | |
| Polarimetry | |
| Refractometry | |
| Infrared Spectroscopy | |
| Nuclear Magnetic Resonance Spectroscopy (Proton NMR) | |
| Carbon-13 Nuclear Magnetic Resonance Spectroscopy | |
| Mass Spectrometry | |
| Guide to the Chemical Literature | |
| Tables of Unknowns and Derivatives | |
| Procedure for Preparing Derivatives | |
| Index of Spectra. | |
| Table of Contents provided by Publisher. All Rights Reserved. |
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