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Introduction to Organic Laboratory Techniques : A Small Scale Approach

Introduction to Organic Laboratory Techniques : A Small Scale Approach - 2nd edition

Introduction to Organic Laboratory Techniques : A Small Scale Approach - 2nd edition

ISBN13: 9780534408336

ISBN10: 0534408338

Introduction to Organic Laboratory Techniques : A Small Scale Approach by Donald L. Pavia, Lampman, Kriz and Engel - ISBN 9780534408336
Edition: 2ND 05
Copyright: 2005
Publisher: Brooks/Cole Publishing Co.
Published: 2005
International: No
Introduction to Organic Laboratory Techniques : A Small Scale Approach by Donald L. Pavia, Lampman, Kriz and Engel - ISBN 9780534408336

ISBN13: 9780534408336

ISBN10: 0534408338

Edition: 2ND 05


In this laboratory textbook for students of organic chemistry, experiments are designed to utilize standard-scale ("macroscale") glassware and equipment but with smaller amounts of chemicals and reagents. The textbook features a large number of traditional organic reactions and syntheses, as well as the isolation of natural products and experiments with a biological or health science focus. The organization of the text is based on essays and topics of current interest. There are six introductory technique-based experiments and eleven project-based experiments. In addition, there is a section of green chemistry experiments. The book contains a comprehensive treatment of laboratory techniques, including small-scale and some microscale methods.


  • NEW! New, techniques-based experiments are used as the first, introductory experiments to appeal to those situations where instructors do not want to jump immediately into advanced material. New technique experiments include: Experiment 1, "Solubility;" Experiment 2, "Crystallization;" Experiment 3, "Extraction;" Experiment 4, "Chromatography;" Experiment 5, "Simple and Fractional Distillation;" and, Experiment 6, "Infrared Spectroscopy and Boiling Point Determination." Several of these experiments conclude with "Critical Thinking Applications"--short exercises in which students must provide experimentally determined solutions to problems related to the techniques and the underlying principles.
  • Experiments are well-written, comprehensive, and pre-tested.
  • Infrared, proton NMR, and 13C NMR spectroscopy is incorporated into many experiments. Some experiments also have an option to use gas chromatography-mass spectrometry.
  • For discovery-based learning needs, open-ended experiments are provided to allow students to "write" their own experimental procedures and make their own discoveries.
  • Molecular modeling experiments give students an opportunity to experience the power of molecular modeling software.
  • "Caution" boxes emphasize careful handling of chemicals and the importance of safety in the laboratory.
  • Clear and accurate diagrams of laboratory set-ups increase students' confidence in setting up a lab.
  • End-of-chapter problems test students' mastery of the material.
  • NEW! The Second Edition features a new essay, "Green Chemistry," and two new green chemistry experiments: Experiment 31, "Chiral Reduction of Ethyl Acetoacetate: Optical Purity Determination;" and, Experiment 32, "Nitration of Aromatic Compounds Using a Recyclable Catalyst."
  • NEW! The authors have included a new section of project-based experiments that features: Experiment 57, "A Separation and Purification Scheme;" Experiment 60, "The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry;" Experiment 62, "The Aldehyde Enigma;" Experiment 63, "Synthesis of Substituted Chalcones: A Guided-Inquiry Experience;" and, Experiment 66, "An Oxidation Puzzle." In all of these experiments, students must either solve a significant problem or they must generate all or part of a procedure. Intended to promote critical thinking, these experiments not only challenge students, but also give them a feeling of what it is like to "do" research in chemistry.
  • NEW! New exercises involving molecular modeling and computational chemistry have been added to several experiments.
  • NEW! The Second Edition features a reorganization of the technique chapters to more closely match the order in MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY.
  • NEW! This new edition also includes three new technique chapters: Technique 4," How to Find Data for Compounds: Handbooks and Catalogues;" Technique 10, " Solubility;" and, Technique 28, "Mass Spectrometry." In addition, several technique chapters have been extensively revised and update.
  • The textbook contains a variety of small-scale experiments using standard-scale (macroscale) glassware and equipment.
  • Essays and examples on contemporary topics are provided to spark student interest and engage them in the learning process.
  • Green chemistry has been introduced as it's become an important topic to share with students.

Table of Contents

Table of Contents


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.


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.


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 36B. Benzoic Acid.
Experiment 37. Resolution of (+/-)-alpha-Phenylethylamine and Determination of Optical Purity.
Experiment 37A. Resolution of (+/-)-alpha-Phenylethylamine.
Experiment 37B. Determination of Optical Purity Using NMR and a Chiral Resolving Agent.
Experiment 38. The Aldol Condensation Reaction: Preparation of Benzalacetophenones Chalcones).
Experiment 39. Preparation of an alpha,beta-Unsaturated Ketone via Michael and Aldol Condensation Reactions.
Experiment 40. Enamine Reactions: 2-Acetylcyclohexanone.
Experiment 41. 1,4-Diphenyl-1,3-Butadiene.
Experiment 42. Relative Reactivities of Several Aromatic Compounds.
Experiment 43. Nitration of Methyl Benzoate.

Essay: Local Anesthetics.

Experiment 44. Benzocaine.

Essay: Pheromones: Insect Attractants and Repellents.

Experiment 45. N,N-Diethyl-m-Toluamide: The Insect Repellent "OFF".

Essay: Sulfa Drugs.

Experiment 46. Sulfa Drugs: Preparation of Sulfanilamide.

Essay: Food Colors.

Experiment 47. Chromatography of Some Dye Mixtures.

Essay: Polymers and Plastics.

Experiment 48. Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene.
Experiment 48A. Polyesters.
Experiment 48B. Polyamide (Nylon).
Experiment 48C. Polystyrene.
Experiment 48D. Infrared Spectra of Polymer Samples.

Essay: Diels-Alder Reactions and Insecticides.

Experiment 49. The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride.
Experiment 50. Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone.
Experiment 50A. Photoreduction of Benzophenone.
Experiment 50B. Synthesis of beta-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol.

Essay: Fireflies and Photochemistry.

Experiment 51. Luminol.

Essay: The Chemistry of Sweeteners.

Experiment 52. Carbohydrates.
Experiment 53. Analysis of a Diet Soft Drink by HPLC.

Essay: Chemistry of Milk.

Experiment 54. Isolation of Casein and Lactose from Milk.
Experiment 54A. Isolation of Casein from Milk.
Experiment 54B. Isolation of Lactose from Milk.


Experiment 55. Identification of Unknowns.
Experiment 55A. Solubility Tests.
Experiment 55B. Tests for 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.


Experiment 56. Preparation of a C-4 or C-5 Acetate Ester.
Experiment 57. A Separation and Purification Scheme.
Experiment 57A. Extractions with a separatory funnel.
Experiment 57B. Extractions with a Screw-Cap centrifuge tube.
Experiment 58. Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, or Fennel.
Experiment 58A. Isolation of Essential Oils by Steam Distillation.
Experiment 58B. Identification of the Constituents of Essential Oils by Gas Chromatography-Mass
Experiment 58C. Investigation of the Essential Oils of Herbs and Spices-Mini-Research Project.
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. 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.


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 (Proton NMR).
Technique 27. Carbon-13 Nuclear Magnetic Resonance Spectroscopy.
Technique 28. Mass Spectrometry.
Technique 29. Guide to the Chemical Literature.

Appendix 1: Tables of Unknowns and Derivatives.
Appendix 2: Procedure for Preparing Derivatives.
Appendix 3: Index of Spectra.

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