A Small Scale Approach to Organic Laboratory Techniques,
4th Edition

Introduction.
WELCOME TO ORGANIC CHEMISTRY.
Laboratory Safety. Organization of the Textbook. Advance Preparation. Budgeting Time. Purpose.
PART I: 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 4B. Extractions with a Screw-Cap Centrifuge Tube
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
Essay. Aspirin.
Experiment 8. Acetylsalicylic Acid.
Essay. Analgesics.
Experiment 9. Acetaminophen.
Essay. Identification of Drugs.
Experiment 10.TLC Analysis of Analgesic Drugs.
Essay. Caffeine.
Experiment 11. Isolation of Caffeine.
Experiment 11A. Extraction of Caffeine from Tea.
Experiment 11B. Isolation of Caffeine from a Tea Bag.
Essay. Esters--Flavors and Fragrances.
Experiment 12: Isopentyl Acetate (Banana Oil).
Essay, Terpenes and Phenylpropanoids.
Experiment 13. Isolation of Eugenol from Cloves.
Essay. Stereochemical Theory of Odor.
Experiment 14. Spearmint and Caraway Oil: (+)- and (-)- Carvones.
Essay.The Chemistry of Vision.
Experiment 15. Isolation of Chlorophyll and Carotenoid Pigments from Spinach.
Essay: Ethanol and Fermentation Chemistry.
Experiment 16. Ethanol from Sucrose.
PART II: INTRODUCTION TO MOLECULAR MODELING.
Essay: Molecular Modeling and Molecular Mechanics.
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.
Essay: Computational Chemistry - Ab initio and Semiempirical Methods.
Experiment 18. Computational Chemistry.
Experiment 18A. Heats of Formation: Isomerism, Tautomerism, and Regioselectivity.
Experiment 18B. Heats of Reactions: 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 III: PREPARATIONS AND REACTIONS OF ORGANIC COMPOUNDS.
Experiment 19. Reactivities of Some Alkyl Halides.
Experiment 20. Nucleophilic Substitution Reactions: Competing Nucleophiles
Experiment 20A. Competing Nucleophiles with 1-Butanol or 2-Butanol.
Experiment 20B. Competing 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-Methylcyclohexen
Essay. Fats and Oils.
Experiment 23. Methyl Stearate from Methyl Oleate.
Essay: Soap
Experiment 24. Preparation of Soap.
Essay: Petroleum and Fossil Fuels.
Experiment 25. Gas Chromatographic Analysis of Gasolines.
Essay: Biofuels.
Experiment 26. Biodiesel.
Experiment 26A. Biodiesel from Coconut Oil.
Experiment 26B. Biodiesel from Other Oils.
Experiment 26C. Analysis of Biodiesel.
Essay: Green Chemistry.
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 (+/-)-alpha-Phenylethylamine and Determination of Optical Purity.
Experiment 30A. Resolution of (+/-)-alpha-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 ,-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.
Essay: Synthetic Dyes.
Experiment 44. Preparation of Methyl Orange.
Experiment 45. Preparation of Indigo.
Experiment 46. Formulation of a Paint and Art Project.
Essay. Local Anesthetics.
Experiment 47. Benzocaine.
Essay. Pheromones: Insect Attractants and Repellants.
Experiment 48. N,N-Diethyl-m-toluamide: The Insect Repellent "OFF."
Essay: Sulfa Drugs.
Experiment 49. Sulfa Drugs: Preparation of Sulfanilamide.
Essay: Polymers and Plastics.
Experiment 50. Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene.
Experiment 50A. Polyesters.
Experiment 50B. Polyamide (Nylon).
Experiment 50C. Polystyrene.
Experiment 50D. Infrared Spectra of Polymer Samples.
Experiment 51. Ring-Opening Metathesis Polymerization (ROMP) Using a Grubbs Catalyst: A Three Step Synthesis of a Polymer.
Experiment 51A. Diels-Adler Reaction.
Experiment 51B. Conversion of the Diels-Adler Adduct to the Diester.
Experiment 51C. Synthesizing the Polymer by Ring-Opening Metathesis Polymerization ROMP)
Essay. Diels–Alder Reaction and Insecticides.
Experiment 52. The Diels–Alder Reaction of Cyclopentadiene with Maleic Anhydride.
Experiment 53. Diels-Adler Reaction with Anthracine-9-Methanol.
Experiment 54. Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone.
Experiment 54A. Photoreduction of Benzophenone.
Experiment 54B. Synthesis of -Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol.
Essay. Fireflies and Photochemistry.
Experiment 55. Luminol.
Essay. The Chemistry of Sweeteners.
Experiment 56. Carbohydrates.
Experiment 57. Analysis of a Diet Soft Drink by HPLC.
Part IV: IDENTIFICATION OF ORGANIC SUBSTANCES.
Experiment 58. Identification of Unknowns.
Experiment 58A. Solubility Tests.
Experiment 58B. Tests for the Elements (N, S, X).
Experiment 58C. Tests for Unsaturation.
Experiment 58D. Aldehydes and Ketones.
Experiment 58E. Carboxylic Acids.
Experiment 58F. Phenols.
Experiment 58G. Amines.
Experiment 58H. Alcohols.
Experiment 58I. Esters.
PART V: PROJECT-BASED EXPERIMENTS.
Experiment 59. Preparation of a C-4 or C-5 Acetate Ester.
Experiment 60. Competing Nucleophiles in SN1 and SN2 Reactions: Investigations Using 2-Pentanol and 3-Pentanol.
Experiment 61. Friedel-Crafts Acylation.
Experiment 62. The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry.
Experiment 63. Carbonation of an Unknown Aromatic Halide.
Experiment 64. The Aldehyde Enigma.
Experiment 65. Synthesis of Substituted Chalcones: A Guided-Inquiry Experience.
Experiment 66. Green Epoxidation of Chalcones.
Experiment 67. Cyclopropanation Reactions of Chalcones.
Experiment 68. Michael and Aldol Condensation Reactions.
Experiment 69. Esterification Reactions of Vanillin: The Use of NMR to Determine a Structure.
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 (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.

• Donald L. Pavia

  Donald L. Pavia earned his BS degree in chemistry from Reed College and his PhD in organic chemistry from Yale University. In 1970, he joined the faculty at Western Washington University as Assistant Professor and now holds the rank of Professor Emeritus. He is the coauthor of two organic laboratory books that include techniques and experiments: INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE APPROACH TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning), as well as MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), which highlights techniques to be used with a faculty member's own experiments. He is a co-author, with Gary M. Lampman, George S. Kriz and James R. Vyvyan of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY (Cengage Learning). Professor Pavia's research interests center on the synthesis and reactions of valence tautomeric and photochromic compounds, especially pyrylium-3-oxide tautomers. Autoxidations are a special interest. His other interests include the use of computers in teaching organic chemistry, both for lecture presentation and for the simulation of laboratories. He is the author of several computer programs. One such program is SQUALOR (Simulated Qualitative Organic Analysis) for which he won the 1986 EDUCOM/NCRIPTAL award. The program is designed for teaching the methods for solving organic unknowns.

• George S. Kriz

  George S. Kriz is Professor of Chemistry at Western Washington University. He earned his B.S. degree in chemistry from the University of California, and his Ph.D. from Indiana University, Bloomington, IN. In 1967 he joined the faculty at Western Washington University and recently served as department chair. He served as the General Chair of the 17th Biennial Conference on Chemical Education for 2001-2002. Professor Kriz was honored with the Peter J. Elich Excellence in Teaching Award (College of Arts and Sciences), Western Washington University, in 2000 and the Distinguised Service Award from the Division of Chemical Education, American Chemical Society (2010). He is the co-author with Donald Pavia, Gary Lampman, and Randall Engel of two organic laboratory books that include both techniques and experiments: INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE APPROACH TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning). Their book, MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), includes techniques only, and can be used with a faculty member's own experiments. He is a co-author, with Donald Pavia, Gary Lampman, and James Vyvyan, of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY (Cengage Learning). Professor Kriz's research interests include: developing new experiments for the organic chemistry laboratory; chemical education and the teaching of chemistry courses for general-understanding audiences; and determination of the structures of natural products using spectroscopic methods.

• Gary M. Lampman

  Gary M. Lampman earned his BS degree in chemistry from the University of California, Los Angeles, and his PhD in organic chemistry from the University of Washington. In 1964, he joined the faculty at Western Washington University as Assistant Professor, rising to Professor in 1973. He received the Outstanding Teaching Award for the College of Arts and Sciences in 1976. He now holds the title of Professor Emeritus. Teaching has always been an important part of his life. Contact with students invigorates him. He is the coauthor of two organic laboratory books that include techniques and experiments: INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE ARPPROACH TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning), as well as MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), which highlights techniques to be used with a faculty member's own experiments. He is a co-author, with Donald L. Pavia, George S. Kriz, and James R. Vyvyan of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY, Fourth Edition (Cengage Learning). Professor Lampman also is the author of the computer program for teaching organic nomenclature: ORGANIC NOMENCLATURE: AN INTRODUCTION TO THE IUPAC SYSTEM. His research interests center on synthetic methods involving the reaction of free radicals on unsaturated cobaloximes (vitamin B12 model compounds), synthesis of strained small ring compounds, and chemical education. He is the author of 18 papers in these areas. He is a member of the American Chemical Society (Organic and Chemical Education divisions), and the Washington College Chemistry Teachers Association.

• Randall G. Engel

  Randall G. Engel has taught chemistry for almost 35 years. He has co-authored with Donald Pavia, Gary Lampman, and George Kriz INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning). Their book, MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), includes techniques only, and can be used with a faculty member's own experiments. Engel received his B.A. degree in chemistry from Cornell College and his M.S. degree in chemistry from Western Washington University. He began his teaching career at Wenatchee Valley College in 1975 and continued at Green River Community College and Edmonds Community College. Presently he teaches organic chemistry on a part-time basis at North Seattle Community College.

• This edition includes a new OWLv2 LabSkills program that can be bundled with the textbook. LabSkills provides students the opportunity to practice skills and prepare for real laboratory classes in a safe environment. Students work through the assignments in advance of the lab so they can actively rehearse common practical techniques by engaging with simulations, videos and quizzes. Because LabSkills focuses on techniques, instructors can customize assignments to align with the experiments that students will perform in any given lab session. The online course will also offer assessment specific to this edition's experiments, and include a MindTap Reader.

• New experiments in this edition: Experiment 24 - Preparation of Soap; Experiment 31 - A new green oxidation reaction using Oxone ® in An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol; Experiment 44 - Preparation of Methyl Orange; Experiment 45 - Preparation of Indigo; Experiment 46 - Formulation of a Paint and Art Project.

• New essays in this edition: Soap; Dyes.

• This edition includes a new OWLv2 LabSkills program that can be bundled with the textbook. LabSkills provides students the opportunity to practice skills and prepare for real laboratory classes in a safe environment. Students work through the assignments in advance of the lab so they can actively rehearse common practical techniques by engaging with simulations, videos and quizzes. Because LabSkills focuses on techniques, instructors can customize assignments to align with the experiments that students will perform in any given lab session. The online course will also offer assessment specific to this edition's experiments, and include a MindTap Reader.

• New experiments in this edition: Experiment 24 - Preparation of Soap; Experiment 31 - A new green oxidation reaction using Oxone ® in An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol; Experiment 44 - Preparation of Methyl Orange; Experiment 45 - Preparation of Indigo; Experiment 46 - Formulation of a Paint and Art Project.

• New essays in this edition: Soap; Dyes.

• OWLv2 is the most trusted online learning solution for chemistry. Featuring chemist-developed content, OWLv2 is the only system designed to elevate thinking through Mastery Learning, allowing students to work at their own pace until they understand each concept and skill. Each time a student tries a problem, OWLv2 changes the chemistry, values, and sometimes even the wording of the question to ensure students are learning the concepts and not cheating the system. With detailed, instant feedback and interactive learning resources, students get the help they need when they need it. Now with improved student and instructor tools and greater functionality, OWLv2 is more robust than ever. Discover the power of OWLv2 and take learning to a higher level.

• The textbook contains a variety of well-written, comprehensive, and pre-tested small-scale experiments using standard-scale (macroscale) glassware and equipment.

• Essays and examples on contemporary topics, such as biofuels and nanotechnology are provided to spark student interest and engage them in the learning process.

• Green chemistry is now better integrated due to its importance as a topic for students.

• Infrared, proton NMR, and 13C NMR spectroscopy is incorporated into many experiments. Some experiments also have an option to use gas chromatography-mass spectrometry.

• The authors include introductory, techniques-based experiments first to meet the needs of instructors who do not want to jump immediately into advanced material.

• OWLv2 is the most trusted online learning solution for chemistry, proven to help you get a better grade. Featuring chemist-developed content, OWLv2 is the only system designed to elevate thinking through Mastery Learning, allowing you to work at your own pace until you understand each concept and skill. Each time you try a problem, OWLv2 changes the chemistry, values, and sometimes even the wording of the question to ensure you are learning the concepts and not just doing homework. With detailed, instant feedback and interactive learning resources, you get the help you need when you need it. Now with improved answer entry and input tools, OWLv2 is more robust than ever. Discover the power of OWLv2 and take your learning to a higher level.

• The textbook contains a variety of well-written, comprehensive, and pre-tested small-scale experiments using standard-scale (macroscale) glassware and equipment.

• Essays and examples on contemporary topics help you see the relevance of organic chemistry techniques to your course work and future career.

• Open-ended experiments allow you to "write" your own experimental procedures and make your own discoveries.

• Clear and accurate diagrams of laboratory set-ups increase your confidence in setting up a lab.

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Website for Pavia/Kriz/Lampman/Engel's Small Scale Approach to Organic Laboratory Techniques
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