Microscale Operational Organic Chemistry: A Problem-Solving Approach to the Laboratory Course

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9780130335180: Microscale Operational Organic Chemistry: A Problem-Solving Approach to the Laboratory Course

This practical guide to the core operations in the organic lab gives an excellent selection of clever microscale experiments, enabling users to have an excellent resource that encourages scientific problem-solving. The unique problem-solving approach given in this guide encourages readers to master major lab operations, explaining why they are carried out the way they are. Readers will understand each scientific problem, formulate a meaningful hypothesis, and then solve the problem. Sections on qualitative organic analysis and basic operations such as glassware use, conducting chemical reactions, washing and drying operations, purification operations, measuring, and instrumental analyses round out this handy reference work. The extensive appendices, bibliography, and basic operations sections make this an excellent desktop resource for organic chemists and other lab technicians.

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To the Instructor

This book is a microscale laboratory textbook based on the third edition of Operational Organic Chemistry: A Problem-Solving Approach to the Laboratory Course. Every experiment and minilab in the book can be performed by students using the microscale glassware available in a Mayo/Pike-style microscale lab kit with 14/10 standard-taper joints and threaded connectors. Most of the experiments could also be performed successfully with alternative microscale glassware, such as that provided in a Williamson lab kit, but some might need to be scaled down further and the instructor would have to provide additional instructions regarding the use of the glassware.

Some organic chemists regard a "microscale" experiment as one involving approximately 0.1 g of the limiting reactant. Dealing with such small quantities can be discouraging to students with standard scale fingers, who end up with a drop or a few grains of product, if any. Therefore, I have adopted a working definition of a microscale experiment as one that can be performed using the glassware available in a typical microscale lab kit, along with appropriate locker supplies as recommended in the Instructor's Manual.

In writing this book, I have been guided by my convictions that students (1) perform better in the organic laboratory course if they master the major lab operations early and apply them throughout the course, (2) learn organic chemistry better if they keep their minds engaged by approaching each experiment as a problem-solving exercise, and (3) perform any task better if they are sufficiently motivated.

Part I is devoted to experiments designed to teach the basic laboratory operations, where an operation, as used here, is a process that utilizes one or more basic lab techniques, such as heating, cooling, and vacuum filtration, to accomplish some end, such as the purification of a solid. Once students have mastered the major operations by completing the appropriate experiments in Part I, they should be ready to apply those operations in Part II, which contains a large selection of experiments that are correlated with topics found in most organic chemistry lecture textbooks. This operational approach helps students understand that an organic synthesis, for example, is not a unique phenomenon that can be experienced only by mechanically following a detailed "recipe." Rather, it is the outcome of a logical sequence of interrelated operations adapted to the requirements of the synthesis.

In addition to teaching lab skills, the experiments in this book are designed to help students develop the observational and critical thinking skills that are essential prerequisites for a successful career in science and in virtually every other professional field. Each major experiment requires the student to solve a specific scientific problem through the application of sound scientific methodology. Before an experiment, the student must first define the problem based on information provided in a hypothetical Scenario. After a preliminary reading of the experiment, the student should be able to develop a working hypothesis regarding its outcome. During the experiment, the student gathers and evaluates evidence bearing on the problem and, as necessary, reevaluates and revises the hypothesis based on experimental observations and data. Finally, the student tests the hypothesis by obtaining a melting point, a spectrum, a gas chromatogram, or by some other means, and arrives at a conclusion. Because of the level at which most undergraduate organic chemistry courses are taught, the problems must, of necessity, be kept relatively simple and (with a few exceptions) should not be compared to "real" research problems tackled by professional chemists. It is not the intent of this book to make every student a research chemist; most students who take an organic chemistry course have no intention of going into the field. But the critical thinking and methodological skills required to solve the problems are comparable to those applied by research scientists, and applying those skills should give the student a better understanding of the nature and practice of science.

As a motivational device and to provide a frame of reference for the problems, students are asked to regard themselves as "consulting chemists" working for an institute operated by their college or university. Various individuals and organizations come to the institute with their scientific problems and the problems are relayed to the "project group" comprising each lab section, to be solved individually or (sometimes) through collaboration. Although some of the Scenarios are a bit contrived, most of them describe tasks similar to those a practicing chemist might be called upon to perform.

To implement this problem-solving approach in the organic chemistry lab, each experiment includes a section, "Applying Scientific Methodology," intended to help the student understand the problem, formulate a meaningful hypothesis, and solve the problem. The Introduction and Experiment 1 describe in some detail how the student can apply scientific methodology to the solution of a problem, so students should read at least the section "Problem Solving in the Organic Chemistry Lab" in the Introduction and should be asked to read the Scenario and "Applying Scientific Methodology" sections of Experiment 1 even if you choose not to assign it. Because each experiment is designed as a problem for the student to solve, the outcome is not explicitly stated in the experiment itself. In a few experiments, such as Experiments 31 and 43, the identity of an organic reactant is unknown as well. Therefore, it is imperative that the instructor or laboratory coordinator obtain a copy of the Instructor's Manual, which is provided free of charge by Prentice Hall to adopters of this book.

Part III contains a number of minilabs to provide additional flexibility. These short experiments can be used to fill in those gaps in a lab course when, for example, the students finish a two-period experiment during the first hour or so of the second period. They can also be used to teach techniques (such as paper chromatography in Minilab 9) that are seldom used in the major experiments or to introduce additional theoretical topics, such as photochemistry (Minilab 24). Part IV is a self-contained introduction to qualitative organic analysis, which is also incorporated into some of the Part II experiments, particularly Experiments 38 and 49. Part V contains detailed descriptions of the laboratory operations, which are flagged in the experiments by operation numbers in brackets, such as OP-30.

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Book Description Prentice Hall, 2003. Book Condition: New. Brand New, Unread Copy in Perfect Condition. A+ Customer Service! Summary: Preface. Introduction. I. MASTERING THE OPERATIONS. 1. Learning Basic Operations. The Effect of pH on a Food Preservative. 2. Extraction and Evaporation. Separating the Components of Panacetin. 3. Recrystallization and Melting-Point Measurement. Identifying a Constituent of Panacetin. 4. Heating under Reflux. Synthesis of Salicylic Acid from Wintergreen Oil. 5. Simple Distillation, Gas Chromatography. Preparation of Synthetic Banana Oil. 6. Fractional Distillation. Separation of Petroleum Hydrocarbons. 7. Addition, Mixing, Sublimation. Preparation of Camphor. 8. Boiling Point, Refractive Index. Identification of a Petroleum Hydrocarbon. 9. Column Chromatography, UV-VIS Spectrometry. Isolation and Isomerization of Lycopene from Tomato Paste. 10. Steam Distillation, Infrared Spectrometry. Isolation and Identification of the Major Constituent of Clove Oil. 11. Thin-Layer Chromatography, NMR Spectrometry. Identification of Unknown Ketones. 12. Vacuum Distillation, Optical Rotation. Optical Activity of a-Pinene. II. CORRELATED LABORATORY EXPERIMENTS. 13. Investigation of a Chemical Bond by Infrared Spectrometry. 14. Properties of Common Functional Groups. 15. Thin-Layer Chromatographic Analysis of Drug Components. 16. Separation of an Alkane Clathrate. 17. Isomers and Isomerization Reactions. 18. Structures and Properties of Stereoisomers. 19. Bridgehead Reactivity in an SN1 Solvolysis Reaction. 20. Reaction of Iodoethane with Saccharin, an Ambident Nucleophile. 21. Dehydration of Methylcyclohexanols. 22. Synthesis of 7,7-Dichloronorcarane Using a Phase-Transfer Catalyst. 23. Stereochemistry of the Addition of Bromine to trans-Cinnamic Acid. 24. Hydration of a Difunctional Alkyne. 25. Preparation of Bromotriphenylmethane and the Trityl Free Radical. 26. Chain-Growth Polymerization of Styrene and Methyl Methacrylate. 27. Synthesis of Ethanol by Fermentation. 28. Reaction of Butanols with Hydrobromic Acid. 29. Borohydride Reduction of Vanillin to Vanillyl Alcohol. 30. Synthesis of Triphenylmethanol and the Trityl Carbocation. 31. Identification of a Conjugated Diene from Eucalyptus Oil. 32. Spectral Identification of Monoterpenoids. 33. Synthesis and Spectral Analysis of Aspirin. 34. Preparation of Nonbenzenoid Aromatic Compounds. 35. Mechanism of the Nitration of Arenes by Nitronium Fluoborate. 36. Friedel-Crafts Acylation of Anisole. 37. Structure of a Natural Product in Anise Oil. 38. Identification of an Oxygen-Containing Organic Compound. 39. Wittig Synthesis of 1,4-Diphenyl-1,3-Butadiene. 40. Effect of Reaction Conditions on the Condensation of Furfural with Cyclopentanone. 41. Haloform Oxidation of 4'-Methoxyacetophenone. 42. Electronic Effect of a para-Iodo Substituent. 43. Synthesis and Identification of an Unknown Carboxylic Acid. 44. Preparation of the Insect Repellent N,N-Diethyl-meta-toluamide. 45. Synthesis of 2-Acetylcyclohexanone by the Stork Reaction. 46. Synthesis of Dimedone and Measurement of its Tautomeric Equilibrium Constant. 47. Preparation of Para Red and Related Azo Dyes. 48. Reaction of Phthalimide with Sodium Hypochlorite. 49. Identification of an Unknown Amine. 50. Preparation and Mass Spectrum of 2-Phenylindole. 51. Nucleophilic Strength and Reactivity in SNAr Reactions. 52. Structure of an Unknown d-Hexose. 53. Fatty Acid Content o. Bookseller Inventory # ABE_book_new_0130335185

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