Solution Manual for A Microscale Approach to Organic Laboratory Techniques, 5th Edition

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Description:

From biofuels, green chemistry, and nanotechnology, this proven laboratory textbook provides the up-to-date coverage students need in their coursework and future careers. The book's experiments, all designed to utilize microscale glassware and equipment, cover traditional organic reactions and syntheses, the isolation of natural products, and molecular modeling and include project-based experiments and experiments that have a biological or health science focus. Updated throughout with new and revised experiments, new and revised essays, and revised and expanded techniques, the Fifth Edition is organized based on essays and topics of current interest.

About the Author

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 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 generalunderstanding audiences; and determination of the structures of natural products using spectroscopic methods.

• ISBN-10 : 1133106528

• ISBN-13 : 978-1133106524

Table contents:

PART I: INTRODUCTION TO BASIC LABORATORY TECHNIQUES. Experiment

1: Introduction to Microscale Laboratory. Experiment

2: Solubility. Experiment

3: Crystallization. Experiment

4: Extraction. Experiment

5: A Separation and Purification Scheme. Experiment

6: Chromatography. Experiment

7: Simple and Fractional Distillation. Experiment

8: Infrared Spectroscopy and Boiling Point Determination. ESSAY: Aspirin. Experiment

9: Acetylsalicylic Acid. ESSAY: Analgesics. Experiment

10: Isolation of the Active Ingredient in an Analgesic Drug. Experiment

11: Acetaminophen. ESSAY: Identification of Drugs. Experiment

12: TLC Analysis of Analgesic Drugs. ESSAY: Caffeine. Experiment

13: Isolation of Caffeine. ESSAY: Esters -- Flavors and Fragrances. Experiment

14: Isopentyl Acetate (Banana Oil). ESSAY: Terpenes and Phenylpropanoids. Experiment

15: Essential Oils: Extraction of Oil of Cloves by Steam Distillation. Essay: Stereochemical Theory of Odor. Experiment

16: Spearmint and Caraway Oil: (+)- and (-)- Carvones. Essay: The Chemistry of Vision. Experiment

17: Isolation of Chlorophyll and Carotenoid Pigments from Spinach. Essay: Ethanol and Fermentation Chemistry. Experiment 18 Ethanol from Sucrose. PART II:

INTRODUCTION TO MOLECULAR MODELING. ESSAY: Molecular Modeling and Molecular Mechanics. Experiment

19: An Introduction to Molecular Modeling. ESSAY: Computational Chemistry -Ab initio and Semiempirical Methods. Experiment

20: Computational Chemistry. PART III: PROPERTIES AND REACTIONS OF ORGANIC COMPOUNDS. Experiment

21: Reactivities of Some Alkyl Halides. Experiment

22: Nucleophilic Substitution Reactions: Competing Nucleophiles. Experiment

23: Synthesis of n-Butyl Bromide and t-Pentyl Chloride. Experiment

24: 4-Methylcyclohexene. ESSAY: Fats and Oils. Experiment

25: Methyl Stearate from Methyl Oleate. ESSAY: Petroleum and Fossil Fuels. Experiment

26: Gas Chromatographic Analysis of Gasolines. ESSAY: Biofuels. Experiment

27: Biodiesel. ESSAY: Green Chemistry. Experiment

28: Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination Using a Chiral Shift Reagent. Experiment

29: Nitration of Aromatic Compounds Using a Recyclable Catalyst. Experiment

30: Resolution of (?????Phenylethylamine and Determination of Optical Purity. Experiment

31: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol. Experiment

32: Multi-Step Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid. Experiment

33: Triphenylmethanol and Benzoic Acid. Experiment

34: Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium Catalyst. Experiment

35: Grubbs-Catalyzed Metathesis of Eugenol with 1,4-Butanediol to Prepare a Natural Product. Experiment

36: Aqueous-based Organozinc Reactions. Experiment

37: The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones). Experiment

38: Preparation of an ???-Unsaturated Ketone via Michael and Aldol Condensation Reactions. Experiment

39: The Wittig Reaction: Preparation of 1,4-Diphenyl-1,3-butadiene. Experiment

40: Relative Reactivities of Several Aromatic Compounds. Experiment

41: Nitration of Methyl Benzoate. ESSAY: Local Anesthetics. Experiment

42: Benzocaine. Experiment

43: Methyl Salicylate (Oil of Wintergreen). ESSAY: Pheromones: Insect Attractants and Repellents. Experiment

44: N,N-Diethyl-m-toluamide: The Insect Repellent "OFF." ESSAY: Sulfa Drugs. Experiment

45: Sulfa Drugs: Preparation of Sulfanilamide. Essay: Polymers and Plastics. Experiment

46: Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene. Essay: Diels-Alder Reactions and Insecticides. Experiment

47: The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride. Experiment

48: Diels-Alder Reaction with Anthracene-9-methanol. Experiment

49: Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone. ESSAY:Fireflies and Photochemistry. Experiment

50: Luminol. ESSAY: The Chemistry of Sweeteners. Experiment

51: Analysis of a Diet Soft Drink by HPLC. PART IV: IDENTIFICATION OF ORGANIC SUBSTANCES. Experiment

52: Identification of Unknowns. PART V: PROJECT-BASED EXPERIMENTS. Experiment

53: Preparation of a C-4 or C-5 Acetate Ester. Experiment

54: Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, Fennel, or Star Anise. Experiment

55: Competing Nucleophiles in SN1 and SN2 Reactions: Investigations using 2Pentanol and 3-Pentanol. Experiment

56: Friedel-Crafts Acylation. Experiment

57: The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry. Experiment

58: The Use of Organozinc Reagents in Synthesis: An Exercise in Synthesis and Structure Proof by Spectroscopy. Experiment

59: Synthesis of Naproxen by Palladium Catalysis. Experiment

60: The Aldehyde Enigma. Experiment

61: Synthesis of Substituted Chalcones: A Guided-Inquiry Experience. Experiment

62: Green Epoxidation of Chalcones. Experiment

63: Cyclopropanation of Chalcones. 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. 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