Operational Organic Chemistry

For sophomore-level organic lab courses. This text/lab manual helps students master the fundamental laboratory operations of organic chemistry and develop critical thinking skills through scientific problem solving.

Preface To the Instructor Acknowledgments Introduction Problem Solving in the Organic Chemistry Laboratory Scientific Methodology Organization of This Book A Guide to Success in the Organic Chemistry Lab Laboratory Safety Safety Standards Protecting Yourself Preventing Laboratory Accidents Reacting to Accidents: First Aid Reacting to Accidents: Fire Chemical Hazards Finding and Using Chemical Safety Information Chemistry and the Environment Disposal of Hazardous Wastes Green Chemistry Part I Mastering the Operations 1 The Effect of pH on a Food Preservative 2 Separating the Components of ldquo;Panacetinrdquo; 3 Identifying a Constituent of ldquo;Panacetinrdquo; 4 Synthesis of Salicylic Acid from Wintergreen Oil 5 Preparation of Synthetic Banana Oil 6 Separation of Petroleum Hydrocarbons 7 A Green Synthesis of Camphor 8 Identification of a Petroleum Hydrocarbon 9 Isolation and Isomerization of Lycopene from Tomato Paste 10 Isolation and Identification of the Major Constituent of Clove Oil 11 Identification of Unknown Ketones 12 The Optical Activity of -Pinene: A Chemical Mystery Part 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 S N 1 Solvolysis Reaction 20 Reaction of Iodoethane with Sodium Saccharin, an Ambident Nucleophile 21 Dehydration of Methylcyclohexanols and the Evelyn Effect 22 Testing Markovnikovrsquo;s Rule 23 Stereochemistry of Bromine Addition totrans-Cinnamic Acid 24 A Green Synthesis of Adipic Acid 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 TritylCarbocation 31 An Unexpected Reaction of 2,3-Dimethyl-2,3-butanediol 32 Identification.

This comprehensive laboratory text provides a thorough introduction to all of the significant operations used in the organic lab and includes a large selection of traditional-scale and microscale experiments and minilabs. Its unique problem-solving approach encourages students to think in the laboratory by solving a scientific problem in the process of carrying out each experiment. The Second Edition contains a new introductory section, "Chemistry and the Environment," which includes a discussion of the principles of green chemistry. Several green experiments have been added, and some experiments from the previous editions have been revised to make them greener.

This book describes the fascinating chemistry of the many kinds of organic compounds of hypervalent iodine. Each chapter deals with a particular iodine compound or families of compounds which have been used as reagents in a plethora of useful transformations. These include assorted oxidation, such as with the precious Dess-Martin reagent as well as with a wide range of further reactions. Prominent features of hypervalent iodine reagents derived from iodobenzene are: ready availability, operational simplicity, mild reaction conditions, and high efficiency. They are environmentally safe and can be recycled. New species may be easily prepared by introducing substituents in the benzene ring or changing the ligand attached to iodine. Their combination with other reagents broadens considerably their synthetic potential. Today, no synthetic chemist can afford to ignore the valuable hypervalentiodine reagents. Key Features * Features up-to-date coverage of a wide range of topics * Includes many tables featuring a diversity of reactivity, and a comprehensive index * Acts as a comprehensive, up-to-date reference on all aspects of hypervalent iodine chemistry * Contains a section on unusual efficiency of hypervalent iodine reactions