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Developing the green organic program at the University of Oregon, Kenneth Doxsee and James Hutchison saw the urgent need and rapidly growing demand for green chemistry laboratory materials. This lab text describes the tools and strategies of green chemistry, and the lab experiments that allow investigation of organic chemistry concepts and techniques in a greener laboratory setting. GREEN ORGANIC CHEMISTRY: STRATEGIES, TOOLS AND LABORATORY EXPERIMENTS was developed and successfully tested as a direct replacement of the traditional organic chemistry laboratory curriculum. Thus, the conceptual themes and experimental techniques important to the modern practice of organic chemistry can be taught in the context of more environmentally-benign laboratory experiments. Students acquire the tools to assess the health and environmental impacts of chemical processes and the strategies to improve develop new processes that are less harmful to human health and the environment. The curriculum introduces a number of state-of-the-art experiments and reduces reliance on expensive environmental controls, such as fume hoods.
Graphical Abstracts for the Experiments.
2. IDENTIFICATION AND EVALUATION OF CHEMICAL HAZARDS.
3. CHEMICAL EXPOSURE AND ENVIRONMENTAL CONTAMINATION.
4. SOURCES OF INFORMATION ABOUT CHEMICAL HAZARDS.
5. INTRODUCTION TO GREEN CHEMISTRY.
6. ALTERNATIVE SOLVENTS.
7. ALTERNATIVE REAGENTS.
8. REACTION DESIGN AND EFFICIENCY.
9. ALTERNATIVE FEEDSTOCKS AND PRODUCTS.
10. THE BIG PICTURE AND GREEN CHEMISTRY METRICS.
11. PREFACE TO THE EXPERIMENTAL SECTION.
Experiment 1: Solventless Reactions: The Aldol Reaction.
Experiment 2: Bromination of An Alkene: Preparation of Stilbene Dibromide.
Experiment 3: A Greener Bromination of Stilbene.
Experiment 4: Preparation and Distillation of Cyclohexene.
Experiment 5: Synthesis and Recrystallization of Adipic Acid.
Experiment 6: Oxidative Coupling of Alkynes: The Glaser-Eglinton-Hay Coupling.
Experiment 7: Gas-Phase Synthesis, Column Chromatography and Visible Spectroscopy of 5,10,15,20-Tetraphenylporphyrin.
Experiment 8: Microwave Synthesis of 5,10,15,20-Tetraphenylporphyrin.
Experiment 9: Metallation of 5,10,15,20-Tetraphenylporphyrin.
Experiment 10: Measuring Solvent Effects: Kinetics of Hydrolysis of tert-Butyl Chloride.
Experiment 11: Molecular Mechanics Modeling.
Experiment 12: Electrophilic Aromatic Iodination.
Experiment 13: Palladium-Catalyzed Alkyne Coupling/Intramolecular Alkyne Addition: Natural Product Synthesis.
Experiment 14: Resin-Based Oxidation Chemistry.
Experiment 15: Carbonyl Chemistry: Thiamine-Mediated Benzoin Condensation of Furfural.
Experiment 16: Solid-Phase Photochemistry.
Experiment 17: Applications of Organic Chemistry: Patterning Surfaces With Molecular Films.
Experiment 18: The Friedel-Crafts Reaction: Acetylation of Ferrocene.
Experiment 19: Combinatorial Chemistry: Antibiotic Drug Discovery.
Appendix A: The Twelve Principles of Green Chemistry.
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