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Organic Chemistry


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Table of Contents

Chapter 1: Carbon and Its Compounds Chapter 2: Anatomy of an Organic Molecule Chapter 3: Molecules in Motion: Conformations by Rotations Chapter 4: Stereochemistry: Three-Dimensional Structure in Molecules Chapter 5: Organic Reaction Mechanism: Using Curved Arrows to Analyze Reaction Mechanisms Chapter 6: Acids and Bases Chapter 7: Bonds as Electrophiles: Reactions of Carbonyls and Related Functional Groups Chapter 8: Bonds as Nucleophiles: Reactions of Alkenes, Alkynes, Dienes, and Enols Chapter 9: Conjugation and Aromaticity Chapter 10: Synthesis Using Aromatic Materials: Electrophilic Aromatic Substitution and Directed Ortho Metalation Chapter 11: Displacement Reactions on Saturated Carbons: SN1 and SN2 Substitution Reactions Chapter 12: Formation of Bonds by Elimination Processes: Elimination and Oxidation Reactions Chapter 13: Structure Determination I: Nuclear Magnetic Resonance Spectroscopy Chapter 14: Structure Determination II: Mass Spectrometry and Infrared Spectroscopy Chapter 15: Bond Electrophiles Connected to Leaving Groups: Carboxylic Acid Derivatives and Their Reactions Chapter 16: Bonds with Hidden Leaving Groups: Reactions of Acetals and Related Compounds Chapter 17: Carbonyl-Based Nucleophiles: Aldol, Claisen, Wittig, and Related Enolate Reactions Chapter 18: Selectivity and Reactivity in Enolate Reactions: Control of Stereoselectivity and Regioselectivity Chapter 19: Radicals: Halogenation, Polymerization, and Reduction Reactions Chapter 20: Reactions Controlled by Orbital Interactions: Ring Closures, Cycloadditions, and Rearrangements Appendix A: Answers to Checkpoint Problems Appendix B: Common Errors in Organic Structures and Mechanisms Appendix C: pKa Values of Selected Organic Compounds Appendix D: NMR and IR Spectroscopic Data Appendix E: Periodic Table of the Elements

About the Author

Scott Browning is Senior Lecturer and a faculty member at the University of Toronto. His research interests are in chemical education, particularly scientific literacy and technology-based learning and instruction in post-secondary science education. Included in his research are best practices in science instruction-particularly as it relates to the role of technology in learning and teaching-and the involvement of undergraduates in meaningful current scientific research. At the intersection of these domains, he is also working with undergraduate students using higher level methods in computational chemistry to better understand molecular processes in both the biochemical and chemical realms. Dr. Browning is very involved in chemical education at the University of Toronto and across the province and in 2009 was the organizer of the Ontario Chemistry Olympiad. Effie Sauer, is an associate professor, teaching stream, in the Department of Physical and Environmental Sciences at the University of Toronto (Scarborough). With the department since 2009, she has taught a variety of courses including general, organic, and green chemistry. In 2012, Dr. Sauer was honoured to be named one of UTSC's Professors of the Year by the student-run newspaper, The Underground. More recently, she was awarded the UTSC Faculty Teaching Award (2013). Prior to her appointment at UTSC, Dr. Sauer completed her PhD at the University of Ottawa (2007), followed by a postdoctoral fellowship at Yale University. William Ogilvie is an associate professor in the Department of Chemistry at the University of Ottawa. He was an NSERC 1967 Scholar who received his PhD from the University of Ottawa in 1989. Following this, he was an NSERC postdoctoral fellow at the University of Pennsylvania and at the Scripps Research Institute. In 1990, he joined Boehringer-lngelheim Pharmaceuticals (then BioMega) in Montreal, working as a research scientist, and spent 11 years in the industry before moving to uOttawa. His teaching focus has been organic and medicinal chemistry, and he has also taught large classes of science for non-scientists. He was awarded the Excellence in Education Prize by the University of Ottawa in 2006. Ghislain Deslongchamps is Professor and Chair of Chemistry at the University of New Brunswick. Upon joining the department, he quickly established a name for himself in the research field of molecular recognition. His research interests currently include organocatalysis, computer-assisted molecular design, and visualization in chemical education. He has always showed a strong commitment to teaching and how technology can help students learn more effectively. He has been recognized by Maclean's magazine as one of UNB's top professors. Developing new computer-based visualization techniques for chemical education since 2000, he is the creator of Organic Chemistry Flashware, published by Nelson Education. Dr. Deslongchamps is a past director of the SHAD program at UNB, Canada's top summer enrichment program, which empowers exceptional high school students. Nathan Ackroyd is an associate professor of Chemistry and a faculty member at Mount Royal University in Calgary. He has always been interested in how the world works as it does. Trying to find detailed answers to broad questions led him to an early interest in chemistry and physics. After earning a Bachelor of Science in Chemistry from Brigham Young University, he moved to the University of Illinois, where he focused on the organic synthesis of imaging agents to simplify the diagnosis of breast tumours. In addition to Organic Chemistry, Dr. Ackroyd teaches Biochemical Pharmacology and Drug Discovery for fourth-year biology students. Through these courses, he hopes to increase students' understanding of how the chemicals we are made of interact with the chemicals we use every day. Felix Lee is an assistant professor in the Department of Chemistry at The University of Western Ontario. Dr. Lee is a two-time recipient of the University Student's Council Award, The Bank of Nova Scotia Award, and Western Alumni Association Teaching Award, as well as a recipient of a Marilyn Robinson Award for Excellence in Teaching. As one student describes, "He has not only turned my most hated subject into my favourite; he has inspired me to do well in subsequent courses and life events." According to another professor, "He is obviously recognized as an excellent teacher, and now he is helping the faculty by being a teacher's teacher." Dr. Lee has extensively been involved in the restructuring of first-year chemistry at The University of Western Ontario, and he is currently a co-director of the new Western Integrated Science program.

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