Nelson Higher Education

Higher Education

Organic Chemistry: Mechanistic Patterns, 1st Edition

  • William Ogilvie
  • Nathan Ackroyd
  • C. Scott Browning
  • Ghislain Deslongchamps
  • Felix Lee
  • Effie Sauer
  • ISBN-10: 017650026X
  • ISBN-13: 9780176500269
  • 0 Pages | Hardcover
  • COPYRIGHT: 2018 Published
Request a Copy for Review


About the Product

Organic Chemistry: Mechanistic Patterns is the very first introductory organic chemistry title that holistically focuses on a mechanistic approach; an approach that has proven to achieve a deeper understanding of chemical reactivity. This mechanistic approach to the dynamic world of organic chemistry visualizes reactivity as a collection of patterns in electron movement, making it possible for students to describe why a reaction occurred. Recognizing patterns of electron flow between seemingly different reactions can allow students to predict how a chemical will react, even if they have never seen a particular reaction before. The text takes great care to establish a progression of reactivity, from simple to complex, introducing functional groups as necessary, while focusing on the reaction at hand rather than the various things that each functional group does. To help students further visualize key concepts, the text includes Ghislain Deslongchamps’ acclaimed Organic ChemWare; interactive animations and simulations that bring static textbook molecular representations to life. Together, we seek to open students’ eyes to the dynamic world of organic chemistry with a more powerful and systematic approach to learning.

About the Author

William Ogilvie

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.

Nathan Ackroyd

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.

C. Scott Browning

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.

Ghislain Deslongchamps

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.

Felix Lee

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.

Effie Sauer

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.

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

New to this edition

  • CONTEXT-RICH. Each chapter begins with Why It Matters, which invites students to buy into their learning by showing them the relevance of the material about to be covered. Chemistry: Everything and Everywhere boxes describe applications or stories related to the material in the text. Did You Know boxes provide extra detail about chemical reactivity, deeper explanation of concepts, or information beyond the scope of the text.
  • VISUALIZATION TOOLS. Over 185 Organic ChemWare digital learning objects support and reinforce the mechanistic philosophy of the text, making a direct connection between static imagery in the text and the dynamic reaction processes they represent. In addition, carefully constructed figures with call-outs bring static figures to life by guiding students through each step of a given reaction or chemical process.
  • JUST-IN-TIME FEEDBACK. Checkpoints, grounded in class-tested pedagogical research, follow the description of key material in the text and inform students explicitly about what they should now be able to do or understand, illustrated with a solved problem. Related exercises are included together with a problem that integrates several ideas together. Student Tips help students avoid common pitfalls.
  • REVIEW AND MASTER. The Patterns in… sections tie together the concepts shown in the chapter in a visual way. Reactions and structures are aligned to highlight repeating electron flows or controlling elements, with some text to describe the key reactivity patterns. This is intended as a study guide to help reduce memorization by showing how key reactions are related. You Can Now lists the skills that each student should have acquired by reading the text and completing the questions and exercises. Mechanistic Re-View is a list of the reactions (with mechanisms) that were described in each chapter. For the advanced student, Want to Learn More provides online content that describes a topic in more detail. These illustrate a reaction or concept beyond the scope of the text, but which may be of interest to advanced students or to those who use the book as a reference.
  • PRACTICE. PRACTICE. PRACTICE. End-of-chapter exercises allow students to learn by doing homework and practicing on their own. The more practice they do, the better they become at a particular skill. With our text, we have tried to organize things in a way that makes the subject clear, follows patterns, and is understandable.


All supplements have been updated in coordination with the Main title.
Please see Main title page for new to this edition information.

Instructor Supplements

Online Only Instructor Resources for Ogilvie's Organic Chemistry, First Edition  (ISBN-10: 0176700080 | ISBN-13: 9780176700089)
Kit: Organic Chemistry Mechanistic Patterns 1e + Student Solution Manual + Printed Access Cards for Mobius and Organic Chemware Companion Site (12 Months/Multi Term)  (ISBN-10: 0176869603 | ISBN-13: 9780176869601)

Student Supplements

Kit: Organic Chemistry Mechanistic Patterns 1e + Student Solution Manual + Printed Access Cards for Mobius and Organic Chemware Companion Site (12 Months/Multi Term)  (ISBN-10: 0176869603 | ISBN-13: 9780176869601)