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Organic Chemistry: Mechanistic Patterns, 2nd Edition

By William Ogilvie, Nathan Ackroyd, C. Scott Browning, Ghislain Deslongchamp, Felix Lee, Effie Sauer

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ISBN-13: 9781774940419
Publisher: Top Hat
Edition: 2nd

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. Including Ghislain Deslongchamps’ acclaimed Organic ChemWare Learning Objects that bring static textbook molecular representations to life (including orbital depictions and energy graphs in many of the interactives) combined with Top Hat's active learning framework, the author's goal is to help students learn to think like chemists and be more successful in the course.


  • Lone pairs have been added to reaction sites in ch. 8-20, increasing the mechanistic focus of the text. 

  • Chapter 2 includes nomenclature of different functional groups and multiple functional groups in a molecule. Solutions have been updated to be more consistent.

  • Chapter 3 includes new representations of Newman projections to better illustrate conformational relationships. All of the Newman projections throughout the text have been updated accordingly.

  • Chapter 5 adds more complete descriptions of different arrow styles for p and s electron movements. The descriptions of delocalization and resonance have also been improved to address common student issues and misconceptions.

  • Chapter 6 has improved end-of-chapter questions.

  • Chapter 8 has been expanded to better accommodate alkyne reactions and descriptions of stereoselectivity and stereospecificity.

  • Chapter 11 sections of the prediction of reaction pathways have been expanded and clarified. Additional explicit descriptions of reaction pathways are shown to better highlight the sequence of events with different types of catalysis.

  • Chapter 15 sees an increased section clarifying the patterns of carbonyl displacements.

  • Chapter 16 includes modifications to the description of anomers and of imine reactivity.

  • Chapters 17 and 18 feature a reorganization of the patterns section to better group reactions by nucleophile type.

  • Chapter 19 has an improved section of dissolving metal reactions, modified to reflect current research. The section describing reaction patterns has been completely re-written and re-organized.

  • Auto-gradable mechanism drawing functionality. 

  • A reaction index sorted by functional group. This index also serves as a handy reference for both students and instructors.

  • An abbreviation index that includes selected descriptions and structures.

Table of Contents

About the Authors ix 

Foreword xi 

Preface xii 

CHAPTER 1 Carbon and Its Compounds 1 

CHAPTER 2 Anatomy of an Organic Molecule 47 

CHAPTER 3 Molecules in Motion: Conformations by Rotations 86 

CHAPTER 4 Stereochemistry: Three-Dimensional Structure in Molecules 125 

CHAPTER 5 Organic Reaction Mechanism: Using Curved Arrows to Analyze Reaction Mechanisms 186 CHAPTER 6 Acids and Bases 235 

CHAPTER 7 π Bonds as Electrophiles: Reactions of Carbonyls and Related Functional Groups 272 CHAPTER 8 π Bonds as Nucleophiles: Reactions of Alkenes, Alkynes, Dienes, and Enols 328 

CHAPTER 9 Conjugation and Aromaticity 398 

CHAPTER 10 Synthesis Using Aromatic Materials: Electrophilic Aromatic Substitution and Directed Ortho Metalation 431 

CHAPTER 11 Displacement Reactions on Saturated Carbons: SN1 and SN2 Substitution Reactions 494 CHAPTER 12 Formation of π Bonds by Elimination Processes: Elimination and Oxidation Reactions 540 CHAPTER 13 Structure Determination I: Nuclear Magnetic Resonance Spectroscopy 577 

CHAPTER 14 Structure Determination II: Mass Spectrometry and Infrared Spectroscopy 648 

CHAPTER 15 π Bond Electrophiles Connected to Leaving Groups: Carboxylic Acid Derivatives 

and Their Reactions 696 

CHAPTER 16 π Bonds with Hidden Leaving Groups: Reactions of Acetals and Related Compounds 764 CHAPTER 17 Carbonyl-Based Nucleophiles: Aldol, Claisen, Wittig, and Related Enolate Reactions 810 CHAPTER 18 Selectivity and Reactivity in Enolate Reactions: Control of Stereoselectivity and 

Regioselectivity 899 

CHAPTER 19 Radicals: Halogenation, Polymerization, and Reduction Reactions 971 

CHAPTER 20 Reactions Controlled by Orbital Interactions: Ring Closures, Cycloadditions, and 

Rearrangements 1011 

Appendix A Answers to Checkpoint Problems A-1 

Appendix B Common Errors in Organic Structures and Mechanisms A-137 

Appendix C pKa Values of Selected Organic Compounds A-141 

Appendix D NMR and IR Spectroscopic Data A-143 

Appendix E Periodic Table of the Elements A-145 

Glossary G-1 

Index I-1 

Author Information

William Ogilvie, Ph.D., is a professor in the Department of Chemistry and Biomolecular Sciences 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, and the Excellence in Teaching Award by the University of Ottawa in 2017. He is currently the director of the Biopharmaceuticals Sciences program at the university.

Nathan Ackroyd, Ph.D., is a 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, Ph.D., 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, Ph.D., was a NSERC Postgraduate PhD student at the University of New Brunswick (UNB) and NSERC Postdoctoral fellow at the Massachusetts Institute of Technology. He is a chemistry professor at UNB and is active in the research fields of molecular recognition, organocatalysis, computer-assisted molecular design, new bonding models, and visualization in chemical education. He has always shown a strong commitment to teaching and how technology can help students learn more effectively. Developing new interactive visualization tools for chemical education, he is the creator of Organic Chemistry Flashware, and Organic ChemWare. He has been recognized by Maclean's magazine as one of UNB's top professors. Dr. Deslongchamps is a past director of the Shad Canada program at UNB.

Felix Lee, Ph.D., is a teaching 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 Director of the Integrated Science program, a high-impact program for students who have a passion for science and scientific discovery.

Effie Sauer, Ph.D., 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.