Modern Advanced Organic Chemistry

Reactivity Principles in Synthetic Organic Chemistry

David A. Evans
Harvard University

Arthur J. Catino
Harvard University


Modern Advanced Organic Chemistry is a textbook designed to introduce upper-level undergraduates and beginning graduate students to advanced topics in organic chemistry. Based on the legendary notes developed by Evans and his group at Harvard University, this first-of-its-kind textbook discusses the fundamental principles of reactivity in organic chemistry. Most physical and synthetic organic chemistry textbooks tend to be quantitative and "methods-oriented." This book is qualitative and "problem-oriented"—thus easily understood and applied. The authors begin with an in-depth discussion of the universal effects that govern structure and reactivity—steric, electronic, and stereoelectronic effects. The next two chapters explore core concepts such as bonding phenomena, Frontier Molecular Orbital theory, and conformational analysis. After establishing this foundation, the authors introduce various classes of reactions such as olefin and carbonyl additions, pericyclic reactions, elimination/fragmentation, and photochemistry, just to name a few. Carbocations, carbanions, radicals, and carbenes (the reactive intermediates of carbon) are each examined as well. Finally, recent developments in organic chemistry are also discussed such as organocatalysis and inversion operator chemistry. Up-to-date citations provided throughout the text allow further reading and make it an invaluable reference device. For those that find modern advanced organic chemistry to be hopelessly complex, this textbook demonstrates that there is an attainable simplicity that lies beyond complexity.

The Authors

David A. Evans received his A.B. degree from Oberlin College in 1963. He obtained his Ph.D. at the California Institute of Technology in 1967, where he worked under the direction of Professor Robert E. Ireland. In that year he joined the faculty at the University of California, Los Angeles. In 1973 he was promoted to the rank of Full Professor and shortly thereafter returned to Caltech where he remained until 1983. In that year he joined the Faculty at Harvard University and in 1990 he was appointed as the Abbott and James Lawrence Professor of Chemistry. In July of 1998 he completed his three-year term as chair of the Harvard Department of Chemistry and Chemical Biology. Evans has received numerous honors and awards such as theACS Award for Creative Work in Synthetic Organic Chemistry (1982), the Arthur C. Cope Scholar Award (1988), the Yamada Prize (1997), the Tetrahedron Prize (1998), the Robert Robinson Award (1998), the Prelog Medal (1999), the Arthur C. Cope Award (2000), the Distinguished Alumni Award from California Institute of Technology (2002), the Nagoya Medal (2003), the Karl Ziegler Prize (2003), the Gibbs Medal (2005), The Seaborg Medal (2007), the H. C. Brown Award (2007), and the 2012 Welch Award.  Evans’ research interests focus on the design of stereoselective reactions and the application of these reactions to natural product synthesis.

Arthur J. Catino received his B.A. degree in chemistry with Honors from Franklin & Marshall College in 2000. In 2006, he received his Ph.D. at University of Maryland working with Professor Michael P. Doyle where he developed a number of reactions catalyzed by dirhodium complexes for the oxidative functionalization of C-C and C-H bonds. During this time, he was awardedan Organic Division Fellowship from the Chemical Society. In 2007 he joined the laboratory of Professor David A. Evans at Harvard University as a National Institutes of Health Postdoctoral Fellow and initiated a new strategy for the total synthesis of phorbol. Catino’s current research interests focus on the use of macrocyclic stereocontrol in total synthesis.

If you would like to be contacted when this book is published, send a message to Please be sure to include the book's title.