Cover of the textbook  

The Art of Writing Reasonable Organic Reaction Mechanisms, 3rd edition

(or, How to Pass Your Cumes)

by Robert B. Grossman


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You can order The Art of Writing Reasonable Organic Reaction Mechanisms, 3rd edition, from publisher Springer,, or other vendors for $84.99 or less. (Shop around; you can usually find it on sale somewhere. In order of decreasing cost, hardcover, softcover, and electronic versions are available.)

I teach a two-day "short course" based on this book that is intended for BS- and MS-level organic chemists and PhD-level analytical and biological chemists and chemical engineers in the pharmaceutical and contract synthesis industries. Please contact me if you are interested in bringing me to your company's site to teach the course.

The goal of The Art of Writing Reasonable Organic Reaction Mechanisms (AWRORM) is to teach students how to draw reasonable mechanisms for organic reactions, using the reaction conditions and the nature of the starting materials as a basis for the mechanism. The general approach of the book is to classify reactions according to their mechanisms and the reaction conditions under which they proceed, not according to the transformations they achieve.

AWRORM's level of difficulty is appropriate for students who have taken two semesters of organic chemistry. It is not a new or supplemental textbook for sophomore organic chemistry, nor is it a reference text for students who have already mastered all the intricacies of writing mechanisms. AWRORM assumes that students have a basic knowledge of the conventions of drawing organic structures. However, it also assumes that the students have had very little instruction in mechanistic concepts like nucleophilicity, electrophilicity, and the nature of radical chain reactions.

AWRORM has a number of features that make it different from all the other mechanism textbooks on the market.

  • AWRORM is very much a practical, "how-to" book that is meant to show the student how to think logically and analytically about organic reaction mechanisms. Students are asked to learn how to draw reasonable organic mechanisms for certain reactions; where more than one reasonable mechanism can be written, students are not asked to learn that one is "right" and the other is "wrong." Practical advice is provided to the student on things to do and not to do when drawing mechanisms. "Common error alerts" are scattered throughout the text to alert students to common mistakes and to show how they can avoid them. Worked and unworked examples of each mechanistic type are presented in each section so that the student develops a feel for the most common mechanistic pathways. An overview of the most important points is provided at the end of each chapter.

  • AWRORM is organized to reflect one's thinking as one puzzles through a problem. My philosophy is that a proposed organic chemistry mechanism should flow naturally from the nature of the starting materials and the reaction conditions, and the book is organized to reflect this philosophy. For example, most textbooks discuss electrophilic aromatic substitution and nucleophilic aromatic substitution in the same chapter. By contrast, AWRORM covers nucleophilic aromatic substitution immediately after it covers substitution at carbonyl compounds, because the mechanisms are identical; electrophilic aromatic substitution is discussed in a different chapter.

  • AWRORM is tightly focused. Discussions of theory are kept to a minimum unless the theory impinges directly on how one would draw a mechanism for a reaction in question, and discussions of why reactions choose one course out of many possibilities are also generally omitted (with a few major exceptions). AWRORM is definitely not meant to introduce students to the methods by which mechanisms are determined experimentally (physical organic chemistry), so no discussion of kinetic analysis, isotope effects, Hammett plots, etc. is included. AWRORM is also definitely not intended to teach students how to plan a synthesis.

  • At the end of each chapter is a comprehensive problem set. All problems are drawn from the literature. They vary in difficulty from easy to very challenging, but most can be solved by any student (not only a very talented one) who has made a sincere effort to master the material. (AWRORM is superior to many other textbooks in this regard.) An answer key is provided in a separate volume that can be downloaded directly from Springer at no additional cost, and the solutions therein are written in such a way as to show the student how the answers can be puzzled out.

    New! You can now work the AWRORM end-of-chapter problems in ACE Organic, a Web-based, interactive organic chemistry homework program that tells you why your mechanism is reasonable or unreasonable without giving away the right answer.

  • The material covered in AWRORM reflects the breadth of modern organic chemistry. The book is not meant to be completely comprehensive, but an effort is made to cover the important areas of organic synthesis. Reactions which are not used widely or have been largely supplanted are generally not discussed, and newer reactions and reagents are often mentioned. For example, cycloaromatizations are discussed as a fundamentally new method for generating radicals. At the same time, the importance of classical chemistry in modern synthesis is not ignored.

  • A unique feature of this book among organic mechanism books is the inclusion of a chapter on transition-metal-mediated and -catalyzed reactions. A working knowledge of the mechanisms of these reactions is indispensable to the practicing organic chemist, yet they are usually not discussed in organic chemistry textbooks or classes. Organometallic textbooks cover these subjects in detail, but usually from the perspective of an inorganic chemist, not from that of an organic chemist trying to puzzle his or her way through a mechanism.

Please note: AWRORM is not a physical organic chemistry textbook! It is my experience that students cannot learn physical organic chemistry, the experimental methods by which proposed organic reaction mechanisms are tested, if they cannot propose a reasonable mechanism for an organic reaction in the first place. AWRORM is intended to be used in a course that intervenes between sophomore organic chemistry and physical organic chemistry. It is not intended to replace textbooks such as Lowry & Richardson, Carey & Sundberg Part A, or Carroll. Many schools do not offer a course in "electron-pushing", expecting their graduate students either to have learned this material as an undergraduate or to pick it up on their own; students at schools such as these would benefit greatly from studying AWRORM on their own.

By the time you have finished studying AWRORM, you should have a much better understanding of why organic reactions proceed in the way they do. You should also find it much easier to pass your cumes (written qualifying examinations)!

Learn more about Robert B. Grossman or his research program in synthetic organic chemistry.