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The Art of Writing Reasonable Organic Reaction Mechanisms

Robert B. Grossman

Hardcover, 456 Pages
3rd Edition - 2019
ISBN: 3030287327
Springer, Berlin


Intended for students of intermediate organic chemistry, this text shows how to write a reasonable mechanism for an organic chemical transformation. The discussion is organized by types of mechanisms and the conditions under which the reaction is executed, rather than by the overall reaction as is the case in most textbooks. The treatment emphasizes unifying principles, showing how common mechanisms link seemingly disparate reactions. Each chapter discusses common mechanistic pathways and suggests practical tips for drawing them. Worked problems are included in the discussion of each mechanism.

Editorial Review

One's approach to reaction mechanisms is a matter of preference. Students can either employ the underlying mechanistic principles in their analysis, or get around the problem of solving the Gordian knot by painstakingly committing the mechanism for every single (name) reaction in the repertoire to memory.

In principle, most mechanisms are derived from a basis set of fundamental steps. These fundamentals must be learned, applied, and practiced. Only then will one be in a position to rationalize complex transformations in mechanistic terms. Once these skills are mastered, it is a simple matter to sketch out a mechanistic pathway for a given set of reactants and products within a short while.

Grossman has succeeded in explaining these fundamentals in detail in an easily accessible monograph. He also comments on several common pitfalls and mistakes. Readers can reinforce their incipient skills with practical illustrations, and are challenged throughout with complicated examples. The solutions to these problems are available on the internet.

With the basic knowledge from an introductory course and a textbook at the ready, the present text offers additional lucid explanations and ideal opportunities for practice. This work will thus be indispensable for students who are interested in mechanisms, or who wish to gain additional perspective. This reviewer is certain that reading Grossman's book will help avoid making errors on exams! This is despite, and perhaps because of, the fact that its focus is on the underlying fundamental steps of mechanisms.


1 The Basics. 2 Polar Reactions under Basic Conditions. 3 Polar Reactions under Acidic Conditions. 4 Pericyclic Reactions. 5 Free-Radical Reactions. 6 Transition-Metal-Mediated and -Catalyzed Reactions. 7 Mixed-Mechanism Problems.