The Art of Writing Reasonable Organic Reaction Mechanisms

by Robert B. Grossman

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, and “common error alerts” are scattered throughout the text to warn readers about pitfalls and misconceptions that bedevil students. Each chapter is capped by a large problem set.

The author has drawn on his own research and the current literature to ensure that appropriate attention is given to topics across the range of modern organic chemistry. The text is unique inits inclusion of a chapter on reactions mediated or catalyzed by transition metals, an area in which mechanistic understanding is now essential. More modern topics such as olefin metathesis and cycloaromatization are covered without giving short shrift to more traditional areas such as carbonyl chemistry. The text assumes a basic knowledge of organic chemistry. It can be used either in a formal course or by students working on their own, and will be particularly useful for graduate students studying for qualifying examinations. It will also be useful to students and researchers in biochemistry, pharmacology, and inorganic chemistry.

The third edition includes greater discussion of the reactions of biological cofactors such as thiamine and pyridoxal, and discussions of modern developments such as metal-catalyzed C–H activation reactions have been added. In terms of stylistic improvements, the author has introduced color into drawings to improve visual clarity and has improved the depictions of radical anions and radical chain reactions.       

Genres: Chemistry, Science, Reference, Nonfiction

699 pages, Kindle Edition

First published January 1, 2002

Reviews

[Robert Vincent · Rating 5 out of 5]

I am a chemist by education and occupation but I have always had difficulty figuring out the most reasonable (very aptly chosen word for the title) reaction mechanism for whatever organic reaction I run across. Sure, I can come up with a reaction mechanism but sometimes the mechanism I come up with does not hold up to scrutiny. I bought this book to try to better myself in that regard. The book itself is a little learning course, complete with exercises (answers are online) that progresses at a reasonable pace. I was able to follow through on my own and come out of reading (and studying) this book much better able to apply the knowledge I already had in a more focused manner. I would highly recommend this text for anyone trying to better their own understanding of reaction mechanisms or people that have difficulty picking a favorite of many possible reaction paths.

[Harish Suryadevara · Rating 5 out of 5]

An excellent introduction to more complex topics in organic chemistry - the use of molecular orbital explanations throughout are particularly useful. Section on pericyclic reactions and free radical chemistry are great introductions to the subjects, and the reaction problems are challenging yet useful. The section on organometallic chemistry seems a bit crammed - I would use a separate book if you're interested. Overall, great book - certainly worth reading if you're interested in learning more about organic chemistry

[Bella Liffick · Rating 1 out of 5]

He's no David Klein

[Sanjay Pandiri · Rating 4 out of 5]

Good textbook. Grossman disrespects the cyclopropylmethyl cation, however.

[Harrison · Rating 5 out of 5]

beautiful!

[Senka Colo · Rating 5 out of 5]

I found this book to be probably one of the best books out there on the topic.