Introductory Organic Reaction Mechanisms Textbook

Introductory Organic Reaction Mechanisms: A color-coded approach to arrow pushing is available in hard copy via Lulu and Amazon.  It is also available in electronic form at Scribd.

Check out excerpts from the book at


To master Organic Chemistry, it is essential to master mechanism. Think about three of the most common types of questions on Organic Chemistry exams. You are often asked to predict the product of a chemical reaction, to draw the reaction mechanism, or to devise a synthesis of an organic molecule. None of these questions can be answered reliably unless you know how the reactions work, and that is what mechanism tells us. This book uses a novel approach to help you better understand the mechanisms of organic transformations.

The mechanisms of 80 common organic reactions are presented herein. Each one is color coded so that you can clearly see the changes that take place during the reaction. The electrons involved in the mechanism are color coded, as are the arrows originating from those electrons and the bonds or lone pairs formed by them in the intermediates and product. As a result, you can trace specific pairs of electrons through an entire transformation. The description of what each mechanistic arrow means is color coded correspondingly so that it is easy to match up the text with the relevant portion of a reaction diagram.

There are 80 entries in this book, one for each reaction mechanism. Within these entries, you will find an overview of the reaction, a generic mechanism, a mechanism for a specific example, and a reaction summary. Where it is relevant, you will also find sections devoted to subtleties such as regiochemistry, stereochemistry, and/or carbocation rearrangement. The reactions are divided among the substrates whose behavior they describe. You will find acid-base chemistry along with reactions of alkanes, alkyl halides, alcohols, ethers, alkenes, alkynes, dienes, aromatic rings, aldehydes and ketones, carboxylic acid derivatives, alpha carbons, and amines. This categorization allows you to easily match up topics in this book with the topics you are covering in your Organic Chemistry class. If you are reviewing for the GRE, MCAT, or other standardized exams, you may find it more efficient to review the concise mechanistic entries in this book than to review all of your original course notes.

I hope that this book will be a helpful resource for students who are taking Organic Chemistry for the first time, as well as for those who are reviewing the course material for one reason or another. Once you have mastered the mechanisms in this book, you will find it easier to rationally predict reaction products. You will also find it easier to propose thoughtful syntheses. You might even find yourself using colored pencils or pens as you draw mechanisms! I hope that you will enjoy this book and that it will make it easier for you to learn Organic Chemistry.

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