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Synopsis Every aspiring organic chemist must learn to write reasonable mechanisms for organic reactions, yet few textbooks are devoted to teaching them how to do it. This text will help students and researchers in organic chemistry and allied fields to develop this indispensable skill. Novel attributes of the text include an informal writing style, "common error alerts", numerous problems of an appropriate level of difficulty, and worked answers to all problems available for download from the Internet at no charge. The text is unique in its inclusion of a chapter on reactions mediated or catalyzed by transition metals. Relatively new topics such as olefin metathesis and cycloaromatization are covered without giving short shrift to more traditional areas such as carbonyl chemistry. This second edition is thoroughly revised: mechanisms updated, discussion of aromaticity, acidity, and stereochemistry expanded, the chapters on free-radical reactions and metal-mediated and metal-catalyzed reactions reorganized, and new problems added.