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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 in its inclusion of a chapter on reactions mediated or catalyzed by transition metals, an area in which mechanistic understanding is now essential. Relatively new 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.
|Publisher:||Springer New York|
|Edition description:||2nd ed. 2003. Corr. 4th printing 2007|
|Product dimensions:||6.10(w) x 9.25(h) x 0.03(d)|
Table of Contents
- Preface to the Student
- Preface to the Instructor
- 1: The Basics ..... 1
- 2: Polar Reactions under Basic Conditions ..... 48
- 3: Polar Reactions under Acidic Conditions ..... 98
- 4: Pericyclic Reactions ..... 139
- 5: Free-Radical Reactions ..... 212
- 6: Transition-Metal-Catalyzed and -Mediated Reactions ..... 256
- 7: Mixed-Mechanism Problems ..... 310
- A Final Word ..... 315
- Index ..... 317
- Preface to the Instructor
The book is organized by mechanistic types. The first chapter covers such fundamental concepts as formal charges, curved-arrow formalisms, acidity and basicity, nucleophilicity and electrophilicity, and methods for identifying which of the five classes of mechanisms is operative in a particular reaction. The following five chapters cover polar reactions under basic conditions, polar reactions under acidic conditions, pericyclic reactions, free-radical reactions, and metal-mediated and -catalyzed reactions, and the final chapter consists of a mix of problems. Each chapter discusses and provides examples of common mechanistic pathways. In addition to problems scattered throughout the text, a very large problem set is found at the end of the chapter; the answers are available for free from the publisher's Web site.
The "Common Error Alerts" are a unique feature of this book. A reasonable mechanism is simply one in which no step is unreasonable, so if you can learn what not to do when drawing a mechanism, you will be well ahead of the game. The Common Error Alerts are scattered throughout the text, warning you of common pitfalls and pointing out how to avoid them.
The Art of Writing Reasonable Organic Reaction Mechanisms book can be used as a textbook for advanced undergraduates or beginning graduate students. It will be especially valuable to beginning graduate students who are struggling through their cumes (written qualifying examinations). The book will be useful not only to chemistry students, but also to students in allied fields such as biochemistry, medicinal chemistry, and pharmacy.