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Reactive Intermediates in Organic Chemistry: Structure, Mechanism, and Reactions



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Author: Maya Shankar Singh

Publisher: Wiley-VCH

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Publish Date: April 21, 2014

ISBN-10: 3527335943

Pages: 296

File Type: PDF

Language: English

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Book Preface

Organic chemistry has always been, and continues to be, the branch of chemistrythat best connects structure with properties, which attracts particular attention because of its immense importance to life and society. Organic synthesis is a creative science involving the construction and cleavage of bonds, the strategies for which represent the central theme in organic synthesis. More than any other branch of organic chemistry, synthesis has improved our understanding of the structure, dynamics, and transition of molecules. Most synthetic problems have more than one solution, and the trick is to judge which of these is likely to have the best chance of success. Even the most experienced chemists develop routes that work well on paper but fail miserably in the laboratory. However, there are some guidelines and principles that are helpful in designing a suitable route for a particular synthesis. Whether one seeks to understand nature or to create the new materials and medicines of the future, a key starting point is thus to understand structure and mechanism of a particular reaction. For synthetic chemists it is very important to understand in detail what is going on when the molecules in the starting materials react with each other and create the molecules characteristic of the product. Knowledge about mechanisms makes it possible to develop better and less expensive methods to prepare products of technical importance.

Writing a textbook of any level is always a challenging mission. This book has been designed in view of the growing importance of intermediates in the synthesis of natural and/or non-natural molecules. The ideas of functionality and stereochemistry have their origins in the second half of the nineteenth century, and the concepts of bonding and reaction mechanism undoubtedly belong to the twentieth century. The goal of this text is to incorporate basic conceptual tools and recent advances in the area of organic synthesis and particularly in the field of reactive intermediates, which are the key steps of any transformation. A systematic understanding of the mechanisms of organic reactions is necessary as without it organic chemistry is chaos, and impossible to learn.

Theory, mechanism, synthesis, structure, and stereochemistry are discussed throughout the book in a qualitative to semiquantitative fashion. During the writing of this book I have always tried to anticipate the questions of a student and to challenge them to think about the subject, motivating them to understand and to realize why, rather than just memorizing material. Chemists present chemistry in terms of structural diagrams and for this reason all reactions have been drawn using curly arrows; the handwriting of chemistry. Curved arrows and chemical reactions introduce students to the notational systems employed in all of the mechanistic discussions in the text. Such a course is frequently offered as a course material in organic chemistry at the undergraduate and beginning graduate level. I guess one will enjoy many fruitful hours of insight in the course of studying this book and I welcome your constructive comments on its content and approach. In attempting to accomplish these objectives, my approach is substantially different from currently available titles.

I have tried to put equal weight to the three basic fundamental aspects of the study of reactive intermediates, that is, reactions, mechanisms, and stereochemistry. The organization is based on these concepts, so that students can understand the large number of organic reactions based on relatively few principles. Accordingly, this book is divided into seven chapters. The first gives a brief introduction dealing with some basic, very frequently used terms, concepts of steric and electronic effects, and sites of chemical reactivity. The student is also told why such information will be important in the study of a particular reaction mechanism. Chapters 2–6 cover specific reactive intermediates in detail regarding their structure, geometry, generation, stability, and reactions. Chapter 7 gives a brief survey of the miscellaneous intermediates. End-of-chapter summaries review the major concepts of the chapter in a concise narrative format to help readers to understand the key points. The problems at the end of each chapter represent the application of concepts, rather than a review of material explicitly presented in the text. They are designed so that students can test themselves on the material just covered before they go on to the next section. I hope the level of difficulty will present a considerable challenge to students. These problems allow students to practice and test their mastery of core principles within each chapter. A concerted effort was made to make none of the problems so difficult that the student loses confidence.

I would greatly appreciate comments and suggestions from users that will improve the text or correct errors. I can only conclude by expressing my wish that others will enjoy using this text as much as I have enjoyed writing it. In particular, I want to thank the many wonderful and talented students I have had over the years, who taught me how to be a teacher and researcher. I also want to thank the dedicated people at Wiley-VCH, Germany, Dr. Anne Brennf¨uhrer (Commissioning Editor), Lesley Belfit (Project Editor), and Claudia Nussbeck (Editorial Assistant), for their truly superior editorial ability and for keeping me happy and on track.

Finally, I am grateful to my wife Meera and my son Keshav whose contributions to the project are beyond measure, and so I thank them for their understanding, love, encouragement, and assistance during the lengthy process of writing this book.


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