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Mechanisms in Organic Reactions

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The wonderful complexity of organic chemistry involves thousands of different reactions which allow the synthesis and interconversions of millions of compounds, some of great complexity. The key to understanding this vital branch of chemistry is the concept of the reaction mechanism.

This book starts with a discussion of how covalent bonds break and form, and how these bond-breaking and bond-forming processes provide the basis of reaction mechanisms. The principles governing how to make sensible suggestions about possible mechanisms are set out, and the distinction is made between elementary reactions, which involve just one step, and stepwise reactions which have more than one step and involve the production of intermediates that react further.

Chapter 2 covers kinetics, which provides useful information about reaction mechanisms, and allows us to distinguish between possible mechanisms in many cases. Elementary reactions do not involve intermediates, but go through a transition state. Although this transition state cannot be isolated, it can be studied in various ways which provide insights into the reaction mechanism, and this forms the subject matter of Chapter 3. This is followed by three chapters on the most important intermediates in organic chemistry: anions, radicals and cations. A final chapter on molecular reactions concerns thermal and photochemical processes. The concepts of frontier orbitals and the aromatic transition state allow us to predict which reactions are “allowed” and which are “forbidden”, and provide insights into why most reactions of practical interest involve multi-step processes.

Where common names are used for organic compounds, the systematic name is given as well at the first mention. Common names are widely used in the chemical literature, in industry and commerce, and there is a great divergence in the use of systematic as opposed to non-systematic nomenclature in the English-speaking world.

I thank many colleagues for helpful comments and advice, particularly Mr Martyn Berry and Professor Alwyn Davies FRS who have read the entire manuscript and whose suggestions for changes have improved the text in numerous places. I would also like to thank my wife Pat for her support and forbearance over the past three years. Enjoy the book!
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