Organic Chemistry, 2 edition

Book Preface

Students of chemistry are not hard-pressed to fi nd a text to support their learning in organic chemistry through their years at university. The shelves of a university bookshop will usually offer a choice of at least half a dozen—all entitled ‘Organic Chemistry’, all with substantially more than 1000 pages. Closer inspection of these titles quickly disappoints expectations of variety. Almost without exception, general organic chemistry texts have been written to accompany traditional American sophomore courses, with their rather precisely defined requirements. This has left the authors of these books little scope for reinvigorating their presentation of chemistry with new ideas.

We wanted to write a book whose structure grows from the development of ideas rather than being dictated by the sequential presentation of facts. We believe that students benefit most of all from a book which leads from familiar concepts to unfamiliar ones, not just encouraging them to know but to understand and to understand why. We were spurred on by the nature of the best modern university chemistry courses, which themselves follow this pattern: this is after all how science itself develops. We also knew that if we did this we could, from the start, relate the chemistry we were talking about to the two most important sorts of chemistry that exist—the chemistry that is known as life, and the chemistry as practised by chemists solving real problems in laboratories.

We aimed at an approach which would make sense to and appeal to today’s students. But all of this meant taking the axe to the roots of some long-standing textbook traditions. The best way to fi nd out how something works is to take it apart and put it back together again, so we started with the tools for expressing chemical ideas: structural diagrams and curly arrows. Organic chemistry is too huge a fi eld to learn even a small part by rote, but with these tools, students can soon make sense of chemistry which may be unfamiliar in detail by relating it to what they know and understand. By calling on curly arrows and ordering chemistry according to mechanism we allow ourselves to discuss mechanistically (and orbitally) simple reactions (addition to C=O, for example) before more complex and involved ones (such as SN1 and SN2). Complexity follows in its own time, but we have deliberately omitted detailed discussion of obscure reactions of little value, or of variants of reactions which lie a simple step of mechanistic logic from our main story: some of these are explored in the problems associated with each chapter, which are available online.1 We have similarly aimed to avoid exhuming principles and rules (from those of Le Châtelier through Markovnikov, Saytseff, least motion, and the like) to explain things which are better understood in terms of unifying fundamental thermodynamic or mechanistic concepts.