Organic Chemistry with Biological Applications 3rd Edition

Book Preface

I’ve taught organic chemistry many times for many years. Like most faculty, I began by trying to show 19-year-old students the logic and beauty of the subject, thinking that they would find it as fascinating as I did. It didn’t take long, though, before I realized what a disconnect there was between my own interests and expectations and those of my students. Some students did develop a real appreciation for the subject, but most seemed to worry primarily about getting into medical school. And why not? If a student has a clear career goal, why shouldn’t that person focus his or her efforts toward meeting that goal?

All of us who teach organic chemistry know that the large majority of our students—90% or more, and including many chemistry majors—are interested primarily in medicine, biology, and other life sciences rather than in pure chemistry. But if we are primarily teaching future physicians, biologists, biochemists, and others in the life sciences (not to mention the occasional lawyer, politician, or business person), why do we continue to teach the way we do? Why do our textbooks and lectures spend so much time discussing details of topics that interest professional chemists but have no connection to biology? Wouldn’t the limited amount of time we have be better spent paying more attention to the organic chemistry of living organisms and less to the organic chemistry of the research laboratory? Wouldn’t it better serve our students if we helped them reach their goals rather than reach goals we set for them? I believe so, and I have written this book, Organic Chemistry with Biological Applications, third edition, to encourage others who might also be thinking that the time has come to do things a bit differently.

This is, first and foremost, a textbook on organic chemistry. Look through it and you’ll find that almost all the standard topics are here, although the treatment of some has been attenuated to save space. Nevertheless, my guiding principle in writing this text has been to put a greater emphasis on those organic reactions and topics that are relevant to biological chemistry than on those that are not.

Organic chemistry, which began historically as the chemistry of living organisms, is now shifting back in that direction, judging from the increasing amount of biologically oriented research done in many chemistry departments and from the renaming of many departments to include chemical biology. Shouldn’t our teaching reflect that shift?

Organization of the text

Four distinct groups of chapters are apparent in this text. The first group (Chapters 1–6 and 10–11) covers the traditional principles of organic chemistry and spectroscopy that are essential for building further understanding.

The second group (Chapters 7–9 and 12–18) covers the common organic reactions found in all texts. As each laboratory reaction is discussed, however, a biological example is also shown to make the material more interesting and meaningful to students. For instance, trans fatty acids are described at the same time that catalytic hydrogenation is discussed (Section 8-5); biological methylations with S-adenosylmethionine are covered with SN2 reactions (Section 12-11); and biological reductions with NADH are introduced along with laboratory NaBH4 reductions (Section 13-3).

The third group of chapters (19–24) is unique to this text in its depth of coverage. These chapters deal exclusively with the main classes of biomolecules— amino acids and proteins, carbohydrates, lipids, and nucleic acids— and show how thoroughly organic chemistry permeates biological chemistry. Following an introduction to each class, major metabolic pathways for that class are discussed from the perspective of mechanistic organic chemistry. And finally, for those faculty who want additional coverage of natural products, polymers, and pericyclic reactions, the book ends with a fourth group of chapters (25–27) devoted to those topics. This final group is available in both electronic and hard-copy formats at the request of the adopter.