Organic Chemistry: With Biological Applications 2nd Edition
I’ve taught organic chemistry many times for many years, and it has often struck me what a disconnect there is between the interests and expectations of me—the teacher—and the interests and expectations of those being taught— my students. I love the logic and beauty of organic chemistry, and I want to pass that feeling on to others. My students, however, seem to worry primarily about getting into medical school. That may be an exaggeration, but there is also a lot of truth in it. All of us who teach organic chemistry know that the large majority of our students—90% or more, 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 and businessperson), why do we continue to teach the way we do? Why do we spend so much time discussing details of topics that interest research 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? I believe so, and I have written this book, Organic Chemistry with Biological Applications, to encourage others who might also be thinking that the time has come to try doing things a bit differently.
This is, first and foremost, a textbook on organic chemistry, and you will find that almost all of the standard topics are here. Nevertheless, my guiding principle in writing this text has been to emphasize organic reactions and topics that are relevant to biological chemistry
Organization of the Text
When looking through the text, three distinct groups of chapters are apparent. The first group (Chapters 1–6 and 10–11) covers the traditional principles of organic chemistry that are essential for building the background necessary to 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 to students. As an example, trans fatty acids are described at the same time that catalytic hydrogenation is discussed (see Section 8.5, page 261). The third group of chapters (19–25) is unique to this text in their 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. Finally, the book ends with a chapter devoted to natural products and their biosynthesis.
Content Changes in the Second Edition
Text content has been revised substantially for this second edition as a result of user feedback. Consequently, the text covers most of the standard topics found in typical organic courses yet still retains an emphasis on biological reactions and molecules. Perhaps the most noticeable change is that the book is now titled Organic Chemistry with Biological Applications to emphasize that it is, above all, written for the standard organic chemistry course found in colleges and universities everywhere.
Within the text itself, a particularly important change is that the chapter on chirality and stereochemistry at tetrahedral centers, a topic crucial to understanding biological chemistry, has been moved forward to Chapter 4 from its previous placement in Chapter 9. In addition, the chapter on organo-halides has been moved from Chapter 10 to Chapter 12, thereby placing spectroscopy earlier (Chapters 10 and 11).
Other Changes and Newly Added Content
Alkene ozonolysis and diol cleavage—added in Section 8.8
•Addition of carbenes to alkenes—added in Section 8.9
•The Diels–Alder cycloaddition reaction—added in Section 8.14
•Acetylide alkylations—added in Section 8.15
•Aromatic ions—added in Section 9.4
•Nucleophilic aromatic substitution—added in Section 9.9
•Aromatic hydrogenation—added in Section 9.10
•Allylic bromination of alkenes—added in Section 12.2
•Dess–Martin oxidation of alcohols—added in Section 13.5
•Protection of alcohols as silyl ethers—added in Section 13.6
•Claisen rearrangement—added in Section 13.10
•Protection of ketones and aldehydes as acetals—added in Section 14.8
•Conjugate addition of diorganocuprates to enones—added in Section 14.11
•Grignard reaction of nitriles—added in Section 15.7
•Reaction of diorganocuprates with acid halides—added in Section 16.4
•Alpha bromination of carboxylic acids—added in Section 17.3
•Amino acid metabolism—simplified coverage, Section 20.4
•Amino acid biosynthesis—simplified coverage, Section 20.5
•Final comments on metabolism—added in Section 23.10
•Nucleotide metabolism—simplified coverage, Section 24.9
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|October 27, 2019|
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