Organic Chemistry 5th Edition
My goal in writing Organic Chemistry was to create a text that showed students the beauty and logic of organic chemistry by giving them a book that they would use. This text is based on lecture notes and handouts that were developed in my own organic chemistry courses over my 30-year teaching career. I have followed two guiding principles: use relevant and interesting applications to illustrate chemical phenomena, and present the material in a student-friendly fashion using bulleted lists, solved problems, and extensive illustrations and summaries. Organic Chemistry is my attempt to simplify and clarify a course that intimidates many students—to make organic chemistry interesting, relevant, and accessible to all students, both chemistry majors and those interested in pursuing careers in biology, medicine, and other disciplines, without sacriﬁcing the rigor they need to be successful in the future.
The Basic Features
• Style This text is different—by design. Today’s students rely more heavily on visual imagery to learn than ever before. The text uses less prose and more diagrams, equations, tables, and bulleted summaries to introduce and reinforce the major concepts and themes of organic chemistry.
• Content Organic Chemistry accents basic themes in an effort to keep memorization at a minimum. Relevant examples from everyday life are used to illustrate concepts, and this material is integrated throughout the chapter rather than conﬁned to a boxed reading. Each topic is broken down into small chunks of information that are more manageable and easily learned. Sample problems are used as a tool to illustrate stepwise problem solving. Exceptions to the rule and older, less useful reactions are omitted to focus attention on the basic themes.
• Organization Organic Chemistry uses functional groups as the framework within which chemical reactions are discussed. Thus, the emphasis is placed on the reactions that different functional groups undergo, not on the reactions that prepare them. Moreover, similar reactions are grouped together, so that parallels can be emphasized. These include acid–base reactions (Chapter 2), oxidation and reduction (Chapters 12 and 20), radical reactions (Chapter 15), and reactions of organometallic reagents (Chapter 20).
By introducing one new concept at a time, keeping the basic themes in focus, and breaking complex problems down into small pieces, I have found that many students ﬁnd organic chemistry an intense but learnable subject. Many, in fact, end the year-long course surprised that they have actually enjoyed their organic chemistry experience.
Organization and Presentation
For the most part, the overall order of topics in the text is consistent with the way most instructors currently teach organic chemistry. There are, however, some important differences in the way topics are presented to make the material logical and more accessible. This can especially be seen in the following areas.
• Review material Chapter 1 presents a healthy dose of review material covering Lewis structures, molecular geometry and hybridization, bond polarity, and types of bonding. While many of these topics are covered in general chemistry courses, they are presented here from an organic chemist’s perspective. I have found that giving students a ﬁrm grasp of these fundamental concepts helps tremendously in their understanding of later material.
• Acids and bases Chapter 2 on acids and bases serves two purposes. It gives students experience with curved arrow notation using some familiar proton transfer reactions. It also illustrates how some fundamental concepts in organic structure affect a reaction, in this case an acid–base reaction. Since many mechanisms involve one or more acid–base reactions, I emphasize proton transfer reactions early and come back to this topic often throughout the text.
• Functional groups Chapter 3 uses the functional groups to introduce important properties of organic chemistry. Relevant examples—PCBs, vitamins, soap, and the cell membrane—illustrate fundamental solubility concepts. In this way, practical topics that are sometimes found in the last few chapters of an organic chemistry text (and thus often omitted because instructors run out of time) are introduced early, so that students can better grasp why they are studying the discipline.
• Stereochemistry Stereochemistry (the three-dimensional structure of molecules) is introduced early (Chapter 5) and reinforced often, so students have every opportunity to learn and understand a crucial concept in modern chemical research, drug design, and synthesis.
• Modern reactions While there is no shortage of new chemical reactions to present in an organic chemistry text, I have chosen to concentrate on new methods that introduce a particular three-dimensional arrangement in a molecule, so-called asymmetric or enantioselective reactions. Examples include Sharpless epoxidation (Chapter 12), CBS reduction (Chapter 20), and enantioselective synthesis of amino acids (Chapter 29).
• Grouping reactions Since certain types of reactions have their own unique characteristics and terminology that make them different from the basic organic reactions, I have grouped these reactions together in individual chapters. These include acid–base reactions (Chapter 2), oxidation and reduction (Chapters 12 and 20), radical reactions (Chapter 15), and reactions of organometal-lic reagents (Chapter 20). I have found that focusing on a group of reactions that share a common theme helps students to better see their similarities.
• Synthesis Synthesis, one of the most difﬁcult topics for a beginning organic student to master, is introduced in small doses, beginning in Chapter 7 and augmented with a detailed discussion of retrosynthetic analysis in Chapter 11. In later chapters, special attention is given to the retrosynthetic analysis of compounds prepared by carbon–carbon bond- forming reactions (for example, Sections 20.11 and 21.10C).
• Spectroscopy Since spectroscopy is such a powerful tool for structure determination, four methods are discussed over two chapters (Chapters 13 and 14).
• Key Concepts End-of-chapter summaries succinctly summarize the main concepts and themes of the chapter, making them ideal for review prior to working the end-of-chapter problems or taking an exam.
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