Organic Chemistry, 11th Edition
“It’s Organic Chemistry!”
That’s what we want students to exclaim after they become acquainted with our subject. Our lives revolve around organic chemistry, whether we all realize it or not. When we understand organic chemistry, we see how life itself would be impossible without it, how the quality of our lives depends upon it, and how examples of organic chemistry leap out at us from every direction. That’s why we can envision students enthusiastically exclaiming “It’s organic chemistry!” when, perhaps, they explain to a friend or family member how one central theme—organic chemistry— pervades our existence. We want to help students experience the excitement of seeing the world through an organic lens, and how the unifying and simplifying nature of organic chemistry helps make many things in nature comprehensible.
Our book makes it possible for students to learn organic chemistry well and to see the marvelous ways that organic chemistry touches our lives on a daily basis. Our book helps students develop their skills in critical thinking, problem solving, and analysis—skills that are so important in today’s world, no matter what career paths they choose. The richness of organic chemistry lends itself to solutions for our time, from the fields of health care, to energy, sustainability, and the environment. After all, it’s organic chemistry!
Guided by these goals, and by wanting to make our book even more accessible to students than it has ever been before, we have brought many changes to this edition.
New To This Edition
With this edition we bring Scott Snyder on board as a co-author. We’re very excited to have Scott join our team. Scott brings a rich resource of new perspectives to the book, particularly in the arena of complex molecule synthesis. Scott has infused new examples and applications of exciting chemistry that help achieve our goals. In addition to adding his perspectives to the presentation of core chemistry throughout the book, Scott’s work is manifest in most of this edition’s chapter openers and in all of the chapter closers, couched in a new feature called “Why do these topics matter?”.
“Why do these topics matter?” is a new feature that bookends each chapter with a teaser in the opener and a captivating example of organic chemistry in the closer. The chapter opener seeks to whet the student’s appetite both for the core chemistry in that chapter as well as a prize that comes at the end of the chapter in the form of a “Why do these topics matter?” vignette. These new closers consist of fascinating nuggets of organic chemistry that stem from research relating to medical, environmental, and other aspects of organic chemistry in the world around us, as well as the history of the science. They show the rich relevance of what students have learned to applications that have direct bearing on our lives and wellbeing. For example, in Chapter 6, the opener talks about the some of the benefits and drawbacks of making substitutions in a recipe, and then compares such changes to the nucleophilic displacement reactions that similarly allow chemists to change molecules and their properties. The closer then shows how exactly such reactivity has enabled scientists to convert simple table sugar into the artificial sweetener Splenda which is 600 times as sweet, but has no calories!
Laying the foundation earlier Certain tools are absolutely key to success in organic chemistry. Among them is the ability to draw structural formulas quickly and correctly. In this edition, we help students learn these skills even sooner than ever before by moving coverage of structural formulas and the use curved arrows earlier in the text (Section 3.2). We have woven together instruction about Lewis structures, covalent bonds, and dash structural formulas, so that students build their skills in these areas as a coherent unit, using organic examples that include alkanes, alkenes, alkynes, and alkyl halides. One could say that it’s a “use organic to teach organic” approach.
Getting to the heart of the matter quicker Acid-base chemistry, and electrophiles and nucleophiles are at the heart of organic chemistry. Students cannot master the subject if they do not have a firm and early grasp of these topics. In this edition, we cut to the chase with these topics earlier in Chapter 3 than ever before, providing a streamlined and highly efficient route to student mastery of these critical concepts.
Improving a core area: substitution reactions All organic instructors know how important it is for their students to have a solid understanding of substitution reactions. This is one reason our text has proven its lasting value. In this edition we have even further enhanced the presentation of substitution reactions in several ways, including a revised introduction of SN1 reactions (Section 6.10) through the classic hydrolysis experiments of Hughes, and a newly organized presentation of solvent effects on the rate of substitution reactions.
Striking a strong balance of synthetic methods Students need to learn methods of organic synthesis that are useful, as environmentally friendly as possible, and that are placed in the best overall contextual framework. In this edition we incorporate the Swern oxidation (Section 12.4), long held as a useful oxidation method and one that provides a less toxic alternative to chromate oxidations in some cases. We also restore coverage of the Wolff-Kishner reduction (Section 16.8C) and the Baeyer Villiger oxidation (Section 16.12), two methods whose importance has been proven by the test of time. The chemistry of radical reactions has also been refocused and streamlined by reducing thermochemistry content and by centralizing the coverage of allylic and benzylic radical substitutions (including NBS reactions) in one chapter (Sections 10.8 and 10.9), instead of distributing it between two, as before. The addition of sulfuric acid to alkenes and the Kolbe reaction have been deleted from the text, since these have little practical use in the laboratory. Toward the inclusion
of modern, though mechanistically complex, methods of organic synthesis, we introduce catalytic oxidation methods (e.g., Sharpless and others) in special boxes, and provide coverage of transition metal organometallic reactions (Heck, Suzuki, and others) in Special Topic G.
Maintaining an eye for clarity With every edition we improve the presentation of topics, reactions, and diagrams where the opportunity arises. In this edition some examples include improved discussion and diagrams regarding endo and exo Diels-Alder transition states, the effect of diene stereochemistry in Diels-Alder reactions (Section 13.10B), and improved mechanism depictions for aromatic sulfonation and thionyl chloride substitution.
Resonating with topics in spectroscopy The authors have incorporated new figures to depict shielding and deshielding of alkenyl and alkynyl hydrogens by magnetic anisotropy, and clarified the discussion of shielding and deshielding in NMR chemical shifts (no longer invoking the terms upfield and downfield). The discussion of chlorine and bromine isotopic signatures in mass spectra has been enhanced, and presentation of mass spectrometer designs has been refocused.
Showing how things work A mechanistic understanding of organic chemistry is key to student success in organic chemistry. Mechanisms have always been central to the book, and in this edition the authors have added a mechanistic framework for the Swern and chromate alcohol oxidations (Section 12.4) by presenting elimination of the carbinol hydrogen and a leaving group from oxygen as the common theme.
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