- Paperback: 320 pages
- Publisher: Wiley-Interscience; 1 edition (August 11, 2008)
- Language: English
- ISBN-10: 0470171103
- ISBN-13: 978-0470171103
- Product Dimensions: 7.1 x 0.7 x 10 inches
- Shipping Weight: 1.3 pounds
- Average Customer Review: 15 customer reviews
- Amazon Best Sellers Rank: #1,336,683 in Books (See Top 100 in Books)
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Arrow-Pushing in Organic Chemistry: An Easy Approach to Understanding Reaction Mechanisms 1st Edition
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"Arrow Pushing in Organic Chemistry is not meant to replace a traditional textbook, a point that Levy makes clear in the preface. Rather, the text serves as a valuable workbook to counteract student memorization and compartmentalization of organic chemistry material. Review topics are presented in the context of new information, and major concepts are constantly reiterated and highlighted. Levy's book is a great supplemental resource to guide the novice organic chemistry student down the path to a true understanding of the subject." (Chemical Education Today, June 2010)
"The discussion of each class or reaction is both readable and informative and normally includes comparison of relative rates of similar reactions to demonstrate concepts such as nucleophilicity or steric hindrance. The major strength of the book involved the inclusion of problems at the end of each chapter. These are coupled with a set of very well discussed answers provided in the appendix. The problems fit well with the topic under discussion at each stage and the mechanistic answers and associated explanations are of a high quality. . . this text will make a useful addition to a university library or the supplementary reading list of a first year organic chemistry course." (Reviews, 1 December 2009)
"Does serve as a good support text for a more comprehensive organic text book. The high point of the book is the provision of a large number of carefully targeted problems at the end of each chapter, complete with well explained worked answers. I am sure that these will be highly useful to students who wish to practice the use of the ‘curry arrow." (Physical Sciences Centre Reviews, 1 December 2009)
"The most valuable materials in the book are the many solved problems." (Journal of Medicinal Chemistry, January 22, 2009)
"Arrow Pushing in Organic Chemistry fills an important gap in undergraduate education, and I would encourage every instructor of organic chemistry to seriously evaluate this text, as a substantive aid. This book is definitely well worth its price!" (Angewandte Chemie International Edition, January 12, 2009)
The first two semesters of organic chemistry are almost universally daunting to the student. The use of organic reaction mechanisms has greatly reduced the memorization, but most organic books skimp a bit on explaining how to write a clear reaction mechanism in order to limit their already gargantuan size (and cost). Along comes Arrow Pushing in Organic Chemistry by Levy (director of synthetic chemistry, Intradigm Corp.), a book that tries to clearly and succinctly explain writing organic mechanisms to these students. It does an excellent job in this. The work includes a large number of challenging end-of-chapter problems, with complete answers in the appendix (this appendix accounts for nearly half of the book). These problems may be too challenging for the typical sophomore organic student who may rely too much on the complete answers. This monograph is an excellent supplement but not a replacement for sophomore-level organic chemistry course resources. Most other monographs on organic reaction mechanisms are geared for the advanced undergraduate or graduate student. Summing Up: Recommended. Lower-division undergraduate organic chemistry students. (J.H. Glans, Sacred Heart University, Choice, February 2009)
From the Back Cover
A formula for success in organic chemistry
Look at any typical organic chemistry book and you'll probably be intimidated by its sheer size, the encyclopedic presentation of reactions, and the huge amount of material to memorize. As this book explains, there is a better and easier way to approach the subject—the arrow pushing strategy that reduces organic chemistry to the study of interactions between organic acids and bases and builds from there. This approach helps you develop deductive or predictive insight into the progression of starting materials to products and by what mechanisms the transformations occurred. A valuable companion to any introductory organic chemistry textbook, Arrow Pushing in Organic Chemistry:
- Defines the concept of arrow pushing in context with various reaction types, functional groups, mechanism types, reagents/nucleophiles, and leaving groups
Explains the concepts of organic acids and organic bases, and then uses them to explain fundamental reaction mechanisms, beginning with SN2 reactions and progressing to SN1 reactions and other reaction types
Emphasizes electron flow from atom to atom
Includes a summary and problem sets with each chapter to help you solidify learning
Using this approach, you should be able to derive predicted products from almost any hypothetical organic reaction. Instead of relying on rote memorization, you develop an in-depth understanding of, and an almost intuitive insight into, reactions.
This excellent companion text makes organic chemistry more approachable and exciting for students. It's also ideal for professionals who want to refresh their knowledge or for scientists from other disciplines, such as inorganic and physical chemists, biochemists, biologists, and pharmaceutical scientists who are new to the field.
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The book provides a very good foundation of such critical topics as resonance and acid strength. The discussion of bases and nucleophiles also touches on relative reactivity and solvent effects. The substitution chapters include Sn2, Sn2' and Sn1, including carbocation rearrangements. I felt the approach taken on the Eliminations and Additions reactions was not aligned with most sophomore-level textbooks, which could prove to be difficult for some students. Still, the arrow-pushing exercises in these chapters would provide excellent practice for students.
Approximately half of the book is dedicated to the presentation of detailed solutions to the end-of-chapter problems. The thorough explanations provided for each solution are often missing in traditional textbooks, leaving students wondering what went wrong when their answer doesn't "match" the solution manual. The very first problem in the first chapter is an arrow-pushing exercise covering 14 reactions of all types. For students who have just begun studying organic chemistry, the only part of the solution they need to worry about are the arrows drawn, but for more advanced students a useful description is provided to explain the reaction shown. No opportunity is missed to give students at all levels a more in-depth understanding of the lessons being learned and the problems being solved. This study guide is NOT a simple rehashing of material found in the full, traditional textbook, nor is it a dumbed-down version. It will most definitely push the reader with challenging and thought-provoking problems, while providing the skills needed to thrive in the study of organic chemistry.
I found the book to be well written with very few typos. The author separated the subject matter in well defined chapters that are arranged in a logical order. Each chapter is illustrated with examples, tables and figures presenting the basic concepts of arrow pushing with all the appropriate explanations. More importantly, each chapter comes with a series of exercises. The author went to great length to provide explanations to all exercises in the second part of the book. This is much more useful than just the answers.
Following an introductory chapter where definitions are provided, a brief discussion on polarization and charges brings the reader to chapter two. This chapter is interesting and very important. It serves as foundations for the remaining of the book. Many key concepts and information are given that will be needed throughout chapters 3-7. Chapter 3 is a natural continuation from the second chapter as the discussion is centered on bases and nucleophiles, including hardness/softness concept. Chapters 4 and 5 introduce substitution reactions (SN2 and SN1), tying in stereogenic implications for both types of substitution. In chapter 5, the author explains solvolysis, carbocations and their stabilities, orbital hybridization, 1,2-hydride and 1,2-alkyl shifts. This leads naturally to the next topic covered in chapter 6. This chapter touches on elimination processes, both unimolecular (E1) and bimolecular (E2).
Chapter 7 discusses addition reactions and introduces the Markovnikov rule. The author finishes this chapter with the first combination of the simple chemical processes (addition-elimination reactions). Chapter 8 prepares the reader to more complex reactions, still using the basic principles of arrow pushing.
There is a very good appendix on pKa values. The second appendix presents all the answers to the exercises found at the end of each chapter. This has tremendous value for any organic chemistry student. Because of the structure of the book, the subject is presented naturally. It flows easily and one builds upon what is presented in the earlier chapters. I would highly recommend this book to any college level student to gain a deep understanding of organic reaction mechanisms.
Jean-Marc Lapierre, Ph.D.
Associate Director, Chemistry
19 Presidential Way
Woburn, MA 01801