Arrow-Pushing in Organic Chemistry: An Easy Approach to Understanding Reaction Mechanisms / Edition 1

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Overview

Find an easier way to learn organic chemistry with Arrow-Pushing in Organic Chemistry: An Easy Approach to Understanding Reaction Mechanisms, a book that uses the arrow-pushing strategy to reduce this notoriously challenging topic to the study of interactions between organic acids and bases. Understand the fundamental reaction mechanisms relevant to organic chemistry, beginning with Sn2 reactions and progressing to Sn1 reactions and other reaction types. The problem sets in this book, an excellent supplemental text, emphasize the important aspects of each chapter and will reinforce the key ideas without requiring memorization.

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Editorial Reviews

From the Publisher
"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)

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Product Details

  • ISBN-13: 9780470171103
  • Publisher: Wiley
  • Publication date: 8/18/2008
  • Edition description: New Edition
  • Edition number: 1
  • Pages: 320
  • Sales rank: 646,193
  • Product dimensions: 7.00 (w) x 9.90 (h) x 0.80 (d)

Meet the Author

DANIEL E. LEVY, PhD, is the Director of Synthetic Chemistry at Intradigm Corporation, pursuing delivery vehicles for siRNA therapeutics. He previously worked at Glycomed Inc., where he pursued the design and synthesis of novel glycomimetics for the treatment of cancer and inflammatory disorders; COR Therapeutics, where he pursued carbocyclic AMP analogs as inhibitors of type V adenylyl cyclase; and at Scios, Inc., where he pursued novel kinase inhibitors. Dr. Levy coauthored a book entitled The Chemistry of C-Glycosides and later collaborated with Dr. Péter Fügedi in the development and presentation of short courses entitled "Modern Synthetic Carbohydrate Chemistry" and "The Organic Chemistry of Sugars" offered by the American Chemical Society Continuing Education Department. Most recently, Dr. Levy coedited with Dr. Fügedi the book The Organic Chemistry of Sugars, based on the short course of the same name. Dr. Levy received his BS in chemistry from the University of California, Berkeley, and his PhD in organic chemistry from the Massachusetts Institute of Technology.

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Table of Contents

Preface.

Acknowledgments.

About the Author.

Chapter 1 Introduction.

1.1 Definition of Arrow Pushing.

1.2 Functional Groups.

1.3 Nucleophiles and Leaving Groups.

1.4 Summary.

Problems.

Chapter 2 Acids.

2.1 What are Acids?

2.2 What is Resonance?

2.3 How is Acidity Measured?

2.4 Relative Acidities.

2.5 Inductive Effects.

2.6 Inductive Effects and Relative Acidities.

2.7 Relative Acidities of Hydrocarbons.

2.8 Summary.

Problems.

Chapter 3 - Bases and Nucleophiles.

3.1 What are bases?

3.2 What are nucleophiles?

3.3 Leaving Groups.

3.4 Summary.

Problems.

Chapter 4 - SN2 Substitution Reactions.

4.1 What is an SN2 Reaction?

4.2 What are Leaving Groups?

4.3 Where can SN2 Reactions Occur?

4.4 SN2' Reactions.

4.5 Summary.

Problems.

Chapter 5  SN1 Substitution Reactions.

5.1 What is an SN1 Reaction?

5.2 How are SN1 Reactions Initiated?

5.3 The Carbocation.

5.4 Carbocation Rearrangements.

5.5 Summary.

Problems.

Chapter 6. Elimination Reactions.

6.1 E1 Eliminations.

6.2 E2 Eliminations.

6.3 How do Elimination Reactions Work?

6.4 Summary.

Problems.

Chapter 7 - Addition Reactions.

7.1 Addition of Halogens to Double Bonds.

7.2 Markovnikov's Rule.

7.3 Additions to Carbonyls.

7.4 Summary.

Problems.

Chapter 8-Moving Forward

8.1 Functional Group Manipulations.

8.2 Name Reactions.

8.3 Reagents.

8.4 Final Comments.

Problems.

Appendix 1-pKa Values of Protons Associated with Common Functional Groups.

Appendix 2-Answers and Explanations to Problems.

Chapter 1 Solutions.

Chapter 2 Solutions.

Chapter 3 Solutions.

Chapter 4 Solutions.

Chapter 5 Solutions.

Chapter 6 Solutions.

Chapter 7 Solutions.

Chapter 8 Solutions.

Appendix 3-Student Reaction Glossary.

Index.

Periodic Table of the Elements.

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Sort by: Showing all of 4 Customer Reviews
  • Posted June 12, 2011

    No more memorizing reactions

    Dr. Daniel E. Levy's book, Arrow Pushing in Organic Chemistry, gets an A+ in any grading system. I am an organic chemist with 30 years of bench experience and I can say without reservation that this book is superb. I wish that it had been around when I was an organic chemistry student. The subtitle of the book says it all, "An Easy Approach to Understanding Reaction Mechanisms." Dr. Levy really delivers on his commitment to students that with the tools presented in this book they will be able to predict and explain all reaction mechanisms. His promise: "Students do not have to memorize endless numbers of reactions." You will have power over the concepts, and your classmates will think you are amazing. There are three primary sections: discussion, problems and illustrated solutions. The solutions portion comprises half of the book. This text is a lucid, concise explanation of mechanisms, problems and detailed solutions. Every reaction mechanism will become clear. A complication that often trips up the student is seeing other functional groups on the starting molecule. This book offers many variations so that when additional functional groups appear, they will be no problem. Any person who values his or her time will appreciate the effort by the author to provide truly serviceable indices, table of contents, and appendices. The failing of many academic texts is in these areas. If a text or reference book has a poor index, it is mainly useful as a paperweight. The table of contents in this text is also clear, well defined and organized. This book makes it easy to find any reaction and cross-reference the material for ease of use. Additionally, the appendices are thorough and exhaustive. Appendix 1 lists pKa values of protons on common functional groups. Appendix 2 contains all the answers and explanations. Appendix 3 has a form that demonstrates how to organize your thinking about reactions. All of these are very valuable. This text will continue to be a good reference and refresher later on. I highly recommend adding it to your reference library.

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  • Posted September 13, 2010

    A must read for college level chemistry students

    Reading this book brought me back to the time when I started to learn organic chemistry. After one year studying chemistry at the University of Montreal, I managed to find a summer internship position in one of the research labs. Aside from generating a much needed money influx, this was the most incredible opportunity for an undergraduate chemistry student. For 16 weeks, I had a handful of graduate students teaching me the ins and outs of organic chemistry, including mechanistic details and arrow pushing. The book "Arrow pushing in organic chemistry" by Daniel Levy is as close to this as it could be with a book. It demystifies organic chemical reactions because it does not concentrate on the name, the product or the overall transformation but on how it works and why it works that way.

    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
    ArQule Inc.
    19 Presidential Way
    Woburn, MA 01801

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  • Posted January 31, 2010

    A must-have in organic chemistry

    A remarkable book useful for college students, professionals who need the basics to communicate with organic chemists and also anyone else who needs to reconnect with organic mechanisms.

    It methodically encompasses all the important concepts of organic chemistry using curved-arrow notation to understand organic reaction mechanisms. All the fundamentals of organic chemistry are presented in a very creative and interactive methodology with exercises and solutions.

    Indeed, this book was written by a well-rounded organic chemist who is also an expert in biopharmaceutical and medicinal chemistry. His impressive creativity and his passion in the field led him to come up with an original concept in presenting and communicating those fundamentals. Therefore, every single piece of information presented in this book is clearly detailed and accessible in a snapshot.

    "Arrow-Pushing in Organic Chemistry" is very handy and will capture your attention no matter what. This is a must-have on your bookshelf.

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  • Anonymous

    Posted October 8, 2008

    Great Supplement to Introductory Organic Chemistry Textbooks

    I highly recommend this book for college students taking organic chemistry classes. Through the use of arrow pushing and an introduction to the acid-base properties of organic molecules, students are guided to an understanding of how organic reactions work. In the first few chapters, an introduction to arrow pushing, organic acids, organic bases and the concept of nucleophiles are presented. These concepts are then used to describe how basic chemical reactions work. The chapters that follow cover the various important reaction subtypes introduced in organic chemistry textbooks. Intended as a supplemental text for introductory organic chemistry courses, this book helps readers to understand the key steps in organic reactions by dissecting them into the basic building blocks of interactions between acids and bases. Through this approach readers will no longer need to memorize reactions and will be able to deduce routes and understand how electrons move, bonds form and atoms shift. The book is easy to read and it is well written. Additionally, problem sets support and expand upon the concepts of each chapter. Given the encyclopedic nature of organic chemistry, the author did an excellent job of balancing text with examples and problem solving. This book is a must-have for all organic chemistry students.

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