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

ISBN: 978-0-470-17110-3
320 pages
August 2008
Arrow-Pushing in Organic Chemistry: An Easy Approach to Understanding Reaction Mechanisms (0470171103) cover image
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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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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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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  • 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

 

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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)

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