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

ISBN-10: 0470171103

ISBN-13: 9780470171103

Edition: 2008

Authors: Daniel E. Levy

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During the past fifty years, organic chemistry has grown into a very mature and well-disciplined science. As such, introductory organic chemistry courses have been obliged to present the subject in a highly concentrated format covering literally hundreds of name reactions. Consequently, the route taken by many authors of organic chemistry textbooks has been to present the subject by listing multitudes of similar name reactions as a device to illustrate the fundamental mechanisms and reaction types relevant to organic chemistry. Psychologically, this induces the student to believe that memorization of this multitude of chemical reactions is the key to success in organic chemistry. This book does not rely on specific name reactions as a device for teaching this subject. Instead, specific generic examples have been chosen in order to illustrate to the student how to recognize when a specific reaction type is relevant. In this respect, this book has been designed to aid the student in approaching the seemingly difficult subject of organic chemistry in a simple and straightforward manner. In addition to the text, problem sets have been designed for each chapter in order to emphasize the important aspects of each chapter, to reinforce the students current knowledge of chemistry, and to introduce the student to other aspects of organic chemistry discussed in the latter chapters in this book as well as aspects not discussed here but in the student's current organic chemistry class. As a whole, this book intended to be used as a study aid/supplement and not as a replacement for any beginning level organic chemistry textbook. In this context, many students may find organic chemistry much more approachable and exciting. The methods described in this book reduce general organic chemistry to reactions between acids and bases. The concepts of acids and bases are covered in great depth in introductory chemistry courses. These courses do not, however, present acids and bases in the context of organic molecules. Therefore, the first two chapters are designed to acclimate students to the concepts of organic acids and then organic bases. The next chapters use the acid/base concepts to explain the fundamental reaction mechanisms relevant to organic chemistry. This discussion begins with the first mechanistic type presented to sophmore organic chemistry students - Sn2 reactions. Discussions of Sn2 reactions evolve into a study of Sn1 reactions presented in the following chapter. The following chapters present treatments of the remainig reaction types from which all students should be able to derive predicted products from almost any hypothetical organic reaction.
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Book details

List price: $50.99
Copyright year: 2008
Publisher: John Wiley & Sons, Incorporated
Publication date: 8/11/2008
Binding: Paperback
Pages: 320
Size: 5.00" wide x 8.00" long x 0.50" tall
Weight: 1.496

About the Author
Definition of Arrow Pushing
Functional Groups
Nucleophiles and Leaving Groups
What are Acids?
What is Resonance?
How is Acidity Measured?
Relative Acidities
Inductive Effects
Inductive Effects and Relative Acidities
Relative Acidities of Hydrocarbons
Bases and Nucleophiles
What are Bases?
What are Nucleophiles?
Leaving Groups
S[subscript N]2 Substitution Reactions
What is an S[subscript N]2 Reaction?
What are Leaving Groups?
Where Can S[subscript N]2 Reactions Occur?
S[subscript N]2' Reactions
S[subscript N]1 Substitution Reactions
What is an S[subscript N]1 Reaction?
How are S[subscript N]1 Reactions Initiated
The Carbocation
Molecular Structure and Orbitals
Stability of Carbocations
Carbocation Rearrangements
1,2-Hydride Shifts
1,2-Alkyl Shifts
Preventing Side Reactions
Elimination Reactions
E1 Eliminations
E2 Eliminations
How Do Elimination Reactions Work?
Addition Reactions
Addition of Halogens to Double Bonds
Markovnikov's Rule
Additions to Carbonyls
Addition-Elimination Reactions
Moving Forward
Functional Group Manipulations
Name Reactions
Final Comments
pK[subscript a] Values of Protons Associated with Common Functional Groups
Answers and Explanations to Problems
Student Reaction Glossary
Periodic Table of the Elements
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