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

by Levy, Daniel E.

• ISBN13: 9780470171103
• ISBN10: 0470171103
• Edition: 1st
• Format: Paperback
• Copyright: 2008-08-18
• Publisher: Wiley-Interscience

Summary

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.

Author Biography

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.

Table of Contents

Preface	p. xi
Acknowledgments	p. xiii
About the Author	p. xv
Introduction	p. 1
Definition of Arrow Pushing	p. 1
Functional Groups	p. 5
Nucleophiles and Leaving Groups	p. 8
Summary	p. 8
Problems	p. 10
Acids	p. 19
What are Acids?	p. 19
What is Resonance?	p. 20
How is Acidity Measured?	p. 23
Relative Acidities	p. 25
Inductive Effects	p. 29
Inductive Effects and Relative Acidities	p. 31
Relative Acidities of Hydrocarbons	p. 33
Summary	p. 34
Problems	p. 35
Bases and Nucleophiles	p. 45
What are Bases?	p. 45
What are Nucleophiles?	p. 50
Leaving Groups	p. 54
Summary	p. 55
Problems	p. 56
S[subscript N]2 Substitution Reactions	p. 65
What is an S[subscript N]2 Reaction?	p. 65
What are Leaving Groups?	p. 67
Where Can S[subscript N]2 Reactions Occur?	p. 68
S[subscript N]2' Reactions	p. 71
Summary	p. 73
Problems	p. 74
S[subscript N]1 Substitution Reactions	p. 83
What is an S[subscript N]1 Reaction?	p. 83
How are S[subscript N]1 Reactions Initiated	p. 84
The Carbocation	p. 86
Molecular Structure and Orbitals	p. 86
Stability of Carbocations	p. 90
Carbocation Rearrangements	p. 92
1,2-Hydride Shifts	p. 92
1,2-Alkyl Shifts	p. 93
Preventing Side Reactions	p. 95
Summary	p. 96
Problems	p. 97
Elimination Reactions	p. 101
E1 Eliminations	p. 101
E2 Eliminations	p. 104
How Do Elimination Reactions Work?	p. 105
Summary	p. 108
Problems	p. 109
Addition Reactions	p. 115
Addition of Halogens to Double Bonds	p. 115
Markovnikov's Rule	p. 117
Additions to Carbonyls	p. 119
1,2-Additions	p. 119
1,4-Additions	p. 121
Addition-Elimination Reactions	p. 123
Summary	p. 125
Problems	p. 126
Moving Forward	p. 135
Functional Group Manipulations	p. 135
Name Reactions	p. 139
Reagents	p. 143
Final Comments	p. 144
Problems	p. 146
pK[subscript a] Values of Protons Associated with Common Functional Groups	p. 155
Answers and Explanations to Problems	p. 159
Solutions	p. 159
Solutions	p. 173
Solutions	p. 191
Solutions	p. 205
Solutions	p. 223
Solutions	p. 233
Solutions	p. 243
Solutions	p. 261
Student Reaction Glossary	p. 283
Index	p. 287
Periodic Table of the Elements	p. 301
Table of Contents provided by Ingram. All Rights Reserved.