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

1 Introduction 1

1.1 Definition of Arrow Pushing 1

1.2 Functional Groups 5

1.3 Nucleophiles and Leaving Groups 8

1.4 Summary 8

Problems 10

2 Acids 19

2.1 What are Acids? 19

2.2 What is Resonance? 20

2.3 How is Acidity Measured? 23

2.4 Relative Acidities 25

2.5 Inductive Effects 29

2.6 Inductive Effects and Relative Acidities 31

2.7 Relative Acidities of Hydrocarbons 33

2.8 Summary 34

Problems 35

3 Bases and Nucleophiles 45

3.1 What are Bases? 45

3.2 What are Nucleophiles? 50

3.3 Leaving Groups 54

3.4 Summary 55

Problems 56

4 S[subscript N]2 Substitution Reactions 65

4.1 What is an S[subscript N]2 Reaction? 65

4.2 What are Leaving Groups? 67

4.3 Where Can S[subscript N]2 Reactions Occur? 68

4.4 S[subscript N]2' Reactions 71

4.5 Summary 73

Problems 74

5 S[subscript N]1 Substitution Reactions 83

5.1 What is an S[subscript N]1 Reaction? 83

5.2 How are S[subscript N]1 Reactions Initiated 84

5.3 The Carbocation 86

5.4 Carbocation Rearrangements 92

5.5 Summary 96

Problems 97

6 Elimination Reactions 101

6.1 E1 Eliminations 101

6.2 E2 Eliminations 104

6.3 How Do Elimination Reactions Work? 105

6.4 Summary 108

Problems 109

7 Addition Reactions 115

7.1 Addition of Halogens to Double Bonds 115

7.2 Markovnikov's Rule 119

7.3 Additions to Carbonyls 119

7.4 Summary 125

Problems 126

8 Moving Forward 135

8.1 Functional Group Manipulations 135

8.2 Name Reactions 139

8.3 Reagents 143

8.4 Final Comments 144

Problems 146

Appendix 1 pKa Values of Protons Associated with Common Functional Groups 155

Appendix 2 Answers and Explanations to Problems 159

Appendix 3 Student Reaction Glossary 283

Index287

Periodic Table of the Elements 301