Arrow-Pushing in Organic Chemistry
An Easy Approach to Understanding Reaction Mechanisms
2. Edition May 2017
424 Pages, Softcover
Wiley & Sons Ltd
Organic chemistry is required coursework for degrees in life, food, and medical sciences. To help the students discouraged by the belief that this topic cannot be mastered without significant memorization, Arrow Pushing in Organic Chemistry serves as a handy supplement for understanding the subject.
* Includes new chapters, an expanded index, and additional problem sets complete with detailed solutions
* Focuses on understanding the mechanics and logic of organic reaction mechanisms
* Introduces ionic and non-ionic reactive species and reaction mechanisms
* Teaches strategies to predict reactive species, sites of reactions, and reaction products
* Provides a solid foundation upon which organic chemistry students can advance with confidence
Preface
Acknowledgements
Periodic Table of the Elements
Chapter1: Introduction
1.1 Definition of Arrow Pushing
1.2 Functional Groups
1.3 Nucleophiles and Leaving Groups
1.4 Summary
1.5 Problems
Chapter 2: Free Radicals
2.1 What are Free Radicals?
2.2 How are Free Radicals Formed?
2.3 Free Radical Stability
2.4 What Types of Reactions Involve Free Radicals?
2.5 Summary
2.6 Problems
Chapter 3: Acids
3.1 What are acids?
3.2 What is resonance?
3.3 How is acidity measured?
3.4 Relative acidities
3.5 Inductive Effects
3.6 Inductive Effects and Relative Acidities
3.7 Relative acidities of hydrocarbons
3.8 Summary
3.9 Problems
Chapter 4: Bases and Nucleophiles
4.1 What are bases?
4.2 What are nucleophiles?
4.3 Leaving Groups
4.4 Summary
4.5 Problems
Chapter 5: SN2 Substitution Reactions
5.1 What is an SN2 reaction?
5.2 What are leaving groups?
5.3 Where can SN2 reactions occur?
5.4 SN2' reactions
5.5 Summary
5.6 Problems
Chapter 6: SN1 Substitution Reactions
6.1 What is an SN1 reaction?
6.2 How are SN1 reactions initiated?
6.3 The carbocation
6.4 Carbocation rearrangements
6.5 Summary
6.6 Problems
Chapter 7: Elimination Reactions
7.1 E1 Eliminations
7.2 E1cb Eliminations
7.3 E2 Eliminations
7.4 How do elimination reactions work?
7.5 E1cb Eliminations vs. E2 Eliminations
7.6 Summary
7.7 Problems
Chapter 8: Addition Reactions
8.1 Addition of Halogens to Double Bonds
8.2 Markovnikov's Rule
8.3 Additions to carbonyls
8.4 Summary
8.5 Problems
Chapter 9: Carbenes
9.1 What are carbenes?
9.2 How are carbenes formed?
9.3 Reactions with carbenes
9.4 Carbenes vs. Carbenoids
9.5 Summary
9.6 Problems
Chapter 10: Pericyclic Reactions
10.1 What are pericyclic reactions?
10.2 Electrocyclic Reactions
10.3 Cycloaddition Reactions
10.4 Sigmatropic Rearrangements
10.5 Summary
10.6 Problems
Chapter 11: Moving Forward
11.1 Functional Group Manipulations
11.2 Name Reactions
11.3 Reagents
11.4 Final Comments
11.5 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
Chapter 9 Solutions
Chapter 10 Solutions
Chapter 11 Solutions
Appendix 3 - Student Reaction Glossary
Index