Organic Chemistry as a Second Language - David R. Klein

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Résumé :

Chapter 1 Bond-line Drawings 1

1.1 How to Read Bond-Line Drawings 1

1.2 How to Draw Bond-Line Drawings 4

1.3 Mistakes to Avoid 6

1.4 More Exercises 6

1.5 Identifying Formal Charges 8

1.6 Finding Lone Pairs that Are Not Drawn 11

End-of-Chapter Problems 15

Chapter 2 Resonance 19

2.1 What Is Resonance? 19

2.2 Curved Arrows: The Tools for Drawing Resonance Structures 20

2.3 The Two Commandments 21

2.4 Drawing Good Arrows 24

2.5 Formal Charges in Resonance Structures 26

2.6 Drawing Resonance Structures-Step By Step 29

2.7 Drawing Resonance Structures-By Recognizing Patterns 33

2.8 Assessing the Relative Importance of Resonance Structures 40

End-of-Chapter Problems 45

Chapter 3 Acid-base Reactions 48

3.1 Factor 1-What Atom Is the Charge On? 48

3.2 Factor 2-Resonance 51

3.3 Factor 3-Induction 54

3.4 Factor 4-Orbitals 56

3.5 Ranking the Four Factors 57

3.6 Other Factors 60

3.7 Quantitative Measurement (pKa Values) 61

3.8 Predicting the Position of Equilibrium 61

3.9 Showing a Mechanism 62

End-of-Chapter Problems 64

Chapter 4 Geometry 68

4.1 Orbitals and Hybridization States 68

4.2 Geometry 71

4.3 Lone Pairs 73

End-of-Chapter Problems 75

Chapter 5 Nomenclature 77

5.1 Functional Group 78

5.2 Unsaturation 79

5.3 Naming the Parent Chain 80

5.4 Naming Substituents 83

5.5 Stereoisomerism 85

5.6 Numbering 87

5.7 Common Names 91

5.8 Going from a Name to a Structure 92

End-of-Chapter Problems 92

Chapter 6 Conformations 95

6.1 How to Draw a Newman Projection 95

6.2 Ranking the Stability of Newman Projections 99

6.3 Drawing Chair Conformations 101

6.4 Placing Groups on the Chair 105

6.5 Ring Flipping 108

6.6 Comparing the stability of Chairs 114

6.7 Don't Be Confused by The Nomenclature 117

End-of-Chapter Problems 117

Chapter 7 Configurations 121

7.1 Locating Chiral Centers 121

7.2 Determining the Configuration of a Chiral Center 124

7.3 Nomenclature 131

7.4 Drawing Enantiomers 134

7.5 Diastereomers 138

7.6 MESO Compounds 139

7.7 Drawing Fischer Projections 141

7.8 Optical Activity 145

End-of-Chapter Problems 146

Chapter 8 Mechanisms 149

8.1 Introduction to Mechanisms 149

8.2 Nucleophiles and Electrophiles 149

8.3 Basicity vs. Nucleophilicity 151

8.4 Arrow-Pushing Patterns for Ionic Mechanisms 153

8.5 Carbocation Rearrangements 158

8.6 Information Contained in a Mechanism 162

End-of-Chapter Problems 164

Chapter 9 Substitution Reactions 168

9.1 The Mechanisms 168

9.2 Factor 1-The Electrophile (Substrate) 170

9.3 Factor 2-The Nucleophile 172

9.4 Factor 3-The Leaving Group 174

9.5 Factor 4-The Solvent 176

9.6 Using All Four Factors 177

9.7 Drawing a Substitution Product and the Mechanism of Its Formation 178

End-of-Chapter Problems 182

Chapter 10 Elimination Reactions 185

10.1 The E2 Mechanism 185

10.2 The Regiochemical Outcome of an E2 Reaction 186

10.3 The Stereochemical Outcome of an E2 Reaction 187

10.4 The E1 Mechanism 190

10.5 The Regiochemical Outcome of an E1 Reaction 192

10.6 The Stereochemical Outcome of an E1 Reaction 192

10.7 Substitution vs. Elimination 193

10.8 Determining the Function of the Reagent 193

10.9 Identifying the Mechanism(s) 195

10.10 P...

Biographie:

Organic chemistry can be a challenging subject. Most students view organic chemistry as a subject requiring hours upon hours of memorization. Author David Klein's Second Language books prove this is not true-organic chemistry is one continuous story that makes sense if you pay attention. Offering a unique skill-building approach, these market-leading books teach students how to ask the right questions to solve problems, study more efficiently to avoid wasting time, and learn to speak the language of organic chemistry.

Covering the initial half of the course, Organic Chemistry as a Second Language: First Semester Topics reviews critical principles and explains their relevance to the rest of the course. Each section provides hands-on exercises and step-by-step explanations to help students fully comprehend classroom lectures and textbook content. Now in the 6th edition, there are approximately 30 new end-of-chapter exercises in each chapter. These new exercises vary in difficulty, starting with exercises that focus on just one skill or concept (called Practice Problems), and continuing with exercises that focus on more than one skill or concept (called Integrated Problems), and concluding with advanced exercises (called Challenge Problems). There are also author-created, detailed solutions for all new exercises, and these detailed solutions appear in the back of the book.