Organic Chemistry as a Second Language

David Klein is a lecturer at Johns Hopkins University where he teaches Organic and General Chemistry. He is a dynamic and creative teacher and uses analogy to help students grasp difficult topics. Klein's unique informal voice and manner of presentation help students truly master key topics in this course. He is also the author of Organic Chemistry as a Second Language; response to this book has been phenomenal.

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 Predicting the Products 197

End-of-Chapter Problems 200

Chapter 11 Addition Reactions 204

11.1 Terminology Describing Regiochemistry 204

11.2 Terminology Describing Stereochemistry 206

11.3 Adding H and H 212

11.4 Adding H and X, Markovnikov 215

11.5 Adding H and Br, Anti-Markovnikov 220

11.6 Adding H and OH, Markovnikov 224

11.7 Adding H and OH, Anti-Markovnikov 226

11.8 Synthesis Techniques 230

11.9 Adding Br and Br; Adding Br and OH 236

11.10 Adding OH and OH, Anti 241

11.11 Adding OH and OH, syn 243

11.12 Oxidative Cleavage of an Alkene 245

End-of-Chapter Problems 248

Chapter 12 Alkynes 253

12.1 Structure and Properties of Alkynes 253

12.2 Preparation of Alkynes 255

12.3 Alkylation of Terminal Alkynes 256

12.4 Reduction of Alkynes 258

12.5 Hydration of Alkynes 261

12.6 Keto-Enol Tautomerization 264

12.7 Ozonolysis of Alkynes 269

End-of-Chapter Problems 270

Chapter 13 Alcohols 274

13.1 Naming and Designating Alcohols 274

13.2 Predicting Solubility of Alcohols 275

13.3 Predicting Relative Acidity of Alcohols 276

13.4 Preparing Alcohols: A Review 279

13.5 Preparing Alcohols via Reduction 280

13.6 Preparing Alcohols via Grignard Reactions 286

13.7 Summary of Methods for Preparing Alcohols 289

13.8 Reactions of Alcohols: Substitution and Elimination 290

13.9 Reactions of Alcohols: Oxidation 294

13.10 Converting an Alcohol into an Ether 297

End-of-Chapter Problems 298

Chapter 14 Ethers and Epoxides 300

14.1 Introduction to Ethers 300

14.2 Preparation of Ethers 302

14.3 Reactions of Ethers 304

14.4 Preparation of Epoxides 305

14.5 Ring-Opening Reactions of Epoxides 307

End-of-Chapter Problems 313

Chapter 15 Synthesis 316

15.1 Functional Group Interconversion 316

15.2 Changing the Carbon Skeleton 317

15.3 Two Questions to Ask in Every Synthesis Problem 318

15.4 Retrosynthetic Analysis 320

15.5 Creating Your Own Problems 323

End-of-Chapter Problems 324

Detailed Solutions S- 1

Index I- 1