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More About This Title Organic Chemistry as a Second Language: First Semester Topics, 3E
English
Readers continue to turn to Klein’s Organic Chemistry as a Second Language: First Semester Topics, 3rd Edition because it enables them to better understand fundamental principles, solve problems, and focus on what they need to know to succeed. This edition explores the major principles in the field and explains why they are relevant. It is written in a way that clearly shows the patterns in organic chemistry so that readers can gain a deeper conceptual understanding of the material. Topics are presented clearly in an accessible writing style along with numerous of hands-on problem solving exercises.
English
1.1 How to Read Bond-Line Drawings 1
1.2 How to Draw Bond-Line Drawings 5
1.3 Mistakes to Avoid 7
1.4 More Exercises 7
1.5 Identifying Formal Charges 10
1.6 Finding Lone Pairs That Are Not Drawn 14
CHAPTER 2RESONANCE20
2.1 What Is Resonance? 20
2.2 Curved Arrows: The Tools for Drawing Resonance Structures 21
2.3 The Two Commandments 24
2.4 Drawing Good Arrows 27
2.5 Formal Charges in Resonance Structures 29
2.6 Drawing Resonance Structures—Step by Step 33
2.7 Drawing Resonance Structures—By Recognizing Patterns 38
A Lone Pair Next to a Pi Bond 38
A Lone Pair Next to a Positive Charge 41
A Pi Bond Next to a Positive Charge 43
A Pi Bond Between Two Atoms, Where One of Those Atoms Is Electronegative (N, O, etc.) 44
Pi Bonds Going All the Way Around a Ring 45
2.8 Assessing the Relative Importance of Resonance Structures 47
CHAPTER 3ACID–BASE REACTIONS53
3.1 Factor 1—What Atom Is the Charge on? 54
3.2 Factor 2—Resonance 57
3.3 Factor 3—Induction 61
3.4 Factor 4—Orbitals 64
3.5 Ranking the Four Factors 65
3.6 Quantitative Measurement (pKa values) 69
3.7 Predicting the Position of Equilibrium 70
3.8 Showing a Mechanism 71
CHAPTER 4GEOMETRY74
4.1 Orbitals and Hybridization States 74
4.2 Geometry 78
4.3 Lone Pairs 81
CHAPTER 5NOMENCLATURE83
5.1 Functional Group 84
5.2 Unsaturation 86
5.3 Naming the Parent Chain 88
5.4 Naming Substituents 90
5.5 Stereoisomerism 94
5.6 Numbering 97
5.7 Common Names 102
5.8 Going from a Name to a Structure 103
CHAPTER 6CONFORMATIONS104
6.1 How to Draw a Newman Projection 105
6.2 Ranking the Stability of Newman Projections 109
6.3 Drawing Chair Conformations 113
6.4 Placing Groups on the Chair 116
6.5 Ring Flipping 121
6.6 Comparing the Stability of Chairs 127
6.7 Don’t Be Confused by the Nomenclature 131
CHAPTER 7CONFIGURATIONS132
7.1 Locating Stereocenters 133
7.2 Determining the Configuration of a Stereocenter 136
7.3 Nomenclature 144
7.4 Drawing Enantiomers 149
7.5 Diastereomers 154
7.6 Meso Compounds 155
7.7 Drawing Fischer Projections 158
7.8 Optical Activity 163
CHAPTER 8MECHANISMS165
8.1 Curved Arrows 166
8.2 Arrow Pushing 171
8.3 Drawing Intermediates 173
8.4 Nucleophiles and Electrophiles 176
8.5 Bases Versus Nucleophiles 177
8.6 The Regiochemistry Is Contained Within the Mechanism 180
8.7 The Stereochemistry Is Contained Within the Mechanism 183
8.8 A List of Mechanisms 188
CHAPTER 9SUBSTITUTION REACTIONS209
9.1 The Mechanisms 209
9.2 Factor 1—The Electrophile (Substrate) 212
9.3 Factor 2—The Nucleophile 215
9.4 Factor 3—The Leaving Group 217
9.5 Factor 4—The Solvent 220
9.6 Using All Four Factors 223
9.7 Substitution Reactions Teach Us Some Important Lessons 224
CHAPTER 10ELIMINATION REACTIONS226
10.1 The E2 Mechanism 226
10.2 The Regiochemical Outcome of an E2 Reaction 227
10.3 The Stereochemical Outcome of an E2 Reaction 229
10.4 The E1 Mechanism 232
10.5 The Regiochemical Outcome of an E1 Reaction 233
10.6 The Stereochemical Outcome of an E1 Reaction 234
10.7 Substitution vs. Elimination 234
10.8 Determining the Function of the Reagent 235
10.9 Identifying the Mechanism(s) 238
10.10 Predicting the Products 241
CHAPTER 11ADDITION REACTIONS245
11.1 Terminology Describing Regiochemistry 245
11.2 Terminology Describing Stereochemistry 247
11.3 Adding H and H 256
11.4 Adding H and X, Markovnikov 259
11.5 Adding H and Br, Anti-Markovnikov 266
11.6 Adding H and OH, Markovnikov 271
11.7 Adding H and OH, Anti-Markovnikov 275
11.8 Synthesis Techniques 279
11.9 Adding Br and Br; Adding Br and OH 287
11.10 Adding OH and OH, Anti293
11.11 Adding OH and OH, Syn296
11.12 Oxidative Cleavage of an Alkene 298
CHAPTER 12ALCOHOLS302
12.1 Naming and Designating Alcohols 302
12.2 Predicting Solubility of Alcohols 303
12.3 Predicting Relative Acidity of Alcohols 306
12.4 Preparing Alcohols: A Review 309
12.5 Preparing Alcohols via Reduction 310
12.6 Preparing Alcohols via Grignard Reactions 317
12.7 Summary of Methods for Preparing Alcohols 322
12.8 Reactions of Alcohols: Substitution and Elimination 323
12.9 Reactions of Alcohols: Oxidation 327
12.10 Converting an Alcohol into an Ether 329
CHAPTER 13SYNTHESIS332
13.1 One-step Syntheses 333
13.2 Multistep Syntheses 345
13.3 Retrosynthetic Analysis 346
13.4 Creating Your Own Problems 347
Answer Key 349
Index 375
