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 actually 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 its fifth edition, this valuable study resource covers the characteristics of molecules, the nature of atomic bonds, the relationships between different types of molecules, drawing and naming molecules, and essential molecular reactions.
Table of Contents
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
Chapter 2 Resonance 15
2.1 What is Resonance? 15
2.2 Curved Arrows: The Tools for Drawing Resonance Structures 16
2.3 The Two Commandments 17
2.4 Drawing Good Arrows 20
2.5 Formal Charges in Resonance Structures 22
2.6 Drawing Resonance Structures - Step by Step 25
2.7 Drawing Resonance Structures - by Recognizing Patterns 29
2.8 Assessing the Relative Importance of Resonance Structures 36
Chapter 3 Acid-Base Reactions 41
3.1 Factor 1 - What Atom is the Charge On? 41
3.2 Factor 2 - Resonance 44
3.3 Factor 3 - Induction 47
3.4 Factor 4 - Orbitals 49
3.5 Ranking the Four Factors 50
3.6 Other Factors 53
3.7 Quantitative Measurement (pKa Values) 54
3.8 Predicting the Position of Equilibrium 54
3.9 Showing a Mechanism 55
Chapter 4 Geometry 57
4.1 Orbitals and Hybridization States 57
4.2 Geometry 60
4.3 Lone Pairs 62
Chapter 5 Nomenclature 64
5.1 Functional Group 65
5.2 Unsaturation 66
5.3 Naming the Parent Chain 67
5.4 Naming Substituents 70
5.5 Stereoisomerism 72
5.6 Numbering 74
5.7 Common Names 78
5.8 Going from a Name to a Structure 79
Chapter 6 Conformations 80
6.1 How to Draw a Newman Projection 80
6.2 Ranking the Stability of Newman Projections 84
6.3 Drawing Chair Conformations 86
6.4 Placing Groups on the Chair 90
6.5 Ring Flipping 93
6.6 Comparing the Stability of Chairs 99
6.7 Don’t Be Confused by the Nomenclature 102
Chapter 7 Configurations 103
7.1 Locating Chiral Centers 103
7.2 Determining the Configuration of a Chiral Center 106
7.3 Nomenclature 113
7.4 Drawing Enantiomers 116
7.5 Diastereomers 120
7.6 Meso Compounds 121
7.7 Drawing Fischer Projections 123
7.8 Optical Activity 127
Chapter 8 Mechanisms 129
8.1 Introduction to Mechanisms 129
8.2 Nucleophiles and Electrophiles 129
8.3 Basicity vs. Nucleophilicity 131
8.4 Arrow-Pushing Patterns for Ionic Mechanisms 133
8.5 Carbocation Rearrangements 138
8.6 Information Contained in a Mechanism 142
Chapter 9 Substitution Reactions 145
9.1 The Mechanisms 145
9.2 Factor 1 - The Electrophile (Substrate) 147
9.3 Factor 2 - The Nucleophile 149
9.4 Factor 3 - The Leaving Group 151
9.5 Factor 4 - The Solvent 153
9.6 Using All Four Factors 155
9.7 Substitution Reactions Teach Us Some Important Lessons 156
Chapter 10 Elimination Reactions 157
10.1 The E2 Mechanism 157
10.2 The Regiochemical Outcome of an E2 Reaction 158
10.3 The Stereochemical Outcome of an E2 Reaction 159
10.4 The E1 Mechanism 162
10.5 The Regiochemical Outcome of an E1 Reaction 163
10.6 The Stereochemical Outcome of an E1 Reaction 164
10.7 Substitution vs. Elimination 164
10.8 Determining the Function of the Reagent 165
10.9 Identifying the Mechanism(s) 167
10.10 Predicting the Products 169
Chapter 11 Addition Reactions 172
11.1 Terminology Describing Regiochemistry 172
11.2 Terminology Describing Stereochemistry 174
11.3 Adding H and H 180
11.4 Adding H and X, Markovnikov 183
11.5 Adding H and Br, Anti-Markovnikov 188
11.6 Adding H and OH, Markovnikov 192
11.7 Adding H and OH, Anti-Markovnikov 194
11.8 Synthesis Techniques 198
11.9 Adding Br and Br; Adding Br and OH 204
11.10 Adding OH and OH, Anti 209
11.11 Adding OH and OH, syn 211
11.12 Oxidative Cleavage of an Alkene 213
Summary of Reactions 214
Chapter 12 Alkynes 216
12.1 Structure and Properties of Alkynes 216
12.2 Preparation of Alkynes 218
12.3 Alkylation of Terminal Alkynes 219
12.4 Reduction of Alkynes 221
12.5 Hydration of Alkynes 224
12.6 Keto-Enol Tautomerization 227
12.7 Ozonolysis of Alkynes 232
Chapter 13 Alcohols 234
13.1 Naming and Designating Alcohols 234
13.2 Predicting Solubility of Alcohols 235
13.3 Predicting Relative Acidity of Alcohols 237
13.4 Preparing Alcohols: A Review 239
13.5 Preparing Alcohols via Reduction 240
13.6 Preparing Alcohols via Grignard Reactions 246
13.7 Summary of Methods for Preparing Alcohols 249
13.8 Reactions of Alcohols: Substitution and Elimination 250
13.9 Reactions of Alcohols: Oxidation 253
13.10 Converting an Alcohol into an Ether 255
Chapter 14 Ethers and Epoxides 257
14.1 Introduction to Ethers 257
14.2 Preparation of Ethers 259
14.3 Reactions of Ethers 261
14.4 Preparation of Epoxides 262
14.5 Ring-Opening Reactions of Epoxides 264
Chapter 15 Synthesis 270
15.1 One-Step Syntheses 271
15.2 Multistep Syntheses 283
15.3 Retrosynthetic Analysis 284
15.4 Creating Your Own Problems 285
Detailed Solutions 287
Index 381
