Organic Chemistry as a Second Language

First Semester Topics

David R. Klein 저자(글)

John Wiley & Sons Inc · 2024년 05월 27일

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작가정보

저자(글) David R. Klein

목차

• 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

기본정보

ISBN	9781119837091 ( 111983709X )
발행(출시)일자	2024년 05월 27일
쪽수	576쪽
크기	204 * 255 * 21 mm / 908 g
총권수	1권
언어	영어