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Organic Chemistry as a Second Language
First Semester Topics
David R. Klein (Author)
9781119837091, Wiley
Paperback / softback, published 27 May 2024
576 pages
25.2 x 20.3 x 2.3 cm, 0.998 kg
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.
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
Subject Areas: Chemistry [PN]
