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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.

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• Chapter 1 Bond-Line Drawings(p. 1)
• 1.1 How to Read Bond-Line Drawings(p. 1)
• 1.2 How to Draw Bond-Line Drawings(p. 5)
• 1.3 Mistakes to Avoid(p. 7)
• 1.4 More Exercises(p. 7)
• 1.5 Identifying Formal Charges(p. 10)
• 1.6 Finding Lone Pairs That Are Not Drawn(p. 14)
• Chapter 2 Resonance(p. 20)
• 2.1 What Is Resonance?(p. 20)
• 2.2 Curved Arrows: The Tools for Drawing Resonance Structures(p. 21)
• 2.3 The Two Commandments(p. 24)
• 2.4 Drawing Good Arrows(p. 27)
• 2.5 Formal Charges in Resonance Structures(p. 29)
• 2.6 Drawing Resonance Structures-Step by Step(p. 33)
• 2.7 Drawing Resonance Structures-By Recognizing Patterns(p. 38)
• A Lone Pair Next to a Pi Bond(p. 38)
• A Lone Pair Next to a Positive Charge(p. 41)
• A Pi Bond Next to a Positive Charge(p. 43)
• A Pi Bond Between Two Atoms, Where One of Those Atoms Is Electronegative (N, O, etc.)(p. 44)
• Pi Bonds Going All the Way Around a Ring(p. 45)
• 2.8 Assessing the Relative Importance of Resonance Structures(p. 47)
• Chapter 3 Acid-Base Reactions(p. 53)
• 3.1 Factor 1-What Atom Is the Charge on?(p. 54)
• 3.2 Factor 2-Resonance(p. 57)
• 3.3 Factor 3-Induction(p. 61)
• 3.4 Factor 4-Orbitals(p. 64)
• 3.5 Ranking the Four Factors(p. 65)
• 3.6 Quantitative Measurement (pK a values)(p. 69)
• 3.7 Predicting the Position of Equilibrium(p. 70)
• 3.8 Showing a Mechanism(p. 71)
• Chapter 4 Geometry(p. 74)
• 4.1 Orbitals and Hybridization States(p. 74)
• 4.2 Geometry(p. 78)
• 4.3 Lone Pairs(p. 81)
• Chapter 5 Nomenclature(p. 83)
• 5.1 Functional Group(p. 84)
• 5.2 Unsaturation(p. 86)
• 5.3 Naming the Parent Chain(p. 88)
• 5.4 Naming Substituents(p. 90)
• 5.5 Stereoisomerism(p. 94)
• 5.6 Numbering(p. 97)
• 5.7 Common Names(p. 102)
• 5.8 Going from a Name to a Structure(p. 103)
• Chapter 6 Conformations(p. 104)
• 6.1 How to Draw a Newman Projection(p. 105)
• 6.2 Ranking the Stability of Newman Projections(p. 109)
• 6.3 Drawing Chair Conformations(p. 113)
• 6.4 Placing Groups on the Chair(p. 116)
• 6.5 Ring Flipping(p. 121)
• 6.6 Comparing the Stability of Chairs(p. 127)
• 6.7 Don't Be Confused by the Nomenclature(p. 131)
• Chapter 7 Configurations(p. 132)
• 7.1 Locating Stereocenters(p. 133)
• 7.2 Determining the Configuration of a Stereocenter(p. 136)
• 7.3 Nomenclature(p. 144)
• 7.4 Drawing Enantiomers(p. 149)
• 7.5 Diastereomers(p. 154)
• 7.6 Meso Compounds(p. 155)
• 7.7 Drawing Fischer Projections(p. 158)
• 7.8 Optical Activity(p. 163)
• Chapter 8 Mechanisms(p. 165)
• 8.1 Curved Arrows(p. 166)
• 8.2 Arrow Pushing(p. 171)
• 8.3 Drawing Intermediates(p. 173)
• 8.4 Nucleophiles and Electrophiles(p. 176)
• 8.5 Bases Versus Nucleophiles(p. 177)
• 8.6 The Regiochemistry Is Contained Within the Mechanism(p. 180)
• 8.7 The Stereochemistry Is Contained Within the Mechanism(p. 183)
• 8.8 A List of Mechanisms(p. 188)
• Chapter 9 Substitution Reactions(p. 209)
• 9.1 The Mechanisms(p. 209)
• 9.2 Factor 1-The Electrophile (Substrate)(p. 212)
• 9.3 Factor 2-The Nucleophile(p. 215)
• 9.4 Factor 3-The Leaving Group(p. 217)
• 9.5 Factor 4-The Solvent(p. 220)
• 9.6 Using All Four Factors(p. 223)
• 9.7 Substitution Reactions Teach Us Some Important Lessons(p. 224)
• Chapter 10 Elimination Reactions(p. 226)
• 10.1 The E2 Mechanism(p. 226)
• 10.2 The Regiochemical Outcome of an E2 Reaction(p. 227)
• 10.3 The Stereochemical Outcome of an E2 Reaction(p. 229)
• 10.4 The E1 Mechanism(p. 232)
• 10.5 The Regiochemical Outcome of an E1 Reaction(p. 233)
• 10.6 The Stereochemical Outcome of an E1 Reaction(p. 234)
• 10.7 Substitution vs. Elimination(p. 234)
• 10.8 Determining the Function of the Reagent(p. 235)
• 10.9 Identifying the Mechanism(s)(p. 238)
• 10.10 Predicting the Products(p. 241)
• Chapter 11 Addition Reactions(p. 245)
• 11.1 Terminology Describing Regiochemistry(p. 245)
• 11.2 Terminology Describing Stereochemistry(p. 247)
• 11.3 Adding H and H(p. 256)
• 11.4 Adding H and X, Markovnikov(p. 259)
• 11.5 Adding H and Br, Anti-Markovnikov(p. 266)
• 11.6 Adding H and OH, Markovnikov(p. 271)
• 11.7 Adding H and OH, Anti-Markovnikov(p. 275)
• 11.8 Synthesis Techniques(p. 279)
• 11.9 Adding Br and Br; Adding Br and OH(p. 287)
• 11.10 Adding OH and OH, Anti(p. 293)
• 11.11 Adding OH and OH, Syn(p. 296)
• 11.12 Oxidative Cleavage of an Alkene(p. 298)
• Chapter 12 Alcohols(p. 302)
• 12.1 Naming and Designating Alcohols(p. 302)
• 12.2 Predicting Solubility of Alcohols(p. 303)
• 12.3 Predicting Relative Acidity of Alcohols(p. 306)
• 12.4 Preparing Alcohols: A Review(p. 309)
• 12.5 Preparing Alcohols via Reduction(p. 310)
• 12.6 Preparing Alcohols via Grignard Reactions(p. 317)
• 12.7 Summary of Methods for Preparing Alcohols(p. 322)
• 12.8 Reactions of Alcohols: Substitution and Elimination(p. 323)
• 12.9 Reactions of Alcohols: Oxidation(p. 327)
• 12.10 Converting an Alcohol into an Ether(p. 329)
• Chapter 13 Synthesis(p. 332)
• 13.1 One-step Syntheses(p. 333)
• 13.2 Multistep Syntheses(p. 345)
• 13.3 Retrosynthetic Analysis(p. 346)
• 13.4 Creating Your Own Problems(p. 347)
• Answer Key(p. 349)
• Index(p. 375)