Organic Chemistry As a Second Language First Semester Topics 4th Edition by David Klein ISBN ISBN 1119624908 978-1119624905

Chapter 1 Bond-Line Drawings 

1.1 How to Read Bond-Line Drawings 

1.2 How to Draw Bond-Line Drawings 

1.3 Mistakes to Avoid 

1.4 More Exercises 

1.5 Identifying Formal Charges 

1.6 Finding Lone Pairs that are Not Drawn 

Chapter 2 Resonance 

2.1 What is Resonance? 

2.2 Curved Arrows: The Tools for Drawing Resonance Structures 

2.3 The Two Commandments 

2.4 Drawing Good Arrows 

2.5 Formal Charges in Resonance Structures 

2.6 Drawing Resonance Structures—Step by Step 

2.7 Drawing Resonance Structures—by Recognizing Patterns 

2.8 Assessing the Relative Importance of Resonance Structures 

Chapter 3 Acid–Base Reactions 

3.1 Factor 1—What Atom is the Charge On? 

3.2 Factor 2—Resonance 

3.3 Factor 3—Induction 

3.4 Factor 4—Orbitals 

3.5 Ranking the Four Factors 

3.6 Other Factors 

3.7 Quantitative Measurement (pKa Values) 

3.8 Predicting the Position of Equilibrium 

3.9 Showing a Mechanism 

Chapter 4 Geometry 

4.1 Orbitals and Hybridization States 

4.2 Geometry 

4.3 Lone Pairs 

Chapter 5 Nomenclature 

5.1 Functional Group 

5.2 Unsaturation 

5.3 Naming the Parent Chain 

5.4 Naming Substituents 

5.5 Stereoisomerism 

5.6 Numbering 

5.7 Common Names 

5.8 Going from a Name to a Structure 

Chapter 6 Conformations 

6.1 How to Draw a Newman Projection 

6.2 Ranking the Stability of Newman Projections 

6.3 Drawing Chair Conformations 

6.4 Placing Groups On the Chair 

6.5 Ring Flipping 

6.6 Comparing the Stability of Chairs 

6.7 Don’t Be Confused by the Nomenclature 

Chapter 7 Configurations 

7.1 Locating Stereocenters 

7.2 Determining the Configuration of a Stereocenter 

7.3 Nomenclature 

7.4 Drawing Enantiomers 

7.5 Diastereomers 

7.6 Meso Compounds 

7.7 Drawing Fischer Projections 

7.8 Optical Activity 

Chapter 8 Mechanisms 

8.1 Introduction to Mechanisms 

8.2 Nucleophiles and Electrophiles 

8.3 Basicity vs. Nucleophilicity 

8.4 Arrow-Pushing Patterns for Ionic Mechanisms 

8.5 Carbocation Rearrangements 

8.6 Information Contained in a Mechanism 

Chapter 9 Substitution Reactions 

9.1 The Mechanisms 

9.2 Factor 1—The Electrophile (Substrate) 

9.3 Factor 2—The Nucleophile 

9.4 Factor 3—The Leaving Group 

9.5 Factor 4—The Solvent 

9.6 Using All Four Factors 

9.7 Substitution Reactions Teach Us Some Important Lessons 

Chapter 10 Elimination Reactions 

10.1 The E2 Mechanism 

10.2 The Regiochemical Outcome of an E2 Reaction 

10.3 The Stereochemical Outcome of an E2 Reaction 

10.4 The E1 Mechanism 

10.5 The Regiochemical Outcome of an E1 Reaction 

10.6 The Stereochemical Outcome of an E1 Reaction 

10.7 Substitution vs. Elimination 

10.8 Determining the Function of the Reagent 

10.9 Identifying the Mechanism(s) 

10.10 Predicting the Products 

Chapter 11 Addition Reactions 

11.1 Terminology Describing Regiochemistry 

11.2 Terminology Describing Stereochemistry 

11.3 Adding H and H 

11.4 Adding H and X, Markovnikov 

11.5 Adding H and Br, Anti-Markovnikov 

11.6 Adding H and OH, Markovnikov 

11.7 Adding H and OH, Anti-Markovnikov 

11.8 Synthesis Techniques 

11.9 Adding Br and Br; Adding Br and OH 

11.10 Adding OH and OH, anti 

11.11 Adding OH and OH, syn 

11.12 Oxidative Cleavage of an Alkene 

Summary of Reactions 

Chapter 12 Alkynes 

12.1 Structure and Properties of Alkynes 

12.2 Preparation of Alkynes 

12.3 Alkylation of Terminal Alkynes 

12.4 Reduction of Alkynes 

12.5 Hydration of Alkynes 

12.6 Keto-Enol Tautomerization 

12.7 Ozonolysis of Alkynes 

Chapter 13 Alcohols 

13.1 Naming and Designating Alcohols 

13.2 Predicting Solubility of Alcohols 

13.3 Predicting Relative Acidity of Alcohols 

13.4 Preparing Alcohols: A Review 

13.5 Preparing Alcohols via Reduction 

13.6 Preparing Alcohols via Grignard Reactions 

13.7 Summary of Methods for Preparing Alcohols 

13.8 Reactions of Alcohols: Substitution and Elimination 

13.9 Reactions of Alcohols: Oxidation 

13.10 Converting an Alcohol Into an Ether 

Chapter 14 Ethers and Epoxides 

14.1 Introduction to Ethers 

14.2 Preparation of Ethers 

14.3 Reactions of Ethers 

14.4 Preparation of Epoxides 

14.5 Ring-Opening Reactions of Epoxides 

Chapter 15 Synthesis 

15.1 One-Step Syntheses 

15.2 Multistep Syntheses 

15.3 Retrosynthetic Analysis 

15.4 Creating Your Own Problems