CONTENTS Introduction iii CHAPTER 1 BOND-LINE DRAWINGS 1 1.1 How to Read Bond-Line Drawings 1 1.2 How to Draw Bond-Line Drawings 1.3 Mistakes to Avoid7 1.4 More Exercises 8 1.5 Identifying Formal Charges 10 1.6 Finding Lone Pairs That Are Not Drawn 14 CHAPTER 2 RESONANCE 20 2.1 What Is Resonance?20 2.4 Drawing Good Arrows 27 2.5 Formal Charges in Resonance Structures 29 2.6 Drawing Resonance Structures-Step by Step 33 2.7 Drawing Resonance Structures-By Recognizing Patterns 38 one Pair Next to a Pi Bond 38 A Lone Pair Next to a Positive Charge 41 A Pi Bond Next to a Positive Charge 43 A Pi Bond Between Two Atoms,Where One of Those Atoms Is Electronegative (N.O.etc.)44 Pi Bonds Go ng All the Way Around a Ring 45 2.8 Ass essing the Relative Importance of Resonance Structures 47 CHAPTER 3 ACID-BASE REACTIONS 53 3.1 Factor 1-What Atom Is the Charge on?54 3.2 Factor 2 -Resonance 57 3.3 Factor 3-Induction 62 34 Factor 4-Orbitals 66 3.5 Ranking the Four Factors 67 3.6 Quan easureme avalues)71 3.7 Predicting the Postion of Equilibrium7 3.8 Showing a Mechanism 73 Introduction iii CHAPTER 1 BOND-LINE DRAWINGS 1 1.1 How to Read Bond-Line Drawings 1 1.2How to Draw Bond-Line Drawings 5 1.3 Mistakes to Avoid 7 1.4 More Exercises 8 1.5 Identifying Formal Charges 10 1.6 Finding Lone Pairs That Are Not Drawn 14 CHAPTER 2 RESONANCE 20 2.1 What Is Resonance? 20 2.2 Curved Arrows: The Tools for Drawing Resonance Structures 21 2.3 The Two Commandments 24 2.4 Drawing Good Arrows 27 2.5 Formal Charges in Resonance Structures 29 2.6 Drawing Resonance Structures—Step by Step 33 2.7 Drawing Resonance Structures—By Recognizing Patterns 38 A Lone Pair Next to a Pi Bond 38 A Lone Pair Next to a Positive Charge 41 A Pi Bond Next to a Positive Charge 43 A Pi Bond Between Two Atoms, Where One of Those Atoms Is Electronegative (N, O, etc.) 44 Pi Bonds Going All the Way Around a Ring 45 2.8 Assessing the Relative Importance of Resonance Structures 47 CHAPTER 3 ACID–BASE REACTIONS 53 3.1 Factor 1—What Atom Is the Charge on? 54 3.2Factor 2—Resonance 57 3.3 Factor 3—Induction 62 3.4 Factor 4—Orbitals 66 3.5 Ranking the Four Factors 67 3.6 Quantitative Measurement (pKa values) 71 3.7 Predicting the Position of Equilibrium 71 3.8 Showing a Mechanism 73 ix CONTENTS 6753_Klein_00.qxd 5/1/07 5:02 PM Page ix