This long-awaited new edition helps students understand and solve the complex problems that organic chemists regularly face, using a step-by-step method and approachable text. With solved and worked-through problems, the author orients discussion of each through the application of various problem-solving techniques. * Teaches organic chemists structured and logical techniques to solve reaction problems and uses a unique, systematic approach. * Stresses the logic and strategy of mechanistic problem solving -- a key piece of success for organic chemistry, beyond just specific reactions and facts * Has a conversational tone and acts as a readable and approachable workbook allowing reader involvement instead of simply straightforward text * Uses 60 solved and worked-through problems and reaction schemes for students to practice with, along with updated organic reactions and illustrated examples * Includes website with supplementary material for chapters and problems: http://tapsoc.yolasite.com
Preface xi
Preface to the First Edition xvii
Acknowledgments xix
1 Problem Analysis in Organic Reaction 1 (18)
Mechanism
1.1 Overview 1 (1)
1.2 Introduction 1 (6)
1.2.1 "Pushing Forward" a Solution in 2 (5)
Formal and Exhaustive Terms
1.2.2 Lessons from this Example 7 (1)
1.3 Avoiding the Quagmire 7 (1)
1.4 The Basic Steps of Problem Analysis 8 (6)
1.4.1 Recognizing the Problem 8 (3)
1.4.2 Analyzing Problems by Asking the 11 (1)
Right Questions, Discarding the
Irrelevant
1.4.3 Drawing a First Outline for 12 (1)
Guidance
1.4.4 Asking the Right Questions and 13 (1)
Proposing the Right Answers... is
enough?
1.5 Intuition and Problem Solving 14 (3)
1.6 Summing Up 17 (2)
References and Notes 17 (2)
2 Electron Flow in Organic Reactions 19 (30)
2.1 Overview 19 (1)
2.2 Introduction 19 (3)
2.3 Practical Rules Governing Electron 22 (20)
Redeployment
2.3.1 Issue 1: Electrons within Orbitals 22 (1)
2.3.2 Issue 2: Electron Transfer and 23 (1)
Stereochemistry
2.3.3 Issue 3: Electron Energy Level 24 (2)
and Accessibility
2.3.4 Issue 4: Electron Flow and 26 (1)
Molecular Active Sectors
2.3.4.1 Case A: π-π Interactions 26 (1)
2.3.4.2 Case B: π → σ 27 (1)
Interactions
2.3.4.3 Case C: When Reactivity 27 (4)
Patterns Seem to Break Down
2.3.5 Issue 5: Electron Traffic and 31 (1)
Electronic Density Differences
2.3.5.1 M° Metals as Electron Source 31 (1)
2.3.5.2 Metal Hydrides and Organic 32 (2)
Hydrides as Electron Source
2.3.6 Issue 6: Creating Zones of High 34 (1)
Electron Density
2.3.6.1 The Natural Polarization 35 (1)
2.3.6.2 Reversing the Natural 35 (1)
Polarization: Umpolung
2.3.7 Issue 7: Electron Flow and Low 36 (1)
Electron Density Zones
2.3.7.1 Identifying LEDZs 36 (1)
2.3.7.2 Creating a New LEDZ in the 37 (4)
Substrate
2.3.7.3 Finding Unsuspected LEDZs among 41 (1)
the Other Reagents in the Mixture
2.3.7.4 When Compounds Show Double 42 (1)
Personality
2.4 Summing Up 42 (2)
2.5 A Flowchart of Organized Problem 44 (5)
Analysis
References and Notes 45 (4)
3 Additional Techniques to Postulate 49 (28)
Organic Reaction Mechanisms
3.1 Overview 49 (1)
3.2 Take Your Time 50 (1)
3.3 Clear and Informative Molecular 50 (3)
Renderings
3.3.1 The Value of Molecular Sketches 50 (2)
3.3.2 Two- Versus Three-Dimensional 52 (1)
Renderings and the "Flat" Organic
Compounds
3.4 Element and Bond Budgets 53 (2)
3.5 Looking at Molecules from Various 55 (3)
Perspectives
3.6 Separate the Grain from the Chaff 58 (1)
3.7 Dissecting Products in Terms of 59 (6)
Reactants: Fragmentation Analysis
3.7.1 The Fundamental Proposition 59 (2)
3.7.2 Adding Potentially Nucleophilic 61 (2)
or Electrophilic Character to Fragments
3.7.3 When Fragmentation Analysis 63 (2)
Fails, Getting Help from Atom Labels
3.8 Oxidation Levels and Mechanism 65 (1)
3.8.1 Methods to Estimate Oxidation 65 (1)
Status
3.9 The Functionality Number 66 (6)
3.9.1 What Exactly Is FN? 66 (1)
3.9.2 Properties of FN 67 (5)
3.10 Combining Fragmentation Analysis and 72 (2)
Functionality Numbers
3.11 Summing Up 74 (3)
References 75 (2)
4 Solved Problem Collection 77 (328)
Problem 1 to 60. See Graphical Problem 79 (326)
Index
Glossary 405 (4)
Subject/Reaction Index 409 (16)
Reagent Index 425 (8)
Author Index 433 (12)
Graphical Problem Index 445
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