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The Art of Problem Solving in Organic Chemistry, 2nd Edition

ISBN: 978-1-118-82963-9
470 pages
June 2014
The Art of Problem Solving in Organic Chemistry, 2nd Edition (1118829638) cover image


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
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Table of Contents

Preface xi

Preface to the First Edition xvii

Acknowledgments xix

1 Problem Analysis in Organic Reaction Mechanism 1

1.1 Overview, 1

1.2 Introduction, 1

1.2.1 "Pushing Forward" a Solution in Formal and Exhaustive Terms, 2

1.2.2 Lessons from this Example, 7

1.3 Avoiding the Quagmire, 7

1.4 The Basic Steps of Problem Analysis, 8

1.4.1 Recognizing the Problem, 8

1.4.2 Analyzing Problems by Asking the Right Questions, Discarding the Irrelevant, 11

1.4.3 Drawing a First Outline for Guidance, 12

1.4.4 Asking the Right Questions and Proposing the Right Answers . . . is enough?, 13

1.5 Intuition and Problem Solving, 14

1.6 Summing Up, 17

References and Notes, 17

2 Electron Flow in Organic Reactions 19

2.1 Overview, 19

2.2 Introduction, 19

2.3 Practical Rules Governing Electron Redeployment, 22

2.3.1 Issue 1: Electrons within Orbitals, 22

2.3.2 Issue 2: Electron Transfer and Stereochemistry, 23

2.3.3 Issue 3: Electron Energy Level and Accessibility, 24

2.3.4 Issue 4: Electron Flow and Molecular Active Sectors, 26 Case A: π–π Interactions, 26 Case B.: π → σ Interactions, 27 Case C: When Reactivity Patterns Seem to Break Down, 27

2.3.5 Issue 5: Electron Traffic and Electronic Density Differences, 31 M0 Metals as Electron Source, 31 Metal Hydrides and Organic Hydrides as Electron Source, 32

2.3.6 Issue 6: Creating Zones of High Electron Density, 34 The Natural Polarization, 35 Reversing the Natural Polarization: Umpolung, 35

2.3.7 Issue 7: Electron Flow and Low Electron Density Zones, 36 Identifying LEDZs, 36 Creating a New LEDZ in the Substrate, 37 Finding Unsuspected LEDZs among the Other Reagents in the Mixture, 41 When Compounds Show Double Personality, 42

2.4 Summing Up, 42

2.5 A Flowchart of Organized Problem Analysis, 44

References and Notes, 45

3 Additional Techniques to Postulate Organic Reaction Mechanisms 49

3.1 Overview, 49

3.2 Take Your Time, 50

3.3 Clear and Informative Molecular Renderings, 50

3.3.1 The Value of Molecular Sketches, 50

3.3.2 Two- Versus Three-Dimensional Renderings and the "Flat" Organic Compounds, 52

3.4 Element and Bond Budgets, 53

3.5 Looking at Molecules from Various Perspectives, 55

3.6 Separate the Grain from the Chaff, 58

3.7 Dissecting Products in Terms of Reactants: Fragmentation Analysis, 59

3.7.1 The Fundamental Proposition, 59

3.7.2 Adding Potentially Nucleophilic or Electrophilic Character to Fragments, 61

3.7.3 When Fragmentation Analysis Fails, Getting Help from Atom Labels, 63

3.8 Oxidation Levels and Mechanism, 65

3.8.1 Methods to Estimate Oxidation Status, 65

3.9 The Functionality Number, 66

3.9.1 What Exactly Is FN?, 66

3.9.2 Properties of FN, 67

3.10 Combining Fragmentation Analysis and Functionality Numbers, 72

3.11 Summing Up, 74

References, 75

4 Solved Problem Collection 77

Problem 1 to 60. See Graphical Problem Index, 79

Glossary 405

Subject/Reaction Index 409

Reagent Index 425

Author Index 433

Graphical Problem Index 445

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Author Information

Miguel Alonso is a Professor of Organic and Ecological Chemistry at the Universidad de Los Andes in Venezuela. With over forty years of teaching experience, he has also led courses on these topics in the US, Europe, and Latin America. His previous research interest includes the theory and application of metal carbenoids in cyclopropanes and heterocycles, and currently, focuses on chemical ecology of tropical mountain ecosystems. Among his publications, Dr. Alonso has over 90 research articles, 5 book chapters, and 4 books including the first edition of The Art of Problem Solving in Organic Chemistry, published by Wiley.
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“Summing Up: Highly recommended. Graduate students and above.”  (Choice, 1 May 2015)

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