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 factsHas
The Art of Problem Solving in Organic Chemistry; Contents; Preface; Text Organization; Reference; Preface to the First Edition; Acknowledgments; 1 Problem Analysis in Organic Reaction Mechanism; 1.1 Overview; 1.2 Introduction; 1.2.1 "Pushing Forward" a Solution in Formal and Exhaustive Terms; 1.2.2 Lessons from this Example; 1.3 Avoiding the Quagmire; 1.4 The Basic Steps of Problem Analysis; 1.4.1 Recognizing the Problem; 1.4.2 Analyzing Problems by Asking the Right Questions, Discarding the Irrelevant; 1.4.3 Drawing a First Outline for Guidance 1.4.4 Asking the Right Questions and Proposing the Right Answers... is enough?1.5 Intuition and Problem Solving; 1.6 Summing Up; References and Notes; 2 Electron Flow in Organic Reactions; 2.1 Overview; 2.2 Introduction; 2.3 Practical Rules Governing Electron Redeployment; 2.3.1 Issue 1: Electrons within Orbitals; 2.3.2 Issue 2: Electron Transfer and Stereochemistry; 2.3.3 Issue 3: Electron Energy Level and Accessibility; 2.3.4 Issue 4: Electron Flow and Molecular Active Sectors; 184.108.40.206 Case A: n-π Interactions; 220.127.116.11 Case B: π - σ Interactions 18.104.22.168 Case C: When Reactivity Patterns Seem to Break Down2.3.5 Issue 5: Electron Traffic and Electronic Density Differences; 22.214.171.124 M0 Metals as Electron Source; 126.96.36.199 Metal Hydrides and Organic Hydrides as Electron Source; 2.3.6 Issue 6: Creating Zones of High Electron Density; 188.8.131.52 The Natural Polarization; 184.108.40.206 Reversing the Natural Polarization; 2.3.7 Issue 7: Electron Flow and Low Electron Density Zones; 220.127.116.11 Identifying LEDZs; 18.104.22.168 Creating a New LEDZ in the Substrate; 22.214.171.124 Finding Unsuspected LEDZs among the Other Reagents in the Mixture 126.96.36.199 When Compounds Show Double Personality2.4 Summing Up; 2.5 A Flowchart of Organized Problem Analysis; References and Notes; 3 Additional Techniques to Postulate Organic Reaction Mechanisms; 3.1 Overview; 3.2 Take Your Time; 3.3 Clear and Informative Molecular Renderings; 3.3.1 The Value of Molecular Sketches; 3.3.2 Two- Versus Three-Dimensional Renderings and the "Flat" Organic Compounds; 3.4 Element and Bond Budgets; 3.5 Looking at Molecules from Various Perspectives; 3.6 Separate the Grain from the Chaff; 3.7 Dissecting Products in Terms of Reactants: Fragmentation Analysis 3.7.1 The Fundamental Proposition3.7.2 Adding Potentially Nucleophilic or Electrophilic Character to Fragments; 3.7.3 When Fragmentation Analysis Fails, Getting Help from Atom Labels; 3.8 Oxidation Levels and Mechanism; 3.8.1 Methods to Estimate Oxidation Status; 3.9 The Functionality Number; 3.9.1 What Exactly Is FN?; 3.9.2 Properties of FN; 3.10 Combining Fragmentation Analysis and Functionality Numbers; 3.11 Summing up; References; 4 Solved Problem Collection; Problem 1; Prolem 1: Discussion; Part I: Explaining Products 2 and 3; References; Problem 2; Problem 2: Discussion References and Notes
Description based upon print version of record. Includes bibliographical references at the end of each chapters and indexes. Description based on print version record.