Introduction to Strategies for Organic Synthesis

Sofort lieferbar | Lieferzeit:3-5 Tage I
Laurie S. Starkey
687 g
226x157x25 mm

Preface xixAcknowlegments xxiCHAPTER 1 Synthetic Toolbox 1: Retrosynthesis and Protective Groups 11.1 Retrosynthetic Analysis 31.2 Protective Groups 11CHAPTER 1 Problems Protective Groups 19CHAPTER 2 Synthetic Toolbox 2: Overview of Organic Transformations 212.1 Nucleophiles and Electrophiles 232.2 Oxidation and Reduction Reactions 27CHAPTER 2 Problems Nucleophiles, Electrophiles, and Redox 41CHAPTER 3 Synthesis of Monofunctional Target Molecules (1-FG TMs) 453.1 Synthesis of Alcohols (ROH) and Phenols (ArOH) 473.2 Synthesis of Alkyl (RX) and Aryl Halides (ArX) 613.3 Synthesis of Ethers (ROR') 673.4 Synthesis of Thiols (RSH) and Thioethers (RSR¿) 733.5 Synthesis of Amines (RNH2) and Anilines (ArNH2) 773.6 Synthesis of Alkenes (R2C?TCR2) 853.7 Synthesis of Alkynes (RC identical to CR') 933.8 Synthesis of Alkanes (RH) 973.9 Synthesis of Aldehydes and Ketones (RCHO, R2C?TO) 1053.10 Synthesis of Carboxylic Acids (RCO2H) 1173.11 Synthesis of Carboxylic Acid Derivatives 125CHAPTER 3 Problems 1-FG TMs 139CHAPTER 4 Synthesis of Target Molecules with Two Functional Groups (2-FG TMs) 1434.1 Synthesis of ß?Hydroxy Carbonyls and alpha,ß?Unsaturated Carbonyls 1454.2 More Enolate Reactions: Synthesis of 1,3?Dicarbonyls, 1,5?Dicarbonyls, and Cyclohexenones 1574.3 "Illogical" 2?Group Disconnections: Umpolung (Polarity Reversal) 171CHAPTER 4 Problems 2-FG TMs 183CHAPTER 5 Synthesis of Aromatic Target Molecules 1875.1 Electrophilic Aromatic Substitution (ArH + E+ --> ArE) 1895.2 Synthesis of Aromatic TMs via Diazonium Salts (ArN2 + + Nu: --> ArNu) 2015.3 Nucleophilic Aromatic Substitution (ArX + Nu: --> ArNu) 205CHAPTER 5 Problems Aromatic TMs 209CHAPTER 6 Synthesis of Compounds Containing Rings 2116.1 Synthesis of Cyclopropanes 2136.2 Synthesis of Cyclobutanes 2156.3 Synthesis of Five?Membered Rings (Radical Cyclization Reactions) 2176.4 Synthesis of Six?Membered Rings (Diels-Alder Reaction) 221CHAPTER 6 Problems Cyclic TMs 231CHAPTER 7 Predicting and Controlling Stereochemistry 2357.1 Reactions that Form Racemates 2377.2 SN2 Mechanism: Backside Attack 2437.3 Elimination Mechanisms 2457.4 Additions to Alkenes and Alkynes 2477.5 Additions to Carbonyls 2517.6 Additions to Enolates: Aldol Stereochemistry 2577.7 Enantioselectivity and Asymmetric Syntheses 261CHAPTER 7 Problems Stereochemistry 269CHAPTER 8 Transition Metal-Mediated Carbon-Carbon Bond Formation 2738.1 Transition Metal Coordination Complexes 2758.2 Organometallic Reaction Mechanisms 2838.3 Carbonylation and Decarbonylation 2918.4 (ArX + Alkene --> Ar?Alkene) 2958.5 Palladium?Catalyzed Cross?Coupling Reactions (RX + R'M --> R?R') 2978.6 Olefin Metathesis Reactions 3038.7 Retrosynthesis: Disconnections Based on Metal-Mediated Reactions 307CHAPTER 8 Problems Transition Metal-Mediated Synthesis 309SOLUTIONS TO PROBLEMS 313Index 389
Bridging the Gap Between Organic Chemistry Fundamentals and Advanced Synthesis ProblemsIntroduction to Strategies of Organic Synthesis bridges the knowledge gap between sophomore-level organic chemistry and senior-level or graduate-level synthesis to help students more easily adjust to a synthetic chemistry mindset. Beginning with a thorough review of reagents, functional groups, and their reactions, this book prepares students to progress into advanced synthetic strategies. Major reactions are presented from a mechanistic perspective and then again from a synthetic chemist's point of view to help students shift their thought patterns and teach them how to imagine the series of reactions needed to reach a desired target molecule.Success in organic synthesis requires not only familiarity with common reagents and functional group interconversions, but also a deep understanding of functional group behavior and reactivity. This book provides clear explanations of such reactivities and explicitly teaches students how to make logical disconnections of a target molecule.This new Second Edition of Introduction to Strategies for Organic Synthesis:* Reviews fundamental organic chemistry concepts including functional group transformations, reagents, stereochemistry, and mechanisms
* Explores advanced topics including protective groups, synthetic equivalents, and transition-metal mediated coupling reactions
* Helps students envision forward reactions and backwards disconnections as a matter of routine
* Gives students confidence in performing retrosynthetic analyses of target molecules Includes fully-worked examples, literature-based problems, and over 450 chapter problems with detailed solutions
* Provides clear explanations in easy-to-follow, student-friendly language
* Focuses on the strategies of organic synthesis rather than a catalogue of reactions and modern reagentsThe prospect of organic synthesis can be daunting at the outset, but this book serves as a useful stepping stone to refresh existing knowledge of organic chemistry while introducing the general strategies of synthesis. Useful as both a textbook and a bench reference, this text provides value to graduate and advanced undergraduate students alike.