LAURIE S. STARKEY, PHD, is a Professor of Organic Chemistry at California State Polytechnic University, Pomona, where she has been teaching organic chemistry and organic synthesis since 1996. Her research focuses on chemical education, including the development and assessment of online learning tools and the creation of educational videos and animations. Dr. Starkey was awarded the Cal Poly Pomona College of Science's Distinguished Teaching Award in 2000, and the Provost's Award in Teaching Excellence in 2013.

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• 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≡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 β©\Hydroxy Carbonyls and α,β©\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