Starkey: Introduction to Strategies for Organic Synthesis

The stepping-stone text for students with a preliminary knowledge of organic chemistry looking to move into organic synthesis research and graduate-level coursework

Organic synthesis is an advanced but important field of organic chemistry, however resources for advanced undergraduates and graduate students moving from introductory organic chemistry courses to organic synthesis research are scarce. Introduction to Strategies for Organic Synthesis is designed to fill this void, teaching practical skills for making logical retrosynthetic disconnections, while reviewing basic organic transformations, reactions, and reactivities.

Divided into seven parts that include sections on Retrosynthesis and Protective Groups; Overview of Organic Transformations; Synthesis of Monofunctional Target Molecules; Synthesis of Target Molecules with Two Functional Groups; Synthesis of Aromatic Target Molecules; Synthesis of Compounds Containing Rings; and Predicting and Controlling Stereochemistry, the book covers everything students need to successfully perform retrosynthetic analyses of target molecule synthesis.

Starting with a review of functional group transformations, reagents, and reaction mechanisms, the book demonstrates how to plan a synthesis, explaining functional group analysis and strategic disconnections. Incorporating a review of the organic reactions covered, it also demonstrates each reaction from a synthetic chemist's point of view, to provide students with a clearer understanding of how retrosynthetic disconnections are made.

Including detailed solutions to over 300 problems, worked-through examples and end-of-chapter comprehension problems, Introduction to Strategies for Organic Synthesis serves as a stepping stone for students with an introductory knowledge of organic chemistry looking to progress to more advanced synthetic concepts and methodologies.

Contents

PART I Synthetic Toolbox 1: Retrosynthesis and Protective Groups

• CHAPTER 1.1 Retrosynthetic Analysis
• CHAPTER 1.2 Protective Groups
• CHAPTER 2.1 Nucleophiles and Electrophiles
• CHAPTER 2.2 Oxidation and Reduction Reactions
• CHAPTER 3.1 Synthesis of Alcohols (ROH)
• CHAPTER 3.2 Synthesis of Alkyl (RX) and Aryl Halides (ArX)
• CHAPTER 3.3 Synthesis of Ethers (ROR')
• CHAPTER 3.4 Synthesis of Thiols (RSH) and Thioethers (RSR')
• CHAPTER 3.5 Synthesis of Amines (RNH2) and Anilines (ArNH2)
• CHAPTER 3.6 Synthesis of Alkenes (R2C=CR2)
• CHAPTER 3.7 Synthesis of Alkynes (RC=CR')
• CHAPTER 3.8 Synthesis of Alkanes (RH)
• CHAPTER 3.9 Synthesis of Aldehydes and Ketones (RCHO, R2C=O)
• CHAPTER 3.10 Synthesis of Carboxylic Acids (RCO2H)
• CHAPTER 3.11 Synthesis of Carboxylic Acid Derivatives
• CHAPTER 4.1 Synthesis of ß-Hydroxy Carbonyls and a,ß-Unsaturated Carbonyls
• CHAPTER 4.2 More Enolate Reactions: Synthesis of 1,3-Dicarbonyls, 1,5-Dicarbonyls, and Cyclohexenones
• CHAPTER 4.3 "Illogical" Disconnections: Umpolung (Polarity Reversal)
• CHAPTER 5.1 Electrophilic Aromatic Substitution (ArH + E+ ? ArE)
• CHAPTER 5.2 Synthesis of Aromatic TMs via Diazonium Salts (ArN2+ + Nu ? ArNu)
• CHAPTER 5.3 Nucleophilic Aromatic Substitution (ArX + Nu: ? ArNu)
• CHAPTER 6.1 Synthesis of Cyclopropanes
• CHAPTER 6.2 Synthesis of Cyclobutanes
• CHAPTER 6.3 Synthesis of Five-Membered Rings (Radical Cyclization Reactions)
• CHAPTER 6.4 Synthesis of Six-Membered Rings (Diels–Alder Reaction)
• CHAPTER 7.1 Reactions That Form Racemates
• CHAPTER 7.2 SN2 Mechanism: Backside Attack
• CHAPTER 7.3 Elimination Mechanisms
• CHAPTER 7.4 Additions to Alkenes and Alkynes
• CHAPTER 7.5 Additions to Carbonyls
• CHAPTER 7.6 Additions to Enolates: Aldol Stereochemistry
• CHAPTER 7.7 Enantioselectivity and Asymmetric Syntheses

Part VII Problems Stereochemistry
Solutions to Problems

• Solutions to Part I: Protective Groups 267
• Solutions to Part II: Nucleophiles, Electrophiles, and Redox 270
• Solutions to Part III: Monofunctional Target Molecules (1-FG TMs) 274
• Solutions to Part IV: Difunctional Target Molecules (2-FG TMs) 286
• Solutions to Part V: Aromatic TMs 303
• Solutions to Part VI: Cyclic TMs 310
• Solutions to Part VII: Stereochemistry 320

Index

About the Author

• Laurie S. Starkey, PHD, is a Full Professor of Chemistry at California State Polytechnic University, Pomona, where she has been teaching organic chemistry and organic synthesis since 1996. Dr. Starkey earned the College of Science's Distinguished Teaching Award in 2000. Her research interests lie in the area of chemical education, including the development and assessment of online learning tools and the creation of educational videos for YouTube and Educator.com.

Book Details

• Paperback: 360 pages
• Publisher: Wiley; 1 edition (February 28, 2012)
• Language: English
• ISBN-10: 0470484098
• ISBN-13: 978-0470484098
• Product Dimensions: 9.3 x 6.2 x 1 inches

List Price: $49.95 

 

Tags: Chemistry, Wiley