A foundation for success in advanced organic chemistry courses-and careers Graduate students taking advanced organic chemistry courses often need a refresher on the discipline before they can move on to more specialized topics. This is especially true of students whose last formal exposure to organic chemistry was during their undergraduate studies. Organic Chemistry: An Intermediate Text bridges this gap, reacquainting students with basic organic chemistry while introducing them to the most important advanced topics in the field today. The book presents a principles-focused discussion of organic chemistry from a unique mechanistic and structural perspective. Beginning with the classification of functional groups by bonding patterns and oxidation levels, it describes general mechanistic considerations vital to the understanding of functional group transformations-from electron movement to stereoelectronic effects. Building on this mechanistic framework, the text then provides insight into synthetic transformations commonly employed in modern organic chemistry. Updated and revised throughout, the Second Edition of Organic Chemistry: An Intermediate Text features: * A stronger emphasis on mechanisms * An expanded overview of resonance and aromaticity * A new section on uses of organopalladium chemistry and olefin metathesis in carbon-carbon bond formation * A revised examination of free radical reactions for carbon-carbon bond formation * A fuller discussion of Diels-Alder chemistry Chapterending problems, many of which are new to this edition, help to reinforce pivotal concepts required to fully comprehend the text material. This book is illustrated with abundant structures and figures that demonstrate these concepts.
Preface to the First Edition.
1. Functional Groups and Chemical Bonding.
Conjugated p Systems.
2. Oxidation States of Organic Compounds.
Oxidation States in Alkanes.
Oxidation States in Alkenes.
Oxidation States in Common Functional Groups.
Oxidation Level Changes During Reactions.
3. Acidity and Basicity.
Bronsted and Lewis Acids and Bases.
Structural Effects on Acidity.
4. Curved-Arrow Notation.
Heterolytic Bond Cleavages.
Heterolytic Bond Formation.
Homolytic Bond Making and Bond Breaking.
Depiction of Mechanism.
5. Mechanisms of Organic Reactions.
Structure of the Activated Complex.
Determining Activation Energies.
6. Stereochemical and Conformational Isomerism.
Configuration of Chiral Centers.
Physical Properties of Enantiomers.
Resolution of Enantiomers.
Formation of Enantiomers.
Formation of Diastereomers.
Stereochemistry to Deduce Mechanism.
Strain in Ring Systems.
7. Functional Group Synthesis.
Functional Group Manipulation.
Imines and Imine Derivatives.
8. Carbon-Carbon Bond Formation between Carbon.
Nucleophiles and Carbon Electrophiles.
Generation of Nucleophilic Carbon Reagents.
Generation of Electrophilic Carbon Reagents.
Matching Nucleophiles with Electrophiles.
Diastereoselection in Aldol Reactions.
Neutral Carbon Nucleophiles.
Metal-Catalyzed Carbon-Carbon Bond Formation.
Pd(0)-Catalyzed Carbon-Carbon Bond Formation.
Bond Formation by Free-Radical Reactions.
10. Planning Organic Syntheses.
Carbon Skeleton Synthesis.
11. Structure Determination of Organic Compounds.
Nuclear Magnetic Resonance.
Descriptions of Spin Systems.
Structure Identification by 1H NMR.
IR Stretching Frequencies.
Use of IR Spectroscopy for Structure Determination.
Solutions to Chapter
Many entering graduate students took organic chemistry as sophomores but have since had little exposure to organic chemistry in a formal sense. Because of this time lapse in their organic preparation, they often have difficulty performing well when placed directly into mainstream graduate-level organic courses. This text aims to bridge the gap between introductory-level instruction and more advanced graduate-level texts, reviewing the basics as well as presenting the more advanced ideas that are currently of importance in organic chemistry.