Über die Autorin bzw. den Autor

ROBERT V. HOFFMAN, PhD, is Professor Emeritus of Chemistry at New Mexico State University in Las Cruces, New Mexico.

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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

Chapter-ending 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.

Aus dem Klappentext

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

Chapter-ending 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.

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Organic Chemistry

John Wiley & Sons

Contents

Preface.................................................................................................xiiiPreface to the First Edition............................................................................xv1 Functional Groups and Chemical Bonding................................................................1Functional Groups.......................................................................................1Orbitals................................................................................................5Bonding Schemes.........................................................................................7Antibonding Orbitals....................................................................................13Resonance...............................................................................................18Conjugated [pi] Systems.................................................................................21Aromaticity.............................................................................................23Bibliography............................................................................................26Problems................................................................................................272 Oxidation States of Organic Compounds.................................................................32Oxidation Levels........................................................................................32Oxidation States in Alkanes.............................................................................34Oxidation States in Alkenes.............................................................................34Oxidation States in Common Functional Groups............................................................35Oxidation Level Changes During Reactions................................................................35Bibliography............................................................................................41Problems................................................................................................413 Acidity and Basicity..................................................................................47Bronsted and Lewis Acids and Bases......................................................................47Acid Strength...........................................................................................49Acid-Base Equilibria....................................................................................53Amphoteric Compounds....................................................................................56Structural Effects on Acidity...........................................................................56Bibliography............................................................................................63Problems................................................................................................634 Curved-Arrow Notation.................................................................................69Electron Movement.......................................................................................69Heterolytic Bond Cleavages..............................................................................70Heterolytic Bond Formation..............................................................................71Homolytic Bond Making and Bond Breaking.................................................................73Resonance Structure.....................................................................................75Depiction of Mechanism..................................................................................76Bibliography............................................................................................82Problems................................................................................................825 Mechanisms of Organic Reactions.......................................................................86Activation Energy.......................................................................................87Activated Complex.......................................................................................88Reaction Energetics.....................................................................................89Structure of the Activated Complex......................................................................91Hammond Postulate.......................................................................................96Reaction Kinetics.......................................................................................99Determining Activation Energies.........................................................................104Isotope Effects.........................................................................................105Electronic Effects......................................................................................110Hammett Equation........................................................................................111Bibliography............................................................................................118Problems................................................................................................1186 Stereochemical and Conformational Isomerism...........................................................124Stereochemical Structures...............................................................................125Chirality...............................................................................................128Configuration of Chiral Centers.........................................................................129Multiple Stereocenters..................................................................................132Optical Activity........................................................................................137Absolute Configuration..................................................................................138Physical Properties of Enantiomers......................................................................139Resolution of Enantiomers...............................................................................140Stereoselective Reactions...............................................................................144Formation of Enantiomers................................................................................144Formation of Diastereomers..............................................................................146Stereochemistry to Deduce Mechanism.....................................................................152Conformational Analysis.................................................................................157Conformational Energies.................................................................................164A Values................................................................................................166Strain in Ring Systems..................................................................................167Stereoelectronic Effects................................................................................172Bibliography............................................................................................176Problems................................................................................................1767 Functional Group...