Felix A. Carroll (Davidson College)

Perspectives on Structure and Mechanism in Organic Chemistry

• Gebundenes Buch

Produktbeschreibung

PERSPECTIVES ON STRUCTURE AND MECHANISM IN ORGANIC CHEMISTRY

"Beyond the basics" physical organic chemistry textbook, written for advanced undergraduates and beginning graduate students

Based on the author's first-hand classroom experience, Perspectives on Structure and Mechanism in Organic Chemistry uses complementary conceptual models to give new perspectives on the structures and reactions of organic compounds, with the overarching goal of helping students think beyond the simple models of introductory organic chemistry courses. Through this approach, the text better prepares readers to develop new ideas in the future.

In the 3rd Edition, the author thoroughly updates the topics covered and reorders the contents to introduce computational chemistry earlier and to provide a more natural flow of topics, proceeding from substitution, to elimination, to addition. About 20% of the 438 problems have been either replaced or updated, with answers available in the companion solutions manual.

To remind students of the human aspect of science, the text uses the names of investigators throughout the text and references material to original (or accessible secondary or tertiary) literature as a guide for students interested in further reading.

Sample topics covered in Perspectives on Structure and Mechanism in Organic Chemistry include:
_ Fundamental concepts of organic chemistry, covering atoms and molecules, heats of formation and reaction, bonding models, and double bonds
_ Density functional theory, quantum theory of atoms in molecules, Marcus Theory, and molecular simulations
_ Asymmetric induction in nucleophilic additions to carbonyl compounds and dynamic effects on reaction pathways
_ Reactive intermediates, covering reaction coordinate diagrams, radicals, carbenes, carbocations, and carbanions
_ Methods of studying organic reactions, including applications of kinetics in studying reaction mechanisms andArrhenius theory and transition state theory

A comprehensive yet accessible reference on the subject, Perspectives on Structure and Mechanism in Organic Chemistry is an excellent learning resource for students of organic chemistry, medicine, and biochemistry. The text is ideal as a primary text for courses entitled Advanced Organic Chemistry at the upper undergraduate and graduate levels.

Produktdetails

• Verlag: Wiley / Wiley & Sons
• Artikelnr. des Verlages: 1W119808610
• 3. Aufl.
• Seitenzahl: 864
• Erscheinungstermin: 26. Mai 2023
• Englisch
• Abmessung: 286mm x 221mm x 50mm
• Gewicht: 2272g
• ISBN-13: 9781119808619
• ISBN-10: 1119808618
• Artikelnr.: 65155876

Autorenporträt

Felix A. Carroll, PhD is the Joseph R. Morton Professor of Chemistry Emeritus at Davidson College. His research focuses on organic photochemistry and photophysics, kinetics, the synthesis and characterization of insect pheromone analogues, the correlation of molecular structure with physical properties, the combustion characteristics of organic compounds, and chemical education. Dr. Carroll has published extensively in the peer-reviewed literature and was awarded a patent in the field of insect pheromones.

Inhaltsangabe

Preface xi

Chapter 1 Fundamental Models of Organic Chemistry 1

1.1 Atoms and Molecules 1

Basic Concepts 1

Molecular Dimensions 5

1.2 Heats of Formation and Reaction 8

Experimental Determination of Heats of Formation 8

Bond Increment Calculation of Heats of Formation 10

Group Increment Calculation of Heats of Formation 11

Heats of Formation and the Concept of Protobranching 13

Homolytic and Heterolytic Bond Dissociation Energies 15

1.3 Bonding Models 18

Electronegativity and Bond Polarity 20

Complementary Theoretical Models of Bonding 23

Pictorial Representations of Bonding Concepts 27

sp³ Hybridization 28

Are There sp³ Hybrid Orbitals in Methane? 30

Hybridization and Molecular Geometry 34

Variable Hybridization 35

1.4 Complementary Models for the Double Bond 41

The sigma,pi Description of Ethene 41

The Bent Bond Description of Ethene 42

Predictions of Physical Properties with the Two Models 42

1.5 The Role of Complementary Models in Organic Chemistry 46

Problems 47

Chapter 2 Introduction to Computational Chemistry 53

2.1 Hückel Molecular Orbital Theory 53

Correlation of Physical Properties with Results of HMO Calculations 63

Other Parameters Generated Through HMO Theory 67

Properties of Odd Alternant Hydrocarbons 69

The Frost Circle 74

2.2 Aromaticity 75

Benzene 77

Other Aromatic Systems 81

Polycyclic Conjugated Systems 85

Larger Annulenes 90

Dewar Resonance Energy and Absolute Hardness 93

2.3 Contemporary Computational Methods 95

Extended Hückel Theory 95

Semiempirical Methods 96

Ab Initio Theory 97

2.4 Localized Molecular Orbitals 100

Perturbational Molecular Orbital Theory 104

Atoms in Molecules 108

2.5 Density Functional Theory 112

2.6 Another Look at Valence Bond Theory 114

Resonance Structures and Resonance Energies 114

Interpreting Computational Results 117

Problems 119

Chapter 3 Stereochemistry 127

3.1 Representations of Three-Dimensional Structures 127

3.2 Stereoisomerism 130

Isomerism 130

Symmetric, Asymmetric, Dissymmetric, and Nondissymmetric Molecules 133

Fischer Projections 146

Additional Stereochemical Designations 149

3.3 Physical Manifestations of Chirality 159

Optical Activity 159

Configuration and Optical Activity 161

Other Physical Properties of Stereoisomers 166

3.4 Stereotopicity 167

Stereochemical Relationships of Substituents 167

Chirotopicity and Stereogenicity 171

Problems 172

Chapter 4 Molecular Geometry and Steric Energy 183

4.1 Designation of Molecular Conformation 183

4.2 Conformational Analysis 187

Torsional Strain 187

van der Waals Strain 191

Angle Strain and Baeyer Strain Theory 193

Application of Conformational Analysis to Cycloalkanes 194

Conformational Analysis of Substituted Cyclohexanes 198

4.3 Molecular Mechanics 204

4.4 Anomeric Effect 221

4.5 Strain and Molecular Stability 225

Problems 237

Chapter 5 Reactive Intermediates 243

5.1 Reaction Coordinate Diagrams 243

5.2 Radicals 244

Early Evidence for the Existence of Radicals 244

Detection and Characterization of Radica