David R. Dalton

Foundations of Organic Chemistry

Unity and Diversity of Structures, Pathways, and Reactions

• Gebundenes Buch

Produktbeschreibung

Learn the fundamentals and foundations of modern organic chemistry with this comprehensive guide

Foundations of Organic Chemistry: Unity and Diversity of Structures, Pathways, and Reactions, 2nd Edition, is a substantive guide for students beginning their study of organic chemistry and instructors, as well as senior undergraduates and graduate students seeking to further their understanding of the subject.

Foundations of Organic Chemistry is a serious attempt to show students who want to learn organic chemistry how we know what we know about the subject and to guide them to learn.

In this work, the emphasis of the discussion of structures, pathways, and reactions is placed on the original literature and the fundamentals and use of spectroscopic and kinetic tools. Application of the resulting working knowledge of the substance of organic chemistry will lead the serious student to ask additional questions and, ultimately, to solve problems we face.

The book also includes solutions guides for instructors and lecturers, as well as access to a companion website for furthering the reader's knowledge of organic chemistry.

Produktdetails

• Verlag: Wiley / Wiley & Sons
• Artikelnr. des Verlages: 1W119656420
• 2. Aufl.
• Seitenzahl: 1376
• Erscheinungstermin: 11. August 2020
• Englisch
• Abmessung: 257mm x 211mm x 56mm
• Gewicht: 2530g
• ISBN-13: 9781119656425
• ISBN-10: 1119656427
• Artikelnr.: 58382092

Autorenporträt

DAVID R. DALTON received his Ph.D. in Organic Chemistry from the University of California, Los Angeles and is a Professor Emeritus at Temple University. He has held visiting professorships (1972-1973) at Israel Institute of Technology (Technion), Haifa, Israel; (1976-1977) Yale University, New Haven, Connecticut; (1988-1989) Bryn Mawr College, Bryn Mawr, Pennsylvania; and in 1992, he was the visiting master teacher in Residence, Clemson University, Clemson, South Carolina.

Inhaltsangabe

Prologue xix

Acknowledgments xxi

About the Companion Website xxiii

Part I Background 1

1. An Introduction to Structure and Bonding 5

A. The Sources of Carbon Compounds 5

I. How Do We Know a Material is Pure? 6

B. More About Hydrocarbons: Heats of Combustion and Reaction 9

I. Combustion: Heats of Reaction 9

C. On The Nature of the Chemical Bond 12

I. Ionic and Nonpolar Covalent Bonds 12

II. Polar Covalent Bonds: Mixing Orbitals and Molecular Orbitals 17

III. The Use of Orbital Hybridization and Molecular Orbitals 21

a. Summary Comment on Bonding Models 37

IV. Allotropes of Carbon 37

V. Combination of Ionic and Covalent Bonding 37

Notice to the Student 41

Problems 41

Notes and References 44

2. An Introduction to Spectroscopy and Selected Spectroscopic Methods in Organic Chemistry 49

A. General Introduction. The Electromagnetic Spectrum 49

B. X-Ray Crystallography 51

C. Photon Spectroscopy 52

I. General Introduction 52

II. Ultraviolet and Visible Spectroscopy 54

III. Infrared Spectroscopy 56

IV. Raman Spectroscopy 58

V. Microwave Spectroscopy 58

VI. Magnetic Resonance Spectroscopy 59

a. Nuclear Magnetic Resonance (NMR) 59

1. The Chemical Shift 62

2. Multiplicity (The Coupling Constant: Spin-Spin Splitting) 65

3. The Integrated Area 66

4. Expansion of the Principle 67

5. NMR in Two Dimensions 69

6. Double Resonance 70

7. ¯13C, ¯19F, and ¯31P NMR Spectroscopy 72

b. Electron Spin Resonance (ESR) Spectroscopy or Electron Paramagnetic Resonance (EPR) Spectroscopy 74

D. Mass Spectrometry 75

I. Creation of Ions in the Mass Spectrometer: The Ionization Chamber 76

II. The Separation of Ions by Mass: The Mass Analyzer 76

III. Detecting the Ions 77

Problems 77

Notes and References 78

3. Structure: The Nomenclature of Hydrocarbons and the Shape of Things to Come 83

A. Introduction 83

B. Nomenclature and Spectroscopy 84

I. Alkanes in Two and Three Dimensions 84

a. Acyclic Alkanes 84

b. Cyclic Alkanes 89

II. Alkenes, Arenes, and Alkynes in Two and Three Dimensions 92

a. Alkenes 93

b. Arenes 97

c. Alkynes 102

C. Physical and Chemical Properties: Oxidation and Reduction of Hydrocarbons 104

I. The Concept of Homology 105

II. Oxidation and Reduction 105

a. Oxidation 105

b. Reduction 108

Problems 112

Notes and References 115

4. An Introduction to Dynamics 119

A. Introduction 119

B. Review of Some Energy Considerations 120

C. The Barrier Between Reactants and Products 121

D. More About the Transition State 123

E. Rotation About Sigma (Sigma) Bonds in Acyclic Alkanes, Alkenes, Alkynes, and Alkyl-Substituted Arenes 126

I. Alkanes 126

II. Alkenes, Alkynes, and Alkyl-Substituted Arenes 129

F. Conformational Analysis of Medium-Ring Cyclic Alkanes 131

G. The Conservation of Symmetry During Reactions 146

H. The Measurement of Chirality 156

I. The Wave Nature of Light 156

II. Plane-Polarized Light and Handedness 157

III. Optical Rotatory Dispersion (ORD) and Circular Dichroism (CD) 160

Problems 162

Notes and References 165

5. Classes of Organic Compounds: A Survey Along with