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Foundations of Organic Chemistry

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This book differs from other organic chemistry textbooks in that it is not focused purely on the needs of students studying premed, but rather for all students studying organic chemistry. It directs the reader to question present assumptions rather than to accept what is told, so the second chapter is largely devoted to spectroscopy (rather than finding it much later on as with most current organic chemistry textbooks). Additionally, after an introduction to spectroscopy, thermodynamics and kinetics, the presentation of structural information of compounds and organic families advances from hydrocarbons to alcohols to aldehydes and ketones and, finally, to carboxylic acids.

David R. Dalton received his Ph.D. in Organic Chemistry from the University of California, Los Angeles and is a professor at Temple University. He has held visiting professorships at (1972-1973) 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.


Preface xvii

Acknowledgments xix

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 11

I. CombustionHeats of Reaction 12

C. On the Nature of the Chemical Bond 17

I. Ionic and Nonpolar Covalent Bonds 17

II. Polar Covalent Bonds 22

III. Orbital Hybridization 26

IV. Allotropes of Carbon 39

V. Combination of Ionic and Covalent Bonding 40

Notice to the Student 43

Additional Problems 43

Reference 45

2. An Introduction to Spectroscopy and Selected Spectroscopic Methods in Organic Chemistry 46

A. General Introduction 46

B. X-ray Crystallography 49

C. Photon Spectroscopy 50

I. General Introduction 50

II. UV and VIS Spectroscopy 52

III. IR Spectroscopy 55

IV. Raman Spectroscopy 60

V. Microwave Spectroscopy 60

VI. Magnetic Resonance Spectroscopy 61

a. NMR 61

b. ESR 79

D. MS 80

I. Creation of Ions in the Mass Spectrometer: The Ionization Chamber 81

II. The Separation of Ions by Mass: The Mass Analyzer 82

III. Detecting the Ions 83

Additional Problems 83

Reference 84

3. Structure: The Nomenclature of Hydrocarbons and the Shape of Things to Come 85

A. Introduction 85

B. Nomenclature and Spectroscopy 86

I. Alkanes 86

a. Acyclic Alkanes 86

b. Cyclic Alkanes 93

II. Alkenes, Arenes, and Alkynes 97

a. Alkenes 98

b. Arenes 103

c. Alkynes 108

C. Physical and Chemical Properties; Oxidation and Reduction of Hydrocarbons 111

I. The Concept of Homology 111

II. Oxidation and Reduction 113

a. Oxidation 113

b. Reduction 116

Additional Problems 120

References 123

4. An Introduction to Dynamics 124

A. Introduction 124

B. Review of Some Energy Considerations 126

C. The Barrier between Reactants and Products 128

D. More about the Transition State 130

E. Rotation about Sigma (?) Bonds in Acyclic Alkanes, Alkenes, Alkynes, and Alkyl-Substituted Arenes 133

I. Alkanes 133

II. Alkenes, Alkynes, and Arenes 137

F. Conformational Analysis of Medium-Ring Cyclic Alkanes 138

G. The Conservation of Symmetry during Reactions 156

H. The Measurement of Chirality 169

I. The Wave Nature of Light 169

II. Plane-Polarized Light and Handedness 172

III. Optical Rotatory Dispersion (ORD) and Circular Dichroism (CD) 175

Additional Problems 177

5. Classes of Organic CompoundsA Survey: An Introduction to Solvents and to Acids and Bases and to Computational Chemistry 180

A. Introduction 180

B. General Characteristics of Functional Group Placement 182

C. The Functional Groups and Their Names 183

I. Hydrocarbons 183

a. Alkanes 184

b. Alkenes 184

c. Alkynes 186

d. Arenes 187

II. Alkyl and Aryl Halides 188

III. Alcohols and Phenols 194

IV. Ethers 200

V. Thiols, Thioethers, Disulfi des, and Their Oxides 204

VI. Amines, Hydrazines, and Other Nitrogenous Materials 207

VII. Phosphines, Phosphonium Salts, and Other Phosphorus Derivatives 212

VIII. An Introduction to Organometallic Compounds 214

IX. Compounds Containing Unsaturated Functional Groups 217

a. Aldehydes 217

b. Ketones 223

c. Nitrogen, Sulfur, and Phosphorus Analogues of Aldehydes and Ketones 227

d. Carboxylic Acids 227

e. Carboxylic Acid Derivatives 232

D. An Introduction to Solvents 254

I. Protic and Aprotic Solvents 255

II. Polar and Nonpolar Solvents 256

III. Polarizability 257

IV. Choosing a Solvent 257

a. Solvents for Spectroscopy 257

b. Immiscible Liquids 259

c. Organic Compounds that Dissolve in Water 259

d. Phase Transfer Catalysts 261

E. Acids and Bases 261

I. Brønsted Acids and Bases 262

II. Lewis Acids and Bases 264

III. Hard and Soft Acids and Bases (HSABs) 270

F. Computational Methods 271

I. MM 272

a. Stretching Energy Contribution (Estretch) 272

b. Bending Energy Contribution (Ebend) 272

c. Stretch-Bend Energy Contribution (Estretch-bend) 272

d. van der Waals Energy Contribution (Evan der Waals) 272

e. Torsional Energy Contribution (Etorsional) 273

f. Dipole Interaction Energy and Dipole Moment Contribution (Edipole) 273

Additional Problems 274

Part II Middleground 277

6. The Reactions of Hydrocarbons: Oxidation, Reduction, Substitution, Addition, Elimination, and Rearrangement 291

A. Introduction 291

B. Alkanes 292

I. Oxidation ...


Titel: Foundations of Organic Chemistry
Untertitel: Unity and Diversity of Structures, Pathways, and Reactions
EAN: 9781118005385
ISBN: 978-1-118-00538-5
Digitaler Kopierschutz: Adobe-DRM
Format: E-Book (epub)
Herausgeber: Wiley
Genre: Chemie
Anzahl Seiten: 1532
Veröffentlichung: 04.08.2011
Jahr: 2011
Untertitel: Englisch
Dateigrösse: 62.0 MB