Organic chemistry / G. Marc Loudon.

Format:

Book

Author/Creator:

Loudon, G. Marc.

Contributor:

Class of 1932 Fund.

Language:

English

Subjects (All):

Chemistry, Organic.

Physical Description:

1 volume (various pagings) : illustrations ; 27 cm

Edition:

Fourth edition.

Place of Publication:

New York : Oxford University Press, 2002.

Summary:

With a reputation for outstanding scientific quality, Organic Chemistry by G. Marc Loudon is a textbook that students actually want to read. This much-anticipated fourth edition continues its predecessors' popular and unique mechanistic approach within a functional group framework. Enhanced biological and biochemical material make it ideal for chemistry majors as well as premedical and prepharmacy students taking a full-year, sophomore-level course. Loudon's excellent use of language and reader-friendly style transform organic chemistry into a logical, understandable, and exciting subject for students. In use at undergraduate and graduate schools of all levels, this authoritative yet accessible volume is packed with effective analogies that enliven and clarify rigorous discussions of important concepts. For example, Loudon uses a flute player jumping between musical octaves to explain transitions between quantum levels. An engaging detective with combined characteristics from Sherlock Holmes and James Bond depicts resonance structures. Thanks to humorous characters like Flick Flaskflinger and Professor Havno Scentz, problem solving becomes simultaneously challenging and entertaining. Varying from the routine to the complex, Loudon's problems are renowned for their originality, their range of difficulty levels, and their ability to teach students to understand and predict organic reactivity rather than just memorize facts. In addition, Loudon blends biological, environmental, and industrial applications of organic chemistry into the body of the text -- rather than separating them as "special topics" -- giving students an integrated sense of the subject in its real-life context.

Contents:

Chapter 1 Chemical Bonding and Chemical Structure 1

1.2 Classical Theories of Chemical Bonding 3

1.3 Structures of Covalent Compounds 11

1.4 Resonance Structures 18

1.5 Wave Nature of the Electron 20

1.6 Electronic Structure of the Hydrogen Atom 21

1.7 Electronic Structures of More Complex Atoms 27

1.8 Another Look at the Covalent Bond: Molecular Orbitals 30

1.9 Hybrid Orbitals 35

Chapter 2 Alkanes 43

2.1 Hydrocarbons 43

2.2 Unbranched Alkanes 45

2.3 Conformations of Alkanes 47

2.4 Constitutional Isomers and Nomenclature 53

2.5 Cycloalkanes and Skeletal Structures 62

2.6 Physical Properties of Alkanes 65

2.7 Combustion and Elemental Analysis 70

2.8 Occurrence and Use of Alkanes 73

2.9 Functional Groups, Compound Classes, and the "R" Notation 76

Chapter 3 Acids and Bases: The Curved-Arrow Notation 82

3.1 Lewis Acid-Base Association Reactions 82

3.2 Electron-Pair Displacement Reactions 85

3.3 Review of the Curved-Arrow Notation 89

3.4 Bronsted-Lowry Acids and Bases 91

3.5 Free Energy and Chemical Equilibrium 96

3.6 Relationship of Structure to Acidity 99

Chapter 4 Introduction to Alkenes: Structure and Reactivity 111

4.1 Structure and Bonding in Alkenes 111

4.3 Unsaturation Number 126

4.4 Physical Properties of Alkenes 127

4.5 Relative Stabilities of Alkene Isomers 128

4.6 Addition Reactions of Alkenes 133

4.7 Addition of Hydrogen Halides to Alkenes 134

4.8 Reaction Rates 142

4.9 Catalysis 150

Chapter 5 Addition Reactions of Alkenes 160

5.1 Reactions of Alkenes with Halogens 160

5.2 Writing Organic Reactions 164

5.3 Conversion of Alkenes Into Alcohols 165

5.4 Ozonolysis of Alkenes 173

5.5 Free-Radical Addition of Hydrogen Bromide to Alkenes 177

5.6 Polymers: Free-Radical Polymerization of Alkenes 190

5.7 Alkenes in the Chemical Industry 192

Chapter 6 Principles of Stereochemistry 201

6.1 Enantiomers, Chirality, and Symmetry 201

6.2 Nomenclature of Enantiomers: The R,S System 206

6.3 Physical Properties of Enantiomers: Optical Activity 209

6.4 Racemates 213

6.5 Stereochemical Correlation 215

6.6 Diastereomers 217

6.7 Meso Compounds 221

6.8 Enantiomeric Resolution 224

6.9 Chiral Molecules Without Asymmetric Atoms 226

6.10 Conformational Stereoisomers 228

6.11 Fischer Projections 231

6.12 The Postulation of Tetrahedral Carbon 235

Chapter 7 Cyclic Compounds: Stereochemistry of Reactions 244

7.1 Relative Stabilities of the Monocyclic Alkanes 244

7.2 Conformations of Cyclohexane 245

7.3 Monosubstituted Cyclohexanes: Conformational Analysis 253

7.4 Disubstituted Cyclohexanes 257

7.5 Cyclopentane, Cyclobutane, and Cyclopropane 265

7.6 Bicyclic and Polycyclic Compounds 268

7.7 Relative Reactivities of Stereoisomers 275

7.8 Reactions That Form Stereoisomers 278

7.9 Stereochemistry of Chemical Reactions 283

Chapter 8 Introduction to Alkyl Halides, Alcohols, Ethers, Thiols, and Sulfides 301

8.2 Structures 310

8.3 Effect of Molecular Polarity and Hydrogen Bonding on Physical Properties 311

8.4 Solvents in Organic Chemistry 316

8.5 Applications of Solubility and Solvation Principles 322

8.6 Acidity of Alcohols and Thiols 328

8.7 Basicity of Alcohols and Ethers 333

8.8 Grignard and Organolithium Reagents 334

8.9 Industrial Preparation and Use of Alkyl Halides, Alcohols, and Ethers 338

Chapter 9 Chemistry of Alkyl Halides 351

9.1 An Overview of Nucleophilic Substitution and [beta]-Elimination Reactions 351

9.2 Equilibrium in Nucleophilic Substitution Reactions 356

9.3 Reaction Rates 357

9.4 The S[subscript N]2 Reaction 360

9.5 The E2 Reaction 371

9.6 The S[subscript N]1 and E1 Reactions 382

9.7 Summary of Substitution and Elimination Reactions of Alkyl Halides 391

9.8 Carbenes and Carbenoids 394

Chapter 10 Chemistry of Alcohols and Thiols 408

10.1 Dehydration of Alcohols 408

10.2 Reactions of Alcohols with Hydrogen Halides 411

10.3 Sulfonate and Inorganic Ester Derivatives of Alcohols 414

10.4 Conversion of Alcohols into Alkyl Halides: Summary 422

10.5 Oxidation and Reduction in Organic Chemistry 423

10.6 Oxidation of Alcohols 430

10.7 Biological Oxidation of Ethanol 433

10.8 Chemical and Stereochemical Group Equivalence 436

10.9 Oxidation of Thiols 443

10.10 Synthesis of Alcohols 446

10.11 Design of Organic Synthesis 447

Chapter 11 Chemistry of Ethers, Epoxides, Glycols, and Sulfides 455

11.1 Synthesis of Ethers and Sulfides 455

11.2 Synthesis of Epoxides 461

11.3 Cleavage of Ethers 464

11.4 Nucleophilic Substitution Reactions of Epoxides 467

11.5 Preparation and Oxidative Cleavage of Glycols 473

11.6 Oxonium and Sulfonium Salts 479

11.7 Neighboring-Group Participation: Intramolecular Reactions 481

11.8 Oxidation of Ethers and Sulfides 484

11.9 The Three Fundamental Operations of Organic Synthesis 485

Chapter 12 Introduction to Spectroscopy: Infrared Spectroscopy and Mass Spectrometry 497

12.2 Infrared Spectroscopy 502

12.3 Infrared Absorption and Chemical Structure 505

12.4 Functional-Group Infrared Absorptions 512

12.5 The Infrared Spectrometer 517

12.6 Introduction to Mass Spectrometry 518

Chapter 13 Nuclear Magnetic Resonance Spectroscopy 539

13.1 An Overview of Proton NMR Spectroscopy 539

13.2 Physical Basis of NMR Spectroscopy 542

13.3 The NMR Spectrum: Chemical Shift and Integral 544

13.4 The NMR Spectrum: Spin-Spin Splitting 557

13.5 Complex NMR Spectra 566

13.6 USE of Deuterium in Proton NMR 573

13.7 Characteristic Functional-Group NMR Absorptions 574

13.8 NMR Spectroscopy of Dynamic Systems 581

13.9 Carbon NMR 584

13.10 Solving Structure Problems with Spectroscopy 591

13.11 The NMR Spectrometer 594

13.12 Other uses of NMR 596

Chapter 14 Chemistry of Alkynes 606

14.2 Structure and Bonding In Alkynes 608

14.3 Physical Properties of Alkynes 611

14.4 Introduction to Addition Reac Hons of the Triple Bond 614

14.5 Conversion of Alkynes Into Aldehydes and Ketones 615

14.6 Reduction of Alkynes 620

14.7 Acidity of 1-Alkynes 623

14.8 Organic Synthesis Using Alkynes 627

14.9 Pheromones 628

14.10 Occurrence and use of Alkynes 630

Chapter 15 Dienes, Resonance, and Aromaticity 637

15.1 Structure and Stability of Dienes 638

15.2 Ultraviolet Spectroscopy 642

15.3 The Diels-Alder Reaction 648

15.4 Addition of Hydrogen Halides to Conjugated Dienes 658

15.5 Diene Polymers 664

15.6 Resonance 666

15.7 Introduction to Aromatic Compounds 673

Chapter 16 Chemistry of Benzene and Its Derivatives 694

16.1 Nomenclature of Benzene Derivatives 694

16.2 Physical Properties of Benzene Derivatives 697

16.3 Spectroscopy of Benzene Derivatives 698

16.4 Electrophilic Aromatic Substitution Reactions of Benzene 704

16.5 Electrophilic Aromatic Substitution Reactions of Substituted Benzenes 716

16.6 Hydrogenation of Benzene Derivatives 731

16.7 Source and Industrial use of Aromatic Hydrocarbons 732

Chapter 17 Allylic and Benzylic Reactivity 743

17.1 Reactions Involving Allylic and Benzylic Carbocations 744

17.2 Reactions Involving Allylic and Benzylic Radicals 748

17.3 Reactions Involving Allylic and Benzylic Anions 753

17.4 Allylic and Benzylic S[subscript N]2 Reactions 757

17.5 Benzylic Oxidation of Alkylbenzenes 758

17.6 Terpenes 759

Chapter 18 Chemistry of Aryl Halides, Vinylic Halides, and Phenols: Transition-Metal Catalysis 775

18.1 Lack of Reactivity of Vinylic and Aryl Halides Under S[subscript N]2 Conditions 776

18.2 Elimination Reactions of Vinylic Halides 778

18.3 Lack of Reactivity of Vinylic and Aryl Halides Under S[subscript N]1 Conditions 779

18.4 Nucleophilic Substitution Reactions of Aryl Halides 781

18.5 Transition-Metal Catalyzed Coupling Reactions 788

18.6 Acidity of Phenols 807

18.7 Oxidation of Phenols to Quinones 811

18.8 Electrophilic Aromatic Substitution Reactions of Phenols 815

18.9 Reactivity of the Aryl-Oxygen Bond 819

18.10 Industrial Preparation and use of Phenol 823

Chapter 19 Chemistry of Aldehydes and Ketones: Carbonyl-Addition Reactions 836

19.2 Physical Properties of Aldehydes and Ketones 842

19.3 Spectroscopy of Aldehydes and Ketones 843

19.4 Synthesis of Aldehydes and Ketones 851

19.5 Introduction to Aldehyde and Ketone Reactions 851

19.6 Basicity of Aldehydes and Ketones 852

19.7 Reversible Addition Reactions of Aldehydes and Ketones 855

19.8 Reduction of Aldehydes and Ketones to Alcohols 861

19.9 Reactions of Aldehydes and Ketones with Grignard and Related Reagents 865

19.10 Acetals and Their use as Protecting Groups 868

19.11 Reactions of Aldehydes and Ketones with Amines 874

19.12 Reduction of Carbonyl Groups to Methylene Groups 879

19.13 The Wittig Alkene Synthesis 881

19.14 Oxidation of Aldehydes to Carboxylic Acids 884

19.15 Manufacture and use of Aldehydes and Ketones 886

Chapter 20 Chemistry of Carboxylic Acids 895

20.2 Structure and Physical Properties of Carboxylic Acids 900

20.3 Spectroscopy of Carboxylic Acids 902

20.4 Acid-Base Properties of Carboxylic Acids 904

20.5 Fatty Acids, Soaps, and Detergents 908

20.6 Synthesis of Carboxylic Acids 910

20.7 Introduction to Carboxylic Acid Reactions 911

20.8 Conversion of Carboxylic Acids into Esters 913

20.9 Conversion of Carboxylic Acids into Acid Chlorides and Anhydrides 918

20.10 Reduction of Carboxylic Acids to Primary Alcohols 922

20.11 Decarboxylation of Carboxylic Acids 923

Chapter 21 Chemistry of Carboxylic Acid Derivatives 934

21.1 Nomenclature and Classification of Carboxylic Acid Derivatives 934

21.2 Structures of Carboxylic Acid Derivatives 940

21.3 Physical Properties of Carboxylic Acid Derivatives 942

21.4 Spectroscopy of Carboxylic Acid Derivatives 944

21.5 Basicity of Carboxylic Acid Derivatives 949

21.6 Introduction to Reactions of Carboxylic Acid Derivatives 950

21.7 Hydrolysis of Carboxylic Acid Derivatives 951

21.8 Reactions of Carboxylic Acid Derivatives with Nucleophiles 963

21.9 Reduction of Carboxylic Acid Derivatives 969

21.10 Reactions of Carboxylic Acid Derivatives with Organometallic Reagents 977

21.11 Synthesis of Carboxylic Acid Derivatives 980

21.12 Use and Occurrence of Carboxylic Acids and Their Derivatives 982

Chapter 22 Chemistry of Enolate Ions, Enols, and [alpha],[beta]-Unsaturated Carbonyl Compounds 997

22.1 Acidity of Carbonyl compounds 998

22.2 Enolization of Carbonyl Compounds 1003

22.3 [alpha]-Halogenation of Carbonyl Compounds 1007

22.4 Aldol Addition and Aldol Condensation 1014

22.5 Condensation Reactions Involving Ester Enolate Ions 1023

22.6 Biosynthesis of Fatty Acids 1032

22.7 Alkylation of Ester Enolate Ions 1035

22.8 Conjugate-Addition Reactions 1043

22.9 Reduction of [alpha],[beta]-Unsaturated Carbonyl Compounds 1052

22.10 Reactions of [alpha],[beta]-Unsaturated Carbonyl Compounds with Organometallic Reagents 1053

22.11 Organic Synthesis with Conjugate-Addition Reactions 1055

Chapter 23 Chemistry of Amines 1069

23.2 Structure of Amines 1072

23.3 Physical Properties of Amines 1073

23.4 Spectroscopy of Amines 1074

23.5 Basicity and Acidity of Amines 1076

23.6 Quaternary Ammonium Salts 1083

23.7 Alkylation and Acylation Reactions of Amines 1083

23.8 Hofmann Elimination of Quaternary Ammonium Hydroxides 1088

23.9 Aromatic Substitution Reactions of Aniline Derivatives 1092

23.10 Diazotization: Reactions of Diazonium Ions 1094

23.11 Synthesis of Amines 1100

23.12 Use and Occurrence of Amines 1108

Chapter 24 Chemistry of Naphthalene and the Aromatic Heterocycles 1120

24.3 Chemistry of Furan, Pyrrole, and Thiophene 1135

24.4 Synthesis of Indoles 1140

24.5 Chemistry of Pyridine and Quinoline 1144

24.6 Occurrence of Heterocyclic Compounds 1161

Chapter 25 Pericyclic Reactions 1172

25.1 Molecular Orbitals of Conjugated [pi]-Electron Systems 1175

25.2 Electrocyclic Reactions 1183

25.3 Cycloaddition Reactions 1183

25.4 Sigmatropic Reactions 1192

25.5 Summary of the Pericyclic Selection Rules 1203

25.6 Fluxional Molecules 1204

25.7 Formation of Vitamin D 1205

Chapter 26 Amino Acids, Peptides, and Proteins 1215

26.1 Nomenclature of Amino Acids and Peptides 1216

26.2 Stereochemistry of the [alpha]-Amino Acids 1220

26.3 Acid-Base Properties of Amino Acids and Peptides 1221

26.4 Synthesis and Enantiomeric Resolution of [alpha]-Amino Acids 1229

26.5 Acylation and Esterification Reactions of Amino Acids 1232

26.6 Determination of Peptide Structure 1233

26.7 Solid-Phase Peptide Synthesis 1246

26.8 Combinatorial Chemistry 1255

26.9 Structures of Peptides and Proteins 1261

26.10 Enzymes: Biological Catalysts 1270

26.11 Occurrence of Peptides and Proteins 1279

Chapter 27 Carbohydrates and Nucleic Acids 1291

27.1 Classification and Properties of Carbohydrates 1292

27.2 Structures of the Monosaccharides 1293

27.3 Mutarotation of Carbohydrates 1302

27.4 Base-Catalyzed Isomerization of Aldoses and Ketoses 1306

27.5 Glycosides 1308

27.6 Ether and Ester Derivatives of Carbohydrates 1311

27.7 Oxidation and Reduction Reactions of Carbohydrates 1314

27.8 Kiliani-Fischer Synthesis 1319

27.9 Proof of Glucose Stereochemistry 1320

27.10 Disaccharides and Polysaccharides 1326

27.11 Nucleosides, Nucleotides, and Nucleic Acids 1333

27.12 DNA, RNA, and the Genetic Code 1341

Appendix I Substitutive Nomenclature of Organic Compounds 1

Appendix II Infrared Absorptions of Organic Compounds 2

Appendix III Proton NMR Chemical Shifts in Organic Compounds 5

Appendix IV [superscript 13]C NMR Chemical Shifts in Organic Compounds 7

Appendix V Summary of Synthetic Methods 8

Appendix VI Reactions Used to Form Carbon-Carbon Bonds 13

Appendix VII Typical Acidities and Basicities of Organic Functional Groups 14.

Notes:

Includes index.

Local Notes:

Acquired for the Penn Libraries with assistance from the Class of 1932 Fund.

ISBN:

0195119991

OCLC:

47746385