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

Online:

The Class of 1932 Fund Home Page