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 |  موضوع: كتاب Organic Chemistry الثلاثاء 14 يوليو 2020, 11:53 pm | |
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Organic Chemistry
Sixth Edition
Janice Gorzynski Smith
University of Hawai'i at Manoa
و المحتوى كما يلي :
Page v
Contents
Preface ?xix
Acknowledgments ?xxv
Prologue ?1
What Is Organic Chemistry? ?1
Some Representative Molecules ?2
Marine Natural Products ?4
buttchi 3 Sha Life/ Shutterstock
Structure and Bonding ?7
The Periodic Table ?8
Bonding ?10
Lewis Structures ?12
Isomers ?17
Exceptions to the Octet Rule ?18
Resonance ?18
Determining Molecular Shape ?24
Drawing Organic Structures
Page vi
Hybridization ?35
Ethane, Ethylene, and Acetylene ?38
Bond Length and Bond Strength ?43
Electronegativity and Bond Polarity ?44
Polarity of Molecules ?46
Oxybenzone—A Representative Organic Molecule ?47
Chapter 1 Review ?49
Key Concepts ?49
Key Skills ?50
Problems ?52
Comstock/PunchStock
Acids and Bases ?59
Br?nsted–Lowry Acids and Bases ?60
Reactions of Br?nsted–Lowry Acids and Bases ?61
Acid Strength and pKa ?64
Predicting the Outcome of Acid–Base Reactions ?64
Factors That Determine Acid Strength ?68
Common Acids and Bases ?78
Aspirin ?79
Lewis Acids and Bases ?80
Chapter 2 Review ?83
Key Concepts ?83
Key Skills ?84
Problems
Introduction to Organic Molecules and Functional
Groups ?93
Functional Groups ?94
An Overview of Functional Groups ?95
Intermolecular Forces ?102
Physical Properties ?105
Application: Vitamins ?112
Application: Soap ?114
Application: The Cell Membrane ?115
Functional Groups and Reactivity ?118
Biomolecules ?119
Chapter 3 Review ?121
Key Concepts ?121
Key Skills ?123
Problems ?124
Narongsak Nagadhana/Shutterstock
Alkanes ?131
Alkanes—An Introduction
Cycloalkanes ?134
An Introduction to Nomenclature ?135
Naming Alkanes ?136
Naming Cycloalkanes ?141
Common Names ?143
Natural Occurrence of Alkanes ?144
Properties of Alkanes ?145
Conformations of Acyclic Alkanes—Ethane ?146
Conformations of Butane ?149
An Introduction to Cycloalkanes ?153
Cyclohexane ?154
Substituted Cycloalkanes ?157
Oxidation of Alkanes ?163
Lipids—Part 1 ?166
Chapter 4 Review ?168
Key Concepts ?168
Key Skills ?170
Problems ?172
George Ostertag/ Alamy Stock Photo
Stereochemistry ?179
Starch and Cellulose ?180
The Two Major Classes of Isomers ?182
Looking Glass Chemistry—Chiral and Achiral Molecules ?183
Stereogenic Centers ?186
Stereogenic Centers in Cyclic Compounds ?189
Labeling Stereogenic Centers with R or S ?192
Disastereomers ?197
Meso Compounds
R and S Assignments in Compounds with Two or Page vii
More Stereogenic Centers ?201
Disubstituted Cycloalkanes ?202
Isomers—A Summary ?203
Physical Properties of Stereoisomers ?204
Chemical Properties of Enantiomers ?209
Chapter 5 Review ?211
Key Concepts ?211
Key Skills ?213
Problems ?215
Ninikas/Getty Images
Understanding Organic Reactions ?222
Writing Equations for Organic Reactions ?223
Kinds of Organic Reactions ?224
Bond Breaking and Bond Making ?226
Bond Dissociation Energy ?230
Thermodynamics ?234
Enthalpy and Entropy ?236
Energy Diagrams ?238
Energy Diagram for a Two-Step Reaction Mechanism ?240
Kinetics ?242
Catalysts ?245
Enzymes ?246
Chapter 6 Review ?247
Key Concepts ?247
Key Equations ?248
Key Skills ?248
Problems
Page viii
Source: Claire Fackler, CINMS/NOAA
Alkyl Halides and Nucleophilic Substitution ?256
Introduction to Alkyl Halides ?257
Nomenclature ?258
Properties of Alkyl Halides ?259
Interesting Alkyl Halides ?260
The Polar Carbon–Halogen Bond ?262
General Features of Nucleophilic Substitution ?263
The Leaving Group ?264
The Nucleophile ?266
Possible Mechanisms for Nucleophilic Substitution ?270
Two Mechanisms for Nucleophilic Substitution ?271
The SN2 Mechanism ?272
The SN1 Mechanism ?277
Carbocation Stability ?282
The Hammond Postulate ?283
When Is the Mechanism SN1 or SN2? ?286
Biological Nucleophilic Substitution ?292
Vinyl Halides and Aryl Halides ?295
Organic Synthesis ?295
Chapter 7 Review ?297
Key Concepts ?297
Key Skills ?299
Key Mechanism Concepts ?300
Problems
Forest & Kim Starr
Alkyl Halides and Elimination Reactions ?308
General Features of Elimination ?309
Alkenes—The Products of Elimination Reactions ?310
The Mechanisms of Elimination ?314
The E2 Mechanism ?314
The Zaitsev Rule ?318
The E1 Mechanism ?320
SN1 and E1 Reactions ?323
Stereochemistry of the E2 Reaction ?324
When Is the Mechanism E1 or E2? ?328
E2 Reactions and Alkyne Synthesis ?328
When Is the Reaction SN1, SN2, E1, or E2? ?330
Chapter 8 Review ?334
Key Concepts ?334
Key Skills ?335
Key Mechanism Concepts ?337
Problems ?338
Daniel C. Smith
9.18 Page ix
Alcohols, Ethers, and Related Compounds ?345
Introduction ?346
Structure and Bonding ?347
Nomenclature ?348
Properties of Alcohols, Ethers, and Epoxides ?351
Interesting Alcohols, Ethers, and Epoxides ?352
Preparation of Alcohols, Ethers, and Epoxides ?355
General Features—Reactions of Alcohols, Ethers, and
Epoxides ?357
Dehydration of Alcohols to Alkenes ?359
Carbocation Rearrangements ?362
Dehydration Using POCl3 and Pyridine ?364
Conversion of Alcohols to Alkyl Halides with HX ?365
Conversion of Alcohols to Alkyl Halides with SOCl2 and PBr3
Tosylate—Another Good Leaving Group ?372
Reaction of Ethers with Strong Acid ?375
Thiols and Sulfides ?376
Reactions of Epoxides ?379
Application: Epoxides, Leukotrienes, and Asthma ?384
Application: Benzo[a]pyrene, Epoxides, and Cancer ?
Chapter 9 Review ?386
Key Concepts ?386
Key Reactions ?386
Key Skills ?388
Key Mechanism Concepts in Reactions of Alcohols ?390
Problems
Adam Gault/Getty Images
Alkenes and Addition Reactions ?397
Introduction ?398
Calculating Degrees of Unsaturation ?399
Nomenclature ?401
Properties of Alkenes ?405
Interesting Alkenes ?406
Lipids—Part 2 ?407
Preparation of Alkenes ?409
Introduction to Addition Reactions ?410
Hydrohalogenation—Electrophilic Addition of HX ?411
Markovnikov's Rule ?413
Stereochemistry of Electrophilic Addition of HX ?415
Hydration—Electrophilic Addition of Water ?417
Halogenation—Addition of Halogen ?418
Stereochemistry of Halogenation ?419
Halohydrin Formation ?421
Hydroboration–Oxidation ?424
Keeping Track of Reactions ?428
Alkenes in Organic Synthesis ?430
Chapter 10 Review ?432
Key Concepts ?432
Key Reactions ?433
Key Skills ?433
Key Mechanism Concepts ?434
Problems ?435
McGraw-Hill Education/ Chris Kerrigan, photographer
Alkynes and Synthesis
Page x
Introduction ?442
Nomenclature ?443
Properties of Alkynes ?444
Interesting Alkynes ?445
Preparation of Alkynes ?446
Introduction to Alkyne Reactions ?447
Addition of Hydrogen Halides ?449
Addition of Halogen ?451
Addition of Water ?451
Hydroboration–Oxidation ?454
Reaction of Acetylide Anions ?456
Synthesis ?460
Chapter 11 Review ?463
Key Reactions ?463
Key Skills ?463
Problems ?465
Amarita/Shutterstock
Oxidation and Reduction ?472
Introduction ?473
Reducing Agents ?474
Reduction of Alkenes ?475
Application: Hydrogenation of Oils ?478
Reduction of Alkynes ?480
The Reduction of Polar C–X ? Bonds ?483
Oxidizing Agents ?484
Epoxidation ?485
Dihydroxylation
Spectroscopy A
Oxidative Cleavage of Alkenes ?491
Oxidative Cleavage of Alkynes ?493
Oxidation of Alcohols ?494
Green Chemistry ?497
Biological Oxidation ?498
Sharpless Epoxidation ?499
Chapter 12 Review ?502
Key Concepts ?502
Key Reactions ?502
Key Skills ?504
Problems ?505
atomazul/123RF
Mass Spectrometry ?512
Mass Spectrometry and the Molecular Ion ?513
Alkyl Halides and the M + 2 Peak ?518
Fragmentation ?520
Fragmentation Patterns of Some Common Functional Groups
?523
Other Types of Mass Spectrometry ?525
Chapter Review ?528
Key Concepts ?528
Key Skills ?528
Problems ?529Spectroscopy B
Spectroscopy C
Page xi
T.Daly/Alamy Stock Photo
Infrared Spectroscopy ?534
Electromagnetic Radiation ?535
The General Features of Infrared Spectroscopy ?537
IR Absorptions ?539
Infrared Spectra of Common Functional Groups ?546
IR and Structure Determination ?554
Chapter Review ?556
Key Concepts ?556
Key Skills ?557
Problems ?558
Daniel C. Smith
Nuclear Magnetic Resonance Spectroscopy
?562
An Introduction to NMR Spectroscopy ?563
1H NMR: Number of Signals ?566
1H NMR: Position of Signals ?571
The Chemical Shifts of Protons on sp2 and sp Hybridized
Carbons ?575
1H NMR: Intensity of Signals
1H NMR: Spin–Spin Splitting ?578
More-Complex Examples of Splitting ?582
Spin–Spin Splitting in Alkenes ?585
Other Facts About 1H NMR Spectroscopy ?587
Using 1H NMR to Identify an Unknown ?590
13C NMR Spectroscopy ?593
Magnetic Resonance Imaging (MRI) ?597
Chapter Review ?598
Key Concepts ?598
Key Skills ?598
Problems ?602
jeep2499/Shutterstock
Radical Reactions ?611
Introduction ?612
General Features of Radical Reactions ?613
Halogenation of Alkanes ?615
The Mechanism of Halogenation ?616
Chlorination of Other Alkanes ?619
Chlorination Versus Bromination ?619
Halogenation as a Tool in Organic Synthesis ?622
The Stereochemistry of Halogenation Reactions ?623
Application: The Ozone Layer and CFCs ?625
Radical Halogenation at an Allylic Carbon ?627
Application: Oxidation of Unsaturated Lipids ?630
Application: Antioxidants ?631
Radical Addition Reactions to Double Bonds ?632
Polymers and Polymerization
Page xii
Chapter 13 Review ?638
Key Concepts ?638
Key Reactions ?638
Key Skills ?639
Problems ?641
John Foxx/Getty Images
Conjugation, Resonance, and Dienes ?648
Conjugation ?649
Resonance and Allylic Carbocations ?651
Common Examples of Resonance ?653
The Resonance Hybrid ?654
Electron Delocalization, Hybridization, and Geometry ?656
Conjugated Dienes ?657
Interesting Dienes and Polyenes ?659
The Carbon–Carbon ? Bond Length in Buta-1,3-diene ?660
Stability of Conjugated Dienes ?660
Electrophilic Addition: 1,2- Versus 1,4-Addition ?661
Kinetic Versus Thermodynamic Products ?663
The Diels–Alder Reaction ?666
Specific Rules Governing the Diels–Alder Reaction ?668
Other Facts About the Diels–Alder Reaction ?672
Conjugated Dienes and Ultraviolet Light ?675
Chapter 14 Review ?678
Key Concepts ?678
Key Reactions ?679
Key Skills ?679
Problems
Daniel C. Smith
Benzene and Aromatic Compounds ?689
Background ?690
The Structure of Benzene ?691
Nomenclature of Benzene Derivatives ?693
Spectroscopic Properties ?695
Interesting Aromatic Compounds ?696
Benzene's Unusual Stability ?697
The Criteria for Aromaticity—Hückel's Rule ?699
Examples of Aromatic Compounds ?701
What Is the Basis of Hückel's Rule? ?708
The Inscribed Polygon Method for Predicting Aromaticity ?
Buckminsterfullerene—Is It Aromatic? ?713
Chapter 15 Review ?715
Key Concepts ?715
Key Skills ?715
Problems ?717
Jill Braaten
Reactions of Aromatic Compounds
Page xiii
Electrophilic Aromatic Substitution ?726
The General Mechanism ?727
Halogenation ?728
Nitration and Sulfonation ?730
Friedel–Crafts Alkylation and Friedel–Crafts Acylation ?732
Substituted Benzenes ?739
Electrophilic Aromatic Substitution of Substituted Benzenes
?742
Why Substituents Activate or Deactivate a Benzene Ring ?746
Orientation Effects in Substituted Benzenes ?747
Limitations on Electrophilic Substitution Reactions with
Substituted Benzenes ?750
Disubstituted Benzenes ?752
Synthesis of Benzene Derivatives ?754
Nucleophilic Aromatic Substitution ?755
Halogenation of Alkyl Benzenes ?759
Oxidation and Reduction of Substituted Benzenes ?761
Multistep Synthesis ?765
Chapter 16 Review ?767
Key Concepts ?767
Key Reactions ?768
Key Skills ?769
Key Mechanism Concepts ?771
Problems ?772
AS Food studio/Shutterstock
Introduction to Carbonyl Chemistry; Organometallic
Reagents; Oxidation and Reduction ?780
Introduction
General Reactions of Carbonyl Compounds ?782
A Preview of Oxidation and Reduction ?785
Reduction of Aldehydes and Ketones ?787
The Stereochemistry of Carbonyl Reduction ?789
Enantioselective Carbonyl Reductions ?790
Reduction of Carboxylic Acids and Their Derivatives ?793
Oxidation of Aldehydes ?798
Organometallic Reagents ?799
Reaction of Organometallic Reagents with Aldehydes and
Ketones ?802
Retrosynthetic Analysis of Grignard Products ?805
Protecting Groups ?807
Reaction of Organometallic Reagents with Carboxylic Acid
Derivatives ?810
Reaction of Organometallic Reagents with Other Compounds
?,?-Unsaturated Carbonyl Compounds ?815
Summary—The Reactions of Organometallic Reagents ?818
Synthesis ?818
Chapter 17 Review ?821
Key Reactions ?821
Key Skills ?823
Key Mechanism Concepts ?825
Problems ?825
iStock/Getty Images
Aldehydes and Ketones—Nucleophilic Addition ?
Introduction
Page xiv
Nomenclature ?835
Properties of Aldehydes and Ketones ?839
Interesting Aldehydes and Ketones ?841
Preparation of Aldehydes and Ketones ?842
Reactions of Aldehydes and Ketones—General
Considerations ?843
Nucleophilic Addition of H? and R?—A Review ?846
Nucleophilic Addition of ?CN ?848
The Wittig Reaction ?850
Addition of 1° Amines ?855
Addition of 2° Amines ?858
Addition of H2O—Hydration ?861
Addition of Alcohols—Acetal Formation ?863
Acetals as Protecting Groups ?867
Cyclic Hemiacetals ?868
An Introduction to Carbohydrates ?871
Chapter 18 Review ?872
Key Concepts ?872
Key Reactions ?873
Key Skills ?874
Problems ?876
Sarka Babicka/Getty Images
Carboxylic Acids and Nitriles ?885
Structure and Bonding ?886
Nomenclature ?887
Physical and Spectroscopic Properties ?890
Interesting Carboxylic Acids and Nitriles ?892
Aspirin, Arachidonic Acid, and Prostaglandins
Page xv
Preparation of Carboxylic Acids ?894
Carboxylic Acids—Strong Organic Br?nsted–Lowry Acids ?
895
Inductive Effects in Aliphatic Carboxylic Acids ?899
Substituted Benzoic Acids ?901
Extraction ?904
Amino Acids ?907
Nitriles ?911
Chapter 19 Review ?915
Key Concepts ?915
Key Reactions ?916
Key Skills ?916
Problems ?918
LIKIT SUPASAI/Shutterstock
Carboxylic Acids and Their Derivatives—Nucleophilic
Acyl Substitution ?926
Introduction ?927
Structure and Bonding ?929
Nomenclature ?930
Physical and Spectroscopic Properties ?934
Interesting Esters and Amides ?936
Introduction to Nucleophilic Acyl Substitution ?938
Reactions of Acid Chlorides ?941
Reactions of Anhydrides ?943
Reactions of Carboxylic Acids ?945
Reactions of Esters ?950
Application: Lipid Hydrolysis ?952
Reactions of Amides
Application: The Mechanism of Action of ?-Lactam Antibiotics
?956
Summary of Nucleophilic Acyl Substitution Reactions ?957
Natural and Synthetic Fibers ?958
Biological Acylation Reactions ?960
Chapter 20 Review ?962
Key Concepts ?962
Key Reactions ?962
Key Skills ?964
Problems ?964
surachetkhamsuk/ iStock/Getty Images
Substitution Reactions of Carbonyl Compounds at
the ? Carbon ?973
Introduction ?974
Enols ?975
Enolates ?977
Enolates of Unsymmmetrical Carbonyl Compounds ?982
Racemization at the ? Carbon ?984
A Preview of Reactions at the ? Carbon ?985
Halogenation at the ? Carbon ?986
Direct Enolate Alkylation ?990
Malonic Ester Synthesis ?993
Acetoacetic Ester Synthesis ?998
Chapter 21 Review ?1001
Key Reactions ?1001
Key Skills ?1002
Problems
Page xvi
Jill Braaten
Carbonyl Condensation Reactions ?1011
The Aldol Reaction ?1012
Crossed Aldol Reactions ?1016
Directed Aldol Reactions ?1020
Intramolecular Aldol Reactions ?1022
The Claisen Reaction ?1025
The Crossed Claisen and Related Reactions ?1027
The Dieckmann Reaction ?1029
The Michael Reaction ?1030
The Robinson Annulation ?1032
Chapter 22 Review ?1036
Key Reactions ?1036
Key Skills ?1037
Problems ?1038
Daniel C. Smith
Amines ?1047
Introduction ?1048
Structure and Bonding ?1048
Nomenclature
Physical and Spectroscopic Properties ?1052
Interesting and Useful Amines ?1054
Preparation of Amines ?1057
Reactions of Amines—General Features ?1064
Amines as Bases ?1064
Relative Basicity of Amines and Other Compounds ?1066
Amines as Nucleophiles ?1072
Hofmann Elimination ?1074
Reactions of Amines with Nitrous Acid ?1077
Substitution Reactions of Aryl Diazonium Salts ?1079
Coupling Reactions of Aryl Diazonium Salts ?1084
Application: Synthetic Dyes and Sulfa Drugs ?1085
Chapter 23 Review ?1088
Key Concepts ?1088
Key Reactions ?1089
Key Skills ?1091
Problems ?1093
DEA/M. Giovanoli/Getty Images
Carbon–Carbon Bond-Forming Reactions in Organic
Synthesis ?1102
Coupling Reactions of Organocuprate Reagents ?1103
Suzuki Reaction ?1105
Heck Reaction ?1110
Carbenes and Cyclopropane Synthesis ?1112
Simmons–Smith Reaction ?1115
Metathesis ?1116
Chapter 24 Review ?1121
Key Reactions
Page xvii
Key Skills ?1122
Problems ?1123
Nature Picture Library/Alamy Stock Photo
Pericyclic Reactions ?1131
Types of Pericyclic Reactions ?1132
Molecular Orbitals ?1133
Electrocyclic Reactions ?1136
Cycloaddition Reactions ?1142
Sigmatropic Rearrangements ?1146
Summary of Rules for Pericyclic Reactions ?1152
Chapter 25 Review ?1153
Key Concepts ?1153
Key Reactions ?1153
Key Skills ?1154
Problems ?1155
MaraZe/Shutterstock
Carbohydrates ?1162
Introduction ?1163
Monosaccharides ?1164
The Family of D-Aldoses
The Family of D-Ketoses ?1171
Physical Properties of Monosaccharides ?1172
The Cyclic Forms of Monosaccharides ?1172
Glycosides ?1180
Reactions of Monosaccharides at the OH Groups ?1183
Reactions at the Carbonyl Group—Oxidation and Reduction ?
1184
Reactions at the Carbonyl Group—Adding or Removing One
Carbon Atom ?1187
Disaccharides ?1191
Polysaccharides ?1193
Other Important Sugars and Their Derivatives ?1196
Chapter 26 Review ?1201
Key Reactions ?1201
Key Skills ?1203
Problems ?1206
Daniel C. Smith
Amino Acids and Proteins ?1212
Amino Acids ?1213
Synthesis of Amino Acids ?1217
Separation of Amino Acids ?1220
Enantioselective Synthesis of Amino Acids ?1223
Peptides ?1225
Peptide Sequencing ?1229
Peptide Synthesis ?1232
Automated Peptide Synthesis ?1237
Protein Structure ?1239
Important Proteins
Page xviii
Chapter 27 Review ?1248
Key Reactions ?1248
Key Skills ?1250
Problems ?1253
stuar/Shutterstock
Synthetic Polymers ?1259
Introduction ?1260
Chain-Growth Polymers—Addition Polymers ?1261
Anionic Polymerization of Epoxides ?1268
Ziegler–Natta Catalysts and Polymer Stereochemistry ?1269
Natural and Synthetic Rubbers ?1270
Step-Growth Polymers—Condensation Polymers ?1272
Polymer Structure and Properties ?1276
Green Polymer Synthesis ?1278
Polymer Recycling and Disposal ?1281
Chapter 28 Review ?1284
Key Concepts ?1284
Key Reactions ?1284
Key Skills ?1285
Problems ?1285
Iconotec/Glowimages
Appendix A
Appendix B
Appendix C
Appendix D
Appendix E
Appendix F
Appendix G
Appendix H
Appendix I
Appendix J
Lipids 1292 (Available Online)
Introduction ?1293
Waxes ?1294
Triacylglycerols ?1295
Phospholipids ?1299
Fat-Soluble Vitamins ?1302
Eicosanoids ?1303
Terpenes ?1306
Steroids ?1312
Chapter 29 Review ?1317
Key Concepts ?1317
Key Reactions ?1318
Key Skills ?1319
Problems ?1319
Periodic Table of the Elements ?A
Common Abbreviations, Arrows, and Symbols ?A-1
pKa Values for Selected Compounds ?A-3
Nomenclature ?A-5
Bond Dissociation Energies for Some Common Bonds
[A–B ? A· + ·B] ?A-9
Reactions That Form Carbon–Carbon Bonds ?A-10
Characteristic IR Absorption Frequencies ?A-11
Characteristic NMR Absorptions ?A-12
General Types of Organic Reactions ?A-14
How to Synthesize Particular Functional Groups ?A-16
Glossary ?G
Index
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