Organic Chemistry, 3rd Edition PDF by David R. Klein

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Organic Chemistry, 3rd Edition
by David R. Klein
Organic Chemistry, 3rd Edition
Contents
1
A Review of General Chemistry:
Electrons, Bonds, and Molecular
Properties 1
1.1 Introduction to Organic Chemistry 2
1.2 The Structural Theory of Matter 3
1.3 Electrons, Bonds, and Lewis Structures 4
1.4 Identifying Formal Charges 8
1.5 Induction and Polar Covalent Bonds 9
PRACTICALLY SPEAKING Electrostatic Potential
Maps 12
1.6 Atomic Orbitals 12
1.7 Valence Bond Theory 16
1.8 Molecular Orbital Theory 17
1.9 Hybridized Atomic Orbitals 18
1.10 Predicting Molecular Geometry: VSEPR Theory 24
1.11 Dipole Moments and Molecular Polarity 28
1.12 Intermolecular Forces and Physical Properties 32
PRACTICALLY SPEAKING Biomimicry and
Gecko Feet 35
MEDICALLY SPEAKING Drug-Receptor Interactions 38
1.13 Solubility 38
MEDICALLY SPEAKING Propofol: The Importance of
Drug Solubility 40
Review of Concepts & Vocabulary • SkillBuilder Review
Practice Problems • Integrated Problems • Challenge Problems
 
2
Molecular Representations 49
2.1 Molecular Representations 50
2.2 Bond-Line Structures 51
2.3 Identifying Functional Groups 55
MEDICALLY SPEAKING Marine Natural Products 57
2.4 Carbon Atoms with Formal Charges 58
2.5 Identifying Lone Pairs 58
2.6 Three-Dimensional Bond-Line Structures 61
MEDICALLY SPEAKING Identifying the
Pharmacophore 62
2.7 Introduction to Resonance 63
2.8 Curved Arrows 65
2.9 Formal Charges in Resonance Structures 68
2.10 Drawing Resonance Structures via Pattern
Recognition 70
2.11 Assessing the Relative Importance of Resonance
Structures 75
2.12 The Resonance Hybrid 79
2.13 Delocalized and Localized Lone Pairs 81
Review of Concepts & Vocabulary • SkillBuilder Review
Practice Problems • Integrated Problems • Challenge Problems
 
3
Acids and Bases 93
3.1 Introduction to Brønsted-Lowry Acids
and Bases 94
3.2 Flow of Electron Density: Curved-Arrow
Notation 94
MEDICALLY SPEAKING Antacids and Heartburn 96
3.3 Brønsted-Lowry Acidity: A Quantitative
Perspective 97
MEDICALLY SPEAKING Drug Distribution and pKa 103
3.4 Brønsted-Lowry Acidity: Qualitative
Perspective 104
3.5 Position of Equilibrium and Choice
of Reagents 116
3.6 Leveling Effect 119
3.7 Solvating Effects 120
3.8 Counterions 120
PRACTICALLY SPEAKING Baking Soda versus
Baking Powder 121
3.9 Lewis Acids and Bases 121
Review of Concepts & Vocabulary • SkillBuilder Review
Practice Problems • Integrated Problems • Challenge Problems
4
Alkanes and Cycloalkanes 132
4.1 Introduction to Alkanes 133
4.2 Nomenclature of Alkanes 133
PRACTICALLY SPEAKING Pheromones:
Chemical Messengers 137
MEDICALLY SPEAKING Naming Drugs 145
4.3 Constitutional Isomers of Alkanes 146
4.4 Relative Stability of Isomeric Alkanes 147
4.5 Sources and Uses of Alkanes 148
PRACTICALLY SPEAKING An Introduction
to Polymers 150
4.6 Drawing Newman Projections 150
4.7 Conformational Analysis of Ethane
and Propane 152
4.8 Conformational Analysis of Butane 154
MEDICALLY SPEAKING Drugs and Their
Conformations 158
4.9 Cycloalkanes 158
MEDICALLY SPEAKING Cyclopropane as an
Inhalation Anesthetic 160
4.10 Conformations of Cyclohexane 161
4.11 Drawing Chair Conformations 162
4.12 Monosubstituted Cyclohexane 164
4.13 Disubstituted Cyclohexane 166
4.14 cis-trans Stereoisomerism 170
4.15 Polycyclic Systems 171
Review of Concepts & Vocabulary • SkillBuilder Review
Practice Problems • Integrated Problems • Challenge Problems
5
Stereoisomerism 181
5.1 Overview of Isomerism 182
5.2 Introduction to Stereoisomerism 183
PRACTICALLY SPEAKING The Sense of Smell 188
5.3 Designating Configuration Using the
Cahn-Ingold-Prelog System 188
MEDICALLY SPEAKING Chiral Drugs 193
5.4 Optical Activity 194
5.5 Stereoisomeric Relationships: Enantiomers and
Diastereomers 200
5.6 Symmetry and Chirality 203
5.7 Fischer Projections 207
5.8 Conformationally Mobile Systems 209
5.9 Chiral Compounds That Lack a
Chiral Center 210
5.10 Resolution of Enantiomers 211
5.11 E and Z Designations for Diastereomeric
Alkenes 213
MEDICALLY SPEAKING Phototherapy Treatment for
Neonatal Jaundice 215
Review of Concepts & Vocabulary • SkillBuilder Review
Practice Problems • Integrated Problems • Challenge Problems
6
Chemical Reactivity and Mechanisms 226
6.1 Enthalpy 227
6.2 Entropy 230
6.3 Gibbs Free Energy 232
PRACTICALLY SPEAKING Explosives 233
PRACTICALLY SPEAKING Do Living Organisms Violate
the Second Law of Thermodynamics? 235
6.4 Equilibria 235
6.5 Kinetics 237
MEDICALLY SPEAKING Nitroglycerin: An Explosive
with Medicinal Properties 240
PRACTICALLY SPEAKING Beer Making 241
6.6 Reading Energy Diagrams 242
6.7 Nucleophiles and Electrophiles 245
6.8 Mechanisms and Arrow Pushing 248
6.9 Combining the Patterns of Arrow Pushing 253
6.10 Drawing Curved Arrows 255
6.11 Carbocation Rearrangements 257
6.12 Reversible and Irreversible Reaction Arrows 259
Review of Concepts & Vocabulary • SkillBuilder Review
Practice Problems • Integrated Problems • Challenge Problems
7
Alkyl Halides: Nucleophilic Substitution
and Elimination Reactions 271
7.1 Introduction to Substitution and Elimination
Reactions 272
7.2 Nomenclature and Uses of Alkyl Halides 273
7.3 SN2 Reactions 276
MEDICALLY SPEAKING Pharmacology and Drug
Design 283
7.4 Nucleophilic Strength and Solvent Effects in
SN2 Reactions 285
7.5 SN2 Reactions in Biological Systems—Methylation 287
7.6 Introduction to E2 Reactions 289
7.7 Nomenclature and Stability of Alkenes 291
7.8 Regiochemical and Stereochemical Outcomes for E2
Reactions 295
7.9 Unimolecular Reactions: (SN1 and E1) 305
7.10 Kinetic Isotope Effects in Elimination Reactions 315
7.11 Predicting Products: Substitution vs. Elimination 317
7.12 Substitution and Elimination Reactions with Other
Substrates 323
7.13 Synthesis Strategies 327
MEDICALLY SPEAKING Radiolabeled Compounds in
Diagnostic Medicine 330
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
8
Addition Reactions of Alkenes 343
8.1 Introduction to Addition Reactions 344
8.2 Alkenes in Nature and in Industry 345
PRACTICALLY SPEAKING Pheromones to Control
Insect Populations 345
8.3 Addition vs. Elimination: A Thermodynamic
Perspective 346
8.4 Hydrohalogenation 348
PRACTICALLY SPEAKING Cationic Polymerization
and Polystyrene 355
8.5 Acid-Catalyzed Hydration 356
8.6 Oxymercuration-Demercuration 360
8.7 Hydroboration-Oxidation 361
8.8 Catalytic Hydrogenation 367
PRACTICALLY SPEAKING Partially Hydrogenated
Fats and Oils 372
8.9 Halogenation and Halohydrin Formation 373
8.10 Anti Dihydroxylation 377
8.11 Syn Dihydroxylation 380
8.12 Oxidative Cleavage 381
8.13 Predicting the Products of an Addition
Reaction 383
8.14 Synthesis Strategies 385
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
9
Alkynes 400
9.1 Introduction to Alkynes 401
MEDICALLY SPEAKING The Role of Molecular
Rigidity 403
PRACTICALLY SPEAKING Conducting Organic
Polymers 404
9.2 Nomenclature of Alkynes 404
9.3 Acidity of Acetylene and Terminal
Alkynes 406
9.4 Preparation of Alkynes 409
9.5 Reduction of Alkynes 411
9.6 Hydrohalogenation of Alkynes 414
9.7 Hydration of Alkynes 416
9.8 Halogenation of Alkynes 422
9.9 Ozonolysis of Alkynes 422
9.10 Alkylation of Terminal Alkynes 423
9.11 Synthesis Strategies 425
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
10
Radical Reactions 435
10.1 Radicals 436
10.2 Common Patterns in Radical
Mechanisms 441
10.3 Chlorination of Methane 444
10.4 Thermodynamic Considerations
for Halogenation Reactions 448
10.5 Selectivity of Halogenation 450
10.6 Stereochemistry of Halogenation 453
10.7 Allylic Bromination 455
10.8 Atmospheric Chemistry and the
Ozone Layer 458
PRACTICALLY SPEAKING Fighting Fires with
Chemicals 460
10.9 Autooxidation and Antioxidants 461
MEDICALLY SPEAKING Why Is an Overdose of
Acetaminophen Fatal? 463
10.10 Radical Addition of HBr: Anti-Markovnikov
Addition 464
10.11 Radical Polymerization 468
10.12 Radical Processes in the Petrochemical
Industry 470
10.13 Halogenation as a Synthetic
Technique 470
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
11
Synthesis 479
11.1 One-Step Syntheses 480
11.2 Functional Group Transformations 481
11.3 Reactions That Change the Carbon
Skeleton 484
MEDICALLY SPEAKING Vitamins 486
11.4 How to Approach a Synthesis Problem 487
MEDICALLY SPEAKING The Total Synthesis of
Vitamin B12 489
11.5 Retrosynthetic Analysis 491
PRACTICALLY SPEAKING Retrosynthetic
Analysis 496
11.6 Green Chemistry 496
11.7 Practical Tips for Increasing Proficiency 497
MEDICALLY SPEAKING Total Synthesis of
Taxol 498
Review of Concepts & Vocabulary • SkillBuilder Review
Practice Problems • Integrated Problems
Challenge Problems
12
Alcohols and Phenols 505
12.1 Structure and Properties of Alcohols 506
MEDICALLY SPEAKING Chain Length as a Factor
in Drug Design 510
12.2 Acidity of Alcohols and Phenols 510
12.3 Preparation of Alcohols via Substitution or
Addition 514
12.4 Preparation of Alcohols via Reduction 515
12.5 Preparation of Diols 521
PRACTICALLY SPEAKING Antifreeze 522
12.6 Preparation of Alcohols via Grignard
Reagents 522
12.7 Protection of Alcohols 526
12.8 Preparation of Phenols 527
12.9 Reactions of Alcohols: Substitution and
Elimination 528
PRACTICALLY SPEAKING Drug Metabolism 531
12.10 Reactions of Alcohols: Oxidation 533
12.11 Biological Redox Reactions 537
PRACTICALLY SPEAKING Biological Oxidation
of Methanol and Ethanol 539
12.12 Oxidation of Phenol 539
12.13 Synthesis Strategies 541
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
13
Ethers and Epoxides; Thiols and
Sulfides 556
13.1 Introduction to Ethers 557
13.2 Nomenclature of Ethers 557
13.3 Structure and Properties of Ethers 559
MEDICALLY SPEAKING Ethers as Inhalation
Anesthetics 560
13.4 Crown Ethers 561
MEDICALLY SPEAKING Polyether Antibiotics 563
13.5 Preparation of Ethers 563
13.6 Reactions of Ethers 566
13.7 Nomenclature of Epoxides 569
MEDICALLY SPEAKING Epothilones as Novel
Anticancer Agents 570
13.8 Preparation of Epoxides 570
MEDICALLY SPEAKING Active Metabolites
and Drug Interactions 573
13.9 Enantioselective Epoxidation 573
13.10 Ring-Opening Reactions of Epoxides 575
PRACTICALLY SPEAKING Ethylene Oxide as a Sterilizing
Agent for Sensitive Medical Equipment 578
MEDICALLY SPEAKING Cigarette Smoke
and Carcinogenic Epoxides 582
13.11 Thiols and Sulfides 583
13.12 Synthesis Strategies Involving Epoxides 586
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
14
Infrared Spectroscopy
and Mass Spectrometry 602
14.1 Introduction to Spectroscopy 603
PRACTICALLY SPEAKING Microwave Ovens 605
14.2 IR Spectroscopy 605
MEDICALLY SPEAKING IR Thermal Imaging for
Cancer Detection 606
14.3 Signal Characteristics: Wavenumber 607
14.4 Signal Characteristics: Intensity 612
PRACTICALLY SPEAKING IR Spectroscopy for Testing
Blood Alcohol Levels 614
14.5 Signal Characteristics: Shape 614
14.6 Analyzing an IR Spectrum 618
14.7 Using IR Spectroscopy to Distinguish between
Two Compounds 623
14.8 Introduction to Mass Spectrometry 624
PRACTICALLY SPEAKING Mass Spectrometry
for Detecting Explosives 626
14.9 Analyzing the (M)+• Peak 627
14.10 Analyzing the (M+1)+• Peak 628
14.11 Analyzing the (M+2)+• Peak 630
14.12 Analyzing the Fragments 631
14.13 High-Resolution Mass Spectrometry 634
14.14 Gas Chromatography–Mass Spectrometry 636
14.15 Mass Spectrometry of Large Biomolecules 637
MEDICALLY SPEAKING Medical Applications of
Mass Spectrometry 637
14.16 Hydrogen Deficiency Index: Degrees of
Unsaturation 638
Review of Concepts & Vocabulary • SkillBuilder Review
Practice Problems • Integrated Problems • Challenge Problems
15
Nuclear Magnetic Resonance
Spectroscopy 649
15.1 Introduction to NMR Spectroscopy 650
15.2 Acquiring a 1H NMR Spectrum 652
15.3 Characteristics of a 1H NMR Spectrum 653
15.4 Number of Signals 654
15.5 Chemical Shift 660
15.6 Integration 667
15.7 Multiplicity 670
15.8 Drawing the Expected 1H NMR Spectrum of a
Compound 678
15.9 Using 1H NMR Spectroscopy to Distinguish between
Compounds 679
MEDICALLY SPEAKING Detection of Impurities in
Heparin Sodium Using 1H NMR Spectroscopy 681
15.10 Analyzing a 1H NMR Spectrum 682
15.11 Acquiring a 13C NMR Spectrum 685
15.12 Chemical Shifts in 13C NMR Spectroscopy 685
15.13 DEPT 13C NMR Spectroscopy 687
MEDICALLY SPEAKING Magnetic Resonance
Imaging (MRI) 690
Review of Concepts & Vocabulary • SkillBuilder Review
Practice Problems • Integrated Problems • Challenge Problems
16
Conjugated Pi Systems
and Pericyclic Reactions 701
16.1 Classes of Dienes 702
16.2 Conjugated Dienes 703
16.3 Molecular Orbital Theory 705
16.4 Electrophilic Addition 709
16.5 Thermodynamic Control vs. Kinetic
Control 712
PRACTICALLY SPEAKING Natural and Synthetic
Rubbers 715
16.6 An Introduction to Pericyclic Reactions 716
16.7 Diels–Alder Reactions 717
16.8 MO Description of Cycloadditions 723
16.9 Electrocyclic Reactions 726
16.10 Sigmatropic Rearrangements 731
MEDICALLY SPEAKING The Photoinduced
Biosynthesis of Vitamin D 733
16.11 UV-Vis Spectroscopy 734
PRACTICALLY SPEAKING Sunscreens 738
16.12 Color 739
PRACTICALLY SPEAKING Bleach 740
16.13 Chemistry of Vision 740
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
17
Aromatic Compounds 751
17.1 Introduction to Aromatic Compounds 752
PRACTICALLY SPEAKING What Is Coal? 753
17.2 Nomenclature of Benzene Derivatives 753
17.3 Structure of Benzene 756
17.4 Stability of Benzene 757
PRACTICALLY SPEAKING Molecular Cages 761
17.5 Aromatic Compounds Other Than
Benzene 764
MEDICALLY SPEAKING The Development of
Nonsedating Antihistamines 769
17.6 Reactions at the Benzylic Position 771
17.7 Reduction of Benzene and Its
Derivatives 776
17.8 Spectroscopy of Aromatic Compounds 778
PRACTICALLY SPEAKING Buckyballs and
Nanotubes 781
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
18
Aromatic Substitution Reactions 790
18.1 Introduction to Electrophilic Aromatic
Substitution 791
18.2 Halogenation 791
MEDICALLY SPEAKING Halogenation
in Drug Design 794
18.3 Sulfonation 795
PRACTICALLY SPEAKING What Are Those Colors
in Fruity Pebbles? 796
18.4 Nitration 797
MEDICALLY SPEAKING The Discovery of
Prodrugs 799
18.5 Friedel–Crafts Alkylation 800
18.6 Friedel–Crafts Acylation 802
18.7 Activating Groups 804
18.8 Deactivating Groups 808
18.9 Halogens: The Exception 810
18.10 Determining the Directing Effects of a
Substituent 812
18.11 Multiple Substituents 815
18.12 Synthesis Strategies 821
18.13 Nucleophilic Aromatic Substitution 827
18.14 Elimination-Addition 829
18.15 Identifying the Mechanism of an Aromatic
Substitution Reaction 831
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
19
Aldehydes and Ketones 844
19.1 Introduction to Aldehydes and Ketones 845
19.2 Nomenclature 846
19.3 Preparing Aldehydes and Ketones: A Review 848
19.4 Introduction to Nucleophilic Addition Reactions 849
19.5 Oxygen Nucleophiles 852
MEDICALLY SPEAKING Acetals as Prodrugs 858
19.6 Nitrogen Nucleophiles 860
PRACTICALLY SPEAKING Beta-Carotene and
Vision 864
19.7 Hydrolysis of Acetals, Imines, and Enamines 868
MEDICALLY SPEAKING Prodrugs 871
19.8 Sulfur Nucleophiles 871
19.9 Hydrogen Nucleophiles 872
19.10 Carbon Nucleophiles 873
PRACTICALLY SPEAKING Organic Cyanide Compounds
in Nature 876
19.11 Baeyer–Villiger Oxidation of Aldehydes and
Ketones 881
19.12 Synthesis Strategies 882
19.13 Spectroscopic Analysis of Aldehydes and
Ketones 885
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
20
Carboxylic Acids
and Their Derivatives 898
20.1 Introduction to Carboxylic Acids 899
20.2 Nomenclature of Carboxylic Acids 899
20.3 Structure and Properties of Carboxylic Acids 901
20.4 Preparation of Carboxylic Acids 904
20.5 Reactions of Carboxylic Acids 905
20.6 Introduction to Carboxylic Acid Derivatives 906
MEDICALLY SPEAKING Sedatives 908
20.7 Reactivity of Carboxylic Acid Derivatives 910
20.8 Preparation and Reactions of Acid Chlorides 917
20.9 Preparation and Reactions of Acid Anhydrides 922
MEDICALLY SPEAKING How Does Aspirin Work? 924
20.10 Preparation of Esters 925
20.11 Reactions of Esters 926
PRACTICALLY SPEAKING How Soap Is Made 927
MEDICALLY SPEAKING Esters as Prodrugs 928
20.12 Preparation and Reactions of Amides 931
PRACTICALLY SPEAKING Polyamides and Polyesters 932
MEDICALLY SPEAKING Beta-Lactam Antibiotics 934
20.13 Preparation and Reactions of Nitriles 935
20.14 Synthesis Strategies 938
20.15 Spectroscopy of Carboxylic Acids and Their
Derivatives 943
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
21
Alpha Carbon Chemistry:
Enols and Enolates 954
21.1 Introduction to Alpha Carbon Chemistry:
Enols and Enolates 955
21.2 Alpha Halogenation of Enols and Enolates 962
21.3 Aldol Reactions 966
PRACTICALLY SPEAKING Muscle Power 969
21.4 Claisen Condensations 976
21.5 Alkylation of the Alpha Position 979
21.6 Conjugate Addition Reactions 986
MEDICALLY SPEAKING Glutathione Conjugation
and Biological Michael Reactions 988
21.7 Synthesis Strategies 992
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
22
Amines 1008
22.1 Introduction to Amines 1009
MEDICALLY SPEAKING Drug Metabolism Studies 1010
22.2 Nomenclature of Amines 1010
22.3 Properties of Amines 1013
MEDICALLY SPEAKING Fortunate Side Effects 1014
PRACTICALLY SPEAKING Chemical Warfare
Among Ants 1018
22.4 Preparation of Amines: A Review 1019
22.5 Preparation of Amines via Substitution
Reactions 1020
22.6 Preparation of Amines via Reductive Amination 1023
22.7 Synthesis Strategies 1025
22.8 Acylation of Amines 1028
22.9 Hofmann Elimination 1029
22.10 Reactions of Amines with Nitrous Acid 1032
22.11 Reactions of Aryl Diazonium Ions 1034
22.12 Nitrogen Heterocycles 1038
MEDICALLY SPEAKING H2-Receptor Antagonists
and the Development of Cimetidine 1039
22.13 Spectroscopy of Amines 1041
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
23
Introduction to Organometallic
Compounds 1054
23.1 General Properties of Organometallic
Compounds 1055
23.2 Organolithium and Organomagnesium
Compounds 1056
23.3 Lithium Dialkyl Cuprates (Gilman Reagents) 1059
23.4 The Simmons–Smith Reaction and Carbenoids 1063
23.5 Stille Coupling 1066
23.6 Suzuki Coupling 1071
23.7 Negishi Coupling 1077
23.8 The Heck Reaction 1082
23.9 Alkene Metathesis 1087
PRACTICALLY SPEAKING Improving Biodiesel
via Alkene Metathesis 1092
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
24
Carbohydrates 1107
24.1 Introduction to Carbohydrates 1108
24.2 Classification of Monosaccharides 1108
24.3 Configuration of Aldoses 1111
24.4 Configuration of Ketoses 1112
24.5 Cyclic Structures of Monosaccharides 1114
24.6 Reactions of Monosaccharides 1121
24.7 Disaccharides 1128
MEDICALLY SPEAKING Lactose Intolerance 1131
PRACTICALLY SPEAKING Artificial Sweeteners 1132
24.8 Polysaccharides 1133
24.9 Amino Sugars 1134
24.10 N-Glycosides 1135
MEDICALLY SPEAKING Aminoglycoside Antibiotics 1136
MEDICALLY SPEAKING Erythromycin Biosynthesis 1139
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
25
Amino Acids, Peptides, and Proteins 1147
25.1 Introduction to Amino Acids, Peptides, and
Proteins 1148
25.2 Structure and Properties of Amino Acids 1149
PRACTICALLY SPEAKING Nutrition and Sources
of Amino Acids 1151
PRACTICALLY SPEAKING Forensic Chemistry
and Fingerprint Detection 1155
25.3 Amino Acid Synthesis 1156
25.4 Structure of Peptides 1160
MEDICALLY SPEAKING Polypeptide
Antibiotics 1165
25.5 Sequencing a Peptide 1166
25.6 Peptide Synthesis 1169
25.7 Protein Structure 1177
MEDICALLY SPEAKING Diseases Caused
by Misfolded Proteins 1180
25.8 Protein Function 1180
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
26
Lipids 1190
26.1 Introduction to Lipids 1191
26.2 Waxes 1192
26.3 Triglycerides 1193
26.4 Reactions of Triglycerides 1196
PRACTICALLY SPEAKING Soaps Versus Synthetic
Detergents 1201
26.5 Phospholipids 1205
MEDICALLY SPEAKING Selectivity of Antifungal
Agents 1207
26.6 Steroids 1208
MEDICALLY SPEAKING Cholesterol
and Heart Disease 1211
MEDICALLY SPEAKING Anabolic Steroids
and Competitive Sports 1214
26.7 Prostaglandins 1214
MEDICALLY SPEAKING NSAIDs and COX-2 Inhibitors 1216
26.8 Terpenes 1217
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
27
Synthetic Polymers 1227
27.1 Introduction to Synthetic Polymers 1228
27.2 Nomenclature of Synthetic Polymers 1229
27.3 Copolymers 1230
27.4 Polymer Classification by Reaction Type 1231
27.5 Polymer Classification by Mode of Assembly 1239
27.6 Polymer Classification by Structure 1241
27.7 Polymer Classification by Properties 1244
PRACTICALLY SPEAKING Safety Glass and Car
Windshields 1245
27.8 Polymer Recycling 1246
Review of Reactions • Review of Concepts & Vocabulary
SkillBuilder Review • Practice Problems
Integrated Problems • Challenge Problems
Appendix A: Nomenclature of Polyfunctional
Compounds A–1
Glossary G–1
Credits CR–1
Index I–1

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