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Organic Chemistry: With Infotrac : Glasses

ISBN: 9780534363550 | 0534363555
Edition: 4th
Format: Paperback
Publisher: Brooks Cole
Pub. Date: 8/3/1998

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Table of Contents
... MORE
Structure and Bonding
1(37)
Atomic Structure
3(1)
Atomic Structure: Orbitals
4(3)
Atomic Structure: Electron Configurations
7(1)
Development of Chemical Bonding Theory
8(1)
The Nature of Chemical Bonding: Ionic Bonds
9(2)
The Nature of Chemical Bonding: Covalent Bonds
11(3)
Describing Covalent Bonds: Valence Bond Theory and Molecular Orbital Theory
14(4)
Hybridization: sp3 Orbitals and the Structure of Methane
18(2)
The Structure of Ethane
20(2)
Hybridization: sp2 Orbitals and the Structure of Ethylene
22(4)
Hybridization: sp Orbitals and the Structure of Acetylene
26(2)
Hybridization of Other Atoms: Nitrogen, Oxygen, and Boron
28(10)
Interlude---Chemical Toxicity and Risk
31(1)
Summary and Key Words
32(1)
Working Problems
33(1)
Additional Problems
33(5)
Bonding and Molecular Properties
38(32)
Polar Covalent Bonds: Electronegativity
38(3)
Polar Covalent Bonds: Dipole Moment
41(2)
Formal Charges
43(3)
Chemical Structures and Resonance
46(1)
Drawing and Interpreting Resonance Forms
47(3)
Acids and Bases: The Brønsted--Lowry Definition
50(3)
Predicting Acid--Base Reactions from pKa Values
53(2)
Acids and Bases: The Lewis Definition
55(4)
Drawing Chemical Structures
59(3)
Molecular Models
62(8)
Interlude---Alkaloids: Naturally Occurring Bases
63(1)
Summary and Key Words
64(1)
Additional Problems
65(5)
The Nature of Organic Compounds: Alkanes and Cycloalkanes
70(36)
Functional Groups
70(5)
Alkanes and Alkane Isomers
75(5)
Alkyl Groups
80(4)
Naming Alkanes
84(6)
Properties of Alkanes
90(2)
Cycloalkanes
92(2)
Naming Cycloalkanes
94(1)
Cis--Trans Isomerism in Cycloalkanes
95(11)
Interlude---Petroleum
99(1)
Summary and Key Words
100(1)
Additional Problems
101(5)
Stereochemistry of Alkanes and Cycloalkanes
106(40)
Conformations of Ethane
106(4)
Conformations of Propane
110(1)
Conformations of Butane
111(4)
Conformation and Stability of Cycloalkanes: The Baeyer Strain Theory
115(1)
Heats of Combustion of Cycloalkanes
116(2)
The Nature of Ring Strain
118(1)
Cyclopropane: An Orbital View
119(2)
Conformations of Cyclobutane and Cyclopentane
121(2)
Conformations of Cyclohexane
123(1)
Axial and Equatorial Bonds in Cyclohexane
124(3)
Conformational Mobility of Cyclohexane
127(2)
Conformations of Monosubstituted Cyclohexanes
129(4)
Conformational Analysis of Disubstituted Cyclohexanes
133(2)
Boat Cyclohexane
135(2)
Conformations of Polycyclic Molecules
137(9)
Interlude---Molecular Mechanics
140(1)
Summary and Key Words
141(1)
Additional Problems
142(4)
An Overview of Organic Reactions
146(32)
Kinds of Organic Reactions
146(2)
How Organic Reactions Occur: Mechanisms
148(1)
Radical Reactions and How They Occur
149(2)
Polar Reactions and How They Occur
151(4)
An Example of a Polar Reaction: Addition of HBr to Ethylene
155(2)
Describing a Reaction: Rates and Equilibria
157(5)
Describing a Reaction: Bond Dissociation Energies
162(2)
Describing a Reaction: Energy Diagrams and Transition States
164(4)
Describing a Reaction: Intermediates
168(10)
Interlude---Explosives
171(1)
Summary and Key Words
172(2)
Additional Problems
174(4)
Alkenes: Structure and Reactivity
178(42)
Industrial Preparation and Use of Alkenes
179(1)
Calculating a Molecule's Degree of Unsaturation
180(3)
Naming Alkenes
183(2)
Electronic Structure of Alkenes
185(2)
Cis--Trans Isomerism in Alkenes
187(2)
Sequence Rules: The E,Z Designation
189(4)
Alkene Stability
193(5)
Alkene Electrophilic Addition Reactions
198(3)
Orientation of Electrophilic Addition: Markovnikov's Rule
201(2)
Carbocation Structure and Stability
203(4)
The Hammond Postulate
207(3)
Mechanistic Evidence: Carbocation Rearrangements
210(10)
Interlude---Carrots, Alkenes, and the Chemistry of Vision
213(1)
Summary and Key Words
214(1)
Additional Problems
215(5)
Alkenes: Reactions and Synthesis
220(44)
Preparation of Alkenes: A Preview of Elimination Reactions
221(1)
Addition of Halogens to Alkenes
222(4)
Halohydrin Formation
226(3)
Hydration of Alkenes: Oxymercuration
229(2)
Hydration of Alkenes: Hydroboration
231(4)
Addition of Carbenes to Alkenes: Cyclopropane Synthesis
235(3)
Reduction of Alkenes: Hydrogenation
238(3)
Oxidation of Alkenes: Hydroxylation and Cleavage
241(3)
Biological Alkene Addition Reactions
244(1)
A Radical Addition to Alkenes: HBr/Peroxides
245(4)
Radical Polymerization of Alkenes: Polyethylene
249(15)
Interlude---Natural Rubber
252(1)
Summary and Key Words
253(1)
Learning Reactions
254(1)
Summary of Reactions
254(3)
Additional Problems
257(7)
Alkynes
264(30)
Electronic Structure of Alkynes
265(1)
Naming Alkynes
266(1)
Preparation of Alkynes: Elimination Reactions of Dihalides
267(1)
Reactions of Alkynes: Addition of HX and X2
268(2)
Hydration of Alkynes
270(3)
Reduction of Alkynes
273(3)
Oxidative Cleavage of Alkynes
276(1)
Alkyne Acidity: Formation of Acetylide Anions
277(2)
Alkylation of Acetylide Anions
279(2)
Organic Synthesis
281(13)
Interlude---Polyynes: A New Form of Carbon
285(1)
Summary and Key Words
286(1)
Summary of Reactions
287(1)
Additional Problems
288(6)
Stereochemistry
294(48)
Enantiomers and the Tetrahedral Carbon
294(3)
The Reason for Handedness in Molecules: Chirality
297(3)
Optical Activity
300(2)
Specific Rotation
302(1)
Pasteur's Discovery of Enantiomers
303(1)
Sequence Rules for Specification of Configuration
304(4)
Diastereomers
308(2)
Meso Compounds
310(2)
Molecules with More Than Two Stereogenic Centers
312(1)
Racemic Mixtures and Their Resolution
313(2)
Physical Properties of Stereoisomers
315(1)
A Brief Review of Isomerism
316(2)
Fischer Projections
318(4)
Assigning R,S Configurations to Fischer Projections
322(1)
Stereochemistry of Reactions: Addition of HBr to Alkenes
323(2)
Stereochemistry of Reactions: Addition of Br2 to Alkenes
325(2)
Stereochemistry of Reactions: Addition of HBr to a Chiral Alkene
327(1)
Stereoisomerism and Chirality in Substituted Cyclohexanes
328(3)
Chirality at Atoms Other Than Carbon
331(1)
Chirality in Nature
332(10)
Interlude---Chiral Drugs
333(2)
Summary and Key Words
335(1)
Additional Problems
335(7)
Alkyl Halides
342(28)
Naming Alkyl Halides
343(2)
Structure of Alkyl Halides
345(1)
Preparation of Alkyl Halides
346(1)
Radical Halogenation of Alkanes
347(4)
Allylic Bromination of Alkenes
351(1)
Stability of the Allyl Radical: Resonance Revisited
352(3)
Preparing Alkyl Halides from Alcohols
355(2)
Reactions of Alkyl Halides: Grignard Reagents
357(2)
Organometallic Coupling Reactions
359(2)
Oxidation and Reduction in Organic Chemistry
361(9)
Interlude---Alkyl Halides and the Ozone Hole
363(1)
Summary and Key Words
364(1)
Summary of Reactions
365(1)
Additional Problems
366(4)
Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
370(54)
The Discovery of the Walden Inversion
371(1)
Stereochemistry of Nucleophilic Substitution
372(2)
Kinetics of Nucleophilic Substitution
374(1)
The SN2 Reaction
375(2)
Characteristics of the SN2 Reaction
377(9)
The SN1 Reaction
386(1)
Kinetics of the SN1 Reaction
386(3)
Stereochemistry of the SN1 Reaction
389(2)
Characteristics of the SN1 Reaction
391(7)
Elimination Reactions of Alkyl Halides
398(1)
The E2 Reaction
399(4)
Elimination Reactions and Cyclohexane Conformation
403(2)
The Deuterium Isotope Effect
405(1)
The E1 Reaction
405(3)
Summary of Reactivity: SN1, SN2, E1, E2
408(2)
Substitution Reactions in Synthesis
410(2)
Substitution Reactions in Biological Systems
412(12)
Interlude---Naturally Occurring Organohalogen Compounds
414(1)
Summary and Key Words
415(1)
Summary of Reactions
416(1)
Additional Problems
417(7)
Structure Determination: Mass Spectrometry and Infrared Spectroscopy
424(30)
Mass Spectrometry
425(2)
Interpreting Mass Spectra
427(2)
Interpreting Mass Spectral Fragmentation Patterns
429(4)
Spectroscopy and the Electromagnetic Spectrum
433(4)
Infrared Spectroscopy of Organic Molecules
437(2)
Interpreting Infrared Spectra
439(4)
Infrared Spectra of Hydrocarbons
443(1)
Infrared Spectra of Other Functional Groups
444(10)
Interlude---Chromatography: Purifying Organic Compounds
446(2)
Summary and Key Words
448(1)
Additional Problems
448(6)
Structure Determination: Nuclear Magnetic Resonance Spectroscopy
454(43)
Nuclear Magnetic Resonance Spectroscopy
455(2)
The Nature of NMR Absorptions
457(4)
Chemical Shifts
461(2)
1H NMR Spectroscopy and Proton Equivalence
463(1)
Chemical Shifts in 1H NMR Spectroscopy
464(3)
Integration of 1H NMR Absorptions: Proton Counting
467(1)
Spin--Spin Splitting in 1H NMR Spectra
468(5)
More Complex Spin--Spin Splitting Patterns
473(3)
Uses of 1H NMR Spectroscopy
476(1)
13C NMR Spectroscopy: Signal Averaging and FT-NMR
477(2)
Characteristics of 13C NMR Spectroscopy
479(3)
DEPT 13C NMR Spectroscopy
482(2)
Uses of 13C NMR Spectroscopy
484(13)
Interlude---Magnetic Resonance Imaging (MRI)
485(1)
Summary and Key Words
486(1)
Additional Problems
487(10)
Conjugated Dienes and Ultraviolet Spectroscopy
497(37)
Preparation of Conjugated Dienes
498(1)
Stability of Conjugated Dienes
499(2)
Molecular Orbital Description of 1,3-Butadiene
501(2)
Bond Lengths in 1,3-Butadiene
503(1)
Electrophilic Additions to Conjugated Dienes: Allylic Carbocations
504(4)
Kinetic Versus Thermodynamic Control of Reactions
508(2)
Diene Polymers: Natural and Synthetic Rubbers
510(2)
The Diels--Alder Cycloaddition Reaction
512(2)
Characteristics of the Diels--Alder Reaction
514(4)
Other Conjugated Systems
518(1)
Structure Determination in Conjugated Systems: Ultraviolet Spectroscopy
519(1)
Ultraviolet Spectrum of 1,3-Butadiene
520(2)
Interpreting Ultraviolet Spectra: The Effect of Conjugation
522(2)
Colored Organic Compounds
524(10)
Interlude---Resists for Integrated Circuits
525(2)
Summary and Key Words
527(1)
Additional Problems
527(7)
Benzene and Aromaticity
534(36)
Sources of Aromatic Hydrocarbons
535(1)
Naming Aromatic Compounds
536(4)
Structure of Benzene: The Kekule Proposal
540(1)
Stability of Benzene
541(2)
Representations of Benzene: The Resonance Approach
543(2)
Molecular Orbital Description of Benzene
545(2)
Aromaticity and the Huckel 4n + 2 Rule
547(2)
Aromatic Ions
549(4)
Pyridine and Pyrrole: Two Aromatic Heterocycles
553(2)
Why 4n + 2?
555(2)
Naphthalene: A Polycyclic Aromatic Compound
557(1)
Spectroscopy of Aromatic Compounds
558(12)
Interlude---Polycyclic Aromatic Hydrocarbons and Cancer
563(1)
Summary and Key Words
564(1)
Additional Problems
565(5)
Chemistry of Benzene: Electrophilic Aromatic Substitution
570(53)
Bromination of Aromatic Rings
571(4)
Other Aromatic Substitutions
575(4)
Alkylation of Aromatic Rings: The Friedel--Crafts Reaction
579(4)
Acylation of Aromatic Rings
583(1)
Substituent Effects in Substituted Aromatic Rings
584(4)
An Explanation of Substituent Effects
588(7)
Trisubstituted Benzenes: Additivity of Effects
595(2)
Nucleophilic Aromatic Substitution
597(3)
Benzyne
600(2)
Oxidation of Aromatic Compounds
602(3)
Reduction of Aromatic Compounds
605(2)
Synthesis of Substituted Benzenes
607(16)
Interlude---Aspirin and Other Aromatic NSAIDs
611(1)
Summary and Key Words
612(1)
Summary of Reactions
613(3)
Additional Problems
616(7)
Organic Reactions: A Brief Review623(82)
A Summary of the Kinds of Organic Reactions
623(4)
A Summary of How Reactions Occur
627(5)
Alcohols and Thiols
632(44)
Naming Alcohols
633(1)
Sources and Uses of Simple Alcohols
634(1)
Properties of Alcohols: Hydrogen Bonding
635(2)
Properties of Alcohols: Acidity and Basicity
637(2)
Preparation of Alcohols
639(2)
Alcohols from Reduction of Carbonyl Compounds
641(3)
Alcohols from Addition of Grignard Reagents to Carbonyl Compounds
644(4)
Reactions of Alcohols
648(5)
Oxidation of Alcohols
653(3)
Protection of Alcohols
656(3)
Spectroscopic Analysis of Alcohols
659(3)
Thiols
662(14)
Interlude---Ethanol as Chemical, Drug, and Poison
664(1)
Summary and Key Words
665(1)
Summary of Reactions
666(2)
Additional Problems
668(8)
Ethers, Epoxides, and Sulfides
676(29)
Naming Ethers
676(1)
Structure and Properties of Ethers
677(1)
Industrial Preparation of Ethers
678(1)
The Williamson Ether Synthesis
679(2)
Alkoxymercuration/Demercuration of Alkenes
681(1)
Reactions of Ethers: Acidic Cleavage
682(1)
Cyclic Ethers: Epoxides
683(3)
Ring-Opening Reactions of Epoxides
686(4)
Crown Ethers
690(1)
Spectroscopic Analysis of Ethers
691(2)
Sulfides
693(12)
Interlude---Epoxy Resins and Adhesives
695(1)
Summary and Key Words
696(1)
Summary of Reactions
697(2)
Additional Problems
699(6)
Chemistry of Carbonyl Compounds: An Overview705(1)
Kinds of Carbonyl Compounds
706(1)
Nature of the Carbonyl Group
707(2)
General Reactions of Carbonyl Compounds
709(6)
Summary
715(1)
Aldehydes and Ketones: Nucleophilic Addition Reactions
716(58)
Properties of Aldehydes and Ketones
717(1)
Naming Aldehydes and Ketones
718(2)
Preparation of Aldehydes
720(1)
Preparation of Ketones
721(2)
Oxidation of Aldehydes and Ketones
723(1)
Nucleophilic Addition Reactions of Aldehydes and Ketones
724(2)
Relative Reactivity of Aldehydes and Ketones
726(1)
Nucleophilic Addition of H2O: Hydration
727(3)
Nucleophilic Addition of HCN: Cyanohydrins
730(2)
Nucleophilic Addition of Grignard Reagents: Alcohol Formation
732(1)
Nucleophilic Addition of Hydride: Reduction
732(1)
Nucleophilic Addition of Amines: Imine and Enamine Formation
733(4)
Nucleophilic Addition of Hydrazine: The Wolff-Kishner Reaction
737(3)
Nucleophilic Addition of Alcohols: Acetal Formation
740(3)
Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction
743(3)
The Cannizzaro Reaction
746(2)
Conjugate Nucleophilic Addition to α,β-Unsaturated Carbonyl Groups
748(4)
Some Biological Nucleophilic Addition Reactions
752(1)
Spectroscopic Analysis of Ketones and Aldehydes
753(21)
Interlude---Insect Antifeedants
759(1)
Summary and Key Words
760(1)
Summary of Reactions
761(3)
Additional Problems
764(10)
Carboxylic Acids
774(28)
Naming Carboxylic Acids
775(2)
Structure and Physical Properties of Carboxylic Acids
777(1)
Dissociation of Carboxylic Acids
778(4)
Substituent Effects on Acidity
782(2)
Substituent Effects in Substituted Benzoic Acids
784(2)
Preparation of Carboxylic Acids
786(2)
Reactions of Carboxylic Acids
788(1)
Reduction of Carboxylic Acids
789(1)
Spectroscopic Analysis of Carboxylic Acids
790(12)
Interlude---Vitamin C
792(2)
Summary and Key Words
794(1)
Summary of Reactions
794(2)
Additional Problems
796(6)
Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions
802(58)
Naming Carboxylic Acid Derivatives
803(3)
Nucleophilic Acyl Substitution Reactions
806(2)
Relative Reactivity of Carboxylic Acid Derivatives
808(2)
Nucleophilic Acyl Substitution Reactions of Carboxylic Acids
810(5)
Chemistry of Acid Halides
815(7)
Chemistry of Acid Anhydrides
822(2)
Chemistry of Esters
824(7)
Chemistry of Amides
831(2)
Chemistry of Nitriles
833(5)
Thiol Esters; Biological Carboxylic Acid Derivatives
838(1)
Polyamides and Polyesters: Step-Growth Polymers
839(4)
Spectroscopy of Carboxylic Acid Derivatives
843(17)
Interlude---β-Lactam Antibiotics
845(2)
Summary and Key Words
847(1)
Summary of Reactions
848(3)
Additional Problems
851(9)
Carbonyl Alpha-Substitution Reactions
860(36)
Keto--Enol Tautomerism
861(3)
Reactivity of Enols: The Mechanisms of Alpha-Substitution Reactions
864(1)
Alpha Halogenation of Ketones and Aldehydes
865(3)
Alpha Bromination of Carboxylic Acids: The Hell--Volhard--Zelinskii Reaction
868(1)
Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
869(4)
Reactivity of Enolate Ions
873(1)
Halogenation of Enolate Ions: The Haloform Reaction
874(2)
Alkylation of Enolate Ions
876(20)
Interlude---Unusual Elements in Organic Chemistry
885(1)
Summary and Key Words
886(1)
Summary of Reactions
887(2)
Additional Problems
889(7)
Carbonyl Condensation Reactions
896(38)
Mechanism of Carbonyl Condensation Reactions
897(1)
Condensations of Aldehydes and Ketones: The Aldol Reaction
898(2)
Carbonyl Condensation Reactions versus Alpha-Substitution Reactions
900(1)
Dehydration of Aldol Products: Synthesis of Enones
901(2)
Recognizing Aldol Products
903(2)
Mixed Aldol Reactions
905(2)
Intramolecular Aldol Reactions
907(2)
The Claisen Condensation Reaction
909(2)
Mixed Claisen Condensations
911(1)
Intramolecular Claisen Condensations: The Dieckmann Cyclization
912(2)
The Michael Reaction
914(3)
The Stork Enamine Reaction
917(2)
Carbonyl Condensation Reactions in Synthesis: The Robinson Annulation Reaction
919(2)
Biological Carbonyl Condensation Reactions
921(13)
Interlude---A Prologue to Metabolism
923(2)
Summary and Key Words
925(1)
Summary of Reactions
926(2)
Additional Problems
928(6)
Aliphatic Amines
934(39)
Naming Amines
935(3)
Structure and Bonding in Amines
938(2)
Physical Properties of Amines
940(1)
Amine Basicity
941(4)
Industrial Sources and Uses of Alkylamines
945(1)
Synthesis of Amines
946(8)
Reactions of Amines
954(2)
Tetraalkylammonium Salts as Phase-Transfer Agents
956(1)
Spectroscopy of Amines
957(16)
Interlude---Morphine Alkaloids: Naturally Occurring Amines
962(2)
Summary and Key Words
964(1)
Summary of Reactions
964(2)
Additional Problems
966(7)
Arylamines and Phenols
973(37)
Basicity of Arylamines
974(3)
Preparation of Arylamines
977(1)
Reactions of Arylamines
978(7)
Phenols
985(1)
Industrial Uses of Phenols
986(2)
Properties of Phenols: Acidity
988(3)
Preparation of Phenols
991(1)
Reactions of Phenols
992(5)
Spectroscopy of Arylamines and Phenols
997(13)
Interlude---Ubiquinones and Metabolic Energy
999(1)
Summary and Key Words
1000(1)
Summary of Reactions
1001(3)
Additional Problems
1004(6)
Biomolecules: Carbohydrates
1010(45)
Classification of Carbohydrates
1011(1)
Configurations of Monosaccharides: Fischer Projections
1012(2)
D,L Sugars
1014(2)
Configurations of the Aldoses
1016(3)
Cyclic Structures of Monosaccharides: Hemiacetal Formation
1019(2)
Monosaccharide Anomers: Mutarotation
1021(2)
Conformations of Monosaccharides
1023(1)
Reactions of Monosaccharides
1024(10)
Stereochemistry of Glucose: The Fischer Proof
1034(4)
Disaccharides
1038(4)
Polysaccharides
1042(3)
Other Important Carbohydrates
1045(1)
Cell-Surface Carbohydrates
1046(9)
Interlude---Sweetness
1048(1)
Summary and Key Words
1049(1)
Summary of Reactions
1050(1)
Additional Problems
1051(4)
Biomolecules: Amino Acids, Peptides, and Proteins
1055(44)
Structures of Amino Acids
1056(4)
Dipolar Structure of Amino Acids
1060(1)
Isoelectric Points
1061(3)
Synthesis of α-Amino Acids
1064(3)
Resolution of R,S Amino Acids
1067(1)
Peptides
1068(2)
Covalent Bonding in Peptides
1070(1)
Peptide Structure Determination: Amino Acid Analysis
1071(1)
Peptide Sequencing: The Edman Degradation
1072(3)
Peptide Sequencing: C-Terminal Residue Determination
1075(1)
Peptide Synthesis
1076(4)
Automated Peptide Synthesis: The Merrifield Solid-Phase Technique
1080(2)
Classification of Proteins
1082(1)
Protein Structure
1083(4)
Enzymes
1087(3)
Protein Denaturation
1090(9)
Interlude---Protein and Nutrition
1091(1)
Summary and Key Words
1092(1)
Summary of Reactions
1093(1)
Additional Problems
1094(5)
Biomolecules: Lipids
1099(29)
Waxes, Fats, and Oils
1100(3)
Soap
1103(2)
Phospholipids
1105(2)
Prostaglandins
1107(1)
Terpenes
1108(3)
Biosynthesis of Terpenes
1111(2)
Steroids
1113(3)
Stereochemistry of Steroids
1116(2)
Steroid Biosynthesis
1118(10)
Interlude---Cholesterol and Heart Disease
1121(1)
Summary and Key Words
1122(1)
Additional Problems
1123(5)
Biomolecules: Heterocycles and Nucleic Acids
1128(44)
Five-Membered Unsaturated Heterocycles
1129(1)
Structures of Pyrrole, Furan, and Thiophene
1130(1)
Electrophilic Substitution Reactions of Pyrrole, Furan, and Thiophene
1131(2)
Pyridine, a Six-Membered Heterocycle
1133(1)
Electrophilic Substitution of Pyridine
1134(1)
Nucleophilic Substitution of Pyridine
1135(1)
Fused-Ring Heterocycles
1136(2)
Nucleic Acids and Nucleotides
1138(4)
Structure of DNA
1142(1)
Base Pairing in DNA: The Watson--Crick Model
1143(3)
Nucleic Acids and Heredity
1146(1)
Replication of DNA
1147(1)
Structure and Synthesis of RNA: Transcription
1148(2)
RNA and Protein Biosynthesis: Translation
1150(4)
DNA Sequencing
1154(6)
DNA Synthesis
1160(3)
The Polymerase Chain Reaction
1163(9)
Interlude---DNA-Based Computing?
1165(2)
Summary and Key Words
1167(1)
Summary of Reactions
1168(1)
Additional Problems
1169(3)
The Organic Chemistry of Metabolic Pathways
1172(39)
An Overview of Metabolism and Biochemical Energy
1172(4)
Catabolism of Fats: β-Oxidation
1176(6)
Catabolism of Carbohydrates: Glycolysis
1182(6)
The Conversion of Pyruvate to Acetyl CoA
1188(3)
The Citric Acid Cycle
1191(4)
Catabolism of Proteins: Transamination
1195(1)
Anabolism of Fatty Acids
1196(5)
Anabolism of Carbohydrates: Gluconeogenesis
1201(10)
Interlude---Basal Metabolism
1204(1)
Summary and Key Words
1205(1)
Additional Problems
1206(5)
Orbitals and Organic Chemistry: Pericyclic Reactions
1211(1)
Atomic and Molecular Orbitals
1212(1)
Molecular Orbitals of Conjugated π Systems
1213(2)
Molecular Orbitals and Pericyclic Reactions
1215(1)
Electrocyclic Reactions
1215(4)
Stereochemistry of Thermal Electrocyclic Reactions
1219(3)
Photochemical Electrocyclic Reactions
1222(2)
Cycloaddition Reactions
1224(3)
Stereochemistry of Cycloadditions
1227(3)
Sigmatropic Rearrangements
1230(1)
Stereochemistry of Sigmatropic Rearrangements
1231(2)
Some Examples of Sigmatropic Rearrangements
1233(3)
A Summary of Rules for Pericyclic Reactions
1236(1)
Interlude---Vitamin D, the Sunshine Vitamin
1237(1)
Summary and Key Words
1238(1)
Additional Problems
1239
Appendix A Nomenclature of Polyfunctional Organic CompoundsA1
Appendix B Acidity Constants for Some Organic CompoundsA8
Appendix C Reaction Mechanisms in ReviewA10
Appendix D GlossaryA15
Appendix E Answers to Selected In-Text ProblemsA41
Index11

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