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Organic Chemistry, 7th Edition Upgrade

by ;
ISBN13:

9780471418030

ISBN10:
047141803X
Format:
Hardcover
Pub. Date:
1/1/2002
Publisher(s):
Wiley
List Price: $137.33

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Summary

This bestseller helps readers master basic skills with its clear and easy-to-follow presentation of key concepts. It focuses on the important ideas of organic chemistry and backs them up with illustrations and challenging problems. The authors' acclaimed writing style makes this thorny subject easy to grasp and comprehend. The new edition brings the book to the forefront of the latest research developments. The book includes the ORGANIC VIEW CD, a browser-based study tool with animated 3D graphics, Drill/Review sections, and Practice Tests "The Chemistry of..." boxes throughout highlight biological and other real-world chemistry This edition is completely up-to-date with the latest developments in the field

Author Biography

Craig B. Fryhle is affiliated with Pacific Lutheran University. T. W. Graham Solomons is affiliated with the University of South Florida.

Table of Contents

Carbon Compounds and Chemical Bonds
1(49)
Life Is Organic Chemistry (Molecular graphic: Glycine, an organic molecule found in space)
1(1)
Introduction
2(1)
The Development of Organic Chemistry as a Science
3(1)
The Structural Theory of Organic Chemistry
4(3)
Chemical Bonds: The Octet Rule
7(2)
Writing Lewis Structures
9(1)
Exceptions to the Octet Rule
10(2)
Formal Charge
12(2)
Resonance
14(4)
Quantum Mechanics
18(1)
Atomic Orbitals
19(2)
Molecular Orbitals
21(3)
The Structure of Methane and Ethane: sp3 Hybridization
24(4)
The Structure of Ethene (Ethylene): sp2 Hybridization
28(5)
The Structure of Ethyne (Acetylene): sp Hybridization
33(2)
A Summary of Important Concepts that Come from Quantum Mechanics
35(2)
Molecular Geometry: The Valence Shell Electron-Pair Repulsion (VSEPR) Model
37(3)
Representation of Structural Formulas
40(10)
Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy
50(40)
Structure Is Everything (Molecular graphic: Crixivan, a drug used against HIV)
50(1)
Carbon--Carbon Covalent Bonds
51(1)
Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds
51(4)
Polar Covalent Bonds
55(1)
Polar and Nonpolar Molecules
56(3)
Functional Groups
59(1)
Alkyl Halides or Haloalkanes
60(1)
Alcohols
61(2)
Ethers
63(1)
Amines
63(1)
Aldehydes and Ketones
64(2)
Carboxylic Acids, Amides, and Esters
66(1)
Nitriles
67(1)
Summary of Important Families of Organic Compounds
68(1)
Physical Properties and Molecular Structure
68(8)
Summary of Attractive Electric Forces
76(1)
Infrared Spectroscopy: An Instrumental Method for Detecting Functional Groups
76(14)
An Introduction to Organic Reactions: Acids and Bases
90(39)
Shuttling the Protons (Molecular graphic: Diamox, a drug that prevents altitude sickness)
90(1)
Reactions and Their Mechanisms
91(3)
Acid-Base Reactions
94(4)
The Chemistry of... HOMOs and LUMOs in Reactions
98(1)
Heterolysis of Bonds to Carbon: Carbocations and Carbanions
98(1)
Use of Curved Arrows in Illustrating Reactions
99(2)
The Strength of Acids and Bases: Ka and pKa
101(3)
Predicting the Outcome of Acid--Base Reactions
104(2)
The Relationship between Structure and Acidity
106(4)
Energy Changes
110(1)
The Relationship between the Equilibrium Constant and the Standard Free-Energy Change, ΔG°
111(1)
The Acidity of Carboxylic Acids
112(4)
The Effect of the Solvent on Acidity
116(1)
Organic Compounds as Bases
117(2)
A Mechanism for an Organic Reaction
119(1)
Acids and Bases in Nonaqueous Solutions
120(3)
The Chemistry of Carbonic Anhydrase
121(2)
Acid--Base Reactions and the Synthesis of Deuterium- and Tritium-Labeled Compounds
123(6)
Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis
129(55)
To Be Flexible or Inflexible---Molecular Structure Makes the Difference (Molecular graphic: A portion of the structure of diamond, an exceptionally rigid molecule)
129(1)
Introduction to Alkanes and Cycloalkanes
130(2)
Shapes of Alkanes
132(3)
IUPAC Nomenclature of Alkanes, Alkyl Halides, and Alcohols
135(7)
Nomenclature of Cycloalkanes
142(2)
Nomenclature of Alkenes and Cycloalkenes
144(2)
Nomenclature of Alkynes
146(1)
Physical Properties of Alkanes and Cycloalkanes
147(2)
Sigma Bonds and Bond Rotation
149(2)
Conformational Analysis of Butane
151(2)
The Relative Stabilities of Cycloalkanes: Ring Strain
153(2)
The Origin of Ring Strain in Cyclopropane and Cyclobutane: Angle Strain and Torsional Strain
155(2)
Conformations of Cyclohexane
157(3)
Substituted Cyclohexanes: Axial and Equatorial Hydrogen Atoms
160(3)
Disubstituted Cycloalkanes: Cis-Trans Isomerism
163(5)
Bicyclic and Polycyclic Alkanes
168(1)
Pheromones: Communication by Means of Chemicals
169(1)
Chemical Reactions of Alkanes
170(1)
Synthesis of Alkanes and Cycloalkanes
170(3)
Some General Principles of Structure and Reactivity: A Look Toward Synthesis
173(1)
An Introduction to Organic Synthesis
174(10)
The Chemistry of... From the Inorganic to the Organic
178(6)
Stereochemistry: Chiral Molecules
184(45)
The Handeness of Life (Molecular graphic: The mirror-image stereoisomers of alanine, a chiral amino acid)
184(1)
Isomerism: Constitutional Isomers and Stereoisomers
185(2)
Enantiomers and Chiral Molecules
187(4)
The Biological Importance of Chirality
191(2)
The Historical Origin of Stereochemistry
193(1)
Tests for Chirality: Planes of Symmetry
194(1)
Nomenclature of Enantiomers: The (R--S) System
195(5)
Properties of Enantiomers: Optical Activity
200(5)
The Origin of Optical Activity
205(3)
The Synthesis of Chiral Molecules
208(2)
Chiral Drugs
210(1)
The Chemistry of... Selective Binding of Drug Enantiomers to Left- and Right-hand Coiled DNA
211(1)
Molecules with More Than One Stereocenter
211(4)
Fischer Projection Formulas
215(2)
Stereoisomerism of Cyclic Compounds
217(2)
Relating Configurations through Reactions in Which No Bonds to the Stereocenter Are Broken
219(4)
Separation of Enantiomers: Resolution
223(1)
Compounds with Stereocenters Other than Carbon
224(1)
Chiral Molecules that Do Not Possess a Tetrahedral Atom with Four Different Groups
224(5)
Ionic Reactions---Nucleophilic Substitution and Elimination Reactions of Alkyl Halides
229(52)
Breaking Bacterial Cell Walls with Organic Chemistry (Molecular graphic: The SN2 transition state resulting from collision of a hydroxide anion with chloromethane)
229(1)
Introduction
230(1)
Physical Properties of Organic Halides
231(1)
Nucleophilic Substitution Reactions
231(1)
Nucleophiles
232(1)
Leaving Groups
233(1)
Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction
234(1)
A Mechanism for the SN2 Reaction
235(2)
Transition State Theory: Free-Energy Diagrams
237(3)
The Stereochemistry of SN2 Reactions
240(3)
The Reaction of tert-Butyl Chloride with Hydroxide Ion: An SN1 Reaction
243(1)
A Mechanism for the SN1 Reaction
244(2)
Carbocations
246(3)
The Stereochemistry of SN1 Reactions
249(2)
Factors Affecting the Rates of SN1 and SN2 Reactions
251(10)
Organic Synthesis: Functional Group Transformations Using SN2 Reactions
261(4)
The Chemistry of... Biological Methylation: A Biological Nucleophilic Substitution Reaction
262(3)
Elimination Reactions of Alkyl Halides
265(2)
The E2 Reaction
267(1)
The E1 Reaction
268(1)
Substitution versus Elimination
269(3)
Overall Summary
272(9)
Alkenes and Alkynes 1: Properties and Synthesis. Elimination Reactions of Alkyl Halides
281(40)
Cell Membrane Fluidity (Molecular graphic: cis-9-Octadecenoic acid, an unsaturated fatty acid incorporated into cell membrane phospholipids)
281(1)
Introduction
282(1)
The (E)--(Z) System for Designating Alkene Diastereomers
282(2)
Relative Stabilities of Alkenes
284(3)
Cycloalkenes
287(1)
Synthesis of Alkenes via Elimination Reactions
288(1)
Dehydrohalogenation of Alkyl Halides
288(5)
Dehydration of Alcohols
293(6)
Carbocation Stability and the Occurrence of Molecular Rearrangements
299(4)
Alkenes by Debromination of Vicinal Dibromides
303(1)
Synthesis of Alkynes by Elimination Reactions
304(1)
The Acidity of Terminal Alkynes
305(1)
Replacement of the Acetylenic Hydrogen Atom of Terminal Alkynes
306(1)
Hydrogenation of Alkenes
307(2)
The Chemistry of... Hydrogenation in the Food Industry
308(1)
Hydrogenation: The Function of the Catalyst
309(1)
Hydrogenation of Alkynes
310(2)
Molecular Formulas of Hydrocarbons: The Index of Hydrogen Deficiency
312(9)
Alkenes and Alkynes II: Addition Reactions
321(45)
The Sea: A Treasury of Biologically Active Compounds (Molecular graphic: Dactylyne, a halogenated marine natural product)
321(1)
Introduction: Additions to Alkenes
322(2)
Addition of Hydrogen Halides to Alkenes: Markovnikov's Rule
324(6)
Stereochemistry of the Ionic Addition to an Alkene
330(1)
Addition of Sulfuric Acid to Alkenes
330(1)
Addition of Water to Alkenes: Acid-Catalyzed Hydration
331(3)
Addition of Bromine and Chlorine to Alkenes
334(1)
Stereochemistry of the Addition of Halogens to Alkenes
335(4)
Halohydrin Formation
339(3)
The Chemistry of... Regioselectivity in Unsymmetrically Substituted Bromonium Ions: Bromonium Ions of Ethene, Propene, and 2-Methylpropene
340(2)
Divalent Carbon Compounds: Carbenes
342(2)
Oxidations of Alkenes: Syn Hydroxylation
344(2)
Oxidative Cleavage of Alkenes
346(2)
Addition of Bromine and Chlorine to Alkynes
348(1)
Addition of Hydrogen Halides to Alkynes
349(1)
Oxidative Cleavage of Alkynes
350(1)
Synthetic Strategies Revisited
350(16)
The Chemistry of... Cholesterol Biosynthesis: Elegant and Familiar Reactions in Nature
354(12)
Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination
366(63)
A Thermos of Liquid Helium (Molecular graphic: 1-Chloro-2-propanol)
366(1)
Introduction
367(1)
The Electromagnetic Spectrum
368(2)
Nuclear Magnetic Resonance Spectroscopy
370(4)
Nuclear Spin: The Origin of the Signal
374(2)
Shielding and Deshielding of Protons
376(1)
The Chemical Shift
377(2)
Chemical Shift Equivalent and Nonequivalent Protons
379(2)
Signal Splitting: Spin - Spin Coupling
381(10)
Proton NMR Spectra and Rate Processes
391(2)
Carbon-13 NMR Spectroscopy
393(4)
Two-Dimensional (2D) NMR Techniques
397(6)
The Chemistry of... Magnetic Resonance Imaging in Medicine
402(1)
An Introduction to Mass Spectrometry
403(1)
The Mass Spectrometer
403(3)
The Mass Spectrum
406(3)
Determination of Molecular Formulas and Molecular Weights
409(4)
Fragmentation
413(7)
GC/MS Analysis
420(1)
Mass Spectrometry of Biomolecules
420(9)
Radical Reactions
429(47)
Calicheamicin γII: A Radical Device for Slicing the Backbone of DNA (Molecular graphic: Calicheamicin γI1, a molecule capable of double-strand DNA cleavage, bound to DNA)
429(2)
Introduction
431(2)
The Chemistry of... Radicals in Biology, Medicine, and Industry
432(1)
Homolytic Bond Dissociation Energies
433(4)
The Reactions of Alkanes with Halogens
437(2)
Chlorination of Methane: Mechanism of Reaction
439(3)
Chlorination of Methane: Energy Changes
442(8)
Halogenation of Higher Alkanes
450(3)
The Geometry of Alkyl Radicals
453(1)
Reactions that Generate Tetrahedral Stereocenters
453(3)
Radical Addition to Alkenes: The Anti-Markovnikov Addition of Hydrogen Bromide
456(2)
Radical Polymerization of Alkenes: Chain-Growth Polymers
458(2)
Other Important Radical Reactions
460(16)
Special Topic A: Chain-Growth Polymers
469(7)
Alcohols and Ethers
476(53)
Molecular Hosts (Molecular graphic: Monensin sodium salt, an antibiotic that transports ions across cell membranes)
476(1)
Structure and Nomenclature
477(3)
Physical Properties of Alcohols and Ethers
480(2)
Important Alcohols and Ethers
482(2)
Synthesis of Alcohols from Alkenes
484(1)
Alcohols from Alkenes through Oxymercuration - Demercuration
485(3)
Hydroboration: Synthesis of Organoboranes
488(2)
Alcohols from Alkenes through Hydroboration - Oxidation
490(3)
Reactions of Alcohols
493(1)
Alcohols as Acids
494(1)
Conversion of Alcohols into Mesylates and Tosylates
495(2)
Mesylates and Tosylates in SN2 Reactions
497(2)
The Chemistry of... Alkyl Phosphates
498(1)
Conversion of Alcohols into Alkyl Halides
499(1)
Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides
499(3)
Alkyl Halides from the Reaction of Alcohols with PBr3 or SOCI2
502(1)
Synthesis of Ethers
503(4)
Reactions of Ethers
507(1)
Epoxides
508(4)
The Chemistry of... The Sharpless Asymmetric Epoxidation
510(2)
Reactions of Epoxides
512(4)
The Chemistry of... Epoxides, Carcinogens, and Biological Oxidation
514(2)
Anti Hydroxylation of Alkenes via Epoxides
516(3)
Crown Ethers: Nucleophilic Substitution Reactions in Relatively Nonpolar Aprotic Solvents by Phase-Transfer Catalysis
519(4)
Summary of Reactions of Alkenes, Alcohols, and Ethers
523(6)
Alcohols from Carbonyl Compounds. Oxidation - Reduction and Organometallic Compounds
529(42)
The Two Aspects of the Coenzyme NADH (Molecular graphic: Nicotinamide [niacin])
529(1)
Introduction
530(2)
Oxidation - Reduction Reactions in Organic Chemistry
532(1)
Alcohols by Reduction of Carbonyl Compounds
533(5)
The Chemistry of... Alcohol Dehydrogenase
536(1)
The Chemistry of... Stereoselective Reduction of Carbonyl Groups
537(1)
Oxidation of Alcohols
538(5)
Organometallic Compounds
543(1)
Preparation of Organolithium and Organomagnesium Compounds
544(2)
Reactions of Organolithium and Organomagnesium Compounds
546(3)
Alcohols from Grignard Reagents
549(7)
Lithium Dialkylcuprates: The Corey - Posner, Whitesides - House Synthesis
556(3)
Protecting Groups
559(12)
First Review Problem Set
566(5)
Conjugated Unsaturated Systems
571(48)
Molecules with the Nobel Prize in Their Synthetic Lineage (Molecular graphic: Morphine, the synthesis of which involved the Diels - Alder reaction)
571(1)
Introduction
572(1)
Allylic Substitution and the Allyl Radical
573(4)
The Stability of the Allyl Radical
577(3)
The Allyl Cation
580(2)
Summary of Rules for Resonance
582(4)
Alkadienes and Polyunsaturated Hydrocarbons
586(1)
1,3-Butadiene: Electron Delocalization
587(2)
The Stability of Conjugated Dienes
589(2)
Ultraviolet - Visible Spectroscopy
591(9)
The Chemistry of... The Photochemistry of Vision
596(4)
Electrophilic Attack on Conjugated Dienes: 1,4 Addition
600(4)
The Diels-Alder Reaction: A 1,4-Cycloaddition Reaction of Dienes
604(15)
Aromatic Compounds
619(42)
Green Chemistry (Molecular graphic: Benzene, parent molecule in the family of aromatic hydrocarbons)
619(1)
Introduction
620(1)
Nomenclature of Benzene Derivatives
621(2)
Reactions of Benzene
623(1)
The Kekule Structure for Benzene
624(2)
The Stability of Benzene
626(1)
Modern Theories of the Structure of Benzene
627(3)
Huckel's Rule: The (4n + 2) π Electron Rule
630(7)
Other Aromatic Compounds
637(5)
The Chemistry of... Nanotubes
641(1)
Heterocyclic Aromatic Compounds
642(1)
Aromatic Compounds in Biochemistry
643(3)
Spectroscopy of Aromatic Compounds
646(15)
The Chemistry of... Sunscreens (Catching the Sun's Rays and What Happens to Them)
650(11)
Reactions of Aromatic Compounds
661(53)
Biosynthesis of Thyroxine: Aromatic Substitution Involving Iodine (Molecular graphic: Thyroxine, an aromatic iodine-containing hormone associated with regulation of metabolic rate)
661(1)
Electrophilic Aromatic Substitution Reactions
662(1)
A General Mechanism for Electrophilic Aromatic Substitution: Arenium Ions
663(2)
Halogenation of Benzene
665(2)
Nitration of Benzene
667(1)
Sulfonation of Benzene
668(1)
Friedel - Crafts Alkylation
669(2)
Friedel - Crafts Acylation
671(2)
Limitations of Friedel - Crafts Reactions
673(2)
Synthetic Applications of Friedel - Crafts Acylations: The Clemmensen Reduction
675(2)
Effect of Substituents on Reactivity and Orientation
677(3)
Theory of Substituent Effects on Electrophilic Aromatic Substitution
680(12)
The Chemistry of... Iodine Incorporation in Thyroxine Biosynthesis
690(2)
Reactions of the Side Chain of Alkylbenzenes
692(4)
The Chemistry of... Industrial Styrene Synthesis
693(3)
Alkenylbenzenes
696(2)
Synthetic Applications
698(4)
Allylic and Benzylic Halides in Nucleophilic Substitution Reactions
702(2)
Reduction of Aromatic Compounds
704(10)
Aldehydes and Ketones I: Nucleophilic Addition to the Carbonyl Group
714(52)
A Very Versatile Vitamin, Pyridoxine (Vitamin B6) (Molecular graphic: Pyridoxal phosphate [vitamin B6])
714(1)
Introduction
715(1)
Nomenclature of Aldehydes and Ketones
716(1)
Physical Properties
717(2)
Synthesis of Aldehydes
719(4)
Synthesis of Ketones
723(4)
Nucleophilic Addition to the Carbon -- Oxygen Double Bond
727(3)
The Addition of Alcohols: Hemiacetals and Acetals
730(8)
The Addition of Derivatives of Ammonia
738(5)
The Chemistry of... Pyridoxal Phosphate
742(1)
The Addition of Hydrogen Cyanide
743(2)
The Addition of Ylides: The Wittig Reaction
745(4)
The Addition of Organometallic Reagents: The Reformatsky Reaction
749(1)
Oxidation of Aldehydes and Ketones
750(2)
Chemical Analysis for Aldehydes and Ketones
752(1)
Spectroscopic Properties of Aldehydes and Ketones
753(13)
Aldehydes and Ketones II. Aldol Reactions
766(44)
TIM (Triose Phosphate Isomerase) Recycles Carbon via an Enol (Molecular graphic: Glyceraldehyde-3-phosphate, a key intermediate in metabolic energy production)
766(1)
The Acidity of the α Hydrogens of Carbonyl Compounds: Enolate Anions
767(2)
Keto and Enol Tautomers
769(1)
Reactions via Enols and Enolate Anions
770(6)
The Aldol Reaction: The Addition of Enolate Anions to Aldehydes and Ketones
776(4)
Crossed Aldol Reactions
780(6)
Cyclizations via Aldol Condensations
786(2)
Lithium Enolates
788(6)
The Chemistry of... Silyl Enol Ethers
792(2)
α-Selenation: A Synthesis of α,β-Unsaturated Carbonyl Compounds
794(1)
Additions to α,β-Unsaturated Aldehydes and Ketones
795(15)
The Chemistry of... Calicheamicin γI1 Activation for Cleavage of DNA
799(11)
Carboxylic Acids and Their Derivatives. Nucleophilic Addition-Elimination at the Acyl Carbon
810(67)
A Common Bond (Molecular graphic: A portion of nylon 6, 6, a polyamide)
810(1)
Introduction
811(1)
Nomenclature and Physical Properties
811(9)
Preparation of Carboxylic Acids
820(2)
Nucleophilic Addition - Elimination at the Acyl Carbon
822(3)
Acyl Chlorides
825(2)
Carboxylic Acid Anhydrides
827(1)
Esters
828(8)
Amides
836(8)
The Chemistry of... Penicillins
844(1)
α-Halo Acids: The Hell - Volhard - Zelinski Reaction
844(2)
Derivatives of Carbonic Acid
846(3)
Decarboxylation of Carboxylic Acids
849(2)
The Chemistry of... Thiamine
850(1)
Chemical Tests for Acyl Compounds
851(26)
Special Topic B: Step-Growth Polymers
868(9)
Synthesis and Reactions of β-Dicarbonyl Compounds: More Chemistry of Enolate Anions
877(65)
Imposters (Molecular graphic: 5-Fluorouracil, an enzyme inhibitor that has anticancer activity by masquerading as a natural substrate)
877(1)
Introduction
878(1)
The Claisen Condensation: The Synthesis of β-Keto Esters
879(6)
The Acetoacetic Ester Synthesis: Synthesis of Methyl Ketones (Substituted Acetones)
885(7)
The Malonic Ester Synthesis: Synthesis of Substituted Acetic Acids
892(4)
Further Reactions of Active Hydrogen Compounds
896(1)
Direct Alkylation of Esters and Nitriles
897(1)
Alkylation of 1,3-Dithianes
898(2)
The Knoevenagel Condensation
900(1)
Michael Additions
900(2)
The Chemistry of... A Suicide Enzyme Substrate
902(1)
The Mannich Reaction
902(2)
Synthesis of Enamines: Stork Enamine Reactions
904(4)
Barbiturates
908(34)
The Chemistry of... Antibody-Catalyzed Aldol Condensations
909(14)
Special Topic C: Thiols, Sulfur Ylides, and Disulfides
923(5)
Special Topic D: Thiol Esters and Lipid Biosynthesis
928(14)
Amines
942(72)
Neurotoxins and Neurotransmitters (Molecular graphic: Histrionicatoxin, a paralyzing neurotoxin from certain poison dart frogs)
942(2)
Nomenclature
944(1)
Physical Properties and Structure of Amines
945(2)
Basicity of Amines: Amine Salts
947(8)
The Chemistry of... HPLC Resolution of Enantiomers
954(1)
Some Biologically Important Amines
955(2)
Preparation of Amines
957(8)
Reactions of Amines
965(1)
Reactions of Amines with Nitrous Acid
966(3)
The Chemistry of... N-Nitrosoamines
968(1)
Replacement Reactions of Arenediazonium Salts
969(3)
Coupling Reactions of Arenediazonium Salts
972(3)
Reactions of Amines with Sulfonyl Chlorides
975(2)
The Sulfa Drugs: Sulfanilamide
977(3)
Analysis of Amines
980(2)
Eliminations Involving Ammonium Compounds
982(32)
Special Topic E: Reactions and Synthesis of Heterocyclic Amines
997(11)
Special Topic F: Alkaloids
1008(6)
Phenols and Aryl Halides: Nucleophilic Aromatic Substitution
1014(74)
A Silver Chalice (Molecular graphic: 4-tert-Butylcalix[4]arene, a chalice-shaped molecule)
1014(1)
Structure and Nomenclature of Phenols
1015(1)
Naturally Occurring Phenols
1016(3)
The Chemistry of... Polyketide Anticancer Antibiotic Biosynthesis
1017(2)
Physical Properties of Phenols
1019(1)
Synthesis of Phenols
1019(4)
Reactions of Phenols as Acids
1023(2)
Other Reactions of the O---H Group of Phenols
1025(1)
Cleavage of Alkyl Aryl Ethers
1026(1)
Reactions of the Benzene Ring of Phenols
1027(2)
The Claisen Rearrangement
1029(1)
Quinones
1030(2)
Aryl Halides and Nucleophilic Aromatic Substitution
1032(7)
The Chemistry of... Bacterial Dehalogenation of a PCB Derivative
1035(4)
Spectroscopic Analysis of Phenols and Aryl Halides
1039(49)
Second Review Problem Set
1050(6)
Special Topic G: Electrocyclic and Cycloaddition Reactions
1056(15)
Special Topic H: Organic Halides and Organometallic Compounds in the Environment
1071(6)
Special Topic I: Transition Metal Organometallic Compounds
1077(11)
Carbohydrates
1088(54)
Carbohydrate Recognition in Healing and Disease (Molecular graphic: Sialyl Lewis, x a carbohydrate that is important in the recognition and healing of traumatized tissue)
1088(1)
Introduction
1089(3)
Monosaccharides
1092(6)
Mutarotation
1098(1)
Glycoside Formation
1099(3)
Other Reactions of Monosaccharides
1102(2)
Oxidation Reactions of Monosaccharides
1104(6)
Reduction of Monosaccharides: Alditols
1110(1)
Reactions of Monosaccharides with Phenylhydrazine: Osazones
1110(2)
Synthesis and Degradation of Monosaccharides
1112(2)
The D Family of Aldoses
1114(1)
Fischer's Proof of the Configuration of D-(+)-Glucose
1114(4)
Disaccharides
1118(5)
The Chemistry of... Artificial Sweeteners (How Sweet It Is)
1122(1)
Polysaccharides
1123(5)
Other Biologically Important Sugars
1128(1)
Sugars that Contain Nitrogen
1129(1)
Glycolipids and Glycoproteins of the Cell Surface
1130(2)
Carbohydrate Antibiotics
1132(10)
Lipids
1142(37)
Insulation for Nerves (Molecular graphic: A sphingomyelin molecule, found in myelin sheath membranes)
1142(1)
Introduction
1143(1)
Fatty Acids and Triacylglycerols
1144(8)
The Chemistry of... Olestra and Other Fat Substitutes
1148(4)
Terpenes and Terpenoids
1152(4)
Steroids
1156(9)
Prostaglandins
1165(2)
Phospholipids and Cell Membranes
1167(3)
Waxes
1170(9)
Amino Acids and Proteins
1179(49)
Catalytic Antibodies: Designer Catalysts (Molecular graphic: A synthetic Diels-alderase catalytic antibody with a bound hapten)
1179(1)
Introduction
1180(1)
Amino Acids
1181(5)
Laboratory Synthesis of α-Amino Acids
1186(4)
Analysis of Polypeptides and Proteins
1190(3)
Amino Acid Sequence of Polypeptides and Proteins
1193(3)
Primary Structure of Polypeptides and Proteins
1196(4)
The Chemistry of... Sickle Cell Anemia
1199(1)
Polypeptide and Protein Synthesis
1200(5)
Secondary, Tertiary, and Quaternary Structure of Proteins
1205(7)
Introduction to Enzymes
1212(1)
Lysozyme: Mode of Action of an Enzyme
1213(2)
Serine Proteases
1215(7)
The Chemistry of... Some Catalytic Antibodies
1220(2)
Hemoglobin: A Conjugated Protein
1222(6)
Nucleic Acids and Protein Synthesis
1228(1)
Tools for Finding Families (Molecular graphic: A cytosine-guanine base pair, depicting the van der Waals surface as an electrostatic patential map)
1228(1)
Introduction
1229(1)
Nucleotides and Nucleosides
1229(3)
Laboratory Synthesis of Nucleosides and Nucleotides
1232(4)
Deoxyribonucleic Acid: DNA
1236(7)
RNA and Protein Synthesis
1243(7)
Determining the Base Sequence of DNA
1250(3)
Laboratory Synthesis of Oligonucleotides
1253(2)
The Polymerase Chain Reaction
1255(3)
Sequencing of the Human Genome: An Instruction Book for the Molecules of Life
1258
Answers to Selected Problems 1(1)
Glossary 1(1)
Illustration and Photo Credits 1(10)
Index 11
Appendix A
Upgrade Edition Additional Problems
1(23)
Answers to Upgraded Edition Additional Problems
24


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