Organic Chemistry, 7th Edition Upgrade

by T. W. Graham Solomons (Univ. of South Florida); Craig B. Fryhle (Pacific Lutheran Univ.)

• ISBN13: 9780471418030
• ISBN10: 047141803X
• Edition: 7th
• Format: Hardcover
• Copyright: 2002-01-01
• Publisher: Wiley

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