Organic Chemistry (with InfoTrac)

by McMurry, John E.

• ISBN13: 9780534363550
• ISBN10: 0534363555
• Edition: 4th
• Format: Hardcover
• Copyright: 1998-08-03
• Publisher: Brooks Cole

Table of Contents

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 Review	623	(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 Overview	705	(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 Compounds	A1
Appendix B Acidity Constants for Some Organic Compounds	A8
Appendix C Reaction Mechanisms in Review	A10
Appendix D Glossary	A15
Appendix E Answers to Selected In-Text Problems	A41
Index	11