Organic Chemistry (with InfoTrac Printed Access Card)

by McMurry, John E.

• ISBN13: 9780534389994
• ISBN10: 0534389996
• Edition: 6th
• Format: Hardcover
• Copyright: 2003-03-21
• Publisher: Brooks Cole

Summary

John McMurry's international best-seller is widely and consistently praised as the most clearly written book on the market. Why? In John McMurry's words: "I have been asked hundreds of times over the past ten years why I wrote this book. I wrote this book because I love writing. I get great pleasure and satisfaction from taking a complicated subject, turning it around until I see it clearly from a new angle, and then explaining it in simple words. I write to explain chemistry to students the way I wish it had been explained to me years ago." Through his lucid writing and ability to show the beauty and logic of organic chemistry, McMurry makes learning enjoyable for students. The highest compliment that can be given to a chemistry book applies to McMurry: It works! Mainstream in level, McMurry's coverage is concise yet doesn't omit any key topics. McMurry blends the traditional functional-group approach with a mechanistic approach. The primary approach, by functional group, begins with the simple and progresses to the more complex so that readers who are not yet versed in the subtleties of mechanisms are first exposed to the "what" of chemistry before beginning to grapple with the "why." Within this primary organization, the author places a heavy emphasis on explaining the fundamental mechanistic similarities. In this edition, McMurry retains his standard-setting features (including his innovative vertical format for explaining reaction mechanisms) while revising his text line-by-line to include hundreds of small but important improvements. For example, the Sixth Edition includes new examples, additional steps in existing examples, new problems, new phrases to clarify the exposition, and a vibrant new art program. In addition, new icons in the text lead students to a variety of new online resources. McMurry's text is in use at hundreds of colleges and universities around the world, from North America, to the United Kingdom and the Pacific Rim.

Table of Contents

Structure and Bonding
Atomic Structure	3	(1)
Atomic Structure: Orbitals	3	(2)
Atomic Structure: Electron Configurations	5	(1)
Development of Chemical Bonding Theory	6	(1)
The Nature of Chemical Bonds	7	(3)
Valence Bond Theory	10	(1)
Hybridization: sp3 Orbitals and the Structure of Methane	11	(1)
Hybridization: sp3 Orbitals and the Structure of Ethane	12	(1)
Hybridization: sp2 Orbitals and the Structure of Ethylene	13	(3)
Hybridization: sp Orbitals and the Structure of Acetylene	16	(1)
Hybridization of Nitrogen and Oxygen	17	(2)
Molecular Orbital Theory	19	(10)
Chemistry@Work: Chemicals, Toxicity, and Risk	20	(1)
Summary and Key Words	21	(2)
Exercises	23	(5)
Building Block Questions	28	(1)
InfoTrac College Edition	28	(1)
Polar Covalent Bonds; Acids and Bases
Polar Covalent Bonds: Electronegativity	29	(3)
Polar Covalent Bonds: Dipole Moments	32	(2)
Formal Charges	34	(3)
Resonance	37	(2)
Rules for Resonance Forms	39	(1)
Drawing Resonance Forms	40	(3)
Acids and Bases: The Bronsted-Lowry Definition	43	(2)
Acid and Base Strength	45	(1)
Predicting Acid-Base Reactions from pKa Values	46	(2)
Organic Acids and Organic Bases	48	(3)
Acids and Bases: The Lewis Definition	51	(4)
Drawing Chemical Structures	55	(2)
Molecular Models	57	(11)
Chemistry@Work: Alkaloids: Naturally Occurring Bases	58	(1)
Summary and Key Words	59	(1)
Exercises	60	(7)
Building Block Questions	67	(1)
InfoTrac College Edition	67	(1)
Organic Compounds: Alkanes and Cycloalkanes
Functional Groups	68	(6)
Alkanes and Alkane Isomers	74	(3)
Alkyl Groups	77	(3)
Naming Alkanes	80	(6)
Properties of Alkanes	86	(2)
Cycloalkanes	88	(1)
Naming Cycloalkanes	89	(3)
Cis-Trans Isomerism in Cycloalkanes	92	(11)
Chemistry@Work: Gasoline	94	(2)
Summary and Key Words	96	(1)
Exercises	97	(5)
Building Block Questions	102	(1)
InfoTrac College Edition	102	(1)
Stereochemistry of Alkanes and Cycloalkanes
Conformations of Ethane	103	(2)
Conformations of Propane	105	(1)
Conformations of Butane	106	(3)
Stability of Cycloalkanes: The Baeyer Strain Theory	109	(2)
The Nature of Ring Strain	111	(1)
Cyclopropane: An Orbital View	112	(1)
Conformations of Cyclobutane and Cyclopentane	113	(2)
Conformations of Cyclohexane	115	(1)
Axial and Equatorial Bonds in Cyclohexane	116	(2)
Conformational Mobility of Cyclohexane	118	(1)
Conformations of Monosubstituted Cyclohexanes	119	(3)
Conformational Analysis of Disubstituted Cyclohexanes	122	(3)
Boat Cyclohexane	125	(1)
Conformations of Polycyclic Molecules	126	(9)
Chemistry@Work: Molecular Mechanics	128	(1)
Summary and Key Words	129	(1)
Exercises	130	(4)
Building Block Questions	134	(1)
InfoTrac College Edition	134	(1)
An Overview of Organic Reactions
Kinds of Organic Reactions	135	(1)
How Organic Reactions Occur: Mechanisms	136	(2)
Radical Reactions and How They Occur	138	(1)
Polar Reactions and How They Occur	139	(5)
An Example of a Polar Reaction: Addition of HBr to Ethylene	144	(3)
Using Curved Arrows in Polar Reaction Mechanisms	147	(3)
Describing a Reaction: Equilibria, Rates, and Energy Changes	150	(3)
Describing a Reaction: Bond Dissociation Energies	153	(3)
Describing a Reaction: Energy Diagrams and Transition States	156	(2)
Describing a Reaction: Intermediates	158	(12)
Chemistry@Work: Explosives	160	(2)
Summary and Key Words	162	(1)
Exercises	163	(5)
Building Block Questions	168	(1)
InfoTrac College Edition	168	(2)
Alkenes: Structure and Reactivity
Industrial Preparation and Use of Alkenes	170	(1)
Calculating Degree of Unsaturation	171	(2)
Naming Alkenes	173	(2)
Electronic Structure of Alkenes	175	(1)
Cis-Trans Isomerism in Alkenes	176	(1)
Sequence Rules: The E,Z Designation	177	(4)
Stability of Alkenes	181	(3)
Electrophilic Addition of HX to Alkenes	184	(3)
Orientation of Electrophilic Addition: Markovnikov's Rule	187	(3)
Carbocation Structure and Stability	190	(2)
The Hammond Postulate	192	(3)
Evidence for the Mechanism of Electrophilic Addition: Carbocation Rearrangements	195	(12)
Chemistry@Work: Terpenes: Naturally Occurring Alkenes	197	(1)
Summary and Key Words	198	(1)
Exercises	199	(6)
Building Block Questions	205	(1)
InfoTrac College Edition	205	(2)
Alkenes: Reactions and Synthesis
Preparation of Alkenes: A Preview of Elimination Reactions	207	(1)
Addition of Halogens to Alkenes	208	(2)
Halohydrin Formation	210	(2)
Addition of Water to Alkenes: Oxymercuration	212	(3)
Addition of Water to Alkenes: Hydroboration	215	(4)
Addition of Carbenes to Alkenes: Cyclopropane Synthesis	219	(3)
Reduction of Alkenes: Hydrogenation	222	(2)
Oxidation of Alkenes: Hydroxylation and Cleavage	224	(3)
Biological Alkene Addition Reactions	227	(1)
Addition of Radicals to Alkenes: Polymers	228	(18)
Chemistry@Work: Natural Rubber	233	(1)
Summary and Key Words	234	(1)
Summary of Reactions	235	(2)
Exercises	237	(8)
Building Block Questions	245	(1)
InfoTrac College Edition	245	(1)
Alkynes: An Introduction to Organic Synthesis
Electronic Structure of Alkynes	246	(1)
Naming Alkynes	247	(1)
Preparation of Alkynes: Elimination Reactions of Dihalides	248	(1)
Reactions of Alkynes: Addition of HX and X2	249	(1)
Hydration of Alkynes	250	(4)
Reduction of Alkynes	254	(2)
Oxidative Cleavage of Alkynes	256	(1)
Alkyne Acidity: Formation of Acetylide Anions	257	(1)
Alkylation of Acetylide Anions	258	(2)
An Introduction to Organic Synthesis	260	(15)
Chemistry@Work: The Art of Organic Synthesis	265	(1)
Summary and Key Words	266	(1)
Summary of Reactions	266	(2)
Exercises	268	(6)
Building Block Questions	274	(1)
InfoTrac College Edition	274	(1)
Stereochemistry
Enantiomers and the Tetrahedral Carbon	275	(2)
The Reason for Handedness in Molecules: Chirality	277	(3)
Optical Activity	280	(1)
Pasteur's Discovery of Enantiomers	281	(1)
Sequence Rules for Specification of Configuration	282	(5)
Diastereomers	287	(1)
Meso Compounds	288	(2)
Molecules with More than Two Chirality Centers	290	(1)
Physical Properties of Stereoisomers	291	(1)
Racemic Mixtures and Their Resolution	291	(2)
A Brief Review of Isomerism	293	(2)
Stereochemistry of Reactions: Addition of HBr to Alkenes	295	(1)
Stereochemistry of Reactions: Addition of Br2 to Alkenes	296	(2)
Stereochemistry of Reactions: Addition of HBr to a Chiral Alkene	298	(1)
Chirality at Atoms Other Than Carbon	299	(1)
Chirality in Nature	300	(1)
Prochirality	301	(16)
Chemistry@Work: Chiral Drugs	304	(1)
Summary and Key Words	305	(1)
Exercises	306	(9)
Building Block Questions	315	(1)
InfoTrac College Edition	315	(2)
Alkyl Halides
Naming Alkyl Halides	317	(2)
Structure of Alkyl Halides	319	(1)
Preparing Alkyl Halides	319	(1)
Radical Halogenation of Alkanes	320	(3)
Allylic Bromination of Alkenes	323	(2)
Stability of the Allyl Radical: Resonance Revisited	325	(2)
Preparing Alkyl Halides from Alcohols	327	(2)
Reactions of Organohalides: Grignard Reagents	329	(1)
Organometallic Coupling Reactions	330	(2)
Oxidation and Reduction in Organic Chemistry	332	(11)
Chemistry@Work: Naturally Occurring Organohalides	335	(1)
Summary and Key Words	336	(1)
Summary of Reactions	336	(2)
Exercises	338	(4)
Building Block Questions	342	(1)
InfoTrac College Edition	342	(1)
Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
The Discovery of the Walden Inversion	343	(1)
Stereochemistry of Nucleophilic Substitution	344	(2)
Kinetics of Nucleophilic Substitution	346	(1)
The SN2 Reaction	347	(2)
Characteristics of the SN2 Reaction	349	(7)
The SN1 Reaction	356	(1)
Kinetics of the SN1 Reaction	357	(2)
Stereochemistry of the SN1 Reaction	359	(2)
Characteristics of the SN1 Reaction	361	(6)
Elimination Reactions of Alkyl Halides: Zaitsev's Rule	367	(2)
The E2 Reaction	369	(3)
Elimination Reactions and Cyclohexane Conformation	372	(2)
The Deuterium Isotope Effect	374	(1)
The E1 Reaction	374	(2)
Summary of Reactivity: SN1, SN2, E1, E2	376	(2)
Substitution Reactions in Synthesis	378	(16)
Chemistry@Work: Substitution Reactions in Living Organisms	380	(1)
Summary and Key Words	381	(1)
Summary of Reactions	382	(1)
Exercises	383	(9)
Building Block Questions	392	(1)
InfoTrac College Edition	392	(2)
Structure Determination: Mass Spectrometry and Infrared Spectroscopy
Mass Spectrometry	394	(2)
Interpreting Mass Spectra	396	(1)
Interpreting Mass-Spectral Fragmentation Patterns	397	(3)
Mass-Spectral Behavior of Some Common Functional Groups	400	(3)
Spectroscopy and the Electromagnetic Spectrum	403	(3)
Infrared Spectroscopy of Organic Molecules	406	(1)
Interpreting Infrared Spectra	407	(4)
Infrared Spectra of Hydrocarbons	411	(1)
Infrared Spectra of Some Common Functional Groups	412	(12)
Chemistry@Work: Chromatography: Purifying Organic Compounds	415	(2)
Summary and Key Words	417	(1)
Exercises	417	(6)
Building Block Questions	423	(1)
InfoTrac College Edition	423	(1)
Structure Determination: Nuclear Magnetic Resonance Spectroscopy
Nuclear Magnetic Resonance Spectroscopy	424	(2)
The Nature of NMR Absorptions	426	(3)
Chemical Shifts	429	(2)
13C NMR Spectroscopy: Signal Averaging and FT-NMR	431	(1)
Characteristics of 13C NMR Spectroscopy	432	(2)
DEPT 13C NMR Spectroscopy	434	(3)
Uses of 13C NMR Spectroscopy	437	(1)
1H NMR Spectroscopy and Proton Equivalence	438	(2)
Chemical Shifts in 1H NMR Spectroscopy	440	(3)
Integration of 1H NMR Absorptions: Proton Counting	443	(1)
Spin-Spin Splitting in 1H NMR Spectra	443	(5)
More Complex Spin-Spin Splitting Patterns	448	(3)
Uses of 1H NMR Spectroscopy	451	(14)
Chemistry@Work: Magnetic Resonance Imaging (MRI)	452	(1)
Summary and Key Words	452	(1)
Exercises	453	(10)
Building Block Questions	463	(1)
InfoTrac College Edition	463	(2)
Conjugated Dienes and Ultraviolet Spectroscopy
Preparation and Stability of Conjugated Dienes	465	(2)
Molecular Orbital Description of 1,3-Butadiene	467	(2)
Electrophilic Additions to Conjugated Dienes: Allylic Carbocations	469	(3)
Kinetic versus Thermodynamic Control of Reactions	472	(2)
The Diels--Alder Cycloaddition Reaction	474	(1)
Characteristics of the Diels--Alder Reaction	475	(5)
Diene Polymers: Natural and Synthetic Rubbers	480	(2)
Structure Determination in Conjugated Systems: Ultraviolet Spectroscopy	482	(1)
Ultraviolet Spectrum of 1,3-Butadiene	483	(2)
Interpreting Ultraviolet Spectra: The Effect of Conjugation	485	(1)
Conjugation, Color, and the Chemistry of Vision	486	(13)
Chemistry@Work: Photolithography	488	(1)
Summary and Key Words	489	(1)
Summary of Reactions	490	(1)
Exercises	490	(7)
Building Block Questions	497	(1)
InfoTrac College Edition	497	(2)
Benzene and Aromaticity
Sources of Aromatic Hydrocarbons	499	(1)
Naming Aromatic Compounds	500	(2)
Structure and Stability of Benzene	502	(2)
Molecular Orbital Description of Benzene	504	(1)
Aromaticity and the Huckel 4n + 2 Rule	505	(2)
Aromatic Ions	507	(3)
Aromatic Heterocycles: Pyridine and Pyrrole	510	(2)
Why 4n + 2?	512	(2)
Polycyclic Aromatic Compounds: Naphthalene	514	(1)
Spectroscopy of Aromatic Compounds	515	(14)
Chemistry@Work: Aspirin, NSAIDs, and COX-2 Inhibitors	519	(1)
Summary and Key Words	520	(1)
Exercises	521	(6)
Building Block Questions	527	(1)
InfoTrac College Edition	527	(2)
Chemistry of Benzene: Electrophilic Aromatic Substitution
Bromination of Aromatic Rings	529	(3)
Other Aromatic Substitutions	532	(3)
Alkylation of Aromatic Rings: The Friedel-Crafts Reaction	535	(3)
Acylation of Aromatic Rings	538	(1)
Substituent Effects in Substituted Aromatic Rings	539	(4)
An Explanation of Substituent Effects	543	(6)
Trisubstituted Benzenes: Additivity of Effects	549	(2)
Nucleophilic Aromatic Substitution	551	(2)
Benzyne	553	(2)
Oxidation of Aromatic Compounds	555	(3)
Reduction of Aromatic Compounds	558	(1)
Synthesis of Trisubstituted Benzenes	559	(19)
Chemistry@Work: Combinatorial Chemistry	564	(2)
Summary and Key Words	566	(1)
Summary of Reactions	566	(3)
Exercises	569	(8)
Building Block Questions	577	(1)
InfoTrac College Edition	577	(1)
A Brief Review of Organic Reactions
A Summary of the Kinds of Organic Reactions	578	(4)
A Summary of Organic Reaction Mechanisms	582	(6)
Problems	586	(1)
Building Block Questions	586	(1)
InfoTrac College Edition	586	(2)
Alcohols and Phenols
Naming Alcohols and Phenols	588	(2)
Properties of Alcohols and Phenols: Hydrogen Bonding	590	(1)
Properties of Alcohols and Phenols: Acidity and Basicity	591	(5)
Preparation of Alcohols: A Review	596	(2)
Alcohols from Reduction of Carbonyl Compounds	598	(3)
Alcohols from Reaction of Carbonyl Compounds with Grignard Reagents	601	(4)
Some Reactions of Alcohols	605	(6)
Oxidation of Alcohols	611	(2)
Protection of Alcohols	613	(2)
Preparation and Uses of Phenols	615	(3)
Reactions of Phenols	618	(1)
Spectroscopy of Alcohols and Phenols	619	(21)
Chemistry@Work: Ethanol: Chemical, Drug, and Poison	623	(1)
Summary and Key Words	624	(1)
Summary of Reactions	625	(3)
Exercises	628	(10)
Building Block Questions	638	(1)
InfoTrac College Edition	638	(2)
Ethers and Epoxides; Thiols and Sulfides
Naming Ethers	640	(1)
Structure, Properties, and Sources of Ethers	640	(2)
The Williamson Ether Synthesis	642	(1)
Alkoxymercuration of Alkenes	643	(1)
Reactions of Ethers: Acidic Cleavage	644	(2)
Reactions of Ethers: Claisen Rearrangement	646	(2)
Cyclic Ethers: Epoxides	648	(1)
Ring-Opening Reactions of Epoxides	649	(5)
Crown Ethers	654	(1)
Thiols and Sulfides	655	(3)
Spectroscopy of Ethers	658	(14)
Chemistry@Work: Epoxy Resins and Adhesives	660	(1)
Summary and Key Words	661	(1)
Summary of Reactions	662	(2)
Exercises	664	(7)
Building Block Questions	671	(1)
InfoTrac College Edition	671	(1)
A Preview of Carbonyl Compounds
Kinds of Carbonyl Compounds	672	(2)
Nature of the Carbonyl Group	674	(1)
General Reactions of Carbonyl Compounds	675	(5)
Summary	680	(3)
Problems	680	(1)
Building Block Questions	681	(1)
InfoTrac College Edition	681	(2)
Aldehydes and Ketones: Nucleophilic Addition Reactions
Naming Aldehydes and Ketones	683	(2)
Preparation of Aldehydes and Ketones	685	(2)
Oxidation of Aldehydes and Ketones	687	(1)
Nucleophilic Addition Reactions of Aldehydes and Ketones	688	(2)
Relative Reactivity of Aldehydes and Ketones	690	(1)
Nucleophilic Addition of H2O: Hydration	691	(2)
Nucleophilic Addition of HCN: Cyanohydrin Formation	693	(2)
Nucleophilic Addition of Grignard Reagents and Hydride Reagents: Alcohol Formation	695	(1)
Nucleophilic Addition of Amines: Imine and Enamine Formation	696	(4)
Nucleophilic Addition of Hydrazine: The Wolff-Kishner Reaction	700	(2)
Nucleophilic Addition of Alcohols: Acetal Formation	702	(4)
Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction	706	(3)
The Cannizzaro Reaction: Biological Reductions	709	(2)
Conjugate Nucleophilic Addition to α,β-Unsaturated Aldehydes and Ketones	711	(4)
Some Biological Nucleophilic Addition Reactions	715	(1)
Spectroscopy of Aldehydes and Ketones	716	(22)
Chemistry@Work: Enantioselective Synthesis	720	(1)
Summary and Key Words	721	(1)
Summary of Reactions	722	(3)
Exercises	725	(11)
Building Block Questions	736	(1)
InfoTrac College Edition	736	(2)
Carboxylic Acids and Nitriles
Naming Carboxylic Acids and Nitriles	738	(2)
Structure and Physical Properties of Carboxylic Acids	740	(1)
Dissociation of Carboxylic Acids	741	(2)
Substituent Effects on Acidity	743	(2)
Substituent Effects in Substituted Benzoic Acids	745	(1)
Preparation of Carboxylic Acids	746	(3)
Reactions of Carboxylic Acids: An Overview	749	(1)
Reduction of Carboxylic Acids	749	(1)
Chemistry of Nitriles	750	(5)
Spectroscopy of Carboxylic Acids and Nitriles	755	(16)
Chemistry@Work: Vitamin C	757	(1)
Summary and Key Words	758	(1)
Summary of Reactions	759	(2)
Exercises	761	(8)
Building Block Questions	769	(1)
InfoTrac College Edition	769	(2)
Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions
Naming Carboxylic Acid Derivatives	771	(3)
Nucleophilic Acyl Substitution Reactions	774	(5)
Nucleophilic Acyl Substitution Reactions of Carboxylic Acids	779	(4)
Chemistry of Acid Halides	783	(5)
Chemistry of Acid Anhydrides	788	(1)
Chemistry of Esters	789	(6)
Chemistry of Amides	795	(3)
Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives	798	(1)
Polyamides and Polyesters: Step-Growth Polymers	799	(3)
Spectroscopy of Carboxylic Acid Derivatives	802	(19)
Chemistry@Work: β-Lactam Antibiotics	804	(1)
Summary and Key Words	805	(1)
Summary of Reactions	806	(3)
Exercises	809	(10)
Building Block Questions	819	(1)
InfoTrac College Edition	819	(2)
Carbonyl Alpha-Substitution Reactions
Keto-Enol Tautomerism	821	(3)
Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions	824	(1)
Alpha Halogenation of Aldehydes and Ketones	824	(3)
Alpha Bromination of Carboxylic Acids: The Hell-Volhard-Zelinskii Reaction	827	(1)
Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation	828	(4)
Reactivity of Enolate Ions	832	(1)
Halogenation of Enolate Ions: The Haloform Reaction	833	(1)
Alkylation of Enolate Ions	834	(20)
Chemistry@Work: Unusual Elements in Organic Chemistry	842	(2)
Summary and Key Words	844	(1)
Summary of Reactions	844	(2)
Exercises	846	(7)
Building Block Questions	853	(1)
InfoTrac College Edition	853	(1)
Carbonyl Condensation Reactions
Mechanism of Carbonyl Condensation Reactions	854	(1)
Condensations of Aldehydes and Ketones: The Aldol Reaction	855	(3)
Carbonyl Condensation Reactions versus Alpha-Substitution Reactions	858	(1)
Dehydration of Aldol Products: Synthesis of Enones	859	(2)
Using Aldol Reactions in Synthesis	861	(1)
Mixed Aldol Reactions	862	(2)
Intramolecular Aldol Reactions	864	(1)
The Claisen Condensation Reaction	865	(2)
Mixed Claisen Condensations	867	(2)
Intramolecular Claisen Condensations: The Dieckmann Cyclization	869	(2)
The Michael Reaction	871	(3)
The Stork Enamine Reaction	874	(2)
Carbonyl Condensation Reactions in Synthesis: The Robinson Annulation Reaction	876	(2)
Biological Carbonyl Condensation Reactions	878	(14)
Chemistry@Work: A Prologue to Metabolism	878	(2)
Summary and Key Words	880	(1)
Summary of Reactions	881	(2)
Exercises	883	(8)
Building Block Questions	891	(1)
InfoTrac College Edition	891	(1)
Amines
Naming Amines	892	(3)
Structure and Bonding in Amines	895	(1)
Properties and Sources of Amines	896	(1)
Basicity of Amines	897	(4)
Basicity of Substituted Arylamines	901	(2)
Synthesis of Amines	903	(9)
Reactions of Amines	912	(3)
Reactions of Arylamines	915	(6)
Tetraalkylammonium Salts as Phase-Transfer Catalysts	921	(2)
Spectroscopy of Amines	923	(20)
Chemistry@Work: Opium and Opiates	927	(1)
Summary and Key Words	928	(1)
Summary of Reactions	928	(4)
Exercises	932	(9)
Building Block Questions	941	(1)
InfoTrac College Edition	941	(2)
Biomolecules: Carbohydrates
Classification of Carbohydrates	943	(1)
Depicting Carbohydrate Stereochemistry: Fischer Projections	944	(4)
D,L Sugars	948	(1)
Configurations of the Aldoses	949	(3)
Cyclic Structures of Monosaccharides: Hemiacetal Formation	952	(2)
Monosaccharide Anomers: Mutarotation	954	(2)
Reactions of Monosaccharides	956	(7)
Stereochemistry of Glucose: The Fischer Proof	963	(4)
Disaccharides	967	(2)
Polysaccharides and Their Synthesis	969	(3)
Other Important Carbohydrates	972	(1)
Cell-Surface Carbohydrates and Carbohydrate Vaccines	973	(13)
Chemistry@Work: Sweetness	975	(1)
Summary and Key Words	976	(1)
Summary of Reactions	977	(1)
Exercises	978	(6)
Building Block Questions	984	(1)
InfoTrac College Edition	984	(2)
Biomolecules: Amino Acids, Peptides, and Proteins
Structures of Amino Acids	986	(5)
Isoelectric Points	991	(3)
Synthesis of Amino Acids	994	(2)
Enantioselective Synthesis of Amino Acids	996	(2)
Peptides and Proteins	998	(1)
Covalent Bonding in Peptides	999	(1)
Structure Determination of Peptides: Amino Acid Analysis	1000	(1)
Peptide Sequencing: The Edman Degradation	1001	(3)
Peptide Sequencing: C-Terminal Residue Determination	1004	(1)
Peptide Synthesis	1004	(4)
Automated Peptide Synthesis: The Merrifield Solid-Phase Technique	1008	(1)
Protein Classification	1009	(1)
Protein Structure	1010	(2)
Enzymes	1012	(2)
How Do Enzymes Work? Citrate Synthase	1014	(2)
Protein Denaturation	1016	(11)
Chemistry@Work: Protein and Nutrition	1016	(1)
Summary and Key Words	1017	(1)
Summary of Reactions	1018	(2)
Exercises	1020	(6)
Building Block Questions	1026	(1)
InfoTrac College Edition	1026	(1)
Biomolecules: Lipids
Waxes, Fats, and Oils	1027	(3)
Soap	1030	(2)
Phospholipids	1032	(1)
Prostaglandins	1033	(2)
Terpenoids	1035	(3)
Biosynthesis of Terpenoids	1038	(7)
Steroids	1045	(2)
Stereochemistry of Steroids	1047	(2)
Steroid Biosynthesis	1049	(12)
Chemistry@Work: Cholesterol and Heart Disease	1052	(1)
Summary and Key Words	1053	(1)
Exercises	1053	(6)
Building Block Questions	1059	(1)
InfoTrac College Edition	1059	(2)
Biomolecules: Heterocycles and Nucleic Acids
Five-Membered Unsaturated Heterocycles	1061	(1)
Structures of Pyrrole, Furan, and Thiophene	1062	(1)
Electrophilic Substitution Reactions of Pyrrole, Furan, and Thiophene	1063	(1)
Pyridine, a Six-Membered Heterocycle	1064	(1)
Electrophilic Substitution of Pyridine	1065	(1)
Nucleophilic Substitution of Pyridine	1066	(1)
Fused-Ring Heterocycles	1067	(2)
Nucleic Acids and Nucleotides	1069	(2)
Structure of Nucleic Acids	1071	(1)
Base Pairing in DNA: The Watson--Crick Model	1072	(2)
Nucleic Acids and Heredity	1074	(1)
Replication of DNA	1075	(2)
Structure and Synthesis of RNA: Transcription	1077	(1)
RNA and Protein Biosynthesis: Translation	1078	(3)
DNA Sequencing	1081	(2)
DNA Synthesis	1083	(3)
The Polymerase Chain Reaction	1086	(8)
Chemistry@Work: DNA Fingerprinting	1087	(1)
Summary and Key Words	1088	(1)
Summary of Reactions	1089	(1)
Exercises	1090	(3)
Building Block Questions	1093	(1)
InfoTrac College Edition	1093	(1)
The Organic Chemistry of Metabolic Pathways
An Overview of Metabolism and Biochemical Energy	1094	(4)
Catabolism of Fats: β-Oxidation	1098	(6)
Catabolism of Carbohydrates: Glycolysis	1104	(6)
The Conversion of Pyruvate to Acetyl CoA	1110	(3)
The Citric Acid Cycle	1113	(3)
Catabolism of Proteins: Transamination	1116	(2)
Fatty Acid Biosynthesis	1118	(4)
Carbohydrate Biosynthesis: Gluconeogenesis	1122	(3)
Some Conclusions About Biological Chemistry	1125	(9)
Chemistry@Work: Basal Metabolism	1126	(1)
Summary and Key Words	1126	(1)
Exercises	1127	(6)
Building Block Questions	1133	(1)
InfoTrac College Edition	1133	(1)
Orbitals and Organic Chemistry: Pericyclic Reactions
Molecular Orbitals of Conjugated π Systems	1134	(1)
Molecular Orbitals and Pericyclic Reactions	1135	(2)
Electrocyclic Reactions	1137	(2)
Stereochemistry of Thermal Electrocyclic Reactions	1139	(2)
Photochemical Electrocyclic Reactions	1141	(1)
Cycloaddition Reactions	1142	(2)
Stereochemistry of Cycloadditions	1144	(2)
Sigmatropic Rearrangements	1146	(2)
Some Examples of Sigmatropic Rearrangements	1148	(2)
A Summary of Rules for Pericyclic Reactions	1150	(10)
Chemistry@Work: Vitamin D, the Sunshine Vitamin	1151	(1)
Summary and Key Words	1152	(1)
Exercises	1152	(6)
Building Block Questions	1158	(1)
InfoTrac College Edition	1158	(2)
Synthetic Polymers
Chain-Growth Polymers	1160	(1)
Stereochemistry of Polymerization: Ziegler--Natta Catalysts	1161	(2)
Copolymers	1163	(2)
Step-Growth Polymers	1165	(2)
Polymer Structure and Physical Properties	1167
Chemistry@Work: Biodegradable Polymers	1170	(2)
Summary and Key Words	1172	(1)
Exercises	1172	(4)
Building Block Questions	1176	(1)
InfoTrac College Edition	1176
Appendix A: Nomenclature of Polyfunctional Organic Compounds	1	(6)
Appendix B: Acidity Constants for Some Organic Compounds	7	(2)
Appendix C: Glossary	9	(22)
Appendix D: Answers to Selected In-Text Problems	31
Index	1