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Organic Chemistry With Infotrac

ISBN: 9780534389994 | 0534389996
Edition: 6th
Format: Paperback
Publisher: Brooks Cole
Pub. Date: 3/21/2003

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SummaryTable of Contents
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." Th... MORE
... MORE
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 Compounds1(6)
Appendix B: Acidity Constants for Some Organic Compounds7(2)
Appendix C: Glossary9(22)
Appendix D: Answers to Selected In-Text Problems31
Index1

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