9780716778745

Organic Chemistry, Solutions Manual/Study Guide & eBook

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  • ISBN13:

    9780716778745

  • ISBN10:

    0716778742

  • Edition: 5th
  • Format: Display
  • Copyright: 2006-03-31
  • Publisher: W. H. Freeman
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Table of Contents

Preface: A User's Guide to Organic Chemistry: Structure and Function xx
Structure and Bonding in Organic Molecules
1(50)
The Scope of Organic Chemistry: An Overview
2(3)
Chemical Highlight 1-1 Saccharin: One of the Oldest Synthetic Organic Compounds in Commercial Use
4(1)
Coulomb Forces: A Simplified View of Bonding
5(2)
Ionic and Covalent Bonds: The Octet Rule
7(7)
Electron-Dot Model of Bonding: Lewis Structures
14(5)
Resonance Forms
19(4)
Atomic Orbitals: A Quantum Mechanical Description of Electrons Around the Nucleus
23(6)
Molecular Orbitals and Covalent Bonding
29(3)
Hybrid Orbitals: Bonding in Complex Molecules
32(6)
Structures and Formulas of Organic Molecules
38(13)
Chapter Integration Problems
41(4)
Important Concepts
45(1)
Problems
46(5)
Structure and Reactivity: Acids and Bases, Polar and Nonpolar Molecules
51(45)
Kinetics and Thermodynamics of Simple Chemical Processes
52(6)
Acids and Bases; Electrophiles and Nucleophiles
58(8)
Chemical Highlight 2-1 Stomach Acid and Food Digestion
59(7)
Functional Groups: Centers of Reactivity
66(3)
Straight-Chain and Branched Alkanes
69(2)
Naming the Alkanes
71(5)
Structural and Physical Properties of Alkanes
76(3)
Rotation about Single Bonds: Conformations
79(4)
Chemical Highlight 2-2 ``Sexual Swindle'' by Means of Chemical Mimicry
79(4)
Rotation in Substituted Ethanes
83(13)
Chapter Integration Problems
87(2)
Important Concepts
89(1)
Problems
90(6)
Reactions of Alkanes: Bond-Dissociation Energies, Radical Halogenation, and Relative Reactivity
96(35)
Strength of Alkane Bonds: Radicals
97(3)
Structure of Alkyl Radicals: Hyperconjugation
100(1)
Conversion of Petroleum: Pyrolysis
101(4)
Chemical Highlight 3-1 Petroleum and Gasoline: Our Main Energy Sources
104(1)
Chlorination of Methane: The Radical Chain Mechanism
105(5)
Other Radical Halogenations of Methane
110(2)
Chlorination of Higher Alkanes: Relative Reactivity and Selectivity
112(4)
Selectivity in Radical Halogenation with Fluorine and Bromine
116(2)
Synthetic Radical Halogenation
118(1)
Synthetic Chlorine Compounds and the Stratospheric Ozone Layer
119(3)
Chemical Highlight 3-2 Chlorination, Chloral, and DDT
119(3)
Combustion and the Relative Stabilities of Alkanes
122(9)
Chapter Integration Problems
124(2)
Important Concepts
126(1)
Problems
127(4)
Cycloalkanes
131(37)
Names and Physical Properties of Cycloalkanes
132(2)
Ring Strain and the Structure of Cycloalkanes
134(5)
Cyclohexane: A Strain-Free Cycloalkane
139(5)
Substituted Cyclohexanes
144(4)
Larger Cycloalkanes
148(1)
Polycyclic Alkanes
149(2)
Carbocyclic Products in Nature
151(17)
Chemical Highlight 4-1 Cubane Derivatives with Potential as Explosives: Octanitrocubane
151(4)
Chemical Highlight 4-2 Cholesterol: How Is It Bad and How Bad Is It?
155(1)
Chemical Highlight 4-3 Controlling Fertility: From ``the Pill'' to RU-486
156(2)
Chapter Integration Problems
158(3)
Important Concepts
161(1)
Problems
162(6)
Stereoisomers
168(47)
Chiral Molecules
170(4)
Chemical Highlight 5-1 Chiral Substances in Nature
173(1)
Optical Activity
174(3)
Absolute Configuration: R--S Sequence Rules
177(5)
Chemical Highlight 5-2 Absolute Configuration: A Historical Note
181(1)
Fischer Projections
182(4)
Molecules Incorporating Several Stereocenters: Diastereomers
186(4)
Chemical Highlight 5-3 Stereoisomers of Tartaric Acid
189(1)
Meso Compounds
190(2)
Stereochemistry in Chemical Reactions
192(9)
Chemical Highlight 5-4 Chiral Drugs: Racemic or Enantiomerically Pure?
194(4)
Chemical Highlight 5-5 Why Is Nature ``Handed''?
198(3)
Resolution: Separation of Enantiomers
201(14)
Chapter Integration Problems
204(2)
Important Concepts
206(1)
Problems
207(8)
Properties and Reactions of Haloalkanes: Bimolecular Nucleophilic Substitution
215(35)
Physical Properties of Haloalkanes
215(3)
Chemical Highlight 6-1 Halogenated Steroids as Anti-Inflammatory and Anti-Asthmatic Agents
217(1)
Nucleophilic Substitution
218(3)
Reaction Mechanisms Involving Polar Functional Groups: Using ``Electron-Pushing'' Arrows
221(2)
A Closer Look at the Nucleophilic Substitution Mechanism: Kinetics
223(3)
Frontside or Backside Attack? Stereochemistry of the SN2 Reaction
226(2)
Consequences of Inversion in SN2 Reactions
228(3)
Structure and SN2 Reactivity: The Leaving Group
231(1)
Structure and SN2 Reactivity: The Nucleophile
232(7)
Structure and SN2 Reactivity: The Substrate
239(11)
Chemical Highlight 6-2 The Dilemma of Bromomethane: Highly Useful but Also Highly Toxic
240(3)
Chapter Integration Problems
243(2)
Important Concepts
245(1)
Problems
245(5)
Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination
250(35)
Solvolysis of Tertiary and Secondary Haloalkanes
250(2)
Unimolecular Nucleophilic Substitution
252(3)
Stereochemical Consequences of SN1 Reactions
255(1)
Effects of Solvent, Leaving Group, and Nucleophile on Unimolecular Substitution
256(2)
Effect of the Alkyl Group on the SN1 Reaction: Carbocation Stability
258(4)
Chemical Highlight 7-1 Unusually Stereoselective SN1 Displacement in Anticancer Drug Synthesis
261(1)
Unimolecular Elimination: E1
262(3)
Bimolecular Elimination: E2
265(3)
Competition Between Substitution and Elimination: Structure Determines Function
268(3)
Summary of Reactivity of Haloalkanes
271(14)
Chapter Integration Problems
273(2)
New Reactions
275(1)
Important Concepts
276(1)
Problems
276(9)
Hydroxy Functional Group: Alcohols: Properties, Preparation, and Strategy of Synthesis
285(47)
Naming the Alcohols
286(1)
Structural and Physical Properties of Alcohols
287(3)
Alcohols as Acids and Bases
290(3)
Industrial Sources of Alcohols: Carbon Monoxide and Ethene
293(1)
Synthesis of Alcohols by Nucleophilic Substitution
294(1)
Synthesis of Alcohols: Oxidation--Reduction Relation Between Alcohols and Carbonyl Compounds
295(8)
Chemical Highlight 8-1 Biological Oxidation and Reduction
298(3)
Chemical Highlight 8-2 The Breath Analyzer Test
301(2)
Organometallic Reagents: Sources of Nucleophilic Carbon for Alcohol Synthesis
303(3)
Organometallic Reagents in the Synthesis of Alcohols
306(3)
Chemical Highlight 8-3 Transition Metal-Catalyzed Cross-Coupling Reactions
308(1)
Complex Alcohols: An Introduction to Synthetic Strategy
309(23)
Chapter Integration Problems
318(3)
New Reactions
321(4)
Important Concepts
325(1)
Problems
325(7)
Further Reactions of Alcohols and the Chemistry of Ethers
332(55)
Reactions of Alcohols with Base: Preparation of Alkoxides
333(1)
Reactions of Alcohols with Strong Acids: Alkyloxonium Ions in Substitution and Elimination Reactions of Alcohols
334(3)
Carbocation Rearrangements
337(5)
Organic and Inorganic Esters from Alcohols
342(4)
Names and Physical Properties of Ethers
346(3)
Williamson Ether Synthesis
349(5)
Chemical Highlight 9-1 Chemiluminescence of 1,2-Dioxacyclobutanes
350(4)
Synthesis of Ethers: Alcohols and Mineral Acids
354(1)
Reactions of Ethers
355(3)
Chemical Highlight 9-2 Protecting Groups in Synthesis
357(1)
Reactions of Oxacyclopropanes
358(6)
Chemical Highlight 9-3 Hydrolytic Kinetic Resolution of Oxacyclopropanes
360(4)
Sulfur Analogs of Alcohols and Ethers
364(3)
Physiological Properties and Uses of Alcohols and Ethers
367(20)
Chemical Highlight 9-4 Garlic and Sulfur
370(1)
Chapter Integration Problems
371(3)
New Reactions
374(2)
Important Concepts
376(1)
Problems
377(10)
Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure
387(59)
Physical and Chemical Tests
388(1)
Defining Spectroscopy
388(3)
Hydrogen Nuclear Magnetic Resonance
391(5)
Chemical Highlight 10-1 Recording an NMR Spectrum
394(2)
Using NMR Spectra to Analyze Molecular Structure: The Proton Chemical Shift
396(5)
Tests for Chemical Equivalence
401(4)
Chemical Highlight 10-2 Magnetic Resonance Imaging in Medicine
404(1)
Integration
405(2)
Spin--Spin Splitting: The Effect of Nonequivalent Neighboring Hydrogens
407(8)
Spin--Spin Splitting: Some Complications
415(7)
Chemical Highlight 10-3 The Nonequivalence of Diastereotopic Hydrogens
418(4)
Carbon-13 Nuclear Magnetic Resonance
422(24)
Chemical Highlight 10-4 Correlated NMR Spectra: COSY and HETCOR
428(2)
Chemical Highlight 10-5 Structural Characterization of Natural Products: Antioxidants from Grape Seeds
430(2)
Chapter Integration Problems
432(3)
Important Concepts
435(1)
Problems
436(10)
Alkenes; Infrared Spectroscopy and Mass Spectrometry
446(54)
Naming the Alkenes
447(3)
Structure and Bonding in Ethene: The Pi Bond
450(3)
Physical Properties of Alkenes
453(1)
Nuclear Magnetic Resonance of Alkenes
454(6)
Chemical Highlight 11-1 Prostaglandins
459(1)
Infrared Spectroscopy
460(4)
Measuring the Molecular Mass of Organic Compounds: Mass Spectrometry
464(4)
Fragmentation Patterns of Organic Molecules
468(5)
Degree of Unsaturation: Another Aid to Identifying Molecular Structure
473(2)
Catalytic Hydrogenation of Alkenes: Relative Stability of Double Bonds
475(2)
Preparation of Alkenes from Haloalkanes and Alkyl Sulfonates: Bimolecular Elimination Revisited
477(4)
Preparation of Alkenes by Dehydration of Alcohols
481(19)
Chemical Highlight 11-2 Acid-Catalyzed Dehydration of α-Terpineol
483(1)
Chapter Integration Problems
484(2)
New Reactions
486(1)
Important Concepts
487(1)
Problems
488(12)
Reactions of Alkenes
500(61)
Why Addition Reactions Proceed: Thermodynamic Feasibility
501(1)
Catalytic Hydrogenation
501(3)
Nucleophilic Character of the Pi Bond: Electrophilic Addition of Hydrogen Halides
504(4)
Alcohol Synthesis by Electrophilic Hydration: Thermodynamic Control
508(2)
Electrophilic Addition of Halogens to Alkenes
510(3)
The Generality of Electrophilic Addition
513(3)
Oxymercuration--Demercuration: A Special Electrophilic Addition
516(4)
Chemical Highlight 12-1 Juvenile Hormone Analogs in the Battle against Insect-Borne Diseases
517(3)
Hydroboration--Oxidation: A Stereospecific Anti-Markovnikov Hydration
520(2)
Diazomethane, Carbenes, and Cyclopropane Synthesis
522(2)
Oxacyclopropane (Epoxide) Synthesis: Epoxidation by Peroxycarboxylic Acids
524(2)
Vicinal Syn Dihydroxylation with Osmium Tetroxide
526(3)
Chemical Highlight 12-2 Enantioselective Dihydroxylation in the Synthesis of Antitumor Drugs
528(1)
Oxidative Cleavage: Ozonolysis
529(2)
Radical Additions: Anti-Markovnikov Product Formation
531(2)
Dimerization, Oligomerization, and Polymerization of Alkenes
533(2)
Synthesis of Polymers
535(5)
Chemical Highlight 12-3 Polymers in the Clean-Up of Oil Spills
536(2)
Chemical Highlight 12-4 Polymer-Supported Synthesis of Chemical Libraries
538(2)
Ethene: An Important Industrial Feedstock
540(1)
Alkenes in Nature: Insect Pheromones
541(20)
Chemical Highlight 12-5 Metal-Catalyzed Alkene Metathesis for Constructing Medium and Large Rings
542(2)
Chapter Integration Problems
544(2)
New Reactions
546(3)
Important Concepts
549(1)
Problems
550(11)
Alkynes: The Carbon-Carbon Triple Bond
561(41)
Naming the Alkynes
562(1)
Properties and Bonding in the Alkynes
563(2)
Spectroscopy of the Alkynes
565(5)
Preparation of Alkynes by Double Elimination
570(1)
Preparation of Alkynes from Alkynyl Anions
571(1)
Reduction of Alkynes: The Relative Reactivity of the Two Pi Bonds
572(4)
Electrophilic Addition Reactions of Alkynes
576(3)
Anti-Markovnikov Additions to Triple Bonds
579(1)
Chemistry of Alkenyl Halides
580(2)
Ethyne as an Industrial Starting Material
582(3)
Chemical Highlight 13-1 Metal-Catalyzed Stille, Suzuki, and Sonogashira Coupling Reactions
582(3)
Naturally Occurring and Physiologically Active Alkynes
585(17)
Chapter Integration Problems
588(1)
New Reactions
589(4)
Important Concepts
593(1)
Problems
593(9)
Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy
602(63)
Overlap of Three Adjacent p Orbitals: Electron Delocalization in the 2-Propenyl (Allyl) System
603(3)
Radical Allylic Halogenation
606(1)
Nucleophilic Substitution of Allylic Halides: SN1 and SN2
607(2)
Allylic Organometallic Reagents: Useful Three-Carbon Nucleophiles
609(1)
Two Neighboring Double Bonds: Conjugated Dienes
610(4)
Electrophilic Attack on Conjugated Dienes: Kinetic and Thermodynamic Control
614(4)
Chemical Highlight 14-1 Use of a Fungicidal Diene in Making Wine: Sorbic Acid
615(3)
Delocalization among More than Two Pi Bonds: Extended Conjugation and Benzene
618(2)
A Special Transformation of Conjugated Dienes: Diels-Alder Cycloaddition
620(12)
Chemical Highlight 14-2 Conducting Organic Polymers: Materials for the Future?
622(6)
Chemical Highlight 14-3 The Diels-Alder Reaction is ``Green''
628(4)
Electrocyclic Reactions
632(6)
Chemical Highlight 14-4 An Extraordinary Electrocyclic Reaction of Anticancer Agents
636(2)
Polymerization of Conjugated Dienes: Rubber
638(4)
Electronic Spectra: Ultraviolet and Visible Spectroscopy
642(23)
Chemical Highlight 14-5 The Contributions of IR, MS, and UV to the Characterization of Viniferone
647(1)
Chapter Integration Problems
648(3)
New Reactions
651(2)
Important Concepts
653(1)
Problems
653(7)
Interlude: A Summary of Organic Reaction Mechanisms
660(5)
Benzene and Aromaticity: Electrophilic Aromatic Substitution
665(56)
Naming the Benzenes
667(2)
Structure and Resonance Energy of Benzene: A First Look at Aromaticity
669(3)
Pi Molecular Orbitals of Benzene
672(2)
Spectral Characteristics of the Benzene Ring
674(5)
Polycyclic Aromatic Hydrocarbons
679(6)
Chemical Highlight 15-1 The Allotropes of Carbon: Graphite, Diamond, and Fullerenes
680(5)
Other Cyclic Polyenes: Huckel's Rule
685(5)
Chemical Highlight 15-2 Juxtaposing Aromatic and Antiaromatic Rings in Fused Hydrocarbons
686(4)
Huckel's Rule and Charged Molecules
690(2)
Synthesis of Benzene Derivatives: Electrophilic Aromatic Substitution
692(3)
Halogenation of Benzene: The Need for a Catalyst
695(1)
Nitration and Sulfonation of Benzene
696(3)
Friedel-Crafts Alkylation
699(3)
Limitations of Friedel-Crafts Alkylations
702(2)
Friedel-Crafts Alkanoylation (Acylation)
704(17)
Chapter Integration Problems
708(3)
New Reactions
711(2)
Important Concepts
713(1)
Problems
713(8)
Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity
721(42)
Activation or Deactivation by Substituents on a Benzene Ring
722(2)
Directing Inductive Effects of Alkyl Groups
724(4)
Directing Effects of Substituents in Conjugation with the Benzene Ring
728(7)
Chemical Highlight 16-1 Explosive Nitroarenes: TNT and Picric Acid
731(4)
Electrophilic Attack on Disubstituted Benzenes
735(3)
Synthetic Strategies Toward Substituted Benzenes
738(6)
Reactivity of Polycyclic Benzenoid Hydrocarbons
744(4)
Polycyclic Aromatic Hydrocarbons and Cancer
748(15)
Chapter Integration Problems
750(3)
New Reactions
753(1)
Important Concepts
754(1)
Problems
755(8)
Aldehydes and Ketones: The Carbonyl Group
763(51)
Naming the Aldehydes and Ketones
764(2)
Structure of the Carbonyl Group
766(2)
Spectroscopic Properties of Aldehydes and Ketones
768(5)
Preparation of Aldehydes and Ketones
773(2)
Reactivity of the Carbonyl Group: Mechanisms of Addition
775(3)
Addition of Water to Form Hydrates
778(1)
Addition of Alcohols to Form Hemiacetals and Acetals
779(3)
Acetals as Protecting Groups
782(2)
Nucleophilic Addition of Ammonia and Its Derivatives
784(5)
Chemical Highlight 17-1 Imines in Biological Transformations
786(3)
Deoxygenation of the Carbonyl Group
789(2)
Addition of Hydrogen Cyanide to Give Cyanohydrins
791(1)
Addition of Phosphorus Ylides: The Wittig Reaction
792(3)
Chemical Highlight 17-2 The Wittig Reaction in Synthesis
794(1)
Oxidation by Peroxycarboxylic Acids: The Baeyer-Villiger Oxidation
795(1)
Oxidative Chemical Tests for Aldehydes
796(18)
Chapter Integration Problems
798(2)
New Reactions
800(3)
Important Concepts
803(1)
Problems
803(11)
Enols, Enolates, and the Aldol Condensation: α, β-Unsaturated Aldehydes and Ketones
814(42)
Acidity of Aldehydes and Ketones: Enolate Ions
815(1)
Keto--Enol Equilibria
816(3)
Halogenation of Aldehydes and Ketones
819(2)
Alkylation of Aldehydes and Ketones
821(3)
Attack by Enolates on the Carbonyl Function: Aldol Condensation
824(4)
Crossed Aldol Condensation
828(2)
Chemical Highlight 18-1 Enzyme-Catalyzed Stereoselective Aldol Condensations in Nature
829(1)
Intramolecular Aldol Condensation
830(2)
Chemical Highlight 18-2 Enzymes in Synthesis: Stereoselective Crossed Aldol Condensations
830(2)
Properties of α,β-Unsaturated Aldehydes and Ketones
832(2)
Chemical Highlight 18-3 Reactions of Unsaturated Aldehydes in Nature: The Chemistry of Vision
832(2)
Conjugate Additions to α,β-Unsaturated Aldehydes and Ketones
834(2)
1,2- and 1,4-Additions of Organometallic Reagents
836(3)
Conjugate Additions of Enolate Ions: Michael Addition and Robinson Annulation
839(17)
Chemical Highlight 18-4 Prostaglandins: α,β-Dialkylation in Synthesis
840(1)
Chapter Integration Problems
841(3)
New Reactions
844(3)
Important Concepts
847(1)
Problems
847(9)
Carboxylic Acids
856(53)
Naming the Carboxylic Acids
857(2)
Structural and Physical Properties of Carboxylic Acids
859(2)
Chemical Highlight 19-1 Toxicity of Oxalic Acid
859(2)
Spectroscopy and Mass Spectrometry of Carboxylic Acids
861(3)
Acidic and Basic Character of Carboxylic Acids
864(3)
Carboxylic Acid Synthesis in Industry
867(1)
Methods for Introducing the Carboxy Functional Group
867(3)
Substitution at the Carboxy Carbon: The Addition--Elimination Mechanism
870(3)
Carboxylic Acid Derivatives: Alkanoyl (Acyl) Halides and Anhydrides
873(3)
Carboxylic Acid Derivatives: Esters
876(4)
Carboxylic Acid Derivatives: Amides
880(2)
Reduction of Carboxylic Acids by Lithium Aluminum Hydride
882(1)
Bromination Next to the Carboxy Group: The Hell-Volhard-Zelinsky Reaction
882(2)
Biological Activity of Carboxylic Acids
884(25)
Chemical Highlight 19-2 Soaps from Long-Chain Carboxylates
885(2)
Chemical Highlight 19-3 Trans Fatty Acids and Your Health
887(2)
Chemical Highlight 19-4 Biodegradable Polyester Plastics
889(2)
Chapter Integration Problems
891(3)
New Reactions
894(3)
Important Concepts
897(1)
Problems
897(12)
Carboxylic Acid Derivatives
909(47)
Relative Reactivities, Structures, and Spectra of Carboxylic Acid Derivatives
910(4)
Chemistry of Alkanoyl Halides
914(4)
Chemistry of Carboxylic Anhydrides
918(1)
Chemistry of Esters
919(5)
Esters in Nature: Waxes, Fats, Oils, and Lipids
924(4)
Chemical Highlight 20-1 Alternatives to Petroleum: Fuels from Vegetable Oil
926(2)
Amides: The Least Reactive Carboxylic Acid Derivatives
928(5)
Chemical Highlight 20-2 Battling the Bugs: Antibiotic Wars
930(3)
Amidates and Their Halogenation: The Hofmann Rearrangement
933(4)
Chemical Highlight 20-3 Methyl Isocyanate, Carbamate-based Insecticides, and Safety in the Chemical Industry
936(1)
Alkanenitriles: A Special Class of Carboxylic Acid Derivatives
937(19)
Chapter Integration Problems
941(3)
New Reactions
944(4)
Important Concepts
948(1)
Problems
948(8)
Amines and Their Derivatives: Functional Groups Containing Nitrogen
956(45)
Naming the Amines
957(1)
Structural and Physical Properties of Amines
958(4)
Chemical Highlight 21-1 Physiologically Active Amines and Weight Control
960(2)
Spectroscopy of the Amine Group
962(3)
Acidity and Basicity of Amines
965(4)
Chemical Highlight 21-2 Separation of Amines from Other Organic Compounds by Aqueous Extraction Techniques
968(1)
Synthesis of Amines by Alkylation
969(3)
Synthesis of Amines by Reductive Amination
972(3)
Synthesis of Amines from Carboxylic Amides
975(1)
Quaternary Ammonium Salts: Hofmann Elimination
975(2)
Mannich Reaction: Alkylation of Enols by Iminium Ions
977(2)
Nitrosation of Amines
979(22)
Chemical Highlight 21-3 N-Nitrosodialkanamines and Cancer
980(2)
Chemical Highlight 21-4 Amines in Industry: Nylon
982(3)
Chapter Integration Problems
985(3)
New Reactions
988(5)
Important Concepts
993(1)
Problems
993(8)
Chemistry of Benzene Substituents: Alkylbenzenes, Phenols, and Benzenamines
1001(60)
Reactivity at the Phenylmethyl (Benzyl) Carbon: Benzylic Resonance Stabilization
1002(4)
Benzylic Oxidations and Reductions
1006(3)
Names and Properties of Phenols
1009(4)
Chemical Highlight 22-1 Two Phenols in the News: Bisphenol A and Resveratrol
1012(1)
Preparation of Phenols: Nucleophilic Aromatic Substitution
1013(9)
Alcohol Chemistry of Phenols
1022(2)
Chemical Highlight 22-2 Aspirin: A Phenyl Alkanoate Drug
1023(1)
Electrophilic Substitution of Phenols
1024(4)
An Electrocyclic Reaction of the Benzene Ring: The Claisen Rearrangement
1028(2)
Oxidation of Phenols: Benzoquinones
1030(3)
Chemical Highlight 22-3 Chemical Warfare in Nature: The Bombardier Beetle
1032(1)
Oxidation-Reduction Processes in Nature
1033(5)
Arenediazonium Salts
1038(3)
Electrophilic Substitution with Arenediazonium Salts: Diazo Coupling
1041(20)
Chemical Highlight 22-4 William Perkin and the Origins of Industrial and Medicinal Chemistry
1042(2)
Chapter Integration Problems
1044(2)
New Reactions
1046(6)
Important Concepts
1052(1)
Problems
1052(9)
Ester Enolates and the Claisen Condensation: Synthesis of β-Dicarbonyl Compounds: Acyl Anion Equivalents
1061(35)
β-Dicarbonyl Compounds: Claisen Condensations
1062(7)
Chemical Highlight 23-1 Claisen Condensations in Biochemistry
1066(3)
β-Dicarbonyl Compounds as Synthetic Intermediates
1069(5)
β-Dicarbonyl Anion Chemistry: Michael Additions
1074(2)
Alkanoyl (Acyl) Anion Equivalents: Preparation of α-Hydroxyketones
1076(20)
Chemical Highlight 23-2 Thiamine: A Natural, Metabolically Active Thiazolium Salt
1080(3)
Chapter Integration Problems
1083(4)
New Reactions
1087(1)
Important Concepts
1088(1)
Problems
1089(7)
Carbohydrates: Polyfunctional Compounds in Nature
1096(49)
Names and Structures of Carbohydrates
1097(4)
Conformations and Cyclic Forms of Sugars
1101(4)
Anomers of Simple Sugars: Mutarotation of Glucose
1105(2)
Polyfunctional Chemistry of Sugars: Oxidation to Carboxylic Acids
1107(2)
Oxidative Cleavage of Sugars
1109(1)
Reduction of Monosaccharides to Alditols
1110(1)
Carbonyl Condensations with Amine Derivatives
1111(1)
Ester and Ether Formation: Glycosides
1112(4)
Chemical Highlight 24-1 18F-Labeled Glucose as a Radiotracer: Imaging the Human Brain
1113(2)
Chemical Highlight 24-2 Protecting Groups in Vitamin C Synthesis
1115(1)
Step-by-Step Buildup and Degradation of Sugars
1116(4)
Chemical Highlight 24-3 Sugar Biochemistry
1118(2)
Relative Configurations of the Aldoses: An Exercise in Structure Determination
1120(2)
Complex Sugars in Nature: Disaccharides
1122(5)
Chemical Highlight 24-4 Carbohydrate-Derived Sugar Substitutes
1124(3)
Polysaccharides and Other Sugars in Nature
1127(18)
Chapter Integration Problem
1133(2)
New Reactions
1135(3)
Important Concepts
1138(1)
Problems
1139(6)
Heterocycles: Heteroatoms in Cyclic Organic Compounds
1145(46)
Naming the Heterocycles
1148(1)
Nonaromatic Heterocycles
1149(4)
Chemical Highlight 25-1 Azacyclopropene Antibiotics
1150(2)
Chemical Highlight 25-2 Smoking, Nicotine, and Cancer
1152(1)
Structure and Properties of Aromatic Heterocyclopentadienes
1153(3)
Reactions of the Aromatic Heterocyclopentadienes
1156(4)
Structure and Preparation of Pyridine: An Azabenzene
1160(4)
Reactions of Pyridine
1164(3)
Chemical Highlight 25-3 Pyridinium Salts in Nature: Nicotinamide Adenine Dinucleotide
1166(1)
Quinoline and Isoquinoline: The Benzopyridines
1167(3)
Chemical Highlight 25-4 Azanaphthalenes in Nature
1168(2)
Alkaloids: Physiologically Potent Nitrogen Heterocycles in Nature
1170(21)
Chemical Highlight 25-5 Nature Is Not Always Green: Natural Pesticides
1172(2)
Chapter Integration Problems
1174(4)
New Reactions
1178(2)
Important Concepts
1180(1)
Problems
1180(11)
Amino Acids, Peptides, Proteins, and Nucleic Acids: Nitrogen-Containing Polymers in Nature
1191
Structure and Properties of Amino Acids
1192(6)
Chemical Highlight 26-1 Arginine and Nitric Oxide in Biochemistry and Medicine
1197(1)
Synthesis of Amino Acids: A Combination of Amine and Carboxylic Acid Chemistry
1198(3)
Synthesis of Enantiomerically Pure Amino Acids
1201(2)
Chemical Highlight 26-2 Synthesis of Optically Pure Amino Acids: Phase-Transfer Catalysis
1202(1)
Peptides and Proteins: Amino Acid Oligomers and Polymers
1203(8)
Determination of Primary Structure: Amino Acid Sequencing
1211(5)
Synthesis of Polypeptides: A Challenge in the Application of Protecting Groups
1216(3)
Merrifield Solid-Phase Peptide Synthesis
1219(2)
Polypeptides in Nature: Oxygen Transport by the Proteins Myoglobin and Hemoglobin
1221(2)
Biosynthesis of Proteins: Nucleic Acids
1223(5)
Chemical Highlight 26-3 Synthetic Nucleic Acid Bases and Nucleosides in Medicine
1225(3)
Protein Synthesis Through RNA
1228(3)
DNA Sequencing and Synthesis: Cornerstones of Gene Technology
1231
Chemical Highlight 26-4 DNA Fingerprinting
1238(5)
Chapter Integration Problems
1243(3)
New Reactions
1246(1)
Important Concepts
1247(1)
Problems
1248
MCAT® Questions 1(1)
Answers to Exercises 1(1)
Photograph Credits 1(1)
Index 1

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