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ORGANIC CHEMISTRY (TEXT)

by:
ISBN: 9780072905014 | 0072905018
Edition: 4TH
Publisher: MCG
Pub. Date: 1/1/2000

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SummaryTable of Contents
"A Market Leading, Traditional Approach to Organic Chemistry" Throughout all seven editions, Organic Chemistry has been designed to meet the needs of the "mainstream," two-semester, undergraduate organic chemistry course. This best-selling text gives students a solid understanding of organic chemistry by stressing how fundamental reaction mechanisms function and reactions occur. With the addition of handwritten solutions, new cutting-edge molecular illustrations, updated spectroscopy coverage, seamless integration of molecular modeling exercises, and state-of-the-art multimedia tools, the 7th edition of Organic Chemistry clearly offers the most up-to-date approach to the study of organic chemistry.
Prefacexxv
Introduction1(1)
The Origins of Organic Chemistry
1(1)
Berzelius, Wohler, and Vitalism
... MORE1(2)
The Structural Theory
3(1)
Electronic Theories of Structure and Reactivity
3(1)
The Influence of Organic Chemistry
4(1)
Computers and Organic Chemistry
4(1)
Challenges and Opportunities
5(1)
Where Did the Carbon Come From?
6(1)
Chemical Bonding
7(46)
Atoms, Electrons, and Orbitals
7(4)
Ionic Bonds
11(1)
Covalent Bonds
12(2)
Double Bonds and Triple Bonds
14(1)
Polar Covalent Bonds and Electronegativity
15(1)
Formal Charge
16(3)
Structural Formulas of Organic Molecules
19(3)
Constitutional Isomers
22(1)
Resonance
23(3)
The Shapes of Some Simple Molecules
26(4)
Learning By Modeling
27(3)
Molecular Dipole Moments
30(1)
Electron Waves and Chemical Bonds
31(1)
Bonding in H2: The Valence Bond Model
32(2)
Bonding in H2: The Molecular Orbital Model
34(1)
Bonding in Methane and Orbital Hybridization
35(2)
sp3 Hybridization and Bonding in Ethane
37(1)
sp2 Hybridization and Bonding in Ethylene
38(2)
sp Hybridization and Bonding in Acetylene
40(2)
Which Theory of Chemical Bonding Is Best?
42(1)
Summary
43(10)
Problems
47(6)
Alkanes
53(36)
Classes of Hydrocarbons
53(1)
Reactive Sites in Hydrocarbons
54(1)
The Key Functional Groups
55(1)
Introduction to Alkanes: Methane, Ethane, and Propane
56(1)
Isomeric Alkanes: The Butanes
57(2)
Methane and the Biosphere
58(1)
Higher n-Alkanes
59(1)
The C5H12 Isomers
59(2)
IUPAC Nomenclature of Unbranched Alkanes
61(1)
Applying the IUPAC Rules: The Names of the C6H14 Isomers
62(3)
A Brief History of Systematic Organic Nomenclature
63(2)
Alkyl Groups
65(1)
IUPAC Names of Highly Branched Alkanes
66(2)
Cycloalkane Nomenclature
68(1)
Sources of Alkanes and Cycloalkanes
69(2)
Physical Properties of Alkanes and Cycloalkanes
71(3)
Chemical Properties. Combustion of Alkanes
74(4)
Thermochemistry
77(1)
Oxidation-Reduction in Organic Chemistry
78(2)
Summary
80(9)
Problems
83(6)
Conformations of Alkanes and Cycloalkanes
89(37)
Conformational Analysis of Ethane
90(4)
Conformational Analysis of Butane
94(3)
Molecular Mechanics Applied to Alkanes and Cycloalkanes
96(1)
Conformations of Higher Alkanes
97(1)
The Shapes of Cycloalkanes: Planar or Nonplanar?
98(1)
Conformations of Cyclohexane
99(1)
Axial and Equatorial Bonds in Cyclohexane
100(3)
Conformational Inversion (Ring Flipping) in Cyclohexane
103(1)
Conformational Analysis of Monosubstituted Cyclohexanes
104(2)
Enthalpy, Free Energy, and Equilibrium Constant
106(1)
Small Rings: Cyclopropane and Cyclobutane
106(2)
Cyclopentane
108(1)
Medium and Large Rings
108(1)
Disubstituted Cycloalkanes: Stereoisomers
108(2)
Conformational Analysis of Disubstituted Cyclohexanes
110(4)
Polycyclic Ring Systems
114(2)
Heterocyclic Compounds
116(1)
Summary
117(9)
Problems
120(6)
Alcohols and Alkyl Halides
126(41)
IUPAC Nomenclature of Alkyl Halides
127(1)
IUPAC Nomenclature of Alcohols
127(1)
Classes of Alcohols and Alkyl Halides
128(1)
Bonding in Alcohols and Alkyl Halides
129(1)
Physical Properties of Alcohols and Alkyl Halides: Intermolecular Forces
130(3)
Acids and Bases: General Principles
133(3)
Acid-Base Reactions: A Mechanism for Proton Transfer
136(1)
Preparation of Alkyl Halides from Alcohols and Hydrogen Halides
137(2)
Mechanism of the Reaction of Alcohols with Hydrogen Halides
139(1)
Structure, Bonding, and Stability of Carbocations
140(3)
Potential Energy Diagrams for Multistep Reactions: The SN1 Mechanism
143(2)
Effect of Alcohol Structure on Reaction Rate
145(1)
Reaction of Primary Alcohols with Hydrogen Halides: The SN2 Mechanism
146(1)
Other Methods for Converting Alcohols to Alkyl Halides
147(1)
Halogenation of Alkanes
148(1)
Chlorination of Methane
148(1)
Structure and Stability of Free Radicals
149(4)
Mechanism of Methane Chlorination
153(3)
From Bond Energies to Heats of Reaction
155(1)
Halogenation of Higher Alkanes
156(3)
Summary
159(8)
Problems
163(4)
Structure and Preparation of Alkenes: Elimination Reactions
167(41)
Alkene Nomenclature
167(3)
Ethylene
168(2)
Structure and Bonding in Alkenes
170(2)
Isomerism in Alkenes
172(1)
Naming Stereoisomeric Alkenes by the E-Z Notational System
173(1)
Physical Properties of Alkenes
174(2)
Relative Stabilities of Alkenes
176(4)
Cycloalkenes
180(1)
Preparation of Alkenes: Elimination Reactions
181(1)
Dehydration of Alcohols
182(1)
Regioselectivity in Alcohol Dehydration: The Zaitsev Rule
183(1)
Stereoselectivity in Alcohol Dehydration
184(1)
The Mechanism of Acid-Catalyzed Dehydration of Alcohols
185(2)
Rearrangements in Alcohol Dehydration
187(3)
Dehydrohalogenation of Alkyl Halides
190(2)
Mechanism of the Dehydrohalogenation of Alkyl Halides: The E2 Mechanism
192(2)
Anti Elimination in E2 Reactions: Stereoelectronic Effects
194(2)
A Different Mechanism for Alkyl Halide Elimination: The E1 Mechanism
196(2)
Summary
198(10)
Problems
202(6)
Reactions of Alkenes: Addition Reactions
208(51)
Hydrogenation of Alkenes
208(1)
Heats of Hydrogenation
209(3)
Stereochemistry of Alkene Hydrogenation
212(1)
Electrophilic Addition of Hydrogen Halides to Alkenes
213(1)
Regioselectivity of Hydrogen Halide Addition: Markovnikov's Rule
214(2)
Mechanistic Basis for Markovnikov's Rule
216(3)
Rules, Laws, Theories, and the Scientific Method
217(2)
Carbocation Rearrangements in Hydrogen Halide Addition to Alkenes
219(1)
Free-Radical Addition of Hydrogen Bromide to Alkenes
220(3)
Addition of Sulfuric Acid to Alkenes
223(2)
Acid-Catalyzed Hydration of Alkenes
225(2)
Hydroboration-Oxidation of Alkenes
227(2)
Stereochemistry of Hydroboration-Oxidation
229(1)
Mechanism of Hydroboration-Oxidation
230(3)
Addition of Halogens to Alkenes
233(1)
Stereochemistry of Halogen Addition
233(1)
Mechanism of Halogen Addition to Alkenes: Halonium Ions
234(2)
Conversion of Alkenes to Vicinal Halohydrins
236(2)
Epoxidation of Alkenes
238(2)
Ozonolysis of Alkenes
240(3)
Introduction to Organic Chemical Synthesis
243(1)
Reactions of Alkenes with Alkenes: Polymerization
244(5)
Ethylene and Propene: The Most Important Industrial Organic Chemicals
248(1)
Summary
249(10)
Problems
252(7)
Stereochemistry
259(43)
Molecular Chirality: Enantiomers
259(1)
The Stereogenic Center
260(4)
Symmetry in Achiral Structures
264(1)
Properties of Chiral Molecules: Optical Activity
265(2)
Absolute and Relative Configuration
267(1)
The Cahn--Ingold--Prelog R--S Notational System
268(3)
Fischer Projections
271(1)
Physical Properties of Enantiomers
272(2)
Chiral Drugs
273(1)
Reactions That Create a Stereogenic Center
274(2)
Chiral Molecules with Two Stereogenic Centers
276(3)
Achiral Molecules with Two Stereogenic Centers
279(3)
Chirality of Disubsituted Cyclohexanes
281(1)
Molecules with Multiple Stereogenic Centers
282(2)
Reactions That Produce Diastereomers
284(2)
Resolution of Enantiomers
286(2)
Stereoregular Polymers
288(2)
Stereogenic Centers Other Than Carbon
290(1)
Summary
290(12)
Problems
293(9)
Nucleophilic Substitution
302(37)
Functional Group Transformation by Nucleophilic Substitution
302(3)
Relative Reactivity of Halide Leaving Groups
305(1)
The SN2 Mechanism of Nucleophilic Substitution
306(1)
Stereochemistry of SN2 Reactions
307(1)
How SN2 Reactions Occur
308(2)
Steric Effects in SN2 Reactions
310(2)
Nucleophiles and Nucleophilicity
312(3)
An Enzyme-Catalyzed Nucleophilic Substitution of an Alkyl Halide
314(1)
The SN1 Mechanism of Nucleophilic Substitution
315(1)
Carbocation Stability and SN1 Reaction Rates
315(3)
Stereochemistry of SN1 Reactions
318(1)
Carbocation Rearrangements in SN1 Reactions
319(1)
Effect of Solvent on the Rate of Nucleophilic Substitution
320(3)
Substitution and Elimination as Competing Reactions
323(3)
Sulfonate Esters as Substrates in Nucleophilic Substitution
326(3)
Looking Back: Reactions of Alcohols with Hydrogen Halides
329(1)
Summary
330(9)
Problems
332(7)
Alkynes
339(26)
Sources of Alkynes
339(1)
Nomenclature
340(1)
Physical Properties of Alkynes
341(1)
Structure and Bonding in Alkynes: sp Hybridization
341(3)
Natural and ``Designed'' Enediyne Antibiotics
344(1)
Acidity of Acetylene and Terminal Alkynes
344(2)
Preparation of Alkynes by Alkylation of Acetylene and Terminal Alkynes
346(2)
Preparation of Alkynes by Elimination Reactions
348(2)
Reactions of Alkynes
350(1)
Hydrogenation of Alkynes
350(1)
Metal--Ammonia Reduction of Alkynes
351(1)
Addition of Hydrogen Halides to Alkynes
352(3)
Hydration of Alkynes
355(1)
Addition of Halogens to Alkynes
356(1)
Ozonolysis of Alkynes
357(1)
Summary
357(8)
Problems
358(7)
Conjugation in Alkadienes and Allylic Systems
365(33)
The Allyl Group
365(1)
Allylic Carbocations
366(4)
Allylic Free Radicals
370(1)
Allylic Halogenation
370(2)
Classes of Dienes
372(2)
Relative Stabilities of Dienes
374(1)
Bonding in Conjugated Dienes
375(2)
Bonding in Allenes
377(1)
Preparation of Dienes
378(1)
Addition of Hydrogen Halides to Conjugated Dienes
379(3)
Halogen Addition to Dienes
382(1)
The Diels--Alder Reaction
382(4)
Diene Polymers
383(3)
The π Molecular Orbitals of Ethylene and 1,3-Butadiene
386(2)
A π Molecular Orbital Analysis of the Diels-Alder Reaction
388(2)
Summary
390(8)
Problems
393(5)
Arenes and Aromaticity
398(45)
Benzene
399(1)
Kekule and the Structure of Benzene
399(3)
Benzene, Dreams, and Creative Thinking
401(1)
A Resonance Picture of Bonding in Benzene
402(1)
The Stability of Benzene
403(2)
An Orbital Hybridization View of Bonding in Benzene
405(1)
The π Molecular Orbitals of Benzene
405(1)
Substituted Derivatives of Benzene and Their Nomenclature
406(2)
Polycyclic Aromatic Hydrocarbons
408(3)
Carbon Clusters, Fullerenes, and Nanotubes
410(1)
Physical Properties of Arenes
411(1)
Reactions of Arenes: A Preview
411(1)
The Birch Reduction
412(2)
Free-Radical Halogenation of Alkylbenzenes
414(2)
Oxidation of Alkylbenzenes
416(1)
Nucleophilic Substitution in Benzylic Halides
417(2)
Preparation of Alkenylbenzens
419(1)
Addition Reactions of Alkenylbenzenes
419(2)
Polymerization of Styrene
421(1)
Cyclobutadiene and Cyclooctatetraene
422(1)
Huckel's Rule: Annulenes
423(3)
Aromatic Ions
426(4)
Heterocyclic Aromatic Compounds
430(2)
Heterocyclic Aromatic Compounds and Huckel's Rule
432(1)
Summary
433(10)
Problems
437(6)
Reactions of Arenes: Electrophilic Aromatic Substitution
443(44)
Representative Electrophilic Aromatic Substitution Reactions of Benzene
444(1)
Mechanistic Principles of Electrophilic Aromatic Substitution
444(3)
Nitration of Benzene
447(1)
Sulfonation of Benzene
448(1)
Halogenation of Benzene
448(2)
Friedel--Crafts Alkylation of Benzene
450(3)
Friedel--Crafts Acylation of Benzene
453(2)
Synthesis of Alkylbenzenes by Acylation-Reduction
455(2)
Rate and Regioselectivity in Electrophilic Aromatic Substitution
457(1)
Rate and Regioselectivity in the Nitration of Toluene
458(3)
Rate and Regioselectivity in the Nitration of (Trfluorometyl) benzene
461(2)
Substituent Effects in Electrophilic Aromatic Substitution: Activating Substituents
463(3)
Substituent Effects in Electrophilic Aromatic Substitution: Strongly Deactivating Substitutents
466(3)
Substituent Effects in Electrophilic Aromatic Substitution: Halogens
469(1)
Multiple Substituent Effects
470(2)
Regioselective Synthesis of Disubstituted Aromatic Compounds
472(2)
Substitution in Naphthalene
474(1)
Substitution in Heterocyclic Aromatic Compounds
475(2)
Summary
477(10)
Problems
480(7)
Spectroscopy
487(59)
Principles of Molecular Spectroscopy: Electromagnetic Radiation
488(1)
Principles of Molecular Spectroscopy: Quantized Energy States
489(1)
Introduction to 1H NMR Spectroscopy
490(3)
Nuclear Shielding and 1H Chemical Shifts
493(1)
Effects of Molecular Structure on 1H Chemical Shifts
494(3)
Interpreting Proton NMR Spectra
497(3)
Spin--Spin Splitting in NMR Spectroscopy
500(3)
Splitting Patterns: The Ethyl Group
503(2)
Splitting Patterns: The Isopropyl Group
505(1)
Splitting Patterns: Pairs of Doublets
505(2)
Complex Splitting Patterns
507(2)
1H NMR Spectra of Alcohols
509(1)
NMR and Conformations
510(1)
13C NMR Spectroscopy
510(2)
13C Chemical Shifts
512(1)
13C NMR and Peak Intensities
513(2)
13C---1H Coupling
515(1)
Using DEPT to Count the Hydrogens Attached to 13C
515(3)
Magnetic Resonance Imaging
517(1)
Infrared Spectroscopy
518(4)
Ultraviolet-Visible (UV-VIS) Spectroscopy
522(4)
Mass Spectrometry
526(6)
Gas Chromatography, GC/MS, and MS/MS
530(2)
Molecular Formula as a Clue to Structure
532(1)
Summary
533(13)
Problems
536(10)
Organometallic Compounds
546(33)
Organometallic Nomenclature
547(1)
Carbon--Metal Bonds in Organometallic Compounds
547(2)
Preparation of Organolithium Compounds
549(1)
Preparation of Organomagnesium Compounds: Grignard Reagents
550(1)
Organolithium and Organomagnesium Compounds as Brnsted Bases
551(2)
Synthesis of Alcohols Using Grignard Reagents
553(1)
Synthesis of Alcohols Using Organolithium Reagents
554(2)
Synthesis of Acetylenic Alcohols
556(1)
Retrosynthetic Analysis
557(3)
Preparation of Tertiary Alcohols from Esters and Grignard Reagents
560(1)
Alkane Synthesis Using Organocopper Reagents
561(2)
An Organozinc Reagent for Cyclopropane Synthesis
563(2)
Carbenes and Carbenoids
565(1)
Transition-Metal Organometallic Compounds
566(1)
Ziegler--Natta Catalysis of Alkene Polymerization
567(3)
An Organometallic Compound That Occurs Naturally: Coenzyme B12
568(2)
Summary
570(9)
Problems
573(6)
Alcohols, Diols, and Thiols
579(40)
Sources of Alcohols
579(4)
Preparation of Alcohols by Reduction of Aldehydes and Ketones
583(4)
Preparation of Alcohols by Reduction of Carboxylic Acids and Esters
587(1)
Preparation of Alcohols from Expoxides
587(2)
Preparation of Diols
589(1)
Reactions of Alcohols: A Review and a Preview
590(1)
Conversion of Alcohols to Ethers
590(3)
Esterification
593(2)
Esters of Inorganic Acids
595(1)
Oxidation of Alcohols
596(4)
Economic and Environmental Factors in Organic Synthesis
598(2)
Biological Oxidation of Alcohols
600(2)
Oxidative Cleavage of Vicinal Diols
602(1)
Preparation of Thiols
603(1)
Properties of Thiols
604(1)
Spectroscopic Analysis of Alcohols
605(2)
Summary
607(12)
Problems
611(8)
Ethers, Epoxides, and Sulfides
619(35)
Nomenclature of Ethers, Epoxides, and Sulfides
619(2)
Structure and Bonding in Ethers and Epoxides
621(1)
Physical Properties of Ethers
622(1)
Crown Ethers
622(3)
Polyether Antibiotics
624(1)
Preparation of Ethers
625(1)
The Williamson Ether Synthesis
626(1)
Reactions of Ethers: A Review and a Preview
627(1)
Acid-Catalyzed Cleavage of Ethers
628(2)
Preparation of Epoxides: A Review and a Preview
630(1)
Conversion of Vicinal Halohydrins to Epoxides
630(2)
Reactions of Epoxides: A Review and a Preview
632(1)
Nucleophilic Ring-Opening Reactions of Epoxides
633(2)
Acid-Catalyzed Ring-Opening Reactions of Epoxides
635(2)
Epoxides in Biological Processes
637(1)
Preparation of Sulfides
638(1)
Oxidation of Sulfides: Sulfoxides and Sulfones
639(1)
Alkylation of Sulfides: Sulfonium Salts
640(1)
Spectroscopic Analysis of Ethers
641(2)
Summary
643(11)
Problems
647(7)
Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group
654(47)
Nomenclature
654(3)
Structure and Bonding: The Carbonyl Group
657(1)
Physical Properties
658(1)
Sources of Aldehydes and Ketones
659(2)
Reactions of Aldehydes and Ketones: A Review and a Preview
661(2)
Principles of Nucleophilic Addition: Hydration of Aldehydes and Ketones
663(4)
Cyanohydrin Formation
667(1)
Acetal Formation
668(3)
Acetals as Protecting Groups
671(1)
Reaction with Primary Amines: Imines
672(2)
Reaction with Secondary Amines: Enamies
674(3)
Imines in Biological Chemistry
675(2)
The Writtig Reaction
677(1)
Planning an Alkene Synthesis via the Wittig Reaction
678(3)
Stereoselective Addition to Carbonyl Groups
681(1)
Oxidation of Aldehydes
682(1)
Baeyer--Villiger Oxidation of Ketones
683(1)
Spectroscopic Analysis of Aldehydes and Ketones
684(4)
Summary
688(13)
Problems
691(10)
Enols and Enolates
701(35)
The α-Carbon Atom and Its Hydrogens
702(1)
&alpha: Halogenation of Aldehydes and Ketones
703(1)
Mechanism of α Halogenation of Aldehydes and Ketones
703(2)
Enolization and Enol Content
705(2)
Stabilized Enols
707(1)
Base-Catalyzed Enolization: Enolate Anions
708(3)
The Haloform Reaction
711(2)
The Haloform Reaction and the Biosynthesis of Trihalomethanes
713(1)
Some Chemical and Stereochemical Consequences of Enolization
713(2)
The Aldol Condensation
715(4)
Mixed Aldol Condensations
719(1)
Effects of Conjugation in α, β-Unsaturated Aldehydes and Ketones
720(2)
Conjugate Addition to α, β-Unsaturated Carbonyl Compounds
722(2)
Additions of Carbanions to α, β-Unsaturated Ketones: The Michael Reaction
724(1)
Conjugate Addition of Organocopper Reagents to α, β-Unsaturated Carbonyl Compounds
724(1)
Alkylation of Enolate Anions
725(1)
Summary
726(10)
Problems
726(10)
Carboxylic Acids
736(38)
Carboxylic Acid Nomenclature
737(1)
Structure and Bonding
738(1)
Physical Properties
739(1)
Acidity of Carboxylic Acids
740(2)
Salts of Carboxylic Acids
742(3)
Quantitative Relationships Involving Carboxylic Acids
743(2)
Substituents and Acid Strength
745(2)
Ionization of Substituted Benzoic Acids
747(1)
Dicarboxylic Acids
748(1)
Carbonic Acid
749(1)
Sources of Carboxylic Acids
750(1)
Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents
750(2)
Synthesis of Carboxylic Acids by the Preparation and Hydrolysis of Nitriles
752(1)
Reactions of Carboxylic Acids: A Review and a Preview
753(1)
Mechanism of Acid-Catalyzed Esterification
754(4)
Intramolecular Ester Formation: Lactones
758(1)
α Halogenation of Carboxylic Acids: The Hell-Volhard-Zelinsky Reaction
759(1)
Decarboxylation of Malonic Acid and Related Compounds
760(3)
Spectroscopic Analysis of Carboxylic Acids
763(2)
Summary
765(9)
Problems
768(6)
Carboxylic Acid Derivatives: Nucleophilic ACYL Substitution
774(57)
Nomenclature of Carboxylic Acid Derivatives
775(2)
Structure of Carboxylic Acid Derivatives
777(3)
Nucleophilic Substitution in Acyl Chlorides
780(3)
Preparation of Carboxylic Acid Anhydrides
783(1)
Reactions of Carboxylic Acid Anhydrides
784(3)
Sources of Esters
787(1)
Physical Properties of Esters
788(2)
Reactions of Esters: A Review and a Preview
790(1)
Acid-Catalyzed Ester Hydrolysis
791(3)
Ester Hydrolysis in Base: Saponification
794(5)
Reaction of Esters with Ammonia and Amines
799(1)
Thioesters
800(1)
Preparation of Amides
800(3)
Lactams
803(1)
Imides
804(1)
Hydrolysis of Amides
804(3)
The Hofmann Rearrangement
807(6)
Condensation Polymers: Polyamides and Polyesters
809(4)
Preparation of Nitriles
813(2)
Hydrolysis of Nitriles
815(1)
Addition of Grignard Reagents to Nitriles
816(1)
Spectroscopic Analysis of Carboxylic Acid Derivatives
817(2)
Summary
819(12)
Problems
822(9)
Ester Enolates
831(27)
The Claisen Condensation
832(3)
Intramolecular Claisen Condensation: The Dieckmann Reaction
835(1)
Mixed Claisen Condensations
836(1)
Acylation of Ketones with Esters
837(1)
Ketone Synthesis via β-Keto Esters
838(1)
The Acetoacetic Ester Synthesis
839(3)
The Malonic Ester Synthesis
842(3)
Barbiturates
845(1)
Michael Additions of Stabilized Anions
846(1)
α Deprotonation of Carbonyl Compounds by Lithium Dialkylamides
847(3)
Summary
850(8)
Problems
853(5)
Amines
858(59)
Amine Nomenclature
859(2)
Structure and Bonding
861(2)
Physical Properties
863(1)
Measures of Amine Basicity
864(1)
Basicity of Amines
865(6)
Amines as Natural Products
869(2)
Tetraalkylammonium Salts as Phase-Transfer Catalysts
871(1)
Reactions That Lead to Amines: A Review and a Preview
872(1)
Preparation of Amines by Alkylation of Ammonia
872(3)
The Gabriel Synthesis of Primary Alkylamines
875(2)
Preparation of Amines by Reduction
877(2)
Reductive Amination
879(2)
Reactions of Amines: A Review and a Preview
881(2)
Reaction of Amines with Alkyl Halides
883(1)
The Hofmann Elimination
883(3)
Electrophilic Aromatic Substitution in Arylamines
886(2)
Nitrosation of Alkylamines
888(3)
Nitrosation of Arylamines
891(1)
Synthetic Transformations of Aryl Diazonium Salts
892(3)
Azo Coupling
895(2)
From Dyes to Sulfa Drugs
896(1)
Spectroscopic Analysis of Amines
897(3)
Summary
900(17)
Problems
907(10)
Aryl Halides
917(22)
Bonding in Aryl Halides
917(1)
Sources of Aryl Halides
918(1)
Physical Properties of Aryl Halides
918(1)
Reactions of Aryl Halides: A Review and a Preview
919(3)
Nucleophilic Substitution in Nitro-Substituted Aryl Halides
922(1)
The Addition--Elimination Mechanism of Nucleophilic Aromatic Substitution
923(3)
Related Nucleophilic Aromatic Substitution Reactions
926(1)
The Elimination--Addition Mechanism of Nucleophilic Aromatic Substitution: Benzyne
927(4)
Diels--Alder Reactions of Benzyne
931(1)
Summary
932(7)
Problems
934(5)
Phenols
939(33)
Nomenclature
939(1)
Structure and Bonding
940(1)
Physical Properties
941(1)
Acidity of Phenols
942(2)
Substituent Effects on the Acidity of Phenols
944(2)
Sources of Phenols
946(1)
Naturally Occurring Phenols
946(2)
Reactions of Phenols: Electrophilic Aromatic Substitution
948(1)
Acylation of Phenols
949(3)
Carboxylation of Phenols: Aspirin and the Kolbe-Schmitt Reaction
952(2)
Preparation of Aryl Ethers
954(2)
Agent Orange and Dioxin
955(1)
Cleavage of Aryl Ethers by Hydrogen Halides
956(1)
Claisen Rearrangement of Allyl Aryl Ethers
957(1)
Oxidation of Phenols: Quinones
958(2)
Spectroscopic Analysis of Phenols
960(2)
Summary
962(10)
Problems
965(7)
Carbohydrates
972(43)
Classification of Carbohydrates
972(1)
Fischer Projections and the D--L Notation
973(1)
The Aldotetroses
974(2)
Aldopentoses and Aldohexoses
976(2)
A Mnemonic for Carbohydrate Configurations
978(1)
Cyclic Forms of Carbohydrates: Furanose Forms
978(3)
Cyclic Forms of Carbohydrates: Pyranose Forms
981(4)
Mutarotation
985(1)
Ketoses
986(1)
Deoxy Sugars
987(1)
Amino Sugars
988(1)
Branched-Chain Carbohydrates
988(1)
Glycosides
988(3)
Disaccharides
991(2)
Polysaccharides
993(2)
Cell-Surface Glycoproteins
995(1)
Carbohydrate Structure Determination
996(1)
Reduction of Carbohydrates
996(2)
How Sweet It Is!
997(1)
Oxidation of Carbohydrates
998(3)
Cyanohydrin Formation and Carbohydrate Chain Extension
1001(2)
Epimerization, Isomerization, and Retro-Aldol Cleavage Reactions of Carbohydrates
1003(1)
Acylation and Alkylation of Hydroxyl Groups in Carbohydrates
1004(1)
Periodic Acid Oxidation of Carbohydrates
1005(1)
Summary
1006(9)
Problems
1008(7)
Lipids
1015(36)
Acetyl Coenzyme A
1016(1)
Fats, Oils, and Fatty Acids
1017(2)
Fatty Acid Biosynthesis
1019(3)
Phospholipids
1022(2)
Waxes
1024(1)
Prostaglandins
1024(1)
Terpenes: The Isoprene Rule
1025(3)
Isopentenyl Pyrophosphate: The Biological Isoprene Unit
1028(1)
Carbon--Carbon Bond Formation in Terpene Biosynthesis
1029(3)
The Pathway from Acetate to Isopentenyl Pyrophosphate
1032(2)
Steroids: Cholesterol
1034(4)
Good Cholesterol? Bad Cholesterol? What's the Difference?
1038(1)
Vitamin D
1038(1)
Bile Acids
1039(1)
Corticosteroids
1040(1)
Sex Hormones
1040(2)
Anabolic Steroids
1041(1)
Carotenoids
1042(1)
Summary
1042(9)
Problems
1045(6)
Amino Acids, Peptides, and Proteins. Nucleic Acids
1051
Classification of Amino Acids
1052
Stereochemistry of Amino Acids
1052
Acid--Base Behavior of Amino Acids
1057
Electrophoresis
1060
Synthesis of Amino Acids
1061
Reactions of Amino Acids
1063
Some Biochemical Reactions of Amino Acids
1063
Peptides
1067
Introduction to Peptide Structure Determination
1070
Amino Acid Analysis
1070
Partial Hydrolysis of Peptides
1071
End Group Analysis
1071
Insulin
1073
The Edman Degradation and Automated Sequencing of Peptides
1074
The Strategy of Peptide Synthesis
1076
Amino Group Protection
1077
Carboxyl Group Protection
1079
Peptide Bond Formation
1079
Solid-Phase Peptide Synthesis: The Merrifield Method
1082
Secondary Structures of Peptides and Proteins
1084
Tertiary Structure of Peptides and Proteins
1086
Coenzymes
1088
Protein Quaternary Structure: Hemoglobin
1089
Pyrimidines and Purines
1090
Nucleosides
1091
Nucleotides
1092
Nucleic Acids
1093
Structure and Replication of DNA: The Double Helix
1094
DNA-Directed Protein Biosynthesis
1096
AIDS
1098
DNA Sequencing
1100
Summary
1103
Problems
1106
Appendix 1 Physical PropertiesA-1
Appendix 2 Answers to In-Text ProblemsA-9
Appendix 3 Learning Chemistry with Molecular Models: Using SpartanBuild and SpartanViewA-64
GlossaryG-1
CreditsC-1
IndexI-1

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