CART

(0) items

Organic Chemistry,9780131478718
This item qualifies for
FREE SHIPPING!

FREE SHIPPING OVER $59!

Your order must be $59 or more, you must select US Postal Service Shipping as your shipping preference, and the "Group my items into as few shipments as possible" option when you place your order.

Bulk sales, PO's, Marketplace Items, eBooks, Apparel, and DVDs not included.

Organic Chemistry

by
Edition:
6th
ISBN13:

9780131478718

ISBN10:
0131478710
Format:
Hardcover
Pub. Date:
1/1/2006
Publisher(s):
Prentice Hall
Includes 2-weeks free access to
step-by-step solutions for this book.
Step-by-Step solutions are actual worked out problems to the questions at the end of each chapter that help you understand your homework and study for your exams. Chegg and eCampus are providing you two weeks absolutely free. 81% of students said using Step-by-Step solutions prepared them for their exams.
List Price: $190.50
More New and Used
from Private Sellers
Starting at $9.16
See Prices

Rent Textbook

We're Sorry
Sold Out

Used Textbook

We're Sorry
Sold Out

eTextbook

We're Sorry
Not Available

New Textbook

We're Sorry
Sold Out

Related Products


  • Ace Student Access Kit for Organic Chemistry
    Ace Student Access Kit for Organic Chemistry
  • Organic Chemistry
    Organic Chemistry
  • Organic Chemistry
    Organic Chemistry
  • Organic Chemistry and CW+ GradeTracker Access Card Package
    Organic Chemistry and CW+ GradeTracker Access Card Package
  • Organic Chemistry Plus MasteringChemistry with eText -- Access Card Package
    Organic Chemistry Plus MasteringChemistry with eText -- Access Card Package
  • Solutions Manual for Organic Chemistry
    Solutions Manual for Organic Chemistry
  • Student Solutions Manual for Organic Chemistry
    Student Solutions Manual for Organic Chemistry




Summary

In a highly accessible fashion, this top-selling book bridges the gap between conceptual understanding and actual applicationwhile strongly emphasizing the development of problem-solving skills. The book focuses on traditional organic chemistry topics and offers up-to-date aspects of spectroscopy, relevant photographs, and many applications to polymer chemistry integrated throughout the book.

Table of Contents

Preface xxiii
About the Author xli
1 Introduction and Review 1(38)
1-1 The Origins of Organic Chemistry
1(2)
1-2 Principles of Atomic Structure
3(3)
1-3 Bond Formation: The Octet Rule
6(1)
1-4 Lewis Structures
7(1)
1-5 Multiple Bonding
8(1)
Summary: Common Bonding Patterns (Uncharged)
9(1)
1-6 Electronegativity and Bond Polarity
9(2)
1-7 Formal Charges
11(1)
1-8 Ionic Structures
12(1)
Summary: Common Bonding Patterns in Organic Compounds and Ions
13(1)
1-9 Resonance
13(4)
1-10 Structural Formulas
17(3)
1-11 Molecular Formulas and Empirical Formulas
20(1)
1-12 Arrhenius Acids and Bases
21(1)
1-13 Bransted-Lowry Acids and Bases
22(7)
1-14 Lewis Acids and Bases
29(3)
Chapter 1 Glossary
32(2)
Study Problems
34(5)
2 Structure and Properties of Organic Molecules 39(42)
2-1 Wave Properties of Electrons in Orbitals
39(2)
2-2 Molecular Orbitals
41(3)
2-3 Pi Bonding
44(1)
2-4 Hybridization and Molecular Shapes
45(4)
2-5 Drawing Three-Dimensional Molecules
49(1)
2-6 General Rules of Hybridization and Geometry
50(4)
2-7 Bond Rotation
54(2)
2-8 Isomerism
56(2)
2-9 Polarity of Bonds and Molecules
58(3)
2-10 Intermolecular Forces
61(4)
2-11 Polarity Effects on Solubilities
65(3)
2-12 Hydrocarbons
68(3)
2-13 Organic Compounds Containing Oxygen
71(2)
2-14 Organic Compounds Containing Nitrogen
73(2)
Chapter 2 Glossary
75(2)
Study Problems
77(4)
3 Structure and Stereochemistry of Alkanes 81(44)
3-1 Classification of Hydrocarbons (Review)
81(1)
3-2 Molecular Formulas of Alkanes
82(1)
3-3 Nomenclature of Alkanes
83(6)
Summary: Rules for Naming Alkanes
88(1)
3-4 Physical Properties of Alkanes
89(2)
3-5 Uses and Sources of Alkanes
91(2)
3-6 Reactions of Alkanes
93(1)
3-7 Structure and Conformations of Alkanes
94(4)
3-8 Conformations of Butane
98(2)
3-9 Conformations of Higher Alkanes
100(1)
3-10 Cycloalkanes
100(3)
3-11 cis-trans Isomerism in Cycloalkanes
103(1)
3-12 Stabilities of Cycloalkanes; Ring Strain
103(4)
3-13 Cyclohexane Conformations
107(4)
3-14 Conformations of Monosubstituted Cyclohexanes
111(3)
3-15 Conformations of Disubstituted Cyclohexanes
114(3)
3-16 Bicyclic Molecules
117(2)
Chapter 3 Glossary
119(3)
Study Problems
122(3)
4 The Study of Chemical Reactions 125(42)
4-1 Introduction
125(1)
4-2 Chlorination of Methane
125(1)
4-3 The Free-Radical Chain Reaction
126(4)
Key Mechanism: Free-Radical Halogenation
128(2)
4-4 Equilibrium Constants and Free Energy
130(3)
4-5 Enthalpy and Entropy
133(1)
4-6 Bond-Dissociation Enthalpies
134(1)
4-7 Enthalpy Changes in Chlorination
135(2)
4-8 Kinetics and the Rate Equation
137(2)
4-9 Activation Energy and the Temperature Dependence of Rates
139(1)
4-10 Transition States
140(2)
4-11 Rates of Multistep Reactions
142(1)
4-12 Temperature Dependence of Halogenation
143(1)
4-13 Selectivity in Halogenation
144(5)
4-14 The Hammond Postulate
149(4)
4-15 Radical Inhibitors
153(2)
4-16 Reactive Intermediates
155(5)
Summary: Reactive Intermediates
160(1)
Chapter 4 Glossary
160(3)
Study Problems
163(4)
5 Stereochemistry 167(45)
5-1 Introduction
167(1)
5-2 Chirality
168(6)
5-3 (R) and (S) Nomenclature of Asymmetric Carbon Atoms
174(5)
5-4 Optical Activity
179(5)
5-5 Biological Discrimination of Enantiomers
184(1)
5-6 Racemic Mixtures
185(1)
5-7 Enantiomeric Excess and Optical Purity
186(1)
5-8 Chirality of Conformationally Mobile Systems
187(2)
5-9 Chiral Compounds without Asymmetric Atoms
189(2)
5-10 Fischer Projections
191(5)
Summary: Fischer Projections and Their Use
196(1)
5-11 Diastereomers
196(2)
Summary: Types of Isomers
197(1)
5-12 Stereochemistry of Molecules with Two or More Asymmetric Carbons
198(1)
5-13 Meso Compounds
199(2)
5-14 Absolute and Relative Configuration
201(2)
5-15 Physical Properties of Diastereomers
203(1)
5-16 Resolution of Enantiomers
204(3)
Chapter 5 Glossary
207(2)
Study Problems
209(3)
6 Alkyl Halides: Nucleophilic Substitution and Elimination 212(67)
6-1 Introduction
212(1)
6-2 Nomenclature of Alkyl Halides
213(2)
6-3 Common Uses of Alkyl Halides
215(2)
6-4 Structure of Alkyl Halides
217(1)
6-5 Physical Properties of Alkyl Halides
218(2)
6-6 Preparation of Alkyl Halides
220(5)
Summary: Methods for Preparing Alkyl Halides
223(2)
6-7 Reactions of Alkyl Halides: Substitution and Elimination
225(1)
6-8 Second-Order Nucleophilic Substitution: The SN2 Reaction
226(2)
Key Mechanism: The SN2 Reaction
227(1)
6-9 Generality of the SN2 Reaction
228(2)
Summary: SN2 Reactions of Alkyl Halides
228(2)
6-10 Factors Affecting SN2 Reactions: Strength of the Nucleophile
230(4)
Summary: Trends in Nucleophilicity
231(3)
6-11 Reactivity of the Substrate in SN2 Reactions
234(4)
6-12 Stereochemistry of the SN2 Reaction
238(2)
6-13 First-Order Nucleophilic Substitution: The SN1 Reaction
240(4)
Key Mechanism: The 5N1 Reaction
241(3)
6-14 Stereochemistry of the SN1 Reaction
244(2)
6-15 Rearrangements in SN I Reactions
246(3)
6-16 Comparison of SN1 and SN2 Reactions
249(3)
Summary: Nucleophilic Substitutions
251(1)
6-17 First-Order Elimination: The El Reaction
252(5)
Key Mechanism: The El Reaction
252(4)
Summary: Carbocation Reactions
256(1)
6-18 Positional Orientation of Elimination: Zaitsev's Rule
257(1)
6-19 Second-Order Elimination: The E2 Reaction
258(3)
Key Mechanism: The E2 Reaction
259(2)
6-20 Stereochemistry of the E2 Reaction
261(1)
6-21 Comparison of El and E2 Elimination Mechanisms
262(8)
Summary: Elimination Reactions
264(3)
Summary: Reactions of Alkyl Halides
267(3)
Chapter 6 Glossary
270(3)
Study Problems
273(6)
7 Structure and Synthesis of Alkenes 279(42)
7-1 Introduction
279(1)
7-2 The Orbital Description of the Alkene Double Bond
280(1)
7-3 Elements of Unsaturation
281(2)
7-4 Nomenclature of Alkenes
283(2)
7-5 Nomenclature of Cis-Trans Isomers
285(3)
Summary: Rules for Naming Alkenes
287(1)
7-6 Commercial Importance of Alkenes
288(2)
7-7 Stability of Alkenes
290(6)
7-8 Physical Properties of Alkenes
296(2)
7-9 Alkene Synthesis by Elimination of Alkyl Halides
298(8)
7-10 Alkene Synthesis by Dehydration of Alcohols
306(3)
Key Mechanism: Acid-Catalyzed Dehydration of an Alcohol
307(2)
7-11 Alkene Synthesis by High-Temperature Industrial Methods
309(7)
Summary: Methods for Synthesis of Alkenes
314(2)
Chapter 7 Glossary
316(2)
Study Problems
318(3)
8 Reactions of Alkenes 321(61)
8-1 Reactivity of the Carbon-Carbon Double Bond
321(1)
8-2 Electrophilic Addition to Alkenes
322(2)
Key Mechanism: Electrophilic Addition to Alkenes
322(2)
8-3 Addition of Hydrogen Halides to Alkenes
324(6)
8-4 Addition of Water: Hydration of Alkenes
330(3)
8-5 Hydration by Oxymercuration-Demercuration
333(2)
8-6 Alkoxymercuration-Demercuration
335(1)
8-7 Hydroboration of Alkenes
336(6)
8-8 Addition of Halogens to Alkenes
342(3)
8-9 Formation of Halohydrins
345(3)
8-10 Catalytic Hydrogenation of Alkenes
348(2)
8-11 Addition of Carbenes to Alkenes
350(3)
8-12 Epoxidation of Alkenes
353(2)
8-13 Acid-Catalyzed Opening of Epoxides
355(3)
8-14 Syn Hydroxylation of Alkenes
358(2)
8-15 Oxidative Cleavage of Alkenes
360(3)
8-16 Polymerization of Alkenes
363(11)
Summary: Reactions of Alkenes
370(4)
Chapter 8 Glossary
374(2)
Study Problems
376(6)
9 Alkynes 382(35)
9-1 Introduction
382(1)
9-2 Nomenclature of Alkynes
383(1)
9-3 Physical Properties of Alkynes
384(1)
9-4 Commercial Importance of Alkynes
384(2)
9-5 Electronic Structure of Alkynes
386(1)
9-6 Acidity of Alkynes; Formation of Acetylide Ions
387(2)
9-7 Synthesis of Alkynes from Acetylides
389(4)
9-8 Synthesis of Alkynes by Elimination Reactions
393(3)
Summary: Syntheses of Alkynes
396(1)
9-9 Addition Reactions of Alkynes
396(10)
9-10 Oxidation of Alkynes
406(6)
Summary: Reactions of Alkynes
409(3)
Chapter 9 Glossary
412(1)
Study Problems
413(4)
10 Structure and Synthesis of Alcohols 417(43)
10-1 Introduction
417(1)
10-2 Structure and Classification of Alcohols
417(2)
10-3 Nomenclature of Alcohols and Phenols
419(4)
10-4 Physical Properties of Alcohols
423(2)
10-5 Commercially Important Alcohols
425(2)
10-6 Acidity of Alcohols and Phenols
427(3)
10-7 Synthesis of Alcohols: Introduction and Review
430(2)
Summary: Previous Alcohol Syntheses
430(2)
10-8 Organometallic Reagents for Alcohol Synthesis
432(3)
10-9 Addition of Organometallic Reagents to Carbonyl Compounds
435(8)
Key Mechanism: Grignard Reactions
435(7)
Summary: Grignard Reactions
442(1)
10-10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides
443(2)
10-11 Reduction of the Carbonyl Group: Synthesis of 1 and 2 Alcohols
445(6)
Summary: Reactions of LiAlH4 and NaBH4
448(1)
Summary: Alcohol Syntheses
449(2)
10-12 Thiols (Mercaptans)
451(3)
Chapter 10 Glossary
454(1)
Study Problems
455(5)
11 Reactions of Alcohols 460(48)
11-1 Oxidation States of Alcohols and Related Functional Groups
460(2)
11-2 Oxidation of Alcohols
462(3)
11-3 Additional Methods for Oxidizing Alcohols
465(2)
11-4 Biological Oxidation of Alcohols
467(2)
11-5 Alcohols as Nucleophiles and Electrophiles; Formation of Tosylates
469(3)
Summary: SN2 Reactions of Tosylate Esters
471(1)
11-6 Reduction of Alcohols
472(1)
11-7 Reactions of Alcohols with Hydrohalic Acids
472(5)
11-8 Reactions of Alcohols with Phosphorus Halides
477(1)
11-9 Reactions of Alcohols with Thionyl Chloride
478(2)
11-10 Dehydration Reactions of Alcohols
480(8)
11-11 Unique Reactions of Diols
488(2)
11-12 Esterification of Alcohols
490(1)
11-13 Esters of Inorganic Acids
491(3)
11-14 Reactions of Alkoxides
494(8)
Key Mechanism: The Williamson Ether Synthesis
494(5)
Summary: Reactions of Alcohols
499(3)
Chapter 11 Glossary
502(1)
Study Problems
503(5)
12 Infrared Spectroscopy and Mass Spectrometry 508(51)
12-1 Introduction
508(1)
12-2 The Electromagnetic Spectrum
509(1)
12-3 The Infrared Region
510
12-4 Molecular Vibrations 51
1(512)
12-5 1R-Active and IR-Inactive Vibrations
513(1)
12-6 Measurement of the IR Spectrum
514(3)
12-7 Infrared Spectroscopy of Hydrocarbons
517(5)
12-8 Characteristic Absorptions of Alcohols and Amines
522(1)
12-9 Characteristic Absorptions of Carbonyl Compounds
523(6)
12-10 Characteristic Absorptions of C-N Bonds
529(1)
12-11 Simplified Summary of IR Stretching Frequencies
530(2)
12-12 Reading and Interpreting IR Spectra (Solved Problems)
532(5)
12-13 Introduction to Mass Spectrometry
537(4)
12-14 Determination of the Molecular Formula by Mass Spectrometry
541(3)
12-15 Fragmentation Patterns in Mass Spectrometry
544(7)
Summary: Common Fragmentation Patterns
549(2)
Chapter 12 Glossary
551(1)
Study Problems
552(7)
13 Nuclear Magnetic Resonance Spectroscopy 559(64)
13-1 Introduction
559(1)
13-2 Theory of Nuclear Magnetic Resonance
559(3)
13-3 Magnetic Shielding by Electrons
562(2)
13-4 The NMR Spectrometer
564(1)
13-5 The Chemical Shift
565(7)
13-6 The Number of Signals
572(1)
13-7 Areas of the Peaks
573(3)
13-8 Spin-Spin Splitting
576(9)
13-9 Complex Splitting
585(3)
13-10 Stereochemical Nonequivalence of Protons
588(3)
13-11 Time Dependence of NMR Spectroscopy
591(8)
Problem-Solving Strategy: Interpreting Proton NMR Spectra
594(5)
13-12 Carbon-13 NMR Spectroscopy
599(8)
13-13 Interpreting Carbon NMR Spectra
607(2)
13-14 Nuclear Magnetic Resonance Imaging
609(5)
Problem-Solving Strategy: Spectroscopy Problems
610(4)
Chapter 13 Glossary
614(2)
Study Problems
616(7)
14 Ethers, Epoxides, and Sulfides 623(40)
14-1 Introduction
623(1)
14-2 Physical Properties of Ethers
623(5)
14-3 Nomenclature of Ethers
628(3)
14-4 Spectroscopy of Ethers
631(2)
14-5 The Williamson Ether Synthesis
633(1)
14-6 Synthesis of Ethers by Alkoxymercuration-Demercuration
634(1)
14-7 Industrial Synthesis: Bimolecular Dehydration of Alcohols
635(1)
Summary: Syntheses of Ethers
636(1)
14-8 Cleavage of Ethers by HBr and HI
636(3)
14-9 Autoxidation of Ethers
639(1)
Summary: Reactions of Ethers
639(1)
14-10 Sulfides (Thioethers)
640(2)
14-11 Synthesis of Epoxides
642(3)
Summary: Epoxide Syntheses
645(1)
14-12 Acid-Catalyzed Ring Opening of Epoxides
645(4)
14-13 Base-Catalyzed Ring Opening of Epoxides
649(1)
14-14 Orientation of Epoxide Ring Opening
650(2)
14-15 Reactions of Epoxides with Grignard and Organolithium Reagents
652(1)
14-16 Epoxy Resins: The Advent of Modern Glues
653(3)
Summary: Reactions of Epoxides
655(1)
Chapter 14 Glossary
656(2)
Study Problems
658(5)
15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy 663(42)
15-1 Introduction
663(1)
15-2 Stabilities of Dienes
663(2)
15-3 Molecular Orbital Picture of a Conjugated System
665(4)
15-4 Allylic Cations
669(1)
15-5 1,2- and 1,4-Addition to Conjugated Dienes
670(2)
15-6 Kinetic versus Thermodynamic Control in the Addition of HBr to 1,3-Butadiene
672(2)
15-7 Allylic Radicals
674(2)
15-8 Molecular Orbitals of the Allylic System
676(2)
15-9 Electronic Configurations of the Ally! Radical, Cation, and Anion
678(1)
15-10 SN2 Displacement Reactions of Allylic Halides and Tosylates
679(1)
15-11 The Diels-Alder Reaction
680(9)
Key Mechanism: The Diels-Alder Reaction
680(9)
15-12 The Diels-Alder as an Example of a Pericyclic Reaction
689(3)
15-13 Ultraviolet Absorption Spectroscopy
692(7)
Chapter 15 Glossary
699(2)
Study Problems
701(4)
16 Aromatic Compounds 705(44)
16-1 Introduction: The Discovery of Benzene
705(1)
16-2 The Structure and Properties of Benzene
705(4)
16-3 The Molecular Orbitals of Benzene
709(3)
16-4 The Molecular Orbital Picture of Cyclobutadiene
712(2)
16-5 Aromatic, Antiaromatic, and Nonaromatic Compounds
714(1)
16-6 Hackers Rule
714(2)
16-7 Molecular Orbital Derivation of Hiickel's Rule
716(1)
16-8 Aromatic Ions
717(6)
16-9 Heterocyclic Aromatic Compounds
723(4)
16-10 Polynuclear Aromatic Hydrocarbons
727(2)
16-11 Aromatic Allotropes of Carbon
729(2)
16-12 Fused Heterocyclic Compounds
731(1)
16-13 Nomenclature of Benzene Derivatives
732(2)
16-14 Physical Properties of Benzene and Its Derivatives
734(1)
16-15 Spectroscopy of Aromatic Compounds
735(3)
Chapter 16 Glossary
738(2)
Study Problems
740(9)
17 Reactions of Aromatic Compounds 749(56)
17-1 Electrophilic Aromatic Substitution
749(2)
Key Mechanism: Electrophilic Aromatic Substitution
750(1)
17-2 Halogenation of Benzene
751(2)
17-3 Nitration of Benzene
753(2)
17-4 Sulfonation of Benzene
755(2)
17-5 Nitration of Toluene: The Effect of Alkyl Substitution
757(2)
17-6 Activating, Ortho, Para-Directing Substituents
759(4)
Summary: Activating, Ortho, Para-Directors
762(1)
17-7 Deactivating, Meta-Directing Substituents
763(3)
Summary: Deactivating, Meta-Directors
766(1)
17-8 Halogen Substituents: Deactivating, but Ortho, Para-Directing
766(2)
Summary: Directing Effects of Substituents
768(1)
17-9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution
768(3)
17-10 The Friedel-Crafts Alkylation
771(4)
17-11 The Friedel-Crafts Acylation
775(5)
Summary: Comparison of Friedel-Crafts Alkylation and Acylation
778(2)
17-12 Nucleophilic Aromatic Substitution
780(5)
17-13 Addition Reactions of Benzene Derivatives
785(2)
17-14 Side-Chain Reactions of Benzene Derivatives
787(4)
17-15 Reactions of Phenols
791(6)
Summary: Reactions of Aromatic Compounds
794(3)
Chapter 17 Glossary
797(3)
Study Problems
800(5)
18 Ketones and Aldehydes 805(65)
18-1 Carbonyl Compounds
805(1)
18-2 Structure of the Carbonyl Group
806(1)
18-3 Nomenclature of Ketones and Aldehydes
806(3)
18-4 Physical Properties of Ketones and Aldehydes
809(2)
18-5 Spectroscopy of Ketones and Aldehydes
811(7)
18-6 Industrial Importance of Ketones and Aldehydes
818(1)
18-7 Review of Syntheses of Ketones and Aldehydes
818(4)
18-8 Synthesis of Ketones and Aldehydes Using 1,3-Dithianes
822(1)
18-9 Synthesis of Ketones from Carboxylic Acids
823(1)
18-10 Synthesis of Ketones from Nitriles
824(1)
18-11 Synthesis of Aldehydes and Ketones from Acid Chlorides
825(4)
Summary: Syntheses of Ketones and Aldehydes
826(3)
18-12 Reactions of Ketones and Aldehydes: Nucleophilic Addition
829(3)
Key Mechanism: Nucleophilic Additions to Carbonyl Groups
831(1)
18-13 The Wittig Reaction
832(4)
18-14 Hydration of Ketones and Aldehydes
836(2)
18-15 Formation of Cyanohydrins
838(2)
18-16 Formation of Imines
840(3)
Key Mechanism: Formation of Imines
840(3)
18-17 Condensations with Hydroxylamine and Hydrazines
843(2)
Summary: Condensations of Amines with Ketones and Aldehydes
844(1)
18-18 Formation of Acetals
845(5)
Key Mechanism: Formation of Acetals
846(2)
Problem-Solving Strategy: Proposing Reaction Mechanisms
848(2)
18-19 Use of Acetals as Protecting Groups
850(2)
18-20 Oxidation of Aldehydes
852(1)
18-21 Reductions of Ketones and Aldehydes
853(5)
Summary: Reactions of Ketones and Aldehydes
855(3)
Glossary
858(3)
Study Problems
861(9)
19 Amines 870(65)
19-1 Introduction
870(1)
19-2 Nomenclature of Amines
871(2)
19-3 Structure of Amines
873(2)
19-4 Physical Properties of Amines
875(2)
19-5 Basicity of Amines
877(1)
19-6 Effects on Amine Basicity
878(2)
19-7 Salts of Amines
880(2)
19-8 Amine Salts as Phase-Transfer Catalysts
882(2)
19-9 Spectroscopy of Amines
884(4)
19-10 Reactions of Amines with Ketones and Aldehydes (Review)
888(1)
19-11 Aromatic Substitution of Arylamines and Pyridine (Review)
888(4)
19-12 Alkylation of Amines by Alkyl Halides
892(1)
19-13 Acylation of Amines by Acid Chlorides
893(2)
19-14 Formation of Sulfonamides
895(2)
19-15 Amines as Leaving Groups: The Hofmann Elimination
897(3)
19-16 Oxidation of Amines: The Cope Elimination
900(2)
19-17 Reactions of Amines with Nitrous Acid
902(2)
19-18 Reactions of Arenediazonium Salts
904(7)
Summary: Reactions of Amines
908(3)
19-19 Synthesis of Amines by Reductive Amination
911(2)
19-20 Synthesis of Amines by Acylation-Reduction
913(2)
19-21 Syntheses Limited to Primary Amines
915(8)
Summary: Synthesis of Amines
921(2)
Chapter 19 Glossary
923(3)
Study Problems
926(9)
20 Carboxylic Acids 935(43)
20-1 Introduction
935(1)
20-2 Nomenclature of Carboxylic Acids
935(4)
20-3 Structure and Physical Properties of Carboxylic Acids
939(1)
20-4 Acidity of Carboxylic Acids
940(4)
20-5 Salts of Carboxylic Acids
944(3)
20-6 Commercial Sources of Carboxylic Acids
947(1)
20-7 Spectroscopy of Carboxylic Acids
948(4)
20-8 Synthesis of Carboxylic Acids
952(5)
Summary: Syntheses of Carboxylic Acids
955(2)
20-9 Reactions of Carboxylic Acids and Derivatives; Nucleophilic Acyl Substitution
957(1)
20-10 Condensation of Acids with Alcohols: The Fischer Esterification
958(4)
Key Mechanism: Fischer Esterification
959(3)
20-11 Esterification Using Diazomethane
962(1)
20-12 Condensation of Acids with Amines: Direct Synthesis of Amides
963(1)
20-13 Reduction of Carboxylic Acids
963(2)
20-14 Alkylation of Carboxylic Acids to Form Ketones
965(1)
20-15 Synthesis and Use of Acid Chlorides
966(4)
Summary: Reactions of Carboxylic Acids
968(2)
Chapter 20 Glossary
970(1)
Study Problems
971(7)
21 Carboxylic Acid Derivatives 978(63)
21-1 Introduction
978(1)
21-2 Structure and Nomenclature of Acid Derivatives
979(6)
21-3 Physical Properties of Carboxylic Acid Derivatives
985(3)
21-4 Spectroscopy of Carboxylic Acid Derivatives
988(6)
21-5 Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution
994(9)
Key Mechanism: Addition-Elimination Mechanism of Nucleophilic Acyl Substitution
995(8)
21-6 Transesterification
1003(3)
21-7 Hydrolysis of Carboxylic Acid Derivatives
1006(5)
21-8 Reduction of Acid Derivatives
1011(2)
21-9 Reactions of Acid Derivatives with Organometallic Reagents
1013(1)
21-10 Summary of the Chemistry of Acid Chlorides
1014(2)
21-11 Summary of the Chemistry of Anhydrides
1016(3)
21-12 Summary of the Chemistry of Esters
1019(3)
21-13 Summary of the Chemistry of Amides
1022(3)
21-14 Summary of the Chemistry of Nitriles
1025(1)
21-15 Thioesters
1026(2)
21-16 Esters and Amides of Carbonic Acid
1028(2)
Chapter 21 Glossary
1030(2)
Study Problems
1032(9)
22 Condensations and Alpha Substitutions of Carbonyl Compounds 1041(56)
22-1 Introduction
1041(1)
22-2 Enols and Enolate Ions
1042(4)
22-3 Alpha Halogenation of Ketones
1046(5)
22-4 a Bromination of Acids: The HVZ Reaction
1051(1)
22-5 Alkylation of Enolate Ions
1052(1)
22-6 Formation and Alkylation of Enamines
1053(3)
22-7 The Aldol Condensation of Ketones and Aldehydes
1056(4)
Key Mechanism: Base-Catalyzed Aldol Condensation
1056(4)
22-8 Dehydration of Aldol Products
1060(1)
Key Mechanism: Base-Catalyzed Dehydration of an Aldol
1060(1)
22-9 Crossed Aldol Condensations
1061(3)
Problem-Solving Strategy: Proposing Reaction Mechanisms
1062(2)
22-10 Aldol Cyclizations
1064(1)
22-11 Planning Syntheses Using Aldol Condensations
1065(2)
22-12 The Claisen Ester Condensation
1067(3)
Key Mechanism: The Claisen Ester Condensation
1067(3)
22-13 The Dieckmann Condensation: A Claisen Cyclization
1070(1)
22-14 Crossed Claisen Condensations
1071(3)
22-15 Syntheses Using /3-Dicarbonyl Compounds
1074(2)
22-16 The Malonic Ester Synthesis
1076(3)
22-17 The Acetoacetic Ester Synthesis
1079(2)
22-18 Conjugate Additions: The Michael Reaction
1081(4)
22-19 The Robinson Annulation
1085(3)
Problem-Solving Strategy: Proposing Reaction
Mechanisms
1086(2)
Summary: Enolate Additions and Condensations
1088(2)
Chapter 22 Glossary
1090(2)
Study Problems
1092(5)
23 Carbohydrates and Nucleic Acids 1097(56)
23-1 Introduction
1097(1)
23-2 Classification of Carbohydrates
1098(1)
23-3 Monosaccharides
1099(3)
23-4 Erythro and Threo Diastereomers
1102(1)
23-5 Epimers
1103(1)
23-6 Cyclic Structures of Monosaccharides
1104(4)
23-7 Anomers of Monosaccharides; Mutarotation
1108(2)
23-8 Reactions of Monosaccharides: Side Reactions in Base
1110(2)
23-9 Reduction of Monosaccharides
1112(1)
23-10 Oxidation of Monosaccharides; Reducing Sugars
1113(2)
23-11 Nonreducing Sugars: Formation of Glycosides
1115(2)
23-12 Ether and Ester Formation
1117(2)
23-13 Reactions with Phenylhydrazine: Osazone Formation
1119(1)
23-14 Chain Shortening: The Ruff Degradation
1120(1)
23-15 Chain Lengthening: The Kiliani-Fischer Synthesis
1121(3)
Summary: Reactions of Sugars
1122(2)
23-16 Fischer's Proof of the Configuration of Glucose
1124(3)
23-17 Determination of Ring Size; Periodic Acid Cleavage of Sugars
1127(2)
23-18 Disaccharides
1129(5)
23-19 Polysaccharides
1134(3)
23-20 Nucleic Acids: Introduction
1137(2)
23-21 Ribonucleosides and Ribonucleotides
1139(2)
23-22 The Structure of Ribonucleic Acid
1141(1)
23-23 Deoxyribose and the Structure of Deoxyribonucleic Acid
1141(4)
23-24 Additional Functions of Nucleotides
1145(2)
Chapter 23 Glossary
1147(2)
Study Problems
1149(4)
24 Amino Acids, Peptides, and Proteins 1153(47)
24-1 Introduction
1153(1)
24-2 Structure and Stereochemistry of the a-Amino Acids
1154(4)
24-3 Acid-Base Properties of Amino Acids
1158(2)
24-4 Isoelectric Points and Electrophoresis
1160(1)
24-5 Synthesis of Amino Acids
1161(6)
Summary: Syntheses of Amino Acids
1166(1)
24-6 Resolution of Amino Acids
1167(1)
24-7 Reactions of Amino Acids
1167(3)
Summary: Reactions of Amino Acids
1170(1)
24-8 Structure and Nomenclature of Peptides and Proteins
1170(4)
24-9 Peptide Structure Determination
1174(6)
24-10 Solution-Phase Peptide Synthesis
1180(3)
24-11 Solid-Phase Peptide Synthesis
1183(5)
24-12 Classification of Proteins
1188(1)
24-13 Levels of Protein Structure
1189(2)
24-14 Protein Denaturation
1191(2)
Chapter 24 Glossary
1193(3)
Study Problems
1196(4)
25 Lipids 1200(22)
25-1 Introduction
1200(1)
25-2 Waxes
1200(1)
25-3 Triglycerides
1201(3)
25-4 Saponification of Fats and Oils; Soaps and Detergents
1204(4)
25-5 Phospholipids
1208(1)
25-6 Steroids
1209(3)
25-7 Prostaglandins
1212(1)
25-8 Terpenes
1213(4)
Chapter 25 Glossary
1217(1)
Study Problems
1218(4)
26 Synthetic Polymers 1222(21)
26-1 Introduction
1222(1)
26-2 Addition Polymers
1223(6)
26-3 Stereochemistry of Polymers
1229(1)
26-4 Stereochemical Control of Polymerization; Ziegler-Natta Catalysts
1230(1)
26-5 Natural and Synthetic Rubbers
1230(2)
26-6 Copolymers of Two or More Monomers
1232(1)
26-7 Condensation Polymers
1232(4)
26-8 Polymer Structure and Properties
1236(2)
Chapter 26 Glossary
1238(2)
Study Problems
1240(3)
Appendices 1243
1A NMR Absorption Positions of Protons in Various Structural Environments
1244(2)
1B Spin-Spin Coupling Constants
1246(1)
1C 13C Chemical Shifts in Organic Compounds
1247(1)
2A Characteristic Infrared Group Frequencies
1248(3)
2B IR: Characteristic Infrared Absorptions of Functional Groups
1251(2)
3 UV: The Woodward-Fieser Rules for Predicting UV-Visible Spectra
1253(4)
4A Methods and Suggestions for Proposing Mechanisms
1257(3)
4B Suggestions for Developing Multistep Syntheses
1260(1)
5 pKa Values for Representative Compounds
1261
Answers to Selected Problems A1
Photo Credits PC1
Index l1


Please wait while the item is added to your cart...