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Organic Chemistry (with Organic ChemistryNOW)

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Edition:
2nd
ISBN13:

9780534389512

ISBN10:
0534389511
Format:
Hardcover
Pub. Date:
1/31/2005
Publisher(s):
Cengage Learning
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Summary

ORGANIC CHEMISTRY, Second Edition - the first mechanistic-oriented book written at a level that organic chemistry students will understand! Specifically, the focus on mechanisms is a unifying theme, rather then just an organizing principle. Organizationally mainstream, it is unique in bringing in mechanisms as a unifying principle, and reactions are organized by mechanism type not by functional groups. And now, text/media integration has never been so seamless with the introduction of Organic ChemistryNow for ORGANIC CHEMISTRY, Second Edition.

Table of Contents

PREFACE xxvi
1 A SIMPLE MODEL FOR CHEMICAL BONDS 1(29)
1.1 The Field of Organic Chemistry
1(2)
1.2 Simple Atomic Structure
3(1)
1.3 Ionic Bonding
4(1)
1.4 Covalent Bonding
5(1)
1.5 Lewis Structures
6(5)
1.6 Covalent Ions
11(1)
1.7 Formal Charges
11(4)
1.8 Resonance
15(2)
1.9 Polar Bonds
17(1)
1.10 Shapes of Molecules
18(4)
1.11 Dipole Moments
22(2)
Review of Mastery Goals
24(1)
Additional Problems
25(5)
2 ORGANIC COMPOUNDS: A FIRST LOOK 30(31)
2.1 Common Bonding Situations
30(3)
2.2 Bond Strengths and Bond Lengths
33(1)
2.3 Constitutional Isomers
34(5)
2.4 Degree of Unsaturation
39(5)
2.3 Physical Properties and Molecular Structure
44(2)
2.6 Melting Points, Boiling Points, and Solubilities
46(4)
Focus On: Boiling Points of Fuels
48(2)
2.7 Introduction to Functional Groups
50(2)
Review of Mastery Goals
52(1)
Additional Problems
53(8)
3 ORBITALS AND BONDING 61(42)
3.1 Atomic Orbitals
61(4)
3.2 Molecular Orbitals
65(4)
3.3 Single Bonds and sp3 Hybridization
69(2)
3.4 Double Bonds and sp2 Hybridization
71(5)
3.5 Triple Bonds and sp Hybridization
76(2)
3.6 Resonance and MO Theory
78(3)
3.7 Rules for Resonance Structures
81(5)
3.8 Types of Resonance Interactions
86(9)
Focus On: Resonance and the Bond Lengths of Naphthalene
94(1)
3.9 Molecular Orbital Energies
95(2)
Review of Mastery Goals
97(1)
Additional Problems
97(6)
4 THE ACID-BASE REACTION 103(39)
4.1 Definitions
103(4)
4.2 The Acid-Base Equilibrium
107(4)
4.3 Rate of the Acid-Base Reaction
111(3)
4.4 Effect of the Atom Bonded to the Hydrogen on Acidity
114(2)
4.5 Inductive Effects
116(3)
4.6 Hydrogen Bonding
119(1)
4.7 Hybridization
120(1)
4.8 Resonance
120(8)
Focus On: Calcium Carbide
121(7)
4.9 Tables of Acids and Bases
128(4)
4.10 Acidity and Basicity of Functional Groups and Solvents
132(3)
Review of Mastery Goals
135(1)
Additional Problems
135(7)
5 FUNCTIONAL GROUPS AND NOMENCLATURE I 142(36)
5.1 Alkanes
142(3)
5.2 Common Nomenclature of Alkanes
145(1)
5.3 Systematic Nomenclature of Alkanes
146(9)
Focus On: The Energy Content of Fuels
146(9)
5.4 Systematic Nomenclature of Cycloalkanes
155(2)
5.5 Alkenes
157(3)
5.6 Alkynes
160(1)
5.7 Alkyl Halides
161(1)
5.8 Alcohols
162(5)
Focus On Biological Chemistry: Chlorinated Organic Compounds
164(3)
5.9 Ethers
167(1)
5.10 Amines
168(3)
Review of Mastery Goals
171(1)
Additional Problems
172(6)
6 STEREOCHEMISTRY I: CIS-TRANS ISOMERS AND CONFORMATIONS 178(41)
6.1 Cis-Trans Isomers
179(4)
6.2 Designating the Configuration of Cis-Trans Isomers
183(3)
6.3 Conformations
186(7)
6.4 Conformations of Cyclic Molecules
193(3)
6.5 Conformations of Cyclohexane
196(5)
6.6 Conformations of Other Rings
201(1)
6.7 Conformations of Cyclohexanes with One Substituent
202(3)
6.8 Conformations of Cyclohexanes with Two or More Substituents
205(9)
Focus On: How Much Strain Is Too Much?
206(8)
Review of Mastery Goals
214(1)
Additional Problems
214(5)
7 STEREOCHEMISTRY II: CHIRAL MOLECULES 219(38)
7.1 Chiral Molecules
219(2)
7.2 Recognizing Chiral Molecules
221(3)
7.3 Designating Configuration of Enantiomers
224(3)
7.4 Properties of Enantiomers
227(3)
7.5 Molecules with Multiple Chirality Centers
230(4)
7.6 Stereoisomers and Cyclic Compounds
234(2)
7.7 Resolution: Separating Enantiomers
236(1)
7.8 Fischer Projections
237(5)
Focus On: The Historical Development of Understanding Stereochemistry
238(4)
7.9 Reactions That Produce Enantiomers
242(2)
Focus On: Pharmaceuticals and Chirality
243(1)
7.10 Other Chiral Compounds
244(3)
Review of Mastery Goals
247(1)
Visual Summary of Isomers
248(1)
Additional Problems
249(8)
8 NUCLEOPHILIC SUBSTITUTION REACTIONS: REACTIONS OF ALKYL HALIDES, ALCOHOLS, AND RELATED COMPOUNDS 257(56)
8.1 The General Reaction
257(2)
8.2 Reaction Mechanisms
259(1)
8.3 Bimolecular Nucleophilic Substitution
259(2)
8.4 Stereochemistry of the SN2 Reaction
261(3)
8.5 Effect of Substituents on the Rate of the SN2 Reaction
264(4)
8.6 Unimolecular Nucleophilic Substitution
268(4)
8.7 Effect of Substituents on the Rate of the SN1 Reaction
272(4)
Focus On: The llriphenyhnethyl Carbocation
274(2)
8.8 Stereochemistry of the SN1 Reaction
276(3)
8.9 Leaving Groups
279(5)
8.10 Nucleophiles
284(2)
8.11 Effect of Solvent
286(3)
8.12 Competition between SN1 and SN2 Reactions
289(3)
8.13 Intramolecular Reactions
292(2)
8.14 Competing Reactions
294(7)
Focus On: Carbocation Rearrangements in Superacids
299(2)
Review of Mastery Goals
301(1)
Visual Summary of Key Reactions
301(1)
Additional Prohknis
302(11)
9 ELIMINATION REACTIONS: REACTIONS OF ALKYL HALIDES, ALCOHOLS, AND RELATED COMPOUNDS 313(35)
9.1 The General Reaction
313(1)
9.2 Bimolecular Elimination
314(2)
Focus On Biological Chemistry: DDT Resistant Insects
316(1)
9.3 Stereochemistry of the E2 Reaction
316(7)
9.4 Direction of Elimination
323(6)
9.5 Unimolecular Elimination
329(2)
9.6 Regiochemistry and Stereochemistry of the El Reaction
331(3)
Focus On: The Elcb Mechanism
333(1)
9.7 The Competition between Elimination and Substitution
334(6)
Focus On Biological Chemistry: Biological Elimination
Reactions
340(1)
Review of Mastery Goals
341(1)
Visual Summary of Key Reactions
341(1)
Additional Problems
341(7)
10 SYNTHETIC USES OF SUBSTITUTION AND ELIMINATION REACTIONS: INTERCONVERTING FUNCTIONAL GROUPS 348(56)
10.1 Substitution Reactions
348(1)
10.2 Preparation of Alcohols
349(3)
10.3 Preparation of Ethers
352(5)
10.4 Preparation of Esters
357(1)
10.5 Preparation of Alkyl Halides
358(4)
10.6 Preparation of Amines
362(6)
Focus On Biological Chemistry: Biological Alkylations and Poisons
365(3)
10.7 Preparation of Hydrocarbons
368(1)
10.8 Formation of Carbon-Carbon Bonds
369(2)
10.9 Phosphorus and Sulfur Nucleophiles
371(1)
10.10 Ring Opening of Epoxides
372(4)
Focus On: Uses of Epoxides in Industry
375(1)
10.11 Elimination of Hydrogen Halides (Dehydrohalogenation)
376(1)
10.12 Preparation of Alkynes
377(1)
10.13 Dehydration
378(2)
10.14 Eliminations to Form Carbon-Oxygen Double Bonds; Oxidation Reactions
380(5)
Focus On: Environmentally Friendly Chemistry (Green Chemistry)
384(1)
10.15 The Strategy of Organic Synthesis
385(4)
Review of Mastery Goals
389(1)
Visual Summary of Key Reactions
390(4)
Integrated Practice Problem
394(1)
Additional Problems
395(9)
11 ADDITIONS TO CARBON-CARBON DOUBLE AND TRIPLE BONDS: REACTIONS OF ALKENES AND ALKYNES 404(62)
11.1 The General Mechanism
405(1)
11.2 Addition of Hydrogen Halides
406(6)
11.3 Addition of Water (Hydration)
412(1)
11.4 Addition of Halogens
413(6)
11.5 Halohydrin Formation
419(4)
Focus On: Industrial Addition Reactions
421(2)
11.6 Oxymercuration-Reduction
423(3)
11.7 Hydroboration-Oxidation
426(9)
Focus On: Chiral Boranes in Organic Synthesis
433(2)
11.8 Addition of Carbenes
435(3)
11.9 Epoxidation
438(1)
11.10 Hydroxylation
439(2)
11.11 Ozonolysis
441(3)
11.12 Catalytic Hydrogenation
444(2)
11.13 Additions to Conjugated Dienes
446(5)
Focus On: Asymmetric Hydrogenation
449(2)
11.14 Synthesis
451(2)
Review of Mastery Goals
453(1)
Visual Summary of Key Reactions
454(3)
Integrated Practice Problem
457(1)
Additional Problems
458(8)
12 FUNCTIONAL GROUPS AND NOMENCLATURE II 466(34)
12.1 Aromatic Hydrocarbons
466(6)
Focus On: Structure Proof by the Number of Isomers
469(3)
12.2 Phenols
472(1)
12.3 Aldehydes and Ketones
473(4)
12.4 Carboxylic Acids
477(2)
12.5 Derivatives of Carboxylic Acids
479(9)
Focus On: Fragrant Organic Compounds
486(2)
12.6 Sulfur and Phosphorus Compounds
488(3)
12.7 Nomenclature of Compounds with Several Functional Groups
491(9)
Review of Mastery Goals
494(1)
Additional Problems
494(6)
13 INFRARED SPECTROSCOPY 500(43)
13.1 Electromagnetic Radiation
501(1)
13.2 Interaction of Electromagnetic Radiation with Molecules
502(1)
13.3 The Electromagnetic Spectrum
503(2)
13.4 Infrared Spectroscopy
505(2)
13.5 Generalizations
507(1)
13.6 The Hydrogen Region
508(7)
13.7 The Triple-Bond Region
515(3)
Focus On: Remote Sensing of Automobile Pollutants
516(2)
13.8 The Double-Bond Region
518(2)
13.9 The Fingerprint Region
520(1)
13.10 Interpretation of IR Spectra
521(12)
Review of Mastery Goals
533(1)
Additional Problems
533(10)
14 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY 543(66)
14.1 Proton Magnetic Resonance Spectroscopy
543(2)
14.2 Theory of H-NMR
545(2)
14.3 The Chemical Shift
547(9)
14.4 Spin Coupling
556(6)
14.5 Complex Coupling
562(1)
14.6 Chemical Exchange
563(1)
14.7 Deuterium
563(3)
Focus On: NMR Spectroscopy of Carbocations in Superacid
565(1)
14.8 Interpretation of H-NMR Spectra
566(8)
Focus On: Magnetic Resonance Imaging
572(2)
14.9 Carbon-13 Magnetic Resonance Spectroscopy
574(9)
14.10 Solved Problems Employing IR and NMR Spectra
583(12)
Review of Mastery Goals
595(1)
Additional Problems
596(13)
15 ULTRAVIOLET-VISIBLE SPECTROSCOPY AND MASS SPECTROMETRY 609
15.1 Ultraviolet-Visible Spectroscopy
609(3)
15.2 Types of Electronic Transitions
612(3)
15.3 UV Visible Spectroscopy in Structure Determination
615(2)
Focus On: Ozone, Ultraviolet Radiation, and Sunscreens
616(1)
15.4 Mass Spectrometry
617(2)
15.5 Determining the Molecular Formula
619(5)
15.6 Fragmentation of the Molecular Ion
624(10)
Focus On: Gas Chromatography and Mass Spectrometry
633(1)
Review of Mastery Goals
634(1)
Additional Problems
634
16 BENZENE AND AROMATIC COMPOUNDS 042(629)
16.1 Benzene
642(2)
16.2 Resonance Energy of Benzene
644(2)
16.3 Molecular Orbital Model for Cyclic Conjugated Molecules
646(3)
16.4 Cyclobutadiene
649(2)
16.5 Hackel's Rule
651(1)
16.6 Cyclooctatetraene
652(1)
16.7 Heterocyclic Aromatic Compounds
653(2)
16.8 Polycyclic Aromatic Hydrocarbons
655(2)
Focus On: Carcinogenic Polycyclic Aromatic Hydrocarbons
657(1)
16.9 NMR and Aromaticity
657(2)
16.10 Annulenes
659(2)
16.11 Aromatic and Antiaromatic Ions
661(4)
Focus On: Buckminsterfullerene, a New Form of Carbon
663(2)
Review of Mastery Goals
665(1)
Additional Problems
665(6)
17 AROMATIC SUBSTITUTION REACTIONS 671(68)
17.1 Mechanism for Electrophilic Aromatic Substitution
671(3)
17.2 Effect of Substituents
674(8)
17.3 Effect of Multiple Substituents
682(1)
17.4 Nitration
683(3)
17.5 Halogenation
686(3)
17.6 Sulfonation
689(1)
17.7 Friedel-Crafts Allrylation
690(6)
Focus On: Synthetic Detergents, BHT, and BHA
694(2)
17.8 Friedel-Crafts Acylation
696(3)
17.9 Electrophilic Substitutions of Polycyclic Aromatic Compounds
699(1)
17.10 Nucleophilic Aromatic Substitution: Diazonium Ions
700(3)
17.11 Nucleophilic Aromatic Substitution: Addition-Elimination
703(2)
17.12 Nucleophilic Aromatic Substitution: Elimination-Addition
705(4)
Focus On: Experimental Evidence for the Benzyne Mechanism
708(1)
17.11 Some Additional Useful Reactions
709(4)
17.14 Synthesis of Aromatic Compounds
713(6)
Review of Mastery Goals
719(1)
Visual Summary of Key Reactions
719(4)
Intergrated Practice Problem
723(1)
Additional Problems
724(15)
18 ADDITIONS TO THE CARBONYL GROUPS REACTIONS OF ALDEHYDES AND KETONES 739(64)
18.1 General Mechanisms
740(2)
18.2 Addition of Hydride; Reduction of Aldehydes and Ketones
742(2)
18.3 Addition of Water
744(4)
18.4 Addition of Hydrogen Cyanide
748(3)
18.5 Preparation and Properties of Organometallic Nucleophiles
751(2)
18.6 Addition of Organometallic Nucleophiles
753(5)
18.7 Addition of Phosphorus Ylides; The Wittig Reaction
758(7)
Focus On: Synthesis of Vitamin A
763(2)
18.8 Addition of Nitrogen Nucleophiles
765(10)
Focus On Biological Chemistry: Imines in Living Organisms
773(2)
18.9 Addition of Alcohols
775(4)
18.10 Conjugate Additions
779(5)
18.11 Synthesis
784(3)
Review of Mastery Goals
787(1)
Visual Summary of Key Reactions
787(2)
Integrated Practice Problem
789(1)
Additional Problems
790(13)
19 SUBSTITUTIONS AT THE CARBONYL GROUP: REACTIONS OF CARBOXYLIC ACIDS AND DERIVATIVES 803(55)
19.1 The General Mechanism
803(5)
19.2 Preparation of Acyl Chlorides
808(2)
19.3 Preparation of Anhydrides
810(1)
19.4 Preparation of Esters
811(4)
19.5 Preparation of Carboxylic Acids
815(9)
Focus On: The Preparation of Soap
819(5)
19.6 Preparation of Amides
824(2)
19.7 Reaction with Hydride Nucleophiles
826(4)
19.8 Reduction of Acid Derivatives to Aldehydes
830(2)
19.9 Reactions with Organometallic Nucleophiles
832(2)
19.10 Preparation of Ketones
834(2)
19.11 Derivatives of Sulfur and Phosphorus Acids
836(4)
Focus On Biological Chemistry: Nerve Gases and Pesticides
838(2)
Review of Mastery Goals
840(1)
Visual Summary of Key Reactions
840(3)
Integrated Practice Problem
843(1)
Additional Problems
843(15)
20 ENOLATE AND OTHER CARBON NUCLEOPHILES 858(60)
20.1 Enols and Enolate Anions
859(3)
20.2 Halogenation of the a-Carbon
862(2)
20.3 Alkylation of Enolate Anions
864(3)
20.4 Alkylation of More Stabilized Anions
867(6)
20.5 The Aldol Condensation
873(7)
Focus On Biological Chemistry: The Reverse Aldol Reaction in Metabolism
880(1)
20.6 Ester Condensations
880(7)
Focus On: An Industrial Aldol Reaction
886(1)
20.7 Carbon and Hydrogen Leaving Groups
887(2)
20.8 Enamines
889(2)
20.9 Other Carbon Nucleophiles
891(3)
20.10 Conjugate Additions
894(4)
20.11 Synthesis
898(4)
Review of Mastery Goals
902(1)
Visual Summary of Key Reactions
902(2)
Integrated Practice Problem
904(1)
Additional Problems
905(13)
21 THE CHEMISTRY OF RADICALS 918(38)
21.1 Radicals
918(1)
21.2 Stability of Radicals
919(2)
21.3 Geometry of Carbon Radicals
921(1)
21.4 Generation of Radicals
922(1)
213 General Radical Reactions
923(4)
Focus On: The 'Itiphenylmethyl Radical
926(1)
21.6 Halogenation
927(7)
21.7 Dehalogenation
934(1)
21.8 Autoxidation
935(4)
Focus On Biological Chemistry: Vitamin E and Lipid Autoxidation
937(2)
21.9 Radical Additions to Alkenes
939(2)
21.10 Reductions and Radical Anions
941(5)
Review of Mastery Goals
946(1)
Visual Summary of Key Reactions
947(1)
Additional Problems
948(8)
22 PERICYCLIC REACTIONS 956(55)
22.1 Pericyclic Reactions
956(3)
22.2 MO Theory for Conjugated Molecules
959(6)
22.3 Electrocyclic Reactions
965(5)
22.4 Examples of Electrocyclic Reactions
970(5)
Focus On: Dewar Benzene
973(2)
22.5 Cycloaddition Reactions
975(2)
22.6 The Diels-Alder Reaction
977(7)
22.7 Other Cycloaddition Reactions
984(2)
22.8 Sigmatropic Rearrangements
986(4)
22.9 Examples of Sigmatropic Rearrangements
990(4)
Focus On Biological Chemistry: Pericyclic Reactions and Vitamin D
993(1)
22.10 Rearrangements to Electron-Deficient Centers
994(5)
Review of Mastery Goals
999(1)
Visual Summary of Key Reactions
999(2)
Additional Problems
1001(10)
23 THE SYNTHESIS OF ORGANIC COMPOUNDS 1011(42)
23.1 Protecting Groups for Alcohols
1011(4)
23.2 Protecting Groups for Aldehydes and Ketones
1015(1)
23.3 Protecting Groups for Carboxylic Acids
1016(2)
23.4 Protecting Groups for Amines
1018(2)
23.5 Retrosynthetic Analysis
1020(6)
Focus On Biological Chemistry: Pheromones
1025(1)
23.6 Examples of Syntheses
1026(3)
23.7 Reactions That Form Carbon-Carbon Bonds
1029(1)
23.8 Preparation of Functional Groups
1030(15)
Review of Mastery Goals
1045(1)
Additional Problems
1046(7)
24 SYNTHETIC POLYMERS 1053(32)
24.1 Radical Chain Polymerization
1053(4)
24.2 Structures of Polymers
1057(3)
24.3 Ionic Polymerization
1060(2)
Focus On: Super Glue
1062(1)
24.4 Coordination Polymerization
1062(2)
24.5 Physical Properties of Polymers
1064(2)
24.6 Major Thermoplastic Addition Polymers
1066(2)
24.7 Elastomers
1068(2)
24.8 Condensation Polymers
1070(5)
24.9 Thermoset Polymers
1075(2)
24.10 Chemical Properties of Polymers
1077(4)
Focus On: Recycling Plastics
1080(1)
Review of Mastery Goals
1081(1)
Additional Problems
1081(4)
25 CARBOHYDRATES 1085(38)
25.1 Structures of Carbohydrates
1085(1)
25.2 Stereochemistry of Carbohydrates
1086(4)
25.3 Cyclization of Monosaccharides
1090(4)
25.4 Reactions of Monosaccharides
1094(11)
Focus On: The Determination of Anomer Configuration
1095(8)
Focus On: Artificial Sweeteners
1103(2)
25.5 Fischer's Structure Proof for Glucose
1105(5)
25.6 Disaccharides
1110(1)
25.7 Polysaccharides
1111(2)
25.8 Other Carbohydrate-Containing Compounds
1113(10)
Focus On Biological Chemistry: Blood Groups
1115(1)
Review of Mastery Goals
1116(1)
Additional Problems
1117(6)
26 AMINO ACIDS, PEPTIDES, AND PROTEINS 1123(39)
26.1 Amino Acids
1123(3)
26.2 Acid-Base Chemistry of Amino Acids
1126(4)
26.3 Chemical Reactions of Amino Acids
1130(1)
26.4 Laboratory Synthesis of Amino Acids
1131(6)
Focus On: Asymmetric Synthesis of Amino Acids
1135(2)
26.5 Peptides and Proteins
1137(3)
Focus On: NMR Spectra of Amides
1140(1)
26.6 Sequencing Peptides
1140(8)
26.7 Laboratory Synthesis of Peptides
1148(7)
26.8 Protein Structure
1155(1)
26.9 Enzymes
1156(2)
Review of Mastery Goals
1158(1)
Additional Problems
1158(4)
27 NUCLEOTIDES AND NUCLEIC ACIDS 1162(22)
27.1 Nucleosides and Nucleotides
1162(3)
27.2 Structure of DNA and RNA
1165(6)
Focus On: Tautomers of Guanine and Thymine
1170(1)
27.3 Replication, Transcription, and Translation
1171(4)
Focus On Biological Chemistry: Treatment of AIDS with AZT
1174(1)
27.4 Sequencing DNA
1175(3)
27.5 Laboratory Synthesis of DNA
1178(2)
Review of Mastery Goals
1180(1)
Additional Problems
1181(3)
28 OTHER NATURAL PRODUCTS 1184
28.1 Terpenes
1184(2)
28.2 Monoterpenes
1186(4)
28.3 Sesquiterpenes
1190(4)
28.4 Larger Terpenes
1194(2)
28.5 Steroids
1196(6)
Focus On: Syntheses That Mimic Nature
1200(2)
28.6 Synthesis of Steroids
1202(4)
Focus On: The Birth Control Pill
1204(2)
28.7 Alkaloids
1206(2)
28.8 Fats and Related Compounds
1208(3)
Focus On: Partially Hydrogenated Vegetable Oil
1210(1)
28.9 Prostaglandins
1211(2)
Review of Mastery Goals
1213(1)
Additional Problems
1213
APPENDIX: ANSWERS TO IN-CHAPTER PROBLEMS A-0
GLOSSARY G-0
INDEX I-0


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