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Organic Chemistry

ISBN: 9780534467739 | 0534467733
Edition: 4th
Format: Hardcover
Publisher: Brooks Cole
Pub. Date: 10/21/2004

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SummaryTable of Contents
This book provides an exciting introduction to organic chemistry for students majoring in chemistry and in related disciplines, especially the health and biological sciences. In this Fourth Edition, Brown, Foote, and Iverson build on the text's highly-praised hallmarks of unifying mechanistic themes, focusing on problem-solving, using applied problems from the pharmaceutical field, and making innovative use of color and emphasis on visualization. The new edition features increased coverage of mechanisms, more examples of bio-organic chemistry e... MORE
Covalent Bonding and Shapes of Molecules
1(55)
Electronic Structure of Atoms
2(3)
Lewis Model of Bonding
... MORE		5(13)
How To Draw Lewis Structures From Condensed Structural Formulas
14(2)
Chemical Connections The Octet Rule
16(2)
Functional Groups
18(5)
Bond Angles and Shapes of Molecules
23(5)
Chemical Connections Fullerene---A New Form of Carbon
27(1)
Polar and Nonpolar Molecules
28(1)
Resonance
29(5)
How To Draw Curved Arrows and Push Electrons
30(4)
Quantum or Wave Mechanics
34(3)
The Molecular Orbital and Valence Bond Theories of Covalent Bonding
37(19)
Summary
47(1)
Problems
48(5)
Additional Problems
53(3)
Alkanes and Cycloalkanes
56(55)
The Structure of Alkanes
57(1)
Constitutional Isomerism in Alkanes
58(3)
Nomenclature of Alkanes
61(4)
Cycloalkanes
65(3)
The IUPAC System---A General System of Nomenclature
68(2)
Conformations of Alkanes and Cycloalkanes
70(14)
How To Draw Alternative Chair Conformations of Cyclohexane
80(4)
Cis, Trans Isomerism in Cycloalkanes and Bicycloalkanes
84(9)
How To Convert Planao Cyclohexanes to Chair Cyclohexanes
88(4)
Chemical Connections The Poisonous Puffer Fish
92(1)
Physical Properties of Alkanes and Cycloalkanes
93(3)
Reactions of Alkanes
96(3)
Sources and Importance of Alkanes
99(12)
Chemical Connections Octane Rating: What Those Numbers at the Pump Mean
101(1)
Summary
102(1)
Key Reactions
103(1)
Problems
103(8)
Stereoisomerism and Chirality
111(40)
Stereoisomerism
111(1)
Chirality---The Handedness of Molecules
112(4)
How To Draw Chiral Molecules
114(2)
Naming Chiral Centers---The R,S System
116(4)
How To Assign R or S Configuration to a Chiral Center
118(2)
Acyclic Molecules with Two or More Chiral Centers
120(5)
Cyclic Molecules with Two or More Chiral Centers
125(5)
Properties of Stereoisomers
130(1)
Optical Activity---How Chirality Is Detected in the Laboratory
130(5)
Separation of Enantiomers---Resolution
135(4)
Connections to Biological Chemistry Amino Acids
138(1)
The Significance of Chirality in the Biological World
139(12)
Connections to Biological Chemistry Chiral Drugs
141(1)
Summary
142(1)
Problems
143(8)
Acids and Bases
151(30)
Arrhenius Acids and Bases
151(1)
Brønsted-Lowry Acids and Bases
152(6)
Acid Dissociation Constants, pKa, and the Relative Strengths of Acids and Bases
158(3)
The Position of Equilibrium in Acid-Base Reactions
161(3)
Connections to Biological Chemistry
The Ionization of Functional Groups at Physiological pH
164(1)
Molecular Structure and Acidity
164(6)
Lewis Acids and Bases
170(11)
Chemical Connections The Strongest Acid?
172(1)
Summary
173(1)
Key Reactions
174(1)
Problems
174(7)
Alkenes: Bonding, Nomenclature, and Properties
181(23)
Structure of Alkenes
183(3)
How To Calculate the Index of Hydrogen Deficiency
184(2)
Nomenclature of Alkenes
186(8)
Chemical Connections The Case of the Iowa and New York Strains of the European Corn Borer
193(1)
Physical Properties of Alkenes
194(1)
Naturally Occurring Alkenes---Terpene Hydrocarbons
194(10)
Connections to Biological Chemistry
The Importance of cis Double Bonds in Fats Versus Oils
196(2)
Summary
198(1)
Problems
198(6)
Reactions of Alkenes
204(60)
Reactions of Alkenes---An Overview
205(1)
Reaction Mechanisms
206(3)
Electrophilic Additions
209(20)
Hydroboration-Oxidation
229(3)
Oxidation
232(6)
How To Write a Balanced Half-Reaction
233(5)
Reduction
238(5)
Connections to Biological Chemistry
Trans Fatty Acids: What They Are and How to Avoid Them
242(1)
Molecules Containing Chiral Centers as Reactants or Products
243(21)
Summary
248(1)
Key Reactions
249(2)
Problems
251(9)
Interchapter: Summary of Stereochemical Terms
260(4)
Alkynes
264(28)
Structure of Alkynes
264(1)
Nomenclature of Alkynes
265(2)
Physical Properties of Alkynes
267(1)
Acidity of I-Alkynes
267(1)
Preparation of Alkynes
268(3)
Electrophilic Addition to Alkynes
271(3)
Hydration of Alkynes to Aldehydes and Ketones
274(5)
Reduction of Alkynes
279(2)
Organic Synthesis: Retrosynthetic Analysis
281(11)
Summary
284(1)
Key Reactions
284(2)
Problems
286(6)
Haloalkanes, Halogenation, and Radical Reactions
292(37)
Structure
292(1)
Nomenclature
293(2)
Physical Properties of Haloalkanes
295(4)
Chemical Connections Freons
298(1)
Preparation of Haloalkanes by Halogenation of Alkanes
299(5)
Mechanism of Halogenation of Alkanes
304(7)
Allylic Halogenation
311(5)
Radical Autoxidation
316(3)
Connections to Biological Chemistry Antioxidants
318(1)
Radical Addition of HBr to Alkenes
319(10)
Summary
321(1)
Key Reactions
322(1)
Problems
323(6)
Nucleophilic Substitution and β-Elimination
329(55)
Nucleophilic Substitution in Haloalkanes
330(2)
Solvents for Nucleophilic Substitution Reactions
332(2)
Mechanisms of Nucleophilic Aliphatic Substitution
334(2)
Experimental Evidence for SN1 and SN2 Mechanisms
336(15)
Analysis of Several Nucleophilic Substitution Reactions
351(3)
β-Elimination
354(2)
Mechanisms of β-Elimination
356(2)
Experimental Evidence for E1 and E2 Mechanisms
358(6)
Substitution Versus Elimination
364(3)
Phase-Transfer Catalysis
367(2)
Neighboring Group Participation
369(15)
Connections to Biological Chemistry
Mustard Gases and the Treatment of Neoplastic Diseases
372(1)
Summary
373(1)
Key Reactions
374(1)
Problems
375(9)
Alcohols
384(48)
Structure and Nomenclature of Alcohols
385(3)
Physical Properties of Alcohols
388(4)
Connections to Biological Chemistry
The Importance of Hydrogen Bonding in Drug-Receptor Interactions
390(2)
Acidity and Basicity of Alcohols
392(1)
Reaction of Alcohols with Active Metals
393(1)
Conversion of Alcohols to Haloalkanes and Sulfonates
394(7)
Acid-Catalyzed Dehydration of Alcohols
401(5)
The Pinacol Rearrangement
406(3)
Oxidation of Alcohols
409(8)
Chemical Connections Blood Alcohol Screening
412(2)
Connections to Biological Chemistry
The Oxidation of Alcohols by NAD+
414(3)
Thiols
417(15)
Summary
422(1)
Key Reactions
422(2)
Problems
424(8)
Ethers, Sulfides, and Epoxides
432(39)
Structure of Ethers
432(1)
Nomenclature of Ethers
433(1)
Physical Properties of Ethers
434(2)
Preparation of Ethers
436(4)
Reactions of Ethers
440(3)
Silyl Ethers as Protecting Groups
443(2)
Epoxides: Structure and Nomenclature
445(1)
Synthesis of Epoxides
446(5)
Reactions of Epoxides
451(3)
Ethylene Oxide and Epichlorohydrin: Building Blocks in Organic Synthesis
454(3)
Crown Ethers
457(1)
Thioethers
458(13)
Summary
460(1)
Key Reactions
460(3)
Problems
463(8)
Infrared Spectroscopy
471(22)
Electromagnetic Radiation
471(2)
Molecular Spectroscopy
473(1)
Infrared Spectroscopy
474(5)
Interpreting Infrared Spectra
479(10)
Solving Infrared Spectral Problems
489(4)
Summary
489(1)
Problems
490(3)
Nuclear Magnetic Resonance Spectroscopy
493(50)
Nuclear Spin States
494(1)
Orientation of Nuclear Spins in an Applied Magnetic Field
494(2)
Nuclear Magnetic Resonance
496(2)
An NMR Spectrometer
498(2)
Equivalent Hydrogens
500(2)
Signal Areas
502(2)
Chemical Shift
504(4)
Signal Splitting and the (n + 1) Rule
508(2)
The Origins of Signal Splitting
510(8)
Stereochemistry and Topicity
518(4)
Chemical Connections Magnetic Resonance Imaging
520(2)
13C-NMR
522(2)
The DEPT Method
524(3)
Interpretation of NMR Spectra
527(16)
How To Solve NMR Spectral Problems
530(3)
Summary
533(1)
Problems
534(9)
Mass Spectrometry
543(24)
A Mass Spectrometer
544(3)
Features of a Mass Spectrum
547(4)
Interpreting Mass Spectra
551(10)
Connections to Biological Chemistry
Mass Spectrometry of Biological Macromolecules
560(1)
Mass Spectrometry in the Organic Synthesis Laboratory and Other Applications
561(6)
Summary
561(1)
Problems
562(5)
Organometallic Compounds
567(17)
Organomagnesium and Organolithium Compounds
568(5)
Lithium Diorganocopper (Gilman) Reagents
573(3)
Carbenes and Carbenoids
576(8)
Summary
580(1)
Key Reactions
580(1)
Problems
581(3)
Aldehydes and Ketones
584(61)
Structure and Bonding
584(1)
Nomenclature
585(4)
Physical Properties
589(1)
Reactions
590(1)
Addition of Carbon Nucleophiles
591(5)
The Wittig Reaction
596(4)
Addition of Oxygen Nucleophiles
600(9)
Addition of Nitrogen Nucleophiles
609(4)
Keto-Enol Tautomerism
613(4)
Oxidation
617(2)
Reduction
619(6)
Connections to Biological Chemistry NADH: The Biological Equivalent of a Hydride Reducing Agent
620(5)
Reactions at an α-Carbon
625(20)
Summary
628(1)
Key Reactions
628(4)
Problems
632(13)
Carboxylic Acids
645(35)
Structure
645(1)
Nomenclature
646(3)
Physical Properties
649(3)
Chemical Connections
From Willow Bark to Aspirin and Beyond
650(2)
Acidity
652(4)
Preparation of Carboxylic Acids
656(2)
Reduction
658(2)
Esterification
660(5)
Chemical Connections
The Pyrethrins: Natural Insecticides of Plant Origin
662(2)
Chemical Connections Esters as Flavoring Agents
664(1)
Conversion to Acid Chlorides
665(2)
Decarboxylation
667(13)
Connections to Biological Chemistry
Ketone Bodies and Diabetes Mellitus
668(2)
Summary
670(1)
Key Reactions
670(2)
Problems
672(8)
Functional Derivatives of Carboxylic Acids
680(50)
Structure and Nomenclature
681(7)
Chemical Connections From Cocaine to Procaine and Beyond
683(1)
Chemical Connections From Moldy Clover to a Blood Thinner
684(2)
Chemical Connections The Penicillins and Cephalosporins: β-Lactam Antibiotics
686(1)
Connections to Biological Chemistry The Unique Structure of Amide Bonds
687(1)
Acidity of Amides, Imides, and Sulfonamides
688(2)
Characteristic Reactions
690(2)
Reaction with Water: Hydrolysis
692(9)
Reaction with Alcohols
701(3)
Reactions with Ammonia and Amines
704(2)
Reaction of Acid Chlorides with Salts of Carboxylic Acids
706(1)
Interconversion of Functional Derivatives
706(1)
Reactions with Organometallic Compounds
707(2)
Reduction
709(21)
Summary
714(1)
Key Reactions
714(3)
Problems
717(13)
Enolate Anions and Enamines
730(53)
Formation and Reactions of Enolate Anions: An Overview
730(2)
Aldol Reaction
732(6)
Claisen and Dieckmann Condensations
738(6)
Chemical Connections
Drugs That Lower Plasma Levels of Cholesterol
744(1)
Claisen and Aldol Condensations in the Biological World
744(3)
Enamines
747(3)
Acetoacetic Ester Synthesis
750(4)
Malonic Ester Synthesis
754(4)
Chemical Connections Ibuprofen: The Evolution of an Industrial Synthesis
756(2)
Conjugate Addition to α, β-Unsaturated Carbonyl Compounds
758(25)
Summary
766(1)
Key Reactions
766(2)
Problems
768(15)
Conjugated Systems
783(18)
Stability of Conjugated Dienes
783(4)
Electrophilic Addition to Conjugated Dienes
787(6)
UV-Visible Spectroscopy
793(8)
Chemical Connections Curry and Cancer
796(2)
Summary
798(1)
Key Reactions
798(1)
Problems
798(3)
Benzene and the Concept of Aromaticity
801(56)
The Structure of Benzene
802(4)
The Concept of Aromaticity
806(12)
Nomenclature
818(4)
Chemical Connections Carcinogenic Polynuclear Aromatic Hydrocarbons and Smoking
821(1)
Phenols
822(10)
Chemical Connections
Capsaicin, for Those Who Like It Hot
823(9)
Reactions at a Benzylic Position
832(25)
Summary
836(1)
Key Reactions
836(2)
Problems
838(19)
Reactions of Benzene and Its Derivatives
857(41)
Electrophilic Aromatic Substitution
858(10)
Disubstitution and Polysubstitution
868(8)
Nucleophilic Aromatic Substitution
876(22)
Summary
880(1)
Key Reactions
881(2)
Problems
883(15)
Amines
898(54)
Structure and Classification
898(2)
Nomenclature
900(2)
Chirality of Amines and Quaternary Ammonium Ions
902(2)
Physical Properties
904(2)
Chemical Connections
The Poison Dart Frogs of South America
905(1)
Basicity
906(7)
Connections to Biological Chemistry
The Planarity of --- NH2 Groups on Aromatic Rings
910(3)
Reactions with Acids
913(4)
Preparation
917(2)
Reaction with Nitrous Acid
919(8)
Hofmann Elimination
927(3)
Cope Elimination
930(22)
Summary
931(1)
Key Reactions
932(3)
Problems
935(17)
Carbon-Carbon Bond Formation and Synthesis
952(48)
Carbon-Carbon Bond-Forming Reactions from Earlier Chapters
953(1)
Organometallic Compounds
953(1)
Organopalladium Reagents---The Heck Reaction
954(7)
Organopalladium Reagents---The Suzuki Coupling
961(2)
Alkene Metathesis
963(3)
The Diels-Alder Reaction
966(9)
Pericyclic Reactions and Transition State Aromaticity
975(4)
Chemical Connections Singlet Oxygen
978(1)
The Synthesis of Enantiomerically Pure Target Molecules
979(21)
Summary
981(1)
Key Reactions
981(1)
Problems
982(18)
Carbohydrates
1000(36)
Monosaccharides
1001(5)
The Cyclic Structure of Monosaccharides
1006(5)
Chemical Connections L-Ascorbic Acid (Vitamin C)
1008(3)
Reactions of Monosaccharides
1011(6)
Chemical Connections Testing for Glucose
1016(1)
Disaccharides and Oligosaccharides
1017(4)
Chemical Connections
A, B, AB, and O Blood Group Substances
1020(1)
Polysaccharides
1021(3)
Chemical Connections High-Fructose Corn Syrup
1022(2)
Acidic Polysaccharides
1024(12)
Summary
1025(1)
Key Reactions
1026(2)
Problems
1028(8)
Lipids
1036(29)
Triglycerides
1036(4)
Soaps and Detergents
1040(2)
Prostaglandins
1042(3)
Steroids
1045(6)
Chemical Connections
Drugs That Lower Plasma Levels of Cholesterol
1050(1)
Phospholipids
1051(4)
Chemical Connections Snake Venom Phospholipases
1054(1)
Fat-Soluble Vitamins
1055(10)
Chemical Connections
Vitamin K, Blood Clotting, and Basicity
1058(1)
Summary
1059(1)
Problems
1060(5)
Amino Acids and Proteins
1065(39)
Amino Acids
1065(4)
Acid-Base Properties of Amino Acids
1069(5)
Polypeptides and Proteins
1074(1)
Primary Structure of Polypeptides and Proteins
1075(7)
Synthesis of Polypeptides
1082(5)
Three-Dimensional Shapes of Polypeptides and Proteins
1087(17)
Chemical Connections Spider Silk
1092(3)
Summary
1095(1)
Key Reactions
1096(1)
Problems
1097(7)
Nucleic Acids
1104(25)
Nucleosides and Nucleotides
1105(2)
The Structure of DNA
1107(8)
Chemical Connections The Search for Antiviral Drugs
1109(6)
Chemical Connections The Fountain of Youth
1115(1)
Ribonucleic Acids
1115(2)
The Genetic Code
1117(3)
Sequencing Nucleic Acids
1120(9)
Chemical Connections DNA Fingerprinting
1124(1)
Summary
1125(1)
Problems
1126(3)
Organic Polymer Chemistry
1129(1)
The Architecture of Polymers
1130(1)
Polymer Notation and Nomenclature
1131(1)
Molecular Weights of Polymers
1132(1)
Polymer Morphology---Crystalline Versus Amorphous Materials
1132(2)
Step-Growth Polymerizations
1134(8)
Chemical Connections Stitches That Dissolve
1141(1)
Chain-Growth Polymerizations
1142(4)
Chemical Connections
Organic Polymers That Conduct Electricity
1146(8)
Chemical Connections The Chemistry of Superglue
1154(4)
Chemical Connections Recycling of Plastics
1158(3)
Summary
1161(1)
Key Reactions
1161(1)
Problems
1162
Appendix 1 Thermodynamics and the Equilibrium Constant1(1)
Appendix 2 Major Classes of Organic Acids2(1)
Appendix 3 Bond Dissociation Enthalpies3(1)
Appendix 4 Characteristic 1H-NMR Chemical Shifts4(1)
Appendix 5 Characteristic 13C-NMR Chemical Shifts5(1)
Appendix 6 Characteristic Infrared Absorption Frequencies6(1)
Appendix 7 Electrostatic Potential Maps7
Glossary1(1)
Index1

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