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Organic Chemistry : A Short Course,9780618215362

Organic Chemistry : A Short Course

by ; ;
Edition:
11th
ISBN13:

9780618215362

ISBN10:
0618215360
Format:
Hardcover
Pub. Date:
7/18/2002
Publisher(s):
Brooks Cole
List Price: $262.33

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Table of Contents

Preface xviii
To the Student 1(5)
Bonding and Isomerism
6(35)
How Electrons Are Arranged in Atoms
6(2)
Ionic and Covalent Bonding
8(3)
Ionic Compounds
8(2)
The Covalent Bond
10(1)
Carbon and the Covalent Bond
11(2)
Carbon--Carbon Single Bonds
13(1)
Polar Covalent Bonds
14(1)
Multiple Covalent Bonds
15(2)
Valence
17(1)
Isomerism
18(1)
Writing Structural Formulas
19(2)
Abbreviated Structural Formulas
21(2)
Formal Charge
23(2)
Resonance
25(1)
Arrow Formalism
26(2)
The Orbital View of Bonding; the Sigma Bond
28(1)
Carbon sp3 Hybrid Orbitals
29(2)
Tetrahedral Carbon; the Bonding in Methane
31(1)
Classification According to Molecular Framework
32(1)
Acyclic Compounds
32(1)
Carbocyclic Compounds
33(1)
Heterocyclic Compounds
33(1)
Classification According to Functional Group
33(8)
Additional Problems
37(4)
Alkanes and Cycloalkanes; Conformational and Geometric Isomerism
41(30)
The Structures of Alkanes
41(2)
Nomenclature of Organic Compounds
43(1)
IUPAC Rules for Naming Alkanes
44(2)
Alkyl and Halogen Substituents
46(2)
Use of the IUPAC Rules
48(1)
Sources of Alkanes
49(1)
A Closer Look at Natural Gas
49(1)
Physical Properties of Alkanes and Nonbonding Intermolecular Interactions
50(2)
A Closer Look At Hydrogen Bonding
51(1)
Conformations of Alkanes
52(2)
Cycloalkane Nomenclature and Conformation
54(4)
Cis--trans Isomerism in Cycloalkanes
58(1)
Summary of Isomerism
59(2)
A Word About Isomers, Possible and Impossible
60(1)
Reactions of Alkanes
61(4)
Oxidation and Combustion; Alkanes as Fuels
61(2)
Halogenation of Alkanes
63(1)
A Word About Methane, Marsh Gas, and Miller's Experiment
64(1)
The Free-Radical Chain Mechanism of Halogenation
65(6)
Reaction Summary
67(1)
Mechanism Summary
67(1)
Additional Problems
67(4)
Alkenes and Alkynes
71(45)
Definition and Classification
71(2)
Nomenclature
73(3)
Some Facts About Double Bonds
76(1)
The Orbital Model of a Double Bond; the Pi Bond
76(3)
Cis--trans Isomerism in Alkenes
79(3)
A Word About The Chemistry of Vision
80(2)
Addition and Substitution Reactions Compared
82(1)
Polar Addition Reactions
82(2)
Addition of Halogens
83(1)
Addition of Water (Hydration)
83(1)
Addition of Acids
84(1)
Addition of Unsymmetric Reagents to Unsymmetric Alkenes; Markovnikov's Rule
84(2)
Mechanism of Electrophilic Addition to Alkenes
86(2)
Markovnikov's Rule Explained
88(2)
Reaction Equilibrium: What Makes a Reaction Go?
90(1)
Reaction Rates: How Fast Does a Reaction Go?
91(3)
Hydroboration of Alkenes
94(1)
Addition of Hydrogen
95(1)
Additions to Conjugated Systems
96(3)
Electrophilic Addition to Conjugated Dienes
96(2)
Cycloaddition to Conjugated Dienes: The Diels--Alder Reaction
98(1)
Free-Radical Additions; Polyethylene
99(2)
Oxidation of Alkenes
101(3)
Oxidation with Permanganate; a Chemical Test
101(1)
Ozonolysis of Alkenes
101(1)
A Word About Ethylene: Raw Material and Plant Hormone
102(1)
Other Alkene Oxidations
103(1)
Some Facts About Triple Bonds
104(1)
The Orbital Model of a Triple Bond
104(1)
Addition Reactions of Alkynes
105(3)
A Word About Petroleum, Gasoline, and Octane Number
106(2)
Acidity of Alkynes
108(8)
A Closer Look At Petroleum
109(1)
Reaction Summary
110(1)
Mechanism Summary
111(1)
Additional Problems
112(4)
Aromatic Compounds
116(30)
Some Facts About Benzene
117(1)
The Kekule Structure of Benzene
118(1)
Resonance Model for Benzene
119(1)
Orbital Model for Benzene
119(1)
Symbols for Benzene
120(1)
Nomenclature of Aromatic Compounds
120(3)
The Resonance Energy of Benzene
123(2)
Electrophilic Aromatic Substitution
125(1)
The Mechanism of Electrophilic Aromatic Substitution
126(4)
Halogenation
127(1)
Nitration
128(1)
Sulfonation
128(1)
Alkylation and Acylation
129(1)
Ring-Activating and Ring-Deactivating Substituents
130(1)
Ortho, Para-Directing, and Meta-Directing Groups
130(5)
Ortho, Para-Directing Groups
131(2)
Meta-Directing Groups
133(2)
Substituent Effects on Reactivity
135(1)
The Importance of Directing Effects in Synthesis
135(1)
Polycyclic Aromatic Hydrocarbons
136(10)
A Word About Polycyclic Aromatic Hydrocarbons and Cancer
137(1)
A Word About C60, an Aromatic Sphere: The Fullerenes
138(2)
A Closer Look At Polycyclic Aromatic Hydrocarbons
140(1)
Reaction Summary
141(1)
Mechanism Summary
142(1)
Additional Problems
142(4)
Stereoisomerism
146(34)
Chirality and Enantiomers
146(2)
Stereogenic Centers; the Stereogenic Carbon Atom
148(4)
Configuration and the R--S Convention
152(5)
The E--Z Convention for Cis--Trans Isomers
157(1)
Polarized Light and Optical Activity
158(4)
A Word About Pasteur's Experiments and the van't Hoff--LeBel Explanation
160(2)
Properties of Enantiomers
162(1)
Fischer Projection Formulas
163(2)
Compounds with More Than One Stereogenic Center; Diastereomers
165(2)
Meso Compounds; the Stereoisomers of Tartaric Acid
167(2)
Stereochemistry: A Recap of Definitions
169(1)
Stereochemistry and Chemical Reactions
170(3)
A Word About Enantiomers and Biological Activity
172(1)
Resolution of a Racemic Mixture
173(7)
A Closer Look At Thalidomide
174(1)
Additional Problems
175(5)
Organic Halogen Compounds: Substitution and Elimination Reactions
180(23)
Nucleophilic Substitution
180(1)
Examples of Nucleophilic Substitutions
181(4)
Nucleophilic Substitution Mechanisms
185(1)
The SN2 Mechanism
185(3)
The SN1 Mechanism
188(2)
The SN1 and SN2 Mechanisms Compared
190(3)
A Word About SN2 Reactions in Nature: Biological Methylations
192(1)
Dehydrohalogenation, an Elimination Reaction; the E2 and E1 Mechanisms
193(1)
Substitution and Elimination in Competition
194(2)
Tertiary Halides
194(1)
Primary Halides
195(1)
Secondary Halides
195(1)
Polyhalogenated Aliphatic Compounds
196(7)
A Word About CFCs, the Ozone Layer, and Trade-Offs
198(1)
A Word About Halogenated Organic Compounds from the Sea
199(1)
Reaction Summary
199(1)
Mechanism Summary
200(1)
Additional Problems
200(3)
Alcohols, Phenols, and Thiols
203(28)
Nomenclature of Alcohols
203(2)
A Word About Industrial Alcohols
205(1)
Classification of Alcohols
205(1)
Nomenclature of Phenols
206(1)
Hydrogen Bonding in Alcohols and Phenols
206(1)
Acidity and Basicity Reviewed
207(3)
The Acidity of Alcohols and Phenols
210(3)
The Basicity of Alcohols and Phenols
213(1)
Dehydration of Alcohols to Alkenes
213(2)
The Reaction of Alcohols with Hydrogen Halides
215(1)
Other Ways to Prepare Alkyl Halides from Alcohols
216(1)
A Comparison of Alcohols and Phenols
217(1)
Oxidation of Alcohols to Aldehydes, Ketones, and Carboxylic Acids
217(3)
A Word About Biologically Important Alcohols and Phenols
219(1)
Alcohols with More Than One Hydroxyl Group
220(1)
Aromatic Substitution in Phenols
221(2)
A Word About Quinones and the Bombardier Beetle
222(1)
Oxidation of Phenols
223(1)
Phenols as Antioxidants
223(1)
Thiols, the Sulfur Analogs of Alcohols and Phenols
224(7)
A Word About Hair, Curly or Straight
225(1)
Reaction Summary
226(1)
Additional Problems
227(4)
Ethers and Epoxides
231(19)
Nomenclature of Ethers
232(1)
Physical Properties of Ethers
233(1)
Ethers as Solvents
233(1)
The Grignard Reagent; an Organometallic Compound
234(3)
Preparation of Ethers
237(2)
A Closer Look at MTBE
238(1)
Cleavage of Ethers
239(2)
A Word About Ether and Anesthesia
240(1)
Epoxides (Oxiranes)
241(2)
A Word About The Gypsy Moth's Epoxide
242(1)
Reactions of Epoxides
243(1)
Cyclic Ethers
244(6)
Reaction Summary
246(1)
Additional Problems
247(3)
Aldehydes and Ketones
250(33)
Nomenclature of Aldehydes and Ketones
251(1)
Some Common Aldehydes and Ketones
252(2)
Synthesis of Aldehydes and Ketones
254(1)
Aldehydes and Ketones in Nature
255(1)
The Carbonyl Group
256(1)
Nucleophilic Addition to Carbonyl Groups: An Overview
257(1)
Addition of Alcohols: Formation of Hemiacetals and Acetals
258(4)
Addition of Water; Hydration of Aldehydes and Ketones
262(1)
Addition of Grignard Reagents and Acetylides
262(3)
Addition of Hydrogen Cyanide; Cyanohydrins
265(1)
Addition of Nitrogen Nucleophiles
266(1)
Reduction of Carbonyl Compounds
267(1)
Oxidation of Carbonyl Compounds
268(2)
Keto--Enol Tautomerism
270(1)
Acidity of α-Hydrogens; the Enolate Anion
271(1)
Deuterium Exchange in Carbonyl Compounds
272(1)
The Aldol Condensation
273(2)
The Mixed Aldol Condensation
275(1)
A Word About Water Treatment and the Chemistry of Enols/Enolates
276(1)
Commercial Syntheses via the Aldol Condensation
276(7)
Reaction Summary
277(2)
Mechanism Summary
279(1)
Additional Problems
279(4)
Carboxylic Acids and Their Derivatives
283(38)
Nomenclature of Acids
283(4)
Physical Properties of Acids
287(1)
Acidity and Acidity Constants
287(2)
What Makes Carboxylic Acids Acidic?
289(1)
Effect of Structure on Acidity; the Inductive Effect Revisited
290(1)
Conversion of Acids to Salts
291(1)
Preparation of Acids
291(5)
Oxidation of Primary Alcohols and Aldehydes
292(1)
Oxidation of Aromatic Side Chains
292(1)
Reaction of Grignard Reagents with Carbon Dioxide
293(1)
Hydrolysis of Cyanides (Nitriles)
293(2)
A Word About Green Chemistry and Ibuprofen: A Case Study
295(1)
A Closer Look At Green Chemistry
296(1)
Carboxylic Acid Derivatives
296(1)
Esters
296(1)
Preparation of Esters; Fischer Esterification
297(1)
The Mechanism of Acid-Catalyzed Esterification; Nucleophilic Acyl Substitution
298(2)
Lactones
300(1)
Saponification of Esters
300(1)
Ammonolysis of Esters
301(1)
Reaction of Esters with Grignard Reagents
302(1)
Reduction of Esters
303(1)
The Need for Activated Acyl Compounds
303(1)
Acyl Halides
304(2)
Acid Anhydrides
306(3)
A Word About Thioesters, Nature's Acyl-Activating Groups
308(1)
Amides
309(2)
A Summary of Carboxylic Acid Derivatives
311(1)
The α-Hydrogen of Esters; the Claisen Condensation
312(9)
Reaction Summary
315(1)
Mechanism Summary
316(1)
Additional Problems
316(5)
Amines and Related Nitrogen Compounds
321(27)
Classification and Structure of Amines
321(2)
Nomenclature of Amines
323(1)
Physical Properties and Intermolecular Interactions of Amines
324(1)
Preparation of Amines; Alkylation of Ammonia and Amines
325(2)
Preparation of Amines; Reduction of Nitrogen Compounds
327(2)
The Basicity of Amines
329(2)
Comparison of the Basicity and Acidity of Amines and Amides
331(2)
Reaction of Amines with Strong Acids; Amine Salts
333(2)
A Word About Alkaloids and the Dart-Poison Frogs
334(1)
Chiral Amines as Resolving Agents
335(1)
Acylation of Amines with Acid Derivatives
336(2)
Quaternary Ammonium Compounds
338(1)
Aromatic Diazonium Compounds
338(3)
Diazo Coupling; Azo Dyes
341(7)
Reaction Summary
343(1)
Mechanism Summary
344(1)
Additional Problems
344(4)
Spectroscopy and Structure Determination
348(32)
Principles of Spectroscopy
349(1)
Nuclear Magnetic Resonance Spectroscopy (NMR)
350(10)
Measuring an NMR Spectrum
351(1)
Chemical Shifts and Peak Areas
352(4)
Spin--Spin Splitting
356(4)
13C NMR Spectroscopy
360(2)
A Word About NMR in Biology and Medicine
362(1)
Infrared Spectroscopy
362(6)
Visible and Ultraviolet Spectroscopy
368(2)
Mass Spectrometry
370(10)
Additional Problems
374(6)
Heterocyclic Compounds
380(21)
Pyridine: Bonding and Basicity
380(2)
Substitution in Pyridine
382(3)
Other Six-Membered Heterocycles
385(3)
Five-Membered Heterocycles: Furan, Pyrrole, and Thiophene
388(2)
Electrophilic Substitution in Furan, Pyrrole, and Thiophene
390(1)
Other Five-Membered Heterocycles: Azoles
391(2)
A Word About Porphyrins: What Makes Blood Red and Grass Green?
392(1)
Fused-Ring Five-Membered Heterocycles: Indoles and Purines
393(8)
A Word About Morphine and Other Nitrogen-Containing Drugs
395(2)
Reaction Summary
397(1)
Mechanism Summary
398(1)
Additional Problems
398(3)
Synthetic Polymers
401(26)
Classification of Polymers
401(1)
Free-Radical Chain-Growth Polymerization
402(5)
Cationic Chain-Growth Polymerization
407(1)
Anionic Chain-Growth Polymerization
408(1)
Stereoregular Polymers; Ziegler--Natta Polymerization
409(2)
A Word About Polyacetylene and Conducting Polymers
411(1)
Diene Polymers: Natural and Synthetic Rubber
411(2)
Copolymers
413(1)
Step-Growth Polymerization: Dacron and Nylon
414(5)
A Word About Degradable Polymers
416(1)
A Word About Aramids, the Latest in Polyamides
417(1)
A Closer Look At Nylon
418(1)
Polyurethanes and Other Step-Growth Polymers
419(8)
Reaction Summary
422(1)
Mechanism Summary
423(1)
Additional Problems
424(3)
Lipids and Detergents
427(21)
Fats and Oils; Triesters of Glycerol
427(4)
Hydrogenation of Vegetable Oils
431(1)
Saponification of Fats and Oils; Soap
431(1)
How Do Soaps Work?
432(1)
Synthetic Detergents (Syndets)
433(4)
A Word About Commercial Detergents
436(1)
Phospholipids
437(1)
Prostaglandins, Leukotrienes, and Lipoxins
438(2)
A Word About Prostaglandins, Aspirin, and Pain
439(1)
Waxes
440(1)
Terpenes and Steroids
440(8)
Reaction Summary
445(1)
Additional Problems
445(3)
Carbohydrates
448(31)
Definitions and Classification
448(1)
Monosaccharides
449(1)
Chirality in Monosaccharides; Fischer Projection Formulas and D,L-Sugars
450(4)
The Cyclic Hemiacetal Structures of Monosaccharides
454(2)
Anomeric Carbons; Mutarotation
456(1)
Pyranose and Furanose Structures
457(1)
Conformations of Pyranoses
458(1)
Esters and Ethers from Monosaccharides
459(1)
Reduction of Monosaccharides
460(1)
Oxidation of Monosaccharides
460(1)
Formation of Glycosides from Monosaccharides
461(2)
Disaccharides
463(4)
Maltose
463(1)
Cellobiose
464(1)
Lactose
464(1)
Sucrose
465(1)
A Word About Sweetness and Sweeteners
466(1)
Polysaccharides
467(4)
Starch and Glycogen
467(2)
Cellulose
469(1)
A Word About Fat Substitutes from Carbohydrates
470(1)
Other Polysaccharides
471(1)
Sugar Phosphates
471(1)
Deoxy Sugars
472(1)
Amino Sugars
472(1)
Ascorbic Acid (Vitamin C)
472(7)
Reaction Summary
474(1)
Additional Problems
475(4)
Amino Acids, Peptides, and Proteins
479(36)
Naturally Occurring Amino Acids
479(4)
A Word About Amino Acid Dating
482(1)
The Acid--Base Properties of Amino Acids
483(3)
The Acid--Base Properties of Amino Acids with More Than One Acidic or Basic Group
486(1)
Electrophoresis
487(1)
Reactions of Amino Acids
488(1)
The Ninhydrin Reaction
489(1)
Peptides
489(3)
A Word About Some Naturally Occurring Peptides
491(1)
The Disulfide Bond
492(1)
Proteins
492(1)
The Primary Structure of Proteins
492(4)
Amino Acid Analysis
493(1)
Sequence Determination
494(1)
Cleavage of Selected Peptide Bonds
495(1)
The Logic of Sequence Determination
496(3)
A Word About Protein Sequencing and Evolution
498(1)
Peptide Synthesis
499(4)
Secondary Structure of Proteins
503(3)
Geometry of the Peptide Bond
503(1)
Hydrogen Bonding
504(1)
The α Helix and the Pleated Sheet
504(2)
Tertiary Structure: Fibrous and Globular Proteins
506(2)
Quaternary Protein Structure
508(7)
Reaction Summary
509(1)
Additional Problems
510(5)
Nucleotides and Nucleic Acids
515(25)
The General Structure of Nucleic Acids
515(1)
Components of Deoxyribonucleic Acid (DNA)
516(1)
Nucleosides
517(2)
Nucleotides
519(1)
The Primary Structure of DNA
520(1)
Sequencing Nucleic Acids
521(2)
A Word About DNA and Crime
522(1)
Laboratory Synthesis of Nucleic Acids
523(1)
Secondary DNA Structure; the Double Helix
523(3)
DNA Replication
526(1)
Ribonucleic Acids; RNA
527(2)
The Genetic Code and Protein Biosynthesis
529(5)
A Word About The Human Genome
531(1)
A Word About Nucleic Acids and Viruses
532(2)
Other Biologically Important Nucleotides
534(6)
Reaction Summary
537(1)
Additional Problems
537(3)
Photo Credits
540(1)
Appendix
541(3)
Table A: Bond energies for the dissociation of selected bonds in the reaction A -- X → A . + X . (in kcal/mol)
541(1)
Table B: Bond lengths of selected bonds (in angstroms, A)
541(1)
Table C: Typical acidities of organic functional groups
542(2)
Index/Glossary 544


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