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Organic Chemistry:Short Course,9780395902257
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Organic Chemistry:Short Course

by
ISBN13:

9780395902257

ISBN10:
0395902258
Format:
Hardcover
Pub. Date:
1/1/1999
Publisher(s):
Houghton Mifflin College Div
List Price: $117.96
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Table of Contents

Preface xiv
To the Student 1(5)
Bonding and Isomerism
6(35)
How Electrons Are Arranged in Atoms
6(2)
Ionic and Covalent Bonding
8(4)
Ionic Compounds
9(1)
The Covalent Bond
10(2)
Carbon and the Covalent Bond
12(1)
Carbon-Carbon Single Bonds
13(1)
Polar Covalent Bonds
14(2)
Multiple Covalent Bonds
16(1)
Valence
17(1)
Isomerism
18(1)
Writing Structural Formulas
19(2)
Abbreviated Structural Formulas
21(2)
Formal Charge
23(1)
Resonance
24(2)
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(2)
Acyclic Compounds
32(1)
Carbocyclic Compounds
33(1)
Heterocyclic Compounds
33(1)
Classification According to Functional Group
34(7)
Additional Problems
37(4)
Alkanes and Cycloalkanes; Conformational and Geometric Isomerism
41(30)
The Structures of Alkanes
42(2)
Nomenclature of Organic Compounds
44(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(2)
A Word About: Isomers, Possible and Impossible
50(1)
Physical Properties of Alkanes and Nonbonding Intermolecular Interactions
51(2)
Conformations of Alkanes
53(1)
Cycloalkane Nomenclature and Conformation
54(5)
Cis--trans Isomerism in Cycloalkanes
59(1)
Summary of Isomerism
60(1)
Reactions of Alkanes
61(3)
Oxidation and Combustion; Alkanes as Fuels
61(1)
Halogenation of Alkanes
62(2)
The Free-Radical Chain Mechanism of Halogenation
64(7)
A Word About: Methane, Marsh Gas, and Miller's Experiment
64(3)
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
77(2)
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
82(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(1)
Cycloaddition to Conjugated Dienes: The Diels--Alder Reaction
97(2)
Free-Radical Additions; Polyethylene
99(1)
Oxidation of Alkenes
100(4)
Oxidation with Permanganate; a Chemical Test
100(1)
Ozonolysis of Alkenes
101(2)
Other Alkene Oxidations
103
A Word About: Ethylene: Raw Material and Plant Hormone
102(2)
Some Facts About Triple Bonds
104(1)
The Orbital Model of a Triple Bond
104(1)
Addition Reactions of Alkynes
105(1)
Acidity of Alkynes
106(10)
A Word About: Petroleum, Gasoline, and Octane Number
108(2)
Reaction Summary
110(2)
Mechanism Summary
112(1)
Additional Problems
112(4)
Aromatic Compounds
116(29)
Some Facts About Benzene
117(1)
The Kekule Structure of Benzene
118(1)
The Resonance Model for Benzene
119(1)
Orbital Model for Benzene
119(1)
Symbols for Benzene
120(1)
Nomenclature of Aromatic Compounds
121(2)
The Resonance Energy of Benzene
123(1)
Electrophilic Substitution
124(1)
The Mechanism of Electrophilic Aromatic Substitution
125(4)
Halogenation
127(1)
Nitration
127(1)
Sulfonation
128(1)
Alkylation and Acylation
128(1)
Ring-Activating and Ring-Deactivating Substituents
129(1)
Ortho, Para-Directing, and Meta-Directing Groups
130(4)
Ortho, Para-Directing Groups
130(3)
Meta-Directing Groups
133(1)
Substituent Effects on Reactivity
134(1)
The Importance of Directing Effects in Synthesis
134(1)
Polycyclic Aromatic Hydrocarbons
135(10)
A Word About: Polycyclic Aromatic Hydrocarbons and Cancer
136(2)
A Word About: C60, an Aromatic Sphere: The Fullerenes
138(2)
Reaction Summary
140(1)
Mechanism Summary
141(1)
Additional Problems
141(4)
Stereoisomerism
145(34)
Chirality and Enantiomers
145(2)
Stereogenic Centers; the Stereogenic Carbon Atom
147(5)
Configuration and the R--S Convention
152(4)
The E--Z Convention for Cis--Trans Isomers
156(1)
Polarized Light and Optical Activity
157(5)
A Word About: Pasteur's Experiments and the van't Hoff--LeBel Explanation
160(2)
Properties of Enantiomers
162(1)
Fischer Projection Formulas
163(1)
Compounds with More Than One Stereogenic Center; Diastereomers
164(2)
Meso Compounds; the Stereoisomers of Tartaric Acid
166(2)
Stereochemistry: A Recap of Definitions
168(2)
Stereochemistry and Chemical Reactions
170(1)
Resolution of a Racemic Mixture
171(8)
A Word About: Enantiomers and Biological Activity
172(1)
Additional Problems
173(6)
Organic Halogen Compounds; Substitution and Elimination Reactions
179(25)
Nucleophilic Substitution
180(1)
Examples of Nucleophilic Substitutions
180(4)
Nucleophilic Substitution Mechanisms
184(1)
The SN2 Mechanism
185(3)
The SN1 Mechanism
188(2)
The SN1 and SN2 Mechanisms Compared
190(2)
Dehydrohalogenation, an Elimination Reaction; the E2 and E1 Mechanisms
192(1)
Substitution and Elimination in Competition
193(3)
Tertiary Halides
193(1)
Primary Halides
194(1)
Secondary Halides
194(2)
A Word About: CFCs, the Ozone Layer, and Trade-offs
196(1)
Polyhalogenated Aliphatic Compounds
196(8)
A Word About: Insecticides and Herbicides
198(2)
Reaction Summary
200(1)
Mechanism Summary
200(1)
Additional Problems
201(3)
Alcohols, Phenols, and Thiols
204(27)
Nomenclature of Alcohols
204(1)
Classification of Alcohols
205(1)
Nomenclature of Phenols
206(1)
Hydrogen Bonding in Alcohols and Phenols
206(2)
Acidity and Basicity Reviewed
208(2)
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(2)
Alcohols with More Than One Hydroxyl Group
219(1)
Aromatic Substitution in Phenols
219(2)
A Word About: Industrial Alcohols
220(1)
Oxidation of Phenols
221(3)
A Word About: Biologically Important Alcohols and Phenols
222(2)
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(18)
Nomenclature of Ethers
231(1)
Physical Properties of Ethers
232(1)
Ethers as Solvents
233(1)
The Grignard Reagent; an Organometallic Compound
234(2)
Preparation of Ethers
236(2)
Cleavage of Ethers
238(2)
A Word About: Ether and Anesthesia
239(1)
Epoxides (Oxiranes)
240(2)
A Word About: The Gypsy Moth's Epoxide
240(2)
Reactions of Epoxides
242(1)
Cyclic Ethers
243(6)
Reaction Summary
245(1)
Additional Problems
246(3)
Aldehydes and Ketones
249(34)
Nomenclature of Aldehydes and Ketones
250(1)
Some Common Aldehydes and Ketones
251(1)
Synthesis of Aldehydes and Ketones
252(2)
A Word About: Quinones and the Bombardier Beetle
253(1)
Aldehydes and Ketones in Nature
254(1)
The Carbonyl Group
254(2)
Nucleophilic Addition to Carbonyl Groups: An Overview
256(2)
Addition of Alcohols: Formation of Hemiacetals and Acetals
258(3)
Addition of Water; Hydration of Aldehydes and Ketones
261(1)
Addition of Grignard Reagents and Acetylides
262(2)
Addition of Hydrogen Cyanide; Cyanohydrins
264(1)
Addition of Nitrogen Nucleophiles
265(1)
Reduction of Carbonyl Compounds
266(1)
Oxidation of Carbonyl Compounds
267(2)
Keto--Enol Tautomerism
269(2)
A Word About: Tautomerism and Photochromism
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)
Commercial Syntheses via the Aldol Condensation
275(8)
Reaction Summary
276(2)
Mechanism Summary
278(1)
Additional Problems
278(5)
Carboxylic Acids and Their Derivatives
283(36)
Nomenclature of Acids
283(4)
Physical Properties of Acids
287(1)
Acidity and Acidity Constants
288(1)
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
292(2)
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(1)
Carboxylic Acid Derivatives
294(1)
Esters
295(1)
Preparation of Esters; Fischer Esterification
296(1)
The Mechanism of Acid-Catalyzed Esterification; Nucleophilic Acyl Substitution
296(2)
Lactones
298(1)
Saponification of Esters
299(1)
Ammonolysis of Esters
300(1)
Reaction of Esters with Grignard Reagents
300(1)
Reduction of Esters
301(1)
The Need for Activated Acyl Compounds
301(1)
Acyl Halides
302(2)
Acid Anhydrides
304(3)
A Word About: Thioesters, Nature's Acyl-Activating Groups
306(1)
Amides
307(2)
A Word About: Urea
309(1)
A Summary of Carboxylic Acid Derivatives
309(2)
The α-Hydrogen of Esters; the Claisen Condensation
311(8)
Reaction Summary
313(2)
Mechanism Summary
315(1)
Additional Problems
315(4)
Amines and Related Nitrogen Compounds
319(29)
Classification and Structure of Amines
319(1)
Nomenclature of Amines
320(2)
Physical Properties and Intermolecular Interactions of Amines
322(1)
Preparation of Amines; Alkylation of Ammonia and Amines
323(2)
Preparation of Amines; Reduction of Nitrogen Compounds
325(2)
The Basicity of Amines
327(2)
Comparison of the Basicity and Acidity of Amines and Amides
329(1)
Reaction of Amines with Strong Acids; Amine Salts
330(3)
A Word About: Alkaloids and the Dart-Poison Frogs
332(1)
Chiral Amines as Resolving Agents
333(1)
Acylation of Amines with Acid Derivatives
334(2)
Quaternary Ammonium Compounds
336(1)
Aromatic Diazonium Compounds
336(3)
Diazo Coupling; Azo Dyes
339(9)
Reaction Summary
341(2)
Mechanism Summary
343(1)
Additional Problems
343(5)
Spectroscopy and Structure Determination
348(34)
Principles of Spectroscopy
349(1)
Nuclear Magnetic Resonance Spectroscopy (NMR)
350(11)
Measuring an NMR Spectrum
352(1)
Chemical Shifts and Peak Areas
352(5)
Spin--Spin Splitting
357(4)
C NMR Spectroscopy
361(3)
A Word About: NMR in Biology and Medicine
362(2)
Infrared Spectroscopy
364(5)
Visible and Ultraviolet Spectroscopy
369(2)
Mass Spectrometry
371(11)
Additional Problems
375(7)
Heterocyclic Compounds
382(22)
Pyridine: Bonding and Basicity
382(2)
Substitution in Pyridine
384(3)
Other Six-Membered Heterocycles
387(2)
Five-Membered Heterocycles: Furan, Pyrrole, and Thiophene
389(3)
Electrophilic Substitution in Furan, Pyrrole, and Thiophene
392(1)
Other Five-Membered Heterocycles: Azoles
393(3)
A Word About: Porphyrins: What Makes Blood Red and Grass Green?
394(2)
Fused-Ring Five-Membered Heterocycles: Indoles and Purines
396(8)
A Word About: Morphine and Other Nitrogen-Containing Drugs
398(2)
Reaction Summary
400(1)
Mechanism Summary
401(1)
Additional Problems
402(2)
Synthetic Polymers
404(25)
Classification of Polymers
404(1)
Free-Radical Chain-Growth Polymerization
405(6)
Cationic Chain-Growth Polymerization
411(1)
Anionic Chain-Growth Polymerization
412(1)
Stereoregular Polymers; Ziegler--Natta Polymerization
412(2)
Diene Polymers: Natural and Synthetic Rubber
414(2)
Copolymers
416(1)
Step-Growth Polymerization: Dacron and Nylon
417(3)
A Word About: Degradable Polymers
419(1)
Polyurethanes and Other Step-Growth Polymers
420(9)
A Word About: Aramids, the Latest in Polyamides
421(3)
Reaction Summary
424(1)
Mechanism Summary
425(1)
Additional Problems
426(3)
Lipids and Detergents
429(22)
Fats and Oils; Triesters of Glycerol
429(4)
Hydrogenation of Vegetable Oils
433(1)
Saponification of Fats and Oils; Soap
433(1)
How Do Soaps Work?
434(2)
Synthetic Detergents (Syndets)
436(4)
A Word About: Commercial Detergents
439(1)
Phospholipids
440(1)
Prostaglandins, Leukotrienes, and Lipoxins
440(1)
Waxes
441(1)
A Word About: Prostaglandins, Aspirin, and Pain
442(1)
Terpenes and Steroids
442(9)
Reaction Summary
447(1)
Additional Problems
448(3)
Carbohydrates
451(31)
Definitions and Classification
451(1)
Monosaccharides
452(1)
Chirality in Monosaccharides; Fischer Projection Formulas and D,L-Sugars
453(4)
The Cyclic Hemiacetal Structures of Monosaccharides
457(2)
Anomeric Carbons; Mutarotation
459(1)
Pyranose and Furanose Structures
460(1)
Conformations of Pyranoses
461(1)
Esters and Ethers from Monosaccharides
462(1)
Reduction of Monosaccharides
463(1)
Oxidation of Monosaccharides
463(1)
Formation of Glycosides from Monosaccharides
464(2)
Disaccharides
466(4)
Maltose
466(1)
Cellobiose
467(1)
Lactose
467(1)
Sucrose
468(1)
A Word About: Sweetness and Sweeteners
468(2)
Polysaccharides
470(5)
Starch and Glycogen
470(2)
Cellulose
472(1)
Other Polysaccharides
473(1)
A Word About: Fat Substitutes from Carbohydrates
474(1)
Sugar Phosphates
475(1)
Deoxy Sugars
475(1)
Amino Sugars
475(1)
Ascorbic Acid (Vitamin C)
476(6)
Reaction Summary
477(1)
Additional Problems
478(4)
Amino Acids, Peptides, and Proteins
482(37)
Naturally Occurring Amino Acids
482(4)
A Word About: Amino Acid Dating
485(1)
The Acid--Base Properties of Amino Acids
486(3)
The Acid--Base Properties of Amino Acids with More Than One Acidic or Basic Group
489(2)
Electrophoresis
491(1)
Reactions of Amino Acids
491(1)
The Ninhydrin Reaction
492(1)
Peptides
492(2)
A Word About: Some Naturally Occurring Peptides
494(1)
The Disulfide Bond
494(2)
Proteins
496(1)
The Primary Structure of Proteins
496(4)
Amino Acid Analysis
496(1)
Sequence Determination
497(1)
Cleavage of Selected Peptide Bonds
498(2)
The Logic of Sequence Determination
500(2)
Peptide Synthesis
502(5)
A Word About: Protein Sequencing and Evolution
503(4)
Secondary Structure of Proteins
507(4)
Geometry of the Peptide Bond
507(1)
Hydrogen Bonding
508(1)
The α Helix and the Pleated Sheet
508(3)
Tertiary Structure: Fibrous and Globular Proteins
511(2)
Quaternary Protein Structure
513(6)
Reaction Summary
513(1)
Additional Problems
514(5)
Nucleotides and Nucleic Acids
519(26)
The General Structure of Nucleic Acids
519(1)
Components of Deoxyribonucleic Acid (DNA)
520(1)
Nucleosides
521(1)
Nucleotides
522(2)
The Primary Structure of DNA
524(1)
Sequencing Nucleic Acids
525(2)
A Word About: DNA and Crime
526(1)
Laboratory Synthesis of Nucleic Acids
527(1)
Secondary DNA Structure; the Double Helix
528(2)
DNA Replication
530(2)
Ribonucleic Acids; RNA
532(1)
The Genetic Code and Protein Biosynthesis
533(3)
Other Biologically Important Nucleotides
536(9)
A Word About: Nucleic Acids and Viruses
538(3)
Reaction Summary
541(1)
Additional Problems
541(3)
Photo Credits
544(1)
Appendix 545(3)
Table A: Bond energies for the dissociation of selected bonds in the reaction A---X→A · + X · (in kcal/mol)
545(1)
Table B: Bond lengths of selected bonds (in angstroms, A)
545(1)
Table C: Acidities of Organic Functional Groups
546(2)
Index/Glossary 548


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