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9780131498587

Essential Organic Chemistry

by
  • ISBN13:

    9780131498587

  • ISBN10:

    0131498584

  • Format: Hardcover
  • Copyright: 2010-01-01
  • Publisher: Prentice Hall
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Summary

For one-term courses in organic chemistry taken by science and pre-health professions majors This one-term organic chemistry text is designed to help students see organic chemistry as an interesting and exciting science and to give them an opportunity to develop critical thinking skills. It engages students by presenting reactions with enough detail to give them a solid understanding of reactivity, rather than requiring rote memorization. Once students understand the reasons behind the reactivity of organic compounds, they then will be better prepared to understand the reactions involved in such areas as metabolism, PCR, and genetic engineering.

Table of Contents

Preface xvi
Highlights of Essential Organic Chemistry xxii
About the Author xxvi
Electronic Structure and Covalent Bonding
1(30)
The Structure of an Atom
2(1)
The Distribution of Electrons in an Atom
3(2)
Ionic and Covalent Bonds
5(5)
Representation of Structure
10(4)
Atomic Orbitals
14(1)
Covalent Bond Formation
15(1)
Bonding in Methane and Ethane: Single Bonds
16(2)
Bonding in Ethene: A Double Bond
18(2)
Bonding in Ethyne: A Triple Bond
20(2)
Bonding in the Methyl Cation, the Methyl Radical, and the Methyl Anion
22(1)
Bonding in Water
23(1)
Bonding in Ammonia and in the Ammonium Ion
24(2)
Bonding in the Hydrogen Halides
26(1)
Summary: Orbital Hybridization, Bond Lengths, Bond Strengths, and Bond Angles
27(4)
Summary
28(1)
Problems
29(2)
Acids and Bases
31(14)
Acid--Base Reactions
31(1)
Organic Acids and Bases: pKa and pH
32(5)
The Effect of Structure on pKa
37(2)
The Effect of pH on the Structure of an Organic Compound
39(1)
Buffer Solutions
40(1)
Lewis Acids and Bases
41(4)
Summary
42(1)
Problems
43(2)
An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure
45(36)
Nomenclature of Alkyl Substituents
47(4)
Nomenclature of Alkanes
51(2)
Nomenclature of Cycloalkanes
53(2)
Nomenclature of Alkyl Halides
55(1)
Classification of Alkyl Halides, Alcohols, and Amines
56(1)
Structures of Alkyl Halides, Alcohols, Ethers, and Amines
57(2)
Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines
59(7)
Conformations of Alkanes: Rotation About Carbon--Carbon Bonds
66(2)
Cycloalkanes: Ring Strain
68(1)
Conformations of Cyclohexane
69(2)
Conformations of Monosubstituted Cyclohexanes
71(1)
Conformations of Disubstituted Cyclohexanes
72(2)
Conformations of Fused Rings
74(7)
Summary
76(1)
Problems
77(4)
Alkenes: Structure, Nomenclature, Stability, and an Introduction to Reactivity
81(22)
Molecular Formulas
82(1)
Nomenclature of Alkenes
83(2)
The Structure of Alkenes
85(1)
Cis-Trans Isomerism
86(2)
The E,Z System of Nomenclature
88(3)
The Relative Stabilities of Alkenes
91(1)
How Alkenes React • Curved Arrows
92(4)
Using a Reaction Coordinate Diagram to Describe a Reaction
96(7)
Summary
99(1)
Problems
100(3)
Reactions of Alkenes and Alkynes: An Introduction to Multistep Synthesis
103(34)
Addition of a Hydrogen Halide to an Alkene
104(1)
Carbocation Stability
105(1)
Regioselectivity of Electrophilic Addition Reactions
106(4)
Addition of Water to an Alkene
110(1)
Addition of an Alcohol to an Alkene
111(2)
Introduction to Alkynes
113(1)
Nomenclature of Alkynes
113(2)
The Structure of Alkynes
115(1)
Physical Properties of Unsaturated Hydrocarbons
116(1)
Addition of a Hydrogen Halide to an Alkyne
116(1)
Addition of Water to an Alkyne
117(2)
Addition of Hydrogen to Alkenes and Alkynes
119(2)
Acidity of a Hydrogen Bonded to an sp Hybridized Carbon
121(1)
Synthesis Using Acetylide Ions
122(1)
An Introduction to Multistep Synthesis
123(2)
Polymers
125(12)
Summary
130(1)
Summary of Reactions
131(1)
Problems
132(5)
Delocalized Electrons and Their Effect on Stability, Reactivity, and pKa: Ultraviolet and Visible Spectroscopy
137(25)
Delocalized Electrons: The Structure of Benzene
137(2)
The Bonding in Benzene
139(1)
Resonance Contributors and the Resonance Hybrid
140(1)
Drawing Resonance Contributors
141(3)
Predicted Stabilities of Responance Contributors
144(1)
Resonance Stabilization
145(1)
The Effect of Delocalized Electrons on Stability
146(2)
The Effect of Delocalized Electrons on the Nature of the Product Formed in a Reaction
148(3)
The Effect of Delocalized Electrons on pKa
151(2)
Ultraviolet and Visible Spectroscopy
153(1)
Effect of Conjugation on λmax
154(1)
The Visible Spectrum and Color
155(7)
Summary
157(1)
Summary of Reactions
158(1)
Problems
158(4)
Aromaticity • Reactions of Benzene and Substituted Benzenes
162(29)
Criteria for Aromaticity
163(1)
Aromatic Hydrocarbons
164(2)
Aromatic Heterocyclic Compounds
166(3)
Nomenclature of Monosubstituted Benzenes
169(1)
How Benzene Reacts
170(1)
General Mechanism for Electrophilic Aromatic Substitution Reactions
171(1)
Halogenation of Benzene
172(2)
Nitration of Benzene
174(1)
Sulfonation of Benzene
174(1)
Friedel--Crafts Acylation of Benzene
175(1)
Friedel--Crafts Alkylation of Benzene
175(1)
Nomenclature of Disubstituted Benzenes
176(1)
The Effect of Substituents on Reactivity
177(4)
The Effect of Substituents on Orientation
181(4)
The Effect of Substituents on pKa
185(6)
Summary
187(1)
Summary of Reactions
187(1)
Problems
188(3)
Isomers and Stereochemistry
191(25)
Cis--Trans Isomers
192(1)
Chirality
192(1)
Asymmetric Centers
193(1)
Isomers with One Asymmetric Center
194(1)
Drawing Enantiomers
195(1)
Naming Enantiomers: The R,S System of Nomenclature
195(4)
Optical Activity
199(2)
Specific Rotation
201(2)
Isomers with More than One Asymmetric Center
203(2)
Meso Compounds
205(2)
Separating Enantiomers
207(1)
Receptors
208(2)
Stereochemistry of Reactions
210(2)
Stereochemistry of Enzyme-Catalyzed Reactions
212(4)
Summary
212(1)
Problems
213(3)
Reactions of Alkanes • Radicals
216(14)
The Low Reactivity of Alkanes
217(1)
Chlorination and Bromination of Alkanes
218(2)
Factors that Determine Product Distribution
220(2)
The Reactivity--Selectivity Principle
222(2)
Stereochemistry of Radical Substitution Reactions
224(1)
Radical Reactions in Biological Systems
224(2)
Radicals and Stratospheric Ozone
226(4)
Summary
228(1)
Summary of Reactions
228(1)
Problems
228(2)
Substitution and Elimination Reactions of Alkyl Halides
230(31)
How Alkyl Halides React
231(1)
The Mechanism of an SN2 Reaction
232(3)
Factors Affecting SN2 Reactions
235(3)
The Mechanism of an SN1 Reaction
238(3)
Factors Affecting SN1 Reactions
241(1)
Comparison of the SN2 and SN1 Reactions
242(1)
Elimination Reactions of Alkyl Halides
243(2)
Products of Elimination Reactions
245(3)
Competition Between SN2/E2 and SN1/El
248(3)
Competition Between Substitution and Elimination
251(3)
Biological Methylating Reagents
254(7)
Summary
255(1)
Summary of Reactions
256(1)
Problems
257(4)
Reactions of Alcohols, Amines, Ethers, and Epoxides
261(27)
Nomenclature of Alcohols
261(2)
Substitution Reactions of Alcohols
263(2)
Elimination Reactions of Alcohols: Dehydration
265(4)
Oxidation of Alcohols
269(2)
Amines Do Not Undergo Substitution or Elimination Reactions
271(1)
Nomenclature of Ethers
272(1)
Substitution Reactions of Ethers
273(2)
Reactions of Epoxides
275(5)
Arene Oxides
280(8)
Summary
283(1)
Summary of Reactions
283(1)
Problems
284(4)
Carbonyl Compounds I: Nucleophilic Acyl Substitution
288(32)
Nomenclature
289(3)
Structures of Carboxylic Acids and Carboxylic Acid Derivatives
292(1)
Physical Properties of Carbonyl Compounds
293(1)
Naturally Occurring Carboxylic Acids and Carboxylic Acid Derivatives
294(2)
How Class I Carbonyl Compounds React
296(1)
Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives
297(2)
Reactions of Acyl Chlorides
299(2)
Reactions of Esters
301(2)
Acid-Catalyzed Ester Hydrolysis
303(4)
Reactions of Carboxylic Acids
307(2)
Reactions of Amides
309(1)
Acid-Catalyzed Hydrolysis of Amides
310(2)
Synthesis of Carboxylic Acid Derivatives
312(2)
Nitriles
314(6)
Summary
315(1)
Summary of Reactions
315(1)
Problems
316(4)
Carbonyl Compounds II: Reactions of Aldehydes and Ketones More Reactions of Carboxylic Acid Derivatives
320(24)
Nomenclature
321(2)
Relative Reactivities of Carbonyl Compounds
323(1)
How Aldehydes and Ketones React
324(1)
Reactions of Carbonyl Compounds with Grignard Reagents
324(5)
Reactions of Carbonyl Compounds with Hydride Ion
329(2)
Reactions of Aldehydes and Ketones with Amines
331(3)
Reactions of Aldehydes and Ketones with Oxygen Nucleophiles
334(3)
Nucleophilic Addition to α,β-Unsaturated Carbonyl Compounds
337(1)
Enzyme-Catalyzed Additions to α,β-Unsaturated Carbonyl Compounds
338(6)
Summary
338(1)
Summary of Reactions
339(2)
Problems
341(3)
Carbonyl Compounds III: Reactions at the α-Carbon
344(21)
Acidity of α-Hydrogens
344(3)
Keto-Enol Tautomers
347(1)
Enolization
348(1)
Alkylation of Enolate Ions
349(1)
The Aldol Addition
350(1)
Dehydration of Aldol Addition Products
351(1)
The Claisen Condensation
352(2)
Decarboxylation of 3-Oxocarboxylic Acids
354(1)
The Malonic Ester Synthesis: Synthesis of Carboxylic Acids
355(1)
The Acetoacetic Ester Synthesis: Synthesis of Methyl Ketones
356(2)
Reactions at the α-Carbon in Biological Systems
358(7)
Summary
361(1)
Summary of Reactions
361(1)
Problems
362(3)
Determining the Structures of Organic Compounds
365(42)
Spectroscopy and the Electromagnetic Spectrum
366(1)
Infrared Spectroscopy
367(2)
Characteristic Infrared Absorption Bands
369(2)
The Intensity and Shape of Absorption Bands
371(1)
C---H Absorption Bands
372(2)
Absence of Absorption Bands
374(1)
Identifying Infrared Spectra
374(2)
NMR Spectroscopy
376(1)
Shielding
377(1)
The Number of Signals in the 1H NMR Spectrum
378(1)
The Chemical Shift
379(2)
The Relative Positions of 1H NMR Signals
381(1)
Characteristic Values of Chemical Shifts
382(2)
Integration of NMR Signals
384(2)
Splitting of the Signals
386(2)
More Examples of 1H NMR Spectra
388(2)
Coupling Constants
390(2)
13C NMR Spectroscopy
392(15)
Summary
397(1)
Problems
397(10)
Carbohydrates
407(27)
Classification of Carbohydrates
408(1)
The D and L Notation
409(1)
Configurations of Aldoses
410(2)
Configurations of Ketoses
412(1)
Oxidation--Reduction Reactions of Monosaccharides
412(2)
Chain Elongation: The Kiliani--Fischer Synthesis
414(1)
Stereochemistry of Glucose: The Fischer Proof
415(2)
Cyclic Structure of Monosaccharides: Hemiacetal Formation
417(2)
Stability of Glucose
419(1)
Formation of Glycosides
420(1)
Reducing and Nonreducing Sugars
421(1)
Disaccharides
422(2)
Polysaccharides
424(3)
Some Naturally Occurring Products Derived from Carbohydrates
427(2)
Carbohydrates on Cell Surfaces
429(1)
Synthetic Sweeteners
430(4)
Summary
431(1)
Summary of Reactions
432(1)
Problems
432(2)
Amino Acids, Peptides, and Proteins
434(28)
Classification and Nomenclature of Amino Acids
435(3)
Configuration of Amino Acids
438(1)
Acid--Base Properties of Amino Acids
439(2)
The Isoelectric Point
441(1)
Separation of Amino Acids
442(2)
Peptide Bonds and Disulfide Bonds
444(4)
Protein Structure
448(1)
Determining the Primary Structure of a Peptide or a Protein
448(4)
Secondary Structure of Proteins
452(2)
Tertiary Structure of Proteins
454(2)
Quaternary Structure of Proteins
456(1)
Protein Denaturation
456(1)
Strategy of Peptide Bond Synthesis: N-Protection and C-Activation
456(6)
Summary
459(1)
Problems
459(3)
Enzymes, Coenzymes, and Vitamins
462(20)
Enzyme-Catalyzed Reactions
462(1)
Mechanism for Glucose-6-Phosphate Isomerase
463(2)
Mechanism for Aldolase
465(1)
Coenzymes and Vitamins
466(1)
Niacin: The Vitamin Needed for Many Oxidation--Reduction Reactions
467(3)
Vitamin B2
470(1)
Vitamin B1
471(1)
Vitamin H
472(2)
Vitamin B6
474(1)
Vitamin B12
475(1)
Folic Acid
476(2)
Vitamin K
478(4)
Summary
479(1)
Problems
480(2)
The Chemistry of Metabolism
482(18)
Digestion
483(1)
ATP
484(2)
Catabolism of Fats
486(2)
Catabolism of Carbohydrates
488(3)
The Fates of Pyruvate
491(1)
Catabolism of Proteins
492(2)
The Citric Acid Cycle
494(3)
Oxidative Phosphorylation
497(1)
Anabolism
497(3)
Summary
497(1)
Problems
498(2)
Lipids
500(20)
Fatty Acids
501(2)
Waxes
503(1)
Fats and Oils
503(4)
Soaps, Detergents, and Micelles
507(2)
Phospholipids
509(3)
Terpenes
512(2)
Vitamins A and D
514(1)
Steroids
515(2)
Synthetic Steroids
517(3)
Summary
518(1)
Problems
518(2)
Nucleosides, Nucleotides, and Nucleic Acids
520(21)
Nucleosides and Nucleotides
520(4)
The Nucleic Acids
524(2)
DNA is Stable---RNA is Easily Cleaved
526(1)
Biosynthesis of DNA: Replication
527(1)
DNA and Heredity
528(1)
Biosynthesis of RNA: Transcription
528(1)
RNA
529(1)
Biosynthesis of Proteins: Translation
530(3)
Why DNA Contains Thymine Instead of Uracil
533(1)
Determining the Base Sequence of DNA
534(2)
Polymerase Chain Reaction (PCR)
536(1)
Genetic Engineering
537(4)
Summary
538(1)
Problems
539(2)
The Organic Chemistry of Drugs: Discovery and Design
541
Naming Drugs
544(1)
Lead Compounds
544(1)
Molecular Modification
545(2)
Random Screening
547(2)
Serendipity in Drug Development
549(1)
Receptors
550(3)
Drug Resistance
553(1)
Molecular Modeling
554(1)
Antiviral Drugs
555(1)
Economics of Drugs • Governmental Regulations
555
Summary
556(1)
Problems
556
Appendices
1(9)
I Physical Properties of Organic Compounds
1(7)
II pKa Values
8(2)
Answers to Selected Problems 10
Glossary 1(1)
Photo Credits 1(1)
Index 1

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