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Organic Chemistry

by
Edition:
6th
ISBN13:

9780131963160

ISBN10:
0131963163
Format:
Hardcover
Pub. Date:
1/1/2011
Publisher(s):
Prentice Hall
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Summary

This innovative book from acclaimed educator Paula Bruice is organized in a way that discourages rote memorization. The authorrs"s writing has been praised for anticipating readers'questions, and appeals to their need to learn visually and by solving problems. Emphasizing that learners should reason their way to solutions rather than memorize facts, Bruice encourages them to think about what they have learned previously and apply that knowledge in a new setting.KEY TOPICSThe book balances coverage of traditional topics with bioorganic chemistry, highlights mechanistic similarities, and ties synthesis and reactivity together-teaching the reactivity of a functional group and the synthesis of compounds obtained as a result of that reactivity.For the study of organic chemistry.

Table of Contents

Preface xxi
For the Student xxix
About the Author xxxviii
Part 1 An Introduction to the Study of Organic Chemistry
1(122)
Electronic Structure and Bonding · Acids and Bases
2(69)
The Structure of an Atom
4(1)
How the Electrons in an Atom Are Distributed
5(3)
Ionic and Covalent Bonds
8(7)
How the Structure of a Compound Is Represented
15(6)
Atomic Orbitals
21(1)
An Introduction to Molecular Orbital Theory
22(6)
How Single Bonds Are Formed in Organic Compounds
28(4)
How a Double Bond Is Formed: The Bonds in Ethene
32(2)
How a Triple Bond Is Formed: The Bonds in Ethyne
34(1)
The Bonds in the Methyl Cation, the Methyl Radical, and the Methyl Anion
35(2)
The Bonds in Water
37(1)
The Bonds in Ammonia and in the Ammonium Ion
38(1)
The Bonds in the Hydrogen Halides
39(1)
Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles
40(3)
The Dipole Moments of Molecules
43(1)
An Introduction to Acids and Bases
44(1)
pKa and pH
45(2)
Organic Acids and Bases
47(3)
How to Predict the Outcome of an Acid-Base Reaction
50(1)
How the Structure of an Acid Affects Its Acidity
51(4)
How Substituents Affect the Strength of an Acid
55(2)
An Introduction to Delocalized Electrons
57(1)
A Summary of the Factors That Determine Acid Strength
58(2)
How the pH Affects the Structure of an Organic Compound
60(3)
Buffer Solutions
63(1)
The Second Definition of Acid and Base: Lewis Acids and Bases
64(7)
Summary
65(1)
Key Terms
66(1)
Problems
67
Problem-Solving Strategy
61
Box Features: Natural Versus Synthetic
3(3)
Albert Einstein
6(1)
Max Karl Ernst Ludwig Planck
7(26)
Diamond, Graphite, and Buckminsterfullerene: Substances Containing Only Carbon Atoms
33(5)
Water---A Unique Compound
38(8)
Acid Rain
46(14)
Derivation of the Henderson-Hasselbalch Equation
60(4)
Blood: A Buffered Solution
64(7)
An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure
71(52)
How Alkyl Substituents Are Named
74(4)
The Nomenclature of Alkanes
78(4)
Nomenclature of Cycloalkanes · Skeletal Structures
82(3)
Nomenclature of Alkyl Halides
85(1)
Nomenclature of Ethers
86(1)
Nomenclature of Alcohols
87(2)
Nomenclature of Amines
89(3)
The Structures of Alkyl Halides, Alcohols, Ethers, and Amines
92(2)
The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines
94(7)
Rotation Occurs About Carbon-Carbon Bonds
101(3)
Some Cycloalkanes Have Ring Strain
104(3)
Conformations of Cyclohexane
107(3)
Conformers of Monosubstituted Cyclohexanes
110(3)
Conformers of Disubstituted Cyclohexanes
113(10)
Summary
117(1)
Key Terms
117(1)
Problems
118
Problem-Solving Strategy
113
Box Features: Bad Smelling Compounds
90(15)
Highly Strained Hydrocarbons
105(1)
von Baeyer and Barbituric Acid
106(17)
Part 2 Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization
123(220)
Alkenes: Structure, Nomenclature, and an Introduction to Reactivity · Thermodynamics and Kinetics
124(35)
Molecular Formulas and the Degree of Unsaturation
125(1)
The Nomenclature of Alkenes
126(3)
The Structures of Alkenes
129(1)
Alkenes Can Have Cis and Trans Isomers
130(3)
Naming Alkenes Using the E, Z System
133(4)
How Alkenes React · Curved Arrows Show the Flow of Electrons
137(4)
Thermodynamics and Kinetics
141(11)
Using a Reaction Coordinate Diagram to Describe a Reaction
152(7)
Summary
154(1)
Key Terms
155(1)
Problems
155
Problem-Solving Strategy
136
Box Features: Cis-Trans Interconversion in Vision
132(8)
A Few Words About Curved Arrows
140(11)
The Difference Between ΔG†a and Ea
151(8)
The Reactions of Alkenes
159(41)
Addition of a Hydrogen Halide to an Alkene
160(1)
Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon
161(3)
The Structure of the Transition State Lies Partway Between the Structures of the Reactants and Products
164(2)
Electrophilic Addition Reactions Are Regioselective
166(3)
Acid-Catalyzed Addition Reactions
169(3)
A Carbocation Will Rearrange If It Can Form a More Stable Carbocation
172(3)
Addition of a Halogen to an Alkene
175(5)
Oxymercuration-Reduction and Alkoxymercuration-Reduction Are Other Ways to Add Water or an Alcohol to an Alkene
180(2)
Addition of a Peroxyacid to an Alkene
182(2)
Addition of Borane to an Alkene: Hydroboration-Oxidation
184(4)
Addition of Hydrogen to an Alkene · The Relative Stabilities of Alkenes
188(4)
Reactions and Synthesis
192(8)
Summary
194(1)
Summary of Reactions
194(2)
Key Terms
196(1)
Problems
196
Problem-Solving Strategy
190
Box Features: Borane and Diborane
185(5)
Trans Fats
190(3)
Pesticides: Natural and Synthetic
193(7)
Stereochemistry: The Arrangement of Atoms in Space; The Stereochemistry of Addition Reactions
200(58)
Cis-Trans Isomers Result from Restricted Rotation
201(1)
A Chiral Object Has a Nonsuperimposable Mirror Image
202(1)
An Asymmetric Center Is a Cause of Chirality in a Molecule
203(1)
Isomers with One Asymmetric Center
204(1)
Asymmetric Centers and Stereocenters
205(1)
How to Draw Enantiomers
205(1)
Naming Enantiomers by the R, S System
206(6)
Chiral Compounds Are Optically Active
212(1)
How Specific Rotation Is Measured
213(2)
Enantiomeric Excess
215(1)
Isomers with More than One Asymmetric Center
216(5)
Meso Compounds Have Asymmetric Centers but Are Optically Inactive
221(4)
How to Name Isomers with More than One Asymmetric Center
225(4)
Reactions of Compounds That Contain an Asymmetric Center
229(1)
The Absolute Configuration of (+)-Glyceraldehyde
230(2)
How Enantiomers Can Be Separated
232(1)
Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers
233(1)
Stereochemistry of Reactions: Regioselective, Stereoselective, and Stereospecific Reactions
234(1)
The Stereochemistry of Electrophilic Addition Reactions of Alkenes
235(11)
The Stereochemistry of Enzyme-Catalyzed Reactions
246(1)
Enantiomers Can Be Distinguished by Biological Molecules
247(11)
Summary
250(1)
Key Terms
251(1)
Problems
251
Problem-Solving Strategy
244
Box Features: Cyclic Alkenes
239(10)
The Enantiomers of Thalidomide
249(1)
Chiral Drugs
250(8)
The Reactions of Alkynes: An Introduction to Multistep Synthesis
258(29)
The Nomenclature of Alkynes
260(1)
How to Name a Compound That Has More than One Functional Group
261(2)
The Physical Properties of Unsaturated Hydrocarbons
263(1)
The Structure of Alkynes
264(1)
How Alkynes React
264(2)
Addition of Hydrogen Halides and Addition of Halogens to an Alkyne
266(3)
Addition of Water to an Alkyne
269(2)
Addition of Borane to an Alkyne: Hydroboration-Oxidation
271(1)
Addition of Hydrogen to an Alkyne
272(2)
A Hydrogen Bonded to an sp Carbon Is ``Acidic''
274(2)
Synthesis Using Acetylide Ions
276(1)
Designing a Synthesis I: An Introduction to Multistep Synthesis
277(10)
Summary
282(1)
Summary of Reactions
282(1)
Key Terms
283(1)
Problems
284
Problem-Solving Strategy
275
Box Features: Ethyne Chemistry or the Forward Pass?
259(4)
How a Banana Slug Knows What to Eat
263(12)
Sodium Amide and Sodium
275(6)
Identifying Compounds
281(6)
Delocalized Electrons and Their Effect on Stability, Reactivity, and pKa · More About Molecular Orbital Theory
287(56)
Benzene Has Delocalized Electrons
288(3)
The Bonding in Benzene
291(1)
Resonance Contributors and the Resonance Hybrid
291(2)
How to Draw Resonance Contributors
293(3)
The Predicted Stabilities of Resonance Contributors
296(2)
Delocalization Energy Is the Additional Stability Delocalized Electrons Give to a Compound
298(3)
Examples Illustrating the Effect of Delocalized Electrons on Stability
301(4)
A Molecular Orbital Description of Stability
305(7)
How Delocalized Electrons Affect pKa
312(4)
Delocalized Electrons Can Affect the Product of a Reaction
316(5)
Thermodynamic Versus Kinetic Control of Reactions
321(5)
The Diels-Alder Reaction Is a 1,4-Addition Reaction
326(17)
Summary
335(1)
Summary of Reactions
336(1)
Key Terms
336(1)
Problems
337
Problem-Solving Strategy
334
Box Features: Kekule's Dream
290(5)
Peptide Bonds
295(48)
Part 3 Substitution and Elimination Reactions
343(168)
Substitution Reactions of Alkyl Halides
344(45)
How Alkyl Halides React
346(1)
The Mechanism of an SN2 Reaction
346(6)
Factors That Affect SN2 Reactions
352(5)
The Reversibility of an SN2 Reaction Depends on the Basicities of the Leaving Groups in the Forward and Reverse Directions
357(4)
The Mechanism of an SN2 Reaction
361(3)
Factors That Affect SN1 Reactions
364(2)
More About the Stereochemistry of SN2 and SN1 Reactions
366(2)
Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides
368(3)
Competition Between SN2 and SN1 Reactions
371(4)
The Role of the Solvent in SN2 and SN1 Reactions
375(6)
Intermolecular Versus Intramolecular Reactions
381(1)
Biological Methylating Reagents Have Good Leaving Groups
382(7)
Summary
384(1)
Summary of Reactions
385(1)
Key Terms
385(1)
Problems
385
Problem-Solving Strategy
373
Box Features: Survival Compounds
345(16)
Why Carbon Instead of Silicon?
361(15)
Solvation Effects
376(3)
Environmental Adaptation
379(4)
Eradicating Termites
383(1)
S-Adenosylmethionine: A Natural Antidepressant
384(5)
Elimination Reactions of Alkyl Halides · Competition Between Substitution and Elimination
389(40)
The E2 Reaction
390(1)
An E2 Reaction Is Regioselective
391(7)
The E1 Reaction
398(4)
Competition Between E2 and E1 Reactions
402(1)
E2 and E1 Reactions Are Stereoselective
403(5)
Elimination from Substituted Cyclohexanes
408(4)
A Kinetic Isotope Effect Can Help Determine a Mechanism
412(1)
Competition Between Substitution and Elimination
413(5)
Substitution and Elimination Reactions in Synthesis
418(2)
Consecutive E2 Elimination Reactions
420(1)
Designing a Synthesis II: Approaching the Problem
421(8)
Summary
423(1)
Summary of Reactions
424(1)
Key Terms
425(1)
Problems
425
Problem-Solving Strategy
401
Box Feature: Investigating Naturally Occurring Organohalides
390(39)
Reactions of Alcohols, Amines, Ethers, Epoxides, and Sulfur-Containing Compounds · Organometallic Compounds
429(52)
Nucleophilic Substitution Reactions of Alcohols: Forming Alkyl Halides
430(4)
Other Methods for Converting Alcohols into Alkyl Halides
434(1)
Converting Alcohols into Sulfonate Esters
435(3)
Elimination Reactions of Alcohols: Dehydration
438(7)
Oxidation of Alcohols
445(2)
Amines Do Not Undergo Substitution or Elimination Reactions but Are the Most Common Organic Bases
447(2)
Nucleophilic Substitution Reactions of Ethers
449(3)
Nucleophilic Substitution Reactions of Epoxides
452(3)
Arene Oxides
455(5)
Crown Ethers
460(2)
Thiols, Sulfides, and Sulfonium Salts
462(3)
Organometallic Compounds
465(4)
Coupling Reactions
469(12)
Summary
472(1)
Summary of Reactions
473(3)
Key Terms
476(1)
Problems
476
Problem-Solving Strategy
443
Box Feature: The Lucas Test
432(2)
Grain Alcohol and Wood Alcohol
434(9)
Biological Dehydrations
443(4)
Blood Alcohol Content
447(1)
Alkaloids
448(3)
Anesthetics
451(8)
Benzo[a]pyrene and Cancer
459(1)
Chimney Sweeps and Cancer
460(2)
An Ionophorous Antibiotic
462(2)
Mustard---A Chemical Warfare Agent
464(1)
Antidote to a Chemical Warfare Agent
464(17)
Radicals · Reactions of Alkanes
481(30)
Alkanes Are Unreactive Compounds
483(1)
Chlorination and Bromination of Alkanes
483(2)
Radical Stability Depends on the Number of Alkyl Groups Attached to the Carbon with the Unpaired Electron
485(1)
The Distribution of Products Depends on Probability and Reactivity
486(3)
The Reactivity-Selectivity Principle
489(4)
Addition of Radicals to an Alkene
493(3)
Stereochemistry of Radical Substitution and Addition Reactions
496(1)
Radical Substitution of Benzylic and Allylic Hydrogens
497(3)
Designing a Synthesis III: More Practice with Multistep Synthesis
500(2)
Radical Reactions Occur in Biological Systems
502(3)
Radicals and Stratospheric Ozone
505(6)
Summary
506(1)
Summary of Reactions
507(1)
Key Terms
508(1)
Problems
508
Problem-Solving Strategy
491
Box Feature: Octane Number
482(1)
Fossil Fuels: A Problematic Energy Source
482(18)
Cyclopropane
500(3)
Decaffeinated Coffee and the Cancer Scare
503(1)
Food Preservatives
504(2)
Artificial Blood
506(5)
Part 4 Identification of Organic Compounds
511(128)
Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet/Visible Spectroscopy
512(57)
Mass Spectrometry
513(2)
The Mass Spectrum · Fragmentation
515(3)
Isotopes in Mass Spectrometry
518(2)
High-Resolution Mass Spectrometry Can Reveal Molecular Formulas
520(1)
Fragmentation Patterns of Functional Groups
520(8)
Spectroscopy and the Electromagnetic Spectrum
528(2)
Infrared Spectroscopy
530(3)
Characteristic Infrared Absorption Bands
533(1)
The Intensity of Absorption Bands
534(1)
The Position of Absorption Bands
535(1)
The Position of an Absorption Band Is Affected by Electron Delocalization, Electron Donation and Withdrawal, and Hydrogen Bonding
536(8)
The Shape of Absorption Bands
544(1)
The Absence of Absorption Bands
544(1)
Some Vibrations Are Infrared Inactive
545(1)
A Lesson in Interpreting Infrared Spectra
546(3)
Ultraviolet and Visible Spectroscopy
549(2)
The Beer-Lambert Law
551(1)
The Effect of Conjugation on λmax
552(2)
The Visible Spectrum and Color
554(1)
Some Uses of UV/Vis Spectroscopy
555(14)
Summary
557(1)
Key Terms
558(1)
Problems
559
Problem-Solving Strategy
539
Box Features: Mass Spectrometry in Forensics
526(9)
The Originator of Hooke's Law
535(16)
Ultraviolet Light and Sunscreens
551(4)
Anthocyanins: A Colorful Class of Compounds
555(14)
NMR Spectroscopy
569(70)
An Introduction to NMR Spectroscopy
569(3)
Fourier Transform NMR
572(1)
Shielding Causes Different Hydrogens to Show Signals at Different Frequencies
573(1)
The Number of Signals in an 1H NMR Spectrum
574(3)
The Chemical Shift Tells How Far the Signal Is from the Reference Signal
577(1)
The Relative Positions of 1H NMR Signals
578(1)
Characteristic Values of Chemical Shifts
579(3)
Diamagnetic Anisotropy
582(2)
The Integration of NMR Signals Reveals the Relative Number of Protons Causing the Signal
584(2)
Splitting of the Signals Is Desribed by the N + 1 Rule
586(5)
More Examples of 1H NMR Spectra
591(6)
Coupling Constants Identify Coupled Protons
597(3)
Splitting Diagrams Explain the Multiplicity of a Signal
600(3)
Diastereotopic Hydrogens Are Not Chemically Equivalent
603(1)
The Time Dependence of NMR Spectroscopy
604(1)
Protons Bonded to Oxygen and Nitrogen
605(2)
The Use of Deuterium in 1H NMR Spectroscopy
607(1)
The Resolution of 1H NMR Spectra
608(2)
13C NMR Spectroscopy
610(6)
DEPT 13C NMR Spectra
616(1)
Two-Dimensional NMR Spectroscopy
616(3)
NMR Used in Medicine Is Called Magnetic Resonance Imaging
619(20)
Summary
620(1)
Key Terms
621(1)
Problems
621
Problem-Solving Strategy
614
Box Feature: Nikola Tesla (1856-1943)
572(67)
Part 5 Aromatic Compounds
639(82)
Aromaticit · Reactions of Benzene
640(37)
Aromatic Compounds Are Unusually Stable
640(2)
The Two Criteria for Aromaticity
642(1)
Applying the Criteria for Aromaticity
643(3)
Aromatic Heterocyclic Compounds
646(1)
Some Chemical Consequences of Aromaticity
647(2)
Antiaromaticity
649(1)
A Molecular Orbital Description of Aromaticity and Antiaromaticity
650(1)
Nomenclature of Monosubstituted Benzenes
651(2)
How Benzene Reacts
653(1)
The General Mechanism for Electrophilic Aromatic Substitution Reactions
654(1)
Halogenation of Benzene
655(2)
Nitration of Benzene
657(1)
Sulfonation of Benzene
658(2)
Friedel-Crafts Acylation of Benzene
660(1)
Friedel-Crafts Alkylation of Benzene
661(3)
Alkylation of Benzene by Acylation-Reduction
664(1)
Using Coupling Reactions to Alkylate Benzene
665(1)
It Is Important to Have More Than One Way to Carry Out a Reaction
665(1)
How Some Substituents on a Benzene Ring Can Be Chemically Changed
666(11)
Summary
670(1)
Summary of Reactions
671(2)
Key Terms
673(1)
Problems
673
Problem-Solving Strategy
649
Box Feature: Buckyballs and AIDS
644(8)
The Toxicity of Benzene
652(5)
Thyroxine
657(6)
Incipient Primary Carbocations
663(14)
Reactions of Substituted Benzenes
677(44)
Nomenclature of Disubstituted and Polysubstituted Benzenes
678(3)
Some Substituents Increase the Reactivity of a Benzene Ring and Some Decrease Its Reactivity
681(6)
The Effect of Substituents on Orientation
687(4)
The Effect of Substituents on pKa
691(2)
The Ortho-Para Ratio
693(1)
Additional Considerations Regarding Substituent Effects
694(2)
Designing a Synthesis IV: Synthesis of Monosubstituted and Disubstituted Benzenes
696(2)
Synthesis of Trisubstituted Benzenes
698(1)
Synthesis of Substituted Benzenes Using Arenediazonium Salts
699(4)
The Arenediazonium Ion as an Electrophile
703(1)
The Mechanism for the Reaction of Amines with Nitrous Acid
704(3)
Nucleophilic Aromatic Substitution: An Addition-Elimination Mechanism
707(2)
Nucleophilic Aromatic Substitution: An Elimination-Addition Mechanism That Forms a Benzyne Intermediate
709(2)
Polycyclic Benzenoid Hydrocarbons
711(10)
Summary
711(1)
Summary of Reactions
712(2)
Key Terms
714(1)
Problems
714
Problem-Solving Strategy
693
Box Features: Measuring Toxicity
679(27)
Nitrosamines and Cancer
706(15)
Part 6 Carbonyl Compounds
721(186)
Carbonyl Compounds I: Nucleophilic Acyl Substitution
722(66)
Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives
724(5)
Structures of Carboxylic Acids and Carboxylic Acid Derivatives
729(1)
Physical Properties of Carbonyl Compounds
730(1)
Naturally Occurring Carboxylic Acids and Carboxylic Acid Derivatives
731(2)
How Class I Carbonyl Compounds React
733(4)
Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives
737(1)
General Mechanism for Nucleophilic Acyl Substitution Reactions
738(1)
Reactions of Acyl Halides
739(3)
Reactions of Acid Anhydrides
742(1)
Reactions of Esters
743(3)
Acid-Catalyzed Ester Hydrolysis and Transesterification
746(5)
Hydroxide-Ion-Promoted Ester Hydrolysis
751(1)
How the Mechanism for Nucleophilic Acyl Substitution Reactions Was Confirmed
752(2)
Soaps, Detergents, and Micelles
754(3)
Reactions of Carboxylic Acids
757(1)
Reactions of Amides
758(2)
The Hydrolysis of Amides Is Catalyzed by Acids
760(3)
The Hydrolysis of an Imide: A Way to Synthesize Primary Amines
763(1)
The Hydrolysis of Nitriles
764(1)
Designing a Synthesis V: The Synthesis of Cyclic Compounds
765(2)
How Chemists Activate Carboxylic Acids
767(1)
How Cells Activate Carboxylic Acids
768(4)
Dicarboxylic Acids and Their Derivatives
772(16)
Summary
775(1)
Summary of Reactions
776(2)
Key Terms
778(1)
Problems
779
Problem-Solving Strategy
758
Box Features: The Discovery of Penicillin
732(1)
Dalmatians: The High Cost of Black Spots
733(12)
Aspirin
745(11)
Making Soap
756(4)
Nature's Sleeping Pill
760(2)
Penicillin and Drug Resistance
762(1)
Penicillins in Clinical Use
762(9)
Nerve Impulses, Paralysis, and Insecticides
771(3)
Synthetic Polymers
774(1)
Dissolving Sutures
774(14)
Carbonyl Compounds II: Reactions of Aldehydes and Ketones · More Reactions of Carboxylic Acid Derivatives · Reactions of α,β-Unsaturated Carbonyl Compounds
788(62)
Nomenclature of Aldehydes and Ketones
790(3)
Relative Reactivities of Carbonyl Compounds
793(2)
How Aldehydes and Ketones React
795(1)
Reactions of Carbonyl Compounds with Grignard Reagents
796(4)
Reactions of Carbonyl Compounds with Acetylide Ions
800(1)
Reactions of Carbonyl Compounds with Hydride Ion
800(5)
Reactions of Aldehydes and Ketones with Hydrogen Cyanide
805(1)
Reactions of Aldehydes and Ketones with Amines and Derivatives of Amines
806(8)
Reactions of Aldehydes and Ketones with Water
814(2)
Reactions of Aldehydes and Ketones with Alcohols
816(3)
Protecting Groups
819(3)
Addition of Sulfur Nucleophiles
822(1)
The Wittig Reaction Forms an Alkene
822(4)
Stereochemistry of Nucleophilic Addition Reactions: Re and Si Faces
826(1)
Designing a Synthesis VI: Disconnections, Synthons, and Synthetic Equivalents
827(3)
Nucleophilic Addition to α,β-Unsaturated Aldehydes and Ketones
830(4)
Nucleophilic Addition to α,β-Unsaturated Carboxylic Acid Derivatives
834(1)
Enzyme-Catalyzed Additions to α,β-Unsaturated Carbonyl Compounds
835(15)
Summary
836(1)
Summary of Reactions
836(4)
Key Terms
840(1)
Problems
841
Problem-Solving Strategy
818
Box Features: Butanedione: An Unpleasant Compound
792(19)
Identifying of Aldehydes and Ketones without Using Spectroscopy
811(4)
Preserving Biological Specimens
815(10)
β-Carotene
825(2)
Enyzme-Catalyzed Carbonyl Additions
827(2)
Synthesizing Organic Compounds
829(1)
Semisynthetic Drugs
830(3)
Cancer Chemotherapy
833(2)
Enzyme-Catalyzed Cis-Trans Interconversion
835(15)
Carbonyl Compounds III: Reactions at the α-Carbon
850(57)
The Acidity of an α-Hydrogen
851(4)
Keto-Enol Tautomers
855(1)
Enolization
856(1)
How Enols and Enolate Ions React
857(2)
Halogenation of the α-Carbon of Aldehydes and Ketones
859(2)
Halogenation of the α-Carbon of Carboxylic Acids: The Hell-Volhard-Zelinski Reaction
861(1)
α-Halogenated Carbonyl Compounds Are Useful in Synthesis
862(1)
Using LDA to Form an Enolate Ion
863(1)
Alkylation of the α-Carbon of Carbonyl Compounds
864(3)
Alkylation and Acylation of the α-Carbon Using an Enamine Intermediate
867(2)
Alkylation of the β-Carbon: The Michael Reaction
869(2)
An Aldol Addition Forms β-Hydroxyaldehydes or β-Hydroxyketones
871(2)
Dehydration of Aldol Addition Products Forms α,β-Unsaturated Aldehydes and Ketones
873(1)
The Mixed Aldol Addition
874(2)
A Claisen Condensation Forms a β-Keto Ester
876(2)
The Mixed Claisen Condensation
878(2)
Intramolecular Condensation and Addition Reactions
880(4)
3-Oxocarboxylic Acids Can Be Decarboxylated
884(2)
The Malonic Ester Synthesis: A Way to Synthesize a Carboxylic Acid
886(2)
The Acetoacetic Ester Synthesis: A Way to Synthesize a Methyl Ketone
888(1)
Designing a Synthesis VII: Making New Carbon-Carbon Bonds
889(2)
Reactions at the α-Carbon in Biological Systems
891(16)
Summary
895(1)
Summary of Reactions
896(3)
Key Terms
899(1)
Problems
899
Problem-Solving Strategy
883
Box Features: The Synthesis of Aspirin
865(42)
Part 7 More About Oxidation-Reduction Reactions and Amines
907(70)
More About Oxidation-Reduction Reactions
908(35)
Reduction Reactions
911(6)
Oxidation of Alcohols
917(2)
Oxidation of Aldehydes and Ketones
919(3)
Designing a Synthesis VIII: Controlling Stereochemistry
922(1)
Hydroxylation of Alkenes
923(2)
Oxidative Cleavage of 1,2-Diols
925(1)
Oxidative Cleavage of Alkenes
926(5)
Oxidative Cleavage of Alkynes
931(1)
Designing a Synthesis IX: Functional Group Interconversion
932(11)
Summary
933(1)
Summary of Reactions
934(2)
Key Terms
936(1)
Problems
936
Problem-Solving Strategy
925
Box Features: The Role of Hydrates in the Oxidation of Primary Alcohols
918(1)
Treating Alcoholism with Antabuse
919(1)
Fetal Alcohol Syndrome
919(24)
More About Amines · Heterocyclic Compounds
943(34)
More About Amine Nomenclature
944(1)
More About the Acid-Base Properties of Amines
945(1)
Amines React as Bases and as Nucleophiles
946(1)
Quaternary Ammonium Hydroxides Undergo Elimination Reactions
947(4)
Phase-Transfer Catalysis
951(1)
Oxidation of Amines · The Cope Elimination Reaction
952(1)
Synthesis of Amines
953(2)
Aromatic Five-Membered-Ring Heterocycles
955(5)
Aromatic Six-Membered-Ring Heterocycles
960(6)
Amine Heterocycles Have Important Roles in Nature
966(11)
Summary
969(1)
Summary of Reactions
969(3)
Key Terms
972(1)
Problems
972
Box Features: A Useful Bad-Tasting Compound
950(18)
Porphyrin, Bilirubin, and Jaundice
968(9)
Part 8 Bioorganic Compounds
977(254)
Carbohydrates
978(39)
Classification of Carbohydrates
979(1)
The D and L Notation
980(2)
The Configurations of Aldoses
982(1)
The Configurations of Ketoses
983(1)
Reactions of Monosaccharides in Basic Solutions
984(1)
Redox Reactions of Monosaccharides
985(2)
Monosaccharides Form Crystalline Osazones
987(2)
Lengthening the Chain: The Kiliani-Fischer Synthesis
989(1)
Shortening the Chain: The Wohl Degradation
990(1)
Stereochemistry of Glucose: The Fischer Proof
990(2)
Monosaccharides Form Cyclic Hemiacetals
992(3)
Glucose Is the Most Stable Aldohexose
995(2)
Formation of Glycosides
997(2)
The Anomeric Effect
999(1)
Reducing and Nonreducing Sugars
999(1)
Disaccharides
1000(3)
Polysaccharides
1003(3)
Some Naturally Occurring Products Derived from Carbohydrates
1006(2)
Carbohydrates on Cell Surfaces
1008(2)
Synthetic Sweeteners
1010(7)
Summary
1012(1)
Summary of Reactions
1012(2)
Key Terms
1014(1)
Problems
1014
Box Features: Measuring the Blood Glucose Levels in Diabetes
988(4)
Glucose/Dextrose
992(10)
Lactose Intolerance
1002(1)
Galactosemia
1002(2)
Why the Dentist Is Right
1004(2)
Controlling Fleas
1006(1)
Heparin
1007(1)
Vitamin C
1008(3)
The Wonder of Discovery
1011(1)
Acceptable Daily Intake
1011(6)
Amino Acids, Peptides, and Proteins
1017(46)
Classification and Nomenclature of Amino Acids
1018(5)
Configuration of the Amino Acids
1023(1)
Acid-Base Properties of Amino Acids
1024(2)
The Isoelectric Point
1026(2)
Separation of Amino Acids
1028(4)
Synthesis of Amino Acids
1032(3)
Resolution of Racemic Mixtures of Amino Acids
1035(1)
Peptide Bonds and Disulfide Bonds
1035(4)
Some Interesting Peptides
1039(1)
The Strategy of Peptide Bond Synthesis: N-Protection and C-Activation
1040(3)
Automated Peptide Synthesis
1043(2)
An Introduction to Protein Structure
1045(1)
How to Determine the Primary Structure of a Peptide or a Protein
1046(6)
Secondary Structure of Proteins
1052(3)
Tertiary Structure of Proteins
1055(2)
Quaternary Structure of Proteins
1057(1)
Protein Denaturation
1058(5)
Summary
1058(1)
Key Terms
1059(1)
Problems
1059
Problem-Solving Strategy
1048
Box Features: Proteins and Nutrition
1022(1)
Amino Acids and Disease
1023(1)
A Peptide Antibiotic
1024(8)
Water Softeners: Examples of Cation-Exchange Chromatography
1032(6)
Hair: Straight or Curly?
1038(8)
Primary Structure and Evolution
1046(9)
β-Peptides: An Attempt to Improve on Nature
1055(8)
Catalysis
1063(35)
Catalysis in Organic Reactions
1065(1)
Acid Catalysis
1066(3)
Base Catalysis
1069(1)
Nucleophilic Catalysis
1070(2)
Metal-Ion Catalysis
1072(2)
Intramolecular Reactions
1074(2)
Intramolecular Catalysis
1076(3)
Catalysis in Biological Reactions
1079(2)
Enzyme-Catalyzed Reactions
1081(17)
Summary
1094(1)
Key Terms
1094(1)
Problems
1095
Box Features: The Nobel Prize
1065(33)
The Organic Mechanisms of the Coenzymes
1098(39)
An Introduction to Metabolism
1101(1)
The Vitamin Needed for Many Redox Reactions: Vitamin B3
1101(6)
Flavin Adenine Dinucleotide and Flavin Mononucleotide: Vitamin B2
1107(3)
Thiamine Pyrophosphate: Vitamin B1
1110(5)
Biotin: Vitamin H
1115(2)
Pyridoxal Phosphate: Vitamin B6
1117(7)
Coenzyme B12: Vitamin B12
1124(3)
Tetrahydrofolate: Folic Acid
1127(4)
Vitamin KH2: Vitamin K
1131(6)
Summary
1133(1)
Key Terms
1134(1)
Problems
1134
Box Features: Vitamin B1
1100(1)
``Vitamine''---An Amine Required for Life
1100(2)
Niacin Deficiency
1102(19)
Assessing the Damage After a Heart Attack
1121(10)
The First Antibiotics
1131(2)
Too Much Broccoli
1133(4)
The Chemistry of Metabolism
1137(25)
The Four Stages of Catabolism
1138(1)
ATP Is the Carrier of Chemical Energy
1139(2)
There Are Three Mechanisms for Phosphoryl Transfer Reactions
1141(3)
The ``High-Energy'' Character of Phosphoanhydride Bonds
1144(1)
Why ATP Is Kinetically Stable in a Cell
1145(1)
The Catabolism of Fats
1146(3)
The Catabolism of Carbohydrates
1149(3)
The Fates of Pyruvate
1152(1)
The Catabolism of Proteins
1153(2)
The Citric Acid Cycle
1155(3)
Oxidative Phosphorylation
1158(1)
Anabolism
1159(3)
Summary
1159(1)
Key Terms
1160(1)
Problems
1160
Problem-Solving Strategy
1152
Box Features: Differences in Metabolism
1138(17)
Phenylketonuria: An Inborn Error of Metabolism
1155(1)
Alcaptonuria
1155(4)
Basal Metabolic Rate
1159(3)
Lipids
1162(35)
Fatty Acids Are Long-Chain Carboxylic Acids
1163(2)
Waxes Are High-Molecular-Weight Esters
1165(1)
Fats and Oils
1165(5)
Phospholipids and Sphingolipids Are Components of Membranes
1170(3)
Prostaglandins Regulate Physiological Responses
1173(4)
Terpenes Contain Carbon Atoms in Multiples of Five
1177(2)
Vitamin A Is a Terpene
1179(1)
How Terpenes Are Biosynthesized
1180(6)
Steroids Are Chemical Messengers
1186(4)
How Nature Synthesizes Cholesterol
1190(2)
Synthetic Steroids
1192(5)
Summary
1192(1)
Key Terms
1193(1)
Problems
1193
Box Features: Omega Fatty Acids
1165(4)
Olestra: Nonfat with Flavor
1169(1)
Whales and Echolocation
1169(3)
Snake Venom
1172(1)
Is Chocolate a Health Food?
1172(1)
Multiple Sclerosis and the Myelin Sheath
1173(16)
Cholesterol and Heart Disease
1189(1)
Clinical Treatment of High Cholesterol
1190(7)
Nucleosides, Nucleotides, and Nucleic Acids
1197(34)
Nucleosides and Nucleotides
1198(4)
Other Important Nucleotides
1202(1)
Nucleic Acids Are Composed of Nucleotide Subunits
1202(5)
DNA Is Stable but RNA Is Easily Cleaved
1207(1)
Biosynthesis of DNA Is Called Replication
1207(2)
Biosynthesis of RNA Is Called Transcription
1209(1)
There Are Three Kinds of RNA
1210(2)
Biosynthesis of Proteins Is Called Translation
1212(4)
Why DNA Contains Thymine Instead of Uracil
1216(1)
How the Base Sequence of DNA Is Determined
1217(3)
Polymerase Chain Reaction (PCR)
1220(1)
Genetic Engineering
1221(1)
Laboratory Synthesis of DNA Strands
1222(9)
Summary
1227(1)
Key Terms
1228(1)
Problems
1228
Box Features: The Structure of DNA: Watson, Crick, Franklin, and Wilkins
1199(17)
Sickle Cell Anemia
1216(1)
Antibiotics That Act by Inhibiting Translation
1216(5)
DNA Fingerprinting
1221(1)
Resisting Herbicides
1222(9)
Part 9 Special Topics in Organic Chemistry
1231
Synthetic Polymers
1232(30)
There Are Two Major Classes of Synthetic Polymers
1233(1)
Chain-Growth Polymers
1234(11)
Stereochemistry of Polymerization · Ziegler-Natta Catalysts
1245(1)
Polymerization of Dienes · The Manufacture of Rubber
1246(2)
Copolymers
1248(1)
Step-Growth Polymers
1249(5)
Physical Properties of Polymers
1254(8)
Summary
1257(1)
Key Terms
1258(1)
Problems
1258
Box Features: Recycling Symbols
1239(16)
Designing a Polymer
1255(7)
Pericyclic Reactions
1262(31)
Three Kinds of Pericyclic Reations
1263(2)
Molecular Orbitals and Orbital Symmetry
1265(4)
Electrocyclic Reactions
1269(6)
Cycloaddition Reactions
1275(4)
Sigmatropic Rearrangements
1279(5)
Pericyclic Reactions in Biological Systems
1284(3)
Summary of the Selection Rules for Pericyclic Reactions
1287(6)
Summary
1287(1)
Key Terms
1288(1)
Problems
1288
Box Features: Luminescence
1278(8)
The Sunshine Vitamin
1286(7)
The Organic Chemistry of Drugs: Discovery and Design
1293
Naming Drugs
1297(1)
Lead Compounds
1297(1)
Molecular Modification
1298(2)
Random Screening
1300(2)
Serendipity in Drug Development
1302(2)
Receptors
1304(3)
Drugs as Enzyme Inhibitors
1307(4)
Designing a Suicide Substrate
1311(1)
Quantitative Structure-Activity Relationships (QSAR)
1312(2)
Molecular Modeling
1314(1)
Combinatorial Organic Synthesis
1314(2)
Antiviral Drugs
1316(1)
Economics of Drugs · Governmental Regulations
1317
Summary
1317(1)
Key Terms
1318(1)
Problems
1318
Box Features: Drug Safety
1302(15)
Orphan Drugs
1317
Appendices A1
I Physical Properties of Organic Compounds
1(7)
II pKa Values
8(2)
III Derivations of Rate Laws
10(3)
IV Summary of Methods Used to Synthesize a Particular Functional Group
13(4)
V Summary of Methods Employed to Form Carbon-Carbon Bonds
17(1)
VI Spectroscopy Tables
18(6)
Answers to Selected Problems 24
Glossary 1(1)
Photo Credits 1(1)
Index 1


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