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Fundamentals Of Organic Chemistry

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Edition:
6th
ISBN13:

9780495012030

ISBN10:
0495012033
Format:
Hardcover
Pub. Date:
3/29/2006
Publisher(s):
Cengage Learning
List Price: $316.33

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Summary

Written for the short course?where content must be thorough, but to-the-point, FUNDAMENTALS OF ORGANIC CHEMISTRY, Sixth Edition, continues to provide an effective, clear, and readable introduction to the beauty and logic of organic chemistry. McMurry presents only those subjects needed for a brief course while maintaining the important pedagogical tools commonly found in larger books. With clear explanations, thought-provoking examples, and an innovative vertical format for explaining reaction mechanisms, FUNDAMENTALS takes a modern approach: primary organization is by functional group, beginning with the simple (alkanes) and progressing to the more complex. Within the primary organization, there is also an emphasis on explaining the fundamental mechanistic similarities of reactions. Through this approach, memorization is minimized and understanding is maximized. The sixth edition brings in new content that applies organic chemistry to students, for example all of the chapter openers have been changed and incorporate a model and photograph of an application of organic chemistry such as Taxol from the pacific yew tree. The book introduces a running application in the Interlude boxes and in the problems relating agricultural chemicals intended to unify the subject further for students. All of the problems have been reorganized by topic to make easier to assign and review. New problem categories have been added. The new problem categories are "In the Field with Agrochemicals" and "In the Medicine Cabinet" to reinforce the focus on applications.

Table of Contents

Preface xiii
Structure and Bonding; Acids and Bases
Atomic Structure
2(2)
Electron Configuration of Atoms
4(1)
Development of Chemical Bonding Theory
5(1)
The Nature of Chemical Bonds
6(3)
Forming Covalent Bonds: Valence Bond Theory
9(1)
Hybridization: sp3 Orbitals and the Structure of Methane
10(1)
Hybridization: sp3 Orbitals and the Structure of Ethane
11(1)
Double and Triple Bonds
12(4)
Polar Covalent Bonds: Electronegativity
16(2)
Acids and Bases: The Brønsted-Lowry Definition
18(4)
Acids and Bases: The Lewis Definition
22(12)
Interlude: In The Field With Triazine Herbicides: Risk Versus Benefits
24(2)
Summary and Key Words
26(1)
Exercises
27(7)
The Nature of Organic Molecules
Functional Groups
34(6)
Alkanes and Alkyl Groups: Isomers
40(5)
Naming Branched-Chain Alkanes
45(3)
Properties of Alkanes
48(2)
Conformations of Ethane
50(2)
Drawing Chemical Structures
52(2)
Cycloalkanes
54(1)
Cis-Trans Isomerism in Cycloalkanes
55(2)
Conformations of Some Cycloalkanes
57(1)
Axial and Equatorial Bonds in Cyclohexane
58(1)
Conformational Mobility of Cyclohexane
59(15)
Interlude: The Sources And Development Of Drugs
62(2)
Summary and Key Words
64(1)
Exercises
65(9)
The Nature of Organic Reactions: Alkenes
Naming Alkenes
74(2)
Electronic Structure of Alkenes
76(1)
Cis-Trans Isomers of Alkenes
77(2)
Sequence Rules: The E,Z Designation
79(3)
Kinds of Organic Reactions
82(2)
How Reactions Occur: Mechanisms
84(1)
Mechanisms of Polar Reactions
85(3)
The Mechanism of an Organic Reaction: Addition of HCI to Ethylene
88(3)
Describing a Reaction: Reaction Energy Diagrams and Transition States
91(1)
Describing a Reaction: Energetics and Catalysis
92(11)
Interlude: Terrenes: Naturally Occurring Alkenes
94(2)
Summary and Key Words
96(1)
Exercises
96(7)
Reactions of Alkenes and Alkynes
Addition of HX to Alkenes: Hydrohalogenation
103(1)
Orientation of Alkene Addition Reactions: Markovnikov's Rule
104(2)
Carbocation Structure and Stability
106(2)
Addition of H2O to Alkenes: Hydration
108(2)
Addition of X2 to Alkenes: Halogenation
110(2)
Addition of H2 to Alkenes: Hydrogenation
112(1)
Oxidation of Alkenes: Hydroxylation and Cleavage
113(2)
Addition of Radicals to Alkenes: Polymers
115(2)
Conjugated Dienes
117(2)
Stability of Allylic Carbocations: Resonance
119(2)
Drawing and Interpreting Resonance Forms
121(2)
Alkynes and Their Reactions
123(17)
Interlude: Natural Rubber
128(1)
Summary and Key Words
129(1)
Summary of Reactions
129(2)
Exercises
131(9)
Aromatic Compounds
Structure of Benzene: The Kekule Proposal
140(1)
Structure of Benzene: The Resonance Proposal
141(1)
Naming Aromatic Compounds
142(2)
Electrophilic Aromatic Substitution Reactions: Bromination
144(3)
Other Electrophilic Aromatic Substitution Reactions
147(2)
The Friedel-Crafts Alkylation and Acylation Reactions
149(2)
Substituent Effects in Electrophilic Aromatic Substitution
151(2)
An Explanation of Substituent Effects
153(3)
Oxidation and Reduction of Aromatic Compounds
156(1)
Aromaticity in Nonbenzene Rings and Polycyclic Compounds
157(1)
Organic Synthesis
158(13)
Interlude: In The Field With Triazine Herbicides
161(2)
Summary and Key Words
163(1)
Summary of Reactions
163(1)
Exercises
164(7)
Stereochemistry
Stereochemistry and the Tetrahedral Carbon
171(2)
Finding Handedness in Molecules
173(4)
Optical Activity
177(1)
Specific Rotation
177(1)
Pasteur's Discovery of Enantiomers
178(1)
Sequence Rules for Specifying Configuration
179(4)
Enantiomers and Diastereomers
183(2)
Meso Compounds
185(2)
Molecules with More Than Two Stereocenters
187(1)
The Chiral Environment
187(3)
A Brief Review of Isomerism
190(1)
Chirality in Nature
191(10)
Interlude: Chiral Drugs
192(1)
Summary and Key Words
193(1)
Exercises
194(7)
Alkyl Halides
Naming Alkyl Halides
201(1)
Preparing Alkyl Halides
202(2)
Reactions of Alkyl Halides: Grignard Reagents
204(2)
Nucleophilic Substitution Reactions
206(2)
The SN2 Reaction
208(4)
The SN1 Reaction
212(4)
Eliminations: The E2 Reaction
216(2)
Eliminations: The E1 Reaction
218(1)
A Summary of Reactivity: SN1, SN2, E1, E2
219(1)
Substitution Reactions in Living Organisms
220(12)
Interlude: Naturally Occurring Organohalogen Compounds
221(1)
Summary and Key Words
222(1)
Summary of Reactions
222(1)
Exercises
223(9)
Alcohols, Phenols, and Ethers
Naming Alcohols, Phenols, and Ethers
232(2)
Properties of Alcohols, Phenols, and Ethers: Hydrogen Bonding
234(1)
Properties of Alcohols and Phenols: Acidity
235(2)
Synthesis of Alcohols
237(3)
Reactions of Alcohols
240(5)
Synthesis and Reactions of Phenols
245(2)
Synthesis and Reactions of Ethers
247(1)
Epoxides
248(2)
Thiols and Sulfides
250(14)
Interlude: In The Field With Triazine Herbicides
252(1)
Summary and Key Words
253(1)
Summary of Reactions
254(2)
Exercises
256(8)
Aldehydes and Ketones: Nucleophilic Addition Reactions
Chemistry of the Carbonyl Group
264(1)
Naming Aldehydes and Ketones
265(2)
Synthesis of Aldehydes and Ketones
267(1)
Oxidation of Aldehydes
268(1)
Nucleophilic Addition Reactions of Aldehydes and Ketones
269(2)
Reduction
271(1)
Nucleophilic Addition of Water: Hydration
272(2)
Nucleophilic Addition of Alcohols: Acetal Formation
274(3)
The Importance of Hemiacetals and Acetals: Nature and the Laboratory
277(2)
Addition of Amines to Form lmines
279(2)
Nucleophilic Addition of Grignard Reagents: Alcohol Formation
281(2)
Conjugate Addition Reactions
283(14)
Interlude: Carbonyl Compounds For Insect Control
285(1)
Summary and Key Words
286(1)
Summary of Reactions
287(1)
Exercises
288(9)
Carboxylic Acids and Derivatives
Naming Carboxylic Acids and Derivatives
297(3)
Occurrence and Properties of Carboxylic Acids and Derivatives
300(1)
Acidity of Carboxylic Acids
301(3)
Synthesis of Carboxylic Acids
304(1)
Nucleophilic Acyl Substitution Reactions
305(2)
The Tetrahedral Intermediate
307(2)
Overview of Reactions
309(1)
Reactions of Carboxylic Acids
310(1)
Chemistry of Acid Halides
311(3)
Chemistry of Acid Anhydrides
314(2)
Chemistry of Esters
316(4)
Chemistry of Amides
320(2)
Chemistry of Nitriles
322(2)
Polymers from Carbonyl Compounds: Polymides and Polyesters
324(2)
Enzymes in Organic Synthesis
326(18)
Interlude: β-Lactam Antibiotics---Part I
328(2)
Summary and Key Words
330(1)
Summary of Reactions
330(2)
Exercises
332(12)
Carbonyl Alpha-Substitution Reactions and Condensation Reactions
Keto-Enol Tautomerism
344(3)
Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions
347(1)
Alpha Halogenation of Aldehydes and Ketones
347(2)
Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
349(4)
Reactivity of Enolate Ions
353(1)
Alkylation of Enolate Ions
353(3)
Enolate Alkylation and the Dawn of Modern Medicine
356(1)
Carbonyl Condensation Reactions
356(1)
Condensations of Aldehydes and Ketones: The Aldol Reaction
357(2)
Dehydration of Aldol Products: Synthesis of Enones
359(2)
Condensations of Esters: The Claisen Condensation Reaction
361(2)
Biological Carbonyl Reactions
363(13)
Interlude: β-Lactam Antibiotics-Part II
364(2)
Summary and Key Words
366(1)
Summary of Reactions
367(1)
Exercises
368(8)
Amines
Naming Amines
376(2)
Structure and Properties of Amines
378(1)
Basicity of Amines
379(3)
Synthesis of Amines
382(5)
Reactions of Amines
387(1)
Heterocyclic Amines
388(4)
Alkaloids: Naturally Occurring Amines
392(13)
Interlude: Opium And Opiates
393(1)
Summary and Key Words
394(1)
Summary of Reactions
394(1)
Exercises
395(7)
Interlude: The Road Map to Chemical Reactions
402(3)
Structure Determination
Electromagnetic Radiation: A Common Probe of Structure
405(2)
X-Ray Crystallography
407(2)
Mass Spectrometry
409(2)
Ultraviolet Spectroscopy
411(1)
Interpreting Ultraviolet Spectra: The Effect of Conjugation
412(1)
Infrared Spectroscopy of Organic Molecules
413(5)
Nuclear Magnetic Resonance Spectroscopy
418(1)
The Nature of NMR Absorptions
419(2)
Chemical Shifts
421(1)
Chemical Shifts in 1H NMR Spectra
422(2)
Integration of 1H NMR Spectra: Proton Counting
424(1)
Spin-Spin Splitting in 1H NMR Spectra
424(4)
Uses of 1H NMR Spectra
428(1)
13C NMR Spectroscopy
428(14)
Interlude: Magnetic Resonance Imaging (MRI)
430(1)
Summary and Key Words
431(1)
Exercises
432(10)
Biomolecules: Carbohydrates
Classification of Carbohydrates
442(1)
Configurations of Monosaccharides: Fischer Projections
443(3)
D,L Sugars
446(2)
Configurations of Aldoses
448(2)
Cyclic Structures of Monosaccharides: Hemiacetal Formation
450(1)
Monosaccharide Anomers: Mutarotation
451(2)
Reactions of Monosaccharides
453(5)
Disaccharides
458(1)
Polysaccharides
459(2)
Other Important Carbohydrates
461(1)
Cell-Surface Carbohydrates and Carbohydrate Vaccines
462(2)
Plants: An Alternative to Petroleum?
464(12)
Interlude: Sweetness
465(1)
Summary and Key Words
466(1)
Exercises
467(9)
Biomolecules: Amino Acids, Peptides, and Proteins
Structures of Amino Acids
476(5)
Isoelectric Points
481(2)
Peptide Synthesis in the Laboratory
483(5)
Peptide Synthesis in Nature
488(1)
Covalent Bonding in Peptides
489(2)
Peptide Structure Determination: Amino Acid Analysis
491(1)
Peptide Sequencing: The Edman Degradation Method
492(2)
Classification of Proteins
494(1)
Protein Structure
495(2)
Enzymes
497(2)
How Do Enzymes Work? Citrate Synthase
499(11)
Interlude: Killing Weeds, Not Crops: One Route To Selectivity
502(1)
Summary and Key Words
503(1)
Exercises
504(6)
Biomolecules: Lipids and Nucleic Acids
Lipids
510(1)
Fats and Oils
511(3)
Soaps
514(2)
Phospholipids
516(1)
Steroids
517(2)
The Chemistry of Statin Drugs
519(2)
Nucleic Acids and Nucleotides
521(3)
Structure of DNA
524(1)
Base Pairing in DNA: The Watson-Crick Model
525(2)
Nucleic Acids and Heredity
527(1)
Replication of DNA
527(2)
Structure and Synthesis of RNA: Transcription
529(1)
RNA and Protein Biosynthesis: Translation
530(3)
Sequencing DNA
533(2)
The Polymerase Chain Reaction
535(1)
RNA: A Paradigm Breaker
535(8)
Interlude: DNA Fingerprinting
537(1)
Summary and Key Words
538(1)
Exercises
539(4)
The Organic Chemistry of Metabolic Pathways
ATP: The Currency of Biochemical Reactions
543(3)
Catabolism of Fats: β-Oxidation Pathway
546(4)
Catabolism of Carbohydrates: Glycolysis
550(4)
The Citric Acid Cycle
554(3)
Catabolism of Proteins: Transamination
557(2)
The Organic Chemistry of Metabolic Pathways: A Summary
559(1)
Interlude: Borrowing Metabolic Pathways For Bioremediation
559(1)
Summary and Key Words
560(1)
Exercises
561
Appendix A: Nomenclature of Polyfunctional Organic Compounds 1(6)
Appendix B: Glossary 7(12)
Appendix C: Answers to Selected In-Chapter Problems 19
Index 1


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