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Fundamentals of Organic Chemistry: With Infotrac

by
Edition:
5th
ISBN13:

9780534395735

ISBN10:
0534395732
Format:
Hardcover
Pub. Date:
7/15/2002
Publisher(s):
Brooks Cole
List Price: $334.66

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Summary

Written for the short course-where content must be thorough, but to-the-point, FUNDAMENTALS OF ORGANIC CHEMISTRY, Fifth Edition provides 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. This new edition represents a major revision. The text has been revised at the sentence level to further improve clarity and readability; many new examples and topics of biological relevance have been added; and many new features have been introduced.

Table of Contents

Preface xvi
A Note for Students xxi
Structure and Bonding; Acids and Bases
1(33)
Atomic Structure
3(2)
Electron Configuration of Atoms
5(1)
Development of Chemical Bonding Theory
6(1)
The Nature of Chemical Bonds
7(3)
Forming Covalent Bonds: Valence Bond Theory
10(1)
Hybridization: sp3 Orbitals and the Structure of Methane
11(1)
Hybridization: sp3 Orbitals and the Structure of Ethane
12(1)
Hybridization: sp2 Orbitals and the Structure of Ethylene
13(3)
Hybridization: sp Orbitals and the Structure of Acetylene
16(1)
Polar Covalent Bonds: Electronegativity
17(3)
Acids and Bases: The Brønsted--Lowry Definition
20(4)
Acids and Bases: The Lewis Definition
24(10)
Interlude Chemicals, Toxicity, and Risk
26(1)
Summary and Key Words
27(1)
Working Problems
28(1)
Visualizing Chemistry / Additional Problems
29(5)
The Nature of Organic Compounds: Alkanes
34(40)
Functional Groups
35(6)
Alkanes and Alkyl Groups: Isomers
41(5)
Naming Branched-Chain Alkanes
46(3)
Properties of Alkanes
49(1)
Conformations of Ethane
50(3)
Drawing Chemical Structures
53(1)
Cycloalkanes
54(1)
Cis-Trans Isomerism in Cycloalkanes
55(2)
Conformations of Some Cycloalkanes
57(3)
Axial and Equatorial Bonds in Cyclohexane
60(1)
Conformational Mobility of Cyclohexane
61(13)
Interlude Gasoline
64(2)
Summary and Key Words
66(1)
Visualizing Chemistry / Additional Problems
67(7)
The Nature of Organic Reactions: Alkenes
74(31)
Naming Alkenes
75(3)
Electronic Structure of Alkenes
78(1)
Cis--Trans Isomers of Alkenes
79(2)
Sequence Rules: The E,Z Designation
81(3)
Kinds of Organic Reactions
84(2)
How Reactions Occur: Mechanisms
86(3)
The Mechanism of an Organic Reaction: Addition of HCI to Ethylene
89(3)
Describing a Reaction: Reaction Energy Diagrams and Transition States
92(2)
Describing a Reaction: Intermediates
94(11)
Interlude Terpenes: Naturally Occurring Alkenes
96(2)
Summary and Key Words
98(1)
Visualizing Chemistry / Additional Problems
99(6)
Reactions of Alkenes and Alkynes
105(38)
Addition of HX to Alkenes: Hydrohalogenation
106(1)
Orientation of Alkene Addition Reactions: Markovnikov's Rule
106(3)
Carbocation Structure and Stability
109(2)
Addition of H2O to Alkenes: Hydration
111(2)
Addition of X2 to Alkenes: Halogenation
113(2)
Addition of H2 to Alkenes: Hydrogenation
115(1)
Oxidation of Alkenes: Hydroxylation and Cleavage
116(2)
Biological Addition Reactions of Alkenes
118(1)
Addition of Radicals to Alkenes: Polymers
119(3)
Conjugated Dienes
122(2)
Stability of Allylic Carbocations: Resonance
124(2)
Drawing and Interpreting Resonance Forms
126(2)
Alkynes and Their Reactions
128(15)
Interlude Natural Rubber
133(1)
Summary and Key Words
134(1)
Summary of Reactions / Visualizing Chemistry / Additional Problems
135(8)
Aromatic Compounds
143(34)
Structure of Benzene: The Kekule Proposal
144(1)
Structure of Benzene: The Resonance Proposal
145(1)
Naming Aromatic Compounds
146(3)
Electrophilic Aromatic Substitution Reactions: Bromination
149(4)
Other Electrophilic Aromatic Substitution Reactions
153(1)
The Friedel-Crafts Alkylation and Acylation Reactions
154(2)
Substituent Effects in Electrophilic Aromatic Substitution
156(2)
An Explanation of Substituent Effects
158(4)
Oxidation and Reduction of Aromatic Compounds
162(1)
Polycyclic Aromatic Hydrocarbons
163(1)
Organic Synthesis
164(13)
Interlude Aspirin, NSAIDs, and COX-2 Inhibitors
167(2)
Summary and Key Words
169(1)
Summary of Reactions / Visualizing Chemistry / Additional Problems
170(7)
Stereochemistry
177(34)
Stereochemistry and the Tetrahedral Carbon
178(2)
The Reason for Handedness in Molecules: Chirality
180(3)
Optical Activity
183(1)
Specific Rotation
184(2)
Pasteur's Discovery of Enantiomers
186(1)
Sequence Rules for Specifying Configuration
187(4)
Diastereomers
191(2)
Meso Compounds
193(2)
Molecules with More Than Two Stereocenters
195(1)
Racemic Mixtures and the Resolution of Enantiomers
196(3)
Physical Properties of Stereoisomers
199(1)
A Brief Review of Isomerism
199(2)
Chirality in Nature
201(10)
Interlude Chiral Drugs
203(1)
Summary and Key Words
204(1)
Visualizing Chemistry / Additional Problems
205(6)
Alkyl Halides
211(32)
Naming Alkyl Halides
212(1)
Preparing Alkyl Halides
213(2)
Reactions of Alkyl Halides: Grignard Reagents
215(2)
Nucleophilic Substitution Reactions
217(3)
The SN2 Reaction
220(4)
The SN1 Reaction
224(4)
Eliminations: The E2 Reaction
228(2)
Eliminations: The E1 Reaction
230(2)
A Summary of Reactivity: SN1, S2, E1, E2
232(1)
Substitution Reactions in Living Organisms
233(10)
Interlude Naturally Occurring Organohalogen Compounds
234(1)
Summary and Key Words
235(1)
Summary of Reactions / Visualizing Chemistry / Additional Problems
235(8)
Alcohols, Phenols, and Ethers
243(33)
Naming Alcohols, Phenols, and Ethers
244(2)
Properties of Alcohols, Phenols, and Ethers: Hydrogen Bonding
246(2)
Properties of Alcohols and Phenols: Acidity
248(2)
Synthesis of Alcohols
250(3)
Reactions of Alcohols
253(5)
Synthesis and Reactions of Phenols
258(3)
Synthesis and Reactions of Ethers
261(1)
Cyclic Ethers: Epoxides
262(2)
Thiols and Sulfides
264(12)
Interlude Ethyl Alcohol: Chemical, Drug, and Poison
266(1)
Summary and Key Words
267(1)
Summary of Reactions / Visualizing Chemistry / Additional Problems
268(8)
Aldehydes and Ketones: Nucleophilic Addition Reactions
276(29)
The Nature of Carbonyl Compounds
277(2)
Naming Aldehydes and Ketones
279(2)
Synthesis of Aldehydes and Ketones
281(1)
Oxidation of Aldehydes
282(1)
Nucleophilic Addition Reactions of Aldehydes and Ketones: Reduction
283(2)
Nucleophilic Addition of Water: Hydration
285(3)
Nucleophilic Addition of Alcohols: Acetal Formation
288(2)
Nucleophilic Addition of Amines: Imine Formation
290(1)
Nucleophilic Addition of Grignard Reagents: Alcohol Formation
291(3)
Conjugate Nucleophilic Addition Reactions
294(1)
Some Biological Nucleophilic Addition Reactions
295(10)
Interlude Carbonyl Compounds for Insect Control
297(1)
Summary and Key Words
298(1)
Summary of Reactions / Visualizing Chemistry / Additional Problems
298(7)
Carboxylic Acids and Derivatives
305(42)
Naming Carboxylic Acids and Derivatives
306(4)
Occurrence and Properties of Carboxylic Acids
310(3)
Synthesis of Carboxylic Acids
313(1)
Nucleophilic Acyl Substitution Reactions
314(3)
Reactions of Carboxylic Acids
317(3)
Chemistry of Acid Halides
320(2)
Chemistry of Acid Anhydrides
322(2)
Chemistry of Esters
324(5)
Chemistry of Amides
329(2)
Chemistry of Nitriles
331(3)
Polymers from Carbonyl Compounds: Nylons and Polyesters
334(13)
Interlude Vitamin C
336(2)
Summary and Key Words
338(1)
Summary of Reactions / Visualizing Chemistry / Additional Problems
338(9)
Carbonyl Alpha-Substitution Reactions and Condensation Reactions
347(32)
Keto--Enol Tautomerism
348(4)
Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions
352(1)
Alpha Halogenation of Aldehydes and Ketones
353(2)
Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
355(3)
Reactivity of Enolate Ions
358(1)
Alkylation of Enolate Ions
359(3)
Carbonyl Condensation Reactions
362(1)
Condensations of Aldehydes and Ketones: The Aldol Reaction
362(2)
Dehydration of Aldol Products: Synthesis of Enones
364(2)
Condensations of Esters: The Claisen Condensation Reaction
366(2)
Biological Carbonyl Reactions
368(11)
Interlude β-Lactam Antibiotics
370(1)
Summary and Key Words
371(1)
Summary of Reactions / Visualizing Chemistry / Additional Problems
372(7)
Amines
379(27)
Naming Amines
380(3)
Structure and Properties of Amines
383(1)
Basicity of Amines
383(3)
Synthesis of Amines
386(6)
Reactions of Amines
392(1)
Heterocyclic Amines
393(4)
Alkaloids: Naturally Occurring Amines
397(9)
Interlude Opium and Opiates
398(1)
Summary and Key Words
399(1)
Summary of Reactions / Visualizing Chemistry / Additional Problems
400(6)
Structure Determination
406(35)
Infrared Spectroscopy and the Electromagnetic Spectrum
407(3)
Infrared Spectroscopy of Organic Molecules
410(5)
Ultraviolet Spectroscopy
415(1)
Interpreting Ultraviolet Spectra: The Effect of Conjugation
416(2)
Nuclear Magnetic Resonance Spectroscopy
418(1)
The Nature of NMR Absorptions
419(3)
Chemical Shifts
422(1)
Chemical Shifts in 1H NMR Spectra
423(2)
Integration of 1H NMR Spectra: Proton Counting
425(1)
Spin--Spin Splitting in 1H NMR Spectra
426(4)
Uses of 1H NMR Spectra
430(1)
13C NMR Spectroscopy
430(11)
Interlude Magnetic Resonance Imaging (MRI)
433(1)
Summary and Key Words
434(1)
Visualizing Chemistry / Additional Problems
435(6)
Biomolecules: Carbohydrates
441(31)
Classification of Carbohydrates
442(2)
Configurations of Monosaccharides: Fischer Projections
444(2)
D,L Sugars
446(2)
Configurations of Aldoses
448(2)
Cyclic Structures of Monosaccharides: Hemiacetal Formation
450(2)
Monosaccharide Anomers: Mutarotation
452(2)
Reactions of Monosaccharides
454(6)
Polysaccharides
460(3)
Other Important Carbohydrates
463(1)
Cell-Surface Carbohydrates and Carbohydrate Vaccines
463(9)
Interlude Sweetness
466(1)
Summary and Key Words
467(1)
Visualizing Chemistry / Additional Problems
467(5)
Biomolecules: Amino Acids, Peptides, and Proteins
472(35)
Structures of Amino Acids
473(5)
Isoelectric Points
478(3)
Peptides and Proteins
481(1)
Covalent Bonding in Peptides
482(2)
Peptide Structure Determination: Amino Acid Analysis
484(1)
Peptide Sequencing: The Edman Degradation
484(3)
Peptide Synthesis
487(3)
Classification of Proteins
490(1)
Protein Structure
491(3)
Enzymes
494(3)
How Do Enzymes Work? Citrate Synthase
497(10)
Interlude Protein and Nutrition
500(1)
Summary and Key Words
501(1)
Visualizing Chemistry / Additional Problems
502(5)
Biomolecules: Lipids and Nucleic Acids
507(33)
Lipids
508(1)
Fats and Oils
508(3)
Soaps
511(2)
Phospholipids
513(2)
Steroids
515(2)
Nucleic Acids and Nucleotides
517(3)
Structure of DNA
520(1)
Base Pairing in DNA: The Watson--Crick Model
521(3)
Nucleic Acids and Heredity
524(1)
Replication of DNA
524(2)
Structure and Synthesis of RNA: Transcription
526(1)
RNA and Protein Biosynthesis: Translation
527(3)
Sequencing DNA
530(2)
The Polymerase Chain Reaction
532(8)
Interlude DNA Fingerprinting
534(1)
Summary and Key Words
535(1)
Visualizing Chemistry / Additional Problems
536(4)
The Organic Chemistry of Metabolic Pathways
540(1)
An Overview of Metabolism and Biochemical Energy
541(3)
Catabolism of Fats: β-Oxidation Pathway
544(5)
Catabolism of Carbohydrates: Glycolysis
549(5)
The Citric Acid Cycle
554(3)
Catabolism of Proteins: Transamination
557(2)
The Organic Chemistry of Metabolic Pathways: A Summary
559(1)
Interlude Basal Metabolism
560(1)
Summary and Key Words
561(1)
Visualizing Chemistry / Additional Problems
561
Appendixes
A Nomenclature of Polyfunctional Organic Compounds
1(7)
B Glossary
8(10)
C Answers to Selected In-Chapter Problems
18
Index 1


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