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Organic Chemistry + 1pass for Organic ChemistryNOW: A Biological Approach

ISBN: 9780495015253 | 0495015253
Edition: 1st
Format: Hardcover
Publisher: Cengage Learning
Pub. Date: 3/28/2006

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SummaryTable of Contents
Renowned for his student-friendly writing style, John McMurry introduces a new way to teach organic chemistry: ORGANIC CHEMISTRY: A BIOLOGICAL APPROACH. Traditional foundations of organic chemistry are enhanced by a consistent integration of biological examples and discussion of the organic chemistry of biological pathways. This innovative text is coupled with media integration through Organic ChemistryNow and Organic OWL, providing instructors and students the tools they need to succeed.
Structure and Bonding
1(34)
Atomic Structure: The Nucleus
3(1)
Atomic Structure: Orbitals
... MORE4(1)
Atomic Structure: Electron Configurations
5(1)
Development of Chemical Bonding Theory
6(4)
The Nature of Chemical Bonds: Valence Bond Theory
10(1)
sp3 Hybrid Orbitals and the Structure of Methane
11(2)
sp3 Hybrid Orbitals and the Structure of Ethane
13(1)
sp2 Hybrid Orbitals and the Structure of Ethylene
14(3)
sp Hybrid Orbitals and the Structure of Acetylene
17(2)
Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur
19(2)
The Nature of Chemical Bonds: Molecular Orbital Theory
21(1)
Drawing Chemical Structures
22(13)
Lagniappe: Chemicals, Toxicity, and Risk
26(1)
Summary
26(2)
Exercises
28(7)
Polar Covalent Bonds: Acids and Bases
35(40)
Polar Covalent Bonds: Electronegativity
35(3)
Polar Covalent Bonds: Dipole Moments
38(2)
Formal Charges
40(3)
Resonance
43(2)
Rules for Resonance Forms
45(2)
Drawing Resonance Forms
47(3)
Acids and Bases: The Bronsted-Lowry Definition
50(1)
Acid and Base Strength
51(2)
Predicting Acid-Base Reactions from pKa Values
53(2)
Organic Acids and Organic Bases
55(3)
Acids and Bases: The Lewis Definition
58(4)
Noncovalent Interactions between Molecules
62(13)
Lagniappe: Alkaloids: Naturally Occurring Bases
65(1)
Summary
66(1)
Exercises
67(8)
Organic Compounds: Alkanes and Their Stereochemistry
75(36)
Functional Groups
75(7)
Alkanes and Alkane Isomers
82(4)
Alkyl Groups
86(3)
Naming Alkanes
89(6)
Properties of Alkanes
95(1)
Conformations of Ethane
96(2)
Conformations of Other Alkanes
98(13)
Lagniappe: Gasoline
103(1)
Summary
104(1)
Exercises
104(7)
Organic Compounds: Cycloalkanes and Their Stereochemistry
111(30)
Naming Cycloalkanes
112(3)
Cis-Trans Isomerism in Cycloalkanes
115(3)
Stability of Cycloalkanes: Ring Strain
118(1)
Conformations of Cycloalkanes
119(2)
Conformations of Cyclohexane
121(2)
Axial and Equatorial Bonds in Cyclohexane
123(3)
Conformations of Monosubstituted Cyclohexanes
126(2)
Conformations of Disubstituted Cyclohexanes
128(3)
Conformations of Polycyclic Molecules
131(10)
Lagniappe: Molecular Mechanics
133(1)
Summary
133(1)
Exercises
134(7)
An Overview of Organic Reactions
141(38)
Kinds of Organic Reactions
141(2)
How Organic Reactions Occur: Mechanisms
143(1)
Radical Reactions
144(3)
Polar Reactions
147(4)
An Example of a Polar Reaction: Addition of H2O to Ethylene
151(3)
Using Curved Arrows in Polar Reaction Mechanisms
154(3)
Describing a Reaction: Equilibria. Rates, and Energy Changes
157(4)
Describing a Reaction: Bond Dissociation Energies
161(2)
Describing a Reaction: Energy Diagrams and Transition States
163(3)
Describing a Reaction: Intermediates
166(2)
A Comparison between Biological Reactions and Laboratory Reactions
168(11)
Lagniappe: Where Do Drugs Come From?
171(1)
Summary
172(1)
Exercises
173(6)
Alkenes and Alkynes
179(42)
Calculating a Degree of Unsaturation
180(2)
Naming Alkenes and Alkynes
182(3)
Cis-Trans Isomerism in Alkenes
185(2)
Sequence Rules: The EZ Designation
187(5)
Stability of Alkenes
192(3)
Electrophilic Addition Reactions of Alkenes
195(3)
Orientation of Electrophilic Addition: Markovnikov's Rule
198(3)
Carbocation Structure and Stability
201(3)
The Hammond Postulate
204(2)
Carbocation Rearrangements
206(15)
Lagniappe: Terpenes: Naturally Occurring Alkenes
209(1)
Summary
210(1)
Exercises
211(10)
Reactions of Alkenes and Alkynes
221(46)
Preparation of Alkenes: A Preview of Elimination Reactions
222(2)
Halogenation of Alkenes
224(2)
Halohydrins from Alkenes
226(1)
Hydration of Alkenes
227(5)
Reduction of Alkenes
232(3)
Oxidation of Alkenes: Epoxidation
235(1)
Oxidation of Alkenes: Hydroxylation
236(3)
Radical Additions to Alkenes: Alkene Polymers
239(4)
Biological Additions of Radicals to Alkenes
243(1)
Conjugated Dienes
244(4)
Reactions of Conjugated Dienes
248(3)
Reactions of Alkynes
251(16)
Lagniappe: Natural Rubber
253(1)
Summary
254(1)
Summary of Reactions
255(3)
Exercises
258(9)
Aromatic Compounds
267(52)
Structure and Stability of Benzene
270(3)
Aromaticity and the Huckel 4n + 2 Rule
273(2)
Aromatic Heterocycles
275(3)
Polycyclic Aromatic Compounds
278(3)
Reactions of Aromatic Compounds: Electrophilic Substitution
281(7)
Alkylation and Acylation of Aromatic Rings
288(4)
Substituent Effects in Electrophilic Substitutions
292(6)
Oxidation and Reduction of Aromatic Compounds
298(2)
An Introduction to Organic Synthesis: Polysubstituted Benzenes
300(19)
Lagniappe: Combinatorial Chemistry
306(1)
Summary
307(1)
Summary of Reactions
308(2)
Exercises
310(9)
Stereochemistry
319(136)
Enantiomers and the Tetrahedral Carbon
320(1)
The Reason for Handedness in Molecules: Chirality
321(4)
Optical Activity
325(2)
Pasteur's Discovery of Enantiomers
327(1)
Sequence Rules for Specifying Configuration
328(5)
Diastereomers
333(2)
Meso Compounds
335(3)
Racemates and the Resolution of Enantiomers
338(2)
A Brief Review of Isomerism
340(2)
Stereochemistry of Reactions: Addition of H2O to an Achiral Alkene
342(1)
Stereochemistry of Reactions: Addition of H2O to a Chiral Alkene
343(2)
Chirality at Nitrogen, Phosphorus, and Sulfur
345(1)
Prochirality
346(3)
Chirality in Nature
349(106)
Lagniappe: Chiral Drugs
351(1)
Summary
352(1)
Exercises
353(102)
Structure Determination: Nuclear Magnetic Resonance Spectroscopy
455(42)
Nuclear Magnetic Resonance Spectroscopy
455(2)
The Nature of NMR Absorptions
457(3)
Chemical Shifts
460(2)
13C NMR Spectroscopy: Signal Averaging and FT-NMR
462(2)
Characteristics of 13C NMR Spectroscopy
464(3)
DEPT 13C NMR Spectroscopy
467(2)
Uses of 13C NMR Spectroscopy
469(1)
1H NMR Spectroscopy and Proton Equivalence
470(3)
Chemical Shifts in 1H NMR Spectroscopy
473(2)
Integration of 1H NMR Absorptions: Proton Counting
475(1)
Spin-Spin Splitting in 1H NMR Spectra
476(6)
More Complex Spin-Spin Splitting Patterns
482(2)
Uses of 1H NMR Spectroscopy
484(13)
Lagniappe: Magnetic Resonance Imaging (MRI)
485(1)
Summary
485(1)
Exercises
486(11)
Alcohols, Phenols, and Thiols; Ethers and Sulfides
497(50)
Naming Alcohols, Phenols, and Thiols
499(2)
Properties of Alcohols, Phenols, and Thiols
501(3)
Preparation of Alcohols from Carbonyl Compounds
504(8)
Reactions of Alcohols
512(4)
Oxidation of Alcohols and Phenols
516(4)
Preparation and Reactions of Thiols
520(2)
Ethers and Sulfides
522(1)
Preparation of Ethers
523(2)
Reactions of Ethers
525(2)
Preparation and Reactions of Sulfides
527(2)
Spectroscopy of Alcohols, Phenols, and Ethers
529(18)
Lagniappe: Ethanol: Chemical, Drug, and Poison
532(1)
Summary
532(1)
Summary of Reactions
533(3)
Exercises
536(11)
A Preview of Carbonyl Chemistry
547
Kinds of Carbonyl Compounds
547
Nature of the Carbonyl Group
549
General Reactions of Carbonyl Compounds
550
Summary
555
Aldehydes and Ketones: Nucleophilic Addition Reactions
557
Naming Aldehydes and Ketones
558
Preparation of Aldehydes and Ketones
560
Oxidation of Aldehydes
561
Nucleophilic Addition Reactions of Aldehydes and Ketones
562
Nucleophilic Addition of H2O: Hydration
564
Nucleophilic Addition of Grignard and Hydride Reagents: Alcohol Formation
567
Nucleophilic Addition of Amines: Imine and Enamine Formation
568
Nucleophilic Addition of Alcohols: Acetal Formation
572
Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction
575
Biological Reductions
579
Conjugate Nucleophilic Addition to a, b-Unsaturated Aldehydes and Ketones
580
Spectroscopy of Aldehydes and Ketones
583
Lagniappe: Enantioselective Synthesis
587
Summary
588
Summary of Reactions
588
Exercises
590
Carboxylic Acids and Nitriles
601
Naming Carboxylic Acids and Nitriles
602
Structure and Properties of Carboxylic Acids
605
Biological Acids and the Henderson-Hasselbalch Equation
608
Substituent Effects on Acidity
609
Preparation of Carboxylic Acids
611
Reactions of Carboxylic Acids: An Overview
613
Chemistry of Nitriles
614
Spectroscopy of Carboxylic Acids and Nitriles
617
Lagniappe: Vitamin C
618
Summary
620
Summary of Reactions
620
Exercises
622
Amines and Heterocycles
735
Naming Amines
736
Properties of Amines
739
Basicity of Amines
740
Basicity of Arylamines
743
Biological Amines and the Henderson-Hasselbalch Equation
745
Synthesis of Amines
746
Reactions of Amines
751
Heterocyclic Amines
755
Fused-Ring Heterocycles
759
Spectroscopy of Amines
762
Lagniappe: Green Chemistry
764
Summary
765
Summary of Reactions
766
Exercises
768
Biomolecules: Amino Acids, Peptides, and Proteins
777
Structures of Amino Acids
778
Isoelectric Points
783
Synthesis of Amino Acids
784
Peptides and Proteins
787
Amino Acid Analysis of Peptides
789
Peptide Sequencing: The Edman Degradation
790
Peptide Synthesis
792
Protein Structure
797
Enzymes and Coenzymes
800
How Do Enzymes Work? Citrate Synthase
804
Lagniappe: The Protein Data Bank
807
Summary
808
Summary of Reactions
809
Exercises
810
Amino Acid Metabolism
817
An Overview of Metabolism and Biochemical Energy
818
Catabolism of Amino Acids: Deamination
822
The Urea Cycle
827
Catabolism of Amino Acids: The Carbon Chains
831
Biosynthesis of Amino Acids
838
Lagniappe: Visualizing Enzyme Structures
844
Summary
845
Exercises
846
Biomolecules: Carbohydrates
851
Classification of Carbohydrates
852
Depicting Carbohydrate Stereochemistry: Fischer Projections
853
D.L Sugars
858
Configurations of the Aldoses
859
Cyclic Structures of Monosaccharides: Anomers
862
Reactions of Monosaccharides
866
The Eight Essential Monosaccharides
872
Disaccharides
873
Polysaccharides and Their Synthesis
876
Cell-Surface Carbohydrates and Carbohydrate Vaccines
879
Lagniappe: Sweetness
880
Summary
881
Exercises
882
Carbohydrate Metabolism
891
Hydrolysis of Complex Carbohydrates
892
Catabolism of Glucose: Glycolysis
893
Conversion of Pyruvate to Acetyl CoA
901
The Citric Acid Cycle
905
Biosynthesis of Glucose: Gluconeogenesis
912
Lagniappe: Avian Flu
920
Summary
921
Exercises
921
Biomolecules: Lipids and Their Metabolism
927
Waxes, Fats, and Oils
928
Soap
931
Phospholipids
933
Catabolism of Triacylglycerols: The Fate of Glycerol
934
Catabolism of Triacylglycerols: b-Oxidation
937
Biosynthesis of Fatty Acids
943
Prostaglandins and Other Eicosanoids
948
Terpenoids
950

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