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ISBN-10 ‏ : ‎ 1305256662
ISBN-13 ‏ : ‎ 978-1305256668
Author: John E. McMurry

Renowned for its student-friendly writing style and fresh perspective, this fully updated Third Edition of John McMurry’s ORGANIC CHEMISTRY WITH BIOLOGICAL APPLICATIONS provides full coverage of the foundations of organic chemistry–enhanced by biological examples throughout. In addition, McMurry discusses the organic chemistry behind biological pathways. New problems, illustrations, and essays have been added. Media integration with OWL for Organic Chemistry, a customizable online learning system and assessment tool, reduces faculty workload, facilitates instruction, and helps students master concepts through tutorials, simulations, and algorithmically-generated homework questions.

Table of Content:

Ch 1: Structure and Bonding
1-1: Atomic Structure: The Nucleus
1-2: Atomic Structure: Orbitals
1-3: Atomic Structure: Electron Configurations
1-4: Development of Chemical Bonding Theory
1-5: Describing Chemical Bonds: Valence Bond Theory
1-6: sp3 Hybrid Orbitals and the Structure of Methane
1-7: sp3 Hybrid Orbitals and the Structure of Ethane
1-8: sp2 Hybrid Orbitals and the Structure of Ethylene
1-9: sp Hybrid Orbitals and the Structure of Acetylene
1-10: Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur
1-11: Describing Chemical Bonds: Molecular Orbital Theory
1-12: Drawing Chemical Structures
Summary
Ch 2: Polar Covalent Bonds; Acids and Bases
2-1: Polar Covalent Bonds: Electronegativity
2-2: Polar Covalent Bonds: Dipole Moments
2-3: Formal Charges
2-4: Resonance
2-5: Rules for Resonance Forms
2-6: Drawing Resonance Forms
2-7: Acids and Bases: The Bronsted-Lowry Definition
2-8: Acid and Base Strength
2-9: Predicting Acid-Base Reactions from pKa Values
2-10: Organic Acids and Organic Bases
2-11: Acids and Bases: The Lewis Definition
2-12: Noncovalent Interactions between Molecules
Summary
Ch 3: Organic Compounds: Alkanes and Their Stereochemistry
3-1: Functional Groups
3-2: Alkanes and Alkane Isomers
3-3: Alkyl Groups
3-4: Naming Alkanes
3-5: Properties of Alkanes
3-6: Conformations of Ethane
3-7: Conformations of Other Alkanes
Summary
Ch 4: Organic Compounds: Cycloalkanes and Their Stereochemistry
4-1: Naming Cycloalkanes
4-2: Cis-Trans Isomerism in Cycloalkanes
4-3: Stability of Cycloalkanes: Ring Strain
4-4: Conformations of Cycloalkanes
4-5: Conformations of Cyclohexane
4-6: Axial and Equatorial Bonds in Cyclohexane
4-7: Conformations of Monosubstituted Cyclohexanes
4-8: Conformations of Disubstituted Cyclohexanes
4-9: Conformations of Polycyclic Molecules
Summary
Ch 5: Stereochemistry at Tetrahedral Centers
5-1: Enantiomers and the Tetrahedral Carbon
5-2: The Reason for Handedness in Molecules: Chirality
5-3: Optical Activity
5-4: Pasteur’s Discovery of Enantiomers
5-5: Sequence Rules for Specifying Configuration
5-6: Diastereomers
5-7: Meso Compounds
5-8: Racemic Mixtures and the Resolution of Enantiomers
5-9: A Review of Isomerism
5-10: Chirality at Nitrogen, Phosphorus, and Sulfur
5-11: Prochirality
5-12: Chirality in Nature and Chiral Environments
Summary
Ch 6: An Overview of Organic Reactions
6-1: Kinds of Organic Reactions
6-2: How Organic Reactions Occur: Mechanisms
6-3: Radical Reactions
6-4: Polar Reactions
6-5: An Example of a Polar Reaction: Addition of H2O to Ethylene
6-6: Using Curved Arrows in Polar Reaction Mechanisms
6-7: Describing a Reaction: Equilibria, Rates, and Energy Changes
6-8: Describing a Reaction: Bond Dissociation Energies
6-9: Describing a Reaction: Energy Diagrams and Transition States
6-10: Describing a Reaction: Intermediates
6-11: A Comparison between Biological Reactions and Laboratory Reactions
Summary
Ch 7: Alkenes and Alkynes
7-1: Calculating the Degree of Unsaturation
7-2: Naming Alkenes and Alkynes
7-3: Cis-Trans Isomerism in Alkenes
7-4: Alkene Stereochemistry and the E,Z Designation
7-5: Stability of Alkenes
7-6: Electrophilic Addition Reactions of Alkenes
7-7: Orientation of Electrophilic Addition: Markovnikov’s Rule
7-8: Carbocation Structure and Stability
7-9: The Hammond Postulate
7-10: Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements
Summary
Ch 8: Reactions of Alkenes and Alkynes
8-1: Preparing Alkenes: A Preview of Elimination Reactions
8-2: Halogenation of Alkenes
8-3: Halohydrins from Alkenes
8-4: Hydration of Alkenes
8-5: Reduction of Alkenes: Hydrogenation
8-6: Oxidation of Alkenes: Epoxidation
8-7: Oxidation of Alkenes: Hydroxylation
8-8: Oxidation of Alkenes: Cleavage to Carbonyl Compounds
8-9: Addition of Carbenes to Alkenes: Cyclopropane Synthesis
8-10: Radical Additions to Alkenes: Chain-Growth Polymers
8-11: Biological Additions of Radicals to Alkenes
8-12: Conjugated Dienes
8-13: Reactions of Conjugated Dienes
8-14: The Diels-Alder Cycloaddition Reaction
8-15: Reactions of Alkynes
Summary
Ch 9: Aromatic Compounds
9-1: Naming Aromatic Compounds
9-2: Structure and Stability of Benzene
9-3: Aromaticity and the Huckel 4n + 2 Rule
9-4: Aromatic Ions and Aromatic Heterocycles
9-5: Polycyclic Aromatic Compounds
9-6: Reactions of Aromatic Compounds: Electrophilic Substitution
9-7: Alkylation and Acylation of Aromatic Rings: The Friedel-Crafts Reaction
9-8: Substituent Effects in Electrophilic Substitutions
9-9: Nucleophilic Aromatic Substitution
9-10: Oxidation and Reduction of Aromatic Compounds
9-11: An Introduction to Organic Synthesis: Polysubstituted Benzenes
Summary
Ch 10: Structure Determination: Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet Spectrosco
10-1: Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments
10-2: Interpreting Mass Spectra
10-3: Mass Spectrometry of Some Common Functional Groups
10-4: Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments
10-5: Spectroscopy and the Electromagnetic Spectrum
10-6: Infrared Spectroscopy
10-7: Interpreting Infrared Spectra
10-8: Infrared Spectra of Some Common Functional Groups
10-9: Ultraviolet Spectroscopy
10-10: Interpreting Ultraviolet Spectra: The Effect of Conjugation
10-11: Conjugation, Color, and the Chemistry of Vision
Summary
Ch 11: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
11-1: Nuclear Magnetic Resonance Spectroscopy
11-2: The Nature of NMR Absorptions
11-3: Chemical Shifts
11-4: 13C NMR Spectroscopy: Signal Averaging and FT-NMR
11-5: Characteristics of 13C NMR Spectroscopy
11-6: DEPT 13C NMR Spectroscopy
11-7: Uses of 13C NMR Spectroscopy
11-8: 1H NMR Spectroscopy and Proton Equivalence
11-9: Chemical Shifts in 1H NMR Spectroscopy
11-10: Integration of 1H NMR Absorptions: Proton Counting
11-11: Spin-Spin Splitting in 1H NMR Spectra
11-12: More Complex Spin-Spin Splitting Patterns
11-13: Uses of 1H NMR Spectroscopy
Summary
Ch 12: Organohalides: Nucleophilic Substitutions and Eliminations
12-1: Names and Structures of Alkyl Halides
12-2: Preparing Alkyl Halides from Alkenes: Allylic Bromination
12-3: Preparing Alkyl Halides from Alcohols
12-4: Reactions of Alkyl Halides: Grignard Reagents
12-5: Organometallic Coupling Reactions
12-6: Discovery of the Nucleophilic Substitution Reaction
12-7: The SN2 Reaction
12-8: Characteristics of the SN2 Reaction
12-9: The SN1 Reaction
12-10: Characteristics of the SN1 Reaction
12-11: Biological Substitution Reactions
12-12: Elimination Reactions: Zaitsev’s Rule
12-13: The E2 Reaction and the Deuterium Isotope Effect
12-14: The E1 and E1cB Reactions
12-15: Biological Elimination Reactions
12-16: A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2
Summary
Ch 13: Alcohols, Phenols, and Thiols; Ethers and Sulfides
13-1: Naming Alcohols, Phenols, and Thiols
13-2: Properties of Alcohols, Phenols, and Thiols
13-3: Preparing Alcohols from Carbonyl Compounds
13-4: Reactions of Alcohols
13-5: Oxidation of Alcohols and Phenols
13-6: Protection of Alcohols
13-7: Preparation and Reactions of Thiols
13-8: Ethers and Sulfides
13-9: Preparing Ethers
13-10: Reactions of Ethers
13-11: Crown Ethers and Ionophores
13-12: Preparation and Reactions of Sulfides
13-13: Spectroscopy of Alcohols, Phenols, and Ethers
Summary
A Preview of Carbonyl Chemistry
Ch 14: Aldehydes and Ketones: Nucleophilic Addition Reactions
14-1: Naming Aldehydes and Ketones
14-2: Preparing Aldehydes and Ketones
14-3: Oxidation of Aldehydes
14-4: Nucleophilic Addition Reactions of Aldehydes and Ketones
14-5: Nucleophilic Addition of H2O: Hydration
14-6: Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation
14-7: Nucleophilic Addition of Amines: Imine and Enamine Formation
14-8: Nucleophilic Addition of Alcohols: Acetal Formation
14-9: Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction
14-10: Biological Reductions
14-11: Conjugate Nucleophilic Addition to a,B-Unsaturated Aldehydes and Ketones
14-12: Spectroscopy of Aldehydes and Ketones
Summary
Ch 15: Carboxylic Acids and Nitriles
15-1: Naming Carboxylic Acids and Nitriles
15-2: Structure and Properties of Carboxylic Acids
15-3: Biological Acids and the Henderson-Hasselbalch Equation
15-4: Substituent Effects on Acidity
15-5: Preparing Carboxylic Acids
15-6: Reactions of Carboxylic Acids: An Overview
15-7: Chemistry of Nitriles
15-8: Spectroscopy of Carboxylic Acids and Nitriles
Summary
Ch 16: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
16-1: Naming Carboxylic Acid Derivatives
16-2: Nucleophilic Acyl Substitution Reactions
16-3: Reactions of Carboxylic Acids
16-4: Reactions of Acid Halides
16-5: Reactions of Acid Anhydrides
16-6: Reactions of Esters
16-7: Reactions of Amides
16-8: Reactions of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives
16-9: Polyamides and Polyesters: Step-Growth Polymers
16-10: Spectroscopy of Carboxylic Acid Derivatives
Summary
Ch 17: Carbonyl Alpha-Substitution and Condensation Reactions
17-1: Keto-Enol Tautomerism
17-2: Reactivity of Enols: a-Substitution Reactions
17-3: Alpha Bromination of Carboxylic Acids
17-4: Acidity of a Hydrogen Atoms: Enolate Ion Formation
17-5: Alkylation of Enolate Ions
17-6: Carbonyl Condensations: The Aldol Reaction
17-7: Dehydration of Aldol Products
17-8: Intramolecular Aldol Reactions
17-9: The Claisen Condensation Reaction
17-10: Intramolecular Claisen Condensations: The Dieckmann Cyclization
17-11: Conjugate Carbonyl Additions: The Michael Reaction
17-12: Carbonyl Condensations with Enamines: The Stork Reaction
17-13: Biological Carbonyl Condensation Reactions
Summary
Ch 18: Amines and Heterocycles
18-1: Naming Amines
18-2: Properties of Amines
18-3: Basicity of Amines
18-4: Basicity of Arylamines
18-5: Biological Amines and the Henderson-Hasselbalch Equation
18-6: Synthesis of Amines
18-7: Reactions of Amines
18-8: Heterocyclic Amines
18-9: Fused-Ring Heterocycles
18-10: Spectroscopy of Amines
Summary
Ch 19: Biomolecules: Amino Acids, Peptides, and Proteins
19-1: Structures of Amino Acids
19-2: Amino Acids and the Henderson-Hasselbalch Equation: Isoelectric Points
19-3: Synthesis of Amino Acids
19-4: Peptides and Proteins
19-5: Amino Acid Analysis of Peptides
19-6: Peptide Sequencing: The Edman Degradation
19-7: Peptide Synthesis
19-8: Protein Structure
19-9: Enzymes and Coenzymes
19-10: How Do Enzymes Work? Citrate Synthase
Summary
Ch 20: Amino Acid Metabolism
20-1: An Overview of Metabolism and Biochemical Energy
20-2: Catabolism of Amino Acids: Deamination
20-3: The Urea Cycle
20-4: Catabolism of Amino Acids: The Carbon Chains
20-5: Biosynthesis of Amino Acids
Summary
Ch 21: Biomolecules: Carbohydrates
21-1: Classifying Carbohydrates
21-2: Representing Carbohydrate Stereochemistry: Fischer Projections
21-3: D,L Sugars
21-4: Configurations of the Aldoses
21-5: Cyclic Structures of Monosaccharides: Anomers
21-6: Reactions of Monosaccharides
21-7: The Eight Essential Monosaccharides
21-8: Disaccharides
21-9: Polysaccharides and Their Synthesis
21-10: Some Other Important Carbohydrates
Summary
Ch 22: Carbohydrate Metabolism
22-1: Hydrolysis of Complex Carbohydrates
22-2: Catabolism of Glucose: Glycolysis
22-3: Conversion of Pyruvate to Acetyl CoA
22-4: The Citric Acid Cycle
22-5: Biosynthesis of Glucose: Gluconeogenesis
Summary
Ch 23: Biomolecules: Lipids and Their Metabolism
23-1: Waxes, Fats, and Oils
23-2: Soap
23-3: Phospholipids
23-4: Catabolism of Triacylglycerols: The Fate of Glycerol
23-5: Catabolism of Triacylglycerols: B-Oxidation
23-6: Biosynthesis of Fatty Acids
23-7: Prostaglandins and Other Eicosanoids
23-8: Terpenoids
23-9: Steroids
23-10: Biosynthesis of Steroids
23-11: Some Final Comments on Metabolism
Summary
Ch 24: Biomolecules: Nucleic Acids and Their Metabolism
24-1: Nucleotides and Nucleic Acids
24-2: Base Pairing in DNA: The Watson-Crick Model
24-3: Replication of DNA
24-4: Transcription of DNA
24-5: Translation of RNA: Protein Biosynthesis
24-6: DNA Sequencing
24-7: DNA Synthesis
24-8: The Polymerase Chain Reaction
24-9: Catabolism of Nucleotides
24-10: Biosynthesis of Nucleotides
Summary
Ch e25: Secondary Metabolites: An Introduction to Natural Products Chemistry
25-1: Classifying Natural Products
25-2: Biosynthesis of Pyridoxal Phosphate
25-3: Biosynthesis of Morphine
25-4: Biosynthesis of Erythromycin
Summary
Ch e26: Orbitals and Organic Chemistry: Pericyclic Reactions
26-1: Molecular Orbitals of Conjugated Pi Systems
26-2: Electrocyclic Reactions
26-3: Stereochemistry of Thermal Electrocyclic Reactions
26-4: Photochemical Electrocyclic Reactions
26-5: Cycloaddition Reactions
26-6: Stereochemistry of Cycloadditions
26-7: Sigmatropic Rearrangements
26-8: Some Examples of Sigmatropic Rearrangements
26-9: A Summary of Rules for Pericyclic Reactions
Summary
Ch e27: Synthetic Polymers
27-1: Chain-Growth Polymers
27-2: Stereochemistry of Polymerization: Ziegler-Natta Catalysts
27-3: Copolymers
27-4: Step-Growth Polymers
27-5: Olefin Metathesis Polymerization
27-6: Polymer Structure and Physical Properties
Summary
Appendix A: Nomenclature of Polyfunctional Organic Compounds
Appendix B: Acidity Constants for Some Organic Compounds
Appendix C: Glossary
Appendix D: Answers to In-Text Problems
Index