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Brown W.H., Foote C.S., Iverson B.L., Anslyn E.V. Organic Chemistry

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Brown W.H., Foote C.S., Iverson B.L., Anslyn E.V. Organic Chemistry
5th Enhanced Edition. — Brooks/Cole Cengage Learning, 2011. — 1254 p. — ISBN-13: 978-0-538-49675-9. — ISBN-10: 0-538-49675-4.
Featuring a revolutionary new approach to teaching mechanisms that will lead your students to an immediate understanding of each new reaction, this Enhanced Fifth Edition of ORGANIC CHEMISTRY offers numerous biological examples and applied problems, increased coverage of bioorganic chemistry, expanded in-text learning tools, a new Appendix that shows students how to overcome typical mistakes in arrow pushing, and a new e-book. In addition, the Enhanced Edition is fully integrated with OWL for Organic Chemistry, the #1 online learning system for chemistry.
Ideal for students majoring in chemistry as well as in the health and biological sciences, the Enhanced Fifth Edition builds upon the text's hallmarks of unified mechanistic themes, focused problem-solving, use of applied problems from the pharmaceutical field, challenging synthesis problems and medicinal chemistry problems, and unrivaled visuals. To reflect the latest developments from the field, the book now covers the organic chemistry of sulfur and phosphorus. The book's revolutionary approach to teaching mechanisms begins in Chapter 6, with detailed explanations of mechanism elements, including when they are appropriate to use. From then on, reaction mechanisms are described as combinations of these individual mechanism elements. Throughout the book, reaction mechanisms are offset in a clear, stepwise fashion, and similarities between related mechanisms are emphasized.
Covalent bonding and shapes of molecules
Electronic Structure of Atoms
Lewis Model of Bonding
How To Draw Lewis Structures from Condensed Structural Formulas
Functional Groups
Bond Angles and Shapes of Molecules
Chemical Connections. Fullerene - A New Form of Carbon
Polar and Nonpolar Molecules
Quantum or Wave Mechanics
A Combined Valence Bond and Molecular Orbital Theory Approach to Covalent Bonding
Resonance
How To Draw Curved Arrows and Push Electrons in Creating Contributing Structures
Molecular Orbitals for Delocalized Systems
Bond Lengths and Bond Strengths in Alkanes, Alkenes, and Alkynes
Summary
Problems
Alkanes and cycloalkanes
The Structure of Alkanes
Constitutional Isomerism in Alkanes
Nomenclature of Alkanes and the IUPAC System
Cycloalkanes
Conformations of Alkanes and Cycloalkanes
How To Draw Alternative Chair Conformations of Cyclohexane
Cis,Trans - Isomerism in Cycloalkanes and Bicycloalkanes
How To Convert Planar Cyclohexanes to Chair Cyclohexanes
Chemical Connections The Poisonous Puffer Fish
Physical Properties of Alkanes and Cycloalkanes
Reactions of Alkanes
Sources and Importance of Alkanes
Chemical Connections Octane Rating: What Those Numbers at the Pump Mean
Summary
Problems
Stereochemistry and chirality
Stereoisomerism
Chirality - The Handedness of Molecules
How To Draw Chiral Molecules
Naming Chiral Centers - The R,S - Systems
How To Assign R or S Confi guration to a Chiral Center
Acyclic Molecules with Two or More Chiral Centers
Cyclic Molecules with Two or More Chiral Centers
Properties of Stereoismers
Optical Activity - How Chirality Is Detected in the Laboratory
The Signifi cance of Chirality in the Biological World
Connections to Biological Chemistry Chiral Drugs
Connections to Biological Chemistry Amino Acids
Separation of Enantiomers - Resolution
Summary
Problems
Acids and bases
Arrhenius Acids and Bases
Brinsted-Lowry Acids and Bases
Acid Dissociation Constants, pKa, and Strengths of Acids and Bases
The Position of Equilibrium in Acid-Base Reactions
How To Calculate Equilibrium Constants for Acid-Base Reactions
Connections to Biological Chemistry The Ionization of Functional Groups at Physiological pH
Thermochemistry and Mechanism of Acid-Base Reactions
Molecular Structure and Acidity
Lewis Acids and Bases
Summary
Problems
[bAlkenes[/b]
Structure of Alkenes
How To Calculate the Index of Hydrogen Defi ciency
Nomenclature of Alkenes
Physical Properties of Alkenes
Chemical Connections The Case of the Iowa and New York Strains of the European Corn Borer
Naturally Occurring Alkenes - Terpene Hydrocarbons
Connections to Biological Chemistry The Importance of Cis Double Bonds in Fats Versus Oils
Summary
Problems
Reactions of alkenes
Reactions of Alkenes - An Overview
Organic Reactions Involving Reactive Intermediates
Electrophilic Additions
Hydroboration-Oxidation
How To Write a Balanced Half-Reaction
Oxidation
Reduction
Connections to Biological Chemistry Trans Fatty Acids: What They Are and How To Avoid Them
Molecules Containing Chiral Centers as Reactants or Products
Summary
Problems
Alkynes
Structure of Alkynes
Nomenclature of Alkynes
Physical Properties of Alkynes
Acidity of Alkynes
Preparation of Alkynes
Electrophilic Addition to Alkynes
Hydration of Alkynes to Aldehydes and Ketones
Reduction of Alkynes
Organic Synthesis
Summary
Problems
Haloalkanes, halogenation, and radical reactions
Structure
Nomenclature
Physical Properties of Haloalkanes
Preparation of Haloalkanes by Halogenation of Alkanes
Mechanism of Halogenation of Alkanes
Chemical Connections Freons
Allylic Halogenation
Radical Autoxidation
Connections to Biological Chemistry Antioxidants
Radical Addition of HBr to Alkenes
Summary
Problems
Nucleophilic substitution and β-elimination
Nucleophilic Substitution in Haloalkanes
Mechanisms of Nucleophilic Substitution
Experimental Evidence for SN and SN Mechanisms
Analysis of Several Nucleophilic Substitution Reactions
β-Elimination
Mechanisms of β-Elimination
Experimental Evidence for E1 and E2 Mechanisms
Substitution Versus Elimination
Neighboring Group Participation
Connections to Biological Chemistry Mustard Gases and the Treatment of Neoplastic Diseases
Summary
Problems
Alcohols
Structure and Nomenclature of Alcohols
Physical Properties of Alcohols
Connections to Biological Chemistry The Importance of Hydrogen Bonding in Drug Receptor Interactions
Acidity and Basicity of Alcohols
Reaction of Alcohols with Active Metals
Conversion of Alcohols to Haloalkanes and Sulfonates
Acid-Catalyzed Dehydration of Alcohols
The Pinacol Rearrangement
Oxidation of Alcohols
Chemical Connections Blood Alcohol Screening
Connections to Biological Chemistry The Oxidation of Alcohols by NAD+
Thiols
Summary
Problems
Ethers, sulfides, and epoxides
Structure of Ethers
Nomenclature of Ethers
Physical Properties of Ethers
Preparation of Ethers
Reactions of Ethers
Silyl Ethers as Protecting Groups
Epoxides: Structure and Nomenclature
Synthesis of Epoxides
Reactions of Epoxides
Ethylene Oxide and Epichlorohydrin: Building Blocks in Organic Synthesis
Crown Ethers
Sulfides
Summary
Problems
Infrared spectroscopy
Electromagnetic Radiation
Molecular Spectroscopy
Infrared Spectroscopy
Interpreting Infrared Spectra
Solving Infrared Spectral Problems
Summary
Problems
Nuclear magnetic resonance spectroscopy
Nuclear Spin States
Orientation of Nuclear Spins in an Applied Magnetic Field
Nuclear Magnetic Resonance
An NMR Spectrometer
Equivalent Hydrogens
Signal Areas
Chemical Shift
Signal Splitting and the (n+1) Rule
The Origins of Signal Splitting
Stereochemistry and Topicity
Chemical Connections Magnetic Resonance Imaging
13C-NMR
Interpretation of NMR Spectra
How To Solve NMR Spectral Problems
Summary
Problems
Mass spectrometry
A Mass Spectrometer
Features of a Mass Spectrum
Interpreting Mass Spectra
Connections to Biological Chemistry Mass Spectrometry of Biological Macromolecules
Mass Spectrometry in the Organic Synthesis Laboratory and Other Applications
Summary
Problems
Introduction to organometallic compounds
Organomagnesium and Organolithium Compounds
Lithium Diorganocopper (Gilman) Reagents
Carbenes and Carbenoids
Summary
Problems
Aldehydes and ketones
Structure and Bonding
Nomenclature
Physical Properties
Reactions
Addition of Carbon Nucleophiles
The Wittig Reaction
Addition of Oxygen Nucleophiles
Addition of Nitrogen Nucleophiles
Keto-Enol Tautomerism
Connections to Biological Chemistry Pyridoxine (Vitamin B), a Carrier of Amino Groups
Oxidation
Reduction
Connections to Biological Chemistry NADH: The Biological Equivalent of a Hydride Reducing Agent
Reactions at an α-Carbon
Summary
Problems
Carboxylic acids
Structure
Nomenclature
Physical Properties
Chemical Connections From Willow Bark to Aspirin and Beyond
Acidity
Preparation of Carboxylic Acids
Reduction
Esterification
Chemical Connections The Pyrethrins: Natural Insecticides of Plant Origin
Chemical Connections Esters as Flavoring Agents
Conversion to Acid Chlorides
Decarboxylation
Connections to Biological Chemistry Ketone Bodies and Diabetes Mellitus
Summary
Problems
Functional derivatives of carboxylic acids
Structure and Nomenclature
Chemical Connections From Cocaine to Procaine and Beyond
Chemical Connections From Moldy Clover to a Blood Thinner
Chemical Connections The Penicillins and Cephalosporins: β-Lactam Antibiotics
Connections to Biological Chemistry The Unique Structure of Amide Bonds
Acidity of Amides, Imides, and Sulfonamides
Characteristics of Reactions
Reaction with Water: Hydrolysis
Reaction with Alcohols
Reactions with Ammonia and Amines
Reaction of Acid Chlorides with Salts of Carboxylic Acids
Interconversion of Functional Derivatives
Reactions with Organometallic Compounds
How To Write Mechanisms for Interconversions of Carboxylic Acid Derivatives
Reduction
Summary
Problems
Enolate anions and enamines
Formation and Reactions of Enolate Anions: An Overview
Aldol Reaction
Claisen and Dieckmann Condensations
Claisen and Aldol Condensations in the Biological World
Chemical Connections Drugs that Lower Plasma Levels of Cholesterol
Enamines
Acetoacetic Ester Synthesis
Malonic Ester Synthesis
Chemical Connections Ibuprofen: The Evolution of an Industrial Synthesis
Conjugate Addition to α,β-Unsaturated Carbonyl
Compounds
Crossed Enolate Reactions using LDA
Summary
Problems
Conjugated systems
Stability of Conjugated Dienes
Electrophilic Addition to Conjugated Dienes
UV-Visible Spectroscopy
Chemical Connections Curry and Cancer
Summary
Problems
Benzene and the concept of aromaticity
The Structure of Benzene
The Concept of Aromaticity
Nomenclature
Chemical Connections Carcinogenic Polynuclear Aromatic Hydrocarbons and Smoking
Phenols
Chemical Connections Capsaicin, for Those Who Like It Hot
Reactions at a Benzylic Position
Summary
Problems
Reactions of benzene and its derivatives
Electrophilic Aromatic Substitution
Disubstitution and Polysubstitution
Nucleophilic Aromatic Substitution
Summary
Problems
Amines
Structure and Classifi cation
Nomenclature
Chirality of Amines and Quaternary Ammonium Ions
Physical Properties
Chemical Connections The Poison Dart Frogs of South America
Basicity
Connections to Biological Chemistry The Planarity of -NH Groups on Aromatic Rings
Reactions with Acids
Preparation
Reaction with Nitrous Acid
Hofmann Elimination
Cope Elimination
Summary
Problems
Carbon-carbon bond formation and synthesis
Carbon-Carbon Bond-Forming Reactions from
Earlier Chapters
Organometallic Compounds
Organopalladium Reagents - The Heck Reaction
Organopalladium Reagents - The Suzuki Coupling
Alkene Metathesis
The Diels-Alder Reaction
Pericyclic Reactions and Transition State Aromaticity
Chemical Connections Singlet Oxygen
Contents The Synthesis of Enantiomerically Pure Target Molecules
Summary
Problems
Carbohydrates
Monosaccharides
The Cyclic Structure of Monosaccharides
Chemical Connections L-Ascorbic Acid (Vitamin C)
Reactions of Monosaccharides
Chemical Connections Testing for Glucose
Disaccharides and Oligosaccharides
Chemical Connections A, B, AB, and O Blood Group Substances
Polysaccharides
Chemical Connections High-Fructose Corn Syrup
Glucosaminoglycans
Summary
Problems
Lipids
Triglycerides
Soaps and Detergents
Connections to Biological Chemistry FAD/FADH: Agents for Electron Transfer in Biological Oxidation-Reductions, Fatty Acid Oxidation
Prostaglandins
Steroids
Chemical Connections Drugs that Lower Plasma Levels of Cholesterol
Phospholipids
Chemical Connections Snake Venom Phospholipases
Fat-Soluble Vitamins
Chemical Connections Vitamin K, Blood Clotting, and Basicity
Summary
Problems
Amino acids and proteins
Amino Acids
Acid-Base Properties of Amino Acids
Polypeptides and Proteins
Primary Structure of Polypeptides and Proteins
Synthesis of Polypeptides
Three-Dimensional Shapes of Polypeptides and Proteins
Chemical Connections Spider Silk
Summary
Problems
Nucleic acids
Nucleosides and Nucleotides
The Structure of DNA
Chemical Connections The Search for Antiviral Drugs
Ribonucleic Acids
Chemical Connections The Fountain of Youth
The Genetic Code
Sequencing Nucleic Acids
Chemical Connections DNA Fingerprinting
Summary
Problems
Organic polymer chemistry
The Architecture of Polymers
Polymer Notation and Nomenclature
Molecular Weights of Polymers
Polymer Morphology - Crystalline Versus
Amorphous Materials
Step-Growth Polymerizations
Chemical Connections Stitches That Dissolve
Chain-Growth Polymerizations
Chemical Connections Organic Polymers That Conduct Electricity
Chemical Connections The Chemistry of Superglue
Chemical Connections Recycling of Plastics
Summary
Problems
Appendices
Thermodynamics and the Equilibrium Constant
Major Classes of Organic Acids
Bond Dissociation Enthalpies
Characteristic 1H-NMR Chemical Shifts
Characteristic 13C-NMR Chemical Shifts
Characteristic IR Absorption Frequencies
Electrostatic Potential Maps
Summary of Stereochemical Terms
Summary of the Rules of Nomenclature
Common Mistakes in Arrow Pushing
Glossary
Index
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