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Organic Chemistry,9780131963283
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Organic Chemistry

by
ISBN13:

9780131963283

ISBN10:
0131963287
Format:
Paperback
Pub. Date:
7/5/2006
Publisher(s):
Pearson College Div
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Summary

This Study Guide and Solutions Manual contains complete and detailed explanations of the solutions to the problems in the text. In addition, youll find a section on advanced acid/base chemistry with an additional set of problems, an 18-page tutorial on pushing electrons, exercises on building molecular models and calculating kinetic parameters, as well as 23 practice tests.

Table of Contents

An Introduction To The Study Of Organic Chemistry
Electronic Structure and Bonding Acids and Bases
The Structure of an Atom
The Distribution of Electrons in an Atom
Ionic, Covalent, and Polar Bonds
Representation of a Structure
Atomic Orbitals
An Introduction to Molecular Orbital Theory
Bonding in Methane and Ethane: Single Bonds
Bonding in Ethane: A Double Bond
Bonding in Ethyne: A Triple Bond
Bonding in the Methyl Cation, the Methyl Radical, and the Methyl Anion
Bonding in Water
Bonding in Ammonia and the Ammonium Ion
Bonding in the Hydrogen Halides
Summary: Orbital Hybridization, Bond Lengths, Bond Strengths, and Bond Angles
Dipole Moments of Molecules
An Introduction to Acids and Bases
Organic Acids and Bases pK
A and pH
The Effect of Structure on pK
A An Introduction to Delocalized Electrons and Resonance
The Effect of pH on the Structure of an Organic Compound
Lewis Acids and Bases
An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure
Nomenclature of Alkyl Substituents
Nomenclature of Alkanes
Nomenclature of Cycloalkanes
Nomenclature of Alkyl Halides
Nomenclature of Ethers
Nomenclature of Alcohols
Nomenclature of Amines
Structures of Alkyl Halides, Alcohols, Ethers, and Amines
Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines
Conformations of Alkanes: Rotation About Carbon-Carbon Bonds
Cycloalkanes: Ring Strain
Conformations of Cyclohexane
Conformations of Monosubstituted Cyclohexanes
Conformations of Disubstituted Cyclohexanes
Conformations of Fused Rings
Hydrocarbons, Stereochemistry, And Resonance
Alkenes: Structure, Nomenclature, and an Introduction to Reactivity Thermodynamics and Kinetics
Molecular Formula and the Degree of Unsaturation
Nomenclature of Alkenes
The Structure of Alkenes
Cis- Trans Isomerism
The E,Z
System of Nomenclature
How Alkenes React
Curved Arrows
Thermodynamics and Kinetics
Reactions of Alkenes
Addition of Hydrogen Halides
Carbocation Stability
The Structure of the Transition State
Regioselectivity of Electophilic Addition Reactions
Addition of Water and Addition of Alcohols
Rearrangement of Carbocations
Addition of Halogens
Oxymercuration-Reduction and Alkoxymercuration-Reduction
Addition of Borane: Hydroboration-Oxidation
Addition of Radicals
The Relative Stabilities of Radicals
Addition of Hydrogen
The Relative Stabilities of Alkenes
Reactions and Synthesis
Stereochemistry: The Arrangement of Atoms in Space
The Stereochemistry of Addition Reactions
Cis-Trans Isomers
Chirality
Asymmetric Carbon, Chirality Centers, and Stereocenters
Isomers with One Asymmetric Carbon
Drawing Enantiomers
Naming Enantiomers: The R, S
System of Nomenclature
Optical Activity
Optical Purity and Enantiomeric Excess
Isomers with More Than One Asymmetric Carbon
Meso Compounds
The R, S
System of Nomenclature for Isomers with More Than One Asymmetric Carbon
Reactions of Compounds that Contain an Asymmetric Carbon
The Absolute Configuration of (+)- Glyceraldehyde
Separating Enantiomers
Discrimination of Enantiomers by Biological Molecules
Enantiotopic Hydrogens, Diastereotopic Hydrogens, and Prochiral Carbons
Nitrogen and Phosphorus Asymmetric Carbons
Stereochemistry of Reactions: Regioselective, Stereoselective, and Stereospecific Reactions
Stereochemistry of Electrophilic Addition Reactions of Alkenes
Stereochemistry of Enzyme-Catalyzed Reactions
Reactions of Alkynes Introduction to Multistep Synthesis
Nomenclature of Alkynes
Physical Properties of Unsaturated Hydrocarbons
The Structure of Alkynes
How Alkynes React
Addition of Hydrogen Halides and Addition of Halogens
Addition of Water
Addition of Borane: Hydroboration-Oxidation
Addition of Hydrogen
Acidity of a Hydrogen Bonded to an SP
Hybridized Carbon
Synthesis Using Acetylide Ions
Designing a Synthesis I: An Introduction to Multistep Synthesis
Commercial Use of Ethyne
Electron Delocalization and Resonance More About Molecular Orbital Theory
Delocalized Electrons: the Structure of Benzene
The Bonding In Benzene
Resonance Contributors and the Resonance Hybrid
Drawing Resonance Contributors
Predicted Stabilites of Resonance Contributors
Resonance Energy
Stability of Allylic and Benzylic Cations
Stability of Allylic and Benzylic Radicals
Some Chemical Consequences of Electron Delocalization
The Effect of Electron Delocalization on pK
A Molecular Orbital Description of Stability
Reactions of Dienes Ultraviolet/Visible Spectroscopy
Nomenclature of Alkenes with More than One Functional Group
Configurational Isomers of Dienes
Relative Stabilities of Dienes
How Dienes React
Electrophilic Addition Reactions of Isolated Dienes
Electrophilic Addition Reactions of Conjugated Dienes
Thermodynamic Versus Kinetic Control of Reactions
The Diels-Alder Reaction: A 1,4-Addition Reaction
Ultraviolet and Visible Spectroscopy
The Beer-Lambert Law
Effect of Conjugation on Imax
The Visible Spectrum and Color
Uses of UV/VIS Spectroscopy
Substitution And Elimination Reactions
Reactions of Alkanes: Radicals
The Low Reactivity of Alkanes
Chlorination and Bromination of Alkanes
Factors that Determine Product Distribution
The Reactivity-Selectivity Principle
Radical Substitution of Benzylic and Allylic Hydrogens
Stereochemistry of Radical Substitution Reactions
Reactions of Cyclic Compounds
Radicals Reactions in Biological Systems
Radicals and Stratospheric Ozone
Substitution Reactions of Alkyl Halides
Reactivity Considerations
The Mechanism of SN2 Reactions
The SN2 Reaction
The Reversibility of an SN2 Reaction
The Mechanism of SN1 Reaction
The SN1 Reaction
The Stereochemistry of SN2 and SN1 Reactions
Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides
Competition Between SN2 and SN1 Reactions
The Role of the Solvent in SN1 and SN1 Reactions
Biological Methylating Reagents
Elimination Reactions of Alkyl Halides
Competition Between Substitution and Elimination
The E2 Reaction
The Regioselectivity of the E2 Reaction
The E1 Reaction
Competition Between E2 and E1 Reactions
Stereochemistry of E2 and E1 Reactions
Elimination from Cyclic Compounds
A Kinetic Isotope Effect
Competition Between Substitution and Elimination
Substitution and Elimination Reactions in Synthesis
Consecutive E2 Elimination Reactions
Intermolecular versus Intramolecular Reactions
Designing a Synthesis II: Approaching the Problem
Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds Organometallic Compounds
Substitution Reactions of Alcohol
Amines Do Not Undergo Substitution Reactions
Other Methods Used to Convert Alcohols Into Alkyl Halides
Converting Alcohols into Sulfonates
Dehydration of Alcohols
Substitution Reactions of Ethers
Reactions of Epoxides
Arene Oxides
Crown Ethers
Thiols, Sulfides, and Sulfonium Salts
Organometallic Compounds
Coupling Reactions
Identification Of Organic Compounds
Mass Spectrometry and Infrared Spectroscopy
Mass Spectrometry
The Mass Spectrum
Fragmentation
Isotopes in Mass Spectrometry
Determination of Molecular Formulas: High-Resolution Mass Spectrometry
Fragmentation at Functional Groups
Spectroscopy and the Electromagnetic Spectrum
Infrared Spectroscopy
Infrared Absorption Bands
Intensity of Absorption Bands
Position of Absorption Bands
C-H Absorption Bands
Shape of Absorption Bands
Absence of Absorption Bands
Infrared Inactive Vibrations
Identifying Infrared Spectra
NMR Spectroscopy
Introduction to NMR Spectroscopy
Fourier Transform NMR
Shielding
The Number of Signals in the 1H NMR Spectrum
The Chemical Shift
The Relative Position of 1H NMR Signals
Characteristic Values of Chemical Shifts
Integration of the NMR Signals
Diamagnetic Anisotropy
Splitting of the Signals
More Examples of 1H NMR Spectra
Coupling Constants
Splitting Diagrams
Time Dependence of NMR Spectroscopy
Protons Bonded to Oxygen and Nitrogen
Use of Deuterium in 1H NMR Spectroscopy
Resolution of 1H NMR Spectra
13C NMR Spectroscopy
DEPT 13C NMR Spectra
Two-Dimensional NMR Spectroscopy
Magnetic Resonance Imaging
Aromatic Compounds
Aromaticity Reactions of Benzene
Criteria for Aromaticity
Aromatic Hydrocarbons
Aromatic Heterocyclic Compounds
Some Chemical Consequences of Aromaticity
Antiaromaticity
A Molecular Orbital Description of Aromaticity and Antiaromaticity
Nomenclature of Monosubstituted Benzenes
How Benzene Reacts
General Mechanism for Electrophilic Aromatic Substitution Reactions
Halogenation of Benzene
Nitration of Benzene
Sulfonation of Benzene
Friedel-Crafts Alkylation of Benzene
Friedel-Crafts Alkylations of Benzene
Alkylations of Benzene by Acylation-Reduction
Reactions of Substituted Benzenes
Nomenclature of Diubstituted and Polysubstituted Benzenes
Reactions of Substituents on Benzene
The Effect of Substituents on Reactivity
The Effect of Substituents on Orientation
The Effect of Substituents on pK
The Ortho/Para Ratio
Additional Considerations Regarding Substituent Effects
Designing a Synthesis III: Synthesis of Monosubstituted and Disubstituted Benzenes
Synthesis of Trisubstituted Benzenes
Synthesis of Substituted Benzenes Using Arenediazonium Salts
The Arenediazonium Ion as an Electrophile
Mechanism for the Reaction of Amines with Nitrous Acid
Nucleophilic Aromatic Substitution Reactions
Benzyne
Polycyclic Benzenoid Hydrocarbons
Electrophilic Substitution Reactions of Naphthalene and Substituted Naphthalenes
Carbonyl Compounds
Carbonyl Compounds I: Nucleophilic Acyl Substitution
Nomenclature
Structures of Carboxylic Acids and Carboxylic Acid Derivatives
Physical Properties of Carbonyl Compounds
Naturally Occurring Carboxylic Acids and Carobxylic Acid Derivatives
How Class I Carbonyl Compounds React
Relative Reactivities of Carboxylic Acids, Acyl Halides, and Carboxylic Acid Derivatives
General Mechanism for Nucleophilic Acyl Substitution Reactions
Reactions of Acyl Halides
Reactions of Acid Anhydrides
Reactions of Esters
Acid-Catalyzed Ester Hydrolysis
Hydroxide-Ion-Promotes Ester Hydrolysis
Soaps, Detergents, and Micelles
Reactions of Carboxylic Acids
Reactions of Amides
Acid-Catalyzed Hydrolysis of Amides
Hydrolysis of an Imide- The Gabriel Synthesis
Hydrolysis of Nitriles
Designing a Synthesis IV: The Synthesis of Cyclic Compounds
Synthesis of Carboxylic Acid Derivatives
Dicarboxylic Acids and Their Derivatives
Carbonyl Compounds II: Nucleophilic Acyl Addition, Nucleophilic Acyl Substitution, and Nucleophilic Addition-Elimination Reactions of a, b-Unsaturated Carbonyl Compounds
Nomenclature
Relative Reactivities of Carbonyl Compounds
How Aldeyhdes and Ketones React
Reactions of Carbonyl Compounds with Carbon Nucleophiles
Reactions of Carbonyl Compounds with Hydride Ion
Reactions of Aldehydes and Ketones with Nitrogen Nucleophiles
Reactions of Aldehydes and Ketones with Oxygen Nucleophiles
Protecting Groups
Addition of Sulfur Nucleophiles
The Wittig Reaction
Stereochemistry of Nucleophilic Addition Reactions: Re and Si Faces
Designing a Synthesis V: The Synthesis of Cyclic Compounds
Nucleophilic Addition to -Unsaturated Aldehydes and Ketones: Direct Addition Versus Conjugate Addition
Nucleophilic Addition to a, b-Unsaturated Carboxylic Acid Derivatives
Enzyme-Catalyzed Additions to a, b-Unsaturated Carbonyl Compounds
Carbonyl Compounds III: Reactions at the a-Carbon
Acidity of a-Hydrogens
Keto-Enol Tautomerism
How Enols and Enolate Ions React
Halogenation of the a-Carbon of Aldehydes and Ketones
Halogenation of the a-Carbon of Carboxylic Acids: The Hell-Volhard-Zelinski Reaction
a-Halogenated Carbonyl Compounds in Synthesis
Using LDA to Form an Enolate
Alkylation of the a-Carbon of Carbonyl Compounds
Alkylation and Acylation of the a-Carbon via an Enamine Intermediate
Alkylation of the b-Carbon: The Michael Reaction
The Aldol Addition
Dehydration of Aldol Addition Products: Formation of a, b-Unsaturated Aldehydes and Ketones
The Mixed Aldol Addition
The Claisen Condensation
The Mixed Claisen Condensation
Intramolecular Condensation and Addition Reactions
Decarboxylation of 3-Oxocarboxylic Acids
The Malonic Ester Synthesis: Synthesis of Carboxylic Acids
The Acetoacetic Ester Synthesis: Synthesis of Methyl Ketones
Designing a Synthesis VI: Making New Carbon-Carbon Bonds
Reactions at the a-Carbon in Biological Systems
Bioorganic Compounds
More About Oxidation-Reduction Reactions
Reduction Reactions
Oxidation of Alcohols
Oxidation of Aldehydes and Ketones
Oxidation of Alkenes with Peroxyacids
Hydroxylation of Alkenes
Oxidative Cleavage of 1,2-Diols
Oxidative Cleavage of Alkenes: Ozonolysis
Oxidative Cleavage of Alkynes
Designing a Synthesis VII: Functional Group Interconversion
Biological Oxidation-Reduction Reactions
Oxidation of Hydroquinones/Reduction of Quinones
More about Amines Heterocyclic Compounds
More About Nomenclature
More About Acid-Base Properties
Amine Inversion
Synthesis of Amines
Reactions of Amines
Reactions of Quaternary Ammonium Compounds
Phase-Transfer Catalysis
Unsaturated Five-Membered-Ring Heterocycles
Unsaturated Six-Membered-Ring Heterocycles
Biologically Important Heterocycles
Carbohydrates
Classification of Carbohydrates
The D and L Notation
Configurations of the Aldoses
Configurations of the Ketoses
Redox Reactions of Monosaccharides
Osazone Formation
Chain Elongation: The Kiliani-Fischer Synthesis
Chain Shortening: The Ruff Degradation
Stereochemistry of Glucose: The Fischer Proof
Cyclic Structure of Monosaccharides: Hemiacetal Formation
Stability of Glucose
Acylation and Alkylation of Monosaccharides
Formation of Glycosides
The Anomeric Effect
Reducing and Nonreducing Sugars
Determination of Ring Size
Disaccharides
Polysaccharides
Some Naturally Occurring Products Derived from Carbohydrates
Carbohydrates on Cell Surfaces
Synthetic Sweeteners
Amino Acids, Peptides, and Proteins
Classification and Nomenclature of Amino Acids
Configuration of Amino Acids
Acid-Base Properties of Amino Acids
The Isoelectric Point
Separation of Amino Acids
Resolution of Racemic Mixtures of Amino Acids
Peptide Bonds and Disulfide Bonds
Some Interesting Peptides
Strategy of Peptide Bond Synthesis: N-Protection and C-Activation
Automated Peptide Synthesis
Protein Structure
Determining the Primary Structure of a Protein
Secondary Structure of Proteins
Tertiary Structure of Proteins
Quaternary Structure of Proteins
Protein Denaturation
Catalysis
Catalysis in Organic Reactions
Nucleophilic Catalysis
Acid Catalysis
Base Catalysis
Metal-Ion Catalysis
Intramolecular Reactions
Intramolecular Catalysis
Catalysis in Biological Reactions
Enzyme-Catalyzed Reactions
Catalytic Antibodies and Artificial Enzymes
The Organic Mechanisms of the Coenzymes Metabolism
Overall View of Metabolism
Niacin: The Vitamin Needed for Many Redox Reactions
Flavin Adenine Dinucleotide and Flavin Mononucleotide: Vitamin B2
Thiamine Pyrophosphate: Vitamin B1
Biotin: Vitamin H
Pyridoxal Phosphate: Vitamin B6
Coenzyme B12: Vitamin B12
Tetrahydrofolate: Folic Acid
Vitamin KH2: Vitamin K
Special Topics In Organic Chemistry
Lipids
Fatty Acids
Waxes
Fats and Oils
Membranes
Prostaglandins
Terpenes
Vitamin A
Biosynthesis of Terpenes
Steroids
Biosynthesis of Cholesterol
Synthetic Steroids
Nucleosides, Nucleotides, and Nucleic Acids I
Nucleosides and Nucleotides
ATP: The Carrier of Chemical Energy
Three Mechanisms for Phosphoryl Transfer Reactions
The "High-Energy" Character of Phosphoanhydride Bonds
Kinetic Stability of ATP in the Cell
Other Important Nucleotides
The Nucleic Acids
Helical Forms of DNA
Biosynthesis of DNA: Replication
Biosynthesis of Messenger RNA: Transcription
Ribosomal RNA
Transfer RNA
Biosynthesis of Proteins: Translation
Why DNA Contains Thymine Instead of Uracil
Determining the Base Sequence of DNA
Laboratory Synthesis of DNA Strands
Rational Drug Design
Synthetic Polymers
General Classes of Synthetic Polymers
Chain-Growth Polymers
Stereochemistry of Polymerization
Ziegler-Natta Catalysts
Polymerization of Dienes
The Manufacture of Rubber
Copolymers
Step-Growth Polymers
Physical Properties of Polymers
Biodegradable Polymers
Pericyclic Reactions
Three Kinds of Pericyclic Reactions
Molecular Orbitals and Orbital Symmetry
Electrocyclic Reactions
Cycloaddition Reactions
Sigmatropic Rearrangements
Pericyclic Reactions in Biological Systems
Summary of the Selection Rules for Pericyclic Reactions
The Organic Chemistry of Drugs: Discovery and Design
Naming Drugs
Lead Compounds
Molecular Modification
Random Screening
Serendipity in Drug Development
Receptors
Drugs as Enzyme Inhibitors
Designing a Suicide Substrate
Quantitative Structure-Activity Relation-ships (QSAR)
Molecular Modeling
Combinatorial Organic Synthesis
Antiviral Drugs
Economics of Drugs
Governmental Regulations
Appendices
Physical Properties of Organic Compounds
Values
Derivations of Rate Laws
Summary of Methods Used to Synthesize a Particular Functional Group
Summary of Methods Used to Form Carbon-Carbon Bonds
Spectroscopy Tables
Answers to Selected Problems
Glossary
Photo Credits
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