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Organic Chemistry
ISBN: 9780131963283 | 0131963287
Format: PaperbackPublisher: Pearson College Div
Pub. Date: 7/5/2006
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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.
| 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 B... MORE | |
| 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 | |
| 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 | |
| Enzyme-Catalyzed Additions to | |
| Carbonyl Compounds III: Reactions at the | |
| Acidity of | |
| Keto-Enol Tautomerism | |
| How Enols and Enolate Ions React | |
| Halogenation of the | |
| Halogenation of the | |
| Using LDA to Form an Enolate | |
| Alkylation of the | |
| Alkylation and Acylation of the | |
| Alkylation of the | |
| The Aldol Addition | |
| Dehydration of Aldol Addition Products: Formation of | |
| 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 | |
| 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 | |
| Table of Contents provided by Publisher. All Rights Reserved. |
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