Organic chemistry

著者

• Bruice, Paula Yurkanis

書誌事項

Organic chemistry

Paula Yurkanis Bruice

Pearson Prentice Hall, c2007

5th ed., Pearson international ed.

注記

Includes index

内容説明・目次

内容説明

For full-year courses in organic chemistry taken by science and pre-health professions majors. This innovative text is organized in a way that discourages rote memorization, by emphasizing what functional groups do rather than how they are made, highlighting mechanistic similarities and tying synthesis and reactivity together. Bruice's writing has been praised for anticipating students' questions, appealing to their visual and problem solving needs. The text balances coverage of traditional topics with bioorganic chemistry, recognizing the importance of bioorganic topics to today's students.

目次

• I: AN INTRODUCTION TO THE STUDY OF ORGANIC CHEMISTRY 1. ELECTRONIC STRUCTURE AND BONDING * ACIDS AND BASES 1.1 The Structure of an Atom 1.2 How the Electrons in an Atom are Distributed 1.3 Ionic and Covalent Bonds Ionic Bonds are Formed by the Transfer of Electrons Covalent Bonds are Formed by Sharing Electrons Polar Covalent Bonds 1.4 How the Structure of a Compound is Represented Lewis Structures Kekule Structures Condensed Structures 1.5 Atomic Orbitals 1.6 An Introduction to Molecular Orbital Theory 1.7 How Single Bonds are Formed in Organic Compounds The Bonds in Methane The Bonds in Ethane 1.8 How a Double Bond is Formed: The Bonds in Ethene 1.9 How a Triple Bonds is Formed: The Bonds in Ethyne 1.10 The Bonds in the Methyl Cation, the Methyl Radical, and the Methyl Anion The Methyl Cation The Methyl Radical The Methyl Anion 1.11 The Bonds in Water 1.12 The Bonds in Ammonia and in the Ammonium Ion 1.13 The Bonds in the Hydrogen Halides 1.14 Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles 1.15 The Dipole Moments of Molecules 1.16 An Introduction to Acids and Bases 1.17 pKa and pH 1.18 Organic Acids and Bases 1.19 How to Predict the Outcome of an Acid-Base Reaction 1.20 How the Structure of an Acid Affects Its Acidity 1.21 How Substituents Affect the Strength of an Acid 1.22 An Introduction to Delocalized Electrons 1.23 A Summary of the Factors that Determine Acid Strength 1.24 How the pH Affects the Structure of an Organic Compound 1.25 Buffer Solutions 1.26 The Second Definition of Acid and Base: Lewis Acids and Bases 2. AN INTRODUCTION TO ORGANIC COMPOUNDS NOMENCLATURE, PHYSICAL PROPERTIES, AND REPRESENTATION OF STRUCTURE 2.1 How Alkyl Substituents are Named 2.2 Nomenclature of Alkanes 2.3 Nomenclature of Cycloalkanes 2.4 Nomenclature of Alkyl Halides 2.5 Nomenclature of Ethers 2.6 Nomenclature of Alcohols 2.7 Nomenclature of Amines 2.8 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines 2.9 The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines Boiling Points Melting Points Solubility 2.10 Rotation Occurs About Carbon-Carbon Bonds 2.11 Some Cycloalkanes Have Ring Strain 2.12 Conformations of Cyclohexane 2.13 Conformers of Monosubstituted Cyclohexanes 2.14 Conformers of Disubstituted Cyclohexanes II: ELECTROPHILIC ADDITION REACTIONS, STEREOCHEMISTRY, AND ELECTRON DEELOCALIZATION 3. ALKENES: STRUCTURE, NOMENCLATURE AND AN INTRODUCTION TO REACTIVITY * THERMODYNAMICS AND KINETICS 3.1 Molecular Formulas and the Degree of Unsaturation 3.2 Nomenclature of Alkenes 3.3 The Structures of Alkenes 3.4 Alkenes Can Have Cis and Trans Isomers 3.5 Naming Alkenes Using the E,Z System 3.6 How Alkenes React * Curved Arrows Show the Flow of Electrons 3.7 Thermodynamics and Kinetics A Reaction Coordinate Diagram Describes the Reaction Pathway Thermodynamics: How Much Product Is Formed? Kinetics: How Fast Is the Product Formed? 3.8 Using a Reaction Coordinate Diagram to Describe a Reaction 4. THE REACTIONS OF ALKENES 4.1 Addition of a Hydrogen Halide to an Alkene 4.2 Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon 4.3 The Structure of the Transition State Lies Partway Between the Structures of the Reactants and Products 4.4 Electrophilic Addition Reactions Are Regioselective 4.5 Acid-Catalyzed Addition Reactions Addition of Water to an Alkene Addition of an Alcohol to an Alkene 4.6 A Carbocation will Rearrange if It Can Form a More Stable Carbocation 4.7 Addition of a Halogen to an Alkene 4.8 Oxymercuration-Demercuration: Are Other Ways to Add Water or Alcohol to an Alkene 4.9 Addition of a Peroxyacid to an Alkene 4.10 Addition of Borane to an Alkene: Hydroboration-Oxidation 4.11 Addition of Hydrogen to an Alkene * The Relative Stabilities of Alkenes 4.12 Reactions and Synthesis 5. STEREOCHEMISTRY: THE ARRANGEMENT OF ATOMS IN SPACE
• THE STEREOCHEMISTRY OF ADDITION REACTIONS 5.1 Cis-Trans Isomers Result From Restricted Rotation 5.2 A Chiral Object has a Nonsuperimposable Mirror Image 5.3 An Asymmetric Center Is a Cause of Chirality In a Molecule 5.4 Isomers with One Asymmetric Center 5.5 Asymmetric Centers and Stereocenters 5.6 How to Draw Enantiomers 5.7 Naming Enantiomers by the R,S System 5.8 Chiral Compounds are Optically Active 5.9 How Specific Rotation is Measured 5.10 Enantiomeric Excess 5.11 Isomers with More than One Asymmetric Center 5.12 Meso Compounds Have Asymmetric Centers but are Optically Inactive 5.13 How to Name Isomers with More than One Asymmetric Center 5.14 Reactions of Compounds that Contain a Asymmetric Center 5.15 The Absolute Configuration of (+)-Glyceraldehyde 5.16 How Enantiomers Can be Separated 5.17 Nitrogen and Phosphorous Atoms Can be Asymmetric Centers 5.18 The Stereochemistry of Reactions: Regioselective, Stereoselective, and Stereospecific Reactions 5.19 The Stereochemistry of Electrophilic Addition Reactions of Alkenes Addition Reactions that Form a Product with One Asymmetric Center Addition Reactions that Form Products with Two Asymmetric Centers Addition Reactions that Form a Carbocation Intermediate The Stereochemistry of Hydrogen Addition The Stereochemistry of Peroxyacid Addition The Stereochemistry of Hydroboration-Oxidation Addition Reactions that Form a Cyclic Bromonium Ion Intermediate 5.20 The Stereochemistry of Enzyme-Catalyzed Reactions 5.21 Enantiomers can be Distinguished by Biological Molecules Enymes Receptors 6. THE REACTIONS OF ALKYNES * AN INTRODUCTION TO MULTISTEP SYNTHESIS 6.1 The Nomenclature of Alkynes 6.2 How to Name a Compound That Has More than One Functional Group 6.3 The Physical Properties of Unsaturated Hydrocarbons 6.4 The Structure of Alkynes 6.5 How Alkynes React 6.6 Addition of Hydrogen Halides and Addition of Halogens to an Alkyne 6.7 Addition of Water to an Alkyne 6.8 Addition of Borane to an Alkyne: Hydroboration-Oxidation 6.9 Addition of Hydrogen to an Alkyne 6.10 A Hydrogen Bonded to an sp Carbon is "Acidic" 6.11 Synthesis Using Acetylide Ions 6.12 Designing a Synthesis I: An Introduction to Multistep Synthesis 7. DELOCALIZED ELECTRONS AND THEIR EFFECT ON STABILITY, REACTIVITY, AND pKa * MORE ABOUT MOLECULAR ORBITAL THEORY 7.1 Benzene Has Delocalized Electrons 7.2 The Bonding in Benzene 7.3 Resonance Contributors and the Resonance Hybrid 7.4 How to Draw Resonance Contributors 7.5 The Predicted Stabilites of Resonance Contributors 7.6 Delocalization Energy Is the Additional Stability Delocalized Electrons Give to a Compound 7.7 Examples That Illustrate the Effect of Delocalized Electrons on Stability Stability of Dienes Stability of Allylic and Benzylic Cations 7.8 A Molecular Orbital Description of Stability 1,3-Butadiene and 1,4-Pentadiene 1,3,5-Hexatriene and Benzene 7.9 How Delocalized Electrons Affect pKa 7.10 Delocalized Electrons Can Affect the Product of a Reaction Reactions of Isolated Dienes Reactions of Conjugated Dienes 7.11 Thermodynamic versus Kinetic Control of Reactions 7.12 The Diels-Alder Reaction Is a 1,4-Addition Reaction A Molecular Orbital Description of the Diels-Alder Reaction Predicting the Product When Both Reagents Are Unsymmetrically Substituted Conformations of the Diene The Stereochemistry of the Diels-Alder Reaction III: SUBSTITUTION AND ELIMINATION REACTIONS 8. SUBSTITUTION REACTIONS OF OF ALKYL HALIDES 8.1 How Alkyl Halides React 8.2 The Mechanism of an SN2 Reaction 8.3 Factors that Affect SN2 Reactions The Leaving Group The Nucleophile Nucleophilicity is Affected by the Solvent Nucleophilicity is Affected by Steric Effects 8.4 The Reversibility of an SN2 Reaction Depends on the Basicities of the Leaving Groups in the Forward and Reverse Directions 8.5 The Mechanism of an SN1 Reaction 8.6 Factors that Affect an SN1 Reaction The Leaving Group The Nucleophile Carbocation Rearrangements 8.7 More About the Stereochemistry of SN2 and SN1 Reactions Stereochemistry of SN2 Reactions Stereochemistry of SN1 Reactions 8.8 Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides 8.9 Competition Between SN2 and SN1 Reactions 8.10 The Role of the Solvent in SN2 and SN1 Reactions How a Solvent Affects Reaction Rates in General How a Solvent Affects the Rate of an SN1 Reaction How a Solvent Affects the Rate of an SN2 Reaction 8.11 Biological Methylating Reagents Have Good Leaving Groups 9. ELIMINATION REACTIONS OF ALKYL HALIDES * COMPETITION BETWEEN SUBSTITUTION AND ELIMINATION 9.1 The E2 Reaction 9.2 An E2 Reaction is Regioselective 9.3 The E1 Reaction 9.4 Competition Between E2 and E1 Reactions 9.5 E2 and E1 Reactions are Stereoselective The Stereoisomers Formed in an E2 Reaction The Stereoisomers Formed in an E1 Reaction 9.6 Elimination from Substituted Cyclohexanes E2 Reactions of Substituted Cyclohexanes E1 Reactions of Substituted Cyclohexanes 9.7 A Kinetic Isotope Effect Can Help Determine a Mechanism 9.8 Competition Between Substitution and Elimination SN2/E2 Conditions SN1/E1 Conditions 9.9 Substitution and Elimination Reactions in Synthesis Using Substitution Reactions to Synthesize Compounds Using Elimination Reactions to Synthesize Compounds 9.10 Consecutive E2 Elimination Reactions 9.11 Intermolecular Versus Intramolecular Reactions 9.12 Designing a Synthesis II: Approaching the Problem 10. REACTIONS OF ALCOHOLS, AMINES, ETHERS, EXPOXIDES, AND SULFUR-CONTAINING COMPOUNDS * ORGANOMETALLIC COMPOUNDS 10.1 Nucleophilic Substitution Reactions of Alcohols: Forming Alkyl Halides 10.2 Other Methods for Converting Alcohols into Alkyl Halides 10.3 Converting Alcohols into Sulfonate Esters 10.4 Elimination Reactions of Alcohols: Dehydration 10.5 Oxidation of Alcohols 10.6 Amines do not Undergo Substitution or Elimination Reactions but Are the Most Common Organic Bases 10.7 Nucleophilic Substitution Reactions of Ethers 10.8 Nucleophilic Substitution Reactions of Epoxides 10.9 Arene Oxides 10.10 Crown Ethers 10.11 Thiols, Sulfides, and Sulfonium Salts 10.12 Organometallic Compounds 10.13 Coupling Reactions 11. RADICALS * REACTIONS OF ALKANES 11.1 Alkanes are Unreactive Compounds 11.2 Chlorination and Bromination of Alkanes 11.3 Radical Stability Depends on the Number of Alkyl Groups Attached to the Carbon with the Unpaired Electron 11.4 The Distribution of Products Depends on Probability and Reactivity 11.5 The Reactivity-Selectivity Principle 11.6 Addition of Radicals to an Alkene 11.7 Stereochemistry of Radical Substitution and Addition Reactions 11.8 Radical Substitution of Benzylic and Allylic Hydrogens 11.9 Designing a Synthesis III: More Practice with Multistep Synthesis 11.10 Radical Reactions Occur in Biological Systems 11.11 Radicals and Stratospheric Ozone IV: IDENTIFICATION OF ORGANIC COMPOUNDS 12. MASS SPECTROMETRY, INFRARED SPECTROSCOPY, AND ULTRAVIOLET/VISIBLE SPECTROSCOPY 12.1 Mass Spectrometry 12.2 The Mass Spectrum. Fragmentation 12.3 Isotopes in Mass Spectrometry 12.4 High-Resolution Mass Spectrometry Can Determine Molecular Formulas 12.5 Fragmentation Patterns of Functional Groups Alkyl Halides Ethers Alcohols Ketones 12.6 Spectroscopy and the Electromagnetic Spectrum 12.7 Infrared Spectroscopy Obtaining an Infrared Spectrum The Functional Group and Fingerprint Regions 12.8 Characteristic Infrared Absorption Bands 12.9 The Intensity of Absorption Bands 12.10 The Position of Absorption Bands Hooke's Law The Effect of Bond Order 12.11 The Position of an Absorption Band is Affected by Electron Delocalization, Electron Donation and Withdrawal, and Hydrogen Bonding O-GH Absorption Bands C-H Absortion Bands 12.12 The Shape of Absorption Bands 12.13 The Absence of Absorption Bands 12.14 Some Vibrations are Infrared Inactive 12.15 A Lesson in Interpreting Infrared Spectra 12.16 Ultraviolet and Visible Spectroscopy 12.17 The Beer-Lambert Law 12.18 The Effect of Conjugation on lmax 12.19 The Visible Spectrum and Color 12.20 Uses of UV/Vis Spectroscopy 13. NMR SPECTROSCOPY 13.1 An Introduction to NMR Spectroscopy 13.2 Fourier Transform NMR 13.3 Shielding Causes Different Hydrogens to Show Signals at Different Frequencies 13.4 The Number of Signals in an 1H NMR Spectrum 13.5 The Chemical Shift Tells How Far the Signal Is from the Reference Signal 13.6 The Relative Positions of 1H NMR Signals 13.7 Characteristic Values of Chemical Shifts 13.8 Diamagnetic Anisotropy 13.9 The Integration of NMR Signals Reveals the Relative Number of Protons Causing the Signal 13.10 Splitting of the Signals is Desribed by the N+1 Rule 13.11 More Examples of 1H NMR Spectra 13.12 Coupling Constants Identify Coupled Protons 13.13 Splitting Diagrams Explain the Multiplicity of a Signal 13.14 The Time Dependence of NMR Spectroscopy 13.15 Protons Bonded to Oxygen and Nitrogen 13.16 The Use of Deuterium in 1H NMR Spectroscopy 13.17 The Resolution of 1H NMR Spectra 13.18 13C NMR Spectroscopy 13.19 DEPT 13C NMR Spectra 13.20 Two-Dimensional NMR Spectroscopy 13.21 NMR Used in Medicine is Called Magnetic Resonance Imaging V: AROMATIC COMPOUNDS 14. AROMATICITY * REACTIONS OF BENZENE 14.1 Aromatic Compounds are Unusually Stable 14.2 The Two Criteria for Aromaticity 14.3 Applying the Criteria for Aromaticity 14.4 Aromatic Heterocyclic Compounds 14.5 Some Chemical Consequences of Aromaticity 14.6 Antiaromaticity 14.7 A Molecular Orbital Description of Aromaticity and Antiaromaticity 14.8 Nomenclature of Monosubstituted Benzenes 14.9 How Benzene Reacts 14.10 General Mechanism for Electrophilic Aromatic Substitution Reactions 14.11 Halogenation of Benzene 14.12 Nitration of Benzene 14.13 Sulfonation of Benzene 14.14 Friedel-Crafts Acylation of Benzene 14.15 Friedel-Crafts Alkylation of Benzene 14.16 Alkylation of Benzene by Acylation-Reduction 14.17 Using Coupling Reactions to Alkylate Benzene 14.18 It is important to Have More than One Way to Carry Out a Reaction 14.19 How Some Substituents on a Benzene Ring Can Be Chemically Changed 15. REACTIONS OF SUBSTITUTED BENZENES 15.1 Nomenclature of Disubstituted and Polysubstituted Benzenes 15.2 Some Substituents Increase the Reactivity of a Benzene Ring and Some Decrease Its Reactivity Inductive Electron Withdrawal Electron Donation by Hyperconjugation Resonance Electron Donation and Withdrawal Relative Reactivity of Substituted Benzenes 15.3 The Effect of Substituents on Orientation 15.4 The Effect of Substituents on pKa 15.5 The Ortho/Para Ratio 15.6 Additional Considerations Regarding Substituent Effects 15.7 Designing a Synthesis III: Synthesis of Monosubstituted and Disubstituted Benzenes 15.8 Synthesis of Trisubstituted Benzenes 15.9 Synthesis of Substituted Benzenes Using Arenediazonium Salts 15.10 The Arenediazonium Ion as an Electrophile 15.11 Mechanism for the Reaction of Amines with Nitrous Acid 15.12 Nucleophilic Aromatic Substitution: An Addition-Elimination Mechanism 15.13 Nucleophilic Aromatic Substitution: An Elimination-Addition Mechanism that Forms a Benzyne Intermediate 15.14 Polycyclic Benzenoid Hydrocarbons VI: CARBONYL COMPOUNDS 16. CARBONYL COMPOUNDS I: NUCLEOPHILIC ACYL SUBSTITUTION 16.1 Nomenclature of Carboxylic Acids and Caboxylic Acid Derivatives 16.2 Structures of Carboxylic Acids and Carboxylic Acid Derivatives 16.3 Physical Properties of Carbonyl Compounds 16.4 Naturally Occurring Carboxylic Acids and Carboxylic Acid Derivatives 16.5 How Class I Carbonyl Compounds React 16.6 Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives 16.7 General Mechanism for Nucleophilic Acyl Substitution Reactions 16.8 Reactions of Acyl Halides 16.9 Reactions of Acid Anhydrides 16.10 Reactions of Esters 16.11 Acid-Catalyzed Ester Hydrolysis 16.12 Hydroxide-Ion Promoted Ester Hydrolysis 16.13 How the Mechanism for Nucleophilic Acyl Substitution Reactions Was Confirmed 16.14 Soaps, Detergents, and Micelles 16.15 Reactions of Carboxylic Acids 16.16 Reactions of Amides 16.17 The Hydrolysis of Amides Is Catalyzed by Acids 16.18 Hydrolysis of an Imide: A Way to Synthesize Primary Amines 16.19 Hydrolysis of Nitriles 16.20 Designing a Synthesis V: The Synthesis of Cyclic Compounds 16.21 How Chemists Activate Carboxylic Acids 16.22 How Cells Activate Carboxylic Acids 16.23 Dicarboxylic Acids and Their Derivatives 17. CARBONYL COMPOUNDS II: 17.1 Nomenclature of Aldehydes and Ketones 17.2 Relative Reactivities of Carbonyl Compounds 17.3 How Aldehydes and Ketones React 17.4 Reactions of Carbonyl Compounds with Grignard Reagents 17.5 Reactions of Carbonyl Compounds with Acetylide Ions 17.6 Reactions of Carbonyl Compounds with Hydride Ion 17.7 Reactions of Aldehydes and Ketones with Hydrogen Cyanide 17.8 Reactions of Aldehydes and Ketones with Amines and Derivatives of Amines 17.9 Reactions of Aldehydes and Ketones with Water 17.10 Reactions of Aldehydes and Ketones with Alcohols 17.11 Protecting Groups 17.12 Addition of Sulfur Nucleophiles 17.13 The Wittig Reaction Forms an Alkene 17.14 Stereochemistry of Nucleophilic Addition Reactions: Re and Si Faces 17.15 Designing a Synthesis VI: Disconnections, Synthons, and Synthetic Equivalents 17.16 Nucleophilic Addition to a,b-Unsaturated Aldehydes and Ketones 17.17 Nucleophilic Addition to a,b-Unsaturated Carboxylic Acid Derivatives 17.18 Enzyme-Catalyzed Additions to a,b-Unsaturated Carbonyl Compounds 18. CARBONYL COMPOUNDS III: REACTIONS AT THE a-CARBON 18.1 Acidity of an a-Hydrogens 18.2 Keto-Enol Tautomers 18.3 Enolization 18.4 How Enols and Enolate Ions React 18.5 Halogenation of the a-Carbon of Aldehydes and Ketones. Acid-Catalyzed Halogenation Base-Promoted Halogenation The Haloform Reaction 18.6 Halogenation of the a-Carbon of Carboxylic Acids: The Hell-Volhard-Zelinski Reaction 18.7 a-Halogenated Carbonyl Compounds Are Useful in Synthesis 18.8 Using Lithium Diisopropylamide (LDA) to Form an Enolate 18.9 Alkylation of the a-Carbon of Carbonyl Compounds 18.10 Alkylation and Acylation of the a-Carbon Using an Enamine Intermediate 18.11 Alkylation of the b-Carbon: The Michael Reaction 18.12 An Aldol Addition Forms b-Hydroxyaldehydes or b -Hydroxyketones 18.13 Dehydration of Aldol Addition Products Forms a,b-Unsaturated Aldehydes and Ketones 18.14 The Mixed Aldol Addition 18.15 A Claisen Condensation Forms a b-Keto Ester 18.16 The Mixed Claisen Condensation 18.17 Intramolecular Condensation and Addition Reactions Intramolecular Claisen Condensations Intramolecular Aldol Additions The Robinson Annulation 18.18 3-Oxocarboxylic Acids Can Be Dehydrated 18.19 The Malonic Ester Synthesis: A Way to Snthesize a Carboxylic Acid 18.20 The Acetoacetic Ester Synthesis: A Way Synthesize a Methyl Ketone 18.21 Designing a Synthesis VII: Making New Carbon-Carbon Bonds 18.22 Reactions at the a-Carbon in Biological Systems A Biological Aldol Condensation A Biological Claisen Condensation A Biological Decarboxylation VII: OXIDATION-REDUCTION REACTIONS AND AMINES 19. MORE ABOUT OXIDATION-REDUCTION REACTIONS 19.1 Reduction Reactions Reduction by Addition of Two Hydrogen Atoms Reduction by Addition of an Electron, a Proton, an Electron, and a Proton Reduction by Addition of a Hydride Ion and a Proton 19.2 Oxidation of Alcohols 19.3 Oxidation of Aldehydes and Ketones 19.4 Designing a Synthesis VIII: Controlling Stereochemistry 19.5 Hydroxylation of Alkenes 19.6 Oxidative Cleavage of 1,2-Diols 19.7 Oxidative Cleavage of Alkenes 19.8 Oxidative Cleavage of Alkynes 19.9 Designing a Synthesis IX: Functional Group Interconversion 20. MORE ABOUT AMINES. HETEROCYCLIC COMPOUNDS 20.1 More About Amine Nomenclature 20.2 Amines Invert Rapidly 20.3 More About the Acid-Base Properties of Amines 20.4 Amines React as Bases and as Nucleophiles 20.5 Quaternary Ammonium Hydroxides Undergo Elimination Reactions 20.6 Phase-Transfer Catalysis 20.7 Oxidation of Amines: The Cope Elimination Reaction 20.8 Synthesis of Amines 20.9 Aromatic Five-Membered Ring Heterocycles 20.10 Aromatic Six-Membered-Ring Heterocycles 20.11 Amine Heterocycles Have Important Roles in Nature VIII: BIOORGANIC COMPOUNDS 21. CARBOHYDRATES 21.1 Classification of Carbohydrtes 21.2 The D and L Notation 21.3 Configurations of the Aldoses 21.4 Configurations of the Ketoses 21.5 Reactions of Monosaccharides in Basic Solutions 21.6 Redox Reactions of Monosaccharides 21.7 Monosaccharides Form Crystalline Osazones 21.8 Lengthening the Chain: The Kiliani-Fischer Synthesis 21.9 Shortening the Chain: The Wohl Degradation 21.10 Stereochemistry of Glucose: the Fischer Proof 21.11 Monosaccharides Form Cyclic Hemiacetals 21.12 Glucose Is the Most Stable Aldohexose 21.13 Acylation and Alkylation of Monosaccharides 21.14 Formation of Glycosides 21.15 The Anomeric Effect 21.16 Reducing and Nonreducing Sugars 21.17 Determination of Ring Size 21.18 Disaccharides 21.19 Polysaccharides 21.20 Some Naturally Occurring Products Derived from Carbohydrates 21.21 Carbohydrates on Cell Surfaces 21.22 Synthetic Sweeteners 22. AMINO ACIDS, PEPTIDES, AND PROTEINS 22.1 Classification and Nomenclature of Amino Acids 22.2 Configuration of the Amino Acids 22.3 Acid-Base Properties of Amino Acids 22.4 The Isoelectric Point 22.5 Separation of Amino Acids 22.6 Resolution of Racemic Mixtures of Amino Acids 22.7 Peptide Bonds and Disulfide Bonds 22.8 Some Interesting Peptides 22.9 The Strategy of Peptide Bond Synthesis: N-Protection and C-Activation 22.10 Automated Peptide Synthesis 22.11 An Introduction to Protein Structure 22.12 How to Determine the Primary Structure of a Peptide or a Protein 22.13 Secondary Structure of Proteins 22.14 Tertiary Structure of Proteins 22.15 Quaternary Structure of Proteins 22.16 Protein Denaturation 23. CATALYSIS 23.1 Catalysis in Organic Reactions 23.2 Acid Catalysis 23.3 Base Catalysis 23.4 Nucleophilic Catalysis 23.5 Metal-Ion Catalysis 23.6 Intramolecular Reactions 23.7 Intramolecular Catalysis 23.8 Catalysis in Biological Reactions 23.9 Enzyme-Catalyzed Reactions Mechanism for Carboxypeptidase A Mechanism for Serine Proteases Mechanism for Lysozyme Mechanism for Glucose-6-phosphate Isomerase Mechanism of Aldolase 24. THE ORGANIC MECHANISMS OF THE COENZYMES 24.1 An Introduction to Metabolism 24.2 The Vitamin Needed for Many Redox Reactions: Vitamin B3 24.3 Flavin Adenine Dinucleotide and Flavin Mononucleotide: Vitamin B2 23.4 Thiamine Pyrophosphate: Vitamin B1 23.5 Biotin: Vitamin H 24.6 Pyridoxal Phosphate: Vitamin B6 24.7 Coenzyme B12: Vitamin B12 24.8 Tetrahydrofolate: Folic Acid 24.9 Vitamin KH2: Vitamin K 25: THE CHEMISTRY OF METABOLISM 25.1 The Four Stages of Catabolism 25.2 ATP Is the Carrier of Chemical Energy 25.3 There Are Three Mechanisms for Phosphoryl Transfer Reactions 25.4 The "High-Energy" Character of Phosphoanhydride Bonds 25.5 Why ATP Is Kinetically Stable in a Cell 25.6 The Catabolism of Fats 25.7 The Catabolism of Carbohydrates 25.8 The Fates of Pyruvate 25.9 The Catabolism of Proteins 25.10 The Citric Acid Cycle 25.11 Oxidative Phosphorylation 25.12 Anabolism 26. LIPIDS 26.1 Fatty Acids Are Long-Chain Carboxylic Acids 26.2 Waxes Are High-Molecular Weight Esters 26.3 Fats and Oils 26.4 Phospholipids and Sphingolipids are the Components of Membranes 26.5 Prostaglandins Regulate Physiological Responses 26.6 Terpenes Contain Carbon Atoms in Multiples of Five 26.7 Vitamin A Is a Terpene 26.8 How Terpenes Are Biosynthesized 26.9 Steroids Are Chemical Messengers 26.10 How Nature Synthesizes Cholesterol 26.11 Synthetic Steroids 27. NUCLEOSIDES, NUCLEOTIDES, AND NUCLEIC ACIDS 27.1 Nucleosides and Nucleotides 27.2 Other Important Nucleotides 27.3 Nucleic Acids Are Composed of Nucleotide Subunits 27.4 DNA Is Stable but RNA Is Easily Cleaved 27.5 Biosynthesis of DNA Is Called Replication 27.6 Biosynthesis of RNA Is Called Transcription 27.7 There Are Three Kinds of RNA 27.8 Biosynthesis of Proteins Is Called Translation 27.9 Why DNA Contains Thymine Instead of Uracil 27.10 How the Base Sequence of DNA Is Determined 27.11 Polymerase Chain Reaction (PCR) 27.12 Genetic Engineering 27.13 Laboratory Synthesis of DNA Strands IX: SPECIAL TOPICS IN ORGANIC CHEMISTRY 28. SYNTHETIC POLYMERS 28.1 There Are Two Major Classes of Synthetic Polymers 28.2 Chain-Growth Polymers Radical Polymerization Branching of the Polymer Chain Cationic Polymerization Anionic Polymerization 28.3 Stereochemistry of Polymerization. Ziegler-Natta Catalysts 28.4 Polymerization of Dienes. The Manufacture of Rubber 28.5 Copolymers 28.6 Step-Growth Polymers 28.7 Physical Properties of Polymers 29. PERICYCLIC REACTIONS 29.1 There Are Three Kinds of Pericyclic Reations 29.2 Molecular Orbitals and Orbital Symmetry 29.3 Electrocyclic Reactions 29.4 Cycloaddition Reactions 29.5 Sigmatropic Rearrangements Migration of Hydrogen Migration of Carbon 29.6 Pericyclic Rections in Biological Systems Biological Cycloaddition Reactions A Biological Reaction Involving an Electrocyclic Reaction and a Sigmatropic Rearrangement 29.7 Summary of the Selection Rules for Pericyclic Reactions 30. THE ORGANIC CHEMISTRY OF DRUGS: DISCOVERY AND DESIGN 30.1 Naming Drugs 30.2 Lead Compounds 30.3 Molecular Modification 30.4 Random Screening 30.5 Serendipity in Drug Development 30.6 Receptors 30.7 Drugs as Enzyme Inhibitors 30.8 Designing a Suicide Substrate 30.9 Quantitative Structure-Activity Relationships (QSARs) 30.10 Molecular Modeling 30.11 Combinatorial Organic Synthesis 30.12 Antiviral Drugs 30.13 Economics of Drugs: Governmental Regulations

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詳細情報

• NII書誌ID(NCID): BA78656194
• ISBN:
  • 0131996312
• 出版国コード: us
• タイトル言語コード: eng
• 本文言語コード: eng
• 出版地: Upper Saddle River
• ページ数/冊数: xxxviii, 1319, 35, 14, 1, 27 p., plates. [3] p.
• 大きさ: 27 cm
• 分類:
  • LCC : QD251.3
  • DC22 : 547
• 件名:
  • LCSH : Chemistry, Organic