Book , Print in English

Organic chemistry

Paula Yurkanis Bruice, University of California, Santa Barbara.
  • Boston : Pearson, [2014]
  • Copyright Notice: ©2014
  • Seventh edition.
  • 1 volume (various pagings) : color illustrations ; 29 cm
Subjects
Genre
  • Textbooks.
Contents
  • note: pt. 1 INTRODUCTION TO THE STUDY OF ORGANIC CHEMISTRY
  • 1. Remembering General Chemistry: Electronic Structure and Bonding
  • New material on how to draw Lewis structures and how to predict bond angles and the orbitals used in bonding
  • 1.1. Structure of an Atom
  • 1.2. How the Electrons in an Atom Are Distributed
  • 1.3. Ionic and Covalent Bonds
  • 1.4. How the Structure of a Compound Is Represented
  • Problem-Solving Strategy
  • 1.5. Atomic Orbitals
  • 1.6. Introduction to Molecular Orbital Theory
  • 1.7. How Single Bonds Are Formed in Organic Compounds
  • 1.8. How a Double Bond Is Formed: The Bonds in Ethene
  • 1.9. How a Triple Bond Is Formed: The Bonds in Ethyne
  • 1.10. Bonds in the Methyl Cation, the Methyl Radical, and the Methyl Anion
  • 1.11. Bonds in Ammonia and in the Ammonium Ion
  • 1.12. Bonds in Water
  • 1.13. Bond in a Hydrogen Halide
  • 1.14. Hybridization and Molecular Geometry
  • Problem-Solving Strategy
  • 1.15. Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles
  • Problem-Solving Strategy
  • 1.16. Dipole Moments of Molecules
  • Some Important Things To Remember
  • Problems
  • 2. Acids and Bases: Central to Understanding Organic Chemistry
  • New chapter on Acid/Base Chemistry reinforces fundamental concepts
  • 2.1. Introduction to Acids and Bases
  • 2.2. pKa and pH
  • Problem-Solving Strategy
  • 2.3. Organic Acids and Bases
  • Problem-Solving Strategy
  • 2.4. How to Predict the Outcome of an Acid-Base Reaction
  • 2.5. How to Determine the Position of Equilibrium
  • 2.6. How the Structure of an Acid Affects its pKa Value
  • 2.7. How Substituents Affect the Strength of an Acid
  • Problem-Solving Strategy
  • 2.8. Introduction to Delocalized Electrons
  • 2.9. Summary of the Factors that Determine Acid Strength
  • 2.10. How pH Affects the Structure of an Organic Compound
  • Problem-Solving Strategy
  • 2.11. Buffer Solutions
  • 2.12. Lewis Acids and Bases
  • Some Important Things To Remember
  • Problems
  • New tutorial on Acid/Base Chemistry provides students with opportunities to self assess and develop foundational skills needed for future topics in organic chemistry
  • Enhanced by MasteringChemistry®
  • Acids and Bases: Equilibrium Basics
  • Acids and Bases: Factors Influencing Acid Strength
  • Acids and Bases: pH Influence on Acid and Base Structure
  • Tutorial Acids And Bases
  • 3. Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure
  • Increased content on noncovalent interactions in chemical and biological systems
  • 3.1. How Alkyl Substituents Are Named
  • 3.2. Nomenclature of Alkanes
  • 3.3. Nomenclature of Cycloalkanes
  • Skeletal Structures
  • Problem-Solving Strategy
  • 3.4. Nomenclature of Alkyl Halides
  • 3.5. Nomenclature of Ethers
  • 3.6. Nomenclature of Alcohols
  • 3.7. Nomenclature of Amines
  • 3.8. Structures of Alkyl Halides, Alcohols, Ethers, and Amines
  • 3.9. Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines
  • Problem-Solving Strategy
  • 3.10. Rotation Occurs About Carbon-Carbon Single Bonds
  • 3.11. Some Cycloalkanes Have Angle Strain
  • Problem-Solving Strategy
  • 3.12. Conformers of Cyclohexane
  • 3.13. Conformers of Monosubstituted Cyclohexanes
  • Problem-Solving Strategy
  • 3.14. Conformers of Disubstituted Cyclohexanes
  • 3.15. Fused Cyclohexane Rings
  • Some Important Things To Remember
  • Problems
  • pt. 2 ELECTROPHILIC ADDITION REACTIONS, STEREOCHEMISTRY, AND ELECTRON DELOCALIZATION
  • Tutorial Using Molecular Models
  • 4. Isomers: The Arrangement of Atoms in Space
  • Enhanced by MasteringChemistry®
  • Using Molecular Models: Basics of Model Building
  • Using Molecular Models: Interpret Chiral Models
  • Using Molecular Models: Interpret Cyclic Models
  • coverage of stereoisomers now precedes the coverage of the reactions of alkenes
  • 4.1. Cis-Trans Isomers Result From Restricted Rotation
  • 4.2. Chiral Object Has a Nonsuperimposable Mirror Image
  • 4.3. Asymmetric Center Is a Cause of Chirality in a Molecule
  • 4.4. Isomers with One Asymmetric Center
  • 4.5. Asymmetric Centers and Stereocenters
  • 4.6. How to Draw Enantiomers
  • 4.7. Naming Enantiomers by the R,S System
  • Problem-Solving Strategy
  • Problem-Solving Strategy
  • 4.8. Chiral Compounds Are Optically Active
  • 4.9. How Specific Rotation Is Measured
  • 4.10. Enantiomeric Excess
  • 4.11. Compounds with More than One Asymmetric Center
  • 4.12. Stereoisomers of Cyclic Compounds
  • Problem-Solving Strategy
  • 4.13. Meso Compounds Have Asymmetric Centers but Are Optically Inactive
  • Problem-Solving Strategy
  • 4.14. How to Name Isomers with More than One Asymmetric Center
  • Problem-Solving Strategy
  • 4.15. How Enantiomers Can Be Separated
  • 4.16. Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers
  • Some Important Things To Remember
  • Problems
  • Two new tutorials reinforce student understanding and visualization of structure
  • Enhanced by MasteringChemistry®
  • Interconverting Structural Representations: Interpreting Fischer Projections
  • Interconverting Structural Representations: Fischer Projections with Multiple Stereocenters
  • Interconverting Structural Representations: Interpreting Newman Projections
  • Tutorial Interconverting Structural Representations
  • 5. Alkenes: Structure, Nomenclature, and an Introduction to Reactivity
  • Thermodynamics and Kinetics
  • 5.1. Molecular Formulas and the Degree of Unsaturation
  • 5.2. Nomenclature of Alkenes
  • 5.3. Structure of Alkenes
  • 5.4. Naming Alkenes Using the E,Z System
  • Problem-Solving Strategy
  • Problem-Solving Strategy
  • 5.5. How an Organic Compound Reacts Depends on its Functional Group
  • 5.6. How Alkenes React
  • Curved Arrows Show the Flow of Electrons
  • 5.7. Thermodynamics and Kinetics
  • 5.8. Rate of a Chemical Reaction
  • 5.9. Difference Between the Rate of a Reaction and the Rate Constant for a Reaction
  • 5.10. Reaction Coordinate Diagram Describes the Energy Changes that Take Place during a Reaction
  • 5.11. Catalysis
  • 5.12. Catalysis by Enzymes
  • Some Important Things To Remember
  • Problems
  • New tutorial gives students practice drawing curved arrows
  • Enhanced by MasteringChemistry®
  • Exercise in Drawing Curved Arrows: Basics of Pushing Electrons
  • Exercise in Drawing Curved Arrows: Predicting Electron Movement
  • Exercise in Drawing Curved Arrows: Interpreting Electron Movement
  • Tutorial An Exercise in Drawing Curved Arrows: Pushing Electrons
  • 6. Reactions of Alkenes
  • Stereochemistry of Addition Reactions
  • Alkoxymercuration was removed since it is now rarely used because of toxicity concerns. Ozonolysis has been added as has using 9-BBN for hydroboration and MCPBA for epoxidation
  • 6.1. Addition of a Hydrogen Halide to an Alkene
  • 6.2. Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon
  • 6.3. What Does the Structure of the Transition State Look Like?
  • 6.4. Electrophilic Addition Reactions Are Regioselective
  • Problem-Solving Strategy
  • 6.5. Addition of Water to an Alkene
  • 6.6. Addition of an Alcohol to an Alkene
  • 6.7. Carbocation Will Rearrange if it Can Form a More Stable Carbocation
  • 6.8. Addition of Borane to an Alkene: Hydroboration-Oxidation
  • 6.9. Addition of a Halogen to an Alkene
  • Problem-Solving Strategy
  • 6.10. Addition of a Peroxyacid to an Alkene
  • 6.11. Addition of Ozone to an Alkene: Ozonolysis
  • Problem-Solving Strategy
  • 6.12. Addition of Hydrogen to an Alkene
  • Problem-Solving Strategy
  • 6.13. Relative Stabilities of Alkenes
  • 6.14. Regioselective, Stereoselective, and Stereospecific Reactions
  • 6.15. Stereochemistry of Electrophilic Addition Reactions of Alkenes
  • Problem-Solving Strategy
  • 6.16. Stereochemistry of Enzyme-Catalyzed Reactions
  • 6.17. Enantiomers Can Be Distinguished by Biological Molecules
  • 6.18. Reactions and Synthesis
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • 7. Reactions of Alkynes
  • Introduction to Multistep Synthesis
  • Discussion of reactivity has been reorganized and clarified. The mechanism for keto-enol interconversion has been added
  • 7.1. Nomenclature of Alkynes
  • 7.2. How to Name a Compound That Has More than One Functional Group
  • 7.3. Physical Properties of Unsaturated Hydrocarbons
  • 7.4. Structure of Alkynes
  • 7.5. Alkynes Are Less Reactive than Alkenes
  • 7.6. Addition of Hydrogen Halides and the Addition of Halogens to an Alkyne
  • 7.7. Addition of Water to an Alkyne
  • 7.8. Addition of Borane to an Alkyne: Hydroboration-Oxidation
  • 7.9. Addition of Hydrogen to an Alkyne
  • 7.10. Hydrogen Bonded to an sp Carbon Is "Acidic"
  • Problem-Solving Strategy
  • 7.11. Synthesis Using Acetylide Ions
  • Designing a Synthesis I
  • 7.12. Introduction to Multistep Synthesis
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • 8. Delocalized Electrons and Their Effect on Stability, pKa, and the Products of a Reaction
  • Discussion of aromaticity has been added to allow this concept to be carried throughout the text starting at an earlier point
  • 8.1. Delocalized Electrons Explain Benzene's Structure
  • 8.2. Bonding in Benzene
  • 8.3. Resonance Contributors and the Resonance Hybrid
  • 8.4. How to Draw Resonance Contributors
  • 8.5. Predicted Stabilities of Resonance Contributors
  • 8.6. Delocalization Energy Is the Additional Stability Delocalized Electrons Give to a Compound --
  • Contents note continued: Problem-Solving Strategy
  • 8.7. Benzene Is an Aromatic Compound
  • 8.8. Two Criteria for Aromaticity
  • 8.9. Applying the Criteria for Aromaticity
  • Problem-Solving Strategy
  • 8.10. Aromatic Heterocyclic Compounds
  • 8.11. Antiaromaticity
  • 8.12. Molecular Orbital Description of Aromaticity and Antiaromaticity
  • 8.13. More Examples that Show How Delocalized Electrons Increase Stability
  • Introduces a new feature, "Organizing What We Know," which highlights how all organic compounds can be divided into families and all members of a family react in the same way. Furthermore, each family can be put into one of four groups and all the families in a group react in similar ways
  • 8.14. Molecular Orbital Description of Stability
  • 8.15. How Delocalized Electrons Affect pKa Values
  • Problem-Solving Strategy
  • 8.16. Delocalized Electrons Can Affect the Product of a Reaction
  • 8.17. Reactions of Dienes
  • 8.18. Thermodynamic versus Kinetic Control
  • 8.19. Diels-Alder Reaction Is a 1,4-Addition Reaction
  • 8.20. Retrosynthetic Analysis of the Diels-Alder Reaction
  • 8.21. Organizing What We Know About the Reactions of Organic Compounds
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • New tutorial gives students practice drawing resonance contributors
  • Enhanced by MasteringChemistry®
  • Drawing Resonance Contributors: Moving π Electrons
  • Drawing Resonance Contributors: Predicting Contributor Structure
  • Drawing Resonance Contributors: Substituted Benzene Compounds
  • Tutorial Drawing Resonance Contributors
  • pt. 3 SUBSTITUTION AND ELIMINATION REACTIONS
  • 9. Substitution Reactions of Alkyl Halides
  • Rewritten to incorporate the new finding that secondary alkyl halides do not undergo SN1 reactions
  • 9.1. Mechanism for an SN2 Reaction
  • 9.2. Factors that Affect SN2 Reactions
  • 9.3. Mechanism for an SN1 Reaction
  • 9.4. Factors that Affect SN1 Reactions
  • 9.5. Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides
  • Problem-Solving Strategy
  • 9.6. Competition Between SN2 and SN1 Reactions
  • Problem-Solving Strategy
  • 9.7. Role of the Solvent in SN1 and SN2 Reactions
  • 9.8. Intermolecular versus Intramolecular Reactions
  • Problem-Solving Strategy
  • 9.9. Methylating Agents Used by Chemists versus Those Used by Cells
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • 10. Elimination Reactions of Alkyl Halides
  • Competition Between Substitution and Elimination
  • Rewritten to incorporate the new finding that secondary alkyl halides do not undergo E1 reactions
  • 10.1. E2 Reaction
  • 10.2. E2 Reaction Is Regioselective
  • 10.3. E1 Reaction
  • Problem-Solving Strategy
  • 10.4. Benzylic and Allylic Halides
  • 10.5. Competition Between E2 and E1 Reactions
  • 10.6. E2 and E1 Reactions Are Stereoselective
  • Problem-Solving Strategy
  • 10.7. Elimination from Substituted Cyclohexanes
  • 10.8. Kinetic Isotope Effect Can Help Determine a Mechanism
  • 10.9. Competition Between Substitution and Elimination
  • 10.10. Substitution and Elimination Reactions in Synthesis
  • Designing a Synthesis II
  • 10.11. Approaching the Problem
  • Some Important Things To Remember
  • Summary Of Reactions
  • Problems
  • 11. Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols
  • Hypochlorous acid introduced as an alternative to toxic-chromuium-containing compounds
  • 11.1. Nucleophilic Substitution Reactions of Alcohols: Forming Alkyl Halides
  • 11.2. Other Methods Used to Convert Alcohols into Alkyl Halides
  • 11.3. Converting an Alcohol Into a Sulfonate Ester
  • 11.4. Elimination Reactions of Alcohols: Dehydration
  • Problem-Solving Strategy
  • 11.5. Oxidation of Alcohols
  • 11.6. Nucleophilic Substitution Reactions of Ethers
  • 11.7. Nucleophilic Substitution Reactions of Epoxides
  • 11.8. Arene Oxides
  • 11.9. Amines Do Not Undergo Substitution or Elimination Reactions
  • 11.10. Quaternary Ammonium Hydroxides Undergo Elimination Reactions
  • 11.11. Thiols, Sulfides, and Sulfonium Salts
  • 11.12. Organizing What We Know About the Reactions of Organic Compounds
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • 12. Organometallic Compounds
  • Discussion of palladium-catalyzed coupling reactions and their mechanisms has been expanded. Solved problems and problem-solving strategies were added to facilitate understanding
  • 12.1. Organolithium and Organomagnesium Compounds
  • 12.2. Transmetallation
  • 12.3. Organocuprates
  • 12.4. Palladium-Catalyzed Coupling Reactions
  • Problem-Solving Strategy
  • 12.5. Alkene Metathesis
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • 13. Radicals
  • Reactions of Alkanes
  • Now includes the mechanism for the oxidation of fats and oils by oxygen
  • 13.1. Alkanes Are Unreactive Compounds
  • 13.2. Chlorination and Bromination of Alkanes
  • 13.3. Radical Stability Depends On the Number of Alkyl Groups Attached to the Carbon with the Unpaired Electron
  • 13.4. Distribution of Products Depends On Probability and Reactivity
  • 13.5. Reactivity-Selectivity Principle
  • Problem-Solving Strategy
  • 13.6. Formation of Explosive Peroxides
  • 13.7. Addition of Radicals to an Alkene
  • 13.8. Stereochemistry of Radical Substitution and Radical Addition Reactions
  • 13.9. Radical Substitution of Benzylic and Allylic Hydrogens
  • Designing a Synthesis III
  • 13.10. More Practice With Multistep Synthesis
  • 13.11. Radical Reactions Occur In Biological Systems
  • 13.12. Radicals and Stratospheric Ozone
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • Tutorial Drawing Curved Arrows In Radical Systems
  • Enhanced by MasteringChemistry®
  • Curved Arrows in Radical Systems: Interpreting Electron Movement
  • Curved Arrows in Radical Systems: Predicting Electron Movement
  • Curved Arrows in Radical Systems: Resonance
  • pt. 4 IDENTIFICATION OF ORGANIC COMPOUNDS
  • 14. Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet/Visible Spectroscopy
  • Added the "rule of 13"
  • 14.1. Mass Spectrometry
  • 14.2. Mass Spectrum
  • Fragmentation
  • 14.3. Using the m/z Value of the Molecular Ion to Calculate the Molecular Formula
  • Problem-Solving Strategy
  • 14.4. Isotopes in Mass Spectrometry
  • 14.5. High-Resolution Mass Spectrometry Can Reveal Molecular Formulas
  • 14.6. Fragmentation Patterns of Functional Groups
  • 14.7. Other Ionization Methods
  • 14.8. Gas Chromatography-Mass Spectrometry
  • 14.9. Spectroscopy and the Electromagnetic Spectrum
  • 14.10. Infrared Spectroscopy
  • 14.11. Characteristic Infrared Absorption Bands
  • 14.12. Intensity of Absorption Bands
  • 14.13. Position of Absorption Bands
  • 14.14. Position and Shape of an Absorption Band Is Affected By Electron Delocalization, Electron Donation and Withdrawal, and Hydrogen Bonding
  • Problem-Solving Strategy
  • 14.15. Absence of Absorption Bands
  • 14.16. Some Vibrations Are Infrared Inactive
  • 14.17. How to Interpret an Infrared Spectrum
  • 14.18. Ultraviolet and Visible Spectroscopy
  • 14.19. Beer-Lambert Law
  • 14.20. Effect of Conjugation on λmax
  • 14.21. Visible Spectrum and Color
  • 14.22. Some Uses of UV/VIS Spectroscopy
  • Some Important Things To Remember
  • Problems
  • 15. NMR Spectroscopy
  • There are now 50 additional spectroscopy problems in the Study Guide and Solutions Manual
  • 15.1. Introduction to NMR Spectroscopy
  • 15.2. Fourier Transform NMR
  • 15.3. Shielding Causes Different Hydrogens to Show Signals at Different Frequencies
  • 15.4. Number of Signals in an 1H NMR Spectrum
  • Problem-Solving Strategy
  • 15.5. Chemical Shift Tells How Far the Signal Is from the Reference Signal
  • 15.6. Relative Positions of 1H NMR Signals
  • 15.7. Characteristic Values of Chemical Shifts
  • 15.8. Diamagnetic Anisotropy
  • 15.9. Integration of NMR Signals Reveals the Relative Number of Protons Causing Each Signal
  • 15.10. Splitting of Signals Is Described by the N + 1 Rule
  • 15.11. What Causes Splitting?
  • 15.12. More Examples of 1H NMR Spectra
  • 15.13. Coupling Constants Identify Coupled Protons
  • Problem-Solving Strategy
  • 15.14. Splitting Diagrams Explain the Multiplicity of a Signal
  • 15.15. Diastereotopic Hydrogens are Not Chemically Equivalent
  • 15.16. Time Dependence of NMR Spectroscopy
  • 15.17. Protons Bonded To Oxygen and Nitrogen
  • 15.18. Use of Deuterium in 1H NMR Spectroscopy
  • 15.19. Resolution of 1H NMR Spectra
  • 15.20. 13C NMR Spectroscopy
  • Problem-Solving Strategy
  • 15.21. Dept 13C NMR Spectra
  • 15.22. Two-Dimensional NMR Spectroscopy
  • 15.23. NMR Used in Medicine Is Called Magnetic Resonance Imaging
  • 15.24. X-Ray Crystallography
  • Some Important Things To Remember
  • Problems
  • pt. 5 CARBONYL COMPOUNDS
  • 16. Reactions of Carboxylic Acids and Carboxylic Derivatives
  • Acid anhydrides are carboxylic acid derivatives but they don't look like carboxylic acids. Anhydrides, therefore, were moved to the end of the chapter to allow students to focus on the similarities between carboxylic acids, acyl chlorides, esters, and amides. Acid anhydrides are now better placed since they come just before phosphoric acid [ect.]
  • 16.1. Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives
  • 16.2. Structures of Carboxylic Acids and Carboxylic Acid Derivatives
  • 16.3. Physical Properties of Carbonyl Compounds
  • 16.4. Fatty Acids Are Long-Chain Carboxylic Acids --
  • Contents note continued: 16.5. How Carboxylic Acids and Carboxylic Acid Derivatives React
  • Problem-Solving Strategy
  • 16.6. Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives
  • 16.7. General Mechanism for Nucleophilic Addition-Elimination Reactions
  • 16.8. Reactions of Acyl Chlorides
  • 16.9. Reactions of Esters
  • 16.10. Acid-Catalyzed Ester Hydrolysis and Transesterification
  • 16.11. Hydroxide-Ion-Promoted Ester Hydrolysis
  • 16.12. How the Mechanism for Nucleophilic Addition-Elimination Was Confirmed
  • 16.13. Fats and Oils Are Triglycerides
  • 16.14. Reactions of Carboxylic Acids
  • Problem-Solving Strategy
  • 16.15. Reactions of Amides
  • 16.16. Acid-Catalyzed Amide Hydrolysis and Alcoholysis
  • 16.17. Hydroxide-Ion Promoted Hydrolysis of Amides
  • 16.18. Hydrolysis of an Imide: A Way to Synthesize Primary Amines
  • 16.19. Nitriles
  • 16.20. Acid Anhydrides
  • 16.21. Dicarboxylic Acids
  • 16.22. How Chemists Activate Carboxylic Acids
  • 16.23. How Cells Activate Carboxylic Acids
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • 17. Reactions of Aldehydes and Ketones
  • More Reactions of Carboxylic Acid Derivatives
  • Reactions of α,β-Unsaturated Carbonyl Compounds
  • Enhanced discussion of reduction reactions. Added a discussion of chemoselective reactions
  • 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 Gringard Reagents
  • Problem-Solving Strategy
  • 17.5. Reactions of Carbonyl Compounds with Acetylide Ions
  • 17.6. Reactions of Aldehydes and Ketones with Cyanide Ion
  • 17.7. Reactions of Carbonyl Compounds with Hydride Ion
  • 17.8. More About Reduction Reactions
  • 17.9. Chemoselective Reactions
  • 17.10. Reactions of Aldehydes and Ketones with Amines
  • 17.11. Reactions of Aldehydes and Ketones with Water
  • 17.12. Reactions of Aldehydes and Ketones with Alcohols
  • Problem-Solving Strategy
  • 17.13. Protecting Groups
  • 17.14. Addition of Sulfur Nucleophiles
  • 17.15. Reactions of Aldehydes and Ketones with a Peroxyacid
  • 17.16. Wittig Reaction Forms an Alkene
  • Designing a Synthesis IV
  • 17.17. Disconnections, Synthons, and Synthetic Equivalents
  • 17.18. Nucleophilic Addition to α, β-Unsaturated Aldehydes and Ketones
  • 17.19. Nucleophilic Addition to α, β-Unsaturated Carboxylic Acid Derivatives
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • 18. Reactions at the α-Carbon of Carbonyl Compounds
  • Streamlined the discussion of both the reactions of enolate ions and crossed aldol additions and condensations. Added new examples of retrosynthetic analysis
  • 18.1. Acidity of an α-Hydrogen
  • Problem-Solving Strategy
  • 18.2. Keto-Enol Tautomers
  • 18.3. Keto-Enol Interconversion
  • 18.4. Halogenation of the α-Carbon of Aldehydes and Ketones
  • 18.5. Halogenation of the α-Carbon of Carboxylic Acids: The Hell-Volhard-Zelinski Reaction
  • 18.6. Forming an Enolate Ion
  • 18.7. Alkylating the α-Carbon of Carbonyl Compounds
  • Problem-Solving Strategy
  • 18.8. Alkylating and Acylating the α-Carbon Using an Enamine Intermediate
  • 18.9. Alkylating the β-Carbon: The Michael Reaction
  • 18.10. Aldol Addition Forms β-Hydroxyaldehydes or β-Hydroxyketones
  • 18.11. Dehydration of Aldol Addition Products Forms α,β-Unsaturated Aldehydes and Ketones
  • 18.12. Crossed Aldol Addition
  • 18.13. Claisen Condensation Forms a β-Keto Ester
  • 18.14. Other Crossed Condensations
  • 18.15. Intramolecular Condensations and Intramolecular Aldol Additions
  • 18.16. Robinson Annulation
  • Problem-Solving Strategy
  • 18.17. Carboxylic Acids with a Carbonyl Group at the 3-Position Can Be Decarboxylated
  • 18.18. Malonic Ester Synthesis: A Way to Synthesize a Carboxylic Acid
  • 18.19. Acetoacetic Ester Synthesis: A Way to Synthesize a Methyl Ketone
  • Designing a Synthesis V
  • 18.20. Making New Carbon-Carbon Bonds
  • 18.21. Reactions at the α-Carbon in Living Systems
  • 18.22. Organizing What We Know About the Reactions of Organic Compounds
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • pt. 6 AROMATIC COMPOUNDS
  • 19. Reactions of Benzene and Substituted Benzenes
  • 19.1. Nomenclature of Monosubstituted Benzenes
  • 19.2. How Benzene Reacts
  • 19.3. General Mechanism for Electrophilic Aromatic Substitution Reactions
  • 19.4. Halogenation of Benzene
  • 19.5. Nitration of Benzene
  • 19.6. Sulfonation of Benzene
  • 19.7. Friedel-Crafts Acylation of Benzene
  • 19.8. Friedel-Crafts Alkylation of Benzene
  • 19.9. Alkylation of Benzene by Acylation-Reduction
  • 19.10. Using Coupling Reactions to Alkylate Benzene
  • 19.11. It Is Important to Have More than One Way to Carry Out a Reaction
  • 19.12. How Some Substituents on a Benzene Ring Can Be Chemically Changed
  • 19.13. Nomenclature of Disubstituted and Polysubstituted Benzenes
  • 19.14. Effect of Substituents on Reactivity
  • 19.15. Effect of Substituents on Orientation
  • 19.16. Effect of Substituents on pKa
  • Problem-Solving Strategy
  • 19.17. Ortho-Para Ratio
  • 19.18. Additional Considerations Regarding Substituent Effects
  • Designing a Synthesis VI
  • 19.19. Synthesis of Monosubstituted and Disubstituted Benzenes
  • 19.20. Synthesis of Trisubstituted Benzenes
  • 19.21. Synthesis of Substituted Benzenes Using Arenediazonium Salts
  • 19.22. Arenediazonium Ion as an Electrophile
  • 19.23. Mechanism for the Reaction of Amines with Nitrous Acid
  • 19.24. Nucleophilic Aromatic Substitution: An Addition-Elimination Reaction
  • Designing a Synthesis VII
  • 19.25. Synthesis of Cyclic Compounds
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • New tutorial on synthesis and retrosynthetic analysis including two examples of a multistep synthesis from the literature
  • Tutorial Synthesis and Retrosynthetic Analysis
  • Enhanced by MasteringChemistry®
  • Synthesis and Retrosynthetic Analysis: Functional Groups
  • Synthesis and Retrosynthetic Analysis: Carbon Chain
  • Synthesis and Retrosynthetic Analysis: Retrosynthesis of 2-Pentanone Using Reactions of Carbonyl Compounds
  • 20. More About Amines
  • Reactions of Heterocyclic Compounds
  • 20.1. More About Amine Nomenclature
  • 20.2. More About the Acid-Base Properties of Amines
  • 20.3. Amines React as Bases and as Nucleophiles
  • 20.4. Synthesis of Amines
  • 20.5. Aromatic Five-Membered-Ring Heterocycles
  • 20.6. Aromatic Six-Membered-Ring Heterocycles
  • Problem-Solving Strategy
  • 20.7. Some Amine Heterocycles Have Important Roles in Nature
  • 20.8. Organizing What We Know About the Reactions of Organic Compounds
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • pt. 7 BIOORGANIC COMPOUNDS
  • 21. Organic Chemistry of Carbohydrates
  • reactions of aromatic heterocycles now follows the reactions of other aromatic compounds
  • 21.1. Classification of Carbohydrates
  • 21.2. 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. Oxidation-Reduction Reactions of Monosaccharides
  • 21.7. Lengthening the Chain: The Kiliani-Fischer Synthesis
  • 21.8. Shortening the Chain: The Wohl Degradation
  • 21.9. Stereochemistry of Glucose: The Fischer Proof
  • 21.10. Monosaccharides Form Cyclic Hemiacetals
  • 21.11. Glucose Is the Most Stable Aldohexose
  • 21.12. Formation of Glycosides
  • 21.13. Anomeric Effect
  • 21.14. Reducing and Nonreducing Sugars
  • 21.15. Disaccharides
  • 21.16. Polysaccharides
  • 21.17. Some Naturally Occurring Compounds Derived from Carbohydrates
  • 21.18. Carbohydrates on Cell Surfaces
  • 21.19. Artificial Sweeteners
  • Some Important Things To Remember
  • Summary of Reactions
  • Problems
  • 22. Organic Chemistry of Amino Acids, Peptides, and Proteins
  • new discussion on diseases caused by protein misfolding
  • 22.1. Nomenclature of Amino Acids
  • 22.2. Configuration of Amino Acids
  • 22.3. Acid-Base Properties of Amino Acids
  • 22.4. Isoelectric Point
  • 22.5. Separating Amino Acids
  • 22.6. Synthesis of Amino Acids
  • 22.7. Resolution of Racemic Mixtures of Amino Acids
  • 22.8. Peptide Bonds and Disulfide Bonds
  • 22.9. Some Interesting Peptides
  • 22.10. Strategy of Peptide Bond Synthesis: N-Protection and C-Activation
  • 22.11. Automated Peptide Synthesis
  • 22.12. Introduction to Protein Structure
  • 22.13. How to Determine the Primary Structure of a Polypeptide or Protein
  • Problem-Solving Strategy
  • 22.14. Secondary Structure
  • 22.15. Tertiary Structure
  • 22.16. Quaternary Structure
  • 22.17. Protein Denaturation
  • Some Important Things To Remember
  • Problems
  • 23. Catalysis in Organic Reactions and in Enzymatic Reactions
  • Revised to emphasize the connection between the organic reactions that occur in test tubes with the organic reactions that occur in cells
  • 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. Mechanisms for Two Enzyme-Catalyzed Reactions that are Reminiscent of Acid-Catalyzed Amide Hydrolysis --
  • Contents note continued: 23.10. Mechanism for an Enzyme-Catalyzed Reaction that Involves Two Sequential SN2 Reactions
  • 23.11. Mechanism for an Enzyme-Catalyzed Reaction that Is Reminiscent of the Base-Catalyzed Enediol Rearrangement
  • 23.12. Mechanism for an Enzyme-Catalyzed Reaction that Is Reminiscent of an Aldol Addition
  • Some Important Things To Remember
  • Problems
  • 24. Organic Chemistry of the Coenzymes, Compounds Derived from Vitamins
  • Added the mechanism for the conversion of succinate to fumarate
  • 24.1. Niacin: The Vitamin Needed for Many Redox Reactions
  • 24.2. Riboflavin: Another Vitamin Used in Redox Reactions
  • 24.3. Vitamin B1: The Vitamin Needed for Acyl Group Transfer
  • 24.4. Vitamin H: The Vitamin Needed for Carboxylation of an α-Carbon
  • 24.5. Vitamin B6: The Vitamin Needed for Amino Acid Transformations
  • 24.6. Vitamin B12: The Vitamin Needed for Certain Isomerizations
  • 24.7. Folic Acid: The Vitamin Needed for One-Carbon Transfer
  • 24.8. Vitamin K: The Vitamin Needed for Carboxylation of Glutamate
  • Some Important Things To Remember
  • Problems
  • 25. Organic Chemistry of the Metabolic Pathways
  • Terpene Biosynthesis
  • New coverage of organic reactions that occur in gluconeogenesis and discussions of thermodynamic control and the regulation of metabolic pathways. Revised to emphasize the connection between the organic reactions that occur in test tubes with those that occur in cells. New section on terpene [ect.]
  • 25.1. ATP Is Used for Phosphoryl Transfer Reactions
  • 25.2. ATP Activates a Compound by Giving it a Good Leaving Group
  • 25.3. Why ATP Is Kinetically Stable in a Cell
  • 25.4. "High-Energy" Character of Phosphoanhydride Bonds
  • 25.5. Four Stages of Catabolism
  • 25.6. Catabolism of Fats
  • 25.7. Catabolism of Carbohydrates
  • Problem-Solving Strategy
  • 25.8. Fate of Pyruvate
  • 25.9. Catabolism of Proteins
  • 25.10. Citric Acid Cycle
  • 25.11. Oxidative Phosphorylation
  • 25.12. Anabolism
  • 25.13. Gluconeogenesis
  • 25.14. Regulating Metabolic Pathways
  • 25.15. Amino Acid Biosynthesis
  • 25.16. Terpenes Contain Carbon Atoms in Multiples of Five
  • 25.17. How Terpenes are Biosynthesized
  • Problem-Solving Strategy
  • 25.18. How Nature Synthesizes Cholesterol
  • Some Important Things To Remember
  • Problems
  • 26. Chemistry of the Nucleic Acids
  • New section on antiviral drugs and the chemical reasons for their antiviral activity. Recently published information about the function of segments of DNA that were thought to contain no information
  • 26.1. Nucleosides and Nucleotides
  • 26.2. Other Important Nucleotides
  • 26.3. Nucleic Acids Are Composed of Nucleotide Subunits
  • 26.4. Why DNA Does Not Have A 2'-OH Group
  • 26.5. Biosynthesis of DNA Is Called Replication
  • 26.6. DNA and Heredity
  • 26.7. Biosynthesis of RNA Is Called Transcription
  • 26.8. RNAs Used for Protein Biosynthesis
  • 26.9. Biosynthesis of Proteins Is Called Translation
  • 26.10. Why DNA Contains Thymine Instead of Uracil
  • 26.11. Antiviral Drugs
  • 26.12. How the Base Sequence of DNA Is Determined
  • 26.13. Polymerase Chain Reaction (PCR)
  • 26.14. Genetic Engineering
  • Some Important Things To Remember
  • Problems
  • pt. 8 SPECIAL TOPICS IN ORGANIC CHEMISTRY
  • 27. Synthetic Polymers
  • 27.1. There Are Two Major Classes of Synthetic Polymers
  • 27.2. Chain-Growth Polymers
  • 27.3. Stereochemistry of Polymerization
  • Ziegler-Natta Catalysts
  • 27.4. Polymerization of Dienes
  • Manufacture of Rubber
  • 27.5. Copolymers
  • 27.6. Step-Growth Polymers
  • 27.7. Classes of Step-Growth Polymers
  • 27.8. Physical Properties of Polymers
  • 27.9. Recycling Polymers
  • 27.10. Biodegradable Polymers
  • Some Important Things To Remember
  • Problems
  • 28. Pericyclic Reactions
  • 28.1. There Are Three Kinds of Pericyclic Reactions
  • 28.2. Molecular Orbitals and Orbital Symmetry
  • 28.3. Electrocyclic Reactions
  • 28.4. Cycloaddition Reactions
  • 28.5. Sigmatropic Rearrangements
  • 28.6. Pericyclic Reactions in Biological Systems
  • 28.7. Summary of the Selection Rules for Pericyclic Reactions
  • Some Important Things To Remember
  • Problems
  • Appendices
  • I. pKa Values
  • II. Kinetics
  • III. Summary of Methods Used to Synthesize a Particular Functional Group
  • IV. Summary of Methods Employed to Form Carbon-Carbon Bonds.
Other information
  • OCLC
ISBN
  • 9780321803221
  • 0321803221
  • 9780321853103
  • 0321853105
Identifying numbers
  • LCCN: 2012036294
  • OCLC: 820678644
  • OCLC: 820678644