Organic Chemistry – Paula Yurkanis – 5th Edition

Description

This innovative book from acclaimed educator Paula Bruice is organized in a way that discourages rote memorization. The author’s writing has been praised for anticipating readers’ questions, and appeals to their need to learn visually and by solving problems. Emphasizing that learners should reason their way to rather than memorize facts, Bruice encourages them to think about what they have learned previously and apply that in a new setting.

The book balances coverage of traditional topics with bioorganic chemistry, highlights mechanistic similarities, and ties synthesis and together–teaching the reactivity of a functional group and the synthesis of compounds obtained as a result of that reactivity. For the study of chemistry.

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  • 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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Mohamed Karam
14/12/2016 8:22 am

Excellent book for organic chemistry students. I used this book for both organic chemistry I and II, and the author is the same author as my textbook. The 2nd language book is a condensed version of the textbook and includes all necessary reactions and relevant information. Its like taking the textbook, removing backstories and case studies, and reducing the page count to only include what is absolutely needed. I used this book before each exam, covering the units that were about to be tested. The book could also be completed in its entirety as a way to review material before the final exam as well.

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