Organic Chemistry （2ND）

[Book Description]

Organic chemistry is not merely a compilation of principles, but rather, it is a disciplined method of thought and analysis. Success in organic chemistry requires mastery in two core aspects: fundamental concepts and the skills needed to apply those concepts and solve problems. Readers must learn to become proficient at approaching new situations methodically, based on a repertoire of skills. These skills are vital for successful problem solving in organic chemistry. Existing textbooks provide extensive coverage of, the principles, but there is far less emphasis on the skills needed to actually solve problems.

[Table of Contents]

1 A Review of General Chemistry: Electrons,    1   (50)
    Bonds, and Molecular Properties
      1.1 Introduction to Organic Chemistry        2   (1)
      1.2 The Structural Theory of Matter          3   (1)
      1.3 Electrons, Bonds, and Lewis Structures   4   (4)
      1.4 Identifying Formal Charges               8   (1)
      1.5 Induction and Polar Covalent Bonds       9   (3)
        Practically Speaking Electrostatic         12  (1)
        Potential Maps
      1.6 Atomic Orbitals                          12  (4)
      1.7 Valence Bond Theory                      16  (1)
      1.8 Molecular Orbital Theory                 17  (1)
      1.9 Hybridized Atomic Orbitals               18  (7)
      1.10 VSEPR Theory: Predicting Geometry       25  (5)
      1.11 Dipole Moments and Molecular Polarity   30  (4)
      1.12 Intermolecular Forces and Physical      34  (7)
      Properties
        Practically Speaking Biomimicry and        36  (4)
        Gecko Feet
        Medically Speaking Drug-Receptor           40  (1)
        Interactions
1.13 Solubility 41 (10)
        Medically Speaking Propofol: The           42  (9)
        Importance of Drug Solubility
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    2 Molecular Representations                    51  (45)
      2.1 Molecular Representations                52  (2)
      2.2 Bond-Line Structures                     54  (5)
      2.3 Identifying Functional Groups            59  (3)
        Medically Speaking Marine Natural          61  (1)
        Products
      2.4 Carbon Atoms with Formal Charges         62  (1)
      2.5 Identifying Lone Pairs                   62  (4)
      2.6 Three-Dimensional Bond-Line Structures   66  (2)
        Medically Speaking Identifying the         67  (1)
        Pharmacophore
      2.7 Introduction to Resonance                68  (2)
      2.8 Curved Arrows                            70  (3)
      2.9 Formal Charges in Resonance Structures   73  (2)
      2.10 Drawing Resonance Structures via        75  (6)
      Pattern Recognition
      2.11 Assessing Relative Importance of        81  (4)
      Resonance Structures
      2.12 Delocalized and Localized Lone Pairs    85  (11)
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    3 Acids and Bases                              96  (43)
      3.1 Introduction to Brønsted-Lowry    97  (1)
      Acids and Bases
      3.2 Flow of Electron Density: Curved         97  (4)
      Arrow Notation
        Medically Speaking Antacids and            100 (1)
        Heartburn
      3.3 Brønsted-Lowry Acidity: A         101 (8)
      Quantitative Perspective
        Medically Speaking Drug Distribution       108 (1)
        and pKa
      3.4 Brønsted-Lowry Acidity:           109 (13)
      Qualitative Perspective
      3.5 Position of Equilibrium and Choice of    122 (3)
      Reagents
      3.6 Leveling Effect                          125 (1)
      3.7 Solvating Effects                        126 (1)
      3.8 Counterions                              127 (2)
        Practically Speaking Baking Soda versus    128 (1)
        Baking Powder
      3.9 Lewis Acids and Bases                    129 (10)
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    4 Alkanes and Cycloalkanes                     139 (53)
      4.1 Introduction to Alkanes                  140 (1)
      4.2 Nomenclature of Alkanes                  140 (14)
        Practically Speaking Pheromones:           145 (8)
        Chemical Messengers
        Medically Speaking Naming Drugs            153 (1)
      4.3 Constitutional Isomers of Alkanes        154 (1)
      4.4 Relative Stability of Isomeric Alkanes   155 (1)
      4.5 Sources and Uses of Alkanes              156 (2)
        Practically Speaking: An Introduction      158 (1)
        to Polymers
      4.6 Drawing Newman Projections               158 (2)
      4.7 Conformational Analysis of Ethane and    160 (2)
      Propane
      4.8 Conformational Analyses of Butane        162 (5)
        Medically Speaking Drugs and Their         166 (1)
        Conformations
      4.9 Cycloalkanes                             167 (2)
        Medically Speaking Cyclopropane as an      168 (1)
        Inhalation Anesthetic
      4.10 Conformations of Cyclohexane            169 (1)
      4.11 Drawing Chair Conformations             170 (2)
      4.12 Monosubstituted Cyclohexane             172 (3)
      4.13 Disubstituted Cydohexane                175 (5)
      4.14 cis-trans Stereoisomerism               180 (1)
      4.15 Polycyclic Systems                      181 (11)
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    5 Stereoisomerism                              192 (44)
      5.1 Overview of Isomerism                    193 (3)
      5.2 Introduction to Stereoisomerism          196 (7)
        Practically Speaking The Sense of Smell    202 (1)
      5.3 Designating Configuration Using the      203 (6)
      Cahn-Ingold-Prelog System
        Medically Speaking Chiral Drugs            208 (1)
      5.4 Optical Activity                         209 (5)
      5.5 Stereoisomeric Relationships:            214 (4)
      Enantiomers and Diastereomers
      5.6 Symmetry and Chirality                   218 (5)
      5.7 Fischer Projections                      223 (2)
      5.8 Conformationally Mobile Systems          225 (1)
      5.9 Resolution of Enantiomers                226 (10)
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    6 Chemical Reactivity and Mechanisms           236 (51)
      6.1 Enthalpy                                 237 (3)
      6.2 Entropy                                  240 (3)
      6.3 Gibbs Free Energy                        243 (3)
        Practically Speaking Explosives            244 (1)
        Practically Speaking Do Living             245 (1)
        Organisms Violate the Second Law of
        Thermodynamics?
      6.4 Equilibria                               246 (2)
      6.5 Kinetics                                 248 (5)
        Medically Speaking Nitroglycerin: An       251 (1)
        Explosive with Medicinal Properties
        Practically Speaking Beer-Making           252 (1)
      6.6 Reading Energy Diagrams                  253 (3)
      6.7 Nucleophiles and Electrophiles           256 (4)
      6.8 Mechanisms and Arrow Pushing             260 (6)
      6.9 Combining the Patterns of Arrow          266 (2)
      Pushing
      6.10 Drawing Curved Arrows                   268 (3)
      6.11 Carbocation Rearrangements              271 (2)
      6.12 Reversible and Irreversible Reaction    273 (14)
      Arrows
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    7 Substitution Reactions                       287 (54)
      7.1 Introduction to Substitution Reactions   288 (1)
      7.2 Alkyl Halides                            289 (3)
      7.3 Possible Mechanisms for Substitution     292 (4)
      Reactions
      7.4 The SN2 Mechanism                        296 (7)
        Practically Speaking SN2 Reactions in      302 (1)
        Biological Systems---Methylation
      7.5 The SN1 Mechanism                        303 (6)
      7.6 Drawing the Complete Mechanism of an     309 (7)
      SN1 Reaction
      7.7 Drawing the Complete Mechanism of an     316 (4)
      SN2 Reaction
        Medically Speaking Radiolabelled           319 (1)
        Compounds in Diagnostic Medicine
      7.8 Determining Which Mechanism              320 (7)
      Predominates
      7.9 Selecting Reagents to Accomplish         327 (14)
      Functional Group Transformation
        Medically Speaking Pharmacology and        330 (11)
        Drug Design
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    8 Alkenes: Structure and Preparation via       341 (63)
    Elimination Reactions
      8.1 Introduction to Elimination Reactions    342 (1)
      8.2 Alkenes in Nature and in Industry        342 (3)
        Practically Speaking Pheromones to         343 (2)
        Control Insect Populations
      8.3 Nomenclature of Alkenes                  345 (3)
      8.4 Stereoisomerism in Alkenes               348 (5)
        Medically Speaking Phototherapy            352 (1)
        Treatment for Neonatal Jaundice
      8.5 Alkene Stability                         353 (3)
      8.6 Possible Mechanisms for Elimination      356 (2)
      8.7 The E2 Mechanism                         358 (13)
      8.8 Drawing the Products of an E2 Reaction   371 (1)
      8.9 The E1 Mechanism                         372 (5)
      8.10 Drawing the Complete Mechanism of an    377 (5)
      E1 Process
      8.11 Drawing the Complete Mechanism of an    382 (1)
      E2 Process
      8.12 Substitution vs. Elimination:           383 (4)
      Identifying the Reagent
      8.13 Substitution vs. Elimination:           387 (4)
      Identifying the Mechanism(s)
      8.14 Substitution vs. Elimination:           391 (13)
      Predicting the Products
        Review of Synthetically Useful
        Elimination Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    9 Addition Reactions of Alkenes                404 (60)
      9.1 Introduction to Addition Reactions       405 (1)
      9.2 Addition vs. Elimination: A              406 (1)
      Thermodynamic Perspective
      9.3 Hydrohalogenation                        407 (9)
        Practically Speaking Cationic              415 (1)
        Polymerization and Polystyrene
      9.4 Acid-Catalyzed Hydration                 416 (4)
        Practically Speaking Industrial            420 (1)
        Production of Ethanol
      9.5 Oxymercuration-Demercuration             420 (2)
      9.6 Hydroboration-Oxidation                  422 (6)
      9.7 Catalytic Hydrogenation                  428 (7)
        Practically Speaking Partially             434 (1)
        Hydrogenated Fats and Oils
      9.8 Halogenation and Halohydrin Formation    435 (5)
      9.9 Anti Dihydroxylation                     440 (3)
      9.10 Syn Dihydroxylation                     443 (1)
      9.11 Oxidative Cleavage                      444 (2)
      9.12 Predicting Products of an Addition      446 (2)
      Reaction
      9.13 Synthesis Strategies                    448 (16)
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    10 Alkynes                                     464 (36)
      10.1 Introduction to Alkynes                 465 (2)
        Medically Speaking The Role of             466 (1)
        Molecular Rigidity
        Practically Speaking Conducting Organic    467 (1)
        Polymers
      10.2 Nomenclature of Alkynes                 467 (3)
      10.3 Acidity of Acetylene and Terminal       470 (3)
      Alkynes
      10.4 Preparing Alkynes                       473 (1)
      10.5 Reduction of Alkynes                    474 (4)
      10.6 Hydrohalogenation of Alkynes            478 (3)
      10.7 Hydration of Alkynes                    481 (6)
      10.8 Halogenation of Alkynes                 487 (1)
      10.9 Ozonolysis of Alkynes                   487 (1)
      10.10 Alkylation of Terminal Alkynes         488 (1)
      10.11 Synthesis Strategies                   489 (11)
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    11 Radical Reactions                           500 (47)
      11.1 Radicals                                501 (5)
      11.2 Common Patterns in Radical Mechanisms   506 (4)
      11.3 Chlorination of Methane                 510 (3)
      11.4 Thermodynamic Considerations for        513 (3)
      Halogenation Reactions
      11.5 Selectivity of Halogenation             516 (3)
      11.6 Stereochemistry of Halogenation         519 (3)
      11.7 Allylic Bromination                     522 (2)
      11.8 Atmospheric Chemistry and the Ozone     524 (3)
      Layer
        Practically Speaking Fighting Fires        526 (1)
        with Chemicals
      11.9 Autooxidation and Antioxidants          527 (4)
        Medically Speaking Why is an Overdose      530 (1)
        of Acetaminophen Fatal?
      11.10 Radical Addition of HBr:               531 (4)
      Anti-Markovnikov Addition
      11.11 Radical Polymerization                 535 (3)
      11.12 Radical Processes in the               538 (1)
      Petrochemical Industry
      11.13 Halogenation as a Synthetic            538 (9)
      Technique
        Review of Synthetically Useful Radical
        Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    12 Synthesis                                   547 (29)
      12.1 One-Step Syntheses                      548 (1)
      12.2 Functional Group Transformations        549 (5)
      12.3 Reactions that Change the Carbon        554 (3)
      Skeleton
        Medically Speaking Vitamins                556 (1)
      12.4 How to Approach a Synthesis Problem     557 (3)
        Medically Speaking The Total Synthesis     559 (1)
        of Vitamin B12
      12.5 Retrosynthetic Analysis                 560 (8)
        Practically Speaking Retrosynthetic        568 (1)
        Analysis
      12.6 Practical Tips for Increasing           568 (8)
      Proficiency
        Medically Speaking Total Synthesis of      570 (6)
        Taxol
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    13 Alcohols and Phenols                        576 (57)
      13.1 Structure and Properties of Alcohols    677
        Medically Speaking Chain Length as a       582 (1)
        Factor in Drug Design
      13.2 Acidity of Alcohols and Phenols         583 (3)
      13.3 Preparation of Alcohols via             586 (1)
      Substitution or Addition
      13.4 Preparation of Alcohols via Reduction   587 (8)
      13.5 Preparation of Diols                    595 (1)
        Practically Speaking Antifreeze            596 (1)
      13.6 Preparation of Alcohols via Grignard    596 (4)
      Reagents
      13.7 Protection of Alcohols                  600 (2)
      13.8 Preparation of Phenols                  602 (1)
        Medically Speaking Phenols as              603 (1)
        Antifungal Agents
      13.9 Reactions of Acohols:Substitution      603 (66)
      and Elimination
        Practically Speaking Drug Metabolism       607 (2)
      13.10 Reactions of Alcohols: Oxidation       609 (1)
        Practically Speaking Breath Tests to       610 (3)
        Pleasure Blood Alcohol Level
      13.11 Biological Redox Reactions             613 (2)
        Practically Speaking Biological            614 (1)
        Oxidation of Methanol and Ethanol
      13.12 Oxidation of Phenol                    615 (1)
      13.13 Synthesis Strategies                   616 (17)
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    14 Ethers and Epoxides; Thiols and Sulfides    633 (50)
      14.1 Introduction to Ethers                  634 (1)
      14.2 Nomenclature of Ethers                  634 (3)
      14.3 Structure and Properties of Ethers      637 (2)
        Medically Speaking Ethers as Inhalation    638 (1)
        Anesthetics
      14.4 Crown Ethers                            639 (2)
        Medically Speaking Polyether Antibiotics   641 (1)
      14.5 Preparation of Ethers                   641 (3)
      14.6 Reactions of Ethers                     644 (3)
      14.7 Nomenclature of Epoxides                647 (1)
        Medically Speaking Epothilones as Novel    648 (1)
        Anticancer Agents
      14.8 Preparation of Epoxides                 648 (4)
        Medically Speaking Active Metabolites      651 (1)
        and Drug Interactions
      14.9 Enantioselective Epoxidation            652 (2)
      14.10 Ring-Opening Reactions of Epoxides     654 (9)
        Practically Speaking Ethylene Oxide as     657 (5)
        a Sterilizing Agent for Sensitive
        Medical Equipment
        Medically Speaking Cigarette Smoke and     662 (1)
        Carcinogenic Epoxides
      14.11 Thiols and Sulfides                    663 (4)
      14.12 Synthesis Strategies Involving         667 (16)
      Epoxides
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practifce Problems
        Integrated Problems
        Challenge Problems
    15 Infrared Spectroscopy and Mass              683 (48)
    Spectrometry
      15.1 Introduction to Spectroscopy            684 (2)
        Practically Speaking Microwave Ovens       686 (1)
      15.2 IR Spectroscopy                         686 (3)
        Medically Speaking IR Thermal Imaging      687 (2)
        for Cancer Detection
      15.3 Signal Characteristics: Wavenumber      689 (4)
      15.4 Signal Characteristics: Intensity       693 (3)
        Practically Speaking IR Spectroscopy       696 (1)
        for Testing Blood Alcohol Levels
      15.5 Signal Characteristics: Shape           696 (4)
      15.6 Analyzing an IR Spectrum                700 (5)
      15.7 Using IR Spectroscopy to Distinguish    705 (2)
      between Two Compounds
      15.8 Introduction to Mass Spectrometry       707 (2)
        Practically Speaking Mass Spectrometry     708 (1)
        for Detecting Explosives
      15.9 Analyzing the (M)+· Peak         709 (1)
      15.10 Analyzing the (M+1)+· Peak      710 (2)
      15.11 Analyzing the (M+2)+· Peak      712 (2)
      15.12 Analyzing the Fragments                714 (3)
      15.13 High Resolution Mass Spectrometry      717 (2)
      15.14 Gas Chromatography---Mass              719 (1)
      Spectrometry
      15.15 Mass Spectrometry of Large             720 (1)
      Biomolecules
        Medically Speaking Medical Applications    720 (1)
        of Mass Spectrometry
      15.16 Hydrogen Deficiency Index: Degrees     721 (10)
      of Unsaturation
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    16 Nuclear Magnetic Resonance Spectroscopy     731 (51)
      16.1 Introduction to NMR Spectroscopy        732 (2)
      16.2 Acquiring a 1H NMR Spectrum             734 (2)
      16.3 Characteristics of a 1H NMR Spectrum    736 (1)
      16.4 Number of Signals                       736 (7)
      16.5 Chemical Shift                          743 (6)
      16.6 Integration                             749 (3)
      16.7 Multiplicity                            752 (8)
      16.8 Drawing the Expected 1H NMR Spectrum    760 (2)
      of a Compound
      16.9 Using 1H NMR Spectroscopy to            762 (2)
      Distinguish between Compounds
        Medically Speaking Detection of            764 (1)
        Impurities in Heparin Sodium Using 1H
        NMR Spectroscopy
      16.10 Analyzing a 1H NMR Spectrum            764 (3)
      16.11 Acquiring a 13C NMR Spectrum           767 (1)
      16.12 Chemical Shifts in 13C NMR             768 (2)
      Spectroscopy
      16.13 DEPT 13C NMR Spectroscopy              770 (12)
        Medically Speaking Magnetic Resonance      772 (10)
        Imaging (MRI)
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    17 Conjugated Pi Systems and Pericyclic        782 (50)
    Reactions
      17.1 Classes of Dienes                       783 (1)
      17.2 Conjugated Dienes                       784 (2)
      17.3 Molecular Orbital Theory                786 (4)
      17.4 Electrophilic Addition                  790 (3)
      17.5 Thermodynamic Control vs. Kinetic       793 (4)
      Control
        Practically Speaking Natural and           796 (1)
        Synthetic Rubbers
      17.6 An Introduction to Pericyclic           797 (1)
      Reactions
      17.7 Diels--Alder Reactions                  798 (6)
      17.8 MO Description of Cycloadditions        804 (2)
      17.9 Electrocyclic Reactions                 806 (6)
      17.10 Sigmatropic Rearrangements             812 (2)
        Medically Speaking The Photoinduced        814 (1)
        Biosynthesis of Vitamin D
      17.11 UV-VIS Spectroscopy                    814 (6)
        Practically Speaking Sunscreens            819 (1)
      17.12 Color                                  820 (1)
        Practically Speaking Bleach                820 (1)
      17.13 The Chemistry of Vision                821 (11)
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    18 Aromatic Compounds                          832 (42)
      18.1 Introduction to Aromatic Compounds      833 (1)
        Practically Speaking What Is Coal?         834 (1)
      18.2 Nomenclature of Benzene Derivatives     834 (4)
      18.3 Structure of Benzene                    838 (1)
      18.4 Stability of Benzene                    838 (7)
        Practically Speaking Molecular Cages       843 (2)
      18.5 Aromatic Compounds Other than Benzene   845 (9)
        Medically Speaking The Development of      852 (2)
        Nonsedating Antihistamines
      18.6 Reactions at the Benzylic Position      854 (4)
      18.7 Reduction of the Aromatic Moiety        858 (3)
      18.8 Spectroscopy of Aromatic Compounds      861 (13)
        Practically Speaking Buckyballs and        864 (10)
        Nanotubes
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    19 Aromatic Substitution Reactions             874 (57)
      19.1 Introduction to Electrophilic           875 (1)
      Aromatic Substitution
      19.2 Halogenation                            876 (3)
        Medically Speaking Halogenation in Drug    879 (1)
        Design
      19.3 Sulfonation                             879 (3)
        Practically Speaking What Are Those        881 (1)
        Colors in Fruity Pebbles?
      19.4 Nitration                               882 (1)
      19.5 Friedel--Crafts Alkylation              883 (4)
        Medically Speaking The Discovery of        884 (3)
        Prodrugs
      19.6 Friedel-Crafts Acylation                887 (2)
      19.7 Activating Groups                       889 (4)
      19.8 Deactivating Groups                     893 (2)
      19.9 Halogens: The Exception                 895 (2)
      19.10 Determining the Directing effects      897 (3)
      of a Substituent
      19.11 Multiple Substituents                  900 (7)
      19.12 Synthesis Strategies                   907 (7)
      19.13 Nucleophilic Aromatic Substitution     914 (2)
      19.14 Elimination-Addition                   916 (2)
      19.15 Identifying the Mechanism of an        918 (13)
      Aromatic Substitution Reaction
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    20 Aldehydes and Ketones                       931 (53)
      20.1 Introduction to Aldehydes and Ketones   932 (1)
      20.2 Nomenclature                            933 (3)
      20.3 Preparing Aldehydes and Ketones: A      936 (1)
      Review
      20.4 Introduction to Nucleophilic            937 (2)
      Addition Reactions
      20.5 Oxygen Nucleophiles                     939 (8)
        Medically Speaking Acetals as Prodrugs     946 (1)
      20.6 Nitrogen Nucleophiles                   947 (9)
        Practically Speaking Beta-Carotene and     951 (5)
        Vision
      20.7 Hydrolysis of Acetals, Imines, and      956 (3)
      Enamines
        Medically Speaking Prodrugs                958 (1)
      20.8 Sulfur Nucleophiles                     959 (1)
      20.9 Hydrogen Nucleophiles                   960 (2)
      20.10 Carbon Nucleophiles                    962 (5)
        Practically Speaking Cyanohydrin           964 (3)
        Derivatives in Nature
      20.11 Baeyer-Villiger Oxidation of           967 (2)
      Aldehydes and Ketones
      20.12 Synthesis Strategies                   969 (3)
      20.13 Spectroscopic Analysis of Aldehydes    972 (12)
      and Ketones
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    21 Carboxylic Acids and Their Derivatives      984 (60)
      21.1 Introduction to Carboxylic Acids        985 (1)
      21.2 Nomenclature of Carboxylic Acids        986 (1)
      21.3 Structure and Properties of             987 (4)
      Carboxylic Acids
      21.4 Preparation of Carboxylic Acids         991 (1)
      21.5 Reactions of Carboxylic Acids           992 (1)
      21.6 Introduction to Carboxylic Acid         993 (4)
      Derivatives
        Medically Speaking Sedatives               995 (2)
      21.7 Reactivity of Carboxylic Acid           997 (8)
      Derivatives
      21.8 Preparation and Reactions of Acid       1005(6)
      Chlorides
      21.9 Preparation and Reactions of Acid       1011(2)
      Anhydrides
        Medically Speaking How does Aspirin        1013(1)
        Work?
      21.10 Preparation of Esters                  1013(2)
      21.11 Reactions of Esters                    1015(5)
        Practically Speaking How Soap Is Made      1016(2)
        Medically Speaking Esters as Prodrugs      1018(2)
      21.12 Preparation and Reactions of Amides    1020(5)
        Practically Speaking Polyamides and        1021(3)
        Polyesters
        Medically Speaking Beta-Lactam             1024(1)
        Antibiotics
      21.13 Preparation and Reactions of           1025(2)
      Nitriles
      21.14 Synthesis Strategies                   1027(6)
      21.15 Spectroscopy of Carboxylic Acids       1033(11)
      and Their Derivatives
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    22 Alpha Carbon Chemistry: Enols and           1044(58)
    Enolates
      22.1 Introduction to Alpha Carbon            1045(7)
      Chemistry: Enols and Enolates
      22.2 Alpha Halogenation of Enols and         1052(5)
      Enolates
      22.3 Aldol Reactions                         1057(11)
        Practically Speaking Muscle Power          1060(4)
        Practically Speaking Why Meat from         1064(4)
        Younger Animals is Softer
      22.4 Claisen Condensations                   1068(3)
      22.5 Alkylation of the Alpha Position        1071(8)
      22.6 Conjugate Addition Reactions            1079(7)
        Medically Speaking Glutathione             1082(4)
        Conjugation and Biological Michael
        Reactions
      22.7 Synthesis Strategies                    1086(16)
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    23 Amines                                      1102(49)
      23.1 Introduction to Amines                  1103(2)
        Medically Speaking Drug Metabolism         1104(1)
        Studies
      23.2 Nomenclature of Amines                  1105(2)
      23.3 Properties of Amines                    1107(7)
        Medically Speaking Fortunate Side          1109(5)
        Effects
        Medically Speaking Amine Ionization and    1114(1)
        Drug Distribution
      23.4 Preparation of Amines: A Review         1114(1)
      23.5 Preparation of Amines via               1115(4)
      Substitution Reactions
      23.6 Preparation of Amines via Reductive     1119(2)
      Amination
      23.7 Synthesis Strategies                    1121(3)
      23.8 Acylation of Amines                     1124(1)
      23.9 The Hofmann Elimination                 1125(3)
      23.10 Reactions of Amines with Nitrous       1128(3)
      Acid
      23.11 Reactions of Aryldiazonium Ions        1131(4)
      23.12 Nitrogen Heterocycles                  1135(3)
        Medically Speaking H2-Receptor             1136(2)
        Antagonists and the Development of
        Cimetidine
      23.13 Spectroscopy of Amines                 1138(13)
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    24 Carbohydrates                               1151(42)
      24.1 Introduction to Carbohydrates           1152(1)
      24.2 Classifying Monosaccharides             1152(3)
      24.3 Configuration of Aldoses                1155(2)
      24.4 Configuration of Ketoses                1157(1)
      24.5 Cyclic Structures of Monosaccharides    1158(8)
      24.6 Reactions of Monosaccharides            1166(7)
      24.7 Disaccharides                           1173
        Medically Speaking Lactose Intolerance     1176(1)
        Practically Speaking Artificial            1177(1)
        Sweeteners
      24.8 Polysaccharides                         1178
      24.9 Amino Sugars                            1179(1)
      24.10 N-Glycosides                           1180(13)
        Medically Speaking Aminoglycoside          1181(4)
        Antibiotics
        Medically Speaking Erythromycin            1185(8)
        Biosynthesis
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    25 Amino Acids, Peptides, and Proteins         1193(46)
      25.1 Introduction to Amino Acids,            1194(1)
      Peptides, and Proteins
      25.2 Structure and Properties of Amino       1195(7)
      Acids
        Practically Speaking Nutrition and         1197(5)
        Sources of Amino Acids
        Practically Speaking Forensic Chemistry    1202(1)
        and Fingerprint Detection
      25.3 Amino Acid Synthesis                    1202(5)
      25.4 Structure of Peptides                   1207(7)
        Medically Speaking Polypeptide             1213(1)
        Antibiotics
      25.5 Sequencing a Peptide                    1214(2)
      25.6 Peptidexs Synthesis                     1216(9)
      25.7 Protein Structure                       1225(4)
        Medically Speaking Diseases Caused by      1228(1)
        Misfolded Proteins
      25.8 Protein Function                        1229(10)
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuildfer Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    26 Lipids                                      1239(40)
      26.1 Introduction to Lipids                  1240(1)
      26.2 Waxes                                   1241(1)
      26.3 Triglycerides                           1242(3)
      26.4 Reactions of Triglycerides              1245(9)
        Practically Speaking Soaps vs.             1250(4)
        Synthetic Detergents
      26.5 Phospholipids                           1254(4)
        Medically Speaking Selectivity of          1257(1)
        Antifungal Agents
      26.6 Steroids                                1258(7)
        Medically Speaking Cholesterol and         1261(3)
        Heart Disease
        Medically Speaking Anabolic Steroids       1264(1)
        and Competitive Sports
      26.7 Prostaglandins                          1265(3)
        Medically Speaking NSAIDs and COX-2        1267(1)
        Inhibitors
      26.8 Terpenes                                1268(11)
        Review of Synthetically Useful Reactions
        RevieW of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
    27 Synthetic Polymers                          1279
      27.1 Introduction to Synthetic Polymers      1280(1)
      27.2 Nomenclature of Synthetic Polymers      1280(2)
      27.3 Copolymers                              1282(2)
      27.4 Polymer Classification by Reaction      1284(8)
      Type
      27.5 Polymer Classification by Mode of       1292(2)
      Assembly
      27.6 Polymer Classification by Structure     1294(3)
      27.7 Polymer Classification by Properties    1297(2)
        Practically Speaking Safety Glass and      1299(1)
        Car Windshields
      27.8 Polymer Recycling                       1299
        Review of Reactions
        Review of Concepts & Vocabulary
        SkillBuilder Review
        Practice Problems
        Integrated Problems
        Challenge Problems
Appendix A Nomenclature of Polyfunctional          1   (1)
Compounds
Glossary                                           1   (1)
Credits                                            1   (1)
Index                                              1