Organic Chemistry 12th Edition by Graham Solomons , Craig Fryhle , Scott Snyder ISBN 1118875761 978-1118875766

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ISBN 10: 1118875761 
ISBN 13: 978-1118875766
Author: T. W. Graham Solomons , Craig B. Fryhle , Scott A. Snyder 

The 12th edition of Organic Chemistry continues Solomons, Fryhle & Snyder’s tradition of excellence in teaching and preparing students for success in the organic classroom and beyond.

A central theme of the authors’ approach to organic chemistry is to emphasize the relationship between structure and reactivity. To accomplish this, the content is organized in a way that combines the most useful features of a functional group approach with one largely based on reaction mechanisms. The authors’ philosophy is to emphasize mechanisms and their common aspects as often as possible, and at the same time, use the unifying features of functional groups as the basis for most chapters. The structural aspects of the authors’ approach show students what organic chemistry is. Mechanistic aspects of their approach show students how it works. And wherever an opportunity arises, the authors’ show students what it does in living systems and the physical world around us.

Organic Chemistry 12th Table of contents:

1 The Basics: BONDING AND MOLECULAR STRUCTURE

1.1 Life and the Chemistry of Carbon Compounds—We Are Stardust

THE CHEMISTRY OF… Natural Products

1.2 Atomic Structure

1.3 Chemical Bonds: The Octet Rule

1.4 HOW TO Write Lewis Structures

1.5 Formal Charges and HOW TO Calculate Them

1.6 Isomers: Different Compounds that Have the Same Molecular Formula

1.7 HOW TO Write and Interpret Structural Formulas

1.8 Resonance Theory

1.9 Quantum Mechanics and Atomic Structure

1.10 Atomic Orbitals and Electron Configuration

1.11 Molecular Orbitals

1.12 The Structure of Methane and Ethane: sp[sup(3)] Hybridization

THE CHEMISTRY OF… Calculated Molecular Models: Electron Density Surfaces

1.13 The Structure of Ethene (Ethylene): sp[sup(2)] Hybridization

1.14 The Structure of Ethyne (Acetylene): sp Hybridization

1.15 A Summary of Important Concepts that Come from Quantum Mechanics

1.16 HOW TO Predict Molecular Geometry: The Valence Shell Electron Pair Repulsion Model

1.17 Applications of Basic Principles

[ WHY DO THESE TOPICS MATTER? ]

2 Families of Carbon Compounds: FUNCTIONAL GROUPS, INTERMOLECULAR FORCES, AND INFRARED (IR) SPECTROS

2.1 Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds

2.2 Polar Covalent Bonds

2.3 Polar and Nonpolar Molecules

2.4 Functional Groups

2.5 Alkyl Halides or Haloalkanes

2.6 Alcohols and Phenols

2.7 Ethers

THE CHEMISTRY OF… Ethers as General Anesthetics

2.8 Amines

2.9 Aldehydes and Ketones

2.10 Carboxylic Acids, Esters, and Amides

2.11 Nitriles

2.12 Summary of Important Families of Organic Compounds

2.13 Physical Properties and Molecular Structure

THE CHEMISTRY OF… Fluorocarbons and Teflon

2.14 Summary of Attractive Electric Forces

THE CHEMISTRY OF… Organic Templates Engineered to Mimic Bone Growth

2.15 Infrared Spectroscopy: An Instrumental Method for Detecting Functional Groups

2.16 Interpreting IR Spectra

2.17 Applications of Basic Principles

[ WHY DO THESE TOPICS MATTER? ]

3 Acids and Bases: AN INTRODUCTION TO ORGANIC REACTIONS AND THEIR MECHANISMS

3.1 Acid–Base Reactions

3.2 HOW TO use Curved Arrows in Illustrating Reactions

[ A MECHANISM FOR THE REACTION ] Reaction of Water with Hydrogen Chloride: The use of Curved Arrows

3.3 Lewis Acids and Bases

3.4 Heterolysis of Bonds to Carbon: Carbocations and Carbanions

3.5 The Strength of Brønsted–Lowry Acids and Bases: K[sub(a)] and pK[sub(a)]

3.6 HOW TO Predict the Outcome of Acid–Base Reactions

3.7 Relationships between Structure and Acidity

3.8 Energy Changes

3.9 The Relationship between the Equilibrium Constant and the Standard Free-Energy Change, ∆G°

3.10 Acidity: Carboxylic Acids versus Alcohols

3.11 The Effect of the Solvent on Acidity

3.12 Organic Compounds as Bases

3.13 A Mechanism for an Organic Reaction

[ A MECHANISM FOR THE REACTION ] Reaction of tert-Butyl Alcohol with Concentrated Aqueous HCl

3.14 Acids and Bases in Nonaqueous Solutions

3.15 Acid–Base Reactions and the Synthesis of Deuterium- and Tritium-Labeled Compounds

3.16 Applications of Basic Principles

[ WHY DO THESE TOPICS MATTER? ]

4 Nomenclature and Conformations of Alkanes and Cycloalkanes

4.1 Introduction to Alkanes and Cycloalkanes

THE CHEMISTRY OF… Petroleum Refining

4.2 Shapes of Alkanes

4.3 HOW TO Name Alkanes, Alkyl Halides, and Alcohols: The Iu PAC System

4.4 HOW TO Name Cycloalkanes

4.5 HOW TO Name Alkenes and Cycloalkenes

4.6 HOW TO Name Alkynes

4.7 Physical Properties of Alkanes and Cycloalkanes

THE CHEMISTRY OF… Pheromones: Communication by Means of Chemicals

4.8 Sigma Bonds and Bond Rotation

4.9 Conformational Analysis of Butane

THE CHEMISTRY OF… Muscle Action

4.10 The Relative Stabilities of Cycloalkanes: Ring Strain

4.11 Conformations of Cyclohexane: The Chair and the Boat

THE CHEMISTRY OF… Nanoscale Motors and Molecular Switches

4.12 Substituted Cyclohexanes: Axial and Equatorial Hydrogen Groups

4.13 Disubstituted Cycloalkanes: Cis–Trans Isomerism

4.14 Bicyclic and Polycyclic Alkanes

4.15 Chemical Reactions of Alkanes

4.16 Synthesis of Alkanes and Cycloalkanes

4.17 HOW TO Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency

4.18 Applications of Basic Principles

[ WHY DO THESE TOPICS MATTER? ]

SPECIAL TOPIC A: [sup(13)]C NMR Spectroscopy—a Practical Introduction

5 Stereochemistry: CHIRAL MOLECULES

5.1 Chirality and Stereochemistry

5.2 Isomerism: Constitutional Isomers and Stereoisomers

5.3 Enantiomers and Chiral Molecules

5.4 Molecules Having One Chirality Center are Chiral

5.5 More about the Biological Importance of Chirality

5.6 HOW TO Test for Chirality: Planes of Symmetry

5.7 Naming Enantiomers: The R,S-System

5.8 Properties of Enantiomers: Optical Activity

5.9 Racemic Forms

5.10 The Synthesis of Chiral Molecules

5.11 Chiral Drugs

THE CHEMISTRY OF… Selective Binding of Drug Enantiomers to Left- and Right-Handed Coiled DNA

5.12 Molecules with More than One Chirality Center

5.13 Fischer Projection Formulas

5.14 Stereoisomerism of Cyclic Compounds

5.15 Relating Configurations through Reactions in Which No Bonds to the Chirality Center Are Broke

5.16 Separation of Enantiomers: Resolution

5.17 Compounds with Chirality Centers Other than Carbon

5.18 Chiral Molecules that Do Not Possess a Chirality Center

[ WHY DO THESE TOPICS MATTER? ]

6 Nucleophilic Reactions: PROPERTIES AND SUBSTITUTION REACTIONS OF ALKYL HALIDES

6.1 Alkyl Halides

6.2 Nucleophilic Substitution Reactions

6.3 Nucleophiles

6.4 Leaving Groups

6.5 Kinetics of a Nucleophilic Substitution Reaction: An S[sub(N)]2 Reaction

6.6 A Mechanism for the S[sub(N)]2 Reaction

[ A MECHANISM FOR THE REACTION ] Mechanism for the S N 2 Reaction

6.7 Transition State Theory: Free-Energy Diagrams

6.8 The Stereochemistry of S[sub(N)]2 Reactions

[ A MECHANISM FOR THE REACTION ] The Stereochemistry of an S[sub(N)]2 Reaction

6.9 The Reaction of tert-Butyl Chloride with Water: An S[sub(N)]1 Reaction

6.10 A Mechanism for the S[sub(N)]1 Reaction

[ A MECHANISM FOR THE REACTION ] Mechanism for the S[sub(N)]1 Reaction

6.11 Carbocations

6.12 The Stereochemistry of S[sub(N)]1 Reactions

[ A MECHANISM FOR THE REACTION ] The Stereochemistry of an S[sub(N)]1 Reaction

6.13 Factors Affecting the Rates of S[sub(N)]1 and S[sub(N)]2 Reactions

6.14 Organic Synthesis: Functional Group Transformations Using S[sub(N)]2 Reactions

THE CHEMISTRY OF… Biological Methylation: A Biological Nucleophilic Substitution Reaction

[ WHY DO THESE TOPICS MATTER? ]

7 Alkenes and Alkynes I: PROPERTIES AND SYNTHESIS. ELIMINATION REACTIONS OF ALKYL HALIDES

7.1 Introduction

7.2 The (E)–(Z) System for Designating Alkene Diastereomers

7.3 Relative Stabilities of Alkenes

7.4 Cycloalkenes

7.5 Synthesis of Alkenes: Elimination Reactions

7.6 Dehydrohalogenation

7.7 The E2 Reaction

[ A MECHANISM FOR THE REACTION ] Mechanism for the E2 Reaction

[ A MECHANISM FOR THE REACTION ] E2 Elimination Where There Are Two Axial β Hydrogens

[ A MECHANISM FOR THE REACTION ] E2 Elimination Where the Only Axial β Hydrogen Is from a Less Stab

7.8 The E1 Reaction

[ A MECHANISM FOR THE REACTION ] Mechanism for the E1 Reaction

7.9 Elimination and Substitution Reactions Compete With Each Other

7.10 Elimination of Alcohols: Acid-Catalyzed Dehydration

[ A MECHANISM FOR THE REACTION ] Acid-Catalyzed Dehydration of Secondary or Tertiary Alcohols: An E1

[ A MECHANISM FOR THE REACTION ] Dehydration of a Primary Alcohol: An E2 Reaction

7.11 Carbocation Stability and the Occurrence of  Molecular Rearrangements

[ A MECHANISM FOR THE REACTION ] Formation of a Rearranged Alkene During Dehydration of a Primary Al

7.12 The Acidity of Terminal Alkynes

7.13 Synthesis of Alkynes by Elimination Reactions

[ A MECHANISM FOR THE REACTION ] Dehydrohalogenation of vic-Dibromides to Form Alkynes

7.14 Terminal Alkynes Can Be Converted to Nucleophiles for Carbon–Carbon Bond Formation

7.15 Hydrogenation of Alkenes

THE CHEMISTRY OF… Hydrogenation in the Food Industry

7.16 Hydrogenation: The Function of the Catalyst

7.17 Hydrogenation of Alkynes

[ A MECHANISM FOR THE REACTION ] The Dissolving Metal Reduction of an Alkyne

7.18 An Introduction to Organic Synthesis

THE CHEMISTRY OF… From the Inorganic to the Organic

[ WHY DO THESE TOPICS MATTER? ]

8 Alkenes and Alkynes II: ADDITION REACTIONS

8.1 Addition Reactions of Alkenes

8.2 Electrophilic Addition of Hydrogen Halides to Alkenes: Mechanism and Markovnikov’s Rule

[ A MECHANISM FOR THE REACTION ] Addition of a Hydrogen Halide to an Alkene

[ A MECHANISM FOR THE REACTION ] Addition of HBr to 2-Methylpropene

8.3 Stereochemistry of the Ionic Addition to an Alkene

[ THE STEREOCHEMISTRY OF THE REACTION ] Ionic Addition to an Alkene

8.4 Addition of Water to Alkenes: Acid-Catalyzed Hydration

[ A MECHANISM FOR THE REACTION ] Acid-Catalyzed Hydration of an Alkene

8.5 Alcohols from Alkenes through Oxymer curation– Demer curation: Markovnikov Addition

[ A MECHANISM FOR THE REACTION ] Oxymercuration

8.6 Alcohols from Alkenes through Hydroboration– Oxidation: Anti-Markovnikov Syn Hydration

8.7 Hydroboration: Synthesis of Alkylboranes

[ A MECHANISM FOR THE REACTION ] Hydroboration

8.8 Oxidation and Hydrolysis of Alkylboranes

[ A MECHANISM FOR THE REACTION ] Oxidation of Trialkylboranes

8.9 Summary of Alkene Hydration Methods

8.10 Protonolysis of Alkylboranes

8.11 Electrophilic Addition of Bromine and Chlorine to Alkenes

[ A MECHANISM FOR THE REACTION ] Addition of Bromine to an Alkene

THE CHEMISTRY OF… The Sea: A Treasury of Biologically Active Natural Products

8.12 Ster eospecific Reactions

[ THE STEREOCHEMISTRY OF THE REACTION ] Addition of Bromine to cis- and trans-2-Butene

8.13 Halohydrin Formation

[ A MECHANISM FOR THE REACTION ] Halohydrin Formation from an Alkene

THE CHEMISTRY OF… Citrus-Flavored Soft Drinks

8.14 Divalent Carbon Compounds: Carbenes

8.15 Oxidation of Alkenes: Syn 1,2-Dihydroxylation

THE CHEMISTRY OF… Catalytic Asymmetric Dihydroxylation

8.16 Oxidative Cleavage of Alkenes

[ A MECHANISM FOR THE REACTION ] Ozonolysis of an Alkene

8.17 Electrophilic Addition of Bromine and Chlorine to Alkynes

8.18 Addition of Hydrogen Halides to Alkynes

8.19 Oxidative Cleavage of Alkynes

8.20 HOW TO Plan a Synthesis: Some Approaches and Examples

[ WHY DO THESE TOPICS MATTER? ]

9 Nuclear Magnetic Resonance and Mass Spectrometry: TOOLS FOR STRUCTURE DETERMINATION

9.1 Introduction

9.2 Nuclear Magnetic Resonance (NMR) Spectroscopy

9.3 HOW TO Interpret Proton NMR Spectra

9.4 Shielding and Deshielding of Protons: More about Chemical Shift

9.5 Chemical Shift Equivalent and Nonequivalent Protons

9.6 Spin–Spin Coupling: More about Signal Splitting and Nonequivalent or Equivalent Protons

9.7 Proton NMR Spectra and Rate Processes

9.8 Carbon-13 NMR Spectroscopy

9.9 Two-Dimensional (2D) NMR Techniques

THE CHEMISTRY OF… Magnetic Resonance Imaging in Medicine

9.10 An Introduction to Mass Spectrometry

9.11 Formation of Ions: Electron Impact Ionization

9.12 Depicting the Molecular Ion

9.13 Fragmentation

9.14 Isotopes in Mass Spectra

9.15 GC/MS Analysis

9.16 Mass Spectrometry of Biomolecules

[ WHY DO THESE TOPICS MATTER? ]

SPECIAL TOPIC B: NMR Theory and Instrumentation

10 Radical Reactions

10.1 Introduction: How Radicals Form and How They React

[ A MECHANISM FOR THE REACTION ] Hydrogen Atom Abstraction

[ A MECHANISM FOR THE REACTION ] Radical Addition to a π Bond

THE CHEMISTRY OF… Acne Medications

10.2 Homolytic Bond Dissociation Energies (DH°)

10.3 Reactions of Alkanes with Halogens

10.4 Chlorination of Methane: Mechanism of Reaction

[ A MECHANISM FOR THE REACTION ] Radical Chlorination of Methane

10.5 Halogenation of Higher Alkanes

[ A MECHANISM FOR THE REACTION ] Radical Halogenation of Ethane

10.6 The Geometry of Alkyl Radicals

10.7 Reactions that Generate Tetrahedral Chirality Centers

[ A MECHANISM FOR THE REACTION ] The Stereochemistry of Chlorination at C2 of Pentane

[ A MECHANISM FOR THE REACTION ] The Stereochemistry of Chlorination at C3 of (S)-2-Chloropentane

10.8 Allylic Substitution and Allylic Radicals

10.9 Benzylic Substitution and Benzylic Radicals

10.10 Radical Addition to Alkenes: The Anti-Markovnikov Addition of Hydrogen Bromide

[ A MECHANISM FOR THE REACTION ] Anti- Markovnikov Addition of HBr

10.11 Radical Polymerization of Alkenes: Chain-Growth Polymers

[ A MECHANISM FOR THE REACTION ] Radical Polymerization of Ethene (Ethylene)

10.12 Other Important Radical Reactions

THE CHEMISTRY OF… Antioxidants

THE CHEMISTRY OF… Ozone Depletion and Chlorofluorocarbons (CFCs)

[ WHY DO THESE TOPICS MATTER? ]

SPECIAL TOPIC C: Chain-Growth Polymers

11 Alcohols and Ethers: SYNTHESIS AND REACTIONS

11.1 Structur eand Nomenclature

11.2 Physical Properties of Alcohols and Ethers

11.3 Important Alcohols and Ethers

THE CHEMISTRY OF… Ethanol as a Biofuel

THE CHEMISTRY OF… Cholesterol and Heart Disease

11.4 Synthesis of Alcohols from Alkenes

11.5 Reactions of Alcohols

11.6 Alcohols as Acids

11.7 Conversion of Alcohols into Alkyl Halides

11.8 Alkyl Halides from the Reaction of Alcohols with Hydr ogen Halides

11.9 Alkyl Halides from the Reaction of Alcohols with PBr[sub(3)]  or SOCl[sub(2)]

11.10 Tosylates, Mesylates, and Triflates: Leaving Group Derivatives of Alcohols

[ A MECHANISM FOR THE REACTION ] Conversion of an Alcohol into a Mesylate (an Alkyl Methanesulfonate

11.11 Synthesis of Ethers

[ A MECHANISM FOR THE REACTION ] Intermolecular Dehydration of  Alcohols to Form an Ether

[ A MECHANISM FOR THE REACTION ] The Williamson Ether Synthesis

11.12 Reactions of Ethers

[ A MECHANISM FOR THE REACTION ] Ether Cleavage by Strong Acids

11.13 Epoxides

[ A MECHANISM FOR THE REACTION ] Alkene Epoxidation

THE CHEMISTRY OF… The Sharpless Asymmetric Epoxidation

11.14 Reactions of Epoxides

[ A MECHANISM FOR THE REACTION ] Acid-Catalyzed Ring Opening of an Epoxide

[ A MECHANISM FOR THE REACTION ] Base-Catalyzed Ring Opening of an Epoxide

11.15 Anti 1,2-Dihydroxylation of Alkenes via Epoxides

THE CHEMISTRY OF… Environmentally Friendly Alkene Oxidation Methods

11.16 Crown Ethers

THE CHEMISTRY OF… Transport Antibiotics and Crown Ethers

11.17 Summary of Reactions of Alkenes, Alcohols, and Ethers

[ WHY DO THESE TOPICS MATTER? ]

12 Alcohols from Carbonyl Compounds: OXIDATION–REDUCTION AND ORGANOMETALLIC COMPOUNDS

12.1 Structure of the Carbonyl Group

12.2 Oxidation–Reduction Reactions in Organic Chemistry

12.3 Alcohols by Reduction of Carbonyl Compounds

[ A MECHANISM FOR THE REACTION ] Reduction of Aldehydes and Ketones by Hydride Transfer

THE CHEMISTRY OF… Alcohol Dehydrogenase— A Biochemical Hydride Reagent

THE CHEMISTRY OF… Stereoselective Reductions of Carbonyl Groups

12.4 Oxidation of Alcohols

[ A MECHANISM FOR THE REACTION ] The Swern Oxidation

[ A MECHANISM FOR THE REACTION ] Chromic Acid Oxidation

12.5 Organometallic Compounds

12.6 Preparation of Organolithium and Organomagnesium Compounds

12.7 Reactions of Organolithium and Organomagnesium Compounds

[ A MECHANISM FOR THE REACTION ] The Grignard Reaction

12.8 Alcohols from Grignard Reagents

12.9 Protecting Groups

[ WHY DO THESE TOPICS MATTER? ]

FIRST REVIEW PROBLEM SET

13 Conjugated Unsaturated Systems

13.1 Introduction

13.2 The Stability of the Allyl Radical

13.3 The Allyl Cation

13.4 Resonance Theory Revisited

13.5 Alkadienes and Polyunsaturated Hydrocarbons

13.6 1,3-Butadiene: Electron Delocalization

13.7 The Stability of Conjugated Dienes

13.8 Ultraviolet–Visible Spectroscopy

13.9 Electrophilic Attack on Conjugated Dienes: 1,4-Addition

13.10 The Diels–Alder Reaction: A 1,4-Cycloaddition Reaction of Dienes

THE CHEMISTRY OF… Molecules with the Nobel Prize in Their Synthetic Lineage

[ WHY DO THESE TOPICS MATTER? ]

14 Aromatic Compounds

14.1 The Discovery of Benzene

14.2 Nomenclature of Benzene Derivatives

14.3 Reactions of Benzene

14.4 The Kekulé Structure for Benzene

14.5 The Thermodynamic Stability of Benzene

14.6 Modern Theories of the Structure of Benzene

14.7 Hückel’s Rule: The 4n + 2 Electron Rule

14.8 Other Aromatic Compounds

THE CHEMISTRY OF… Nanotubes

14.9 Heterocyclic Aromatic Compounds

14.10 Aromatic Compounds in Biochemistry

THE CHEMISTRY OF… Aryl Halides: Their uses and Environmental Concerns

14.11 Spectroscopy of Aromatic Compounds

THE CHEMISTRY OF… Sunscreens (Catching the Sun’s Rays and What  Happens to Them)

[ WHY DO THESE TOPICS MATTER? ]

SPECIAL TOPIC D, Electrocyclic and Cycloaddition Reactions

15 Reactions of Aromatic Compounds

15.1 Electrophilic Aromatic Substitution Reactions

15.2 A General Mechanism for Electrophilic Aromatic Substitution

15.3 Halogenation of Benzene

[ A MECHANISM FOR THE REACTION ] Electrophilic Aromatic Bromination

15.4 Nitration of Benzene

[ A MECHANISM FOR THE REACTION ] Nitration of Benzene

15.5 Sulfonation of Benzene

[ A MECHANISM FOR THE REACTION ] Sulfonation of Benzene

15.6 Friedel–Crafts Reactions

[ A MECHANISM FOR THE REACTION ] Friedel–Crafts Alkylation

THE CHEMISTRY OF… Industrial Styrene Synthesis

[ A MECHANISM FOR THE REACTION ] Friedel–Crafts Acylation

15.7 Synthetic Applications of Friedel–Crafts Acylations: The Clemmensen and W olf f–Kishner Red

THE CHEMISTRY OF… DDT

15.8 Existing Substituents Direct the Position of Electrophilic Aromatic Substitution

15.9 Activating and Deactivating Effects: How Electron- Donating and Electron-Withdrawing Groups Aff

15.10 Directing Effects in Disubstituted Benzenes

15.11 Reactions of Benzene Ring Carbon Side Chains

15.12 Synthetic Strategies

15.13 The S N Ar Mechanism: Nucleophilic Aromatic Substitution  by  Addition-Elimination

[ A MECHANISM FOR THE REACTION ] The S [sub(N)]Ar Mechanism

THE CHEMISTRY OF… Bacterial Dehalogenation of a PCB Derivative

15.14 Benzyne: Nucleophilic Aromatic Substitution by  Elimination–Addition

[ A MECHANISM FOR THE REACTION ] The Benzyne Elimination–Addition Mechanism

THE CHEMISTRY OF… Host–Guest Trapping of Benzyne

15.15 Reduction of Aromatic Compounds

[ A MECHANISM FOR THE REACTION ] Birch Reduction

[ WHY DO THESE TOPICS MATTER? ]

16 Aldehydes and Ketones: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP

16.1 Introduction

16.2 Nomenclature of Aldehydes and Ketones

16.3 Physical Properties

THE CHEMISTRY OF… Aldehydes and Ketones in Perfumes

16.4 Synthesis of Aldehydes

[ A MECHANISM FOR THE REACTION ] Reduction of an Acyl Chloride to an Aldehyde

[ A MECHANISM FOR THE REACTION ] Reduction of an Ester to an Aldehyde

[ A MECHANISM FOR THE REACTION ] Reduction of a Nitrile to an Aldehyde

16.5 Synthesis of Ketones

16.6 Nucleophilic Addition to the Carbon–Oxygen Double Bond: Mechanistic Themes

[ A MECHANISM FOR THE REACTION ] Addition of a Strong Nucleophile to an Aldehyde or Ketone

[ A MECHANISM FOR THE REACTION ] Acid-Catalyzed Nucleophilic Addition to an Aldehyde or Ketone

16.7 The Addition of Alcohols: Hemiacetals and Acetals

[ A MECHANISM FOR THE REACTION ] Acid-Catalyzed Hemiacetal Formation

[ A MECHANISM FOR THE REACTION ] Acid-Catalyzed Acetal Formation

16.8 The Addition of Primary and Secondary Amines

[ A MECHANISM FOR THE REACTION ] Imine Formation

[ A MECHANISM FOR THE REACTION ] The Wolff–Kishner Reduction

[ A MECHANISM FOR THE REACTION ] Enamine Formation

THE CHEMISTRY OF… A Very Versatile Vitamin, Pyridoxine (Vitamin B[sub(6)])

16.9 The Addition of Hydrogen Cyanide: Cyanohydrins

[ A MECHANISM FOR THE REACTION ] Cyanohydrin Formation

16.10 The Addition of ylides: The Wittig Reaction

[ A MECHANISM FOR THE REACTION ] The Wittig Reaction

16.11 Oxidation of Aldehydes

16.12 The Baeyer–Villiger Oxidation

[ A MECHANISM FOR THE REACTION ] The Baeyer– Villiger Oxidation

16.13 Chemical Analyses for Aldehydes and Ketones

16.14 Spectroscopic Properties of Aldehydes and Ketones

16.15 Summary of Aldehyde and Ketone Addition Reactions

[ WHY DO THESE TOPICS MATTER? ]

17 Carboxylic Acids and Their Derivatives: NUCLEOPHILIC ADDITION– ELIMINATION AT THE ACYL CARBON

17.1 Introduction

17.2 Nomenclature and Physical Properties

17.3 Preparation of Carboxylic Acids

17.4 Acyl Substitution: Nucleophilic Addition–Elimination at the Acyl Carbon

[ A MECHANISM FOR THE REACTION ] Acyl Substitution by Nucleophilic Addition–Elimination

17.5 Acyl Chlorides

[ A MECHANISM FOR THE REACTION ] Synthesis of Acyl Chlorides using Thionyl Chloride

17.6 Carboxylic Acid Anhydrides

17.7 Esters

[ A MECHANISM FOR THE REACTION ] Acid-Catalyzed Esterification

[ A MECHANISM FOR THE REACTION ] Base-Promoted Hydrolysis of an Ester

17.8 Amides

[ A MECHANISM FOR THE REACTION ] DCC-Promoted Amide Synthesis

THE CHEMISTRY OF… Some Hot Topics Related to Structure and Activity

[ A MECHANISM FOR THE REACTION ] Acidic Hydrolysis of an Amide

[ A MECHANISM FOR THE REACTION ] Basic Hydrolysis of an Amide

[ A MECHANISM FOR THE REACTION ] Acidic Hydrolysis of a Nitrile

[ A MECHANISM FOR THE REACTION ] Basic Hydrolysis of a Nitrile

THE CHEMISTRY OF… Penicillins

17.9 Derivatives of Carbonic Acid

17.10 Decarboxylation of Carboxylic Acids

17.11 Polyesters and Polyamides: Step-Growth Polymers

17.12 Summary of the Reactions of Carboxylic Acids and Their Derivatives

[ WHY DO THESE TOPICS MATTER? ]

SPECIAL TOPIC E: Step-Growth Polymers

18 Reactions at the Carbon of Carbonyl Compounds: ENOLS AND ENOLATES

18.1 The Acidity of the Hydrogens of Carbonyl Compounds: Enolate Anions

18.2 Keto and Enol Tautomers

18.3 Reactions via Enols and Enolates

[ A MECHANISM FOR THE REACTION ] Base-Catalyzed Enolization

[ A MECHANISM FOR THE REACTION ] Acid-Catalyzed Enolization

[ A MECHANISM FOR THE REACTION ] Base-Promoted Halogenation of Aldehydes and Ketones

[ A MECHANISM FOR THE REACTION ] Acid-Catalyzed Halogenation of Aldehydes and Ketones

[ A MECHANISM FOR THE REACTION ] The Haloform Reaction

THE CHEMISTRY OF… Chloroform in Drinking Water

18.4 Lithium Enolates

18.5 Enolates of β-Dicarbonyl Compounds

18.6 Synthesis of Methyl Ketones: The Acetoacetic Ester Synthesis

18.7 Synthesis of Substituted Acetic Acids: The Malonic Ester Synthesis

[ A MECHANISM FOR THE REACTION ] The Malonic Ester Synthesis of Substituted Acetic Acids

18.8 Further Reactions of Active Hydrogen Compounds

18.9 Synthesis of Enamines: Stork Enamine Reactions

18.10 Summary of Enolate Chemistry

[ WHY DO THESE TOPICS MATTER? ]

19 Condensation and Conjugate Addition Reactions of Carbonyl Compounds: MORE CHEMISTRY OF ENOLATES

19.1 Introduction

19.2 The Claisen Condensation: A Synthesis of β-Keto Esters

[ A MECHANISM FOR THE REACTION ] The Claisen Condensation

[ A MECHANISM FOR THE REACTION ] The Dieckmann Condensation

19.3 β-Dicarbonyl Compounds by Acylation of Ketone Enolates

19.4 Aldol Reactions: Addition of Enolates and Enols to Aldehydes and Ketones

[ A MECHANISM FOR THE REACTION ] The Aldol Addition

[ A MECHANISM FOR THE REACTION ] Dehydration of the Aldol Addition Product

[ A MECHANISM FOR THE REACTION ] An Acid- Catalyzed Aldol Condensation

THE CHEMISTRY OF… A Retro-Aldol Reaction in Glycolysis—Dividing Assets to Double the ATP yield

19.5 Crossed Aldol Condensations

[ A MECHANISM FOR THE REACTION ] A Directed Aldol Synthesis using a Lithium Enolate

19.6 Cyclizations via Aldol Condensations

[ A MECHANISM FOR THE REACTION ] The Aldol Cyclization

THE CHEMISTRY OF… Polyketide Anticancer Antibiotic Biosynthesis

19.7 Additions to α,β-unsaturated Aldehydes and Ketones

[ A MECHANISM FOR THE REACTION ] The Conjugate Addition of HCN

[ A MECHANISM FOR THE REACTION ] The Conjugate Addition of an Amine

[ A MECHANISM FOR THE REACTION ] The Michael Addition

THE CHEMISTRY OF… Conjugate Additions to Activate Drugs

19.8 The Mannich Reaction

[ A MECHANISM FOR THE REACTION ] The Mannich Reaction

THE CHEMISTRY OF… A Suicide Enzyme Substrate

19.9 Summary of Important Reactions

[ WHY DO THESE TOPICS MATTER? ]

SPECIAL TOPIC F: Thiols, Sulfur Ylides, and Disulfides

SPECIAL TOPIC G: Thiol Esters and Lipid Biosynthesis

20 Amines

20.1 Nomenclature

20.2 Physical Properties and Structure of Amines

20.3 Basicity of Amines: Amine Salts

THE CHEMISTRY OF… Biologically Important Amines

20.4 Preparation of Amines

[ A MECHANISM FOR THE REACTION ] Reductive Amination

[ A MECHANISM FOR THE REACTION ] The Hofmann Rearrangement

20.5 Reactions of Amines

20.6 Reactions of Amines with Nitrous Acid

[ A MECHANISM FOR THE REACTION ] Diazotization

THE CHEMISTRY OF… N -Nitrosoamines

20.7 Replacement Reactions of Arenediazonium Salts

20.8 Coupling Reactions of Arenediazonium Salts

20.9 Reactions of Amines with Sulfonyl Chlorides

THE CHEMISTRY OF… Essential Nutrients and Antimetabolites

20.10 Synthesis of Sulfa Drugs

20.11 Analysis of Amines

20.12 Eliminations Involving Ammonium Compounds

20.13 Summary of Preparations and Reactions of Amines

[ WHY DO THESE TOPICS MATTER? ]

SPECIAL TOPIC H: Alkaloids

21 Transition Metal Complexes: PROMOTERS OF KEY BOND-FORMING REACTIONS

21.1 Organometallic Compounds in Previous Chapters

21.2 Transition Metal Elements and Complexes

21.3 HOW TO Count Electrons in a Metal Complex

21.4 Mechanistic Steps in the Reactions of Some Transition Metal Complexes

21.5 Homogeneous Hydrogenation: Wilkinson’s Catalyst

[ A MECHANISM FOR THE REACTION ] Homogeneous Hydrogenation using Wilkinson’s Catalyst

THE CHEMISTRY OF… Homogeneous Asymmetric Catalytic Hydrogenation: Examples Involving L-DOPA, (S)-N

21.6 Cross-Coupling Reactions

[ A MECHANISM FOR THE REACTION ] The Heck– Mizoroki Reaction using an Aryl Halide Substrate

THE CHEMISTRY OF… The Wacker Oxidation

THE CHEMISTRY OF… Complex Cross Couplings

21.7 Olefin Metathesis

[ A MECHANISM FOR THE REACTION ] The Olefin Metathesis Reaction

THE CHEMISTRY OF… Organic Chemistry Alchemy: Turning Simple Alkenes into “Gold”

21.8 Transition Metals in Nature: Vitamin B[sub(12)] and Vanadium Haloperoxidases

[ WHY DO THESE TOPICS MATTER? ]

SECOND REVIEW PROBLEM SET

22 Carbohydrates

22.1 Introduction

22.2 Monosaccharides

22.3 Mutarotation

22.4 Glycoside Formation

[ A MECHANISM FOR THE REACTION ] Formation of a Glycoside

[ A MECHANISM FOR THE REACTION ] Hydrolysis of a Glycoside

22.5 Other Reactions of Monosaccharides

22.6 Oxidation Reactions of Monosaccharides

22.7 Reduction of Monosaccharides: Alditols

22.8 Reactions of Monosaccharides with Phenylhydrazine: Osazones

[ A MECHANISM FOR THE REACTION ] Phenylosazone Formation

22.9 Synthesis and Degradation of Monosaccharides

22.10 The dFamily of Aldoses

22.11 Fischer’s Proof of the Configuration of d -(+)-Glucose

22.12 Disaccharides

THE CHEMISTRY OF… Artificial Sweeteners (How Sweet It Is)

22.13 Polysaccharides

22.14 Other Biologically Important Sugars

22.15 Sugars that Contain Nitrogen

22.16 Glycolipids and Glycoproteins of the Cell Surface: Cell Recognition and the Immune System

THE CHEMISTRY OF… Patroling Leukocytes and Sialyl Lewis[sup(x)] Acids

22.17 Carbohydrate Antibiotics

22.18 Summary of Reactions of Carbohydrates

[ WHY DO THESE TOPICS MATTER? ]

23 Lipids

23.1 Introduction

23.2 Fatty Acids and Triacylglycerols

THE CHEMISTRY OF… Olestra and Other Fat Substitutes

THE CHEMISTRY OF… Poison Ivy

THE CHEMISTRY OF… Self-Assembled Monolayers—Lipids in Materials Science and Bioengineering

23.3 Terpenes and Terpenoids

THE CHEMISTRY OF… The Bombardier Beetle’s Noxious Spray

23.4 Steroids

THE CHEMISTRY OF… The Enzyme Aromatase

23.5 Prostaglandins

23.6 Phospholipids and Cell Membranes

THE CHEMISTRY OF… STEALTH® Liposomes for Drug Delivery

23.7 Waxes

[ WHY DO THESE TOPICS MATTER? ]

24 Amino Acids and Proteins

24.1 Introduction

24.2 Amino Acids

24.3 Synthesis of α-Amino Acids

[ A MECHANISM FOR THE REACTION ] Formation of an α-Aminonitrile during the Strecker Synthesis

24.4 Polypeptides and Proteins

24.5 Primary Structure of Polypeptides and Proteins

24.6 Examples of Polypeptide and Protein Primary Structure

THE CHEMISTRY OF… Sickle-Cell Anemia

24.7 Polypeptide and Protein Synthesis

24.8 Secondary, Tertiary, and Quaternary Structures of Proteins

24.9 Introduction to Enzymes

24.10 Lysozyme: Mode of Action of an Enzyme

THE CHEMISTRY OF… Carbonic Anhydrase: Shuttling the Protons

24.11 Serine Proteases

24.12 Hemoglobin: A Conjugated Protein

THE CHEMISTRY OF… Some Catalytic Antibodies

24.13 Purification and Analysis of Polypeptides and Proteins

24.14 Proteomics

[ WHY DO THESE TOPICS MATTER? ]

25 Nucleic Acids and Protein Synthesis

25.1 Introduction

25.2 Nucleotides and Nucleosides

25.3 Laboratory Synthesis of Nucleosides and  Nucleotides

25.4 Deoxyribonucleic Acid: DNA

25.5 RNA and Protein Synthesis

25.6 Determining the Base Sequence of DNA: The Chain-Terminating (Dideoxynucleotide) Method

25.7 Laboratory Synthesis of Oligonucleotides

25.8 Polymerase Chain Reaction

25.9 Sequencing of the Human Genome: An Instruction Book for the Molecules of Life

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