Organic Chemistry (12th Edition)

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Download Organic Chemistry (12th Edition) written by T. W. Graham Solomon, Craig B. Fryhle, Scott A. Synder in PDF format. This book is under the category Chemistry and bearing the isbn/isbn13 number 1118875761/9781118875766. You may reffer the table below for additional details of the book.

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This Organic Chemistry 12th edition PDF eBook continues Solomons/Fryhle/Snyder’s tradition of excellence in teaching and preparing chemistry 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 reactivity and structure. 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 of the chapters. The structural aspects of the authors’ approach show college students what organic chemistry is. Mechanistic aspects of their approach show chem students how it works. And wherever an opportunity arises; the best-selling authors’ show students what it does in the physical world and in living systems around us.

Note: This product only includes a PDF. No online access codes etc are included in the purchase.

Additional information

book-author

T. W. Graham Solomon, Craig B. Fryhle, Scott A. Synder

publisher

Wiley; 12th edition

file-type

PDF

pages

1200 pages

language

English

asin

B01DV7OEFK

isbn10

1118875761

isbn13

9781118875766

Table of contents


Table of contents :
Cover
Title
Copyright
Brief Contents
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) SPECTROSCOPY
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 Broken
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 Stable Conformer
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 Reaction
[ 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 Alcohol
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 Reductions
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 Affect the Rate of an EAS Reaction
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)-Naproxen, and Aspartame
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
[ WHY DO THESE TOPICS MATTER? ]
GLOSSARY
INDEX
ANSWERS TO SELECTED PROBLEMS
EULA

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