Organic Chemistry Plus MasteringChemistry with eText -- Access Card Package

1.1 The Origins of Organic Chemistry
1.2 Principles of Atomic Structure
1.3 Bond Formation: The Octet Rule
1.4 Lewis Structures
1.5 Multiple Bonding
1.6 Electronegativity and Bond Polarity
1.7 Formal Charges
1.8 Ionic Structures
1.9 Resonance
1.10 Structural Formulas
1.11 Molecular Formulas and Empirical Formulas
1.12 Arrhenius Acids and Bases
1.13 Bronsted-Lowry Acids and Bases
1.14 Lewis Acids and Bases

2.1 Wave Properties of Electrons in Orbitals
2.2 Molecular Orbitals
2.3 Pi Bonding
2.4 Hybridization and Molecular Shapes
2.5 Drawing Three-Dimensional Molecules
2.6 General Rules of Hybridization and Geometry
2.7 Bond Rotation
2.8 Isomerism
2.9 Polarity of Bonds and Molecules
2.10 Intermolecular Forces
2.11 Polarity Effects on Solubilities
2.12 Hydrocarbons
2.13 Organic Compounds Containing Oxygen
2.14 Organic Compounds Containing Nitrogen

3.1 Classification of Hydrocarbons
3.2 Molecular Formulas of Alkanes
3.3 Nomenclature of Alkanes
3.4 Physical Properties of Alkanes
3.5 Uses and Sources of Alkanes
3.6 Reactions of Alkanes
3.7 Structure and Conformations of Alkanes
3.8 Conformations of Butane
3.9 Conformations of Higher Alkanes
3.10 Cycloalkanes
3.11 Cis-trans Isomerism in Cycloalkanes
3.12 Stabilities of Cycloalkanes; Ring Strain
3.13 Cyclohexane Conformations
3.14 Conformations of Monosubstituted Cyclohexanes
3.15 Conformations of Disubstituted Cyclohexanes
3.16 Bicyclic Molecules

4.1 Introduction
4.2 Chlorination of Methane
4.3 The Free-Radical Chain Reaction
4.4 Equilibrium Constants and Free Energy
4.5 Enthalpy and Entropy
4.6 Bond-Dissociation Enthalpies
4.7 Enthalpy Changes in Chlorination
4.8 Kinetics and the Rate Equation
4.9 Activation Energy and the Temperature Dependence of Rates
4.10 Transition States
4.11 Rates of Multistep Reactions
4.12 Temperature Dependence of Halogenation
4.13 Selectivity in Halogenation
4.14 The Hammond Postulate
4.15 Radical Inhibitors
4.16 Reactive Intermediates

5.1 Introduction
5.2 Chirality
5.3 (R) and (S) Nomenclature of Asymmetric Carbon Atoms
5.4 Optical Activity
5.5 Biological Discrimination of Enantiomers
5.6 Racemic Mixtures
5.7 Enantiomeric Excess and Optical Purity
5.8 Chirality of Conformationally Mobile Systems
5.9 Chiral Compounds without Asymmetric Atoms
5.10 Fischer Projections
5.11 Diastereomers
5.12 Stereochemistry of Molecules with Two or More Asymmetric Carbons
5.13 Meso Compounds
5.14 Absolute and Relative Configuration
5.15 Physical Properties of Diastereomers
5.16 Resolution of Enantiomers

6.1 Introduction
6.2 Nomenclature of Alkyl Halides
6.3 Common Uses of Alkyl Halides
6.4 Structure of Alkyl Halides
6.5 Physical Properties of Alkyl Halides
6.6 Preparation of Alkyl Halides
6.7 Reactions of Alkyl Halides: Substitution and Elimination
6.8 Second-Order Nucleophilic Substitution: The SN2 Reaction
6.9 Generality of the SN2 Reaction
6.10 Factors Affecting SN2 Reactions: Strength of the Nucleophile
6.11 Reactivity of the Substrate in SN2 Reactions
6.12 Stereochemistry of the SN2 Reaction
6.13 First-Order Nucleophilic Substitution: the SN1 Reaction
6.14 Stereochemistry of the SN1 Reaction
6.15 Rearrangements in SN1 Reactions
6.16 Comparison of SN1 and SN2 Reactions
6.17 First-Order Elimination: The E1 Reaction
6.18 Positional Orientation of Elimination: Zaitsev's Rule
6.19 Second-Order Elimination: The E2 Reaction
6.20 Stereochemistry of the E2 Reaction
6.21 Comparison of E1 and E2 Elimination Mechanisms

7.1 Introduction
7.2 The Orbital Description of the Alkene Double Bond
7.3 Elements of Unsaturation
7.4 Nomenclature of Alkenes
7.5 Nomenclature of Cis-Trans Isomers
7.6 Commercial Importance of Alkenes
7.7 Stability of Alkenes
7.8 Physical Properties of Alkenes
7.9 Alkene Synthesis by Elimination of Alkyl Halides
7.10 Alkene Synthesis by Dehydration of Alcohols
7.11 Alkene Synthesis by High-Temperature Industrial Methods

8.1 Reactivity of the Carbon-Carbon Double Bond
8.2 Electrophilic Addition to Alkenes
8.3 Addition of Hydrogen Halides to Alkenes
8.4 Addition of Water: Hydration of Alkenes
8.5 Hydration by Oxymercuration-Demercuration
8.6 Alkoxymercuration-Demercuration
8.7 Hydroboration of Alkenes
8.8 Addition of Halogens to Alkenes
8.9 Formation of Halohydrins
8.10 Catalytic Hydrogenation of Alkenes
8.11 Addition of Carbenes to Alkenes
8.12 Epoxidation of Alkenes
8.13 Acid-Catalyzed Opening of Epoxides
8.14 Syn Dihydroxylation of Alkenes
8.15 Oxidative Cleavage of Alkenes
8.16 Polymerization of Alkenes
8.17 Olefin Metathesis

9.1 Introduction
9.2 Nomenclature of Alkynes
9.3 Physical Properties of Alkynes
9.4 Commercial Importance of Alkynes
9.5 Electronic Structure of Alkynes
9.6 Acidity of Alkynes; Formation of Acetylide Ions
9.7 Synthesis of Alkynes from Acetylides
9.8 Synthesis of Alkynes by Elimination Reactions
9.9 Addition of Reactions of Alkynes
9.10 Oxidation of Alkynes

10.1 Introduction
10.2 Structure and Classification of Alcohols
10.3 Nomenclature of Alcohols and Phenols
10.4 Physical Properties of Alcohols
10.5 Commercially Important Alcohols
10.6 Acidity of Alcohols and Phenols
10.7 Synthesis of Alcohols: Introduction and Review
10.8 Organometallic Reagents for Alcohol Synthesis
10.9 Addition of Organometallic Reagents to Carbonyl Compounds
10.10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides
10.11 Reduction of the Carbonyl Group: Synthesis of 1º and 2º Alcohols
10.12 Thiols (Mercaptans)

11.1 Oxidation States of Alcohols and Related Functional Groups
11.2 Oxidation of Alcohols
11.3 Additional Methods for Oxidizing Alcohols
11.4 Biological Oxidation of Alcohols
11.5 Alcohols as Nucleophiles and Electrophiles; Formation of Tosylates
11.6 Reduction of Alcohols
11.7 Reactions of Alcohols with Hydrohalic Acids
11.8 Reactions of Alcohols with Phosphorus Halides
11.9 Reactions of Alcohols with Thionyl Chloride
11.10 Dehydration Reactions of Alcohols
11.11 Unique Reactions of Diols
11.12 Esterification of Alcohols
11.13 Esters of Inorganic Acids
11.14 Reactions of Alkoxides

12.1 Introduction
12.2 The Electromagnetic Spectrum
12.3 The Infrared Region
12.4 Molecular Vibrations
12.5 IR-Active and IR-Inactive Vibrations
12.6 Measurement of the IR Spectrum
12.7 Infrared Spectroscopy of Hydrocarbons
12.8 Characteristic Absorptions of Alcohols and Amines
12.9 Characteristic Absorptions of Carbonyl Compounds
12.10 Characteristic Absorptions of C-N Bonds
12.11 Simplified Summary of IR Stretching Frequencies
12.12 Reading and Interpreting IR Spectra (Solved Problems)
12.13 Introduction to Mass Spectrometry
12.14 Determination of the Molecular Formula by Mass Spectrometry
12.15 Fragmentation Patterns in Mass Spectrometry

13.1 Introduction
13.2 Theory of Nuclear Magnetic Resonance
13.3 Magnetic Shielding by Electrons
13.4 The NMR Spectrometer
13.5 The Chemical Shift
13.6 The Number of Signals
13.7 Areas of the Peaks
13.8 Spin-Spin Splitting
13.9 Complex Splitting
13.10 Stereochemical Nonequivalence of Protons
13.11 Time Dependence of NMR Spectroscopy
13.12 Carbon-13 NMR Spectroscopy
13.13 Interpreting Carbon NMR Spectra
13.14 Nuclear Magnetic Resonance Imaging

14.1 Introduction
14.2 Physical Properties of Ethers
14.3 Nomenclature of Ethers
14.4 Spectroscopy of Ethers
14.5 The Williamson Ether Synthesis
14.6 Synthesis of Ethers by Alkoxymercuration-Demercuration
14.7 Industrial Synthesis: Bimolecular Condensation of Alcohols
14.8 Cleavage of Ethers by HBr and HI
14.9 Autoxidation of Ethers
14.10 Thioethers (Sulfides) and Silyl Ethers
14.11 Synthesis of Epoxides
14.12 Acid-Catalyzed Ring Opening of Epoxides
14.13 Base-Catalyzed Ring Opening of Epoxides
14.14 Orientation of Epoxide Ring Opening
14.15 Reactions of Epoxides with Grignard and Organolithium Reagents
14.16 Epoxy Resins: The Advent of Modern Glues

15.1 Introduction
15.2 Stabilities of Dienes
15.3 Molecular Orbital Picture of a Conjugated System
15.4 Allylic Cations
15.5 1,2 and 1,4 Addition to Conjugated Dienes
15.6 Kinetic versus Thermodynamic Control in the Addition of HBr
15.7 Allylic Radicals
15.8 Molecular Orbitals of the Allylic System
15.9 Electronic Configurations of the Allyl Radical, Cation and Anion
15.10 SN2 Displacement Reactions of Allylic Halides and Tosylates
15.11 The Diels-Alder Reaction
15.12 The Diels-Alder as an Example of a Pericyclic Reaction
15.13 Ultraviolet Absorption Spectroscopy

16.1 Introduction: The Discovery of Benzene
16.2 The Structure and Properties of Benzene
16.3 The Molecular Orbitals of Benzene
16.4 The Molecular Orbital Picture of Cyclobutadiene
16.5 Aromatic, Antiaromatic, and Nonaromatic Compounds
16.6 Huckel's Rule
16.7 Molecular Orbital Derivation of Huckel's Rule
16.8 Aromatic Ions
16.9 Heterocyclic Aromatic Compounds
16.10 Polynuclear Aromatic Hydrocarbons
16.11 Aromatic Allotropes of Carbon
16.12 Fused Heterocyclic Compounds
16.13 Nomenclature of Benzene Derivatives
16.14 Physical Properties of Benzene and Its Derivatives
16.15 Spectroscopy of Aromatic Compounds

17.1 Electrophilic Aromatic Substitution
17.2 Halogenation of Benzene
17.3 Nitration of Benzene
17.4 Sulfonation of Benzene
17.5 Nitration of Toluene: The Effect of Alkyl Substitution
17.6 Activating, Ortho, Para-Directing Substituents
17.7 Deactivating, Meta-Directing Substituents
17.8 Halogen Substituents: Deactivating, but Ortho, Para-Directing
17.9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution
17.10 The Friedel-Crafts Alkylation
17.11 The Friedel-Crafts Acylation
17.12 Nucleophilic Aromatic Substitution
17.13 Aromatic Substitutions Using Organometallic Reagents (new section)
17.14 Addition Reactions of Benzene Derivatives
17.15 Side-Chain Reactions of Benzene Derivatives
17.16 Reactions of Phenols

18.1 Carbonyl Compounds
18.2 Structure of the Carbonyl Group
18.3 Nomenclature of Ketones and Aldehydes
18.4 Physical Properties of Ketones and Aldehydes
18.5 Spectroscopy of Ketones and Aldehydes
18.6 Industrial Importance of Ketones and Aldehydes
18.7 Review of Syntheses of Ketones and Aldehydes
18.8 Synthesis of Ketones from Carboxylic Acids 18.9 Synthesis of Ketones and Aldehydes from Nitriles
18.10 Synthesis of Aldehydes and Ketones from Acid Chlorides and Esters
18.11 Reactions of Ketones and Aldehydes: Nucleophilic Addition
18.12 The Wittig Reaction
18.13 Hydration of Ketones and Aldehydes
18.14 Formation of Cyanohydrins
18.15 Formation of Imines
18.16 Condensations with Hydroxylamine and Hydrazines
18.17 Formation of Acetals
18.18 Use of Acetals as Protecting Groups
18.19 Oxidation of Aldehydes
18.20 Reductions of Ketones and Aldehydes

19.1 Introduction
19.2 Nomenclature of Amines
19.3 Structure of Amines
19.4 Physical Properties of Amines
19.5 Basicity of Amines
19.6 Effects on Amine Basicity
19.7 Salts of Amines
19.8 Spectroscopy of Amines
19.9 Reactions of Amines with Ketones and Aldehydes (Review)
19.10 Aromatic Substitution of Arylamines and Pyridine
19.11 Alkylation of Amines by Alkyl Halides
19.12 Acylation of Amines by Acid Chlorides
19.13 Formation of Sulfonamides
19.14 Amines as Leaving Groups: The Hofmann Elimination
19.15 Oxidation of Amines; The Cope Elimination
19.16 Reactions of Amines with Nitrous Acid
19.17 Reactions of Arenediazonium Salts
19.18 Synthesis of Amines by Reductive Amination
19.19 Synthesis of Amines by Acylation-Reduction
19.20 Syntheses Limited to Primary Amines

20.1 Introduction
20.2 Nomenclature of Carboxylic Acids
20.3 Structure and Physical Properties of Carboxylic Acids
20.4 Acidity of Carboxylic Acids
20.5 Salts of Carboxylic Acids
20.6 Commercial Sources of Carboxylic Acids
20.7 Spectroscopy of Carboxylic Acids
20.8 Synthesis of Carboxylic Acids
20.9 Reactions of Carboxylic Acids and Derivatives; Nucleophilic Acyl Substitution
20.10 Condensation of Acids with Alcohols: The Fischer Esterification
20.11 Esterification Using Diazomethane
20.12 Condensation of Acids with Amines: Direct Synthesis of Amides
20.13 Reduction of Carboxylic Acids
20.14 Alkylation of Carboxylic Acids to Form Ketones
20.15 Synthesis and Use of Acid Chlorides

21.1 Introduction
21.2 Structure and Nomenclature of Acid Derivatives
21.3 Physical Properties of Carboxylic Acid Derivatives
21.4 Spectroscopy of Carboxylic Acid Derivatives
21.5 Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution
21.6 Transesterification
21.7 Hydrolysis of Carboxylic Acid Derivatives
21.8 Reduction of Acid Derivatives
21.9 Reactions of Acid Derivatives with Organometallic Reagents
21.10 Summary of the Chemistry of Acid Chlorides
21.11 Summary of the Chemistry of Anhydrides
21.12 Summary of the Chemistry of Esters
21.13 Summary of the Chemistry of Amides
21.14 Summary of the Chemistry of Nitriles
21.15 Thioesters
21.16 Esters and Amides of Carbonic Acid

22.1 Introduction
22.2 Enols and Enolate Ions
22.3 Alkylation of Enolate Ions
22.4 Formation and Alkylation of Enamines
22.5 Alpha Halogenation of Ketones
22.6 Bromination of Acids: The HVZ Reaction
22.7 The Aldol Condensation of Ketones and Aldehydes
22.8 Dehydration of Aldol Products
22.9 Crossed Aldol Condensations
22.10 Aldol Cyclizations
22.11 Planning Syntheses Using Aldol Condensations
22.12 The Claisen Ester Condensation
22.13 The Dieckmann Condensation: A Claisen Cyclization
22.14 Crossed Claisen Condensations
22.15 Syntheses Using β-Dicarbonyl Compounds
22.16 The Malonic Ester Synthesis
22.17 The Acetoacetic Ester Synthesis
22.18 Conjugate Additions: The Michael Reaction
22.19 The Robinson Annulation

23.1 Introduction
23.2 Classification of Carbohydrates
23.3 Monosaccharides
23.4 Erythro and Threo Diastereomers
23.5 Epimers
23.6 Cyclic Structures of Monosaccharides
23.7 Anomers of Monosaccharides; Mutarotation
23.8 Reactions of Monosaccharides: Side Reactions in Base
23.9 Reduction of Monosaccharides
23.10 Oxidation of Monosaccharides; Reducing Sugars
23.11 Nonreducing Sugars: Formation of Glycosides
23.12 Ether and Ester Formation
23.13 Reactions with Phenylhydrazine: Osazone Formation
23.14 Chain Shortening: The Ruff Degradation
23.15 Chain Lengthening: The Kiliani-Fischer Synthesis
23.16 Determination of Ring Size; Periodic Acid Cleavage of Sugars
23.17 Disaccharides
23.18 Polysaccharides
23.19 Nucleic Acids: Introduction
23.20 Ribonucleosides and Ribonucleotides
23.21 The Structure of RNA and DNA
23.22 Additional Functions of Nucleotides

24.1 Introduction
24.2 Structure and Stereochemistry of the Amino Acids
24.3 Acid-Base Properties of Amino Acids
24.4 Isoelectric Points and Electrophoresis
24.5 Synthesis of Amino Acids
24.6 Resolution of Amino Acids
24.7 Reactions of Amino Acids
24.8 Structure and Nomenclature of Peptides and Proteins
24.9 Peptide Structure Determination
24.10 Solution-Phase Peptide Synthesis
24.11 Solid-Phase Peptide Synthesis
24.12 Classification of Proteins
24.13 Levels of Protein Structure
24.14 Protein Denaturation

25.1 Introduction
25.2 Waxes
25.3 Trigylcerides
25.4 Saponification of Fats and Oils; Soaps and Detergents
25.5 Phospholipids
25.6 Steroids
25.7 Prostaglandins
25.8 Terpenes

26.1 Introduction
26.2 Addition Polymers
26.3 Stereochemistry of Polymers
26.4 Stereochemical Control of Polymerization; Ziegler-Natta Catalysts
26.5 Natural and Synthetic Rubbers
26.6 Copolymers of Two or More Monomers
26.7 Condensation Polymers
26.8 Polymer Structure and Properties

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