Organic Chemistry 12th Edition by Francis A Carey Dr, Robert M Giuliano, Neil T Allison, Susan L Bane ISBN 9781266159244 126615924X
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ISBN 10: 126615924X
ISBN 13: 9781266159244
Author: Francis A Carey Dr, Robert M Giuliano, Neil T Allison, Susan L Bane
Organic Chemistry 12th Edition Table of contents:
Chapter 1: Structure Determines Properties
Chapter 1 Introduction
1.1 Atoms, Electrons, and Orbitals
1.2 Ionic Bonds
1.3 Covalent Bonds, Lewis Formulas, and the Octet Rule
1.4 Polar Covalent Bonds, Electronegativity, and Bond Dipoles
1.5 Formal Charge
1.6 Structural Formulas of Organic Molecules: Isomers
1.7 Resonance and Arrows
1.8 Sulfur and Phosphorus-Containing Organic Compounds and the Octet Rule
1.9 Molecular Geometries
1.10 Molecular Dipole Moments
1.11 Curved Arrows, Arrow Pushing, and Chemical Reactions
1.12 Acids and Bases: The Brønsted–Lowry View
1.13 How Structure Affects Acid Strength
1.14 Acid–Base Equilibria
1.15 Acids and Bases: The Lewis View
1.16 Summary
Problems
Structural Formulas
Formal Charge and Resonance
Dipole Moment
Acids and Bases
Descriptive Passage and Interpretive Problems 1
Amide Lewis Structural Formulas
Chapter 2: Alkanes and Cycloalkanes: Introduction to Hydrocarbons
Chapter 2 Introduction
2.1 Classes of Hydrocarbons
2.2 Electron Waves and Chemical Bonds
2.3 Bonding in H2: The Valence Bond Model
2.4 Bonding in H2: The Molecular Orbital Model
2.5 Introduction to Alkanes: Methane, Ethane, and Propane
2.6 sp3 Hybridization and Bonding in Methane
2.7 Bonding in Ethane
2.8 sp2 Hybridization and Bonding in Ethylene
2.9 sp Hybridization and Bonding in Acetylene
2.10 Bonding in Water and Ammonia: Hybridization of Oxygen and Nitrogen
2.11 Molecular Orbitals and Bonding in Methane
2.12 Isomeric Alkanes: The Butanes
2.13 Higher n-Alkanes
2.14 The C5H12 Isomers
2.15 IUPAC Nomenclature of Unbranched Alkanes
2.16 Applying the IUPAC Rules: The Names of the C6H14 Isomers
2.17 Alkyl Groups
2.18 IUPAC Names of Highly Branched Alkanes
2.19 Cycloalkane Nomenclature
2.20 Introduction to Functional Groups
2.21 Sources of Alkanes and Cycloalkanes
2.22 Physical Properties of Alkanes and Cycloalkanes
2.23 Chemical Properties: Combustion of Alkanes
2.24 Oxidation–Reduction in Organic Chemistry
2.25 Summary
Problems
Structure and Bonding
Nomenclature
Reactions
Descriptive Passage and Interpretive Problems 2
Some Biochemical Reactions of Alkanes
Chapter 3: Alkanes and Cycloalkanes: Conformations and cis–trans Stereoisomers
Chapter 3 Introduction
3.1 Conformational Analysis of Ethane
3.2 Conformational Analysis of Butane
3.3 Conformations of Higher Alkanes
3.4 The Shapes of Cycloalkanes: Planar or Nonplanar?
3.5 Small Rings: Cyclopropane and Cyclobutane
3.6 Cyclopentane
3.7 Conformations of Cyclohexane
3.8 Axial and Equatorial Bonds in Cyclohexane
3.9 Conformational Inversion in Cyclohexane
3.10 Conformational Analysis of Monosubstituted Cyclohexanes
3.11 Disubstituted Cycloalkanes: cis–trans Stereoisomers
3.12 Conformational Analysis of Disubstituted Cyclohexanes
3.13 Medium and Large Rings
3.14 Polycyclic Ring Systems
3.15 Heterocyclic Compounds
3.16 Summary
Problems
Nomenclature and Terminology
Constitutional Isomers, Stereoisomers, and Conformers
Conformations: Relative Stability
Stereoisomers: Relative Stability
Properties
Descriptive Passage and Interpretive Problems 3
Cyclic Forms of Carbohydrates
Chapter 4: Chirality
Chapter 4 Introduction
4.1 Introduction to Chirality: Enantiomers
4.2 The Chirality Center
4.3 Symmetry in Achiral Structures
4.4 Optical Activity
4.5 Absolute and Relative Configuration
4.6 Cahn–Ingold–Prelog R,S Notation
4.7 Fischer Projections
4.8 Properties of Enantiomers
4.9 Chiral Molecules with Two Chirality Centers
4.10 Achiral Molecules with Two Chirality Centers
4.11 Molecules with Multiple Chirality Centers
4.12 Resolution of Enantiomers
4.13 The Chirality Axis
4.14 Chirality Centers Other Than Carbon
4.15 Summary
Problems
Molecular Chirality
R,S-Configurational Notation
Structural Relationships
Optical Activity
Descriptive Passage and Interpretive Problems 4
Prochirality
Chapter 5: Alcohols and Alkyl Halides: Introduction to Reaction Mechanisms
Chapter 5 Introduction
5.1 Functional Groups
5.2 IUPAC Nomenclature of Alkyl Halides
5.3 IUPAC Nomenclature of Alcohols
5.4 Classes of Alcohols and Alkyl Halides
5.5 Bonding in Alcohols and Alkyl Halides
5.6 Physical Properties of Alcohols and Alkyl Halides: Intermolecular Forces
5.7 Preparation of Alkyl Halides from Alcohols and Hydrogen Halides
5.8 Reaction of Alcohols with Hydrogen Halides: The SN1 Mechanism
5.9 Structure, Bonding, and Stability of Carbocations
5.10 Effect of Alcohol Structure on Reaction Rate
5.11 Stereochemistry and the SN1 Mechanism
5.12 Carbocation Rearrangements
5.13 Reaction of Methyl and Primary Alcohols with Hydrogen Halides: The SN2 Mechanism
5.14 Other Methods for Converting Alcohols to Alkyl Halides
5.15 Sulfonates as Alkyl Halide Surrogates
5.16 Summary
Problems
Structure and Nomenclature
Functional Groups
Reactions and Mechanisms
Descriptive Passage and Interpretive Problems 5
More About Potential Energy Diagrams
Chapter 6: Nucleophilic Substitution
Chapter 6 Introduction
6.1 Functional-Group Transformation by Nucleophilic Substitution
6.2 Relative Reactivity of Halide Leaving Groups
6.3 The SN2 Mechanism of Nucleophilic Substitution
6.4 Steric Effects and SN2 Reaction Rates
6.5 Nucleophiles and Nucleophilicity
6.6 The SN1 Mechanism of Nucleophilic Substitution
6.7 Stereochemistry of SN1 Reactions
6.8 Carbocation Rearrangements in SN1 Reactions
6.9 Effect of Solvent on the Rate of Nucleophilic Substitution
6.10 Nucleophilic Substitution of Alkyl Sulfonates
6.11 Introduction to Organic Synthesis: Retrosynthetic Analysis
6.12 Substitution versus Elimination: A Look Ahead
6.13 Summary
Problems
Predict the Products
Rate and Mechanism
Stereochemistry
Synthesis
Descriptive Passage and Interpretive Problems 6
Nucleophilic Substitution
Chapter 7: Structure and Preparation of Alkenes: Elimination Reactions
Chapter 7 Introduction
7.1 Alkene Nomenclature
7.2 Structure and Bonding in Alkenes
7.3 Isomerism in Alkenes
7.4 Naming Stereoisomeric Alkenes by the E–Z Notational System
7.5 Physical Properties of Alkenes
7.6 Relative Stabilities of Alkenes
7.7 Cycloalkenes
7.8 Preparation of Alkenes: Elimination Reactions
7.9 Dehydration of Alcohols
7.10 Regioselectivity in Alcohol Dehydration: The Zaitsev Rule
7.11 Stereoselectivity in Alcohol Dehydration
7.12 The E1 and E2 Mechanisms of Alcohol Dehydration
7.13 Rearrangements in Alcohol Dehydration
7.14 Dehydrohalogenation of Alkyl Halides
7.15 The E2 Mechanism of Dehydrohalogenation of Alkyl Halides
7.16 Anti Elimination in E2 Reactions: Stereoelectronic Effects
7.17 Isotope Effects and the E2 Mechanism
7.18 The E1 Mechanism of Dehydrohalogenation of Alkyl Halides
7.19 Substitution and Elimination as Competing Reactions
7.20 Elimination Reactions of Sulfonates
7.21 Summary
Problems
Structure and Nomenclature
Reactions
Mechanisms
Descriptive Passage and Interpretive Problems 7
A Mechanistic Preview of Addition Reactions
Chapter 8: Addition Reactions of Alkenes
Chapter 8 Introduction
8.1 Hydrogenation of Alkenes
8.2 Stereochemistry of Alkene Hydrogenation
8.3 Heats of Hydrogenation
8.4 Electrophilic Addition of Hydrogen Halides to Alkenes
8.5 Carbocation Rearrangements in Hydrogen Halide Addition to Alkenes
8.6 Acid-Catalyzed Hydration of Alkenes
8.7 Thermodynamics of Addition–Elimination Equilibria
8.8 Hydroboration–Oxidation of Alkenes
8.9 Mechanism of Hydroboration–Oxidation
8.10 Addition of Halogens to Alkenes
8.11 Epoxidation of Alkenes
8.12 Ozonolysis of Alkenes
8.13 Enantioselective Addition to Alkenes
8.14 Retrosynthetic Analysis and Alkene Intermediates
8.15 Summary
Problems
Reactions of Alkenes
Stereochemistry
Thermochemistry
Synthesis
Structure Determination
Mechanism
Descriptive Passage and Interpretive Problems 8
Oxymercuration
Chapter 9: Alkynes
Chapter 9 Introduction
9.1 Sources of Alkynes
9.2 Nomenclature
9.3 Physical Properties of Alkynes
9.4 Structure and Bonding in Alkynes: sp Hybridization
9.5 Acidity of Acetylene and Terminal Alkynes
9.6 Preparation of Alkynes by Alkylation of Acetylene and Terminal Alkynes
9.7 Preparation of Alkynes by Elimination Reactions
9.8 Reactions of Alkynes
9.9 Hydrogenation of Alkynes
9.10 Addition of Hydrogen Halides to Alkynes
9.11 Hydration of Alkynes
9.12 Addition of Halogens to Alkynes
9.13 Ozonolysis of Alkynes
9.14 Alkynes in Synthesis and Retrosynthesis
9.15 Summary
Problems
Structure and Nomenclature
Reactions
Synthesis
Mechanism
Descriptive Passage and Interpretive Problems 9
Thinking Mechanistically About Alkynes
Chapter 10: Introduction to Free Radicals
Chapter 10 Introduction
10.1 Structure, Bonding, and Stability of Alkyl Radicals
10.2 Halogenation of Alkanes
10.3 Mechanism of Methane Chlorination
10.4 Halogenation of Higher Alkanes
10.5 Free-Radical Addition of Hydrogen Bromide to Alkenes and Alkynes
10.6 Metal–Ammonia Reduction of Alkynes
10.7 Free Radicals and Retrosynthesis of Alkyl Halides
10.8 Free-Radical Polymerization of Alkenes
10.9 Summary
Problems
Structure and Bonding
Reactions
Synthesis
Mechanism
Descriptive Passage and Interpretive Problems 10
Free-Radical Reduction of Alkyl Halides
Chapter 11: Conjugation in Alkadienes and Allylic Systems
Chapter 11 Introduction
11.1 The Allyl Group
11.2 SN1 and SN2 Reactions of Allylic Halides
11.3 Allylic Free-Radical Halogenation
11.4 Allylic Anions
11.5 Classes of Dienes: Conjugated and Otherwise
11.6 Relative Stabilities of Dienes
11.7 Bonding in Conjugated Dienes
11.8 Bonding in Allenes
11.9 Preparation of Dienes
11.10 Addition of Hydrogen Halides to Conjugated Dienes
11.11 Halogen Addition to Dienes
11.12 The Diels–Alder Reaction
11.13 Intramolecular Diels–Alder Reactions
11.14 Retrosynthetic Analysis and the Diels–Alder Reaction
11.15 Molecular Orbital Analysis of the Diels–Alder Reaction
11.16 The Cope and Claisen Rearrangements
11.17 Summary
Problems
Structure and Nomenclature
Reactions
Synthesis
Mechanism
Descriptive Passage and Interpretive Problems 11
1,3-Dipolar Cycloaddition
Chapter 12: Arenes and Aromaticity
Chapter 12 Introduction
12.1 Benzene
12.2 The Structure of Benzene
12.3 The Stability of Benzene
12.4 Bonding in Benzene
12.5 Substituted Derivatives of Benzene and Their Nomenclature
12.6 Polycyclic Aromatic Hydrocarbons
12.7 Physical Properties of Arenes
12.8 The Benzyl Group
12.9 Nucleophilic Substitution in Benzylic Halides
12.10 Benzylic Free-Radical Halogenation
12.11 Benzylic Anions
12.12 Oxidation of Alkylbenzenes
12.13 Alkenylbenzenes
12.14 Polymerization of Styrene
12.15 The Birch Reduction
12.16 Benzylic Side Chains and Retrosynthetic Analysis
12.17 Cyclobutadiene and Cyclooctatetraene
12.18 Hückel’s Rule
12.19 Annulenes
12.20 Aromatic Ions
12.21 Heterocyclic Aromatic Compounds
12.22 Heterocyclic Aromatic Compounds and Hückel’s Rule
12.23 Summary
Problems
Structure and Nomenclature
Resonance, Aromaticity, and Mechanism
Reactions and Synthesis
Descriptive Passage and Interpretive Problems 12
Substituent Effects on Reaction Rates and Equilibria
Chapter 13: Electrophilic and Nucleophilic Aromatic Substitution
Chapter 13 Introduction
13.1 Representative Electrophilic Aromatic Substitution Reactions of Benzene
13.2 Mechanistic Principles of Electrophilic Aromatic Substitution
13.3 Nitration of Benzene
13.4 Sulfonation of Benzene
13.5 Halogenation of Benzene
13.6 Friedel–Crafts Alkylation of Benzene
13.7 Friedel–Crafts Acylation of Benzene
13.8 Synthesis of Alkylbenzenes by Acylation–Reduction
13.9 Rate and Regioselectivity in Electrophilic Aromatic Substitution
13.10 Rate and Regioselectivity in the Nitration of Toluene
13.11 Rate and Regioselectivity in the Nitration of (Trifluoromethyl)benzene
13.12 Substituent Effects in Electrophilic Aromatic Substitution: Activating Substituents
13.13 Substituent Effects in Electrophilic Aromatic Substitution: Strongly Deactivating Substituents
13.14 Substituent Effects in Electrophilic Aromatic Substitution: Halogens
13.15 Multiple Substituent Effects
13.16 Retrosynthetic Analysis and the Synthesis of Substituted Benzenes
13.17 Substitution in Naphthalene
13.18 Substitution in Heterocyclic Aromatic Compounds
13.19 Nucleophilic Aromatic Substitution
13.20 The Addition–Elimination Mechanism of Nucleophilic Aromatic Substitution
13.21 Related Nucleophilic Aromatic Substitutions
13.22 Summary
Problems
Predict the Product
Reactivity
Synthesis
Mechanism
Descriptive Passage and Interpretive Problems 13
Benzyne
Chapter 14: Spectroscopy
Chapter 14 Introduction
14.1 Principles of Molecular Spectroscopy: Electromagnetic Radiation
14.2 Principles of Molecular Spectroscopy: Quantized Energy States
14.3 Introduction to 1H NMR Spectroscopy
14.4 Nuclear Shielding and 1H Chemical Shifts
14.5 Effects of Molecular Structure on 1H Chemical Shifts
14.6 Interpreting 1H NMR Spectra
14.7 Spin–Spin Splitting and 1H NMR
14.8 Splitting Patterns: The Ethyl Group
14.9 Splitting Patterns: The Isopropyl Group
14.10 Splitting Patterns: Pairs of Doublets
14.11 Complex Splitting Patterns
14.12 1H NMR Spectra of Alcohols
14.13 NMR and Conformations
14.14 13C NMR Spectroscopy
14.15 13C Chemical Shifts
14.16 13C NMR and Peak Intensities
14.17 13C−1H Coupling
14.18 Using DEPT to Count Hydrogens
14.19 2D NMR: COSY and HETCOR
14.20 Introduction to Infrared Spectroscopy
14.21 Infrared Spectra
14.22 Characteristic Absorption Frequencies
14.23 Ultraviolet-Visible Spectroscopy
14.24 Mass Spectrometry
14.25 Molecular Formula as a Clue to Structure
14.26 Summary
1 H Nuclear Magnetic Resonance Spectroscopy
13 C Nuclear Magnetic Resonance Spectroscopy
Infrared Spectroscopy
Ultraviolet-Visible Spectroscopy
Mass Spectrometry
Problems
1 H NMR Spectroscopy
13 C NMR Spectroscopy
19 F and 31 P NMR Spectroscopy
Combined Spectra
Descriptive Passage and Interpretive Problems 14
More on Coupling Constants
Chapter 15: Organometallic Compounds
Chapter 15 Introduction
15.1 Organometallic Nomenclature
15.2 Carbon–Metal Bonds
15.3 Preparation of Organolithium and Organomagnesium Compounds
15.4 Organolithium and Organomagnesium Compounds as Brønsted Bases
15.5 Synthesis of Alcohols Using Grignard and Organolithium Reagents
15.6 Synthesis of Acetylenic Alcohols
15.7 Retrosynthetic Analysis and Grignard and Organolithium Reagents
15.8 An Organozinc Reagent for Cyclopropane Synthesis
15.9 Carbenes and Carbenoids
15.10 Transition-Metal Organometallic Compounds
15.11 Organocopper Reagents
15.12 Palladium-Catalyzed Cross-Coupling
15.13 Homogeneous Catalytic Hydrogenation
15.14 Olefin Metathesis
15.15 Ziegler–Natta Catalysis of Alkene Polymerization
15.16 Summary
Problems
Preparation and Reactions of Main-Group Organometallic Compounds
Reactions of Transition-Metal Organometallic Compounds
Synthetic Applications of Organometallic Compounds
Transition-Metal-Catalyzed Reactions
Descriptive Passage and Interpretive Problems 15
Allylindium Reagents
Chapter 16: Alcohols, Diols, and Thiols
Chapter 16 Introduction
16.1 Sources of Alcohols
16.2 Preparation of Alcohols by Reduction of Aldehydes and Ketones
16.3 Preparation of Alcohols by Reduction of Carboxylic Acids
16.4 Preparation of Alcohols from Epoxides
16.5 Preparation of Diols
16.6 Reactions of Alcohols: A Review and a Preview
16.7 Conversion of Alcohols to Ethers
16.8 Esterification
16.9 Oxidation of Alcohols
16.10 Biological Oxidation of Alcohols
16.11 Oxidative Cleavage of Vicinal Diols
16.12 Thiols
16.13 Spectroscopic Analysis of Alcohols and Thiols
16.14 Summary
Problems
Preparation of Alcohols, Diols, and Thiols
Reactions
Synthesis
Structure Determination
Descriptive Passage and Interpretive Problems 16
The Pinacol Rearrangement
Chapter 17: Ethers, Epoxides, and Sulfides
Chapter 17 Introduction
17.1 Nomenclature of Ethers, Epoxides, and Sulfides
17.2 Structure and Bonding in Ethers and Epoxides
17.3 Physical Properties of Ethers
17.4 Crown Ethers
17.5 Preparation of Ethers
17.6 The Williamson Ether Synthesis
17.7 Reactions of Ethers: A Review and a Preview
17.8 Acid-Catalyzed Cleavage of Ethers
17.9 Preparation of Epoxides
17.10 Conversion of Vicinal Halohydrins to Epoxides
17.11 Reactions of Epoxides with Anionic Nucleophiles
17.12 Acid-Catalyzed Ring Opening of Epoxides
17.13 Epoxides in Biological Processes
17.14 Preparation of Sulfides
17.15 Oxidation of Sulfides: Sulfoxides and Sulfones
17.16 Alkylation of Sulfides: Sulfonium Salts
17.17 Spectroscopic Analysis of Ethers, Epoxides, and Sulfides
17.18 Summary
Problems
Structure and Nomenclature
Reactions and Synthesis
Mechanisms
Spectroscopy and Structure Determination
Descriptive Passage and Interpretive Problems 17
Epoxide Rearrangements and the NIH Shift
Chapter 18: Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group
Chapter 18 Introduction
18.1 Nomenclature
18.2 Structure and Bonding: The Carbonyl Group
18.3 Physical Properties
18.4 Sources of Aldehydes and Ketones
18.5 Reactions of Aldehydes and Ketones: A Review and a Preview
18.6 Principles of Nucleophilic Addition: Hydration of Aldehydes and Ketones
18.7 Cyanohydrin Formation
18.8 Reaction with Alcohols: Acetals and Ketals
18.9 Acetals and Ketals as Protecting Groups
18.10 Reaction with Primary Amines: Imines
18.11 Reaction with Secondary Amines: Enamines
18.12 The Wittig Reaction
18.13 Stereoselective Addition to Carbonyl Groups
18.14 Oxidation of Aldehydes
18.15 Spectroscopic Analysis of Aldehydes and Ketones
18.16 Summary
Problems
Structure and Nomenclature
Reactions
Synthesis
Mechanism
Spectroscopy
Descriptive Passage and Interpretive Problems 18
The Baeyer–Villiger Oxidation
Chapter 19: Carboxylic Acids
Chapter 19 Introduction
19.1 Carboxylic Acid Nomenclature
19.2 Structure and Bonding
19.3 Physical Properties
19.4 Acidity of Carboxylic Acids
19.5 Substituents and Acid Strength
19.6 Ionization of Substituted Benzoic Acids
19.7 Salts of Carboxylic Acids
19.8 Dicarboxylic Acids
19.9 Carbonic Acid
19.10 Sources of Carboxylic Acids
19.11 Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents
19.12 Synthesis of Carboxylic Acids by the Preparation and Hydrolysis of Nitriles
19.13 Reactions of Carboxylic Acids: A Review and a Preview
19.14 Mechanism of Acid-Catalyzed Esterification
19.15 Intramolecular Ester Formation: Lactones
19.16 Decarboxylation of Malonic Acid and Related Compounds
19.17 Spectroscopic Analysis of Carboxylic Acids
19.18 Summary
Problems
Structure and Nomenclature
Synthesis
Reactions
Spectroscopy
Descriptive Passage and Interpretive Problems 19
Lactonization Methods
Chapter 20: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution
Chapter 20 Introduction
20.1 Nomenclature of Carboxylic Acid Derivatives
20.2 Structure and Reactivity of Carboxylic Acid Derivatives
20.3 Nucleophilic Acyl Substitution Mechanisms
20.4 Nucleophilic Acyl Substitution in Acyl Chlorides
20.5 Nucleophilic Acyl Substitution in Acid Anhydrides
20.6 Physical Properties and Sources of Esters
20.7 Reactions of Esters: A Preview
20.8 Acid-Catalyzed Ester Hydrolysis
20.9 Ester Hydrolysis in Base: Saponification
20.10 Reaction of Esters with Ammonia and Amines
20.11 Reaction of Esters with Grignard and Organolithium Reagents and Lithium Aluminum Hydride
20.12 Amides
20.13 Hydrolysis of Amides
20.14 Lactams
20.15 Preparation of Nitriles
20.16 Hydrolysis of Nitriles
20.17 Addition of Grignard Reagents to Nitriles
20.18 Spectroscopic Analysis of Carboxylic Acid Derivatives
20.19 Summary
Problems
Structure and Nomenclature
Reactions
Synthesis
Kinetics and Mechanism
Spectroscopy
Descriptive Passage and Interpretive Problems 20
Thioesters
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