Organic Chemistry, Global Edition

Name: Organic Chemistry, Global Edition
Price: 4490 ISK
Availability: InStock
Author: Paula Yurkanis Bruice
ISBN: 9781292471389

Höfundur: Paula Yurkanis Bruice (Útgáfa: 9)

Kaup valmöguleikar

Organic Chemistry, Global Edition provides the conceptual foundations, chemical logic and problem-solving skills needed to reason your way to solutions for problems in synthetic organic chemistry, biochemistry and medicine. By building an organic chemistry framework, you can understand and apply learning rather than relying on memorization. The 9th Edition presents a wealth of problem-solving strategies, over 300 new problems (now totaling over 2,000), updated content and organizational changes to support the unique ways you acquire knowledge, study, practice and master organic chemistry.

Nánar um bókina

Útgefandi: Pearson International Content

ISBN: 9781292471389

Print ISBN: 9781292471419

Format: ePub

Útgáfa: 9

Höfundar: Paula Yurkanis Bruice

Tungumál: English

Útgefið: 2025-03-24

Prent takmörkun á líftíma: 100

Prent takmörkun: 2

Afritunar takmörkun: 2

Kaflar

Cover
Cover
Front Matter
Title Page
Copyright Page
Dedication
To the Student
Preface
Acknowledgments
About the Author
Contents
Contents
Brief Contents
PART ONE: An Introduction to the Study of Organic Chemistry
PART ONE: An Introduction to the Study of Organic Chemistry
1: Remembering General Chemistry: Electronic Structure and Bonding
Introduction: Remembering General Chemistry: Electronic Structure and Bonding
1.1: The Structure of an Atom
1.2: How the Electrons in an Atom are Distributed
1.3: Why and How Atoms Form Bonds
1.4: How the Structure of a Compound is Represented
1.5: Atomic Orbitals
1.6: An Introduction to Molecular Orbital Theory
1.7: How Single Bonds are Formed: The Bonds in Methane and Ethane
1.8: How a Double Bond is Formed: The Bonds in Ethene
1.9: How a Triple Bond is Formed: The Bonds in Ethyne
1.10: The Methyl Cation and the Methyl Anion
1.11: The Bonds in Ammonia and in the Ammonium Ion
1.12: The Bonds in Water
1.13: The Bond in a Hydrogen Halide
1.14: Hybridization and Molecular Geometry
1.15: Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles
1.16: Dipole Moments of Molecules
Chapter 1: Essential Concepts
Chapter 1: Problems
Tutorial: Drawing Structures of Organic Compounds
Tutorial: Drawing Structures of Organic Compounds
2: Acids and Bases: Central to Understanding Organic Chemistry
Introduction: Acids and Bases: Central to Understanding Organic Chemistry
2.1: What Are Acids and Bases
2.2: pKa and pH
2.3: Organic Acids and Bases
2.4: How to Predict the Outcome of an Acid-Base Reaction
2.5: How to Determine the Position of Equilibrium
2.6: How the Structure of an Acid Affects its pKa Value
2.7: How Substituents Affect the Strength of an Acid
2.8: An Introduction to Delocalized Electrons
2.9: A Summary of the Factors that Determine Acid Strength
2.10: How pH Affects the Structure of an Organic Compound
2.11: Buffer Solutions
2.12: Lewis Acids and Bases
Chapter 2: Essential Concepts
Chapter 2: Problems
Tutorial: Acids and Bases
Tutorial: Acids and Bases
3: An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Rotation About Single Bonds
Introduction: An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Rotation About Single Bonds
3.1: An Introduction to Nomenclature
3.2: Naming Alkyl Groups
3.3: Naming Alkanes
3.4: Naming Cycloalkanes
3.5: Naming Alkyl Halides
3.6: Naming Ethers
3.7: Naming Alcohols
3.8: Naming Amines
3.9: The Structures of Alkyl Halides, Alcohols, Ethers, and Amines
3.10: Noncovalent Interactions
3.11: The Solubility of Organic Compounds
3.12: Rotation Occurs about Carbon–Carbon Single Bonds
3.13: Some Cycloalkanes Have Angle Strain
3.14: Conformers of Cyclohexane
3.15: Conformers of Monosubstituted Cyclohexanes
3.16: Conformers of Disubstituted Cyclohexanes
3.17: Fused Cyclohexane Rings
Chapter 3: Essential Concepts
Chapter 3: Problems
PART TWO: Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization
PART TWO: Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization
Tutorial: Using Molecular Models to Understand Structure
Tutorial: Using Molecular Models to Understand Structure
4: Isomers: The Arrangement of Atoms in Space
Introduction: Isomers: The Arrangement of Atoms in Space
4.1: Geometric Isomers Result from Restricted Rotation
4.2: Using the E,Z System to Name Geometric Isomers
4.3: A Chiral Object Has a Nonsuperimposable Mirror Image
4.4: A Chiral Center is a Cause of Chirality in a Molecule
4.5: Isomers with One Chiral Center
4.6: Chiral Centers and Stereocenters
4.7: How to Draw Enantiomers
4.8: Naming Enantiomers by the R,S System
4.9: Chiral Compounds Are Optically Active
4.10: How Specific Rotation is Measured
4.11: Enantiomeric Excess
4.12: Compounds with More than One Chiral Center
4.13: Meso Compounds Have Chiral Centers but Are Optically Inactive
4.14: How to Name Isomers with More than One Chiral Center
4.15: Nitrogen and Phosphorus Atoms Can Be Chiral Centers
4.16: Receptors
4.17: How Enantiomers Can Be Separated
Chapter 4: Essential Concepts
Chapter 4: Problems
Tutorial: Interconverting Structural Representations
Tutorial: Interconverting Structural Representations
5: Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics
Introduction: Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics
5.1: Molecular Formulas and the Degree of Unsaturation
5.2: Naming Alkenes
5.3: The Structure of Alkenes
5.4: How An Organic Compound Reacts Depends on Its Functional Group
5.5: How Alkenes React • Curved Arrows Show the Flow of Electrons
5.6: Thermodynamics: How Much Product is Formed?
5.7: Increasing the Amount of Product Formed in a Reaction
5.8: Calculating ΔH° Values
5.9: Using ΔH° Values to Determine the Relative Stabilities of Alkenes
5.10: Kinetics: How Fast is the Product Formed?
5.11: The Rate of a Chemical Reaction
5.12: A Reaction Coordinate Diagram Describes the Energy Changes That Take Place During a Reaction
5.13: Catalysis
5.14: Catalysis by Enzymes
Chapter 5: Essential Concepts
Chapter 5: Problems
Tutorial: Drawing Curved Arrows
Tutorial: Drawing Curved Arrows
Tutorial: Kinetics
Tutorial: Kinetics
6: The Reactions of Alkenes • The Stereochemistry of Addition Reactions
Introduction: The Reactions of Alkenes • The Stereochemistry of Addition Reactions
6.1: The Addition of a Hydrogen Halide to an Alkene
6.2: Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon
6.3: What Does the Structure of the Transition State Look Like?
6.4: Electrophilic Addition Reactions Are Regioselective
6.5: The Addition of Water to an Alkene
6.6: The Addition of an Alcohol to an Alkene
6.7: A Carbocation Will Rearrange if It Can Form a More Stable Carbocation
6.8: The Addition of Borane to an Alkene: Hydroboration–Oxidation
6.9: The Addition of a Halogen to an Alkene
6.10: The Addition of a Peroxyacid to an Alkene
6.11: Converting an Alkene to an Alcohol without a Carbocation Rearrangement
6.12: Addition of a Carbene to an Alkene
6.13: The Addition of Ozone to an Alkene: Ozonolysis
6.14: Summary of the Products Formed in the First Step of an Electrophilic Addition Reaction
6.15: Regioselective, Stereoselective, and Stereospecific Reactions
6.16: The Stereochemistry of Electrophilic Addition Reactions
6.17: The Stereochemistry of Enzyme-Catalyzed Reactions
6.18: Biological Molecules Can Distinguish Enantiomers
6.19: Reactions and Synthesis
6.20: Chiral Synthesis
Chapter 6: Essential Concepts
Chapter 6: Summary of Reactions
Chapter 6: Problems
Tutorial: An Overview of Functional Groups and How They React
Tutorial: An Overview of Functional Groups and How They React
7: The Reactions of Alkynes • An Introduction to Multistep Synthesis
Introduction: The Reactions of Alkynes • An Introduction to Multistep Synthesis
7.1: Naming Alkynes
7.2: Naming Compounds with More Than One Functional Group
7.3: The Structure of Alkynes
7.4: The Physical Properties of Unsaturated Hydrocarbons
7.5: The Reactivity of Alkynes
7.6: The Addition of Hydrogen Halides and Halogens to an Alkyne
7.7: The Addition of Water to an Alkyne
7.8: The Addition of Borane to an Alkyne: Hydroboration–Oxidation
7.9: The Addition of Hydrogen to an Alkyne
7.10: A Hydrogen Bonded to an sp Carbon is “Acidic”
7.11: Synthesis Using Acetylide Ions
7.12: Designing A Synthesis I: An Introduction to Multistep Synthesis
Chapter 7: Essential Concepts
Chapter 7: Summary of Reactions
Chapter 7: Problems
8: Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity • Electronic Effects
Introduction: Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity • Electronic Effects
8.1: Delocalized Electrons Explain Benzene’s Structure
8.2: The Bonding in Benzene
8.3: Resonance Contributors and the Resonance Hybrid
8.4: How to Draw Resonance Contributors
8.5: The Predicted Stabilities of Resonance Contributors
8.6: Delocalization Energy is the Additional Stability Delocalized Electrons Give to a Compound
8.7: More About Delocalized Electrons and Increased Stability
8.8: A Molecular Orbital Description of Stability
8.9: Benzene is an Aromatic Compound
8.10: The Two Criteria for Aromaticity
8.11: Applying the Criteria for Aromaticity
8.12: A Molecular Orbital Description of Aromaticity
8.13: Aromatic Heterocyclic Compounds
8.14: Delocalized Electrons Affect pKa Values
8.15: Electronic Effects
8.16: Delocalized Electrons Can Affect the Product of a Reaction
8.17: Reactions of Dienes
8.18: Thermodynamic Versus Kinetic Control
8.19: The Diels–Alder Reaction is a 1,4-Addition Reaction
8.20: Retrosynthetic Analysis of the Diels–Alder Reaction
8.21: Organizing What We Know About the Reactions of Organic Compounds (Group I)
Chapter 8: Essential Concepts
Chapter 8: Summary of Reactions
Chapter 8: Problems
Tutorial: Drawing Resonance Contributors
Tutorial: Drawing Resonance Contributors
PART THREE: Substitution and Elimination Reactions
PART THREE: Substitution and Elimination Reactions
9: Substitution and Elimination Reactions of Alkyl Halides
Introduction: Substitution and Elimination Reactions of Alkyl Halides
9.1: The SN2 Reaction
9.2: Factors That Affect SN2 Reactions
9.3: The SN1 Reaction
9.4: Factors That Affect SN1 Reactions
9.5: Competition Between SN2 and SN1 Reactions
9.6: Elimination Reactions of Alkyl Halides
9.7: The E2 Reaction
9.8: The E1 Reaction
9.9: Competition Between E2 and E1 Reactions
9.10: E2 and E1 Reactions Are Stereoselective
9.11: Elimination from Substituted Cyclohexanes
9.12: Predicting the Products of the Reaction of an Alkyl Halide with a Nucleophile/Base
9.13: Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides
9.14: Solvent Effects
9.15: Substitution and Elimination Reactions in Synthesis
9.16: Intermolecular Versus Intramolecular Reactions
9.17: Designing a Synthesis II: Approaching the Problem
Chapter 9: Essential Concepts
Chapter 9: Summary of Reactions
Chapter 9: Problems
10: Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds • An Introduction to Organometallic Compounds
Introduction: Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds • An Introduction to Organometallic Compounds
10.1: Nucleophilic Substitution Reactions of Alcohols: Forming Alkyl Halides
10.2: Other Methods Used to Convert Alcohols into Alkyl Halides
10.3: Converting an Alcohol Into a Sulfonate Ester
10.4: How Cells Activate Alcohols
10.5: Elimination Reactions of Alcohols: Dehydration
10.6: Oxidation of Alcohols
10.7: Nucleophilic Substitution Reactions of Ethers
10.8: Nucleophilic Substitution Reactions of Epoxides
10.9: Amines Do Not Undergo Substitution or Elimination Reactions
10.10: Quaternary Ammonium Hydroxides
10.11: Thiols, Sulfides, and Sulfonium Ions
10.12: Methylating Agents Used by Chemists versus Those Used by Cells
10.13: An Introduction to Organometallic Compounds
10.14: Organolithium and Organomagnesium Compounds
10.15: Organocuprates
10.16: Organizing What We Know About the Reactions of Organic Compounds (Group II)
Chapter 10: Essential Concepts
Chapter 10: Summary of Reactions
Chapter 10: Problems
11: Radicals
Introduction: Radicals
11.1: Alkanes Are Unreactive Compounds
11.2: The Chlorination and Bromination of Alkanes
11.3: Radical Stability Depends on the Number of Alkyl Groups Attached to the Carbon with the Unpaired Electron
11.4: The Distribution of Products Depends on Probability and Reactivity
11.5: The Reactivity–Selectivity Principle
11.6: Formation of Explosive Peroxides
11.7: The Addition of Radicals to an Alkene
11.8: The Stereochemistry of Radical Substitution and Radical Addition Reactions
11.9: Radical Substitution of Allylic and Benzylic Hydrogens
11.10: Designing a Synthesis III: More Practice with Multistep Synthesis
11.11: Introduction to Chain-Growth Polymers
11.12: Radical Reactions in Biological Systems
11.13: Radicals and Stratospheric Ozone
Chapter 11: Essential Concepts
Chapter 11: Summary of Reactions
Chapter 11: Problems
Tutorial: Drawing Curved Arrows in Radical Systems
Tutorial: Drawing Curved Arrows in Radical Systems
Tutorial: Synthesizing Organic Compounds I
Tutorial: Synthesizing Organic Compounds I
PART FOUR: Identification of Organic Compounds
PART FOUR: Identification of Organic Compounds
12: Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy
Introduction: Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy
12.1: Mass Spectrometry
12.2: The Mass Spectrum • Fragmentation
12.3: Using the m/z Value of the Molecular Ion to Calculate the Molecular Formula
12.4: Isotopes in Mass Spectrometry
12.5: High-Resolution Mass Spectrometry Can Reveal Molecular Formulas
12.6: The Fragmentation Patterns of Functional Groups
12.7: Other Ionization Methods
12.8: Gas Chromatography–Mass Spectrometry
12.9: Spectroscopy and the Electromagnetic Spectrum
12.10: Infrared Spectroscopy
12.11: Characteristic Infrared Absorption Bands
12.12: The Intensity of Absorption Bands
12.13: The Position of Absorption Bands
12.14: Factors Affecting the Position and Shape of an Absorption Band
12.15: C—H Absorption Bands
12.16: The Absence of Absorption Bands
12.17: Some Vibrations are Infrared Inactive
12.18: How to Interpret an Infrared Spectrum
12.19: Ultraviolet and Visible Spectroscopy
12.20: The Beer–Lambert Law
12.21: The Effect of Conjugation on λmax
12.22: The Visible Spectrum and Color
12.23: Some Uses of UV/Vis Spectroscopy
Chapter 12: Essential Concepts
Chapter 12: Problems
13: NMR Spectroscopy
Introduction: NMR Spectroscopy
13.1: An Introduction to NMR Spectroscopy
13.2: Fourier Transform NMR
13.3: Shielding Causes Different Protons to Show Signals at Different Frequencies
13.4: The Number of Signals in an 1H NMR Spectrum
13.5: The Time Dependence of NMR Spectroscopy
13.6: The Chemical Shift Tells How Far the Signal Is from the Reference Signal
13.7: The Relative Positions of 1H NMR Signals
13.8: The Characteristic Values of Chemical Shifts
13.9: Hydrogens Bonded to sp2 and sp Carbons
13.10: The Integration of NMR Signals Reveals the Relative Number of Protons Causing Each Signal
13.11 Signal Splitting Is Described by the N + 1 Rule
13.12: What Causes Splitting?
13.13: More Examples of 1H NMR Spectra
13.14: Coupling Constants Identify Coupled Protons
13.15: Splitting Diagrams Explain the Multiplicity of a Signal
13.16: Enantiotopic and Diastereotopic Hydrogens
13.17: Protons Bonded to Oxygen and Nitrogen
13.18: The Use of Deuterium in 1H NMR Spectroscopy
13.19: The Resolution of 1H NMR Spectra
13.20: 13C NMR Spectroscopy
13.21: DEPT 13C NMR Spectra
13.22: Two-Dimensional NMR Spectroscopy
13.23: NMR Used in Medicine is Called Magnetic Resonance Imaging
13.24: X-Ray Crystallography
Chapter 13: Essential Concepts
Chapter 13: Problems
PART FIVE: Carbonyl Compounds
PART FIVE: Carbonyl Compounds
14: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
Introduction: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
14.1: Naming Carboxylic Acids and Carboxylic Acid Derivatives
14.2: The Structures of Carboxylic Acids and Carboxylic Acid Derivatives
14.3: The Physical Properties of Carbonyl Compounds
14.4: How Carboxylic Acids and Carboxylic Acid Derivatives React
14.5: The Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives
14.6: Reactions of Acyl Chlorides
14.7: Reactions of Acid Anhydrides
14.8: Reactions of Esters
14.9: Acid-Catalyzed Ester Hydrolysis and Transesterification
14.10: Hydroxide-Ion-Promoted Ester Hydrolysis
14.11: Reactions of Carboxylic Acids
14.12: Reactions of Amides
14.13: Acid-Catalyzed Amide Hydrolysis and Alcoholysis
14.14: Hydroxide-Ion-Promoted Hydrolysis of Amides
14.15: Introduction to Step-Growth Polymers
14.16: Hydrolysis of an Imide: A Way to Synthesize a Primary Amine
14.17: Nitriles
14.18: Dicarboxylic Acids
14.19: How Chemists Activate Carboxylic Acids
14.20: How Cells Activate Carboxylic Acids
Chapter 14: Essential Concepts
Chapter 14: Summary of Reactions
Chapter 14: Problems
15: Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
Introduction: Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
15.1: Naming Aldehydes and Ketones
15.2: The Relative Reactivities of Carbonyl Compounds
15.3: How Aldehydes and Ketones React
15.4: Reactions of Carbonyl Compounds with Carbon Nucleophiles
15.5: Reactions of Carbonyl Compounds with Hydride Ion
15.6: More About Reduction Reactions
15.7: Chemoselective Reactions
15.8: Reactions of Aldehydes and Ketones with Nitrogen Nucleophiles
15.9: Reactions of Aldehydes and Ketones with Oxygen Nucleophiles
15.10: Protecting Groups
15.11: Reactions of Aldehydes and Ketones with Sulfur Nucleophiles
15.12: Reactions of Aldehydes and Ketones with a Peroxyacid
15.13: The Wittig Reaction Forms an Alkene
15.14: Designing a Synthesis IV: Disconnections, Synthons, and Synthetic Equivalents
15.15: Nucleophilic Addition to alpha, Beta-Unsaturated Aldehydes and Ketones
15.16: Nucleophilic Addition to alpha, Beta-Unsaturated Carboxylic Acid Derivatives
15.17: Conjugate Addition Reactions in Biological Systems
Chapter 15: Essential Concepts
Chapter 15: Summary of Reactions
Chapter 15: Problems
Tutorial: Predicting Mechanisms
Tutorial: Predicting Mechanisms
16: Reactions at the alpha-Carbon
Introduction: Reactions at the alpha-Carbon
16.1: An alpha-Hydrogen Is Acidic
16.2: Keto–Enol Tautomers
16.3: Keto–Enol Interconversion
16.4: Halogenating the alpha-Carbon of Aldehydes and Ketones
16.5: Halogenating the alpha-Carbon of Carboxylic Acids
16.6: Forming an Enolate Ion
16.7: Alkylating the alpha-Carbon
16.8: Alkylating and Acylating the alpha-Carbon via an Enamine Intermediate
16.9: Alkylating the Beta-Carbon
16.10: An Aldol Addition Forms a Beta-Hydroxyaldehyde or a Beta-Hydroxyketone
16.11: Dehydrating Aldol Addition Products Forms alpha, Beta-Unsaturated Aldehydes and Ketones
16.12: A Crossed Aldol Addition
16.13: A Claisen Condensation Forms a Beta-Keto Ester
16.14: Other Crossed Condensations
16.15: Intramolecular Condensations and Intramolecular Aldol Additions
16.16: The Robinson Annulation
16.17: Removing CO2 from the alpha-Carbon of a Carboxylic Acid
16.18: Synthesizing a Carboxylic Acid
16.19: Synthesizing a Methyl Ketone
16.20: Designing a Synthesis V: Making New Carbon–Carbon Bonds
16.21: Reactions at the alpha-Carbon in Living Systems
16.22: Organizing What We Know About the Reactions of Organic Compounds (Group III)
Chapter 16: Essential Concepts
Chapter 16: Summary of Reactions
Chapter 16: Problems
Tutorial: Synthesizing Organic Compounds II
Tutorial: Synthesizing Organic Compounds II
PART SIX: Aromatic Compounds, Palladium-Catalyzed Coupling Reactions, and Metathesis
PART SIX: Aromatic Compounds, Palladium-Catalyzed Coupling Reactions, and Metathesis
17: Reactions of Benzene and Substituted Benzenes
Introduction: Reactions of Benzene and Substituted Benzenes
17.1: Naming Monosubstituted Benzenes
17.2: How Benzene Reacts
17.3: The General Mechanism for Electrophilic Aromatic Substitution Reactions
17.4: Halogenation of Benzene
17.5: Nitration of Benzene
17.6: Sulfonation of Benzene
17.7: Friedel–Crafts Acylation of Benzene
17.8: Friedel–Crafts Alkylation of Benzene
17.9: Alkylating Benzene via Acylation–Reduction
17.10: Using Coupling Reactions to Alkylate Benzene
17.11: How Some Substituents on a Benzene Ring Can Be Chemically Changed
17.12: Naming Disubstituted and Polysubstituted Benzenes
17.13: How Substituents Affect Reactivity
17.14: The Effect of Substituents on Orientation
17.15: The Ortho–Para Ratio
17.16: Additional Considerations Regarding Substituent Effects
17.17: Designing a Synthesis VI: Synthesizing Monosubstituted and Disubstituted Benzenes
17.18: Synthesizing Trisubstituted Benzenes
17.19: Synthesizing Substituted Benzenes Using Arenediazonium Salts
17.20: Azobenzenes
17.21: The Mechanism for the Formation of a Diazonium Ion
17.22: Nucleophilic Aromatic Substitution
17.23: Benzyne
17.24: Designing a Synthesis VII: The Synthesis of Cyclic Compounds
17.25: Arene Oxides
Chapter 17: Essential Concepts
Chapter 17: Summary of Reactions
Chapter 17: Problems
18: More About Amines • Reactions of Heterocyclic Aromatic Compounds
Introduction: More About Amines • Reactions of Heterocyclic Aromatic Compounds
18.1: More About Naming Amines
18.2: More About the Acid–Base Properties of Amines
18.3: More About the Reactions of Amines
18.4: Synthesizing Amines
18.5: Aromatic Five-Membered Ring Heterocycles
18.6: Aromatic Six-Membered Ring Heterocycles
18.7: Some Heterocyclic Amines Have Important Roles in Nature
18.8: Organizing What We Know About the Reactions of Organic Compounds (Group IV)
Chapter 18: Essential Concepts
Chapter 18: Summary of Reactions
Chapter 18: Problems
19: Coupling Reactions and Metathesis
Introduction: Coupling Reactions and Metathesis
19.1: Palladium-Catalyzed Coupling Reactions
19.2: Stille Coupling
19.3: Negishi Coupling
19.4: Sonogashira Coupling
19.5: Suzuki Coupling
19.6: Heck Coupling
19.7: Metathesis
Chapter 19: Essential Concepts
Chapter 19: Summary of Reactions
Chapter 19: Problems
PART SEVEN: Bioorganic Compounds
PART SEVEN: Bioorganic Compounds
20: The Organic Chemistry of Carbohydrates
Introduction: The Organic Chemistry of Carbohydrates
20.1: Classifying Carbohydrates
20.2: Naming Fischer Projections
20.3: The D and L Notation
20.4: The Configurations of Aldoses
20.5: The Configurations of Ketoses
20.6: The Reactions of Monosaccharides in Basic Solution
20.7: Oxidizing and Reducing Monosaccharides
20.8: Lengthening the Chain: The Kiliani–Fischer Synthesis
20.9: Shortening the Chain: The Wohl Degradation
20.10: The Stereochemistry of Glucose: The Fischer Proof
20.11: Monosaccharides Form Cyclic Hemiacetals
20.12: Glucose Is the Most Stable Aldohexose
20.13: Formation of Glycosides
20.14: The Anomeric Effect
20.15: Reducing and Nonreducing Sugars
20.16: Disaccharides
20.17: Polysaccharides
20.18: Some Naturally Occurring Compounds Derived from Carbohydrates
20.19: Carbohydrates on Cell Surfaces
20.20: Synthetic Sweeteners
Chapter 20: Essential Concepts
Chapter 20: Summary of Reactions
Chapter 20: Problems
21: Amino Acids, Peptides, and Proteins
Introduction: Amino Acids, Peptides, and Proteins
21.1: Naming Amino Acids
21.2: The Configuration of Amino Acids
21.3: Acid–Base Properties of Amino Acids
21.4: The Isoelectric Point
21.5: Separating Amino Acids
21.6: Synthesis of Amino Acids
21.7: Resolution of Racemic Mixtures of Amino Acids
21.8: Peptide Bonds and Disulfide Bonds
21.9: Some Interesting Peptides
21.10: The Strategy of Peptide Bond Synthesis: N-Protection and C-Activation
21.11: Automated Peptide Synthesis
21.12: An Introduction to Protein Structure
21.13: How to Determine the Primary Structure of a Polypeptide or a Protein
21.14: Secondary Structure
21.15: Tertiary Structure
21.16: Quaternary Structure
21.17: Protein Denaturation
Chapter 21: Essential Concepts
Chapter 21: Problems
22: Catalysis in Organic Reactions and in Enzymatic Reactions
Introduction: Catalysis in Organic Reactions and in Enzymatic Reactions
22.1: Catalysis in Organic Reactions
22.2: Acid Catalysis
22.3: Base Catalysis
22.4: Nucleophilic Catalysis
22.5: Metal-Ion Catalysis
22.6: Intramolecular Reactions
22.7: Intramolecular Catalysis
22.8: Catalysis in Biological Reactions
22.9: An Enzyme-Catalyzed Reaction Reminiscent of Acid-Catalyzed Amide Hydrolysis
22.10: Another Enzyme-Catalyzed Reaction Reminiscent of Acid-Catalyzed Amide Hydrolysis
22.11: An Enzyme-Catalyzed Reaction That Involves Two Sequential SN2 Reactions
22.12: An Enzyme-Catalyzed Reaction Reminiscent of the Base-Catalyzed Enediol Rearrangement
22.13: An Enzyme-Catalyzed Reaction Reminiscent of a Retro-Aldol Addition
Chapter 22: Essential Concepts
Chapter 22: Problems
23: The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins
Introduction: The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins
23.1: Niacin (Vitamin B3): The Vitamin Needed for Many Redox Reactions
23.2: Riboflavin (Vitamin B2): Another Vitamin Used in Redox Reactions
23.3: Thiamine (Vitamin B1): The Vitamin Needed for Acyl Group Transfer
23.4: Biotin (Vitamin B7 or Vitamin H): The Vitamin Needed for Carboxylation of an a-Carbon
23.5: Pyridoxine (Vitamin B6): The Vitamin Needed for Amino Acid Transformations
23.6: Vitamin B12: The Vitamin Needed for Certain Isomerizations
23.7: Folic Acid: The Vitamin Needed for One-Carbon Transfer
23.8: Vitamin K: The Vitamin Needed for Carboxylation of Glutamate
Chapter 23: Essential Concepts
Chapter 23: Problems
24: The Organic Chemistry of the Metabolic Pathways
Introduction: The Organic Chemistry of the Metabolic Pathways
24.1: ATP is Used for Phosphoryl Transfer Reactions
24.2: The “High-Energy” Character of Phosphoanhydride Bonds
24.3: Why ATP Is Kinetically Stable in a Cell
24.4: The Four Stages of Catabolism
24.5: The Catabolism of Fats: Stages 1 and 2
24.6: The Catabolism of Carbohydrates: Stages 1 and 2
24.7: The Fate of Pyruvate
24.8: The Catabolism of Proteins: Stages 1 and 2
24.9: The Citric Acid Cycle: Stage 3
24.10: Oxidative Phosphorylation: Stage 4
24.11: Anabolism
24.12: Biosynthesis of Fats
24.13: Biosynthesis of Glucose: Gluconeogenesis
24.14: Regulating Metabolic Pathways
24.15: Biosynthesis of Amino Acids
Chapter 24: Essential Concepts
Chapter 24: Problems
25: The Organic Chemistry of Lipids
Introduction: The Organic Chemistry of Lipids
25.1: Fatty Acids Are Long-Chain Carboxylic Acids
25.2: Waxes Are High-Molecular-Weight Esters
25.3: Fats and Oils Are Triglycerides
25.4: Phospholipids Are Components of Cell Membranes
25.5: Prostaglandins Regulate Physiological Responses
25.6: Terpenes Contain Carbon Atoms in Multiples of Five
25.7: How Terpenes Are Biosynthesized
25.8: How Nature Synthesizes Cholesterol
25.9: Steroids
25.10: Synthetic Steroids
Chapter 25: Essential Concepts
Chapter 25: Problems
26: The Chemistry of the Nucleic Acids
Introduction: The Chemistry of the Nucleic Acids
26.1: Nucleosides and Nucleotides
26.2: Nucleic Acids Are Composed of Nucleotide Subunits
26.3: The Secondary Structure of DNA
26.4: Why DNA Does Not Have a 2'-OH Group
26.5: The Biosynthesis of DNA Is Called Replication
26.6: DNA and Heredity
26.7: The Biosynthesis of RNA Is Called Transcription
26.8: The RNAs Used for Protein Biosynthesis
26.9: The Biosynthesis of Proteins Is Called Translation
26.10: CRISPR
26.11: Why DNA Contains Thymine Instead of Uracil
26.12: Antiviral Drugs
26.13: COVID-19
26.14: How the Base Sequence of DNA Is Determined
26.15: Genetic Engineering
Chapter 26: Essential Concepts
Chapter 26: Problems
PART EIGHT: Special Topics in Organic Chemistry
PART EIGHT: Special Topics in Organic Chemistry
27: Synthetic Polymers
Introduction: Synthetic Polymers
27.1: The Two Major Classes of Synthetic Polymers
27.2: Chain-Growth Polymers
27.3: Radical Polymerization
27.4: Cationic Polymerization
27.5: Anionic Polymerization
27.6: Ring-Opening Polymerizations
27.7: Stereochemistry of Polymerization • Ziegler–Natta Catalysts
27.8: Polymerization of Dienes
27.9: Copolymers
27.10: Step-Growth Polymers
27.11: Classes of Step-Growth Polymers
27.12: Physical Properties of Polymers
27.13: Recycling Polymers
27.14: Compostable Polymers
Chapter 27: Essential Concepts
Chapter 27: Problems
28: Pericyclic Reactions
Introduction: Pericyclic Reactions
28.1: Three Types of Pericyclic Reactions
28.2: Molecular Orbitals and Orbital Symmetry
28.3: Electrocyclic Reactions
28.4: Cycloaddition Reactions
28.5: Sigmatropic Rearrangements
28.6: Summary of the Selection Rules for Pericyclic Reactions
28.7: Pericyclic Reactions in Biological Systems
Chapter 28: Essential Concepts
Chapter 28: Problems
Appendix I: pKa Values
Appendix I: pKa Values
Appendix II: Summary of Methods Used to Synthesize a Particular Functional Group
Appendix II: Summary of Methods Used to Synthesize a Particular Functional Group
Appendix III: Summary of Methods Employed to Form Carbon-Carbon Bonds
Appendix III: Summary of Methods Employed to Form Carbon-Carbon Bonds
Appendix IV: Spectroscopy Tables
Appendix IV: Spectroscopy Tables
Appendix V: Physical Properties of Organic Compounds
Appendix V: Physical Properties of Organic Compounds
Appendix VI: Answers to Selected Problems
Chapter 1: Answers to Selected Problems
Chapter 2: Answers to Selected Problems
Chapter 3: Answers to Selected Problems
Chapter 4: Answers to Selected Problems
Chapter 5: Answers to Selected Problems
Chapter 6: Answers to Selected Problems
Chapter 7: Answers to Selected Problems
Chapter 8: Answers to Selected Problems
Chapter 9: Answers to Selected Problems
Chapter 10: Answers to Selected Problems
Chapter 11: Answers to Selected Problems
Chapter 12: Answers to Selected Problems
Chapter 13: Answers to Selected Problems
Chapter 14: Answers to Selected Problems
Chapter 15: Answers to Selected Problems
Chapter 16: Answers to Selected Problems
Chapter 17: Answers to Selected Problems
Chapter 18: Answers to Selected Problems
Chapter 19: Answers to Selected Problems
Chapter 20: Answers to Selected Problems
Chapter 21: Answers to Selected Problems
Chapter 22: Answers to Selected Problems
Chapter 23: Answers to Selected Problems
Chapter 24: Answers to Selected Problems
Chapter 25: Answers to Selected Problems
Chapter 26: Answers to Selected Problems
Chapter 27: Answers to Selected Problems
Chapter 28: Answers to Selected Problems
Math and Chemistry-Based Glossary
Math and Chemistry-Based Glossary
Useful References
To the Student
Organizing What We Know About the Reactions of Organic Chemistry
Periodic Table of the Elements
Common Functional Groups
Approximate pKa Values
Common Symbols and Abbreviations
Credits
Credits
Glossary