Fundamentals of Organic Chemistry, 7th Edition

Front Cover
Title Page
Copyright
CONTENTS
1 Structure and Bonding; Acids and Bases
	1.1 Atomic Structure
	1.2 Atomic Structure: Electron Configurations
	1.3 Development of Chemical Bonding Theory
	1.4 The Nature of Chemical Bonds
	1.5 Forming Covalent Bonds: Valence Bond Theory
	1.6 sp3 Hybrid Orbitals and the Structure of Methane
	1.7 sp3 Hybrid Orbitals and the Structure of Ethane
	1.8 Other Kinds of Hybrid Orbitals: sp2 and sp
	1.9 Polar Covalent Bonds: Electronegativity
	1.10 Acids and Bases: The Brønsted–Lowry Definition
	1.11 Organic Acids and Organic Bases
	1.12 Acids and Bases: The Lewis Definition
	INTERLUDE: Organic Foods: Risk versus Benefit
	Summary and Key Words
	Exercises
2 Alkanes: The Nature of Organic Compounds
	2.1 Functional Groups
	2.2 Alkanes and Alkyl Groups: Isomers
	2.3 Naming Branched-Chain Alkanes
	2.4 Properties of Alkanes
	2.5 Conformations of Ethane
	2.6 Drawing Chemical Structures
	2.7 Cycloalkanes
	2.8 Cis–Trans Isomerism in Cycloalkanes
	2.9 Conformations of Some Cycloalkanes
	2.10 Axial and Equatorial Bonds in Cyclohexane
	2.11 Conformational Mobility of Cyclohexane
	INTERLUDE: Where Do Drugs Come From?
	Summary and Key Words
	Exercises
3 Alkenes and Alkynes: The Nature of Organic Reactions
	3.1 Naming Alkenes and Alkynes
	3.2 Electronic Structure of Alkenes
	3.3 Cis–Trans Isomers of Alkenes
	3.4 Sequence Rules: The E,Z Designation
	3.5 Kinds of Organic Reactions
	3.6 How Reactions Occur: Mechanisms
	3.7 The Mechanism of an Organic Reaction: Addition of HCl to Ethylene
	3.8 Describing a Reaction: Transition States and Intermediates
	3.9 Describing a Reaction: Catalysis
	INTERLUDE: Terpenes: Naturally Occurring Alkenes
	Summary and Key Words
	Exercises
4 Reactions of Alkenes and Alkynes
	4.1 Addition of HX to Alkenes: Markovnikov’s Rule
	4.2 Carbocation Structure and Stability
	4.3 Addition of Water to Alkenes
	4.4 Addition of Halogens to Alkenes
	4.5 Reduction of Alkenes: Hydrogenation
	4.6 Oxidation of Alkenes: Epoxidation, Hydroxylation, and Cleavage
	4.7 Addition of Radicals to Alkenes: Polymers
	4.8 Conjugated Dienes
	4.9 Stability of Allylic Carbocations: Resonance
	4.10 Drawing and Interpreting Resonance Forms
	4.11 Alkynes and Their Reactions
	INTERLUDE: Natural Rubber
	Summary and Key Words
	Summary of Reactions
	Exercises
5 Aromatic Compounds
	5.1 Structure of Benzene
	5.2 Naming Aromatic Compounds
	5.3 Electrophilic Aromatic Substitution Reactions: Bromination
	5.4 Other Electrophilic Aromatic Substitution Reactions
	5.5 The Friedel–Crafts Alkylation and Acylation Reactions
	5.6 Substituent Effects in Electrophilic Aromatic Substitution
	5.7 An Explanation of Substituent Effects
	5.8 Oxidation and Reduction of Aromatic Compounds
	5.9 Other Aromatic Compounds
	5.10 Organic Synthesis
	INTERLUDE: Aspirin, NSAIDs, and COX-2 Inhibitors
	Summary and Key Words
	Summary of Reactions
	Exercises
6 Stereochemistry at Tetrahedral Centers
	6.1 Enantiomers and the Tetrahedral Carbon
	6.2 The Reason for Handedness in Molecules: Chirality
	6.3 Optical Activity
	6.4 Pasteur’s Discovery of Enantiomers
	6.5 Sequence Rules for Specifying Configuration
	6.6 Diastereomers
	6.7 Meso Compounds
	6.8 Racemic Mixtures and the Resolution of Enantiomers
	6.9 A Brief Review of Isomerism
	6.10 Chirality in Nature and Chiral Environments
	INTERLUDE: Chiral Drugs
	Summary and Key Words
	Exercises
7 Organohalides: Nucleophilic Substitutions and Eliminations
	7.1 Naming Alkyl Halides
	7.2 Preparing Alkyl Halides
	7.3 Reactions of Alkyl Halides: Grignard Reagents
	7.4 Nucleophilic Substitution Reactions
	7.5 Substitutions: The S[sub(N)]2 Reaction
	7.6 Substitutions: The S[sub(N)]1 Reaction
	7.7 Eliminations: The E[sub(2)] Reaction
	7.8 Eliminations: The E1 and E1cB Reactions
	7.9 A Summary of Reactivity: S[sub(N)]1, S[sub(N)]2, E1, E1cB, and E2
	7.10 Substitution and Elimination Reactions in Living Organisms
	INTERLUDE: Naturally Occurring Organohalides
	Summary and Key Words
	Summary of Reactions
	Exercises
8 Alcohols, Phenols, Ethers, and Their Sulfur Analogs
	8.1 Naming Alcohols, Phenols, and Ethers
	8.2 Properties of Alcohols and Phenols: Hydrogen Bonding and Acidity
	8.3 Synthesis of Alcohols from Carbonyl Compounds
	8.4 Reactions of Alcohols
	8.5 Reactions of Phenols
	8.6 Reactions of Ethers
	8.7 Cyclic Ethers: Epoxides
	8.8 Thiols and Sulfides
	INTERLUDE: Epoxy Resins and Adhesives
	Summary and Key Words
	Summary of Reactions
	Exercises
9 Aldehydes and Ketones: Nucleophilic Addition Reactions
	9.1 The Nature of Carbonyl Compounds
	9.2 Naming Aldehydes and Ketones
	9.3 Synthesis of Aldehydes and Ketones
	9.4 Oxidation of Aldehydes
	9.5 Nucleophilic Addition Reactions
	9.6 Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation
	9.7 Nucleophilic Addition of Water: Hydrate Formation
	9.8 Nucleophilic Addition of Alcohols: Acetal Formation
	9.9 Nucleophilic Addition of Amines: Imine Formation
	9.10 Conjugate Nucleophilic Addition Reactions
	INTERLUDE: Vitamin C
	Summary and Key Words
	Summary of Reactions
	Exercises
10 Carboxylic Acids and Derivatives: Nucleophilic Acyl Substitution Reactions
	10.1 Naming Carboxylic Acids and Derivatives
	10.2 Occurrence and Properties of Carboxylic Acids and Derivatives
	10.3 Acidity of Carboxylic Acids
	10.4 Synthesis of Carboxylic Acids
	10.5 Nucleophilic Acyl Substitution Reactions
	10.6 Carboxylic Acids and Their Reactions
	10.7 Acid Halides and Their Reactions
	10.8 Acid Anhydrides and Their Reactions
	10.9 Esters and Their Reactions
	10.10 Amides and Their Reactions
	10.11 Nitriles and Their Reactions
	10.12 Biological Carboxylic Acid Derivatives: Thioesters and Acyl Phosphates
	10.13 Polymers from Carbonyl Compounds: Polyamides and Polyesters
	INTERLUDE: -Lactam Antibiotics
	Summary and Key Words
	Summary of Reactions
	Exercises
11 Carbonyl Alpha-Substitution Reactions and Condensation Reactions
	11.1 Keto–Enol Tautomerism
	11.2 Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions
	11.3 Alpha Halogenation of Aldehydes and Ketones
	11.4 Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
	11.5 Reactivity of Enolate Ions
	11.6 Alkylation of Enolate Ions
	11.7 Carbonyl Condensation Reactions
	11.8 Condensations of Aldehydes and Ketones: The Aldol Reaction
	11.9 Dehydration of Aldol Products: Synthesis of Enones
	11.10 Condensations of Esters: The Claisen Condensation Reaction
	11.11 Some Biological Carbonyl Reactions
	INTERLUDE: Barbiturates
	Summary and Key Words
	Summary of Reactions
	Exercises
12 Amines
	12.1 Naming Amines
	12.2 Structure and Properties of Amines
	12.3 Basicity of Amines
	12.4 Synthesis of Amines
	12.5 Reactions of Amines
	12.6 Heterocyclic Amines
	12.7 Alkaloids: Naturally Occurring Amines
	INTERLUDE: Green Chemistry
	Summary and Key Words
	Summary of Reactions
	Exercises
13 Structure Determination
	13.1 Mass Spectrometry
	13.2 Spectroscopy and the Electromagnetic Spectrum
	13.3 Infrared Spectroscopy of Organic Molecules
	13.4 Interpreting Infrared Spectra
	13.5 Ultraviolet Spectroscopy
	13.6 Interpreting Ultraviolet Spectra: The Effect of Conjugation
	13.7 Nuclear Magnetic Resonance Spectroscopy
	13.8 The Nature of NMR Absorptions
	13.9 Chemical Shifts
	13.10 Chemical Shifts in [sup(1)]H NMR Spectra
	13.11 Integration of [sup(1)]H NMR Spectra: Proton Counting
	13.12 Spin–Spin Splitting in [sup(1)]H NMR Spectra
	13.13 Uses of [sup(1)]H NMR Spectra
	13.14 13[sub(C)] NMR Spectroscopy
	INTERLUDE: Magnetic Resonance Imaging (MRI)
	Summary and Key Words
	Exercises
14 Biomolecules: Carbohydrates
	14.1 Classification of Carbohydrates
	14.2 Depicting Carbohydrate Stereochemistry: Fischer Projections
	14.3 D,L Sugars
	14.4 Configurations of Aldoses
	14.5 Cyclic Structures of Monosaccharides: Hemiacetal Formation
	14.6 Monosaccharide Anomers: Mutarotation
	14.7 Reactions of Monosaccharides
	14.8 The Eight Essential Monosaccharides
	14.9 Disaccharides
	14.10 Polysaccharides
	14.11 Cell-Surface Carbohydrates and Carbohydrate Vaccines
	INTERLUDE: Sweetness
	Summary and Key Words
	Exercises
15 Biomolecules: Amino Acids, Peptides, and Proteins
	15.1 Structures of Amino Acids
	15.2 Isoelectric Points
	15.3 Peptides and Proteins
	15.4 Covalent Bonding in Peptides
	15.5 Peptide Structure Determination: Amino Acid Analysis
	15.6 Peptide Sequencing: The Edman Degradation
	15.7 Peptide Synthesis
	15.8 Protein Structure
	15.9 Enzymes and Coenzymes
	15.10 How Do Enzymes Work? Citrate Synthase
	INTERLUDE: X-Ray Crystallography
	Summary and Key Words
	Exercises
16 Biomolecules: Lipids and Nucleic Acids
	16.1 Waxes, Fats, and Oils
	16.2 Soaps
	16.3 Phospholipids
	16.4 Steroids
	16.5 Nucleic Acids and Nucleotides
	16.6 Base Pairing in DNA: The Watson–Crick Model
	16.7 Replication of DNA
	16.8 Transcription of DNA
	16.9 Translation of RNA: Protein Biosynthesis
	16.10 DNA Sequencing
	16.11 The Polymerase Chain Reaction
	INTERLUDE: DNA Fingerprinting
	Summary and Key Words
	Exercises
17 The Organic Chemistry of Metabolic Pathways
	17.1 An Overview of Metabolism and Biochemical Energy
	17.2 Catabolism of Fats:  -Oxidation
	17.3 Catabolism of Carbohydrates: Glycolysis
	17.4 The Citric Acid Cycle
	17.5 Catabolism of Proteins: Transamination
	17.6 Some Conclusions about Biological Chemistry
	INTERLUDE: Statin Drugs
	Summary and Key Words
	Exercises
APPENDIX A: Nomenclature of Polyfunctional Organic Compounds
APPENDIX B: Glossary
APPENDIX C: Answers to Selected In-Chapter Problems
INDEX