Organic Chemistry

Cover
Title Page
Copyright
Dedication
Contents
Preface
Chapter 1: A Review of General Chemistry: Electrons, Bonds, and Molecular Properties
	1.1 Introduction to Organic Chemistry
	1.2 The Structural Theory of Matter
	1.3 Electrons, Bonds, and Lewis Structures
	1.4 Identifying Formal Charges
	1.5 Induction and Polar Covalent Bonds
	1.6 Reading Bond-Line Structures
	1.7 Atomic Orbitals
	1.8 Valence Bond Theory
	1.9 Molecular Orbital Theory
	1.10 Hybridized Atomic Orbitals
	1.11 Predicting Molecular Geometry: VSEPR Theory
	1.12 Dipole Moments and Molecular Polarity
	1.13 Intermolecular Forces and Physical Properties
		WorldLinks Biomimicry and Gecko Feet
		BioLinks Drug-Receptor Interactions
	1.14 Solubility
		BioLinks Propofol: The Importance of Drug Solubility
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 2: Molecular Representations
	2.1 Molecular Representations
	2.2 Drawing Bond-Line Structures
	2.3 Identifying Functional Groups
		BioLinks Marine Natural Products
	2.4 Carbon Atoms with Formal Charges
	2.5 Identifying Lone Pairs
	2.6 Three-Dimensional Bond-Line Structures
		BioLinks The Opioids
	2.7 Introduction to Resonance
	2.8 Curved Arrows
	2.9 Formal Charges in Resonance Structures
	2.10 Drawing Resonance Structures via Pattern Recognition
	2.11 Assessing the Relative Importance of Resonance Structures
	2.12 The Resonance Hybrid
	2.13 Delocalized and Localized Lone Pairs
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 3: Acids and Bases
	3.1 Introduction to Brønsted-Lowry Acids and Bases
	3.2 Flow of Electron Density: Curved-Arrow Notation
		BioLinks Antacids and Heartburn
	3.3 Brønsted-Lowry Acidity: Comparing pKa values
		BioLinks Drug Distribution and pKa
	3.4 Brønsted-Lowry Acidity: Factors Affecting the Stability of Anions
	3.5 Brønsted-Lowry Acidity: Assessing the Relative Acidity of Cationic Acids
	3.6 Position of Equilibrium and Choice of Reagents
	3.7 Leveling Effect
	3.8 Solvating Effects
	3.9 Counterions
		WorldLinks Baking Soda versus Baking Powder
	3.10 Lewis Acids and Bases
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 4: Alkanes and Cycloalkanes
	4.1 Introduction to Alkanes
	4.2 Nomenclature of Alkanes
		WorldLinks Pheromones: Chemical Messengers
		BioLinks Naming Drugs
	4.3 Constitutional Isomers of Alkanes
	4.4 Relative Stability of Isomeric Alkanes
	4.5 Sources and Uses of Alkanes
		WorldLinks An Introduction to Polymers
	4.6 Drawing Newman Projections
	4.7 Conformational Analysis of Ethane
 and Propane
	4.8 Conformational Analysis of Butane
		BioLinks Drugs and Their Conformations
	4.9 Cycloalkanes
		BioLinks Cyclopropane as an Inhalation Anesthetic
	4.10 Conformations of Cyclohexane
	4.11 Drawing Chair Conformations
	4.12 Monosubstituted Cyclohexane
	4.13 Disubstituted Cyclohexane
	4.14 cis-trans Stereoisomerism
	4.15 Polycyclic Systems
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS-STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 5: Stereoisomerism
	5.1 Overview of Isomerism
	5.2 Introduction to Stereoisomerism
		WorldLinks The Sense of Smell
	5.3 Designating Configuration Using the Cahn-Ingold-Prelog System
		BioLinks Chiral Drugs
	5.4 Optical Activity
	5.5 Stereoisomeric Relationships: Enantiomers and
 Diastereomers
	5.6 Symmetry and Chirality
	5.7 Fischer Projections
	5.8 Conformationally Mobile Systems
	5.9 Chiral Compounds that Lack a Chiral Center
	5.10 Resolution of Enantiomers
	5.11 E and Z Designations for Diastereomeric Alkenes
		BioLinks Phototherapy Treatment for Neonatal Jaundice
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 6: Chemical Reactivity and Mechanisms
	6.1 Enthalpy
	6.2 Entropy
	6.3 Gibbs Free Energy
		WorldLinks Explosives
		WorldLinks Do Living Organisms Violate the Second Law of Thermodynamics
	6.4 Equilibria
	6.5 Kinetics
		BioLinks Nitroglycerin: An Explosive with Medicinal Properties
		WorldLinks Beer Making
	6.6 Reading Energy Diagrams
	6.7 Nucleophiles and Electrophiles
	6.8 Mechanisms and Arrow Pushing
	6.9 Combining the Patterns of Arrow Pushing
	6.10 Drawing Curved Arrows
	6.11 Carbocation Rearrangements
	6.12 Reversible and Irreversible Reaction Arrows
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 7: Alkyl Halides: Nucleophilic Substitution and Elimination Reactions
	7.1 Introduction to Substitution and Elimination Reactions
	7.2 Nomenclature and Uses of Alkyl Halides
	7.3 SN2 Reactions
		BioLinks Pharmacology and Drug Design
	7.4 Nucleophilic Strength in SN2 Reactions
		BioLinks SN2 Reactions in Biological Systems—Methylation
	7.5 Introduction to E2 Reactions
	7.6 Stability of Alkenes and Cycloalkenes
	7.7 Regiochemical and Stereochemical Outcomes for E2 Reactions
	7.8 Unimolecular Reactions (SN1 and E1
	7.9 Predicting Products: Substitution vs. Elimination
	7.10 Substitution and Elimination Reactions with Other Substrates
	7.11 Synthesis Strategies
		BioLinks Radiolabeled Compounds in Diagnostic Medicine
	7.12 Solvent Effects in Substitution Reactions
		SpecialTopic Kinetic Isotope Effects
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 8: Addition Reactions of Alkenes
	8.1 Introduction to Addition Reactions
	8.2 Alkenes in Nature and in Industry
		WorldLinks Pheromones to Control Insect Populations
	8.3 Nomenclature of Alkenes
	8.4 Addition vs. Elimination: A Thermodynamic Perspective
	8.5 Hydrohalogenation
		WorldLinks Cationic Polymerization and Polystyrene
	8.6 Acid-Catalyzed Hydration
	8.7 Oxymercuration-Demercuration
	8.8 Hydroboration-Oxidation
	8.9 Catalytic Hydrogenation
		WorldLinks Partially Hydrogenated Fats and Oils
	8.10 Halogenation and Halohydrin Formation
	8.11 Anti Dihydroxylation
	8.12 Syn Dihydroxylation
	8.13 Oxidative Cleavage
	8.14 Predicting the Products of an Addition Reaction
	8.15 Synthesis Strategies
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS-STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 9: Alkynes
	9.1 Introduction to Alkynes
		BioLinks The Role of Molecular Rigidity
		WorldLinks Conducting Organic Polymers
	9.2 Nomenclature of Alkynes
	9.3 Acidity of Acetylene and Terminal Alkynes
	9.4 Preparation of Alkynes
	9.5 Reduction of Alkynes
	9.6 Hydrohalogenation of Alkynes
	9.7 Hydration of Alkynes
	9.8 Halogenation of Alkynes
	9.9 Ozonolysis of Alkynes
	9.10 Alkylation of Terminal Alkynes
	9.11 Synthesis Strategies
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 10: Radical Reactions
	10.1 Radicals
	10.2 Common Patterns in Radical Mechanisms
	10.3 Chlorination of Methane
	10.4 Thermodynamic Considerations for Halogenation Reactions
	10.5 Selectivity of Halogenation
	10.6 Stereochemistry of Halogenation
	10.7 Allylic Bromination
	10.8 Atmospheric Chemistry and the Ozone Layer
		WorldLinks Fighting Fires with Chemicals
	10.9 Autooxidation and Antioxidants
		BioLinks Why Is an Overdose of Acetaminophen Fatal
	10.10 Radical Addition of HBr: Anti-Markovnikov Addition
	10.11 Radical Polymerization
	10.12 Radical Processes in the Petrochemical Industry
	10.13 Halogenation as a Synthetic Technique
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 11: Synthesis
	11.1 One-Step Syntheses
	11.2 Functional Group Transformations
	11.3 Reactions That Change the Carbon Skeleton
		BioLinks Vitamins
	11.4 How to Approach a Synthesis Problem
		BioLinks The Total Synthesis of Vitamin B12
	11.5 Multi-step Synthesis and Retrosynthetic Analysis
		WorldLinks Retrosynthetic Analysis
	11.6 Green Chemistry
	11.7 Practical Tips for Increasing Proficiency
		BioLinks Total Synthesis of Taxol
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 12: Alcohols and Phenols
	12.1 Structure and Properties of Alcohols
		BioLinks Chain Length as a Factor in Drug Design
	12.2 Acidity of Alcohols and Phenols
	12.3 Preparation of Alcohols via Substitution or Addition
	12.4 Preparation of Alcohols via Reduction
	12.5 Preparation of Diols
		WorldLinks Antifreeze
	12.6 Preparation of Alcohols via Grignard Reagents
	12.7 Protection of Alcohols
	12.8 Preparation of Phenols
	12.9 Reactions of Alcohols: Substitution and Elimination
		BioLinks Drug Metabolism
	12.10 Reactions of Alcohols: Oxidation
	12.11 Biological Redox Reactions
		BioLinks Biological Oxidation of Methanol and Ethanol
	12.12 Oxidation of Phenol
	12.13 Synthesis Strategies
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 13: Ethers and Epoxides; Thiols and Sulfides
	13.1 Introduction to Ethers
	13.2 Nomenclature of Ethers
	13.3 Structure and Properties of Ethers
		BioLinks Ethers as Inhalation Anesthetics
	13.4 Crown Ethers
		WorldLinks Chelating Agents in the Food Industry and in Medicine
	13.5 Preparation of Ethers
	13.6 Reactions of Ethers
	13.7 Nomenclature of Epoxides
		BioLinks Epothilones as Novel Anticancer Agents
	13.8 Preparation of Epoxides
		BioLinks Active Metabolites and Drug Interactions
	13.9 Enantioselective Epoxidation
	13.10 Ring-Opening Reactions of Epoxides
		WorldLinks Ethylene Oxide as a Sterilizing Agent for Sensitive Medical Equipment
		BioLinks Cigarette Smoke and Carcinogenic Epoxides
	13.11 Thiols and Sulfides
	13.12 Synthesis Strategies Involving Epoxides
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 14: Infrared Spectroscopy and Mass Spectrometry
	14.1 Introduction to Spectroscopy
		WorldLinks Microwave Ovens
	14.2 IR Spectroscopy
		BioLinks IR Thermal Imaging for Cancer Detection
	14.3 Signal Characteristics: Wavenumber
	14.4 Signal Characteristics: Intensity
		WorldLinks IR Spectroscopy for Testing Blood Alcohol Levels
	14.5 Signal Characteristics: Shape
	14.6 Analyzing an IR Spectrum
	14.7 Using IR Spectroscopy to Distinguish between Two Compounds
	14.8 Introduction to Mass Spectrometry
		WorldLinks Mass Spectrometry for Detecting Explosives
	14.9 Analyzing the (M)+• Peak
	14.10 Analyzing the (M+1)+• Peak
	14.11 Analyzing the (M+2)+• Peak
	14.12 Analyzing the Fragments
	14.13 High-Resolution Mass Spectrometry
	14.14 Gas Chromatography–Mass Spectrometry
	14.15 Mass Spectrometry of Large Biomolecules
		BioLinks Medical Applications of Mass Spectrometry
	14.16 Hydrogen Deficiency Index: Degrees of Unsaturation
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 15: Nuclear Magnetic Resonance Spectroscopy
	15.1 Introduction to NMR Spectroscopy
	15.2 Acquiring a 1H NMR Spectrum
	15.3 Characteristics of a 1H NMR Spectrum
	15.4 Number of Signals
	15.5 Chemical Shift
	15.6 Integration
	15.7 Multiplicity
	15.8 Drawing the Expected 1H NMR Spectrum of a Compound
	15.9 Using 1H NMR Spectroscopy to Distinguish between Compounds
		BioLinks Detection of Impurities in Heparin Sodium Using 1H NMR Spectroscopy
	15.10 Analyzing a 1H NMR Spectrum
	15.11 Acquiring a 13C NMR Spectrum
	15.12 Chemical Shifts in 13C NMR Spectroscopy
	15.13 DEPT 13C NMR Spectroscopy
		BioLinks Magnetic Resonance Imaging (MRI)
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 16: Conjugated Pi Systems and Pericyclic Reactions
	16.1 Classes of Dienes
	16.2 Conjugated Dienes
	16.3 Molecular Orbital Theory
	16.4 Electrophilic Addition
	16.5 Thermodynamic Control vs. Kinetic Control
		WorldLinks Natural and Synthetic Rubbers
	16.6 An Introduction to Pericyclic Reactions
	16.7 Diels–Alder Reactions
	16.8 MO Description of Cycloadditions
	16.9 Electrocyclic Reactions
	16.10 Sigmatropic Rearrangements
		BioLinks The Photoinduced Biosynthesis of Vitamin D
	16.11 UV-Vis Spectroscopy
		WorldLinks Sunscreens
	16.12 Color
		WorldLinks Bleach
	16.13 Chemistry of Vision
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 17: Aromatic Compounds
	17.1 Introduction to Aromatic Compounds
		WorldLinks What Is Coal
	17.2 Nomenclature of Benzene Derivatives
	17.3 Structure of Benzene
	17.4 Stability of Benzene
		WorldLinks Molecular Cages
	17.5 Aromatic Compounds Other Than Benzene
		BioLinks The Development of Nonsedating
 Antihistamines
	17.6 Reactions at the Benzylic Position
	17.7 Reduction of Benzene and Its Derivatives
	17.8 Spectroscopy of Aromatic Compounds
		WorldLinks Buckyballs and Nanotubes
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 18: Aromatic Substitution Reactions
	18.1 Introduction to Electrophilic Aromatic Substitution
	18.2 Halogenation
		BioLinks Halogenation in Drug Design
	18.3 Sulfonation
		WorldLinks What Are Those Colors in Fruity Pebbles
	18.4 Nitration
		BioLinks The Discovery of
 Prodrugs
	18.5 Friedel–Crafts Alkylation
	18.6 Friedel–Crafts Acylation
	18.7 Activating Groups
	18.8 Deactivating Groups
	18.9 Halogens: The Exception
	18.10 Determining the Directing Effects of a Substituent
	18.11 Multiple Substituents
	18.12 Synthesis Strategies
	18.13 Nucleophilic Aromatic Substitution
	18.14 Elimination-Addition
	18.15 Identifying the Mechanism of an Aromatic Substitution Reaction
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 19: Aldehydes and Ketones
	19.1 Introduction to Aldehydes and Ketones
	19.2 Nomenclature
	19.3 Preparing Aldehydes and Ketones: A Review
	19.4 Introduction to Nucleophilic Addition Reactions
	19.5 Oxygen Nucleophiles
		BioLinks Acetals as Prodrugs
	19.6 Nitrogen Nucleophiles
		WorldLinks Beta-Carotene and
 Vision
	19.7 Hydrolysis of Acetals, Imines, and Enamines
		BioLinks Prodrugs
	19.8 Sulfur Nucleophiles
	19.9 Hydrogen Nucleophiles
	19.10 Carbon Nucleophiles
		WorldLinks Organic Cyanide Compounds in Nature
	19.11 Baeyer–Villiger Oxidation of Aldehydes and Ketones
	19.12 Synthesis Strategies
	19.13 Spectroscopic Analysis of Aldehydes and Ketones
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 20: Carboxylic Acids and Their Derivatives
	20.1 Introduction to Carboxylic Acids
	20.2 Nomenclature of Carboxylic Acids
	20.3 Structure and Properties of Carboxylic Acids
	20.4 Preparation of Carboxylic Acids
	20.5 Reactions of Carboxylic Acids
	20.6 Introduction to Carboxylic Acid Derivatives
		BioLinks Sedatives
	20.7 Reactivity of Carboxylic Acid Derivatives
	20.8 Preparation and Reactions of Acid Chlorides
	20.9 Preparation and Reactions of Acid Anhydrides
		BioLinks How Does Aspirin Work
	20.10 Preparation of Esters
	20.11 Reactions of Esters
		WorldLinks How Soap Is Made
		BioLinks Esters as Prodrugs
	20.12 Preparation and Reactions of Amides
		WorldLinks Polyesters and Polyamides
		BioLinks Beta-Lactam Antibiotics
	20.13 Preparation and Reactions of Nitriles
	20.14 Synthesis Strategies
	20.15 Spectroscopy of Carboxylic Acids and Their Derivatives
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 21: Alpha Carbon Chemistry: Enols and Enolates
	21.1 Introduction to Alpha Carbon Chemistry: Enols and Enolates
	21.2 Alpha Halogenation of Enols and Enolates
	21.3 Aldol Reactions
		WorldLinks Muscle Power
	21.4 Claisen Condensations
	21.5 Alkylation of the Alpha Position
	21.6 Conjugate Addition Reactions
		BioLinks Glutathione Conjugation and Biological Michael Reactions
	21.7 Synthesis Strategies
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 22: Amines
	22.1 Introduction to Amines
		BioLinks Drug Metabolism Studies
	22.2 Nomenclature of Amines
	22.3 Properties of Amines
		BioLinks Fortunate Side Effects
		WorldLinks Chemical Warfare Among Ants
	22.4 Preparation of Amines: A Review
	22.5 Preparation of Amines via Substitution Reactions
	22.6 Preparation of Amines via Reductive Amination
	22.7 Synthesis Strategies
	22.8 Acylation of Amines
	22.9 Hofmann Elimination
	22.10 Reactions of Amines with Nitrous Acid
	22.11 Reactions of Aryl Diazonium Ions
	22.12 Nitrogen Heterocycles
		BioLinks H2-Receptor Antagonists
 and the Development of Cimetidine
	22.13 Spectroscopy of Amines
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 23: Introduction to Organometallic Compounds
	23.1 General Properties of Organometallic Compounds
	23.2 Organolithium and Organomagnesium Compounds
	23.3 Lithium Dialkyl Cuprates (Gilman Reagents)
	23.4 The Simmons–Smith Reaction and Carbenoids
	23.5 Stille Coupling
	23.6 Suzuki Coupling
	23.7 Negishi Coupling
	23.8 The Heck Reaction
	23.9 Alkene Metathesis
		WorldLinks Improving Biodiesel via Alkene Metathesis
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 24: Carbohydrates
	24.1 Introduction to Carbohydrates
	24.2 Classification of Monosaccharides
	24.3 Configuration of Aldoses
	24.4 Configuration of Ketoses
	24.5 Cyclic Structures of Monosaccharides
	24.6 Reactions of Monosaccharides
	24.7 Disaccharides
		BioLinks Lactose Intolerance
		WorldLinks Artificial Sweeteners
	24.8 Polysaccharides
	24.9 Amino Sugars
	24.10 N-Glycosides
		BioLinks Aminoglycoside Antibiotics
		BioLinks Erythromycin Biosynthesis
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 25: Amino Acids, Peptides, and Proteins
	25.1 Introduction to Amino Acids, Peptides, and Proteins
	25.2 Structure and Properties of Amino
 Acids
		WorldLinks Nutrition and Sources of Amino Acids
		WorldLinks Forensic Chemistry and Fingerprint Detection
	25.3 Amino Acid Synthesis
	25.4 Structure of Peptides
		BioLinks Polypeptide Antibiotics
	25.5 Sequencing a Peptide
	25.6 Peptide Synthesis
	25.7 Protein Structure
		BioLinks Diseases Caused by Misfolded Proteins
	25.8 Protein Function
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 26: Lipids
	26.1 Introduction to Lipids
	26.2 Waxes
	26.3 Triglycerides
	26.4 Reactions of Triglycerides
		WorldLinks Soaps Versus Synthetic Detergents
	26.5 Phospholipids
		BioLinks Polyether Antibiotics
	26.6 Steroids
		BioLinks Cholesterol and Heart Disease
		BioLinks Anabolic Steroids and Competitive Sports
	26.7 Prostaglandins
		BioLinks NSAIDs and COX-2 Inhibitors
	26.8 Terpenes
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS- STYLE PROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Chapter 27: Synthetic Polymers
	27.1 Introduction to Synthetic Polymers
	27.2 Nomenclature of Synthetic Polymers
	27.3 Copolymers
	27.4 Polymer Classification by Reaction Type
	27.5 Polymer Classification by Mode of
 Assembly
	27.6 Polymer Classification by Structure
	27.7 Polymer Classification by Properties
		WorldLinks Safety Glass and Car Windshields
	27.8 Polymer Recycling
	REVIEW OF REACTIONS
	REVIEW OF CONCEPTS AND VOCABULARY
	SKILLBUILDER REVIEW
	PRACTICE PROBLEMS
	ACS-STYLEPROBLEMS (Multiple Choice)
	INTEGRATED PROBLEMS
	CHALLENGE PROBLEMS
Appendix
Appendix: Nomenclature of Polyfunctional Compounds
Selected Answers
Glossary
Index
EULA