Organic Chemistry: Structure and Function 8th Edition PDF by Peter Vollhardt and Neil Schore

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Organic Chemistry: Structure and Function, Eighth Edition

By Peter Vollhardt and Neil Schore

Organic Chemistry: Structure and Function, Eighth Edition

Contents:

PREFACE: A User’s Guide to ORGANIC CHEMISTRY: Structure and Function

1 STRUCTURE AND BONDING IN ORGANIC MOLECULES

1-1 The Scope of Organic Chemistry: An Overview

Real Life: Nature 1-1 Urea: From Urine to Wöhler’s Synthesis to Industrial Fertilizer

1-2 Coulomb Forces: A Simplified View of Bonding

1-3 Ionic and Covalent Bonds: The Octet Rule

1-4 Electron-Dot Model of Bonding: Lewis Structures

1-5 Resonance Forms

1-6 Atomic Orbitals: A Quantum Mechanical Description of Electrons Around the Nucleus

1-7 Molecular Orbitals and Covalent Bonding

1-8 Hybrid Orbitals: Bonding in Complex Molecules

1-9 Structures and Formulas of Organic Molecules

1-10 A General Strategy for Solving Problems in Organic Chemistry Worked Examples: Integrating the Concepts

Important Concepts

Problems

2 STRUCTURE AND REACTIVITY

Acids and Bases, Polar and Nonpolar Molecules

2-1 Kinetics and Thermodynamics of Simple Chemical Processes

2-2 Keys to Success: Using Curved “Electron-Pushing” Arrows to Describe Chemical Reactions

2-3 Acids and Bases

Real Life: Medicine 2-1 Stomach Acid, Peptic Ulcers,

Pharmacology, and Organic Chemistry

2-4 Functional Groups: Centers of Reactivity

2-5 Straight-Chain and Branched Alkanes

2-6 Naming the Alkanes

2-7 Structural and Physical Properties of Alkanes

Real Life: Nature 2-2 “Sexual Swindle” by Means of Chemical Mimicry

2-8 Rotation about Single Bonds: Conformations

2-9 Rotation in Substituted Ethanes

2-10 Worked Examples: Integrating the Concepts

Important Concepts

Problems

3 REACTIONS OF ALKANES

Bond-Dissociation Energies, Radical Halogenation, and Relative Reactivity

3-1 Strength of Alkane Bonds: Radicals

3-2 Structure of Alkyl Radicals: Hyperconjugation

3-3 Conversion of Petroleum: Pyrolysis

Real Life: Sustainability 3-1 Sustainability and the Needs of the 21st Century: “Green” Chemistry

3-4 Chlorination of Methane: The Radical Chain Mechanism

3-5 Other Radical Halogenations of Methane

3-6 Keys to Success: Using the “Known” Mechanism as a Model for the “Unknown”

3-7 Chlorination of Higher Alkanes: Relative Reactivity and Selectivity

3-8 Selectivity in Radical Halogenation with Fluorine and Bromine

3-9 Synthetic Radical Halogenation

Real Life: Medicine 3-2 Chlorination, Chloral, and DDT: The Quest to Eradicate Malaria

3-10 Synthetic Chlorine Compounds and the Stratospheric Ozone Layer

3-11 Combustion and the Relative Stabilities of Alkanes

3-12 Worked Examples: Integrating the Concepts

Important Concepts

Problems

4 CYCLOALKANES

4-1 Names and Physical Properties of Cycloalkanes

4-2 Ring Strain and the Structure of Cycloalkanes

4-3 Cyclohexane: A Strain-Free Cycloalkane

4-4 Substituted Cyclohexanes

4-5 Larger Cycloalkanes

4-6 Polycyclic Alkanes

4-7 Carbocyclic Products in Nature

Real Life: Materials 4-1 Cyclohexane, Adamantane, and Diamandoids: Diamond “Molecules”

Real Life: Medicine 4-2 Cholesterol: How Is It Bad and How Bad Is It?

Real Life: Medicine 4-3 Controlling Fertility: From “the Pill” to

RU-486 to Male Contraceptives

4-8 Worked Examples: Integrating the Concepts

Important Concepts

Problems

5 STEREOISOMERS

5-1 Chiral Molecules

Real Life: Nature 5-1 Chiral Substances in Nature

5-2 Optical Activity

5-3 Absolute Configuration: R,S Sequence Rules

5-4 Fischer Projections

5-5 Molecules Incorporating Several Stereocenters: Diastereomers

Real Life: Nature 5-2 Stereoisomers of Tartaric Acid

5-6 Meso Compounds

5-7 Stereochemistry in Chemical Reactions

Real Life: Medicine 5-3 Chiral Drugs—Racemic or Enantiomerically Pure?

Real Life: Medicine 5-4 Why Is Nature “Handed”?

5-8 Resolution: Separation of Enantiomers

5-9 Worked Examples: Integrating the Concepts

Important Concepts

Problems

6 PROPERTIES AND REACTIONS OF HALOALKANES

Bimolecular Nucleophilic Substitution

6-1 Physical Properties of Haloalkanes

Real Life: Medicine 6-1 Fluorinated Pharmaceuticals

6-2 Nucleophilic Substitution

6-3 Reaction Mechanisms Involving Polar Functional Groups: Using “Electron-Pushing” Arrows

6-4 A Closer Look at the Nucleophilic Substitution Mechanism: Kinetics

6-5 Frontside or Backside Attack? Stereochemistry of the SN2 Reaction

6-6 Consequences of Inversion in SN2 Reactions

6-7 Structure and SN2 Reactivity: The Leaving Group

6-8 Structure and SN2 Reactivity: The Nucleophile

6-9 Keys to Success: Choosing Among Multiple Mechanistic Pathways

6-10 Structure and SN2 Reactivity: The Substrate

6-11 The SN2 Reaction at a Glance

6-12 Worked Examples: Integrating the Concepts

Important Concepts

Problems

7 FURTHER REACTIONS OF HALOALKANES

Unimolecular Substitution and Pathways of Elimination

7-1 Solvolysis of Tertiary and Secondary Haloalkanes

7-2 Unimolecular Nucleophilic Substitution

7-3 Stereochemical Consequences of SN1 Reactions

7-4 Effects of Solvent, Leaving Group, and Nucleophile on Unimolecular Substitution

7-5 Effect of the Alkyl Group on the SN1 Reaction: Carbocation Stability

Real Life: Medicine 7-1 Unusually Stereoselective SN1 Displacement in Anticancer Drug Synthesis

7-6 Unimolecular Elimination: E1

7-7 Bimolecular Elimination: E2

7-8 Keys to Success: Substitution versus Elimination—Structure Determines Function

7-9 Summary of Reactivity of Haloalkanes

7-10 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

8 HYDROXY FUNCTIONAL GROUP: ALCOHOLS

Properties, Preparation, and Strategy of Synthesis

8-1 Naming the Alcohols

8-2 Structural and Physical Properties of Alcohols

8-3 Alcohols as Acids and Bases

8-4 Synthesis of Alcohols by Nucleophilic Substitution

8-5 Synthesis of Alcohols: Oxidation–Reduction Relation Between Alcohols and Carbonyl Compounds

Real Life: Medicine 8-1 Oxidation and Reduction in the Body

Real Life: Medicine 8-2 Don’t Drink and Drive: The Breath Analyzer Test

8-6 Organometallic Reagents: Sources of Nucleophilic Carbon for Alcohol Synthesis

8-7 Organometallic Reagents in the Synthesis of Alcohols

8-8 Keys to Success: An Introduction to Synthetic Strategy

Real Life: Chemistry 8-3 What Magnesium Does Not Do, Copper Can: Alkylation of Organometallics

8-9 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

9 FURTHER REACTIONS OF ALCOHOLS AND THE CHEMISTRY OF ETHERS

9-1 Reactions of Alcohols with Base: Preparation of Alkoxides

9-2 Reactions of Alcohols with Strong Acids: Alkyloxonium Ions in Substitution and Elimination Reactions of Alcohols

9-3 Carbocation Rearrangements

9-4 Esters from Alcohols and Haloalkane Synthesis

9-5 Names and Physical Properties of Ethers

9-6 Williamson Ether Synthesis

Real Life: Nature 9-1 Chemiluminescence of 1,2- Dioxacyclobutanes

9-7 Synthesis of Ethers: Alcohols and Mineral Acids

9-8 Reactions of Ethers

Real Life: Medicine 9-2 Protecting Groups in the Synthesis of Testosterone

9-9 Reactions of Oxacyclopropanes

Real Life: Chemistry 9-3 Hydrolytic Kinetic Resolution of

Oxacyclopropanes

9-10 Sulfur Analogs of Alcohols and Ethers

9-11 Physiological Properties and Uses of Alcohols and Ethers

9-12 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

10 USING NUCLEAR MAGNETIC RESONANCE

SPECTROSCOPY TO DEDUCE STRUCTURE

10-1 Physical and Chemical Tests

10-2 Defining Spectroscopy

10-3 Hydrogen Nuclear Magnetic Resonance

Real Life: Spectroscopy 10-1 Recording an NMR Spectrum

10-4 Using NMR Spectra to Analyze Molecular Structure: The

Proton Chemical Shift

10-5 Tests for Chemical Equivalence

Real Life: Medicine 10-2 Magnetic Resonance Imaging (MRI)

in Medicine

10-6 Integration of NMR Signals

10-7 Spin–Spin Splitting: The Effect of Nonequivalent Neighboring

Hydrogens

10-8 Spin–Spin Splitting: Some Complications

Real Life: Spectroscopy 10-3 The Nonequivalence of

Diastereotopic Hydrogens

10-9 Carbon-13 Nuclear Magnetic Resonance

Real Life: Spectroscopy 10-4 How to Determine Atom

Connectivity in NMR

Real Life: Medicine 10-5 Structural Characterization of Natural

and “Unnatural” Products: An Antioxidant from Grape Seeds

and a Fake Drug in Herbal Medicines

10-10 Worked Examples: Integrating the Concepts

Important Concepts

Problems

11 ALKENES: INFRARED SPECTROSCOPY

AND MASS SPECTROMETRY

11-1 Naming the Alkenes

11-2 Structure and Bonding in Ethene: The Pi Bond

11-3 Physical Properties of Alkenes

11-4 Nuclear Magnetic Resonance of Alkenes

Real Life: Medicine 11-1 NMR of Complex Molecules: The Powerfully Regulating Prostaglandins

11-5 Catalytic Hydrogenation of Alkenes: Relative Stability of Double Bonds

11-6 Preparation of Alkenes from Haloalkanes and Alkyl Sulfonates: Bimolecular Elimination Revisited

11-7 Preparation of Alkenes by Dehydration of Alcohols

11-8 Infrared Spectroscopy

11-9 Measuring the Molecular Mass of Organic Compounds: Mass Spectrometry

Real Life: Medicine 11-2 Detecting Performance-Enhancing

Drugs Using Mass Spectrometry

11-10 Fragmentation Patterns of Organic Molecules

11-11 Degree of Unsaturation: Another Aid to Identifying Molecular Structure

11-12 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

12 REACTIONS OF ALKENES

12-1 Why Addition Reactions Proceed: Thermodynamic Feasibility

12-2 Catalytic Hydrogenation

12-3 Basic and Nucleophilic Character of the Pi Bond: Electrophilic Addition of Hydrogen Halides

12-4 Alcohol Synthesis by Electrophilic Hydration: Thermodynamic Control

12-5 Electrophilic Addition of Halogens to Alkenes

12-6 The Generality of Electrophilic Addition

12-7 Oxymercuration–Demercuration: A Special Electrophilic Addition

Real Life: Medicine 12-1 Juvenile Hormone Analogs in the Battle Against Insect-Borne Diseases

12-8 Hydroboration–Oxidation: A Stereospecific Anti-Markovnikov Hydration

12-9 Diazomethane, Carbenes, and Cyclopropane Synthesis

12-10 Oxacyclopropane (Epoxide) Synthesis: Epoxidation by Peroxycarboxylic Acids

12-11 Vicinal Syn Dihydroxylation with Osmium Tetroxide

Real Life: Medicine 12-2 Synthesis of Antitumor Drugs:

Sharpless Enantioselective Oxacyclopropanation (Epoxidation) and Dihydroxylation

12-12 Oxidative Cleavage: Ozonolysis

12-13 Radical Additions: Anti-Markovnikov Product Formation

12-14 Dimerization, Oligomerization, and Polymerization of Alkenes

12-15 Synthesis of Polymers

12-16 Ethene: An Important Industrial Feedstock

12-17 Alkenes in Nature: Insect Pheromones

Real Life: Medicine 12-3 Alkene Metathesis Transposes the

Termini of Two Alkenes: Construction of Rings

12-18 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

13 ALKYNES

The Carbon–Carbon Triple Bond

13-1 Naming the Alkynes

13-2 Properties and Bonding in the Alkynes

13-3 Spectroscopy of the Alkynes

13-4 Preparation of Alkynes by Double Elimination

13-5 Preparation of Alkynes from Alkynyl Anions

13-6 Reduction of Alkynes: The Relative Reactivity of the Two Pi Bonds

13-7 Electrophilic Addition Reactions of Alkynes

13-8 Anti-Markovnikov Additions to Triple Bonds

13-9 Chemistry of Alkenyl Halides

Real Life: Synthesis 13-1 Metal-Catalyzed Stille, Suzuki, and Sonogashira Coupling Reactions

13-10 Ethyne as an Industrial Starting Material

13-11 Alkynes in Nature and in Medicine

13-12 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

14 DELOCALIZED Pi SYSTEMS

Investigation by Ultraviolet and Visible Spectroscopy

14-1 Overlap of Three Adjacent p Orbitals: Electron Delocalization in the 2-Propenyl (Allyl) System

14-2 Radical Allylic Halogenation

14-3 Nucleophilic Substitution of Allylic Halides: SN1 and SN2

14-4 Allylic Organometallic Reagents: Useful Three-Carbon Nucleophiles

14-5 Two Neighboring Double Bonds: Conjugated Dienes

14-6 Electrophilic Attack on Conjugated Dienes: Kinetic and Thermodynamic Control

14-7 Delocalization Among More than Two Pi Bonds: Extended Conjugation and Benzene

14-8 A Special Transformation of Conjugated Dienes: Diels-Alder Cycloaddition

Real Life: Materials 14-1 Organic Polyenes Conduct Electricity

Real Life: Sustainability 14-2 The Diels-Alder Reaction is “Green”

14-9 Electrocyclic Reactions

14-10 Polymerization of Conjugated Dienes: Rubber

14-11 Electronic Spectra: Ultraviolet and Visible Spectroscopy

Real Life: Spectroscopy 14-3 The Contributions of IR, MS, and UV to the Characterization of Viniferone

14-12 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

INTERLUDE

A Summary of Organic Reaction Mechanisms

15 BENZENE AND AROMATICITY

Electrophilic Aromatic Substitution

15-1 Naming the Benzenes

15-2 Structure and Resonance Energy of Benzene: A First Look at Aromaticity

15-3 Pi Molecular Orbitals of Benzene

15-4 Spectral Characteristics of the Benzene Ring

Real Life: Materials 15-1 Compounds Made of Pure Carbon:

Graphite, Graphene, Diamond, and Fullerenes

15-5 Polycyclic Aromatic Hydrocarbons

15-6 Other Cyclic Polyenes: Hückel’s Rule

15-7 Hückel’s Rule and Charged Molecules

15-8 Synthesis of Benzene Derivatives: Electrophilic Aromatic Substitution

15-9 Halogenation of Benzene: The Need for a Catalyst

15-10 Nitration and Sulfonation of Benzene

15-11 Friedel-Crafts Alkylation

15-12 Limitations of Friedel-Crafts Alkylations

15-13 Friedel-Crafts Acylation

15-14 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

16 ELECTROPHILIC ATTACK ON DERIVATIVES OF BENZENE

Substituents Control Regioselectivity

16-1 Activation or Deactivation by Substituents on a Benzene Ring

16-2 Directing Electron-Donating Effects of Alkyl Groups

16-3 Directing Effects of Substituents in Conjugation with the Benzene Ring

Real Life: Materials 16-1 Explosive Nitroarenes: TNT and Picric Acid

16-4 Electrophilic Attack on Disubstituted Benzenes

16-5 Keys to Success: Synthetic Strategies Toward Substituted Benzenes

16-6 Reactivity of Polycyclic Benzenoid Hydrocarbons

16-7 Polycyclic Aromatic Hydrocarbons and Cancer

16-8 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

17 ALDEHYDES AND KETONES

The Carbonyl Group

17-1 Naming the Aldehydes and Ketones

17-2 Structure of the Carbonyl Group

17-3 Spectroscopic Properties of Aldehydes and Ketones

17-4 Preparation of Aldehydes and Ketones

17-5 Reactivity of the Carbonyl Group: Mechanisms of Addition

17-6 Addition of Water to Form Hydrates

17-7 Addition of Alcohols to Form Hemiacetals and Acetals

17-8 Acetals as Protecting Groups

17-9 Nucleophilic Addition of Ammonia and Its Derivatives

Real Life: Biochemistry 17-1 Imines Mediate the Biochemistry of Amino Acids

17-10 Deoxygenation of the Carbonyl Group

17-11 Addition of Hydrogen Cyanide to Give Cyanohydrins

17-12 Addition of Phosphorus Ylides: The Wittig Reaction

17-13 Oxidation by Peroxycarboxylic Acids: The Baeyer-Villiger Oxidation

17-14 Oxidative Chemical Tests for Aldehydes

17-15 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

18 ENOLS, ENOLATES, AND THE ALDOL CONDENSATION

α,β -Unsaturated Aldehydes and Ketones

18-1 Acidity of Aldehydes and Ketones: Enolate Ions

18-2 Keto–Enol Equilibria

18-3 Halogenation of Aldehydes and Ketones

18-4 Alkylation of Aldehydes and Ketones

18-5 Attack by Enolates on the Carbonyl Function: Aldol Condensation

Real Life: Biology And Medicine 18-1 Stereoselective Aldol

Reactions in Nature and in the Laboratory: “Organocatalysis”

18-6 Crossed Aldol Condensation

18-7 Keys to Success: Competitive Reaction Pathways and the Intramolecular Aldol Condensation

Real Life: Nature 18-2 Absorption of Photons by Unsaturated Aldehydes Enables Vision

18-8 Properties of α,β -Unsaturated Aldehydes and Ketones

18-9 Conjugate Additions to α,β -Unsaturated Aldehydes and Ketones

18-10 1,2- and 1,4-Additions of Organometallic Reagents

18-11 Conjugate Additions of Enolate Ions: Michael Addition and Robinson Annulation

18-12 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

19 CARBOXYLIC ACIDS

19-1 Naming the Carboxylic Acids

19-2 Structural and Physical Properties of Carboxylic Acids

19-3 Spectroscopy and Mass Spectrometry of Carboxylic Acids

19-4 Acidic and Basic Character of Carboxylic Acids

19-5 Carboxylic Acid Synthesis in Industry

19-6 Methods for Introducing the Carboxy Functional Group

19-7 Substitution at the Carboxy Carbon: The Addition–Elimination Mechanism

19-8 Carboxylic Acid Derivatives: Acyl Halides and Anhydrides

19-9 Carboxylic Acid Derivatives: Esters

19-10 Carboxylic Acid Derivatives: Amides

19-11 Reduction of Carboxylic Acids by Lithium Aluminum Hydride

19-12 Bromination Next to the Carboxy Group: The Hell-Volhard- Zelinsky Reaction

19-13 Biological Activity of Carboxylic Acids

Real Life: Materials 19-1 Long-Chain Carboxylates and

Sulfonates Make Soaps and Detergents

Real Life: Health 19-2 Artery-Clogging Trans Fatty Acids Phasing Out

Real Life: Materials 19-3 Green Plastics, Fibers, and Energy

from Biomass-Derived Hydroxyesters

19-14 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

20 CARBOXYLIC ACID DERIVATIVES

20-1 Relative Reactivities, Structures, and Spectra of Carboxylic

Acid Derivatives

20-2 Chemistry of Acyl Halides

20-3 Chemistry of Carboxylic Anhydrides

20-4 Chemistry of Esters

20-5 Esters in Nature: Waxes, Fats, Oils, and Lipids

Real Life: Sustainability 20-1 Moving Away from Petroleum:

Green Fuels from Vegetable Oil

20-6 Amides: The Least Reactive Carboxylic Acid Derivatives

Real Life: Medicine 20-2 Killing the Bugs that Kill the Drugs:

Antibiotic Wars

20-7 Amidates and Their Halogenation: The Hofmann

Rearrangement

20-8 Alkanenitriles: A Special Class of Carboxylic Acid Derivatives

20-9 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

21 AMINES AND THEIR DERIVATIVES

Functional Groups Containing Nitrogen

21-1 Naming the Amines

Real Life: Medicine 21-1 Physiologically Active Amines and

Weight Control

21-2 Structural and Physical Properties of Amines

21-3 Spectroscopy of the Amine Group

21-4 Acidity and Basicity of Amines

21-5 Synthesis of Amines by Alkylation

21-6 Synthesis of Amines by Reductive Amination

21-7 Synthesis of Amines from Carboxylic Amides

21-8 Reactions of Quaternary Ammonium Salts: Hofmann

Elimination

21-9 Mannich Reaction: Alkylation of Enols by Iminium Ions

21-10 Nitrosation of Amines

Real Life: Medicine 21-2 Sodium Nitrite as a Food Additive,

N-Nitrosodialkanamines, and Cancer

Real Life: Materials 21-3 Amines in Industry: Nylon, the

“Miracle Fiber”

21-11 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

22 CHEMISTRY OF BENZENE SUBSTITUENTS

Alkylbenzenes, Phenols, and Anilines

22-1 Reactivity at the Phenylmethyl (Benzyl) Carbon: Benzylic

Resonance Stabilization

22-2 Oxidations and Reductions of Substituted Benzenes

22-3 Names and Properties of Phenols

Real Life: Medicine 22-1 Two Phenols in the News: Bisphenol

A and Resveratrol

22-4 Preparation of Phenols: Nucleophilic Aromatic Substitution

22-5 Alcohol Chemistry of Phenols

Real Life: Medicine 22-2 Aspirin: The Miracle Drug

22-6 Electrophilic Substitution of Phenols

22-7 An Electrocyclic Reaction of the Benzene Ring: The Claisen Rearrangement

22-8 Oxidation of Phenols: Benzoquinones

Real Life: Biology 22-3 Chemical Warfare in Nature: The Bombardier Beetle

22-9 Oxidation-Reduction Processes in Nature

22-10 Arenediazonium Salts

22-11 Electrophilic Substitution with Arenediazonium Salts: Diazo Coupling

22-12 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

23 ESTER ENOLATES AND THE CLAISEN CONDENSATION

Synthesis of β-Dicarbonyl Compounds; Acyl Anion Equivalents

23-1 β -Dicarbonyl Compounds: Claisen Condensations

Real Life: Nature 23-1 Claisen Condensations Assemble Biological Molecules

23-2 β -Dicarbonyl Compounds as Synthetic Intermediates

23-3 β -Dicarbonyl Anion Chemistry: Michael Additions

23-4 Acyl Anion Equivalents: Preparation of α -Hydroxyketones

Real Life: Nature 23-2 Thiamine: A Natural, Metabolically Active Thiazolium Salt

23-5 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

24 CARBOHYDRATES

Polyfunctional Compounds in Nature

24-1 Names and Structures of Carbohydrates

24-2 Conformations and Cyclic Forms of Sugars

24-3 Anomers of Simple Sugars: Mutarotation of Glucose

24-4 Polyfunctional Chemistry of Sugars: Oxidation to Carboxylic Acids

24-5 Oxidative Cleavage of Sugars

24-6 Reduction of Monosaccharides to Alditols

24-7 Carbonyl Condensations with Amine Derivatives

24-8 Ester and Ether Formation: Glycosides

24-9 Step-by-Step Buildup and Degradation of Sugars

Real Life: Nature 24-1 Biological Sugar Synthesis

24-10 Relative Configurations of the Aldoses: An Exercise in Structure Determination

24-11 Complex Sugars in Nature: Disaccharides

Real Life: Food Chemistry 24-2 Manipulating Our Sweet Tooth

24-12 Polysaccharides and Other Sugars in Nature

Real Life: Medicine 24-3 Sialic Acid, “Bird Flu,” and Rational Drug Design

24-13 Worked Example: Integrating the Concepts

New Reactions

Important Concepts

Problems

25 HETEROCYCLES

Heteroatoms in Cyclic Organic Compounds

25-1 Naming the Heterocycles

25-2 Nonaromatic Heterocycles

Real Life: Medicine 25-1 Smoking, Nicotine, Cancer, and Medicinal Chemistry

25-3 Structures and Properties of Aromatic Heterocyclopentadienes

25-4 Reactions of the Aromatic Heterocyclopentadienes

25-5 Structure and Preparation of Pyridine: An Azabenzene

25-6 Reactions of Pyridine

Real Life: Biochemistry 25-2 Lessons from Redox-Active

Pyridinium Salts in Nature: Nicotinamide Adenine

Dinucleotide, Dihydropyridines, and Synthesis

25-7 Quinoline and Isoquinoline: The Benzopyridines

Real Life: Biology 25-3 Folic Acid, Vitamin D, Cholesterol, and the Color of Your Skin

25-8 Alkaloids: Physiologically Potent Nitrogen Heterocycles in Nature

Real Life: Nature 25-4 Nature is Not Always Green: Natural Pesticides

25-9 Worked Examples: Integrating the Concepts

New Reactions

Important Concepts

Problems

26 AMINO ACIDS, PEPTIDES, PROTEINS, AND NUCLEIC ACIDS

Nitrogen-Containing Polymers in Nature

26-1 Structure and Properties of Amino Acids

Real Life: Medicine 26-1 Arginine and Nitric Oxide in Biochemistry and Medicine

26-2 Synthesis of Amino Acids: A Combination of Amine and Carboxylic Acid Chemistry

26-3 Synthesis of Enantiomerically Pure Amino Acids

Real Life: Chemistry 26-2 Enantioselective Synthesis of Optically Pure Amino Acids: Phase-Transfer Catalysis

26-4 Peptides and Proteins: Amino Acid Oligomers and Polymers

26-5 Determination of Primary Structure: Amino Acid Sequencing

26-6 Synthesis of Polypeptides: A Challenge in the Application of Protecting Groups

26-7 Merrifield Solid-Phase Peptide Synthesis

26-8 Polypeptides in Nature: Oxygen Transport by the Proteins Myoglobin and Hemoglobin

26-9 Biosynthesis of Proteins: Nucleic Acids Real Life: Medicine 26-3 Synthetic Nucleic Acid Bases and

Nucleosides in Medicine

26-10 Protein Synthesis Through RNA

26-11 DNA Sequencing and Synthesis: Cornerstones of Gene Technology Real Life: Forensics 26-4 DNA Fingerprinting

26-12 Worked Examples: Integrating the Concepts New Reactions

Important Concepts

Problems

Answers to Exercises

Index

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