chapter 1 Carbon Compounds and Chemical Bonds

“We Are Slardust”1（Molecular graphic：Glycine，an organic molecule found in space）

1.1 Introduction

1.2 The Development of Organic Chemistry as a Science

1.3 The Structural Theory of Organic Chemistry

1.4 Chemical Bonds：The Octet Rule

1.5 Writing Lewis Structures

1.6 Exceptions to the Octet Rule

1.7 Formal Charge

1.8 Resonance

1.9 Quantum Mechanics

1.10 Atomic Orbitals

1.11 Molecular Orbitals

1.12 The Structure of Methane and Ethane：sp3 Hybridization

The Chemistry of...Calculated Molecular Models：Electron Density Surfaces

1.13 The Structure of Ethene（Ethylene）：sp2 Hybridization

1.14 The Structure of Ethyne（Acetylene）：sp Hybridization

1.15 A Summary of Important Concepts that Come From Quantum Mechanics

1.16 Molecular Geometry：The Valence Shell Electron Pair Repulsion Model

1.17 Representation of Structural Formulas

Chapter 2 Representative Carbon Compounds：Functional Groups,Intermolecular Forces,and Infrared（IR）Spectroscopy

Structure and Function：Organic Chemistry,Nanotechnology,and Bioengineering（Molecular graphic：A molecular template for bone growth）

2.1 Carbon-Carbon Covalent Bonds

2.2 Hydrocarbons：Representative Alkanes，Alkenes，Alkynes，and Aromatic Compounds

2.3 Polar Covalent Bonds

The Chemistry of... calculated Molecular Models：Maps of Electrostatic Potentlal

2.4 Polar and Nonpolar Molecules

2.5 Functional Groups

2.6 Alkyl Halides or Haloalkanes

2.7 Alcohols

2.8 Ehers

2.9 Amines

2.10 Aldehydes and Ketones

2.11 Carboxylic Acids，Esters，and Amides

2.12 Nitriles

2.13 Summary of Important Families of Organic Compounds

2.14 Physical Properties and Molecular Structure

2.15 Summary of Attractive Electric Forces

The Chemistry of... Organic Templates Engineered to Mimic Bone Growth

2.16 Infrared Spectroscopy：An Instrumental Method for Detecting Functional Groups

Chapter 3 An Introdution to Organic Reactions：ACIds and Bases

Shuttling the Protons（Molecular graphic：Diamox，a drug that prevents altitude sickness）

3.1 Reactions and Their Mechanisms

3.2 Acid-Base Reactions

The Chemistry of...HOMOs and LUMOs in Reactions

3.3 Heterolysis of Bonds to Carbon：Carbocations and Carbanions

3.4 The Use of Curved Arrows in Illustrating Reactions

3.5 The Strength of Acids and Bases：Ka and pKa

3.6 Predicting the Outcome of Acid-Base Reactions

3.7 The Relationship Between Structure and Acidity

3.8 Energy Changes

3.9 The Relationship Between the Equilibrium Constant and the Standard Free-Energy Change， △G°

3.10 The Acidity of Carboxylic Acids

3.11 The Effect of the Solvent on Acidity

3.12 Organic Compounds as Bases

3.13 A Mechanism for an Organic Reaction

The Chemistry of...Carbonic Anhydrase

3.14 Acids and Bases in Nonaqueous Solutions

3.15 Acid-Base Reactions and the Synthesis of Deuterium-and Tritium-Labeled Compounds

Chapter 4 Alkanes：Nomenclature,Conformational Analysis,and an Introduction to Synthesis

To Be Flexible or inflexible-Molecular Structure Makes the Difference（Molecular graphic：A portion of the structure of diamond，an exceptionally rigid molecule）

4.1 Introduction to Alkanes and Cycloalkanes

4.2 Shapes of Alkanes

4.3 IUPAC Nomenclature of Alkanes，Alkyl Halides，and Alcohols

4.4 Nomenclature of Cycloalkanes

4.5 Nomenclature of Alkenes and Cycloalkenes

4.6 Nomenclature of Alkynes

4.7 Physical Properties of Alkanes and Cycloalkanes

4.8 Sigma Bonds and Bond Rotation

4.9 Conformational Analysis of Butane

4.10 The Relative Stabilities of Cycloalkanes：Ring Strain

4.11 The Origin of Ring Strain in Cyclopropane and Cyclobutane：Angle Strain and Torsional Strain

4.12 Conformations of Cyclohexane

The Chemistry of…Nanoscale Motors and Molecular Switches

4.13 Substituted Cyclohexanes：Axial and Equatorial Hydrogen Atoms

4.14 Disubstituted Cycloalkanes：Cis-Trans Isomerism

4.15 Bicyclic and Polycyclic Alkanes

The Chemistry of…Pheromones：Communication by Means of Chemicals

4.16 Chemical Reactions of Alkanes

4.17 Synthesis of Alkanes and Cycloalkanes

4.18 Some General Principles of Structure and Reactivity： A Look toward Synthesis

4.19 An Introduction to Organic Synthesis

The Chemistry of…From the Inorganic to Organic

Chapter 5 Stereochemistry：Chhiral Molecules

The Handedness of Life（Molecular graphic：The mirror-image stereoisomners of alanine，a chiral amino acid）

5.1 The Biological Significance of Chirality

5.2 Isomerism：Constitutional Isomers and Stereoisomers

5.3 Enantiomers and Chiral Molecules

5.4 More about the Biological Importance of Chirality

5.5 Historical Origin of Stereochemist

5.6 Tests for Chirality： Planes of Symmetry

5.7 Nomenclature of Enantiomers：The R，S System

5.8 Properties of Enantiomers：Optical Activity

5.9 The Origin of Optical Activity

5.10 The Synthesis of Chiral Molecules

5.11 Chiral Drugs

The Chemmistry of…Selective Binding of Drug Enantiomers to Left-and Right-Hand Coiled DNA

5.12 Molecules with More than One Stereogenic Center

5.13 Fischer Projection Formulas

5.14 Stereoisomerism of Cyclic Compounds

5.15 Relating Configurations Through Reactions in Which No Bonds to the Stereogenic Carbon Are Broken

5.16 Separation of Enantiomers：Resolution

5.17 Compounds with Stereogenic Centers Other than Carbon

5.18 Chiral Molecules that Do Not Possess a Tetrahedral Atom with Four Different Groups

Chapter 6 Ionic Reactions—Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Breaking Bacterlal Cell Walls with Organic Chemistrry（Molecular graphic：The SN2 transition state resulting from collision of a hydroxide anion with chloromethane）

6.1 Introduction

6.2 Nucleophilic Substitution Reactions

6.3 Nucleophiles

6.4 Leaving Groups

6.5 Kinetics of a Nucleophilic Substitution Reaction：An SN2 Reaction

6.6 A Mechanism for the SN2 Reaction

6.7 Transition State Theory：Free-Energy Diagrams

6.8 The Stereochemistry of SN2 Reactions

6.9 The Reaction of tert-Butyl Chloride with Hydroxide Ion：An SN1 Reaction

6.10 A Mechanism for the SN1 Reaction

6.11 Carbocations

6.12 The Stereochemistry of SN1 Reactions

6.13 Factors Affecting the Rates of SN1 and SN2 Reactions

6.14 Organic Synthesis：Functional Group Transformations Using SN2 Reactions

The Chemistry of…Biological Methylation：A Biological Nucleophilic Substitution Reaction

6.15 Elimination Reactions of Alkyl Halides

6.16 The E2 Reaction

6.17 The E1 Reaction

6.18 Substitution versus Elimination

6.19 Overall Summary

Chapter 7 Alkenes and AHkynesⅠ：Properties and Synthesis.Elimination Reactions of Alkyl Halides

Cell Membrane Fluidity（Molecular graphic：cis-9-Octadecenoic acid，an unsaturated fatty acid incorporated into cell membrane phospholipids）

7.1 Introduction

7.2 The（E）-（Z）System for Designating Alkene Diastereomers

7.3 Relative Stabilities of Alkenes

7.4 Cycloalkenes

7.5 Synthesis of Alkenes via Elimination Reactions

7.6 Dehydrohalogenation of Alkyl Halides

7.7 Acid-Catalyzed Dehydration of Alcohols

7.8 Carbocation Stability and the Occurrence of Molecular Rearrangements

7.9 Synthesis of Alkynes by Elimination Reactions

7.10 The Acidity of Terminal Alkynes

7.11 Replacement of the Acetylenic Hydrogen Atom of Terminal Alkynes

7.12 Hydrogenation of Alkenes

The Chemistry of...Mydrogenation in the Food Industry

7.13 Hydrogenation：The Function of the Catalyst

The Chemistry of…Homogeneous Asymmetric Catalytic Hydrogenation：Examples Involvlng L-DOPA,（S）-Naproxen,and Aspartame

7.14 Hydrogenation of Alkynes

7.15 Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency

Chapter 8 Alkenes and AlkynesⅡ：Addition Reactions

The Sea：A Treasury of Biologically Active Natural Products（Molecular graphic：Dactylyne，a halogenated marine natural product）

8.1 Introduction：Addition to Alkenes

8.2 Addition of Hydrogen Halides to Alkenes：Markovnikov’s Rule

8.3 Stereochemistry of the Ionic Addition to an Alkene

8.4 Addition of Sulfuric Acid to Alkenes

8.5 Addition of Water to Alkenes：Acid-Catalyzed Hydration

8.6 Alcohols from Alkenes through Oxymercuration-Demercuration：Markovnikov Addition

8.7 Alcohols from Alkenes through Hydroboration-Oxidation：Anti-Markovnikov Syn Hydration

8.8 Hydroboration：Synthesis of Alkylboranes

8.9 Oxidation and Hydrolysis of Alkyboranes

8.10 Summary of Alkene Hydration Methods

8.11 Protonolysis of Alkyboranes

8.12 Addition of Bromine and Chlorine to Alkenes

8.13 Stereochemistry of the Addition of Halogens to Alkenes

8.14 Halohydrin Formation

The Chemistry of…Regiospecificity in Unsymmetrically Substituted Bromonium lons：Bromonium lons of Ethene,Propene,and2-Methlypropene

8.15 Divalent Carbon Compounds：Carbenes

8.16 Oxidations of Alkenes：Syn1，2-Dihydroxylation

The Chemistry of…Catalytic Asymmetric Dihydroxylation

8.17 Oxidative Cleavage of Alkenes

8.18 Addition of Bromine and Chlorine to Alkynes

8.19 Addition of Hydrogen Halides to Alkynes

8.20 Oxidative Cleavage of Alkynes

8.21 Synthetic Strategies Revisited

The Chemistry 0f…Cholesterol Biosynthesis：Elegant and Familiar Reactions in Nature

Chapter 9 Nuclear Magnetic Resonance and Mass Spectrometry：Tools for Structure Determination

A Thermos？of Liquid Helium383（Molecular graphic：1-Chloro-2-propanol）

9.1 Introduction

9.2 The Electromagnetic Spectrum

9.3 Nuclear Magnetic Resonance Spectroscopy

9.4 Nuclear Spin： The Origin of the Signal

9.5 Shielding and Deshielding of Protons

9.6 The Chemical Shift

9.7 Chemical Shift Equivalent and Nonequivalent Protons

9.8 Signal Splitting： Spin-Spin Coupling

9.9 Proton NMR Spectra and Rate Processes

9.10 Carbon-l3 NMR Spectroscopy

9.11 Two-Dimensional（2D）NMR Techniques

The Chemistry of...Magnetic Resonance Imaging In Medicine

9.12 An Introduction to Mass Spectrometry

9.13 The Mass Spectrometer

9.14 The Mass Spectrum

9.15 Determination of Molecular Formulas and Molecular Weights

9.16 Fragmentation

9.17 GC/MS Analysis

9.18 Mass Spectrometry of Biomolecules

Chapter 10 Radical Reactions

Calicheamicin γ1:A Radical Device for Slicing the Backbone of DNA447（Molecular graphic：Calicheamicin γ1Ⅰ，a molecule capable of double-strand DNA cleavage，bound to DNA）

10.1 Introduction

The Chemistry of...Radicals ln Biology,Medicine,and lndustry

10.2 Homolytic Bond Dissociation Energies

10.3 The Reactions of Alkanes with Halogens

10.4 Chlorination of Methane：Mechanism of Reaction

10.5 Chlorination of Methane：Energy Changes

10.6 Halogenation of Higher Alkanes

10.7 The Geometry of Alkyl Radicals

10.8 Reactions that Generate Tetrahedral Stereogenic Carbons

10.9 Radical Addition to Alkenes：The Anti-Markovnikov Addition of Hydrogen Bromide

10.10 Radical Polymerization of Alkenes：Chain-Growth Polymers

10.11 Other Important Radical Reactions

Special Topic A：Chain-Growth Polymers

Chapter 11 Alcohols and Ethers

Molecular Hosts（Molecular graphic：Monensin sodium salt，an antibiotic that transports ions across cell membranes）

11.1 Structure and Nomenclature

11.2 Physical Properties of Alcohols and Ethers

11.3 Important Alcohols and Ethers

11.4 Synthesis of Alcohols from Alkenes

11.5 Reactions of Alcohols

11.6 Alcohols as Acids

11.7 Conversion of Alcohols into Alkyl Halides

11.8 Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides

11.9 Alkyl Halides from the Reaction of Alcohols with PBr3 or SOCl

11.10 Tosylates，Mesylates，and Triflates：Leaving Group Derivatives of Alcohols

The Chemistry of&Alkyl Phosphates

11.11 Synthesis of Ethers

11.12 Reactions of Ethers

11.13 Epoxides

The Chemistry of…The sharpless Asymmetric Epoxidation

11.14 Reactions of Epoxides

The Chemistry of…Epoxides,Carcinogens,and Biological Oxidation

11.15 Anti1，2-Dihydroxylation of Alkenes via Epoxides

The Chemistry of…Environmentally Friendly Alkene Oxidatlon Methods

11.16 Crown Ethers：Nucleophilic Substitution Reactions in Relatively Nonpolar Aprotic Solvents by Phase-Transfer Catalysis

11.17 Summary of Reactions of Alkenes，Alcohols，and Ethers

Chapter 12 Alcohols from Carbonyl Compounds. Oxidation-Reduction and Orgganometallic Compounds

The Two Aspects of the Coenzyme NADH（Molecular graphic：Nicotinamide [niacin]）

12.1 Introduction

12.2 Oxidation-Reduction Reactions in Organic Chemistry

12.3 Alcohols by Reduction of Carbonyl Compounds

The Chemistry of…Alcohol Dehydragenase

The Chemistry of…Stereoselective Reductions of Carbonyl Groups

12.4 Oxidation of Alcohols

12.5 Organometallic Compounds

12.6 Preparation of Organolithium and Organomagnesium Compounds

12.7 Reactions of Organolithium and Organomagnesium Compounds

12.8 Alcohols from Grignard Reagents

12.9 Lithium Dialkylcuprates：The Corey-Posner，Whitesides-House Synthesis

12.10 Protecting Groups

First Review Problem Set

Chapter 13 Conjugated Unsaturated Systems

MoleCuies with the Nobel Prize in Theirsynthetic Lineage（Molecular graphic：Morphine，the synthesis of which involved the Diels-Alder reaction）

13.1 Introduction

13.2 Allylic Substitution and the Allyl Radical

13.3 The Stability of the Allyl Radical

13.4 The Allyl Cation

13.5 Summary of Rules for Resonance

13.6 Alkadienes and Polyunsaturated Hydrocarbons

13.7 1，3-Butadiene：Electron Delocalization

13.8 The Stability of Conjugated Dienes

13.9 Ultraviolet-Visible Spectroscopy

The Chemistry of…The Photochemistry of vision

13.10 Electrophilic Attack on Conjugated Dienes：1，4Addition

13.11 The Diels-Alder Reaction：A1，4-Cycloaddition Reaction of Dienes

Chapter 14 Aromatic Compounds

Geen Chemistry（Molecular graphic：Benzene，parent molecule in the family of aromatic hydrocarbons）

14.1 Introduction

14.2 Nomenclature of Benzene Derivatives

14.3 Reactions of Benzene

14.4 The Kekule Structure for Benzene

14.5 The Stability of Benzene

14.6 Modern Theories of the Structure of Benzene

14.7 Hiickel’s Rule： The 4n+2πElectron Rule

14.8 Other Aromatic Compounds

The Chemistry of…Nanotubes

14.9 Heterocylic Aromatic Compounds

14.10 Aromatic Compounds in Biochemistry

14.11 Spectroscopy of Aromatic Compounds

The Chemistry of…Sunscreens（Catching the Sun’s Rays and what Happens to Them）

Chapter 15 Reactions of Aromatic Compounds

Biosynthesis of Thyroxine：Aromatic Substitution lnvolving Iodine（Molecular graphic：Thyroxine，an aromatic iodine-containing hormone associated with regulation of metabolic rate）

15.1 Electrophilic Aromatic Substitution Reactions

15.2 A General Mechanism for Electrophilic Aromatic Substitution：Arenium Ions

15.3 Halogenation of Benzene

15.4 Nitration of Benzene

15.5 Sulfonation of Benzene

15.6 Friedel-Crafts Alkylation

15.7 Friedel-Crafts Acylation

15.8 Limitations of Friedel-Crafts Reactions

15.9 Synthetic Applications of Friedel-Crafts Acylations：The Clemmensen Reduction

15.10 Effect of Substituents on Reactivity and Orientation

15.11 Theory of Substituent Effects on Electrophilic Aromatic Substitution

The Chemistry of…Iodine lncorporatlon In Thyroxine Biosynthesis

15.12 Reactions of the Side Chain of Alkylbenzenes

The Chemistry of…Industrial Styrene synthesis

15.13 Alkenylbenzenes

15.14 Synthetic Applications

15.15 Allylic and Benzylic Halides in Nucleophilic Substitution Reactions

15.16 Reduction of Aromatic Compounds

Chapter 16 Aldehydes and KetonesI.Nucleophilic Addition to the Carbonyl Group

A Very Versatile Vitamin,Pyridoxine（Vitamin B6）（Molecular graphic：Pyridoxal phosphate[vitamin B6]）

16.1 Introduction

16.2 Nomenclature of Aldehydes and Ketones

16.3 Physical Properties

16.4 Synthesis of Aldehydes

16.5 Synthesis of Ketones

16.6 Nucleophilic Addition to the Carbon-Oxygen Double Bond

16.7 The Addition of Alcohols： Hemiacetals and Acetals

16.8 The Addition of Primary and Secondary Amines

The Chemistry of…Pyridoxal Phosphate

16.9 The Addition of Hydrogen Cyanide

16.10 The Addition of Ylides：The Wittig Reaction

16.11 The Addition of Organometallic Reagents：The Reformatsky Reaction

16.12 Oxidation of Aldehydes and Ketones

16.13 Chemical Analyses for Aldehydes and Ketones

16.14 Spectroscopic Properties of Aldehydes and Ketones

Chaptet 17 Aldehydes and KetonesⅡ.Aldol Reactions

TIM（Triose Phosphate Isomerase）Recycles Carbon via an Enol（Molecular graphic：Glyceraldehyde-3-phosphate， a key intermediate in metabolic energy production）

17.1 The Acidity of the α Hydrogens of Carbonyl Compounds：Enolate Anions

17.2 Keto and Enol Tautomers

17.3 Reactions Via Enols and Enolate Anions

17.4 The Aldol Reaction：The Addition of Enolate Anions to Aldehydes and Ketones

The Chemistry of…A Retro-Aldol Reaction In Glycolysls—Dividing Assets to Double the ATP yield

17.5 Crossed Aldol Reactions

17.6 Cyclizations via Aldol Condensations

17.7 Lithium Enolates

The Chemistry of…Silyl Fnol Ethers

17.8 α-Selenation：A Synthesis of α，β-Unsaturated Carbonyl Compounds

17.9 Additions to α，β3-Unsaturated Carbonyl Compounds

The Chemistry of…Calicheamicin γ1ⅠActivation for Cleavage of DNA

Chapter 18 Carboxylic Acids and Their Derivatives.Nucleophilic Addition-Elimination at the Acyl Carbon

A Common Bond（Molecular graphic：A portion of nylon 6，6，a polyamide）

18.1 Introduction

18.2 Nomenclature and Physical Properties

18.3 Preparation of Carboxylic Acids

18.4 Nucleophilic Addition-Elimination at the Acyl Carbon

18.5 Acyl Chlorides

18.6 Carboxylic Acid Anhydrides

18.7 Esters

18.8 Amides

The Chemistry of…Penicillins

18.9 Derivatives of Carbonic Acid

18.10 Decarboxylation of Carboxylic Acids

The Chemistry of…Thiamine

18.11 Chemical Tests for Acyl Compounds

Special TopicB：Step-Growth Polymers

Chapter 19 Synthesis and Reactions of β-Dicarbonyl Compounds：More Chemistry of Enolate Ions

Imposters（Molecular graphic：5-Fluorouracil， an enzyme inhibitor that has anticancer activity by masquerading as a natural substrate）

19.1 Introduction

19.2 The Claisen Condensation：The Synthesis of β-Keto Esters

19.3 The Acetoacetic Ester Synthesis： Synthesis of Methyl Ketones（Substituted Acetones）

19.4 The Malonic Ester Synthesis： Synthesis of Substituted Acetic Acids

19.5 Further Reactions of Active Hydrogen Compounds

19.6 Direct Alkylation of Esters and Nitriles

19.7 Alkylation of 1，3-Dithianes

19.8 The Knoevenagel Condensation

19.9 Michael Additions

19.10 The Mannich Reaction

The Chenmistry of…A suicide Enzyme substrate

19.11 Synthesis of Enamines：Stork Enamine Reactions

The Chemistry of…Antibody-Catalyzed Aldol Condensations

19.12 Barbiturates

Special Topic C：Thiols，Sulfur Ylides，and Disulfides

Special Topic D：Thiol Esters and Lipid Biosynthesis

Chapter 20 Amines

Neurotoxins and Neurotransmitters（Molecular graphic：Histrionicatoxin，a paralyzing neurotoxin from certain dart frogs）

20.1 Nomenclature

20.2 Physical Properties and Structure of Amines

20.3 Basicity of Amines：Amine Salts

The Chemistry of…HPLC Resolution of Enantiomers

20.4 Some Biologically Important Amines

20.5 Preparation of Amines

20.6 Reactions of Amines

20.7 Reactions of Amines with Nitrous Acid

The Chemistry of…N-Nitrosoamines

20.8 Replacement Reactions of Arenediazonium Salts

20.9 Coupling Reactions of Arenediazonium Salts

20.10 Reactions of Amines with Sulfonyl Chlorides

20.11 The Sulfa Drugs： Sulfanilamide

20.12 Analysis of Amines

20.13 Eliminations Involving Ammonium Compounds

Special TopicE：Alkaloids

Chapter 21 Phenols and Aryl Halides：Nucleophilic Aromatic Substitution

A Silver Chalice（Molecular graphic：4-tert-Butylcalix[4]arene， a chalice-shaped molecule）

21.1 Structure and Nomenclature of Phenols

21.2 Naturally Occurring Phenols

21.3 Physical Properties of Phenols

21.4 Synthesis of Phenols

The Chemistry of…Polyketide Anticancer Antiblotic Biosynthesis

21.5 Reactions of Phenols as Acids

21.6 Other Reactions of the O—H Group of Phenols

21.7 Cleavage of Alkyl Aryl Ethers

21.8 Reactions of the Benzene Ring of Phenols

21.9 The Claisen Rearrangement

21.10 Quinones

21.11 Aryl Halides and Nucleophilic Aromatic Substitution

The Chemistry of…The Bombardier Beetles’s Noxious spray

The Chemistry of…Bacterlal Dehalogenatlon of a PCB Derivative

21.12 Spectroscopic Analysis of Phenols and Aryl Halides

Second Review：Problem Set

Special Topic F：Electrocyclic and Cycloaddition Reactions

Special Topic G：Transition Metal Organometallic Compounds

Special Topic H：Organic Halides and Organometallic Compounds In the Environment

Chapter 22 Carbohydrates

Carhohydrate ReCOgnition in Healing and Disease（Molelcular graphic：Sialyl Lewis，x a carbohydrate that is important in the recognition and healing of traumatized tissue）

22.1 Introduction

22.2 Monosaccharides

22.3 Mutarotation

22.4 Glycoside Formation

22.5 Other Reactions of Monosaccharides

22.6 Oxidation Reactions of Monosaccharides

22.7 Reduction of Monosaccharides：Alditols

22.8 Reactions of Monosaccharides with Phenylhydrazine：Osazones

22.9 Synthesis and Degradation of Monosaccharides

22.10 The D Family of Aldoses

22.11 Fischer’s Proof of the Configuration of D-（+）-Glucose

The Chemistry of…Stereoselective synthesis of All the L-Aldohexoses

22.12 Disaccharides

The Chemistry of…Artificial Sweeteners（How sweet it is）

22.13 Polysaccharides

The Chemistry of…Oligosaccharldes synthesis on a Solid Support-The Glycal Assembly Approach

22.14 Other Biologically Important Sugars

22.15 Sugars that Contain Nitrogen

22.16 Glycolipids and Glycoproteins of the Cell Surface：Cell Recognition and the Immune System

The Chemistry of…Vacclnes Agalnst CanCer

22.17 Carbohydrate Antibiotics

Chapter 23 Lipids

lnsulation for Nerves（Molecular graphic：A sphingomyelin molecule，found in myelin sheath membranes）

23.1 Introduction

23.2 Fatty Acids and Triacylglycerols

The Chemistry of…Olestra and Other Fat Substitutes

Thhe Chemistry of…Self-Assembled Monolayers—Lipids in Materials SCienCe and Bioengineering

23.3 Terpenes and Terpenoids

23.4 Steroids

23.5 Prostaglandins

23.6 Phospholipids and Cell Membranes

The Chemistry of…Stealth? Lipesomes for Drug Delivery

23.7 Waxes

Chapter 24 Amino Acids and Proteins

Catalytic Antibodies：Designer Catalysts（Molecular graphic：A synthetic Diels-Alderase catalytic antibody with a bound hapten）

24.1 Introduction

24.2 Amnino Acids

24.3 Synthesis of α-Amino Acids

24.4 Polypeptides and Proteins

24.5 Primary Structure of Polypeptides and Proteins

24.6 Examples of Polypeptide and Protein Primary Structure

The Chemistry of…Sickle-Cell Anemia

24.7 Polypeptide and Protein Synthesis

24.8 Secondary，Tertiary， and Quaternary Structure of Proteins

24.9 Introduction to Enzymes

24.10 Lysozyme：Mode of Action of an Enzyme

24.11 Serine Proteases

The Chemistry of…Some CatalytiC Antibodies

24.12 Hemoglobin：A Conjugated Protein

24.13 Purification and Analysis of Polypeptides and Proteins

24.14 Proteomics

Chapter 25 NUCleic Acids and Protein Synthesis

Tools for Finding Families（Molecular graphic：A cytosine-guanine base pair， depicting the van der Waals surface as an electrostatic potential map）

25.1 Introduction

25.2 Nucleotides and Nucleosides

25.3 Laboratory Synthesis of Nucleosides and Nucleotides

25.4 Deoxyribonucleic Acid：DNA

25.5 RNA and Protein Synthesis

25.6 Determining the Base Sequence of DNA：The Chain Terminating （Dideoxynucleotide Method）

25.7 Laboratory Syntesis of Oligonucleotides

25.8 The Polymerase Chain Reaction

25.9 Sequencing of the Human Genome：An Instruction Book for the Molecules of Life