Organic Chemistry 9th Edition by John Mcmurry ISBN 9781305080485 1305080483

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ISBN 10: 1305080483
ISBN 13: 9781305080485
Author: John Mcmurry

Organic Chemistry 9th Edition Table of contents:

1. Structure and Bonding

1-1. Atomic Structure: The Nucleus

1-2. Atomic Structure: Orbitals

1-3. Atomic Structure: Electron Configurations

1-4. Development of Chemical Bonding Theory

1-5. Describing Chemical Bonds: Valence Bond Theory

1-6. sp 3 Hybrid Orbitals and the Structure of Methane

1-7. sp 3 Hybrid Orbitals and the Structure of Ethane

1-8. sp 2 Hybrid Orbitals and the Structure of Ethylene

1-9. sp Hybrid Orbitals and the Structure of Acetylene

1-10. Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur

1-11. Describing Chemical Bonds: Molecular Orbital Theory

1-12. Drawing Chemical Structures

Something Extra. Organic Foods: Risk versus Benefit

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Additional Problems

2. Polar Covalent Bonds; Acids and Bases

2-1. Polar Covalent Bonds: Electronegativity

2-2. Polar Covalent Bonds: Dipole Moments

2-3. Formal Charges

2-4. Resonance

2-5. Rules for Resonance Forms

2-6. Drawing Resonance Forms

2-7. Acids and Bases: The Brønsted–Lowry Definition

2-8. Acid and Base Strength

2-9. Predicting Acid–Base Reactions from p ‍ K a Values

2-10. Organic Acids and Organic Bases

Organic Acids

Organic Bases

2-11. Acids and Bases: The Lewis Definition

Lewis Acids and the Curved Arrow Formalism

Lewis Bases

2-12. Noncovalent Interactions between Molecules

Something Extra. Alkaloids: From Cocaine to Dental Anesthetics

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

3. Organic Compounds: Alkanes and Their Stereochemistry

3-1. Functional Groups

Functional Groups with Carbon–Carbon Multiple Bonds

Functional Groups with Carbon Singly Bonded to an Electronegative Atom

Functional Groups with a Carbon–Oxygen Double Bond (Carbonyl Groups)

3-2. Alkanes and Alkane Isomers

3-3. Alkyl Groups

3-4. Naming Alkanes

3-5. Properties of Alkanes

3-6. Conformations of Ethane

3-7. Conformations of Other Alkanes

Something Extra. Gasoline

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Additional Problems

4. Organic Compounds: Cycloalkanes and Their Stereochemistry

4-1. Naming Cycloalkanes

4-2. Cis–Trans Isomerism in Cycloalkanes

4-3. Stability of Cycloalkanes: Ring Strain

4-4. Conformations of Cycloalkanes

Cyclopropane

Cyclobutane

Cyclopentane

4-5. Conformations of Cyclohexane

4-6. Axial and Equatorial Bonds in Cyclohexane

4-7. Conformations of Monosubstituted Cyclohexanes

4-8. Conformations of Disubstituted Cyclohexanes

4-9. Conformations of Polycyclic Molecules

Something Extra. Molecular Mechanics

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Additional Problems

5. Stereochemistry at Tetrahedral Centers

5-1. Enantiomers and the Tetrahedral Carbon

5-2. The Reason for Handedness in Molecules: Chirality

5-3. Optical Activity

5-4. Pasteur’s Discovery of Enantiomers

5-5. Sequence Rules for Specifying Configuration

5-6. Diastereomers

5-7. Meso Compounds

5-8. Racemic Mixtures and the Resolution of Enantiomers

5-9. A Review of Isomerism

5-10. Chirality at Nitrogen, Phosphorus, and Sulfur

5-11. Prochirality

5-12. Chirality in Nature and Chiral Environments

Something Extra. Chiral Drugs

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Additional Problems

6. An Overview of Organic Reactions

6-1. Kinds of Organic Reactions

6-2. How Organic Reactions Occur: Mechanisms

6-3. Radical Reactions

6-4. Polar Reactions

6-5. An Example of a Polar Reaction: Addition of HBr to Ethylene

6-6. Using Curved Arrows in Polar Reaction Mechanisms

6-7. Describing a Reaction: Equilibria, Rates, and Energy Changes

6-8. Describing a Reaction: Bond Dissociation Energies

6-9. Describing a Reaction: Energy Diagrams and Transition States

6-10. Describing a Reaction: Intermediates

6-11. A Comparison between Biological Reactions and Laboratory Reactions

Something Extra. Where Do Drugs Come From?

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Energy Diagrams and Reaction Mechanisms

Exercises: Additional Problems

Practice Your Scientific Analysis and Reasoning I

Practice Your Scientific Analysis and Reasoning I

7. Alkenes: Structure and Reactivity

7-1. Industrial Preparation and Use of Alkenes

7-2. Calculating Degree of Unsaturation

7-3. Naming Alkenes

7-4. Cis–Trans Isomerism in Alkenes

7-5. Alkene Stereochemistry and the E,Z Designation

7-6. Stability of Alkenes

7-7. Electrophilic Addition Reactions of Alkenes

7-8. Orientation of Electrophilic Additions: Markovnikov’s Rule

7-9. Carbocation Structure and Stability

7-10. The Hammond Postulate

7-11. Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements

Something Extra. Bioprospecting: Hunting for Natural Products

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

8. Alkenes: Reactions and Synthesis

8-1. Preparing Alkenes: A Preview of Elimination Reactions

8-2. Halogenation of Alkenes: Addition of X 2

8-3. Halohydrins from Alkenes: Addition of HOX

8-4. Hydration of Alkenes: Addition of H 2 ‍ O by Oxymercuration

8-5. Hydration of Alkenes: Addition of H 2 ‍ O by Hydroboration

8-6. Reduction of Alkenes: Hydrogenation

8-7. Oxidation of Alkenes: Epoxidation and Hydroxylation

8-8. Oxidation of Alkenes: Cleavage to Carbonyl Compounds

8-9. Addition of Carbenes to Alkenes: Cyclopropane Synthesis

8-10. Radical Additions to Alkenes: Chain-Growth Polymers

8-11. Biological Additions of Radicals to Alkenes

8-12. Reaction Stereochemistry: Addition of H 2 ‍ O to an Achiral Alkene

8-13. Reaction Stereochemistry: Addition of H 2 ‍ O to a Chiral Alkene

Something Extra. Terpenes: Naturally Occurring Alkenes

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

9. Alkynes: An Introduction to Organic Synthesis

9-1. Naming Alkynes

9-2. Preparation of Alkynes: Elimination Reactions of Dihalides

9-3. Reactions of Alkynes: Addition of HX and X 2

9-4. Hydration of Alkynes

Mercury(II)-Catalyzed Hydration of Alkynes

Hydroboration–Oxidation of Alkynes

9-5. Reduction of Alkynes

9-6. Oxidative Cleavage of Alkynes

9-7. Alkyne Acidity: Formation of Acetylide Anions

9-8. Alkylation of Acetylide Anions

9-9. An Introduction to Organic Synthesis

Something Extra. The Art of Organic Synthesis

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

10. Organohalides

10-1. Names and Structures of Alkyl Halides

10-2. Preparing Alkyl Halides from Alkanes: Radical Halogenation

10-3. Preparing Alkyl Halides from Alkenes: Allylic Bromination

10-4. Stability of the Allyl Radical: Resonance Revisited

10-5. Preparing Alkyl Halides from Alcohols

10-6. Reactions of Alkyl Halides: Grignard Reagents

10-7. Organometallic Coupling Reactions

10-8. Oxidation and Reduction in Organic Chemistry

Something Extra. Naturally Occurring Organohalides

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations

11-1. The Discovery of Nucleophilic Substitution Reactions

11-2. The S N ‍ 2 Reaction

11-3. Characteristics of the S N ‍ 2 Reaction

The Substrate: Steric Effects in the S N ‍ 2 Reaction

The Nucleophile

The Leaving Group

The Solvent

A Summary of S N ‍ 2 Reaction Characteristics

11-4. The S N ‍ 1 Reaction

11-5. Characteristics of the S N ‍ 1 Reaction

The Substrate

The Leaving Group

The Nucleophile

The Solvent

A Summary of S N 1 Reaction Characteristics

11-6. Biological Substitution Reactions

11-7. Elimination Reactions: Zaitsev’s Rule

11-8. The E2 Reaction and the Deuterium Isotope Effect

11-9. The E2 Reaction and Cyclohexane Conformation

11-10. The E1 and E1cB Reactions

The E1 Reaction

The E1cB Reaction

11-11. Biological Elimination Reactions

11-12. A Summary of Reactivity: S N ‍ 1 , S N ‍ 2 , E1, E1cB, and E2

Something Extra. Green Chemistry

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

Practice Your Scientific Analysis and Reasoning II

Practice Your Scientific Analysis and Reasoning II

12. Structure Determination: Mass Spectrometry and Infrared Spectroscopy

12-1. Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments

12-2. Interpreting Mass Spectra

12-3. Mass Spectrometry of Some Common Functional Groups

Alcohols

Amines

Halides

Carbonyl Compounds

12-4. Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments

12-5. Spectroscopy and the Electromagnetic Spectrum

12-6. Infrared Spectroscopy

12-7. Interpreting Infrared Spectra

12-8. Infrared Spectra of Some Common Functional Groups

Alkanes

Alkenes

Alkynes

Aromatic Compounds

Alcohols

Amines

Carbonyl Compounds

Something Extra. X-Ray Crystallography

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Additional Problems

13. Structure Determination: Nuclear Magnetic Resonance Spectroscopy

13-1. Nuclear Magnetic Resonance Spectroscopy

13-2. The Nature of NMR Absorptions

13-3. The Chemical Shift

13-4. Chemical Shifts in H 1 NMR Spectroscopy

13-5. Integration of H 1 NMR Absorptions: Proton Counting

13-6. Spin–Spin Splitting in H 1 NMR Spectra

13-7. H 1 NMR Spectroscopy and Proton Equivalence

13-8. More Complex Spin–Spin Splitting Patterns

13-9. Uses of H 1 NMR Spectroscopy

13-10. C 13 NMR Spectroscopy: Signal Averaging and FT–NMR

13-11. Characteristics of C 13 NMR Spectroscopy

13-12. DEPT C 13 NMR Spectroscopy

13-13. Uses of C 13 NMR Spectroscopy

Something Extra. Magnetic Resonance Imaging (MRI)

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Additional Problems

Exercises: General Problems

14. Conjugated Compounds and Ultraviolet Spectroscopy

14-1. Stability of Conjugated Dienes: Molecular Orbital Theory

14-2. Electrophilic Additions to Conjugated Dienes: Allylic Carbocations

14-3. Kinetic versus Thermodynamic Control of Reactions

14-4. The Diels–Alder Cycloaddition Reaction

14-5. Characteristics of the Diels–Alder Reaction

The Dienophile

The Diene

14-6. Diene Polymers: Natural and Synthetic Rubbers

14-7. Ultraviolet Spectroscopy

14-8. Interpreting Ultraviolet Spectra: The Effect of Conjugation

14-9. Conjugation, Color, and the Chemistry of Vision

Something Extra. Photolithography

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

Practice Your Scientific Analysis and Reasoning III

Practice Your Scientific Analysis and Reasoning III

15. Benzene and Aromaticity

15-1. Naming Aromatic Compounds

15-2. Structure and Stability of Benzene

15-3. Aromaticity and the Hückel 4 n + 2 Rule

15-4. Aromatic Ions

15-5. Aromatic Heterocycles: Pyridine and Pyrrole

15-6. Polycyclic Aromatic Compounds

15-7. Spectroscopy of Aromatic Compounds

Infrared Spectroscopy

Ultraviolet Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Something Extra. Aspirin, NSAIDs, and COX-2 Inhibitors

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Additional Problems

16. Chemistry of Benzene: Electrophilic Aromatic Substitution

16-1. Electrophilic Aromatic Substitution Reactions: Bromination

16-2. Other Aromatic Substitutions

Aromatic Halogenation

Aromatic Nitration

Aromatic Sulfonation

Aromatic Hydroxylation

16-3. Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction

16-4. Substituent Effects in Electrophilic Substitutions

Activating and Deactivating Effects

Ortho- and Para-Directing Activators: Alkyl Groups

Ortho- and Para-Directing Activators: OH and NH 2

Ortho- and Para-Directing Deactivators: Halogens

Meta-Directing Deactivators

A Summary of Substituent Effects in Electrophilic Aromatic Substitution

16-5. Trisubstituted Benzenes: Additivity of Effects

16-6. Nucleophilic Aromatic Substitution

16-7. Benzyne

16-8. Oxidation of Aromatic Compounds

Oxidation of Alkyl Side Chains

Bromination of Alkylbenzene Side Chains

16-9. Reduction of Aromatic Compounds

Catalytic Hydrogenation of Aromatic Rings

Reduction of Aryl Alkyl Ketones

16-10. Synthesis of Polysubstituted Benzenes

Something Extra. Combinatorial Chemistry

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

17. Alcohols and Phenols

17-1. Naming Alcohols and Phenols

17-2. Properties of Alcohols and Phenols

17-3. Preparation of Alcohols: A Review

17-4. Alcohols from Carbonyl Compounds: Reduction

Reduction of Aldehydes and Ketones

Reduction of Carboxylic Acids and Esters

17-5. Alcohols from Carbonyl Compounds: Grignard Reaction

17-6. Reactions of Alcohols

Conversion of Alcohols into Alkyl Halides

Conversion of Alcohols into Tosylates

Dehydration of Alcohols to Yield Alkenes

Conversion of Alcohols into Esters

17-7. Oxidation of Alcohols

17-8. Protection of Alcohols

17-9. Phenols and Their Uses

17-10. Reactions of Phenols

Electrophilic Aromatic Substitution Reactions

Oxidation of Phenols: Quinones

17-11. Spectroscopy of Alcohols and Phenols

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

Something Extra. Ethanol: Chemical, Drug, Poison

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

18. Ethers and Epoxides; Thiols and Sulfides

18-1. Names and Properties of Ethers

18-2. Preparing Ethers

The Williamson Ether Synthesis

Alkoxymercuration of Alkenes

18-3. Reactions of Ethers: Acidic Cleavage

18-4. Reactions of Ethers: Claisen Rearrangement

18-5. Cyclic Ethers: Epoxides

18-6. Reactions of Epoxides: Ring-Opening

Acid-Catalyzed Epoxide Opening

Base-Catalyzed Epoxide Opening

18-7. Crown Ethers

18-8. Thiols and Sulfides

Thiols

Sulfides

18-9. Spectroscopy of Ethers

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Something Extra. Epoxy Resins and Adhesives

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

Exercises: General Problems

Preview of Carbonyl Chemistry

I. Kinds of Carbonyl Compounds

II. Nature of the Carbonyl Group

III. General Reactions of Carbonyl Compounds

Nucleophilic Addition Reactions of Aldehydes and Ketones (Chapter 19)

Nucleophilic Acyl Substitution Reactions of Carboxylic Acid Derivatives (Chapter 21)

Alpha-Substitution Reactions (Chapter 22)

Carbonyl Condensation Reactions (Chapter 23)

IV. Summary

Problems

19. Aldehydes and Ketones: Nucleophilic Addition Reactions

19-1. Naming Aldehydes and Ketones

19-2. Preparing Aldehydes and Ketones

Preparing Aldehydes

Preparing Ketones

19-3. Oxidation of Aldehydes and Ketones

19-4. Nucleophilic Addition Reactions of Aldehydes and Ketones

19-5. Nucleophilic Addition of H 2 ‍ O : Hydration

19-6. Nucleophilic Addition of HCN : Cyanohydrin Formation

19-7. Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation

Addition of Hydride Reagents: Reduction

Addition of Grignard Reagents, RMgX

19-8. Nucleophilic Addition of Amines: Imine and Enamine Formation

19-9. Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction

19-10. Nucleophilic Addition of Alcohols: Acetal Formation

19-11. Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction

19-12. Biological Reductions

19-13. Conjugate Nucleophilic Addition to α , β -Unsaturated Aldehydes and Ketones

Conjugate Addition of Amines

Conjugate Addition of Water

Conjugate Addition of Alkyl Groups: Organocopper Reactions

19-14. Spectroscopy of Aldehydes and Ketones

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

Something Extra. Enantioselective Synthesis

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

Practice Your Scientific Analysis and Reasoning IV

Practice Your Scientific Analysis and Reasoning IV

20. Carboxylic Acids and Nitriles

20-1. Naming Carboxylic Acids and Nitriles

Carboxylic Acids, RCO 2 ‍ H

Nitriles, RC ≡ N

20-2. Structure and Properties of Carboxylic Acids

20-3. Biological Acids and the Henderson–Hasselbalch Equation

20-4. Substituent Effects on Acidity

20-5. Preparing Carboxylic Acids

Hydrolysis of Nitriles

Carboxylation of Grignard Reagents

20-6. Reactions of Carboxylic Acids: An Overview

20-7. Chemistry of Nitriles

Preparation of Nitriles

Reactions of Nitriles

20-8. Spectroscopy of Carboxylic Acids and Nitriles

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Something Extra. Vitamin C

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

21-1. Naming Carboxylic Acid Derivatives

Acid Halides, RCOX

Acid Anhydrides, RCO 2 ‍ COR ′

Esters, RCO 2 ‍ R ′

Amides, RCONH 2

Thioesters, RCOSR ′

Acyl Phosphates, RCO 2 ‍ PO 3 2 – and RCO 2 ‍ PO 3 ‍ R ′ –

21-2. Nucleophilic Acyl Substitution Reactions

Relative Reactivity of Carboxylic Acid Derivatives

21-3. Reactions of Carboxylic Acids

Conversion of Carboxylic Acids into Acid Chlorides

Conversion of Carboxylic Acids into Acid Anhydrides

Conversion of Carboxylic Acids into Esters

Conversion of Carboxylic Acids into Amides

Conversion of Carboxylic Acids into Alcohols

Biological Conversions of Carboxylic Acids

21-4. Chemistry of Acid Halides

Preparation of Acid Halides

Reactions of Acid Halides

Conversion of Acid Chlorides into Alcohols: Reduction and Grignard Reaction

Conversion of Acid Chlorides into Ketones: Diorganocopper Reaction

21-5. Chemistry of Acid Anhydrides

Preparation of Acid Anhydrides

Reactions of Acid Anhydrides

21-6. Chemistry of Esters

Preparation of Esters

Reactions of Esters

21-7. Chemistry of Amides

Preparation of Amides

Reactions of Amides

21-8. Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives

21-9. Polyamides and Polyesters: Step-Growth Polymers

Polyamides (Nylons)

Polyesters

Sutures and Biodegradable Polymers

21-10. Spectroscopy of Carboxylic Acid Derivatives

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Something Extra. β -Lactam Antibiotics

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

22. Carbonyl Alpha-Substitution Reactions

22-1. Keto–Enol Tautomerism

22-2. Reactivity of Enols: α -Substitution Reactions

22-3. Alpha Halogenation of Aldehydes and Ketones

22-4. Alpha Bromination of Carboxylic Acids

22-5. Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation

22-6. Reactivity of Enolate Ions

22-7. Alkylation of Enolate Ions

Malonic Ester Synthesis

Acetoacetic Ester Synthesis

Direct Alkylation of Ketones, Esters, and Nitriles

Biological Alkylations

Something Extra. Barbiturates

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

23. Carbonyl Condensation Reactions

23-1. Carbonyl Condensations: The Aldol Reaction

23-2. Carbonyl Condensations versus Alpha Substitutions

23-3. Dehydration of Aldol Products: Synthesis of Enones

23-4. Using Aldol Reactions in Synthesis

23-5. Mixed Aldol Reactions

23-6. Intramolecular Aldol Reactions

23-7. The Claisen Condensation Reaction

23-8. Mixed Claisen Condensations

23-9. Intramolecular Claisen Condensations: The Dieckmann Cyclization

23-10. Conjugate Carbonyl Additions: The Michael Reaction

23-11. Carbonyl Condensations with Enamines: The Stork Reaction

23-12. The Robinson Annulation Reaction

23-13. Some Biological Carbonyl Condensation Reactions

Biological Aldol Reactions

Biological Claisen Condensations

Something Extra. A Prologue to Metabolism

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

Practice Your Scientific Analysis and Reasoning V

Practice Your Scientific Analysis and Reasoning V

24. Amines and Heterocycles

24-1. Naming Amines

24-2. Structure and Properties of Amines

24-3. Basicity of Amines

24-4. Basicity of Arylamines

24-5. Biological Amines and the Henderson–Hasselbalch Equation

24-6. Synthesis of Amines

Reduction of Nitriles, Amides, and Nitro Compounds

S N ‍ 2 Reactions of Alkyl Halides

Reductive Amination of Aldehydes and Ketones

Hofmann and Curtius Rearrangements

24-7. Reactions of Amines

Alkylation and Acylation

Hofmann Elimination

24-8. Reactions of Arylamines

Electrophilic Aromatic Substitution

Diazonium Salts: The Sandmeyer Reaction

Diazonium Coupling Reactions

24-9. Heterocyclic Amines

Pyrrole and Imidazole

Pyridine and Pyrimidine

Polycyclic Heterocycles

24-10. Spectroscopy of Amines

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

Something Extra. Green Chemistry II: Ionic Liquids

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

25. Biomolecules: Carbohydrates

25-1. Classification of Carbohydrates

25-2. Representing Carbohydrate Stereochemistry: Fischer Projections

25-3. D , L Sugars

25-4. Configurations of the Aldoses

25-5. Cyclic Structures of Monosaccharides: Anomers

25-6. Reactions of Monosaccharides

Ester and Ether Formation

Glycoside Formation

Biological Ester Formation: Phosphorylation

Reduction of Monosaccharides

Oxidation of Monosaccharides

Chain Lengthening: The Kiliani–Fischer Synthesis

Chain Shortening: The Wohl Degradation

25-7. The Eight Essential Monosaccharides

25-8. Disaccharides

Maltose and Cellobiose

Lactose

Sucrose

25-9. Polysaccharides and Their Synthesis

Cellulose

Starch and Glycogen

Polysaccharide Synthesis

25-10. Some Other Important Carbohydrates

25-11. Cell-Surface Carbohydrates and Influenza Viruses

Something Extra. Sweetness

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

26. Biomolecules: Amino Acids, Peptides, and Proteins

26-1. Structures of Amino Acids

26-2. Amino Acids and the Henderson–Hasselbalch Equation: Isoelectric Points

26-3. Synthesis of Amino Acids

Amidomalonate Synthesis

Reductive Amination of α -Keto Acids

Enantioselective Synthesis

26-4. Peptides and Proteins

26-5. Amino Acid Analysis of Peptides

26-6. Peptide Sequencing: The Edman Degradation

26-7. Peptide Synthesis

26-8. Automated Peptide Synthesis: The Merrifield Solid-Phase Method

26-9. Protein Structure

26-10. Enzymes and Coenzymes

26-11. How Do Enzymes Work? Citrate Synthase

Something Extra. The Protein Data Bank

Summary

Key Words

Summary of Reactions

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

27. Biomolecules: Lipids

27-1. Waxes, Fats, and Oils

27-2. Soap

27-3. Phospholipids

27-4. Prostaglandins and Other Eicosanoids

27-5. Terpenoids

The Mevalonate Pathway to Isopentenyl Diphosphate

Conversion of Isopentenyl Diphosphate to Terpenoids

27-6. Steroids

Steroid Hormones

Sex Hormones

27-7. Biosynthesis of Steroids

Something Extra. Saturated Fats, Cholesterol, and Heart Disease

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

Practice Your Scientific Analysis and Reasoning VI

Practice Your Scientific Analysis and Reasoning VI

28. Biomolecules: Nucleic Acids

28-1. Nucleotides and Nucleic Acids

28-2. Base Pairing in DNA: The Watson–Crick Model

28-3. Replication of DNA

28-4. Transcription of DNA

28-5. Translation of RNA: Protein Biosynthesis

28-6. DNA Sequencing

28-7. DNA Synthesis

28-8. The Polymerase Chain Reaction

Something Extra. DNA Fingerprinting

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

29. The Organic Chemistry of Metabolic Pathways

29-1. An Overview of Metabolism and Biochemical Energy

29-2. Catabolism of Triacylglycerols: The Fate of Glycerol

29-3. Catabolism of Triacylglycerols: β -Oxidation

29-4. Biosynthesis of Fatty Acids

29-5. Catabolism of Carbohydrates: Glycolysis

29-6. Conversion of Pyruvate to Acetyl CoA

29-7. The Citric Acid Cycle

29-8. Carbohydrate Biosynthesis: Gluconeogenesis

29-9. Catabolism of Proteins: Deamination

Transamination

29-10. Some Conclusions about Biological Chemistry

Something Extra. Statin Drugs

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

30. Orbitals and Organic Chemistry: Pericyclic Reactions

30-1. Molecular Orbitals of Conjugated Pi Systems

30-2. Electrocyclic Reactions

30-3. Stereochemistry of Thermal Electrocyclic Reactions

30-4. Photochemical Electrocyclic Reactions

30-5. Cycloaddition Reactions

30-6. Stereochemistry of Cycloadditions

30-7. Sigmatropic Rearrangements

30-8. Some Examples of Sigmatropic Rearrangements

30-9. A Summary of Rules for Pericyclic Reactions

Something Extra. Vitamin D, the Sunshine Vitamin

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

Practice Your Scientific Analysis and Reasoning VII

Practice Your Scientific Analysis and Reasoning VII

31. Synthetic Polymers

31-1. Chain-Growth Polymers

31-2. Stereochemistry of Polymerization: Ziegler–Natta Catalysts

31-3. Copolymers

31-4. Step-Growth Polymers

Polycarbonates

Polyurethanes

31-5. Olefin Metathesis Polymerization

31-6. Polymer Structure and Physical Properties

Something Extra. Biodegradable Polymers

Summary

Key Words

Exercises: Visualizing Chemistry

Exercises: Mechanism Problems

Exercises: Additional Problems

A. Nomenclature of Polyfunctional Organic Compounds

B. Acidity Constants for Some Organic Compounds

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