Organic Chemistry

 Paula Yurkanis Bruice was raised primarily in Massachusetts. After graduating from the Girls’ Latin School in Boston, she earned an A.B. from Mount Holyoke College and a Ph.D. in chemistry from the University of Virginia. She then received an NIH postdoctoral fellowship for study in the Department of Biochemistry at the University of Virginia Medical School and held a postdoctoral appointment in the Department of Pharmacology at Yale Medical School.  Paula has been a member of the faculty at the University of California, Santa Barbara since 1972, where she has received the Associated Students Teacher of the Year Award, the Academic Senate Distinguished Teaching Award, two Mortar Board Professor of the Year Awards, and the UCSB Alumni Association Teaching Award. Her research interests center on the mechanism and catalysis of organic reactions, particularly those of biological significance. Paula has a daughter and a son who are physicians and a son who is a lawyer. Her main hobbies are reading mystery and suspense novels and enjoying her pets (two dogs, two cats, and a parrot).

Part 1 An Introduction to the Study of Organic Chemistry

 

1 Remembering General Chemistry: Electronic Structure and Bonding

1.1 The Structure of an Atom

1.2 How the Electrons in an Atom Are Distributed

1.3 Ionic and Covalent Bonds

1.4 How the Structure of a Compound Is Represented

1.5 Atomic Orbitals

1.6 An Introduction to Molecular Orbital Theory

1.7 How Single Bonds Are Formed in Organic Compounds

1.8 How a Double Bond Is Formed: The Bonds in Ethene

1.9 How a Triple Bond Is Formed: The Bonds in Ethyne

1.10 The Bonds in the Methyl Cation, the Methyl Radical, and the Methyl Anion

1.11 The Bonds in Ammonia and In the Ammonium Ion

1.12 The Bonds in Water

1.13 The Bond in a Hydrogen Halide

1.14 Hybridization and Molecular Geometry

1.15 Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles

1.16 The Dipole Moments of Molecules

 

2 Acids and Bases: Central to Understanding Organic Chemistry

2.1 An Introduction to Acids and Bases

2.2 pka and pH

2.3 Organic Acids and Bases

2.4 How to Predict the Outcome of an Acid—Base Reaction

2.5 How to Determine the Position of Equilibrium

2.6 How the Structure of an Acid affects its pKa Value

2.7 How Substituent’s affect the Strength of an Acid

2.8 An Introduction to Delocalized Electrons

2.9 A Summary of the Factors That Determine Acid Strength

2.10 How pH affects the Structure of an Organic Compound

2.11 Buffer Solutions

2.12 Lewis Acids and Bases

 

Tutorial: Acids and Bases

 

3 An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure

3.1 How Alkyl Substituents Are Named

3.2 The Nomenclature of Alkanes

3.3 The Nomenclature of Cycloalkanes • Skeletal Structures

3.4 The Nomenclature of Alkyl Halides

3.5 The Nomenclature of Ethers

3.6 The Nomenclature of Alcohols

3.7 The Nomenclature of Amines

3.8 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines

3.9 The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines

3.10 Rotation Occurs about Carbon—Carbon single Bonds

3.11 Some Cycloalkanes Have Angle Strain

3.12 The Conformers of Cyclohexane

3.13 Conformers of Monosubstituted Cyclohexanes

3.14 Conformers of Disubstituted Cyclohexanes

3.15 Fused Cyclohexane Rings

 

Part Two Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization

 

Tutorial: Using Molecular Models

 

4 Isomers: The Arrangement of Atoms in Space

4.1 Cis—Trans Isomers Result from Restricted Rotation

4.2 A Chiral Object Has a Nonsuperimposable Mirror Image

4.3 An Asymmetric Center is a Cause of Chirality in a Molecule

4.4 Isomers with One Asymmetric Center

4.5 Asymmetric Centers and Stereocenters

4.6 How to Draw Enantiomers

4.7 Naming Enantiomers by the R, S System

4.8 Chiral Compounds Are Optically Active

4.9 How Specific Rotation Is Measured

4.10 Enantiomeric Excess

4.11 Compounds with More than One Asymmetric Center

4.12 Stereoisomers of Cyclic Compounds

4.13 Meso Compounds Have Asymmetric Centers but Are Optically Inactive

4.14 How to Name Isomers with More than One Asymmetric Center

4.15 How Enantiomers Can be Separated

4.16 Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers

 

Tutorial: Interconverting Structural Representations

 

5 Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics

5.1 Molecular Formulas and the Degree of Unsaturation

5.2 The Nomenclature of Alkenes

5.3 The Structure of Alkenes

5.4 Naming Alkenes Using the E,Z System

5.5 How an Organic Compound Reacts Depends On Its Functional Group

5.6 How Alkenes React • Curved Arrows Show the Flow of Electrons

5.7 Thermodynamics and Kinetics

5.8 The Rate of a Chemical Reaction

5.9 The Difference between the Rate of a Reaction and the Rate Constant for a Reaction

5.10 A Reaction Coordinate Diagram Describes the Energy Changes that Take Place during a Reaction

5.11 Catalysis

5.12 Catalysis by Enzymes

 

Tutorial: An Exercise in Drawing Curved Arrows: Pushing Electrons

 

6 The Reactions of Alkenes: The Stereochemistry of Addition Reactions

6.1 The Addition of a Hydrogen Halide to an Alkene

6.2 Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon

6.3 What Does the Structure of the Transition State Look Like?

6.4 Electrophilic Addition Reactions Are Regioselective

6.5 The Addition of Water to an Alkene

6.6 The Addition of an Alcohol to an Alkene

6.7 A Carbocation will rearrange if it can Form a More Stable Carbocation

6.8 Oxymercuration—Demercuration Is another Way to Add Water to an Alkene

6.9 The Addition of Borane to an Alkene: Hydroboration—Oxidation

6.10 The Addition of a Halogen to an Alkene

6.11 The Addition of a Peroxyacid to an Alkene

6.12 The Addition Of Ozone To An Alkene: Ozonolysis

6.13 The Addition of Hydrogen to an Alkene

6.14 The Relative Stabilities of Alkenes

6.15 Regioselective, Stereoselective, and Stereospecific Reactions

6.16 The Stereochemistry of Electrophilic Addition Reactions of Alkenes

6.17 The Stereochemistry of Enzyme-Catalyzed Reactions

6.18 Enantiomers Can Be Distinguished by Biological Molecules

6.19 Reactions and Synthesis

 

7 The Reactions of Alkynes: An Introduction to Multistep Synthesis

7.1 The Nomenclature of Alkynes

7.2 How to Name a Compound That Has More than One Functional Group

7.3 The Physical Properties of Unsaturated Hydrocarbons

7.4 The Structure of Alkynes

7.5 Alkynes Are Less Reactive than Alkenes

7.6 The Addition of Hydrogen Halides and the Addition of Halogens to an Alkyne

7.7 The Addition of Water to an Alkyne

7.8 The Addition of Borane to an Alkyne: Hydroboration—Oxidation

7.9 The Addition of Hydrogen to an Alkyne

7.10 A Hydrogen Bonded to an sp Carbon Is “Acidic”

7.11 Synthesis Using Acetylide Ions

7.12 Designing a Synthesis I: An Introduction to Multistep Synthesis

 

8 Delocalized Electrons and Their Effect on Stability, pKa, and the Products of a Reaction

8.1 Delocalized Electrons Explain Benzene’s Structure

8.2 The Bonding in Benzene

8.3 Resonance Contributors and the Resonance Hybrid

8.4 How to Draw Resonance Contributors

8.5 The Predicted Stabilities of Resonance Contributors

8.6 Delocalization Energy Is the Additional Stability Delocalized Electrons Give to a Compound

8.7 Benzene is an Aromatic Compound

8.8 The Two Criteria for Aromaticity

8.9 Applying the Criteria for Aromaticity

8.10 Aromatic Heterocyclic Compounds

8.11 Antiaromaticity

8.12 A Molecular Orbital Description of Aromaticity and Antiaromaticity

8.13 More Examples that Show How Delocalized Electrons Affect Stability

8.14 A Molecular Orbital Description of Stability

8.15 How Delocalized Electrons Affect pKa Values

8.16 Delocalized Electrons Can Affect the Product of a Reaction

8.17 Reactions of Dienes

8.18 Thermodynamic Versus Kinetic Control

8.19 The Diels—Alder Reaction Is a 1,4-Addition Reaction

8.20 Retrosynthetic Analysis of the Diels—Alder Reaction

8.21 Organizing What We Know About the Reactions of Organic Compounds

 

Tutorial: Drawing Resonance Contributors

 

Part Three Substitution and Elimination Reactions

 

9 Substitution Reactions of Alkyl Halides

9.1 The Mechanism for an SN2 Reaction

9.2 Factors That Affect SN2 Reactions

9.3 The Mechanism for an SN1 Reaction

9.4 Factors That Affect SN1 Reactions

9.5 Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides

9.6 Competition between SN2 and SN1 Reactions

9.7 The Role of the Solvent in SN1 and SN2 Reactions

9.8 Intermolecular Versus Intramolecular Reactions

9.9 Methylating Agents Used by Chemists Versus Those Used by Cells

 

10 Elimination Reactions of Alkyl Halides • Competition between Substitution and Elimination

10.1 The E2 Reaction

10.2 An E2 Reaction Is Regioselective

10.3 The E1 Reaction

10.4 Benzylic and Allylic Halides

10.5 Competition between E2 and E1 Reactions

10.6 E2 and E1 Reactions Are Stereoselective

10.7 Elimination from Substituted Cyclohexanes

10.8 A Kinetic Isotope Effect Can Help Determine a Mechanism

10.9 Competition between Substitution and Elimination

10.10 Substitution and Elimination Reactions in Synthesis

10.11 Designing a Synthesis II: Approaching the Problem

 

11 Reactions of Alcohols, Ethers, Amines, Thiols, and Thioethers

11.1 Nucleophilic Substitution Reactions of Alcohols: Forming Alkyl Halides

11.2 Other Methods used to Convert Alcohols into Alkyl Halides

11.3 Converting an Alcohol into a Sulfonate Ester

11.4 Elimination Reactions of Alcohols: Dehydration

11.5 Oxidation of Alcohols

11.6 Nucleophilic Substitution Reactions of Ethers

11.7 Nucleophilic Substitution Reactions of Epoxides

11.8 Arene Oxides

11.9 Amines do not Undergo Substitution or Elimination Reactions

11.10 Quaternary Ammonium Hydroxides Undergo Elimination Reactions

11.11 Thiols, Sulfides, and Sulfonium Salts

11.12 Organizing What We Know About the Reactions of Organic Compounds

 

12 Organometallic Compounds

12.1 Organolithium and Organomagnesium Compounds

12.2 The Reaction of Organolithium Compounds And Gridnard Reagents With Electrophiles

12.3 Transmetallation

12.4 Coupling Reactions

12.5 Palladium-Catalyzed Coupling Reactions

12.6 Alkene Metathesis

 

13 Radicals • Reactions of Alkanes

13.1 Alkanes Are Unreactive Compounds

13.2 The Chlorination and Bromination of Alkanes

13.3 Radical Stability Depends On the Number of Alkyl Groups Attached To the Carbon with the Unpaired Electron

13.4 The Distribution of Products Depends On Probability and Reactivity

13.5 The Reactivity Selectivity Principle

13.6 Formation of Explosive Peroxides

13.7 The Addition of Radicals to an Alkene

13.8 The Stereochemistry of Radical Substitution and Radical Addition Reactions

13.9 Radical Substitution of Benzylic and Allylic Hydrogens

13.10 Designing a Synthesis III: More Practice with Multistep Synthesis

13.11 Radical Reactions Occur In Biological Systems

13.12 Radicals and Stratospheric Ozone

 

Tutorial: Drawing Curved Arrows in Radical Systems

 

Part Four Identification of Organic Compounds

 

14 Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet/ Visible Spectroscopy

14.1 Mass Spectrometry

14.2 The Mass Spectrum • Fragmentation

14.3 Using the m/z of the Molecular Ion to Calculate the Molecular Formula

14.4 Isotopes in Mass Spectrometry

14.5 High-Resolution Mass Spectrometry Can Reveal Molecular Formulas

14.6 The Fragmentation Patterns of Functional Groups

14.7 Other Ionization Methods

14.8 Gas Chromatography–Mass Spectrometry

14.9 Spectroscopy and the Electromagnetic Spectrum

14.10 Infrared Spectroscopy

14.11 Characteristic Infrared Absorption Bands

14.12 The Intensity of Absorption Bands

14.13 The Position of Absorption Bands

14.14 The Position and Shape of an Absorption Band Is Affected By Electron Delocalization, Electron Donation and Withdrawal, and Hydrogen Bonding

14.15 The Absence of Absorption Bands

14.16 Some Vibrations Are Infrared Inactive

14.17 How to Interpret an Infrared Spectrum

14.18 Ultraviolet and Visible Spectroscopy

14.19 The Beer- Lambert Law

14.20 The Effect of Conjugation on λmax

14.21 The Visible Spectrum and Color

14.22 Some Uses of UV/ VIS Spectroscopy

 

15 NMR Spectroscopy

15.1 An Introduction to NMR Spectroscopy

15.2 Fourier Transform NMR

15.3 Shielding Causes Different Hydrogens to Show Signals at Different Frequencies

15.4 The Number of Signals in an 1H NMR Spectrum

15.5 The Chemical Shift Tells How Far the Signal Is from the Reference Signal

15.6 The Relative Positions of 1H NMR Signals

15.7 The Characteristic Values of Chemical Shifts

15.8 Diamagnetic Anisotropy

15.9 The Integration of NMR Signals Reveals the Relative Number of Protons Causing Each Signal

15.10 The Splitting of Signals Is Described by the N  1 Rule

15.11 What causes Splitting?

15.12 More Examples of 1H NMR Spectra

15.13 Coupling Constants Identify Coupled Protons

15.14 Splitting Diagrams Explain the Multiplicity of a Signal

15.15 Diastereotopic Hydrogens Are Not Chemically Equivalent

15.16 The Time Dependence of NMR Spectroscopy

15.17 Protons Bonded to Oxygen and Nitrogen

15.18 The Use of Deuterium in 1H NMR Spectroscopy

15.19 The Resolution of 1H NMR Spectra

15.20 13C NMR Spectroscopy

15.21 Dept 13C NMR Spectra

15.22 Two-Dimensional NMR Spectroscopy

15.23 NMR Used in Medicine Is Called Magnetic Resonance Imaging

15.24 X-Ray Crystallography

 

Part 5 Carbonyl Compounds

 

16 Reactions of Carboxylic Acids and Carboxylic Derivatives

16.1 The Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives

16.2 The Structures of Carboxylic Acids and Carboxylic Acid Derivatives

16.3 The Physical Properties of Carbonyl Compounds

16.4 Fatty Acids Are Long-Chain Carboxylic Acids

16.5 How Carboxylic Acids and Carboxylic Acid Derivatives React

16.6 The Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives

16.7 The General Mechanism for Nucleophilic Addition- Elimination Reactions

16.8 The Reactions of Acyl Chlorides

16.9 The Reactions of Esters

16.10 Acid-Catalyzed Ester Hydrolysis and Transesterification

16.11 Hydroxide-Ion-Promoted Ester Hydrolysis

16.12 How the Mechanism for Nucleophilic Addition-Elimination Was Confirmed

16.13 Fats and Oils are Triglycerides

16.14 Reactions of Carboxylic Acids

16.15 Reactions of Amides

16.16 Acid- Catalyzed Amide Hydrolysis and Alcoholysis

16.17 Hydroxide-Ion Promoted Hydrolysis of Amides

16.18 The Hydrolysis of an Imide: A Way to Synthesize Primary Amines

16.19 Nitriles

16.20 Acid Anhydrides

16.21 Dicarboxylic Acids

16.22 How Chemists Activate Carboxylic Acids

16.23 How Cells Activate Carboxylic Acids

 

17 Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives • Reactions of α, β- Unsaturated Carbonyl Compounds

17.1 The Nomenclature of Aldehydes and Ketones

17.2 The Relative Reactivities of Carbonyl Compounds

17.3 How Aldehydes and Ketones React

17.4 The Reactions of Carbonyl Compounds with Gringard Reagents

17.5 The Reactions of Carbonyl Compounds with Acetylide Ions

17.6 The Reactions of Aldehydes and Ketones with Cyanide Ion

17.7 The Reactions of Carbonyl Compounds with Hydride Ion

17.8 More about Reduction Reactions

17.9 Chemoselective Reactions

17.10 The Reactions of Aldehydes and Ketones with Amines

17.11 The Reactions of Aldehydes and Ketones with Water  

17.12 The Reactions of Aldehydes and Ketones with Alcohols

17.13 Protecting Groups

17.14 The Addition of Sulfur Nucleophiles

17.15 The Reactions of Aldehydes and Ketones with a Peroxyacid

17.16 The Wittig Reaction Forms an Alkene

17.17 Designing a Synthesis IV: Disconnections, Synthons, and Synthetic Equivalents

17.18 Nucleophilic Addition to α, β- Unsaturated Aldehydes and Ketones

17.19 Nucleophilic Addition to α, β- Unsaturated Carboxylic Acid Derivatives

 

18 Reactions at the α- Carbon of Carbonyl Compounds

18.1 The Acidity of an α-Hydrogen

18.2 Keto-Enol Tautomers

18.3 Keto-Enol Interconversion

18.4 Halogenation of the α-Carbon of Aldehydes and Ketones.

18.5 Halogenation of the α-Carbon of Carboxylic Acids:  The Hell-Volhard-Zelinski Reaction

18.6 Forming an Enolate Ion

18.7 Alkylating the α-Carbon of Carbonyl Compounds

18.8 Alkylating the α-Carbon Using an Enamine Intermediate

18.9 Alkylating the β-Carbon: The Michael Reaction

18.10 An Aldol Addition Forms β-Hydroxyaldehydes or β-Hydroxyketones

18.11 The Dehydration of Aldol Addition Products Forms α,β-Unsaturated Aldehydes and Ketones

18.12 A Crossed Aldol Addition

18.13 A Claisen Condensation Forms a β-Keto Ester

18.14 Other Crossed Condensations

18.15 Intramolecular Condensations And Intramolecular Aldol Additions

18.16 The Robinson Annulation

18.17 Carboxylic Acids with a Carbonyl Group at the 3-Position Can Be Decarboxylated

18.18 The Malonic Ester Synthesis: A Way to Synthesize a Carboxylic Acid

18.19 The Acetoacetic Ester Synthesis: A Way Synthesize a Methyl Ketone

18.20 Designing a Synthesis V:  Making New Carbon-Carbon Bonds

18.21 Reactions at the a-Carbon in Biological Systems

18.22 Organizing What We Know About the Reactions of Organic Compounds

 

Part 5

 

19 Reactions Of Benzene And Substituted Benzenes

19.1 The Nomenclature of Monosubstituted Benzenes

19.2 How Benzene Reacts

19.3 The General Mechanism for Electrophilic Aromatic Substitution Reactions

19.4 The Halogenation of Benzene

19.5 The Nitration of Benzene

19.6 The Sulfonation of Benzene

19.7 The Friedel-Crafts Acylation of Benzene

19.8 The Friedel-Crafts Alkylation of Benzene

19.9 The Alkylation of Benzene by Acylation-Reduction

19.10 Using Coupling Reactions to Alkylate Benzene

19.11 It Is Important to Have More than One Way to Carry Out a Reaction

19.12 How Some Substituents on a Benzene Ring Can Be Chemically Changed

19.13 The Nomenclature of Disubstituted and Polysubstituted Benzenes

19.14 The Effect of Substituents on Reactivity

19.15 The Effect of Substituents on Orientation

19.16 The Effect of Substituents on pKa

19.17 The Ortho/Para Ratio

19.18 Additional Considerations Regarding Substituent Effects

19.19 Designing a Synthesis VI:  Synthesis of Monosubstituted and Disubstituted Benzenes  

19.20 The Synthesis of Trisubstituted Benzenes

19.21 The Synthesis of Substituted Benzenes Using Arenediazonium Salts

19.22 The Arenediazonium Ion as an Electrophile

19.23 The Mechanism for the Reaction of Amines with Nitrous Acid

19.24 Nucleophilic Aromatic Substitution: An Addition-Elimination Reaction

19.25 Designing a Synthesis VII: The Synthesis of Cyclic Compounds

 

Tutorial: Synthesis and Retrosynthetic Analysis

 

20 More About Amines· Reactions of Heterocyclic Compounds

20.1 More About Amine Nomenclature

20.2 More About the Acid-Base Properties of Amines

20.3 Amines React as Bases and as Nucleophiles

20.4 The Synthesis of Amines

20.5 Aromatic Five-Membered Ring Heterocycles

20.6 Aromatic Six-Membered-Ring Heterocycles  

20.7 Some Amine Heterocycles Have Important Roles in Nature

20.8 Organizing What We Know About the Reactions of Organic Compounds   

 

Part 7: Bioorganic Compounds

 

21 The Organic Chemistry Of Carbohydrates

21.1 The Classification of Carbohydrates

21.2 The D and L Notation

21.3 The Configurations of the Aldoses

21.4 The Configurations of the Ketoses

21.5 The Reactions of Monosaccharides in Basic Solutions

21.6 The Oxidation-Reduction Reactions of Monosaccharides

21.7 Lengthening the Chain: The Kiliani—Fischer Synthesis

21.8 Shortening the Chain: The Wohl Degradation

21.9 The Stereochemistry of Glucose: The Fischer Proof  

21.10 Monosaccharides Form Cyclic Hemiacetals

21.11 Glucose Is the Most Stable Aldohexose

21.12 Formation of Glycosides

21.13 The Anomeric Effect

21.14 Reducing and Nonreducing Sugars

21.15 Disaccharides

21.16 Polysaccharides

21.17 Some Naturally Occurring Products Derived from Carbohydrates

21.18 Carbohydrates on Cell Surfaces

21.19 Artificial Sweeteners

 

22 The Organic Chemistry Of Amino Acids, Peptides, And Proteins 22.1 Nomenclature of Amino Acids

22.2 The Configuration of the Amino Acids

22.3 The Acid-Base Properties of Amino Acids

22.4 The Isoelectric Point

22.5 Separating Amino Acids

22.6 The Synthesis of Amino Acids

22.7 The Resolution of Racemic Mixtures of Amino Acids

22.8 Peptide Bonds and Disulfide Bonds

22.9 Some Interesting Peptides

22.10 The Strategy of Peptide Bond Synthesis: N-Protection and C-Activation

22.11 Automated Peptide Synthesis

22.12 An Introduction to Protein Structure

22.13 How to Determine the Primary Structure of a Polypeptide or Protein

22.14 Secondary Structure

22.15 Tertiary Structure

22.16 Quaternary Structure

22.17 Protein Denaturation

 

23 Catalysis in Organic Reactions and in Enzymatic Reactions

23.1 Catalysis in Organic Reactions  

23.2 Acid Catalysis

23.3 Base Catalysis

23.4 Nucleophilic Catalysis

23.5 Metal-Ion Catalysis

23.6 Intramolecular Reactions  

23.7 Intramolecular Catalysis

23.8 Catalysis in Biological Reactions  

23.9 The Mechanisms for Two Enzyme-Catalyzed Reactions That Are Reminiscent of Acid-Catalyzed Amide Hydrolysis

23.10 The Mechanism for an Enzyme-Catalyzed Reaction that Involves Two Sequential SN2 Reactions

23.11 The Mechanism for an Enzyme-Catalyzed Reaction that is Reminiscent of the Base-Catalyzed Enediol Rearrangement

23.12 The Mechanism for an Enzyme-Catalyzed Reaction that Is Reminiscent of the Aldol Addition Reaction

 

24 The Organic Chemistry Of The Coenzymes–Compounds Derived From Vitamins

24.1 The Vitamin Needed for Many Redox Reactions: Niacin   

24.2 Another Vitamin Used in Redox Reactions: Riboflavin   

24.3 The Vitamin Needed for Acyl Group Transfer: Vitamin B1

24.4 The Vitamin Needed for Carboxylation of an a-Carbon: Vitamin H  

24.5 The Vitamin Needed for Amino Acid Transformations: Vitamin B6  

24.6 The Vitamin Needed for Certain Isomerizations: Vitamin B12

24.7 The Vitamin Needed for One-Carbon Transfer: Folate

24.8 The Vitamin Needed for Carboxylation of Glutamate: Vitamin K  

 

25 The Organic Chemistry of the Metabolic Pathways • Terpene Biosynthesis

25.1 ATP Is Used for Phosphoryl Transfer Reactions

25.2 ATP Activates A Compound by Giving it a Good Leaving Group

25.3 Why ATP Is Kinetically Stable in a Cell

25.4 The “High-Energy” Character of Phosphoanhydride Bonds

25.5 The Four Stages of Catabolism

25.6 The Catabolism of Fats

25.7 The Catabolism of Carbohydrates

25.8 The Fate of Pyruvate

25.9 The Catabolism of Proteins

25.10 The Citric Acid Cycle

25.11 Oxidative Phosphorylation

25.12 Anabolism

25.13 Gluconeogenesis

25.14 Regulating Metabolic Pathways

25.15 Amino Acid Biosynthesis

25.16 Terpenes Contain Carbon Atoms in Multiples of Five

25.17 How Terpenes Are Biosynthesized

25.18 How Nature Synthesizes Cholesterol

 

26 The Chemistry of the Nucleic Acids

26.1 Nucleosides and Nucleotides

26.2 Other Important Nucleotides

26.3 Nucleic Acids Are Composed of Nucleotide Subunits

26.4 Why DNA Does Not Have A 2’ —OH Group

26.5 The Biosynthesis of SNA Is Called Replication

26.6 DNA and Heredity

26.7 The Biosynthesis of RNA Is Called Transcription

26.8 There Are Three Kinds of RNA

26.9 The Biosynthesis of Proteins Is Called Translation

26.10 Why DNA Contains Thymine Instead of Uracil

26.11 Antiviral Drugs

26.12 The Polymerase Chain Reaction (PCR)

26.13 Genetic Engineering

26.14 The Laboratory Synthesis of DNA Strands

 

Part 8 Special Topics in Organic Chemistry

 

27 Synthetic Polymers

27.1 There Are Two Major Classes of Syntheric Polymers

27.2 Chain-Growth Polymers

27.3 Stereochemistry of Polymerization • Ziegler-Natta Catalysts

27.4 Polymerization of Dienes • The Manufacture of Rubber

27.5 Copolymers

27.6 Step-Growth Polymers

27.7 Classes of Step-Growth Polymers

27.8 Physical Properties of Polymers

27.9 Recycling Polymers

27.10 Biodegradable Polymers

 

28 Pericyclic Reactions

28.1 There Are Three Kinds of Pericyclic Reactions

28.2 Molecular Orbitals and Orbital Symmetry

28.3 Electrocyclic Reactions

28.4 Cycloaddition Reactions

28.5 Sigmatropic Rearrangements

28.6 Pericyclic Reactions in Biological Systems

28.7 Summary of the Selection Rules for Pericyclic Reactions

 

Appendix I Values

Appendix II Derivations of Rate Laws

Appendix III Summary of Methods Used to Synthesize a Particular Functional Group

Appendix IV Summary of Methods Employed to Form Carbon-Carbon Bonds

 

Answers to Selected Problems

Glossary

Photo Credits

Index