Organic Chemistry Maitland Jones Jr., Steven A. Fleming really hard course

Organic Chemistry, Fifth Edition
	Brief Contents
	Contents
	Selected Applications
	Organic Reaction Animations
	Preface to the Fifth Edition
	Introduction
Chapter
1:  Atoms and Molecules; Orbitals and Bonding
	1.1:  Preview
	1.2:  Atoms and Atomic Orbitals
	1.3:  Covalent Bonds and Lewis Structures
	1.4:  Formal Charges
	1.5:  Resonance Forms and the Curved Arrow Formalism
	1.6:  Hydrogen (H2): Molecular Orbitals
	1.7:  Bond Strength
	1.8:  An Introduction to Reactivity: Acids and Bases
	1.9:  Special Topic: Quantum Mechanics and Babies
	1.10: Summary
	1.11: Additional Problems
Chapter 2:  Alkanes
	2.1:  Preview
	2.2:  Hybrid Orbitals: Making a Model for Methane
	2.3:  The Methyl Group (CH3) and Methyl Compounds (CH3X)
	2.4:  The Methyl Cation (+CH3), Anion (-:CH3), and Radial (.CH3)
	2.5:  Ethane (C2H6), Ethyl Compounds (C2H5X), and Newman Projections
	2.6:  Structure Drawings
	2.7:  Propane (C3H8) and Propyl Compounds (C3H7X)
	2.8:  Butanes (C4H10), Butyl Compounds (C4H9X), and Comformational Analysis
	2.9:  Pentanes (C5H12) and Pentyl Compounds (C5H11X)
	2.10: The Naming Conventions for Alkanes
	2.11: Drawing Isomers
	2.12: Cycloalkanes
	2.13: Physical Properties of Alkanes and Cycloalkanes
	2.14: Nuclear Magnetic Resonance Spectra of Alkanes
	2.15: Acids and Bases Revisited: More Chemical Reactions
	2.16: Special Topic: Alkanes as Biomolecules
	2.17: Summary
	2.18: Additional Problems
Chapter 3:  Alkenes and Alkynes
	3.1:  Preview
	3.2:  Alkenes: Structure and Bonding
	3.3:  Derivatives and Isomers of Alkenes
	3.4:  Nomenclature
	3.5:  The Cahn-Ingold-Prelog Priority System
	3.6:  Relative Stability of Alkenes: Heats of Formation
	3.7:  Double Bonds in Rings
	3.8:  Physical Properties of Alkenes
	3.9:  Alkynes: Structure and Bonding
	3.10: Relative Stability of Alkynes: Heats of Formation
	3.11: Derivatives and Isomers of Alkynes
	3.12: Triple Bonds in Rings
	3.13: Physical Properties of Alkynes
	3.14: Acidity of Alkynes
	3.15: Molecular Formulas and Degrees of Unsaturation
	3.16: An Introduction to Addition Reactions of Alkenes and Alkynes
	3.17: Mechanism of the Addition of Hydrogen Halides to Alkenes
	3.18: The Energetics of the Addition Reaction: Energy Diagrams
	3.19: The Regiochemistry of the Addition Reaction
	3.20: A Catalyzed Addition to Alkenes: Hydration
	3.21: Synthesis: A Beginning
	3.22: Special Topic: Alkenes and Biology
	3.23: Summary
	3.24: Additional Problems
Chapter 4:  Stereochemistry
	4.1:  Preview
	4.2:  Chirality
	4.3:  The (R/S) Convention
	4.4:  Properties of Enantiomers: Physical Differences
	4.5:  The Physical Basis of Optical Activity
	4.6:  Properties of Enantiomers: Chemical Differences
	4.7:  Interconversion of Enantiomers by Rotation about a Single Bond: gauche-Butane
	4.8:  Properties of Diastereomers: Molecules Containing More than One Stereogenic Atom
	4.9:  Resolution, a Method of Separating Enantiomers from Each Other
	4.10: Determination of Absolute Configuration [(R) or (S)]
	4.11: Stereochemical Analysis of Ring Compounds (a Beginning)
	4.12: Summary of Isomerism
	4.13: Special Topic: Chirality without "Four Different Groups Attached to One Carbon"
	4.14: Special Topic: Stereochemistry in the Real World: Thalidomide, the Consequences of Being Wrong-Handed
	4.15: Summary
	4.16: Additional Problems
Chapter 5:  Rings
	5.1:  Preview
	5.2:  Rings and Strain
	5.3:  Quantitative Evaluation of Strain Energy
	5.4:  Stereochemistry of Cyclohexane: Conformational Analysis
	5.5:  Monosubstituted Cyclohexanes
	5.6:  Disubstituted Ring Compounds
	5.7:  Bicyclic Compounds
	5.8:  Special Topic: Polycyclic Systems
	5.9:  Special Topic: Adamantanes in Materials and Biology
	5.10: Summary
	5.11: Additional Problems
Chapter 6:  Substituted Alkanes: Alkyl Halides, Alcohols, Amines, Ethers, Thiols, and Thioethers
	6.1:  Preview
	6.2:  Nomenclature of Substituted Alkanes
	6.3:  Structure of Substituted Alkanes
	6.4:  Properties of Substituted Alkanes
	6.5:  Solubility
	6.6:  Formation of Substituted Alkanes
	6.7:  A Reaction of Alkyl Halides: Synthesis of Alkanes
	6.8:  Special Topic: Sulfur Compounds
	6.9:  Special Topic: Crown Ethers
	6.10: Summary
	6.11: Additional Problems
Chapter 7:  Substitution Reactions: The SN2 and SN1 Reactions
	7.1:  Preview
	7.2:  Review of Lewis Acids and Bases
	7.3:  Reactions of Alkyl Halides: The Substitution Reaction
	7.4:  Equilibrium and Reaction Rates, Thermodynamics and Kinetics
	7.5:  Substitution, Nucleophilic, Bimolecular: The SN2 Reaction
	7.6:  The SN2 Reaction in Biochemistry
	7.7:  Substitution, Nucleophilic, Unimolecular: The SN1 Reaction
	7.8:  Summary and Overview of the SN2 and SN1 Reactions
	7.9:  What Can We Do with These Reactions? How to Do Organic Synthesis
	7.10: Summary
	7.11: Additional Problems
Chapter 8:  Elimination Reactions: The E1 and E2 Reactions
	8.1:  Preview
	8.2:  The Unimolecular Reaction: E1
	8.3:  The Bimolecular Elimination Reaction: E2
	8.4:  Transition States: Thermodynamics versus Kinetics
	8.5:  Rearrangements of Carbocations
	8.6:  Special Topic: Other Eliminations
	8.7:  Special Topic: Enzymes and Reaction Rates
	8.8:  Special Topic: Why Are Rearrangements of Carbocations Fast?
	8.9:  Summary
	8.10: Additional Problems
Chapter 9:  Analytical Chemistry: Spectroscopy
	9.1:  Preview
	9.2:  Chromatography
	9.3:  Mass Spectrometry
	9.4:  Ultraviolet/Visible Spectroscopy
	9.5:  Infrared Spectroscopy
	9.6:  1H Nuclear Magnetic Resonance Spectroscopy
	9.7:  NMR Measurements
	9.8:  Special Topic: More-Complicated NMR Spectra
	9.9:  13C NMR Spectroscopy
	9.10: Problem Solving: How to Use Spectroscopy to Determine Structure
	9.11: Special Topic: Dynamic NMR
	9.12: Summary
	9.13: Additional Problems
Chapter 10: Electrophilic Additions to Alkenes
	10.1:  Preview
	10.2:  Mechanism of the Electrophilic Addition of Hydrogen Halides to Alkenes - Hydrohalogenation
	10.3:  Effects of Resonance on Regiochemistry
	10.4:  Brief Review of Resonance
	10.5:  Resonance and the Stability of Carbocations
	10.6:  Inductive Effects on Electrophilic Addition Reactions
	10.7:  More on Rearrangements of Carbocations
	10.8:  Mechanism of the Electrophilic Addition of Acid and Water to Alkenes - Hydration
	10.9:  Mechanism of Dimerization and Polymerization of Alkenes
	10.10: Mechanism of Hydroboration of Alkenes
	10.11: Hydroboration in Synthesis: Alcohol Formation
	10.12: Special Topic: Rearrangements in Biological Processes
	10.13: Summary
	10.14: Additional Problems
Chapter 11: More Additions to p Bonds
	11.1:  Preview
	11.2:  Electrophilic Addition of X2: Halogenation
	11.3:  Electrophilic Addition of Mercury: Oxymercuration
	11.4:  Electrophilic Addition of Oxygen: Epoxidation
	11.5:  Special Topic: Additions of Carbenes - Cyclopropane Synthesis
	11.6:  Dipolar Addition: Ozonolysis and Dihydroxylation
	11.7:  Hydrohalogenation of Alkynes
	11.8:  Hydration of Alkynes
	11.9:  Hydroboration of Alkynes
	11.10: Reduction by Addition of H2: Hydrogenation
	11.11: Reduction of Alkynes by Sodium in Ammonia
	11.12: Special Topic: Three-Membered Rings in Biochemistry
	11.13: Summary
	11.14: Additional Problems
Chapter 12: Radical Reactions
	12.1:  Preview
	12.2:  Formation and Simple Reactions of Radicals
	12.3:  Structure and Stability of Radicals
	12.4:  Radical Addition to Alkenes
	12.5:  Other Radical Addition Reactions
	12.6:  Radical-Initiated Addition of HBr to Alkynes
	12.7:  Photohalogenation
	12.8:  Allylic Halogenation: Synthetically Useful Reactions
	12.9:  Special Topic: Rearrangements (and Non-rearrangements) of Radicals
	12.10: Special Topic: Radicals in Our Bodies; Do Free Radicals Age Us?
	12.11: Summary
	12.12: Additional Problems
Chapter 13: Dienes and the Allyl System: 2p Orbitals in Conjugation
	13.1:  Preview
	13.2:  Allenes
	13.3:  Related Systems: Ketenes and Cumulenes
	13.4:  Allenes as Intermediates in the Isomerization of Alkynes
	13.5:  Conjugated Dienes
	13.6:  The Physical Consequences of Conjugation
	13.7:  The Chemical Consequences of Conjugation: Additional Reactions of Conjugated Dienes
	13.8:  Thermodynamic and Kinetic Control of Addition Reactions
	13.9:  The Allyl System: Three Overlapping 2p Orbitals
	13.10: The Diels-Adler Reaction of Conjugated Dienes
	13.11: Special Topic: Biosynthesis of Terpenes
	13.12: Special Topic: Steroid Biosynthesis
	13.13: Summary
	13.14: Additional Problems
Chapter 14: Aromaticity
	14.1:  Preview
	14.2:  The Structure of Benzene
	14.3:  A Resonance Picture of Benzene
	14.4:  The Molecular Orbital Picture of Benzene
	14.5:  Quantitative Evaluations of Resonance Stabilization in Benzene
	14.6:  A Generalization of Aromaticity: Huckel's 4n + 2 Rule
	14.7:  Substituted Benzenes
	14.8:  Physical Properties of Substituted Benzenes
	14.9:  Heterobenzenes and Other Heterocyclic Aromatic Compounds
	14.10: Polycyclic Aromatic Compounds
	14.11: Special Topic: The Bio-Downside, the Mechanism of Carcinogenesis by Polycyclic Aromatic Hydrocarbons
	14.12: The Benzyl Group and Its Reactivity
	14.13: Introduction to the Chemistry of Benzene
	14.14: Summary
	14.15: Additional Problems
Chapter 15: Substitution Reactions of Aromatic Compounds
	15.1:  Preview
	15.2:  Hydrogenation of Aromatic Compounds
	15.3:  Electrophilic Aromatic Substitution Reactions
	15.4:  Substitution Reactions We Can Do Using Nitrobenzene
	15.5:  Electrophilic Aromatic Substitution of Heteroaromatic Compounds
	15.6:  Disubstituted Benzenes: Ortho, Meta, and Para Substitution
	15.7:  Synthesis of Polysubstituted Benzenes
	15.8:  Nucleophilic Aromatic Substitution
	15.9:  Special Topic: Benzyne
	15.10: Special Topic: Diels-Alder Reactions
	15.11: Special Topic: Stable Carbocations in "Superacid"
	15.12: Special Topic: Biological Synthesis of Aromatic Rings; Phenylalanine
	15.13: Summary
	15.14: Additional Problems
Chapter 16: Carbonyl Chemistry 1: Addition Reactions
	16.1:  Preview
	16.2:  Structure of the Carbon-Oxygen Double Bond
	16.3:  Nomenclature of Carbonyl Compounds
	16.4:  Physical Properties of Carbonyl Compounds
	16.5:  Spectroscopy of Carbonyl Compounds
	16.6:  Reactions of Carbonyl Compounds: Simple Reversible Additions
	16.7:  Equilibrium in Addition Reactions
	16.8:  Other Addition Reactions: Additions of Cyanide and Bisulfite
	16.9:  Addition Reactions Followed by Water Loss: Acetal Formation
	16.10: Protecting Groups in Synthesis
	16.11: Addition Reactions of Nitrogen Bases: Imine and Enamine Formation
	16.12: Organometallic Reagents
	16.13: Irreversible Addition Reactions: A General Synthesis of Alcohols
	16.14: Oxidation of Alcohols to Carbonyl Compounds
	16.15: Retrosynthetic Alcohol Synthesis
	16.16: Oxidation of Thiols and Other Sulfur Compounds
	16.17: The Wittig Reaction
	16.18: Special Topic: Biological Oxidation
	16.19: Summary
	16.20: Additional Problems
Chapter 17: Carboxylic Acids
	17.1:  Preview
	17.2:  Nomenclature and Properties of Carboxylic Acids
	17.3:  Structure of Carboxylic Acids
	17.4:  Infrared and Nuclear Magnetic Resonance Spectra of Carboxylic Acids
	17.5:  Acidity and Basicity of Carboxylic Acids
	17.6:  Syntheses of Carboxylic Acids
	17.7:  Reactions of Carboxylic Acids
	17.18:  Special Topic: Carboxylic Acids in Nature
	17.9:  Summary
	17.10: Additional Problems
Chapter 18: Derivatives of Carboxylic Acids: Acyl Compounds
	18.1:  Preview
	18.2:  Nomenclature
	18.3:  Physical Properties and Structures of Acyl Compounds
	18.4:  Acidity and Basicity of Acyl Compounds
	18.5:  Spectral Characteristics
	18.6:  Reactions of Acid Chlorides: Synthesis of Acyl Compounds
	18.7:  Reactions of Anhydrides
	18.8:  Reactions of Esters
	18.9:  Reactions of Amides
	18.10: Reactions of Nitriles
	18.11: Reactions of Ketenes
	18.12: Special Topic: Other Synthetic Routes to Acid Derivatives
	18.13: Special Topic: A Family of Concerted Rearrangements of Acyl Compounds
	18.14: Summary
	18.15: Additional Problems
Chapter 19: Carbonyl Chemistry 2: Reactions at the a Position
	19.1:  Preview
	19.2:  Many Carbonyl Compounds Are Weak Bronsted Acids
	19.3:  Racemization of Enols and Enolates
	19.4:  Halogenation in the a Position
	19.5:  Alkylation in the a Position
	19.6:  Addition of Carbonyl Compounds to the a Position: The Aldol Condensation
	19.7:  Reactions Related to the Aldol Condensation
	19.8:  Addition of Acid Derivatives to the a Position: The Claisen Condensation
	19.9:  Variations on the Claisen Condensation
	19.10: Special Topic: Forward and Reverse Claisen Condensations in Biology
	19.11: Condensation Reactions in Combination
	19.12: Special Topic: Alkylation of Dithianes
	19.13: Special Topic: Amines in Condensation Reactions, the Mannich Reaction
	19.14: Special Topic: Carbonyl Compounds without a Hydrogens
	19.15: Special Topic: The Aldol Condensation in the Real World, an Introduction to Modern Synthesis
	19.16: Summary
	19.17: Additional Problems
Chapter 20: Carbohydrates
	20.1:  Preview
	20.2:  Nomenclature and Structure of Carbohydrates
	20.3:  Formation of Carbohydrates
	20.4:  Reactions of Carbohydrates
	20.5:  Special Topic: The Fischer Determination of the Structure of D-Glucose (and the 15 Other Aldohexoses)
	20.6:  Special Topic: An Introduction to Disaccharides and Polysaccharides
	20.7:  Summary
	20.8:  Additional Problems
Chapter 21: Special Topic: Bioorganic Chemistry
	21.1:  Preview
	21.2:  Lipids
	21.3:  Formation of Neutral and Acidic Biomolecules
	21.4:  Alkaloids
	21.5:  Formation of Basic Biomolecules: Amine Chemistry
	21.6:  Summary
	21.7:  Additional Problems
Chapter 22: Special Topic: Amino Acids and Polyamino Acids (Peptides and Proteins)
	22.1:  Preview
	22.2:  Amino Acids
	22.3:  Reactions of Amino Acids
	22.4:  Peptide Chemistry
	22.5:  Nucleosides, Nucleotides, and Nucleic Acids
	22.6:  Summary
	22.7:  Additional Problems
Chapter 23: Special Topic: Reactions Controlled by Orbital Symmetry
	23.1:  Preview
	23.2:  Concerted Reactions
	23.3:  Electrocyclic Reactions
	23.4:  Cycloaddition Reactions
	23.5:  Sigmatropic Shift Reactions
	23.6:  The Cope Rearrangement
	23.7:  A Molecule with a Fluxional Structure
	23.8:  How to Work Orbital Symmetry Problems
	23.9:  Summary
	23.10: Additional Problems
Chapter 24: Special Topic: Intramolecular Reactions and Neighboring Group Participation
	24.1:  Preview
	24.2:  Heteroatoms as Neighboring Groups
	24.3:  Neighboring p Systems
	24.4:  Single Bonds as Neighboring Groups
	24.5:  Coates' Cation
	24.6:  Summary
	24.7:  Additional Problems
Glossary
Credits
Index
Copyright
Title Page
Dedication
Contents
Chapter 1: ‘I’m thinking’ – Oh, but are you?
Chapter 2: Renegade perception
Chapter 3: The Pushbacker sting
Chapter 4: ‘Covid’: The calculated catastrophe
Chapter 5: There is no ‘virus’
Chapter 6: Sequence of deceit
Chapter 7: War on your mind
Chapter 8: ‘Reframing’ insanity
Chapter 9: We must have it? So what is it?
Chapter 10: Human 2.0
Chapter 11: Who controls the Cult?
Chapter 12: Escaping Wetiko
Postscript
Appendix: Cowan-Kaufman-Morell Statement on Virus Isolation
Bibliography
Index