Athabasca University
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- Chemistry 350: Organic Chemistry I
- Chapter 1: Structure and Bonding
- 1.0 Introduction
- 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 The Nature of 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 The Nature of Chemical Bonds: Molecular Orbital Theory
- 1.12 Drawing Chemical Structures
- Chapter 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 pKa Values
- 2.10 Organic Acids and Organic Bases
- 2.11 Acids and Bases: The Lewis Definition
- 2.12 Noncovalent Interactions Between Molecules
- 2.13 Molecular Models
- Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry
- Chapter 4: Organic Compounds: Cycloalkanes and their Stereochemistry
- Chapter Objectives
- 4.1 Naming Cycloalkanes
- 4.2 Cis-Trans Isomerism in Cycloalkanes
- 4.3 Stability of Cycloalkanes - Ring Strain
- 4.4 Conformations of Cycloalkanes
- 4.5 Conformations of Cyclohexane
- 4.6 Axial and Equatiorial Bonds in Cyclohexane
- 4.7 Conformations of Monosubstituted Cyclohexanes
- 4.8 Conformations of Disubstituted Cyclohexanes
- 4.9 Conformations of Polycyclic Molecules
- Chapter 5: Stereochemistry at Tetrahedral Centres
- Chapter Objectives
- 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
- Chapter 6: An Overview of Organic Reactions
- Chapter Objectives
- 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
- Chapter 7: Alkenes: Structure and Reactivity
- Chapter Objectives
- 7.0 Introduction
- 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 Sequence Rules: 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
- Chapter 8: Alkenes: Reactions and Synthesis
- Chapter Objectives
- 8.1 Preparation of 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 Stereochemistry of Reactions: Addition of \(H_2O\) to an Achiral Alkene
- 8.13 Stereochemistry of Reactions: Addition of \(H_2O\) to a Chiral Alkene
- Chapter 9: Alkynes: An Introduction to Organic Synthesis
- Chapter Objectives
- 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
- 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
- Chapter 10: Organohalides
- Chapter Objectives
- 10.0 Introduction
- 10.1 Names and Properties 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
- Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
- Chapter Objectives
- 11.0 Introduction
- 11.1 The Discovery of Nucleophilic Substitution Reactions
- 11.2 The \(S_{N}2\) Reaction
- 11.3 Characteristics of the \(S_{N}2\) Reaction
- 11.4 The \(S_{N}1\) Reaction
- 11.5 Characteristics of the \(S_{N}1\) Reaction
- 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
- 11.11 Biological Elimination Reactions
- 11.12 A Summary of Reactivity: \(S_{N}1\), \(S_{N}2\), E1, E1cB, and E2
- Chapter 12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy
- Chapter Objectives
- 12.0 Introduction
- 12.1 Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments
- 12.2 Interpreting Mass Spectra
- 12.3 Mass Spectrometry of Some Common Functional Groups
- 12.4 Mass Spectrometry in Biological: 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
- Chapter 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
- Chapter Objectives
- 13.1 Nuclear Magnetic Resonance Spectroscopy
- 13.2 The Nature of NMR Absorptions
- 13.3 Chemical Shifts
- 13.4 \(^{13}C\) NMR Spectroscopy: Signal Averaging and FT-NMR
- 13.5 Characteristics of \(^{13}C\) NMR Spectroscopy
- 13.6 DEPT \(^{13}C\) NMR Spectroscopy
- 13.7 Uses of \(^{13}C\) NMR Spectroscopy
- 13.8 \(^1H\) NMR Spectroscopy and Proton Equivalence
- 13.9 Chemical Shifts in \(^1H\) NMR Spectroscopy
- 13.10 Integration of \(^1H\) NMR Absorptions: Proton Counting
- 13.11 Spin-Spin Splitting in \(^1H\) NMR Spectra
- 13.12 More Complex Spin-Spin Splitting Patterns
- 13.13 Uses of \(^1H\) NMR Spectroscopy
- Chapter 14: Conjugated Compounds and Ultraviolet Spectroscopy
- Chapter Objectives
- 14.0 Introduction
- 14.1 Stability of Conjugated Dienes: Molecular Orbital Theory
- 14.2 Electrophilic Additions to Conjugated Dienes: Allylic Carbocations
- 14.3 Kinetic vs. Thermodynamic Control of Reactions
- 14.4 The Diels-Alder Cycloaddition Reaction
- 14.5 Characteristics of the Diels-Alder Reaction
- 14.6 Diene Polymers: Natural and Synthetic Rubbers
- 14.7 Structure Determination in Conjugated Systems: Ultraviolet Spectroscopy
- 14.8 Interpreting Ultraviolet Spectra: The Effect of Conjugation
- 14.9 Conjugation, Color, and the Chemistry of Vision
- Chapter 15: Benzene and Aromaticity
- Chapter Objectives
- 15.0 Introduction
- 15.1 Sources and Names of Aromatic Compounds
- 15.2 Structure and Stability of Benzene
- 15.3 Aromaticity and the Huckel 4n + 2 Rule
- 15.4 Aromatic Ions
- 15.5 Aromatic Heterocycles: Pyridine and Pyrrole
- 15.6 Polycyclic Aromatic Compounds
- 15.7 Spectroscopy of Aromatic Compounds
- Chapter 16: Chemistry of Benzene: Electrophilic Aromatic Substitution
- Chapter Objectives
- 16.0 Introduction
- 16.1 Electrophilic Aromatic Substitution Reactions: Bromination
- 16.2 Other Aromatic Substitutions
- 16.3 Alkylation and Acylation of Aromatic Rings: The Friedel-Crafts Reaction
- 16.4 Substituent Effects in Substituted Aromatic Rings
- 16.5 An Explanation of Substituent Effects
- 16.6 Trisubstituted Benzenes: Additivity of Effects
- 16.7: Nucleophilic Aromatic Substitution
- 16.8 Benzyne
- 16.9 Oxidation of Aromatic Compounds
- 16.10 Reduction of Aromatic Compounds
- 16.11 Synthesis of Polysubstituted Benzenes
- Chapter 1: Structure and Bonding
- Chemistry 360: Organic Chemistry II
- Chapter 17: Alcohols and Phenols
- Chapter Objectives
- 17.0 Introduction
- 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
- 17.5 Alcohols from Reaction of Carbonyl Compounds: Grignard Reagents
- 17.6 Reactions of Alcohols
- 17.7 Oxidation of Alcohols
- 17.8 Protection of Alcohols
- 17.9 Phenols and Their Uses
- 17.10 Reactions of Phenols
- 17.11 Spectroscopy of Alcohols and Phenols
- Chapter 18: Ethers and Epoxides; Thiols and Sulfides
- Chapter Objectives
- 18.0 Introduction
- 18.1 Names and Properties of Ethers
- 18.2 Synthesis of Ethers
- 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
- 18.7 Crown Ethers
- 18.8 Thiols and Sulfides
- 18.9 Spectroscopy of Ethers
- Chapter 18 - Affix: A Preview of Carbonyl Compounds
- Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions
- Chapter Objectives
- 19.1 Naming Aldehydes and Ketones
- 19.2 Preparing Aldehydes and Ketones
- 19.3 Oxidation of Aldehydes and Ketones
- 19.4 Nucleophilic Addition Reactions of Aldehydes and Ketones
- 19.5 Nucleophilic Addition of \(H_2O\): Hydration
- 19.6 Nucleophilic Addition of HCN: Cyanohydrin Formation
- 19.7 Nucleophilic Addition of Grignard Reagents and Hydride Reagents: Alcohol Formation
- 19.8 Nucleophilic Addition of Amines: Imine and Enamine Formation
- 19.9 Nucleophilic Addition of Hydrazin - 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 \(\alpha\), \(\beta\)-unsaturated Aldehydes and Ketones
- 19.14 Spectroscopy of Aldehydes and Ketones
- Chapter 20: Carboxylic Acids and Nitriles
- Chapter Objectives
- 20.0 Introduction
- 20.1 Naming Carboxylic Acids and Nitriles
- 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
- 20.6 Reactions of Carboxylic Acids: An Overview
- 20.7 Chemistry of Nitriles
- 20.8 Spectroscopy of Carboxylic Acids and Nitriles
- Chapter 21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
- Chapter Objectives
- 21.0 Introduction
- 21.1 Naming Carboxylic Acid Derivatives
- 21.2 Nucleophilic Acyl Substitution Reactions
- 21.3 Nucleophilic Acyl Substitution Reactions of Carboxylic Acids
- 21.4 Chemistry of Acid Halides
- 21.5 Chemistry of Acid Anhydrides
- 21.6 Chemistry of Esters
- 21.7 Chemistry of Amides
- 21.8 Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives
- 21.9 Polyamides and Polyesters: Step-Growth Polymers
- 21.10 Spectroscopy of Carboxylic Acid Derivatives
- Chapter 22: Carbonyl Alpha-Substitution Reactions
- Chapter Objectives
- 22.0 Introduction
- 22.1 Keto-Enol Tautomerism
- 22.2 Reactivity of Enols: The Mechanism of Alpha-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
- Chapter 23: Carbonyl Condensation Reactions
- Chapter Objectives
- 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
- Chapter 24: Amines and Heterocycles
- Chapter Objectives
- 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
- 24.7 Reactions of Amines
- 24.8 Reactions of Arylamines
- 24.9 Heterocyclic Amines
- 24.10 Spectroscopy of Amines
- Chapter 25: Biomolecules: Carbohydrates
- Chapter Objectives
- 25.0 Introduction
- 25.1 Classification of Carbohydrates
- 25.2 Depicting Carbohydrate Stereochemistry: Fischer Projections
- 25.3 D, L Sugars
- 25.4 Configurations of Aldoses
- 25.5 Cyclic Structures of Monosaccharides: Anomers
- 25.6 Reactions of Monosaccharides
- 25.7 The Eight Essential Monosaccharides
- 25.8 Disaccharides
- 25.9 Polysaccharides and Their Synthesis
- 25.10 Other Important Carbohydrates
- 25.11 Cell-Surface Carbohydrates and Influenza Viruses
- Chapter 26: Biomolecules: Amino Acids, Peptides, and Proteins
- Chapter Objectives
- 26.0 Introduction
- 26.1 Structures of Amino Acids
- 26.2 Amino Acids, the Henderson-Hasselbalch Equation, and Isoelectric Points
- 26.3 Synthesis of Amino Acids
- 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 Technique
- 26.9 Protein Structure
- 26.10 Enzymes and Coenzymes
- 26.11 How do Enzymes Work? Citrate Synthase
- Chapter 27: Biomolecules - Lipids
- Chapter 28: Biomolecules - Nucleic Acids
- Chapter 17: Alcohols and Phenols
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