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Athabasca University Chemistry 350 Organic Chemistry I

CHEM 350 deals with the chemistry of carbon compounds through a study of the characteristic reactions of the common functional groups. Particular emphasis is placed on the study of reaction mechanisms in an attempt to show similarities between apparently unrelated reactions. The importance of stereochemistry is stressed throughout the course. The course also includes an introduction to the use of spectroscopy in the analysis of organic compounds.

Chemistry

Tác giả: Dietmar Kennepohl
Nhà xuất bản: Athabasca University
Nguồn: LibreTexts
Giấy phép: CC BY-NC-SA
Ngôn ngữ: EN
Danh mục: Khoa học cơ bản

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01: Structure and Bonding
1.00: Introduction
1.01: Atomic Structure- The Nucleus
1.02: Atomic Structure- Orbitals
1.03: Atomic Structure- Electron Configurations
1.04: Development of Chemical Bonding Theory
1.05: The Nature of Chemical Bonds- Valence Bond Theory
1.06: sp Hybrid Orbitals and the Structure of Methane
1.07: sp Hybrid Orbitals and the Structure of Ethane
1.08: sp Hybrid Orbitals and the Structure of Ethylene
1.09: 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
1.S: Structure and Bonding (Summary)
02: Polar Covalent Bonds Acids and Bases
2.00: Prelude
2.01: Polar Covalent Bonds- Electronegativity
2.02: Polar Covalent Bonds- Dipole Moments
2.03: Formal Charges
2.04: Resonance
2.05: Rules for Resonance Forms
2.06: Drawing Resonance Forms
2.07: Acids and Bases- The Brnsted-Lowry Definition
2.08: Acid and Base Strength
2.09: 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
2.S: Polar Covalent Bonds Acids and Bases (Summary)
03: Organic Compounds- Alkanes and Their Stereochemistry
3.00: Prelude
3.01: Functional Groups
3.02: Alkanes and Alkane Isomers
3.03: Alkyl Groups
3.04: Naming Alkanes
3.05: Properties of Alkanes
3.06: Conformations of Ethane
3.07: Conformations of Other Alkanes
3.08: Gasoline- A Deeper Look
3.S: Organic Compounds- Alkanes and Their Stereochemistry (Summary)
04: Organic Compounds- Cycloalkanes and their Stereochemistry
4.00: Prelude
4.01: Naming Cycloalkanes
4.02: Cis-Trans Isomerism in Cycloalkanes
4.03: Stability of Cycloalkanes - Ring Strain
4.04: Conformations of Cycloalkanes
4.05: Conformations of Cyclohexane
4.06: Axial and Equatiorial Bonds in Cyclohexane
4.07: Conformations of Monosubstituted Cyclohexanes
4.08: Conformations of Disubstituted Cyclohexanes
4.09: Conformations of Polycyclic Molecules
4.S: Organic Compounds- Cycloalkanes and their Stereochemistry (Summary)
05: Stereochemistry at Tetrahedral Centres
5.00: Prelude
5.01: Enantiomers and the Tetrahedral Carbon
5.02: The Reason for Handedness in Molecules- Chirality
5.03: Optical Activity
5.04: Pasteur's Discovery of Enantiomers
5.05: Sequence Rules for Specifying Configuration
5.06: Diastereomers
5.07: Meso Compounds
5.08: Racemic Mixtures and the Resolution of Enantiomers
5.09: A Review of Isomerism
5.10: Chirality at Nitrogen Phosphorus and Sulfur
5.11: Prochirality
5.12: Chirality in Nature and Chiral Environments
5.S: Stereochemistry at Tetrahedral Centers (Summary)
06: An Overview of Organic Reactions
6.00: Prelude
6.01: Kinds of Organic Reactions
6.02: How Organic Reactions Occur- Mechanisms
6.03: Radical Reactions
6.04: Polar Reactions
6.05: An Example of a Polar Reaction- Addition of HBr to Ethylene
6.06: Using Curved Arrows in Polar Reaction Mechanisms
6.07: Describing a Reaction- Equilibria Rates and Energy Changes
6.08: Describing a Reaction- Bond Dissociation Energies
6.09: Describing a Reaction- Energy Diagrams and Transition States
6.10: Describing a Reaction - Intermediates
6.11: A Comparison between Biological Reactions and Laboratory Reactions
6.S: An Overview of Organic Reactions (Summary)
07: Alkenes- Structure and Reactivity
7.00: Introduction
7.01: Industrial Preparation and Use of Alkenes
7.02: Calculating Degree of Unsaturation
7.03: Naming Alkenes
7.04: Cis-Trans Isomerism in Alkenes
7.05: Sequence Rules- The EZ Designation
7.06: Stability of Alkenes
7.07: Electrophilic Addition Reactions of Alkenes
7.08: Orientation of Electrophilic Additions- Markovnikov's Rule
7.09: Carbocation Structure and Stability
7.10: The Hammond Postulate
7.11: Evidence for the Mechanism of Electrophilic Additions- Carbocation Rearrangements
7.S: Alkenes - Structure and Reactivity (Summary)
08: Alkenes- Reactions and Synthesis
8.00: Prelude
8.01: Preparation of Alkenes- A Preview of Elimination Reactions
8.02: Halogenation of Alkenes- Addition of X
8.03: Halohydrins from Alkenes- Addition of HOX
8.04: Hydration of Alkenes- Addition of HO by Oxymercuration
8.05: Hydration of Alkenes- Addition of HO by Hydroboration
8.06: Reduction of Alkenes- Hydrogenation
8.07: Oxidation of Alkenes- Epoxidation and Hydroxylation
8.08: Oxidation of Alkenes- Cleavage to Carbonyl Compounds
8.09: 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 HO to an Achiral Alkene
8.13: Stereochemistry of Reactions- Addition of HO to a Chiral Alkene
8.S: Alkenes - Reactions and Synthesis (Summary)
09: Alkynes- An Introduction to Organic Synthesis
9.00: Prelude
9.01: Naming Alkynes
9.02: Preparation of Alkynes- Elimination Reactions of Dihalides
9.03: Reactions of Alkynes- Addition of HX and (X 2)
9.04: Hydration of Alkynes
9.05: Reduction of Alkynes
9.06: Oxidative Cleavage of Alkynes
9.07: Alkyne Acidity- Formation of Acetylide Anions
9.08: Alkylation of Acetylide Anions
9.09: An Introduction to Organic Synthesis
9.S: Alkynes - An Introduction to Organic Synthesis (Summary)
10: Organohalides
10.00: Introduction
10.01: Names and Properties of Alkyl Halides
10.02: Preparing Alkyl Halides from Alkanes- Radical Halogenation
10.03: Preparing Alkyl Halides from Alkenes- Allylic Bromination
10.04: Stability of the Allyl Radical- Resonance Revisited
10.05: Preparing Alkyl Halides from Alcohols
10.06: Reactions of Alkyl Halides- Grignard Reagents
10.07: Organometallic Coupling Reactions
10.08: Oxidation and Reduction in Organic Chemistry
10.S: Organohalides (Summary)
11: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations
11.00: Introduction
11.01: The Discovery of Nucleophilic Substitution Reactions
11.02: The SN2 Reaction
11.03: Characteristics of the SN2 Reaction
11.04: The SN1 Reaction
11.05: Characteristics of the SN1 Reaction
11.06: Biological Substitution Reactions
11.07: Elimination Reactions- Zaitsev's Rule
11.08: The E2 Reaction and the Deuterium Isotope Effect
11.09: The E2 Reaction and Cyclohexane Conformation
11.10: The E1 and E1cB Reactions
11.11: Biological Elimination Reactions
11.12: A Summary of Reactivity- SN1 SN2 E1 E1cB and E2
11.S: Reactions of Alkyl Halides - Nucleophilic Substitutions and Eliminations (Summary)
12: Structure Determination- Mass Spectrometry and Infrared Spectroscopy
12.00: Introduction
12.01: Mass Spectrometry of Small Molecules- Magnetic-Sector Instruments
12.02: Interpreting Mass Spectra
12.03: Mass Spectrometry of Some Common Functional Groups
12.04: Mass Spectrometry in Biological- Time-of-flight (TOF) Instruments
12.05: Spectroscopy and the Electromagnetic Spectrum
12.06: Infrared Spectroscopy
12.07: Interpreting Infrared Spectra
12.08: Infrared Spectra of Some Common Functional Groups
12.S: Structure Determination - Mass Spectrometry and Infrared Spectroscopy (Summary)
13: Structure Determination- Nuclear Magnetic Resonance Spectroscopy
13.00: Prelude
13.01: Nuclear Magnetic Resonance Spectroscopy
13.02: The Nature of NMR Absorptions
13.03: Chemical Shifts
13.04: C NMR Spectroscopy- Signal Averaging and FT-NMR
13.05: Characteristics of C NMR Spectroscopy
13.06: DEPT C NMR Spectroscopy
13.07: Uses of C NMR Spectroscopy
13.08: H NMR Spectroscopy and Proton Equivalence
13.09: Chemical Shifts in H NMR Spectroscopy
13.10: Integration of H NMR Absorptions- Proton Counting
13.11: Spin-Spin Splitting in H NMR Spectra
13.12: More Complex Spin-Spin Splitting Patterns
13.13: Uses of H NMR Spectroscopy
13.S: Structure Determination - Nuclear Magnetic Resonance Spectroscopy (Summary)
14: Conjugated Compounds and Ultraviolet Spectroscopy
14.00: Introduction
14.01: Stability of Conjugated Dienes- Molecular Orbital Theory
14.02: Electrophilic Additions to Conjugated Dienes- Allylic Carbocations
14.03: Kinetic vs. Thermodynamic Control of Reactions
14.04: The Diels-Alder Cycloaddition Reaction
14.05: Characteristics of the Diels-Alder Reaction
14.06: Diene Polymers- Natural and Synthetic Rubbers
14.07: Structure Determination in Conjugated Systems- Ultraviolet Spectroscopy
14.08: Interpreting Ultraviolet Spectra- The Effect of Conjugation
14.09: Conjugation Color and the Chemistry of Vision
14.S: Conjugated Compounds and Ultraviolet Spectroscopy (Summary)
15: Benzene and Aromaticity
15.00: Introduction
15.01: Sources and Names of Aromatic Compounds
15.02: Structure and Stability of Benzene
15.03: Aromaticity and the Huckel 4n 2 Rule
15.04: Aromatic Ions
15.05: Aromatic Heterocycles- Pyridine and Pyrrole
15.06: Polycyclic Aromatic Compounds
15.07: Spectroscopy of Aromatic Compounds
15.S: Benzene and Aromaticity (Summary)
16: Chemistry of Benzene- Electrophilic Aromatic Substitution
16.00: Introduction
16.01: Electrophilic Aromatic Substitution Reactions- Bromination
16.02: Other Aromatic Substitutions
16.03: Alkylation and Acylation of Aromatic Rings- The Friedel-Crafts Reaction
16.04: Substituent Effects in Substituted Aromatic Rings
16.05: An Explanation of Substituent Effects
16.06: Trisubstituted Benzenes- Additivity of Effects
16.07: Nucleophilic Aromatic Substitution
16.08: Benzyne
16.09: Oxidation of Aromatic Compounds
16.10: Reduction of Aromatic Compounds
16.11: Synthesis of Polysubstituted Benzenes
16.S: Chemistry of Benzene - Electrophilic Aromatic Substitution (Summary)