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Organic Chemistry Text Book (CHEM 3401 and 3402)
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Organic Chemistry Text Book (CHEM 3401 and 3402)
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Chapter 1: A Review of General Chemistry
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1.1 Introduction to Organic Chemistry
1.2 Electrons, Bonds, and Lewis Structures
1.3 Identifying Formal Charges
1.4 Atomic Orbitals
1.5 Valence Bond Theory
1.6 Molecular Orbital Theory/Hybridization
1.7 VSEPR Theory: Predicting Geometry
1.8 Dipole Moments and Molecular Polarity
1.9 Intermolecular Forces and Physical Properties
Problem Set
Videos for chapter 1
Chapter 2: Molecular Representations
2.1 Molecular Representations and Bond-Line Structures
2.2 Functional Groups
2.3 Formal Charges and Lone Pairs
2.4 Introduction to Resonance and Resonance Structures
2.5 Curved Arrows
2.6 Practice Problems
Chapter 2 Videos
Chapter 3: Acids and Bases
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3.1 Bronsted Acids and Bases
3.2 Acidity Constant
3.3 Structural Effects on Acidity and Basicity
3.4 Lewis Acids and Bases
3.5 Practice Problems
Chapter 3 Videos
Chapter 4: Alkanes and Cycloalkanes
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4.1 Alkane Introduction and Nomenclature
4.2 Configurational Stereoisomers of Cycloalkanes
4.3 Conformational Stereoisomers
4.4 Chair and Boat Conformations
4.5 Practice Problems
Chapter 4 Videos
Chapter 5: Stereochemistry
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5.1 Isomerism and Stereoisomerism
5.2 R and S Configurations
5.3 Enantiomers and Diastereomers
5.4 Optical Activity, Symmetry, and Chirality
5.5 Fisher and Other Configurational Notations
5.6 Meso Compounds
5.7 Resolution of Racemates
5.8 Summary of Stereoisomerism
Problem Set
Chapter 5 Videos
Chapter 6: Chemical Reactivity and Mechanisms
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6.1 Bond Energy
6.2 Equilibria, Kinetics, and Energy Diagrams
6.3 Nucleophiles and Electrophiles
6.4 Mechanisms and Curved Arrows
6.5 Carbocation Rearrangements
6.6 Reaction Variables
6.7 Examples of Organic Reactions
Problem Set
Chapter 6 Videos
Chapter 7: Substitution Reactions
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7.1 Alkyl Halides
7.2 Introduction of Substitution and Elimination Reactions
7.3 Substitution Reactions
7.4 Elimination Reactions
7.5 Summary of Substitution vs. Elimination
Problem Set
Chapter 7 Videos
Chapter 8: Addition Reactions of Alkenes
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8.1 Introduction of Addition Reactions
8.1 Nomenclature of Alkenes
8.2 Hydrohalogenation of Alkenes
8.3 Hydration, Hydroboration, and Oxymercuration of Alkenes
8.4 Hydrogenation of Alkenes
8.5 Halogenation of Alkenes
8.6 Dihydroxylation, Epoxidation, and Ozonolysis of Alkenes
Problem Set
Chapter 8 Videos
Chapter 9: Alkynes
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9.1 Introduction of Alkynes
9.2 Nomenclature of Alkynes
9.3 Alkylation of Alkynes
9.4 Preparation of Alkynes
9.5 Addition Reactions of Alkynes
9.6 Reduction of Alkynes
9.7 Oxidation of Alkynes
9.8.1 Alkyne Reactions-1
Problem Set
Chapter 9 Videos
Chapter 10: Radicals
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10.1 Introduction of Radicals
10.2 Halogenation of Alkanes
10.3 Allylic Substitution
Problem Set
Chapter 10 Videos
Chapter 11: Synthesis
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11.1 Introduction to Synthesis
11.2 Worked Synthesis Examples
11.3 Principles of Modern Synthesis
11.4 Stereoselective Synthesis
Problem Set
Chapter 11 Videos
Problem Sets Organic Chemistry I (CHEM 3401)
Chapter 12: Alcohols and Phenols
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12.1 Alcohol Structure
12.2 Solubility
12.3 Boiling Point & Melting Point
12.4 Nomenclature
12.5 Alcohol Acidity
12.6 Reactions of Alcohols and Phenols
12.6.1 Substitution of the Hydroxyl Hydrogen
12.6.2 Nucleophilic Substitution of the Hydroxyl Group
12.6.3 Elimination Reactions of Alcohols
12.6.4 Oxidation Reactions of Alcohols
12.6.5 Reactions of Phenols
12.7 Practice Problems
12.7.1 Alcohol Nomenclature 1
12.7.2 Alcohol Nomenclature 2
12.7.3 Alcohol Nomenclature 3
12.7.4 Formation of Carbonyl Compounds
12.7.5 Functional Relationships of Alcohols
12.7.6 Reactions of Alcohols & Phenols
12.7.7 Alcohol Reactions
Chapter 13: Ethers and Epoxides
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13.1 Nomenclature of Ethers
13.2 Preparation of Ethers
13.3 Reactions of Ethers
13.3.1 Acid Cleavage
13.3.2 Peroxide Formation
13.4 Nomenclature of Epoxides
13.5 Preparations of Epoxides
13.6 Reactions of Epoxides
13.7 Thiols and Sulfides
13.8 Practice Problems
Chapter 14: Infrared Spectroscopy and Mass Spectrometry
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14.1 Introduction fo Molecular Spectroscopy
14.2 Infrared Spectroscopy
14.2.1 Introduction
14.2.2 Vibrational Spectroscopy
14.2.3 Group Frequencies
14.2.4 Table of Characteristic IR Frequencies
14.3 Mass Spectrometry
14.3.1 The Mass Spectrometer
14.3.2 Characteristics of Mass Spectra
14.3.3 Isotopes
14.3.4 Fragmentation Patterns
14.3.5 High Resolution Spectra
14.3.6 MS Practice Problems
14.3.6a Problem 1
14.3.6b Problem 2
14.3.6c Problem 3
14.3.6d Problem 4
14.3.6e Problem 5
14.3.6f Problem 6
14.3.6g Problem 7
14.3.6h Problem 8
Chapter 15: Nuclear Magnetic Resonance Spectroscopy and UV-Visible Spectroscopy
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15.1 Nuclear Magnetic Resonance Spectroscopy
15.1.1 Background
15.1.2 Proton NMR Spectroscopy
15.1.2a Introduction to Proton NMR Spectroscopy
15.1.2b Chemical Shift
15.1.2c Signal Strength
15.1.2d Hydroxyl Proton Exchange and the Influence of Hydrogen Bonding
15.1.2e Pi-Electron Functions
15.1.2f Solvent Effects
15.1.2g Spin-Spin Interactions
15.1.2h Examples
15.1.3 Carbon NMR Spectroscopy
15.1.4 NMR Practice Problems
15.1.4a Problem 1
15.1.4b Problem 2
15.1.4c Problem 3
15.1.4d Problem 4
15.1.4e Problem 5
15.1.4f Problem 6
15.1.4g Problem 7
15.1.4h Problem 8
15.1.4i Problem 9
15.1.4j Problem 10
15.1.5 Table of Proton NMR Shifts
15.1.6 Table of Carbon NMR Shifts
15.2 UV-Visible Spectroscopy
15.2.1 Background
15.2.2 The Electromagnetic Spectrum
15.2.3 UV-Visible Absorption Spectra
15.2.4 The Importance of Conjugation
15.3 Spectroscopy Practice Problems
Chapter 16: Conjugated Pi Systems and Pericyclic Reactions
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16.1 Dienes
16.2 Addition Reactions of Dienes
16.3 Diels-Alder Cycloaddition
16.4 Practice Problems
16.4.1 Problem 1
16.4.2 Problem 2
16.4.3 Problem 3
16.4.4 Problem 4
16.4.5 Problem 5
16.4.6 Problem 6
Chapter 17: Aromatic Compounds
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17.1 Aromaticity
17.1.1 Benzene
17.1.2 Fused Ring Compounds
17.1.3 Other Aromatic Compounds
17.1.4 Antiaromaticity
17.1.5 Practice Problems
17.1.5a Problem 1
17.1.5b Problem 2
17.2 Reactions of Substituent Groups
17.2.1 Oxidation of Alkyl Side-Chains
17.2.2 Bromination of Alkyl Side-Chains
17.2.3 Reduction of Nitro Groups
Chapter 17 Videos
Chapter 18: Aromatic Substitution Reactions
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18.1 Electrophilic Aromatic Substitution Reactions
18.2 Electrophilic Aromatic Substitution Mechanism
18.3 Electrophilic Aromatic Substitution Activation/Deactivation and Orientation
18.4 Electrophilic Substitution of Disubstituted Benzene Rings
18.5 Practice Problems
18.5.1 Problem 1
18.5.2 Problem 2
18.5.3 Problem 3
18.5.4 Problem 4
18.5.5 Problem 5
18.5.6 Problem 6
18.5.7 Problem 7
Chapter 18 Videos
Chapter 19: Aldehydes and Ketones
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19.1 Nomenclature
19.2 Preparation of Aldehydes and Ketones
19.3 Properties of Aldehydes and Ketones
19.4 Reactions of Aldehydes and Ketones
19.4.1 Addition Reactions
19.4.1a Hydration
19.4.1b Acetal Formation
19.4.1c Imine Formation
19.4.1d Cyanohydrin Formation
19.4.1e Hydride Reduction
19.4.1f Addition of Organometallic Reagents
19.4.2 Reduction of Aldehydes and Ketones
19.4.2a Wolff-Kishner Reduction
19.4.2b Clemmensen Reduction
19.4.3 Oxidation of Aldehydes and Ketones
19.5 Practice Problems
19.5.1 Problem 1
19.5.2 Problem 2
19.5.3 Problem 3
19.5.4 Problem 4
19.5.5 Problem 5
19.5.6 Problem 6
19.5.7 Problem 7
19.5.8 Problem 8
19.5.9 Problem 9
19.5.10 Problem 10
19.5.11 Problem 11
19.5.12 Problem 12
Chapter 20: Carboxylic Acids and Their Derivatives
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20.1 Nomenclature
20.2 Physical Properties
20.3 Acidity
20.4 Preparation of Carboxylic Acids
20.5 Reactions of Carboxylic Acids
20.5.1 Salt Formation
20.5.2 Substitution of the Hydroxyl Hydrogen
20.5.3 Substitution of the Hydroxyl Group
20.5.4 Reduction
20.5.5 Oxidation
20.6 Practice Problems-Carboxylic Acids
20.6.1 Nomenclature Practice-1
20.6.2 Nomenclature Practice-2
20.6.3 Acidity
20.6.4 Reactions of Carboxylic Acids
20.7 Carboxylic Acid Derivatives
20.7.1 Related Derivatives
20.7.2 Nomenclature
20.7.3 Reactions
20.7.3a Acyl Substitution
20.7.3b Nitrile Hydrolysis
20.7.3c Reductions
20.7.3d Reactions with Organometallic Reagents
20.7.3e Dehydration of Amides
20.7.4 Practice Problems-Carboxylic Acid Derivatives
20.7.4a Nomenclature Practice-1
20.7.4b Nomenclature Practice-2
20.7.4c Carbonyl Compounds
20.8 Practice Problems
20.8.1 Problem 1
20.8.2 Problem 2
20.8.3 Problem 3
20.8.4 Problem 4
20.8.5 Problem 5
20.8.6 Problem 6
Chapter 21: Alpha Carbon Chemistry: Enols and Enolates
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21.1 Reactions at the Alpha Carbon
21.2 Alpha Halogenation of Enols and Enolates
21.3 Aldol Reaction
21.4 Claisen Condensation
21.5 Alkylation at the Alpha Position
21.5.1 Enolate Alkylation
21.5.2 Dicarbonyl Alkylation
21.5.3 Decarboxylation Following Alkylation
21.5.4 Conjugate Reactions
21.5.4a Michael Reaction
21.5.4b Robinson Annulation
21.5.4c With Hydrides and Organometallics
21.6 Practice Problem
21.6.1 Problem 1
Org Chem II - Problem Sets - Collection (CHEM 3402)
Problem Set
Chapter 2
Part 1 - Drawing Skeletal Structures
Part 2 - Functional Groups
Part 3 - Resonance
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