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Organic Chemistry Text Book (CHEM 3401 and 3402)
21.5 Alkylation at the Alpha Position

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Organic Chemistry Text Book (CHEM 3401 and 3402)

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Chapter 1: A Review of General ChemistryToggle Dropdown
- 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 RepresentationsToggle Dropdown
- 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 BasesToggle Dropdown
- 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 CycloalkanesToggle Dropdown
- 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: StereochemistryToggle Dropdown
- 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 MechanismsToggle Dropdown
- 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 ReactionsToggle Dropdown
- 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 AlkenesToggle Dropdown
- 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: AlkynesToggle Dropdown
- 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: RadicalsToggle Dropdown
- 10.1 Introduction of Radicals
- 10.2 Halogenation of Alkanes
- 10.3 Allylic Substitution
- Problem Set
- Chapter 10 Videos
Chapter 11: SynthesisToggle Dropdown
- 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 PhenolsToggle Dropdown
- 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 EpoxidesToggle Dropdown
- 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 SpectrometryToggle Dropdown
- 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 SpectroscopyToggle Dropdown
- 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 ReactionsToggle Dropdown
- 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 CompoundsToggle Dropdown
- 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 ReactionsToggle Dropdown
- 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 KetonesToggle Dropdown
- 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 DerivativesToggle Dropdown
- 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
- 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

21.5 Alkylation at the Alpha Position

Alkylation at the Alpha Position

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