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Table of contents
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1. A Review of General Chemistry
(0)
Worksheet
Summary
(0)
Intro to Organic Chemistry
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Atomic Structure
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Wave Function
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Molecular Orbitals
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Sigma and Pi Bonds
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Octet Rule
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Bonding Preferences
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Formal Charges
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Skeletal Structure
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Lewis Structure
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Condensed Structural Formula
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Degrees of Unsaturation
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Constitutional Isomers
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Resonance Structures
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Hybridization
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Molecular Geometry
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Electronegativity
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2. Molecular Representations
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Worksheet
Intermolecular Forces
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How To Determine Solubility
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Functional Groups
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3. Acids and Bases
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Worksheet
Organic Chemistry Reactions
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Reaction Mechanism
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Acids and Bases
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Equilibrium Constant
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pKa
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Acid Base Equilibrium
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Ranking Acidity
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4. Alkanes and Cycloalkanes
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Worksheet
IUPAC Naming
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Alkyl Groups
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Naming Cycloalkanes
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Naming Bicyclic Compounds
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Naming Alkyl Halides
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Naming Alkenes
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Naming Alcohols
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Naming Amines
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Cis vs Trans
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Conformational Isomers
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Newman Projections
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Drawing Newman Projections
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Barrier To Rotation
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Ring Strain
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Axial vs Equatorial
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Cis vs Trans Conformations
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Equatorial Preference
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Chair Flip
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Calculating Energy Difference Between Chair Conformations
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A-Values
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Decalin
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5. Chirality
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Worksheet
Constitutional Isomers vs. Stereoisomers
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Chirality
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Test 1:Plane of Symmetry
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Test 2:Stereocenter Test
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R and S Configuration
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Enantiomers vs. Diastereomers
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Atropisomers
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Meso Compound
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Test 3:Disubstituted Cycloalkanes
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What is the Relationship Between Isomers?
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Fischer Projection
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R and S of Fischer Projections
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Optical Activity
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Enantiomeric Excess
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Calculations with Enantiomeric Percentages
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Non-Carbon Chiral Centers
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6. Thermodynamics and Kinetics
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Worksheet
Energy Diagram
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Gibbs Free Energy
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Enthalpy
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Entropy
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Hammond Postulate
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Carbocation Stability
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Carbocation Intermediate Rearrangements
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7. Substitution Reactions
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Worksheet
Nucleophilic Substitution
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Good Leaving Groups
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SN2 Reaction
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SN1 Reaction
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Substitution Comparison
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8. Elimination Reactions
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Worksheet
E2 Mechanism
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Beta Hydrogen
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E2 - Anti-Coplanar Requirement
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E2 - Cumulative Practice
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E1 Reaction
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Solvents
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Leaving Groups
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Nucleophiles and Basicity
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SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)
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Cumulative Substitution/Elimination
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9. Alkenes and Alkynes
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Worksheet
Alkene Stability
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Zaitsev Rule
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Dehydrohalogenation
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Double Elimination
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Acetylide
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Hydrogenation of Alkynes
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Dehydration Reaction
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POCl3 Dehydration
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Alkynide Synthesis
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10. Addition Reactions
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Worksheet
Addition Reaction
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Markovnikov
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Hydrohalogenation
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Acid-Catalyzed Hydration
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Oxymercuration
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Hydroboration
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Hydrogenation
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Halogenation
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Halohydrin
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Carbene
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Epoxidation
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Epoxide Reactions
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Dihydroxylation
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Ozonolysis
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Ozonolysis Full Mechanism
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Oxidative Cleavage
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Alkyne Oxidative Cleavage
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Alkyne Hydrohalogenation
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Alkyne Halogenation
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Alkyne Hydration
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Alkyne Hydroboration
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11. Radical Reactions
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Worksheet
Radical Reaction
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Radical Stability
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Free Radical Halogenation
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Radical Selectivity
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Calculating Radical Yields
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Anti Markovnikov Addition of Br
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Free Radical Polymerization
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Allylic Bromination
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Radical Synthesis
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12. Alcohols, Ethers, Epoxides and Thiols
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Worksheet
Alcohol Nomenclature
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Naming Ethers
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Naming Epoxides
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Naming Thiols
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Alcohol Synthesis
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Leaving Group Conversions - Using HX
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Leaving Group Conversions - SOCl2 and PBr3
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Leaving Group Conversions - Sulfonyl Chlorides
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Leaving Group Conversions Summary
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Williamson Ether Synthesis
(0)
Making Ethers - Alkoxymercuration
(0)
Making Ethers - Alcohol Condensation
(0)
Making Ethers - Acid-Catalyzed Alkoxylation
(0)
Making Ethers - Cumulative Practice
(0)
Ether Cleavage
(0)
Alcohol Protecting Groups
(0)
t-Butyl Ether Protecting Groups
(0)
Silyl Ether Protecting Groups
(0)
Sharpless Epoxidation
(0)
Thiol Reactions
(0)
Sulfide Oxidation
(0)
13. Alcohols and Carbonyl Compounds
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Worksheet
Oxidizing and Reducing Agents
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Oxidizing Agent
(0)
Reducing Agent
(0)
Nucleophilic Addition
(0)
Preparation of Organometallics
(0)
Grignard Reaction
(0)
Protecting Alcohols from Organometallics
(0)
Organometallic Cumulative Practice
(0)
14. Synthetic Techniques
(0)
Worksheet
Synthetic Cheatsheet
(0)
Moving Functionality
(0)
Alkynide Alkylation
(0)
Alkane Halogenation
(0)
Retrosynthesis
(0)
15. Analytical Techniques:IR, NMR, Mass Spect
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Worksheet
Purpose of Analytical Techniques
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Infrared Spectroscopy
(0)
Infrared Spectroscopy Table
(0)
IR Spect:Drawing Spectra
(0)
IR Spect:Extra Practice
(0)
NMR Spectroscopy
(0)
1H NMR:Number of Signals
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1H NMR:Q-Test
(0)
1H NMR:E/Z Diastereoisomerism
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H NMR Table
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1H NMR:Spin-Splitting (N + 1) Rule
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1H NMR:Spin-Splitting Simple Tree Diagrams
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1H NMR:Spin-Splitting Complex Tree Diagrams
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1H NMR:Spin-Splitting Patterns
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NMR Integration
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NMR Practice
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Carbon NMR
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Structure Determination without Mass Spect
(0)
Mass Spectrometry
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Mass Spect:Fragmentation
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Mass Spect:Isotopes
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16. Conjugated Systems
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Worksheet
Conjugation Chemistry
(0)
Stability of Conjugated Intermediates
(0)
Allylic Halogenation
(0)
Conjugated Hydrohalogenation (1,2 vs 1,4 addition)
(0)
Diels-Alder Reaction
(0)
Diels-Alder Forming Bridged Products
(0)
Diels-Alder Retrosynthesis
(0)
Molecular Orbital Theory
(0)
Drawing Atomic Orbitals
(0)
Drawing Molecular Orbitals
(0)
HOMO LUMO
(0)
Orbital Diagram:3-atoms- Allylic Ions
(0)
Orbital Diagram:4-atoms- 1,3-butadiene
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Orbital Diagram:5-atoms- Allylic Ions
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Orbital Diagram:6-atoms- 1,3,5-hexatriene
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Orbital Diagram:Excited States
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Pericyclic Reaction
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Thermal Cycloaddition Reactions
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Photochemical Cycloaddition Reactions
(0)
Thermal Electrocyclic Reactions
(0)
Photochemical Electrocyclic Reactions
(0)
Cumulative Electrocyclic Problems
(0)
Sigmatropic Rearrangement
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Cope Rearrangement
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Claisen Rearrangement
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17. Aromaticity
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Worksheet
Aromaticity
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Huckel's Rule
(0)
Pi Electrons
(0)
Aromatic Hydrocarbons
(0)
Annulene
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Aromatic Heterocycles
(0)
Frost Circle
(0)
Naming Benzene Rings
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Acidity of Aromatic Hydrocarbons
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Basicity of Aromatic Heterocycles
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Ionization of Aromatics
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18. Reactions of Aromatics:EAS and Beyond
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Worksheet
Electrophilic Aromatic Substitution
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Benzene Reactions
(0)
EAS:Halogenation Mechanism
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EAS:Nitration Mechanism
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EAS:Friedel-Crafts Alkylation Mechanism
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EAS:Friedel-Crafts Acylation Mechanism
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EAS:Any Carbocation Mechanism
(0)
Electron Withdrawing Groups
(0)
EAS:Ortho vs. Para Positions
(0)
Acylation of Aniline
(0)
Limitations of Friedel-Crafts Alkyation
(0)
Advantages of Friedel-Crafts Acylation
(0)
Blocking Groups - Sulfonic Acid
(0)
EAS:Synergistic and Competitive Groups
(0)
Side-Chain Halogenation
(0)
Side-Chain Oxidation
(0)
Birch Reduction
(0)
EAS:Sequence Groups
(0)
EAS:Retrosynthesis
(0)
Diazo Replacement Reactions
(0)
Diazo Sequence Groups
(0)
Diazo Retrosynthesis
(0)
Nucleophilic Aromatic Substitution
(0)
Benzyne
(0)
19. Aldehydes and Ketones:Nucleophilic Addition
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Worksheet
Naming Aldehydes
(0)
Naming Ketones
(0)
Oxidizing and Reducing Agents
(0)
Oxidation of Alcohols
(0)
Ozonolysis
(0)
DIBAL
(0)
Alkyne Hydration
(0)
Nucleophilic Addition
(0)
Cyanohydrin
(0)
Organometallics on Ketones
(0)
Overview of Nucleophilic Addition of Solvents
(0)
Hydrates
(0)
Hemiacetal
(0)
Acetal
(0)
Acetal Protecting Group
(0)
Thioacetal
(0)
Imine vs Enamine
(0)
Addition of Amine Derivatives
(0)
Wolff Kishner Reduction
(0)
Baeyer-Villiger Oxidation
(0)
Acid Chloride to Ketone
(0)
Nitrile to Ketone
(0)
Wittig Reaction
(0)
Ketone and Aldehyde Synthesis Reactions
(0)
20. Carboxylic Acid Derivatives:NAS
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Worksheet
Carboxylic Acid Derivatives
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Naming Carboxylic Acids
(0)
Diacid Nomenclature
(0)
Naming Esters
(0)
Naming Nitriles
(0)
Acid Chloride Nomenclature
(0)
Naming Anhydrides
(0)
Naming Amides
(0)
Nucleophilic Acyl Substitution
(0)
Carboxylic Acid to Acid Chloride
(0)
Fischer Esterification
(0)
Acid-Catalyzed Ester Hydrolysis
(0)
Saponification
(0)
Transesterification
(0)
Lactones, Lactams and Cyclization Reactions
(0)
Carboxylation
(0)
Decarboxylation Mechanism
(0)
21. Enolate Chemistry:Reactions at the Alpha-Carbon
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Worksheet
Tautomerization
(0)
Tautomers of Dicarbonyl Compounds
(0)
Enolate
(0)
Acid-Catalyzed Alpha-Halogentation
(0)
Base-Catalyzed Alpha-Halogentation
(0)
Haloform Reaction
(0)
Hell-Volhard-Zelinski Reaction
(0)
Overview of Alpha-Alkylations and Acylations
(0)
Enolate Alkylation and Acylation
(0)
Enamine Alkylation and Acylation
(0)
Beta-Dicarbonyl Synthesis Pathway
(0)
Acetoacetic Ester Synthesis
(0)
Malonic Ester Synthesis
(0)
22. Condensation Chemistry
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Worksheet
Condensation Reactions
(0)
Aldol Condensation
(0)
Directed Condensations
(0)
Crossed Aldol Condensation
(0)
Claisen-Schmidt Condensation
(0)
Claisen Condensation
(0)
Intramolecular Aldol Condensation
(0)
Conjugate Addition
(0)
Michael Addition
(0)
Robinson Annulation
(0)
23. Amines
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Worksheet
Amine Alkylation
(0)
Gabriel Synthesis
(0)
Amines by Reduction
(0)
Nitrogenous Nucleophiles
(0)
Reductive Amination
(0)
Curtius Rearrangement
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Hofmann Rearrangement
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Hofmann Elimination
(0)
Cope Elimination
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24. Carbohydrates
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Worksheet
Monosaccharide
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Monosaccharides - D and L Isomerism
(0)
Monosaccharides - Drawing Fischer Projections
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Monosaccharides - Common Structures
(0)
Monosaccharides - Forming Cyclic Hemiacetals
(0)
Monosaccharides - Cyclization
(0)
Monosaccharides - Haworth Projections
(0)
Mutarotation
(0)
Epimerization
(0)
Monosaccharides - Aldose-Ketose Rearrangement
(0)
Monosaccharides - Alkylation
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Monosaccharides - Acylation
(0)
Glycoside
(0)
Monosaccharides - N-Glycosides
(0)
Monosaccharides - Reduction (Alditols)
(0)
Monosaccharides - Weak Oxidation (Aldonic Acid)
(0)
Reducing Sugars
(0)
Monosaccharides - Strong Oxidation (Aldaric Acid)
(0)
Monosaccharides - Oxidative Cleavage
(0)
Monosaccharides - Osazones
(0)
Monosaccharides - Kiliani-Fischer
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Monosaccharides - Wohl Degradation
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Monosaccharides - Ruff Degradation
(0)
Disaccharide
(0)
Polysaccharide
(0)
25. Phenols
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Worksheet
Phenol Acidity
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26. Amino Acids, Peptides, and Proteins
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Worksheet
Proteins and Amino Acids
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L and D Amino Acids
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Polar Amino Acids
(0)
Amino Acid Chart
(0)
Acid-Base Properties of Amino Acids
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Isoelectric Point
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27. Transition Metals
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Worksheet
Electron Configuration of Elements
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Coordination Complexes
(0)
Ligands
(0)
Electron Counting
(0)
The 18 and 16 Electron Rule
(0)
Cross-Coupling General Reactions
(0)
Heck Reaction
(0)
Stille Reaction
(0)
Suzuki Reaction
(0)
Sonogashira Coupling Reaction
(0)
Fukuyama Coupling Reaction
(0)
Kumada Coupling Reaction
(0)
Negishi Coupling Reaction
(0)
Buchwald-Hartwig Amination Reaction
(0)
Eglinton Reaction
(0)
32. Lipids
(0)
Worksheet
Intro to Lipids
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Fatty Acids
(0)
Physical Properties of Fatty Acids
(0)
Waxes
(0)
Triacylglycerols
(0)
Triacylglycerol Reactions: Hydrogenation
(0)
Triacylglycerol Reactions: Hydrolysis
(0)
Phosphoglycerides
(0)
Sphingomyelins
(0)
Steroids
(0)
34. Nucleic Acids
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Worksheet
Intro to Nucleic Acids
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Nitrogenous Bases
(0)
Naming Nucleosides and Nucleotides
(0)
Hydrolysis of Nucleosides
(0)
Primary Structure of Nucleic Acids
(0)
Base Pairing
(0)
DNA Double Helix
(0)
19. Aldehydes and Ketones:Nucleophilic Addition
Thioacetal Practice Problems
19. Aldehydes and Ketones:Nucleophilic Addition
Thioacetal Practice Problems
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