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