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1. A Review of General Chemistry(0)

Summary
(0)

Intro to Organic Chemistry
(0)

Atomic Structure
(0)

Wave Function
(0)

Molecular Orbitals
(0)

Sigma and Pi Bonds
(0)

Octet Rule
(0)

Bonding Preferences
(0)

Formal Charges
(0)

Skeletal Structure
(0)

Lewis Structure
(0)

Condensed Structural Formula
(0)

Degrees of Unsaturation
(0)

Constitutional Isomers
(0)

Resonance Structures
(0)

Hybridization
(0)

Molecular Geometry
(0)

Electronegativity
(0)

2. Molecular Representations(0)

Intermolecular Forces
(0)

How To Determine Solubility
(0)

Functional Groups
(0)

3. Acids and Bases(0)

Organic Chemistry Reactions
(0)

Reaction Mechanism
(0)

Acids and Bases
(0)

Equilibrium Constant
(0)

pKa
(0)

Acid Base Equilibrium
(0)

Ranking Acidity
(0)

4. Alkanes and Cycloalkanes(0)

IUPAC Naming
(0)

Alkyl Groups
(0)

Naming Cycloalkanes
(0)

Naming Bicyclic Compounds
(0)

Naming Alkyl Halides
(0)

Naming Alkenes
(0)

Naming Alcohols
(0)

Naming Amines
(0)

Cis vs Trans
(0)

Conformational Isomers
(0)

Newman Projections
(0)

Drawing Newman Projections
(0)

Barrier To Rotation
(0)

Ring Strain
(0)

Axial vs Equatorial
(0)

Cis vs Trans Conformations
(0)

Equatorial Preference
(0)

Chair Flip
(0)

Calculating Energy Difference Between Chair Conformations
(0)

A-Values
(0)

Decalin
(0)

5. Chirality(0)

Constitutional Isomers vs. Stereoisomers
(0)

Chirality
(0)

Test 1:Plane of Symmetry
(0)

Test 2:Stereocenter Test
(0)

R and S Configuration
(0)

Enantiomers vs. Diastereomers
(0)

Atropisomers
(0)

Meso Compound
(0)

Test 3:Disubstituted Cycloalkanes
(0)

What is the Relationship Between Isomers?
(0)

Fischer Projection
(0)

R and S of Fischer Projections
(0)

Optical Activity
(0)

Enantiomeric Excess
(0)

Calculations with Enantiomeric Percentages
(0)

Non-Carbon Chiral Centers
(0)

6. Thermodynamics and Kinetics(0)

Energy Diagram
(0)

Gibbs Free Energy
(0)

Enthalpy
(0)

Entropy
(0)

Hammond Postulate
(0)

Carbocation Stability
(0)

Carbocation Intermediate Rearrangements
(0)

7. Substitution Reactions(0)

Nucleophilic Substitution
(0)

Good Leaving Groups
(0)

SN2 Reaction
(0)

SN1 Reaction
(0)

Substitution Comparison
(0)

8. Elimination Reactions(0)

E2 Mechanism
(0)

Beta Hydrogen
(0)

E2 - Anti-Coplanar Requirement
(0)

E2 - Cumulative Practice
(0)

E1 Reaction
(0)

Solvents
(0)

Leaving Groups
(0)

Nucleophiles and Basicity
(0)

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)
(0)

Cumulative Substitution/Elimination
(0)

9. Alkenes and Alkynes(0)

Alkene Stability
(0)

Zaitsev Rule
(0)

Dehydrohalogenation
(0)

Double Elimination
(0)

Acetylide
(0)

Hydrogenation of Alkynes
(0)

Dehydration Reaction
(0)

POCl3 Dehydration
(0)

Alkynide Synthesis
(0)

10. Addition Reactions(0)

Addition Reaction
(0)

Markovnikov
(0)

Hydrohalogenation
(0)

Acid-Catalyzed Hydration
(0)

Oxymercuration
(0)

Hydroboration
(0)

Hydrogenation
(0)

Halogenation
(0)

Halohydrin
(0)

Carbene
(0)

Epoxidation
(0)

Epoxide Reactions
(0)

Dihydroxylation
(0)

Ozonolysis
(0)

Ozonolysis Full Mechanism
(0)

Oxidative Cleavage
(0)

Alkyne Oxidative Cleavage
(0)

Alkyne Hydrohalogenation
(0)

Alkyne Halogenation
(0)

Alkyne Hydration
(0)

Alkyne Hydroboration
(0)

11. Radical Reactions(0)

Radical Reaction
(0)

Radical Stability
(0)

Free Radical Halogenation
(0)

Radical Selectivity
(0)

Calculating Radical Yields
(0)

Anti Markovnikov Addition of Br
(0)

Free Radical Polymerization
(0)

Allylic Bromination
(0)

Radical Synthesis
(0)

12. Alcohols, Ethers, Epoxides and Thiols(0)

Alcohol Nomenclature
(0)

Naming Ethers
(0)

Naming Epoxides
(0)

Naming Thiols
(0)

Alcohol Synthesis
(0)

Leaving Group Conversions - Using HX
(0)

Leaving Group Conversions - SOCl2 and PBr3
(0)

Leaving Group Conversions - Sulfonyl Chlorides
(0)

Leaving Group Conversions Summary
(0)

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(0)

Oxidizing and Reducing Agents
(0)

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)

Synthetic Cheatsheet
(0)

Moving Functionality
(0)

Alkynide Alkylation
(0)

Alkane Halogenation
(0)

Retrosynthesis
(0)

15. Analytical Techniques:IR, NMR, Mass Spect(0)

Purpose of Analytical Techniques
(0)

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
(0)

1H NMR:Q-Test
(0)

1H NMR:E/Z Diastereoisomerism
(0)

H NMR Table
(0)

1H NMR:Spin-Splitting (N + 1) Rule
(0)

1H NMR:Spin-Splitting Simple Tree Diagrams
(0)

1H NMR:Spin-Splitting Complex Tree Diagrams
(0)

1H NMR:Spin-Splitting Patterns
(0)

NMR Integration
(0)

NMR Practice
(0)

Carbon NMR
(0)

Structure Determination without Mass Spect
(0)

Mass Spectrometry
(0)

Mass Spect:Fragmentation
(0)

Mass Spect:Isotopes
(0)

16. Conjugated Systems(0)

Conjugation Chemistry
(0)

Stability of Conjugated Intermediates
(0)

Allylic Halogenation
(0)

Reactions at the Allylic Position
(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
(0)

Orbital Diagram:5-atoms- Allylic Ions
(0)

Orbital Diagram:6-atoms- 1,3,5-hexatriene
(0)

Orbital Diagram:Excited States
(0)

Pericyclic Reaction
(0)

Thermal Cycloaddition Reactions
(0)

Photochemical Cycloaddition Reactions
(0)

Thermal Electrocyclic Reactions
(0)

Photochemical Electrocyclic Reactions
(0)

Cumulative Electrocyclic Problems
(0)

Sigmatropic Rearrangement
(0)

Cope Rearrangement
(0)

Claisen Rearrangement
(0)

17. Ultraviolet Spectroscopy(0)

The UV-Vis Spectroscopy
(0)

The Beer-Lambert Law
(0)

UV-Vis Spectroscopy of Conjugated Alkenes
(0)

Woodward-Fieser Rules
(0)

18. Aromaticity(0)

Aromaticity
(0)

Huckel's Rule
(0)

Pi Electrons
(0)

Aromatic Hydrocarbons
(0)

Annulene
(0)

Aromatic Heterocycles
(0)

Frost Circle
(0)

Naming Benzene Rings
(0)

Acidity of Aromatic Hydrocarbons
(0)

Basicity of Aromatic Heterocycles
(0)

Ionization of Aromatics
(0)

19. Reactions of Aromatics: EAS and Beyond(0)

Electrophilic Aromatic Substitution
(0)

Benzene Reactions
(0)

EAS:Halogenation Mechanism
(0)

EAS:Nitration Mechanism
(0)

EAS:Friedel-Crafts Alkylation Mechanism
(0)

EAS:Friedel-Crafts Acylation Mechanism
(0)

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)

Reactions at Benzylic Positions
(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)

20. Phenols(0)

Phenol Acidity
(0)

Oxidation of Phenols to Quinones
(0)

Cleavage of Phenyl Ethers
(0)

Kolbe-Schmidt Reaction
(0)

21. Aldehydes and Ketones: Nucleophilic Addition(0)

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)

22. Carboxylic Acid Derivatives: NAS(0)

Carboxylic Acid Derivatives
(0)

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)

Review of Nitriles
(0)

23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides(0)

Intro to Thioesters
(0)

Hydrolysis of Thioesters
(0)

Hydrolysis of Phosphate Esters
(0)

Intro to Phosphate Anhydrides
(0)

Chemical Reactions of Phosphate Anhydrides
(0)

24. Enolate Chemistry: Reactions at the Alpha-Carbon(0)

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)

25. Condensation Chemistry(0)

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)

26. Amines(0)

Amine Alkylation
(0)

Gabriel Synthesis
(0)

Amines by Reduction
(0)

Nitrogenous Nucleophiles
(0)

Reductive Amination
(0)

Curtius Rearrangement
(0)

Hofmann Rearrangement
(0)

Hofmann Elimination
(0)

Cope Elimination
(0)

27. Heterocycles(0)

Nomenclature of Heterocycles
(0)

Acid-Base Properties of Nitrogen Heterocycles
(0)

Reactions of Pyrrole, Furan, and Thiophene
(0)

Directing Effects in Substituted Pyrroles, Furans, and Thiophenes
(0)

Addition Reactions of Furan
(0)

EAS Reactions of Pyridine
(0)

SNAr Reactions of Pyridine
(0)

Side-Chain Reactions of Substituted Pyridines
(0)

28. Carbohydrates(0)

Monosaccharide
(0)

Monosaccharides - D and L Isomerism
(0)

Monosaccharides - Drawing Fischer Projections
(0)

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
(0)

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
(0)

Monosaccharides - Wohl Degradation
(0)

Monosaccharides - Ruff Degradation
(0)

Disaccharide
(0)

Polysaccharide
(0)

29. Amino Acids(0)

Proteins and Amino Acids
(0)

L and D Amino Acids
(0)

Polar Amino Acids
(0)

Amino Acid Chart
(0)

Acid-Base Properties of Amino Acids
(0)

Isoelectric Point
(0)

Amino Acid Synthesis: HVZ Method
(0)

Synthesis of Amino Acids: Acetamidomalonic Ester Synthesis
(0)

Synthesis of Amino Acids: N-Phthalimidomalonic Ester Synthesis
(0)

Synthesis of Amino Acids: Strecker Synthesis
(0)

Reactions of Amino Acids: Esterification
(0)

Reactions of Amino Acids: Acylation
(0)

Reactions of Amino Acids: Hydrogenolysis
(0)

Reactions of Amino Acids: Ninhydrin Test
(0)

30. Peptides and Proteins(0)

Peptides
(0)

Primary Protein Structure
(0)

Secondary Protein Structure
(0)

Tertiary Protein Structure
(0)

Disulfide Bonds
(0)

Quaternary Protein Structure
(0)

Summary of Protein Structure
(0)

Intro to Peptide Sequencing
(0)

Peptide Sequencing: Partial Hydrolysis
(0)

Peptide Sequencing: Partial Hydrolysis with Cyanogen Bromide
(0)

Peptide Sequencing: Edman Degradation
(0)

Merrifield Solid-Phase Peptide Synthesis
(0)

31. Catalysis in Organic Reactions(0)

Introduction to Catalysis
(0)

Acid-Base Catalysis
(0)

Nucleophilic Catalysis
(0)

Metal Ion Catalysis
(0)

Metal Ion Catalysis: Water Activation
(0)

Rates of Intramolecular Reactions
(0)

Intramolecular Acid-Base Catalysis
(0)

Intramolecular Nucleophilic Catalysis
(0)

32. Lipids (0)

Intro to Lipids
(0)

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)

33. The Organic Chemistry of Metabolic Pathways(0)

Intro to Metabolism
(0)

ATP and Energy
(0)

Intro to Coenzymes
(0)

Coenzymes in Metabolism
(0)

Energy Production in Biochemical Pathways
(0)

Intro to Glycolysis
(0)

Catabolism of Carbohydrates: Glycolysis
(0)

Glycolysis Summary
(0)

Pyruvate Oxidation (Simplified)
(0)

Anaerobic Respiration
(0)

Catabolism of Fats: Glycerol Metabolism
(0)

Intro to Citric Acid Cycle
(0)

Structures of the Citric Acid Cycle
(0)

The Citric Acid Cycle
(0)

34. Nucleic Acids(0)

Intro to Nucleic Acids
(0)

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)

35. Transition Metals(0)

Electron Configuration of Elements
(0)

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)

Catalytic Allylic Alkylation
(0)

Alkene Metathesis
(0)

36. Synthetic Polymers(0)

Introduction to Polymers
(0)

Chain-Growth Polymers
(0)

Radical Polymerization
(0)

Cationic Polymerization
(0)

Anionic Polymerization
(0)

Polymer Stereochemistry
(0)

Ziegler-Natta Polymerization
(0)

Copolymers
(0)

Step-Growth Polymers
(0)

Step-Growth Polymers: Urethane
(0)

Step-Growth Polymers: Polyurethane Mechanism
(0)

Step-Growth Polymers: Epoxy Resin
(0)

Polymers Structure and Properties
(0)

20. Phenols

Oxidation of Phenols to Quinones

20. Phenols

Oxidation of Phenols to Quinones: Videos & Practice Problems

Video Lessons Practice Worksheet

Oxidation of Phenols to Quinones Practice Problems

20 problems

Problem 1Multiple Choice

Which of the following reagents can be used to oxidize phenol to quinone?

Problem 2Multiple Choice

What is the characteristic structure of a quinone?

Problem 3Multiple Choice

Why can't tertiary alcohols be oxidized to quinones like phenol?

Problem 4Multiple Choice

Which of the following best describes the structure of 1,4-benzoquinone?

Problem 5Multiple Choice

Which reagent is suitable for the reduction of 1,2-quinone to catechol?

Problem 6Multiple Choice

If phenol is oxidized to quinone, which subsequent reaction can occur to regenerate phenol?

Problem 7Multiple Choice

Given a mixture of phenol and hydroquinone, which compound would be preferentially oxidized to 1,4-quinone using dichromate?

Problem 8Multiple Choice

What is the result of reducing 1,4-benzoquinone with catalytic hydrogenation?

Problem 9Multiple Choice

What unique structural change occurs when 1,2-quinone is reduced to catechol?

Problem 10Multiple Choice

Which transformation is an example of a reduction reaction?

Problem 11Multiple Choice

Quinones are best described as:

Problem 12Multiple Choice

In 1,4-benzoquinone, which positions on the benzene ring are the carbonyl groups located?

Problem 13Multiple Choice

Which of the following describes the product of the reduction of 1,2-benzoquinone?

Problem 14Multiple Choice

In a reaction sequence, which intermediate can both phenol and hydroquinone form when oxidized?

Problem 15Multiple Choice

If catechol is oxidized to 1,2-quinone, which reagent could reduce it back?

Problem 16Multiple Choice

Which of the following is a common oxidizing agent that can transform hydroquinone to 1,4-benzoquinone?

Problem 17Multiple Choice

What feature distinguishes 1,4-benzoquinone from other quinones?

Problem 18Multiple Choice

Which of the following is a property of quinones?

Problem 19Multiple Choice

What is a key difference between the oxidation of phenol and tertiary alcohols?

Problem 20Multiple Choice

Which sequence of reactions demonstrates the reversibility between phenol and quinone?

Phenol Acidity Practice Problems Cleavage of Phenyl Ethers Practice Problems

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