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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)

27. Heterocycles

Reactions of Pyrrole, Furan, and Thiophene

27. Heterocycles

Reactions of Pyrrole, Furan, and Thiophene: Videos & Practice Problems

Video Lessons Practice Worksheet

Reactions of Pyrrole, Furan, and Thiophene Practice Problems

20 problems

Problem 1Multiple Choice

Which of the following compounds undergoes electrophilic aromatic substitution reactions similarly to benzene?

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Problem 2Multiple Choice

How does the presence of a heteroatom in pyrrole, furan, or thiophene influence their reactivity compared to benzene?

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Problem 3Multiple Choice

What is the first step in the electrophilic aromatic substitution mechanism?

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Problem 4Multiple Choice

Given the following compounds: benzene, pyrrole, furan, and thiophene, arrange them in order of increasing reactivity in EAS reactions.

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Problem 5Multiple Choice

Why is pyrrole more reactive than thiophene and furan in electrophilic aromatic substitution reactions?

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Problem 6Multiple Choice

During electrophilic aromatic substitution, why is substitution at the 2 position favored over the 3 position in pyrrole?

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Problem 7Multiple Choice

Which resonance structure contributes most to the stability of the intermediate during EAS at carbon 2 in furan?

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Problem 8Multiple Choice

Which factor most significantly affects the stability of intermediates in EAS reactions of thiophene?

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Problem 9Multiple Choice

Which product is expected to be the major product in the EAS reaction of thiophene with bromine?

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Problem 10Multiple Choice

How does substitution at the 2 position in furan affect aromaticity and product stability compared to substitution at the 3 position?

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Problem 11Multiple Choice

Which mechanism component is crucial for reestablishing aromaticity after electrophilic attack in EAS reactions of pyrrole?

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Problem 12Multiple Choice

Which heteroatom is present in thiophene?

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Problem 13Multiple Choice

What role does the formation of a carbocation intermediate play in the EAS mechanism?

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Problem 14Multiple Choice

In a reaction with chlorine, which compound would undergo EAS most rapidly and why?

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Problem 15Multiple Choice

Analyze why furan is more reactive than thiophene in electrophilic aromatic substitution.

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Problem 16Multiple Choice

If furan undergoes EAS, which site is favored for substitution and why?

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Problem 17Multiple Choice

Evaluate the resonance contributions during EAS at the 2-position in pyrrole versus the 3-position.

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Problem 18Multiple Choice

Which pattern of charge distribution improves the stability of intermediates in EAS reactions of pyrrole?

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Problem 19Multiple Choice

Predict the major product when furan undergoes EAS with acetic anhydride.

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Problem 20Multiple Choice

Critically evaluate how substitution at carbon 2 affects the aromaticity and stability in EAS reactions of thiophene.

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Acid-Base Properties of Nitrogen Heterocycles Practice Problems Directing Effects in Substituted Pyrroles, Furans, and Thiophenes Practice Problems

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