Ch. 18 - Reactions of Aromatics: EAS and BeyondWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins
Sections
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
Birch Reduction
EAS: Sequence Groups
EAS: Retrosynthesis
Diazo Replacement Reactions
Diazo Sequence Groups
Diazo Retrosynthesis
Nucleophilic Aromatic Substitution
Benzyne
Additional Practice
EAS: Sulfonation Mechanism
EAS: Gatterman–Koch Reaction
EAS: Total Benzene Isomers
EAS: Polycyclic Aromatic Hydrocarbons
EAS: Directing Effects
Resonance Theory of EAS Directing Effects
Activated Benzene and Polysubstitutions
Clemmensen Reduction
EAS: Dueling Benzenes
Hydrogenation of Benzene
EAS: Missing Reagent
EAS: Synthesis
Diazonization of Aniline
Diazo Coupling Reactions
SNAr vs. Benzyne
Aromatic Missing Reagent
Aromatic Synthesis
Aromatic Retrosynthesis
EAS on 5-membered Heterocycles

This next group of EAS Reactions is grouped together because they share a common active electrophile: a carbocation. Popular carbocations include those catalyzed by hydrofluoric acid and promoted by boron trifluoride

Concept #1: Any Carbocation

Additional Problems
Use arrow pushing to show the mechanism that accounts for the formation of the product.
Consider the following reaction: a. Draw the structure of the major product. b. Illustrate the mechanism. Indicate all electron movements and the structures of all intermediates.    
Provide the reagents to accomplish the transformation below. More than one step might be required for the transformation. 
Provide the reagents to accomplish the transformation below. More than one step might be required for the transformation. 
Predict the product of the following reaction. 
Predict the major product for the reaction, paying attention to the regio- and stereochemistry where necessary.
For the reaction below, draw the structure of the appropriate compound in the box. Indicate stereochemistry where it is pertinent. For Friedel Crafts reactions, assume that the major product is the least sterically hindered one.
When the allylic alcohol below is treated with a strong Lewis acid (BF 3) in the presence of resorcinol, an electrophilic aromatic substitution occurs. Provide a plausible mechanism for this transformation.
Provide the missing product. Show only one most preferred product. Consider only monosubstitution for EAS where appropriate.
Predict the major product for the following reaction paying attention to the regio- and stereochemistry. 
Propose a detailed mechanism for the following reaction:
Which of these reactions would produce  tert-butylbenzene in high yield?
Draw the cationic intermediate in the following EAS reaction. What is the name of this class of reactive intermediates?Benzene and tertiary butyl carbocation
Provide detailed mechanisms for the following reaction. Clearly show the formation of the appropriate electrophile and all intermediates. (It is not necessary to depict all the resonance forms of the arenium ions in this problem.)
Provide the missing reagents to complete the following transformation (hint: a catalyst and two alkyl halides are needed).
Which of the following is the likely outcome from this reaction?
Draw the product of the reaction.
What is the major product formed from the following reaction? a. product c b. product b c. product dd. product a