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
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
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
EAS: Badass Activity Chart
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

EAS Bromination and Chlorination both require complexing with a Lewis Acid Catalyst before the reaction can begin.

General Overview:

Concept #1: EAS Halogenation



Additional Problems
Using arrows to show the flow of electrons, provide a stepwise mechanism for the following reaction. IMPORTANT: Give all important resonance structures that contribute to the resonance hybrid of the cyclohexadienyl cation intermediate that is formed in this mechanism; you only need to do this once. If the cyclohexadienyl cation is consumed in a subsequent step in the mechanism, you may choose one of the resonance structures for that subsequent step and use that one.
What is(are) the product(s) when the following substance reacts with Br 2 in the presence of FeBr3? a. o-bromotoluene b. p-bromotoluene c. a mixture of o-bromotoluene (minor) and p-bromotoluene (major) d. a mixture of o-bromotoluene (major) and p-bromotoluene (minor) e. an equimolar mixture of o-bromotoluene and p-bromotoluene
Draw the first step of the Electrophilic Aromatic Substitution reaction between a diatomic halogen, AlX3, and benzene.
Draw the full arrow-pushing mechanism of EAS bromination. 
What is the mechanism of aromatic bromination?
Predict the product of the following reactions showing stereochemistry where appropriate:
Provide a detailed mechanism for the following organic reaction. Be sure to include all intermediates, resonance forms, charges and “curly” arrows for electron flow.
Predict the major organic product(s) for the following reaction. If more than one product is formed label the major product.
Select which of the following cannot be an intermediate in this reaction (there may be more than one answer)
Which structure can’t be an intermediate for the reaction shown below? 
Draw the active electrophile in the following reaction. Be sure to show the mechanism.
Supply the mechanism and structure of the major product of the following reaction. Include ALL relevant resonance structures
Supply the mechanism and structure of the major product of the following reaction.
Predict the major product for the reaction below and provide a complete mechanism.
What is produced when benzene reacts with chlorine in the presence of a catalyst?a. only chlorobenzeneb. chlorobenzene and chlorine atomsc. chlorobenzene and hydrogen chlorided. chlorobenzene and water
Predict the major organic product for each reaction. If no reaction occurs, then redraw the starting compound.