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

When two or more substituents are already on benzene, there are multiple new factors we must take into account. These include Steric Effects, Synergistic Groups, and Competitive Groups.

Concept #1: EAS with Polysubstituted Benzene

Practice: Which is NOT a possible product of the reaction?

Practice: Which is not a possible product of the reaction?

Additional Problems
What would you expect to be the major product obtained from the following reaction? A) I B) II C) III D) IV E) Equal amounts of II and IV
Complete the following reaction supplying the missing product and showing correct regio- and stereochemistry where applicable. If a racemic or diastereomeric mixture forms show all stereoisomers; if no reaction takes place, write N.R.
Which would be the major product(s) of the following reaction? A) I B) II C) III D) I and II in roughly equal amounts E) I and III in roughly equal amounts
What would you expect to be the major product obtained from the monobromination of m-dichlorobenzene? A) I B) II C) III D) Equal amounts of I and II E) Equal amounts of I, II and III
Which is the best prediction of the site(s) of substitution when 3-methylphenol is nitrated? A) C-2 B) C-4 C) C-5 D) C-6 E) C-4 and C-6
Which of these compounds gives essentially a single product on electrophilic substitution of a third group? A) p-chlorotoluene B) m-ethylanisole C) 1-bromo-2-chlorobenzene D) m-xylene E) 3-hydroxybenzoic acid
Predict the major product for the following reaction paying attention to the regio- and stereochemistry.
Predict the major product for each of the following reactions paying attention to the region- and stereochemistry. If there is no reaction, write just “No Reaction.”  
Predict the major product for each of the following reactions paying attention to the region- and stereochemistry. If there is no reaction, write just “No Reaction.”    
Predict the major product of the following reaction. 
What major product would you expect from the following reaction?
What is the product of 3-bromo-2-nitroanisole reacting with fuming sulfuric acid?
Predict the major organic products of the following reactions or write N.R. for no reaction.
Complete the following reaction with the correct structure of the product(s). Don’t forget to specify the stereochemistry.
Predict the major product for the following reaction paying attention to the regio- and stereochemistry.  
What would you expect to be the major product(s) obtained from the following reaction?
Provide the major product for the following transformation
Provide the major product for the following transformation
Provide the major product for the following transformation
Provide the major product for the following transformation
Predict the major product for the following reaction.