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
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 Nitration requires nitric acid to react with a catalytic acid to generate a strong nitronium ion electrophile. 

Concept #1: EAS Nitration

Concept #2: Reduction of Nitro Groups

A ntiro group can be reduced to aniline with many reducing agents, as we see below:

Additional Problems
Indicate the order in which these intermediates would appear during the conversion of 1 into 4.  1) 2 → IV + 1 → III + 3 → 4 2) 1 + 2 → III + 3 → 4 3) 2 + 3 → I → IV + 1 →  III → 4 4) 3 → II + 1 + 2 → V → 4 5) 1 + 2 → V + 3 → 4  
Provide the missing product. Show only one most preferred product. Consider only monosubstitution for EAS where appropriate.
Which of these is the rate-determining step in the nitration of benzene? A) Protonation of nitric acid by sulfuric acid B) Protonation of sulfuric acid by nitric acid C) Loss of a water molecule by the protonated species to produce the nitronium ion D) Addition of the nitronium to benzene to produce the arenium ion E) Loss of a proton by the arenium ion to form nitrobenzene
Which structure represents a major intermediate in the nitration of toluene?
Draw the cationic intermediate in the following EAS reaction. What is the name of this class of reactive intermediates?Benzene and the nitronium cation
Provide a detailed mechanism for the following organic reaction. Be sure to include all intermediates, resonance forms, charges and “curly” arrows for electron flow.
The electrophile in the nitration reaction of benzene is: A. NO2+ B. HNO3 C. NO3+ D. H2SO3 E. NO2
Draw the active electrophile in the following reaction. Be sure to show the mechanism.
What is produced when benzene reacts with nitric acid in the presence of a catalyst?a. only nitrobenzeneb. nitrobenzene and NOc. nitrobenzene and NO2d. nitrobenzene and water
Draw the major product(s) that result from the following reaction. Do not draw inorganic side products.