Ch. 18 - Reactions of Aromatics: EAS and BeyondSee 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

Electron Withdrawing Groups

See all sections
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

Adding a single group to a benzene ring is the first step. Now, what happens if we want to do a second reaction on that benzene. Where is it going to add? This is the question we will be answering.

Concept #1: Activity and Directing Effects

Concept #2: Badass Activity Chart

Practice: Predict the major product of the following EAS reaction.

Practice: Predict the product of the following multi-step synthesis. 

Additional Problems
In electrophilic aromatic substitution reactions a bromine substituent: a. a is a deactivator and a m-director b. b is a deactivator and an o,p-director c. c is an activator and a m-director d. is an activator and an o,p-director e. none of the above
Which of the following compounds reacts most slowly during nitration?
In electrophilic aromatic substitution reactions the hydroxyl group is an o,p-director because: a. it donates electron density to the ring by induction and destabilizes the meta sigma complex b. it donates electron density to the ring by resonance and stabilizes the ortho and para sigma complexes c. it donates electron density to the ring by induction and stabilizes the ortho and para sigma complexes d. it donates electron density to the ring by resonance and destabilizes the meta sigma complex e. it withdraws electron density from the ring by induction and destabilizes the meta sigma complex
Which one of the following compounds will be least reactive towards Friedel-Crafts reaction? a. nitrobenzene b. anisole c. phenol d. benzene e. chlorobenzene
Which compound is more reactive than benzene in electrophilic aromatic substitution reaction?   a. benzaldehyde b. nitrobenzene c. toluene d. benzoic acid e. benzenesulfonic acid
It's dipole roundup! Indicate which of the molecules have EDGs with an asterisk, EWGs with a check mark, o,p-directors with a circle, and meta-directors with a square. 
Circle the benzene rings with a deactivating group. Star (*) the benzene rings with an ortho/para‐directing group. 
Circle the compound that would react the fastest in a typical electrophilic aromatic substitution reaction (most activated aromatic ring)   
Which one of the following would most readily undergo electrophilic aromatic substitution with an electrophile E+?
The major product of the following reaction is 
Rank 1, 2, 3 and 4 (1 = fastest to 4 = slowest) the following compounds in order of reactivity toward electrophilic aromatic substitution by writing in the number below each structure.
Which reagent would you use to carry out the following transformation?tert-butylbenzene → p-tert-butylbenzenesulfonic acid   +   o-tert-butylbenzenesulfonic acid A) HNO3 / H2SO4B) tert-C4H9Cl / AlCl3C) H2SO3 / peroxidesD) SO3 / H2SO4E) SO2 / H2SO3
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.”  
Which one of the following compounds would be most reactive toward electrophilic aromatic substitution?
Methyl p-nitrobenzoate has been found to undergo saponification (hydrolysis) faster than methyl benzoate. a. Consider the mechanism of saponification, and explain the reason for this rate enhancement.      b. Would you expect methyl p-methoxybenzoate to undergo saponification faster or slowerthan methyl benzoate? WHY?
Which of the following is the major product of the reaction below?
Which of the following compounds is most deactivated toward elimination-addition Electrophilic Aromatic Substituted with an electrophile E+?
Supply the mechanism and structure of the major product of the following EAS reaction.
Which compound has the slowest rate toward an electrophilic aromatic substitution reaction?a) chlorobenzeneb) toluenec) benzened) nitrobenzenee) anisole
Which substituents would deactivate benzene toward electrophilic aromatic substitution reactions?
Complete the following reaction by drawing the structure of the principal major product. Indicate relative stereochemistry where necessary. If there is no reaction, write NR.
Which statement best describes why anisole brominates faster than benzene?A) The inductive effect of the methoxy group stabilizes the cationic intermediate.B) The inductive effect of the methoxy group stabilizes the anionic intermediate.C) The resonance effect of the methoxy group stabilizes the cationic intermediate. D) The resonance effect of the methoxy group stabilizes the anionic intermediate. 
Complete the following reaction by drawing the structure of the principal major product. Indicate relative stereochemistry where necessary. If there is no reaction, write NR.
Provide the expected major product (One-Step EAS):
Provide the expected major product (One-Step EAS):
Provide the expected major product (One-Step EAS):
Draw the major organic product(s) for the following reaction. Multiple products may be drawn in one box, in any order. Use an expanded octet around sulfur to avoid formal charges.
Draw the major product(s) that result from the following reaction. Do not draw inorganic side products.
Draw the structure of the expected major organic product if this compound was to undergo monobromination with Br2/FeBr3. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading. In cases where there is more than one answer, just draw one. Do not draw organic or inorganic by-products.
Give the structures of the two major products in the following reaction.
Predict the major product for the following reaction.
The following compounds are treated with HNO3/H2SO4. Predict the positions of electrophilic attack that lead to the major nitration product(s). 
For the following reaction, draw the major organic product(s). Do not draw inorganic side products.
Draw the major organic product(s) for the following Friedel-Crafts acylation reaction: 
Draw the major organic product(s) for the following reaction. Multiple products may be drawn in one box, in any order. Include charges as needed.
What is (are) the product(s)?
Draw structural formulas for the major organic product(s) of the reaction shown below.
Draw the structure of the product in the following reaction of aniline with CH3CI in the presence of AICI3. Be sure to show formal charges, if applicable.
Draw the major product(s) that result from the following reaction. Do not draw inorganic side products.
Draw the major organic product(s) for the following reaction. Multiple products may be drawn in one box, in any order. Use an expanded octet around sulfur to avoid formal charges.