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

Limitations of Friedel-Crafts Alkyation

See all 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
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

Friedel-Crafts Alkylation has several limitations that render it almost useless in the lab. Let's take a look at 4 examples of what these limitations could be.

Concept #1: Limitations

Practice: Provide the major product and the correct mechanism for the following reaction. 

Practice: Provide the major product and the correct mechanism for the following reaction. 

Additional Problems
Which reaction does NOT work?
The Lewis acid catalyst in the reaction is _____:
Which aromatic substitution is prone to over-reaction (which reaction may add more than one substituent)?
Which of the following compounds can react with chloromethane and aluminum chloride?    
Would the product of this reaction be made in high yield?
Predict the major product and provide a mechanism of the following reaction.
Which of the following statements is  false regarding the limited synthetic utility of the Friedel-Crafts alkylation reaction?   A. The product is more reactive than the starting material leading to uncontrolled polyalkylation. B. There are side reactions which may result from carbocation rearrangements. C. The Friedel-Crafts alkylation reaction can only be used when there are meta-directing electron withdrawing substituents attached to the benzene ring. D. The reactivity of the haloalkane increases directly with the polarity of the C-X bond in the order C-F > C-Cl > C-Br > C-I E. Haloalkenes and haloalrenes cannot undergo reaction with benzene rings because the resultant vinyl cations and aryl cations are energetically inaccessible.
Which of the following reactions would give the product(s) indicated in substantial amounts (i.e., in greater than 50% yield)?
Which of the following reactions will not produce isopropylbenzene as the major product? A. I B. II C. III D. IV E. All of these will produce isopropylbenzene
What can be done to increase the selective formation of toluene in this reaction?
Provide the major organic product of the following.
Draw the major product(s) of the following reaction. 
Which of the following reactions would yield cumene (isopropylbenzene) as the major product?