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Friedel-Crafts Alkylation

Friedel-Crafts Alkylation (Electrophilic Aromatic Substitution Aromatic.) Converts c1ccccc1 to c1ccccc1C(C)C using (CH₃)₂CHCl, AlCl₃.

Aromatic

Reaction details

Name

Friedel-Crafts Alkylation

Type

Aromatic

Subtype

Electrophilic Aromatic Substitution

Starting Material

c1ccccc1

Product

c1ccccc1C(C)C

Reagents
  • (CH₃)₂CHCl

  • AlCl₃

Mechanism
  1. Smiles

    c1ccccc1

    Description

    Benzene

  2. Smiles

    c1ccccc1

    Description

    AlCl₃ + RCl → R⁺ (carbocation)

  3. Smiles

    c1ccccc1C(C)C

    Description

    Isopropylbenzene (cumene)

Tips
  1. Carbocation can rearrange!

  2. Product more reactive than starting material → polyalkylation

  3. Does NOT work on deactivated rings (nitrobenzene)

  4. AlCl₃ catalyst

Related Reactions
  • friedel-crafts-acylation

This is one row of the Reaction roadmap sheet - print all 83 reactions on one page.