Wheel of Electrophilic Aromatic Substitutions

An organic reaction in which an atom attached to an aromatic system (usually hydrogen) is substituted by an electrophile is referred to as electrophilic aromatic substitution (SEAr or EAS).


Direct or indirect introduction of functional groups to the benzene ring is possible by the EAS.



Wheel of Electrophilic Aromatic Substitutions: Click/tap to enlarge the image

Reaction type -> Product (on the infographic):

  1. Bromination -> Bromobenzene
  2. Chlorination -> Chlorobenzene
  3. Iodination -> Iodobenzene
  4. Nitration -> Nitrobenzene
  5. Amination -> Aniline (multistep: 1. Nitration 2. Reduction)
  6. Methylation (Friedel-Crafts alkylation) -> Toluene
  7. Friedel-Crafts alkylation -> Cumene
  8. Friedel-Crafts acylation -> Propiophenone
  9. Alkylation -> n-Propylbenzene (multistep: 1. Friedel-Crafts acylation 2. Clemmensen reduction)
  10. Friedel-Crafts alkylation -> t-Butylbezne
  11. Friedel-Crafts acylation -> Benzophenone
  12. Friedel-Crafts acylation -> 3-Benzoylpropionic acid
  13. Friedel-Crafts alkylation -> Cyclohexylbenzene
  14. Sulfonation -> Benzene sulfonic acid
  15. Hydroxylation -> Phenol (multistep: 1. Sulfonation 2. Acid-base reaction followed by fusion with alkali 3. Acidification)
  16. Carboxylation -> Benzoic acid (multistep: 1. Methylation (Friedel-Crafts alkylation) 2. Oxidation)
  17. Hydroxymethylation -> Benzyl alcohol (multistep: 1. Blanc chloromethylation or Blanc halomethylation 2. Hydrolysis (nucleophilic substitution))
  18. Blanc chloromethylation or Blanc halomethylation -> Benzyl chloride
  19. Formylation (Vilsmeier-Haack formylation or Vilsmeier-Haack-Viehe reaction) -> Benzaldehyde
  20. Diazotization -> Benzene diazonium cation (multistep: 1. Nitration 2. reduction 3. Griess diazo reaction)

What other wheel(s) 🛞 of organic reactions would you like to see ❓Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

References:

(1)    Roman A. Valiulin, ChemInfoGraphic. ChemInfoGraphic. https://cheminfographic.wordpress.com.

(2)    Brown, C.; Ford, M. Higher Level Chemistry, 2nd ed.; Pearson Education: Harlow, Essex, 2014.

(3)    Ncert. Chemistry : Textbook for Class XI - Part.II; National Council Of Educational Research And Training: New Delhi.

(4)    Graham, T. W.; Fryhle, C. B.; Snyder, S. A. Organic Chemistry.; Hoboken, Nj John Wiley Et Sons, Inc, 2016.

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