Anthracene

Structure of Anthracene:

• It is a polycyclic aromatic hydrocarbon with three fused benzene rings arranged in a linear structure.
• The molecular formula is C14H10​, and it is isomeric with phenanthrene.

Synthesis of Anthracene:

• From Coal Tar:

  • Anthracenes are also isolated from the high boiling fraction of coal tar.

• Laboratory Synthesis (Elbs Reaction):

  • Cyclodehydration: Ortho-benzoyltoluene is cyclodehydrated to form anthracenes.
  • Aromatization: The intermediate is aromatized to produce anthracenes.
  • the intermediate is aromatized to produce anthracenes.

    • O-Benzoyltoluene → Cyclodehydration → Anthracenes

Reactions of Anthracene:

• Electrophilic Substitution:

  • Nitration: Anthracenes react with nitric acid to form 9-nitroanthracene.
    • C14H10 + HNO3 → H2SO4 (reagents) → C14H9NO2 + H2O
  • Sulfonation: Anthracenes react with sulfuric acid to form anthracene sulfonic acid.

    • C14H10 + H2SO4 (reagents) → C14H9SO3H + H2O

• Oxidation:

  • Anthracenes can be oxidized to anthraquinone using chromic acid or other strong oxidizing agents.

    • C14H10 + 2[O] → C14H8(O)2

Derivatives:

1. Anthraquinone: An important industrial chemical used in the production of dyes and hydrogen peroxide.
2. Dyes: Anthracene derivatives are the basis of various dyes, especially anthraquinone dyes.

Medicinal Uses:

• Anthraquinone Derivatives: Many anthraquinone derivatives are used in medicine as laxatives (e.g., senna, cascara), and some have been studied for their anti-cancer properties.

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