Buy Now the Hard Copy of notes for seamless and ad-free learning, Click Below!
Structure of Anthracene
Anthracene 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
From Coal Tar
Anthracene is also isolated from the high boiling fraction of coal tar.
Laboratory Synthesis (Elbs Reaction):
Cyclodehydration: Ortho-benzoyltoluene is cyclodehydrated to form anthracene.
Aromatization: The intermediate is aromatized to produce anthracene.
the intermediate is aromatized to produce anthracene.
O-Benzoyltoluene → Cyclodehydration → Anthracene
Reactions
Electrophilic Substitution
Nitration: Anthracene reacts with nitric acid to form 9-nitroanthracene.
C14H10 + HNO3 → H2SO4 (reagents) → C14H9NO2 + H2O
Sulfonation: Anthracene reacts with sulfuric acid to form anthracene sulfonic acid.
C14H10 + H2SO4 (reagents) → C14H9SO3H + H2O
Oxidation
Anthracene can be oxidized to anthraquinone using chromic acid or other strong oxidizing agents.
C14H10 + 2[O] → C14H8(O)2
Derivatives
Anthraquinone: An important industrial chemical used in the production of dyes and hydrogen peroxide.
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.
Buy Now the Hard Copy of notes for seamless and ad-free learning, Click Below!
