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Furan is a heterocyclic aromatic compound with the formula C4H4O. It's a five-membered ring containing one oxygen atom and four carbon atoms.
Preparation:
Furan Synthesis:
Paal-Knorr synthesis: This is a common method for preparing furans. It involves the reaction of 1,4-dicarbonyl compounds with a dehydrating agent like acid.
Feist-Benary synthesis: This method involves the condensation of α-halo ketones with β-keto esters.
Other methods: Furan can also be prepared by reacting 1,3-butadiene with oxygen.
Reactions:
Electrophilic Aromatic Substitution: Like other aromatic compounds, furan undergoes electrophilic aromatic substitution reactions at the 2 and 5 positions. Common electrophilic reagents include:
Halogenation: With bromine or chlorine.
Nitration: With nitric acid.
Sulfonation: With sulfuric acid.
Diels-Alder Reactions: Furan can act as a diene in Diels-Alder reactions, forming cyclic adducts.
Ring Opening: Under harsh conditions, furan's ring can be opened by reactions like oxidation or reduction.