Radical Bromination of Aromatic Compounds

Very Hard Organic Chemistry Aromatic Compounds

Aromatic compounds are characterized by their stability and unique reactions due to the presence of conjugated pi systems. Consider a hypothetical aromatic compound, compound X, which consists of a six-membered carbon ring with alternating double bonds, featuring a bromine substituent on one of the carbons. If compound X undergoes a radical bromination reaction, which of the following products is most likely generated from this reaction?

A six-membered brominated aromatic compound with a bromine substituent on the same carbon as the original bromine.

A brominated compound featuring a new bromine atom at the para position to the original bromine.

A biphenyl compound resulting from coupling of two aromatic rings.

A compound that results in the formation of a saturated six-membered ring with two bromine substituents.

Hint

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