A high-boiling liquid, bp 202–204°C burns with a yellow, sooty flame. Sodium fusion indicates that halogens, nitrogen, and sulfur are not present. The compound is not soluble in water, dilute sodium bicarbonate solution, or dilute hydrochloric acid. However, it proved to be soluble in 5% aqueous sodium hydroxide solution. The compound gives a purple color with ferric chloride solution and a precipitate when reacted with bromine–water. Treatment with hydroxylamine reagent did not give a reaction, but a white precipitate was obtained when the compound was treated with α-napthylisocyanate. On drying, this white, solid derivative had an mp 127–129°C. Identify the original liquid and write a structure for the solid derivative. After identifying the unknown liquid, can you indicate what the structure of the precipitate obtained on reaction with bromine might be?
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