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Answer on Organic Chemistry Question for Lilly

Question #17992
Phenols show a negative reaction for triidomethane test. However, when I did the experiment, phenol+iodine solution+ NaOH drop by drop + warm, I noticed that the brown colour of iodine solution was decolourised and a cloudy solution with orange droplets. The smell was that of like vinegar. This shows a negative iodoform test as no yellow precipitate was formed. Since the solution added was iodine solution and not an alkyl halide, what could the product be? I do not understand the mechanism behind the reaction. Could you please explain. Thank you.
Expert's answer
When heated with of iodine phenol in the presence of caustic alkali sediment forms tetra-iodo-diphenylene-dioxide (C6H4I2O)2.

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