The compound shown is treated with excess bromine water. Which structure is the white precipitate formed?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

The compound is phenol. The hydroxyl group strongly activates the ortho and para positions, so bromine water, a polar solvent, substitutes all three positions without a catalyst. The product is 2,4,6-tribromophenol, a white precipitate; mono-bromophenols form only in low-polarity solvents such as

CS X_{2}

at low temperature.

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