Treatment of phenol with excess aqueous bromine is actually more complicated than

Chapter 22, Problem 22.29

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Treatment of phenol with excess aqueous bromine is actually more complicated than expected. A white precipitate forms rapidly, which on closer examination is not 2,4,6-tribromophenol but is instead 2,4,4,6-tetrabromocyclohexadienone. Explain the formation of this product.

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