Question

Phenol reacts with three equivalents of bromine in CCl₄(in the dark) to give a product of formula C₆H₃OBr₃. When this product is added to bromine water, a yellow solid of molecular formula C₆H₂OBr₄ precipitates out of the solution. The IR spectrum of the yellow precipitate shows a strong absorption (much like that of a quinone) around 1680cm^-1 . Propose structures for the two products.

Short answer

Formation of 2,4,4,6-tetrabromocyclohexa-2,5-dienone

Step-by-step solution

Formation of 2,4,6-tribromo phenol

Phenol reacts with three equivalents of bromine in CCl ₄(in the dark) gives 2,4,6- tribromo phenol because -OH is ortho and para director. Its chemical formula is C₆H₃Br₃O.

Formation of 2,4,4,6- tetrabromocyclohexa-2,5-dienone

2,4,6- tribromo phenol is treated with bromine water giving a yellow solid of molecular formula C₆H₂Br₄O which precipitates out of the solution.The strong absorption around indicates C=O stretching,

Formation of 2,4,4,6-tetrabromocyclohexa-2,5-dienone