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Chapter 17: Q71P (page 910)

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 C6H2OBr4precipitates 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

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Formation of 2,4,6-tribromophenol

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

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01

Formation of 2,4,6-tribromo phenol

Phenol reacts with three equivalents of bromine in CCl4(in the dark) gives 2,4,6- tribromo phenol because -OH is ortho and para director. Its chemical formula is C6H3Br3O.

Formation of 2,4,6-tribromophenol

02

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 1680cm-1 indicates C=O stretching,

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

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Most popular questions from this chapter

Triphenylmethanol is insoluble in water, but when it is treated with concentrated sulfuric acid, a bright yellow solution results. As this yellow solution is diluted with water, its color disappears and a precipitate of triphenylmethanol reappears. Suggest a structure for the bright yellow species, and explain this unusual behavior.

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

Predict the major products of treating the following compounds with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.

(a) isopropylbenzene

(b) p-xylene

(c) tetralin

What products would you expect from the following Suzuki coupling reactions?

The antioxidants BHA and BHT are commonly used as food preservatives. Show how BHA and BHT can be made from phenol and hydroquinone.
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