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Chapter 17: 71P (page 845)

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

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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 CCl 4(in the dark) gives 2,4,6- tribromo phenol because -OH is ortho and para director. Its chemical formula is C6H3Br3O.

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 indicates C=O stretching,

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

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Most popular questions from this chapter

Phenolphthalein, a common nonprescription laxative, is also an acid-base indicator that is colorless in acid and red in base. Phenolphthalein is synthesized by the acid-catalyzed reaction of phthalic anhydride with 2 equivalents of phenol.

(a) Propose a mechanism for the synthesis of phenolphthalein.

(b) Propose a mechanism for the conversion of phenolphthalein to its red dianion in the base.

(c) Use resonance structures to show that the two phenolic oxygen atoms are equivalent (each with half a negative charge) in the red phenolphthalein dianion.


Phthalic anhydride Phenolphthalein red dianion

Starting from toluene, propose syntheses for ortho-, meta-, and para-chlorobenzoic acid.

What products would you expect from the following coupling reactions?

(a)

(b)

(c)

(d)

(e)

Predict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark.

(a)

(b)

(c)

Predict the site(s) of electrophilic attack on these compounds.

(a)

(b)
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