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Chapter 30: Question 30.47 (page 1227)

Draw a stepwise mechanism for the following reaction, which is used to prepare bisphenol A (BPA), a widely used monomer in polymer synthesis.

Short Answer

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Answer

Mechanism of the reaction

Step by step solution

01

Bisphenol A

The simplest bisphenol synthesized by reacting two phenol molecules with acetone in the presence of acids is bisphenol-A. This organic compound has good solubility in organic solvents but poor solubility in water.

02

About the mechanism

When sulfuric acid is treated with acetone, a carbocation will be formed. This carbocation is treated with phenol that results in a dihydroxy compound.

Formation of dihydroxy compound

03

Addition of second phenol molecule

The obtained dihydroxy compound is treated with acid again, and water is removed. As a result, carbocation is formed. It is treated with another phenol molecule that leads to the formation of bisphenol A. The mechanism is shown below.

Formation of bisphenol A

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Most popular questions from this chapter

Draw the structures of Quiana and Nomex, two commercially available step-growth polymers formed from the given monomers. Nomex is a strong polymer used in aircraft tires and microwave transformers. Quiana has been used to make wrinkle-resistant fabrics.

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Draw the structure of the polymer formed by chain-growth polymerization of each monomer.

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What polymer is formed by chain-growth polymerization of each monomer?

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What polymer is formed by the anionic polymerization of each monomer?

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Explain why aqueous NaOH solution can be stored indefinitely in polyethylene bottles, but spilling aqueous base on a polyester shirt or nylon stockings quickly makes a hole.
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