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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 a stepwise mechanism for the conversion of dihalide A and cyclohexane-1,4-diol to polyether B in the presence of AlCl3.

Compound A is a novel poly(ester amide) copolymer that can be used as a bioabsorbable coating for the controlled release of drugs. A is a copolymer of four monomers, two of which are amino acids or amino acid derivatives. The body’s enzymes recognize the naturally occurring amino acids in the polymer backbone, allowing for the controlled enzymatic breakdown of the polymer and steady release of an encapsulated drug. Identify the four monomers used to synthesize A; then use Figure 29.2 to name the two amino acids.

Poly(ester amide) A

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

(a.)

(b.)

In addition to glycolic and lactic acids (Section 30.6B), dissolving sutures can also be prepared from each of the following lactone monomers. Draw the structure of the polymer formed from each monomer.

(a.)

(b.)

Explain why styrene can be polymerized to polystyrene by all three methods of chain-growth polymerization.
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