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Chapter 26: Q17P (page 1336)

Bisphenol A is made on a large scale by a condensation of phenol with acetone. Suggest an appropriate catalyst, and propose a mechanism for this reaction. (Hint: This is a condensation because three molecules are joined with loss of water. The mechanism belongs to another class of reactions though.)

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complete mechanism for the reaction

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01

Bisphenol A (BPA)

It is a common intermediate in polyester and polyurethane synthesis. BPA is primarily used in the production of polycarbonate plastics. BPA enhances rigidity when added to plastic resins.

02

Condensation polymerization

In this process, a large number of monomer molecules combine together usually with the loss of simple molecules like water, alcohol, ammonia, carbon dioxide, hydrogen chloride etc., to form a polymer in which the molecular formula of the repeat unit is not the same as that of the monomer.

03

Mechanism

The reaction is catalyzed by a strong acid such as hydrochloric acid (HCl).

This reaction proceeds via electrophilic attack of the proton from the acidic catalyst to the acetone molecule.

In the final step, loss of water molecule takes place to give the final product as bisphenol A (BPA).

complete mechanism for the reaction

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Most popular questions from this chapter

Propose a mechanism for reaction of the first three propylene units in the polymerization of propylene in the presence of benzoyl peroxide.

Explain why the addition of a small amount of glycerol to the polymerization mixture gives a stiffer urethane foam.

One of the earliest commercial plastics was BakeliteR, formed by the reaction of phenol with a little more than one equivalent of formaldehyde under acidic or basic conditions. Bayer first discovered this reaction in 1872, and practical methods for casting and molding. Bakelite were developed around 1909. Phenol-formaldehyde plastics and resins (also called phenolics) are highly cross-linked because each phenol ring has three sites (two ortho and one para) that can be linked by condensation with formaldehyde. Suggest a general structure for a phenol-formaldehyde resin, and propose a mechanism for its formation under acidic conditions. (Hint: Condensation of phenol with formaldehyde resembles the condensation of phenol with acetone, used in Problem 26-17, to make bisphenol A.)

The mechanism given for cationic polymerization of isobutylene (Mechanism 26-2) shows that all the monomer molecules add with the same orientation, giving a polymer with methyl groups on alternate carbon atoms of the chain. Explain why no isobutylene molecules add with the opposite orientation.

Chain branching occurs in cationic polymerization much as it does in free-radical polymerization. Propose a mechanism to show how branching occurs in the cationic polymerization of styrene. Suggest why isobutylene might be a better monomer for cationic polymerization than styrene.

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