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Chapter 22: Problem 146

Polycarbonates are a class of thermoplastic polymers that are used in the plastic lenses of eyeglasses and in the shells of bicycle helmets. A polycarbonate is made from the reaction of bisphenol A (BPA) with phosgene \(\left(\mathrm{COCl}_{2}\right)\) : polycarbonate \(+2 n \mathrm{HCl}\) Phenol \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\right)\) is used to terminate the polymer (stop its growth). a. Draw the structure of the polycarbonate chain formed from the above reaction. b. Is this reaction a condensation or an addition polymerization?

Short Answer

Expert verified
a. The structure of the polycarbonate chain formed from the reaction is: \( [\text{BPA}-\mathrm{O} - \mathrm{C}(\mathrm{O} - \mathrm{Cl}) - \mathrm{R}_{n}]- \mathrm{Phenol}\). b. This reaction is a condensation polymerization.

Step by step solution

01

Bisphenol A

Bisphenol A (\(\mathrm{C}_{15}\mathrm{H}_{16}\mathrm{O}_{2}\)) has the following structure: \[ \mathrm{H}_{2} \mathrm{C}= \mathrm{C} - \mathrm{C}=\mathrm{C}- \mathrm{H}_{2} \mathrm{O} - \mathrm{C} - (\mathrm{O} - \mathrm{C} - \mathrm{H})_{4} \]
02

Phosgene

Phosgene (\(\mathrm{COCl}_{2}\)) has the following structure: \[ \mathrm{C}(\equiv \mathrm{O})(\mathrm{Cl})_{2} \] ***Step 2: Draw the structure of the polycarbonate chain***
03

BPA and Phosgene reaction

The reaction occurs between the oxygen atom of bisphenol A and one carbon of the phosgene. The complete polycarbonate structure can be represented as: \[ [\text{BPA}-\mathrm{O} - \mathrm{C}(\mathrm{O} - \mathrm{Cl}) - \mathrm{R}_{n}]- \mathrm{Phenol} \] ***Step 3: Determine the type of polymerization***
04

Polymerization Type

As the reaction between BPA and phosgene produces \(\mathrm{HCl}\) (hydrogen chloride) as a byproduct, the reaction is a condensation polymerization.
05

Answer

a. The structure of the polycarbonate chain formed from the reaction is: \( [\text{BPA}-\mathrm{O} - \mathrm{C}(\mathrm{O} - \mathrm{Cl}) - \mathrm{R}_{n}]- \mathrm{Phenol}\). b. This reaction is a condensation polymerization.

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