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Chapter 26: Q14P (page 1335)
Kodel庐 polyester is formed by transesterification of dimethyl terephthalate with 1,4-di(hydroxymethyl)cyclohexane. Draw the structure of Kodel.
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(a) Propose a mechanism for the reaction of bisphenol A with phosgene.
(b) Diethyl carbonate serves as a less-toxic alternative to phosgene for making Lexan. Propose a mechanism for the transesterification of diethyl carbonate with bisphenol A, catalyzed by a trace of sodium ethoxide. What small molecule is given off in this condensation?
Compare the molecular structures of cotton and polypropylene, the two major components of thermal underwear. One of these gets wet easily and holds the water in contact with the skin. The other one does not get wet, but wicks the water away from the skin and feels relatively dry to the touch. Explain the difference in how these two fabrics respond to moisture.
. Poly (trimethylene carbamate) is used in high-quality synthetic leather. It has the structure shown.
(a) What type of polymer is poly (trimethylene carbamate)?
(b) Is this a chain-growth polymer or a step-growth polymer?
(c) Draw the products that would be formed if the polymer were completely hydrolyzed under acidic or basic conditions.
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.)
Explain why the addition of a small amount of glycerol to the polymerization mixture gives a stiffer urethane foam.
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