Chapter 26: Q2P (page 1326)
Propose a mechanism for reaction of the first three propylene units in the polymerization of propylene in the presence of benzoyl peroxide.

Short Answer

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Chapter 26: Q2P (page 1326)
Propose a mechanism for reaction of the first three propylene units in the polymerization of propylene in the presence of benzoyl peroxide.


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The polyester named LactomerRis an alternating copolymer of lactic acid and glycolic acid. Lactomer is used for absorbable suture material because stitches of Lactomer hydrolyze slowly over a two-week period and do not have to be removed. The hydrolysis products, lactic acid and glycolic acid, are normal metabolites and do not provoke an inflammatory response. Draw the structure of the Lactomer polymer.

Explain why the addition of a small amount of glycerol to the polymerization mixture gives a stiffer urethane foam.
Olestra®is a fat-based fat substitute that became available in snack foods such as potato chips in 1998. Previous fat substitutes were carbohydrate-based or protein-based mixtures that did not give as good a sensation in the mouth and are not suitable for frying. With Olestra®, the glycerol molecule of a fat is replaced by sucrose (p. 1237). In Olestra®, the sucrose molecule has six, seven, or (most commonly) eight fatty acids esterified to its hydroxy groups. The fatty acids come from hydrolysis of vegetable oils such as soybean, corn, palm, coconut, and cottonseed oils. This unnaturally bulky, fat-like molecule does not pass through the intestinal walls, and digestive enzymes cannot get close to the sucrose center to bind it to their active sites. Olestra® passes through the digestive system unchanged, and it provides zero calories.Draw a typical Olestra® molecule, using any fatty acids that are commonly found in vegetable oils.
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.
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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