Chapter 26: Q7P (page 1328)
Draw the important resonance forms of the stabilized anion formed in the anionic polymerization of methyl acrylate.
Short Answer

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Chapter 26: Q7P (page 1328)
Draw the important resonance forms of the stabilized anion formed in the anionic polymerization of methyl acrylate.

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Cholic acid, a major constituent of bile, has the structure shown.
(a) Draw the structure of cholic acid, showing the rings in their chair conformations, and label each methyl group and hydroxy group as axial or equatorial. (Making a model may be helpful.)
(b) Cholic acid is secreted in bile as an amide linked to the amino group of glycine. This cholic acid-amino acid combination acts as an emulsifying agent to disperse lipids in the intestines for easier digestion. Draw the structure of the cholic acid-glycine combination and explain why it is a good emulsifying agent.

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.

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.
Draw the structure of isotactic poly(acrylonitrile) and syndiotactic polystyrene.
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.
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