ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 30, Problem 30.52P
(a) Explain why poly (vinyl alcohol) cannot be prepared by the radical 
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(a) Draw the structure of polystyrene, which is formed by polymerizing the monomer styrene, C6H5CH=CH2. (b) What monomer is used to form poly(vinyl acetate), a polymer used in paints and adhesives?
(a) Hard contact lenses, which first became popular in the 1960s, were made by polymerizing methyl methacrylate [CH2 = C(CH3)CO2CH3] to form poly(methyl methacrylate) (PMMA). Draw the structure of PMMA. (b) More comfortable softer contact lenses introduced in the 1970s were made by polymerizing hydroxyethyl methacrylate [CH2 = C(CH3)CO2CH2CH2OH] to form poly(hydroxyethyl methacrylate) (poly-HEMA). Draw the structure of poly-HEMA. Since neither polymer allows oxygen from the air to pass through to the retina, newer contact lenses that are both comfortable and oxygen-permeable have now been developed.
(a) Hard contact lenses, which first became popular in the 1960s, were made by polymerizing methyl methacrylate [CH2=C(CH3)CO2CH3] to form poly(methyl methacrylate) (PMMA). Draw the structure of PMMA. (b) More-comfortable softer contact lenses introduced in the 1970s were made by polymerizing hydroxyethyl methacrylate [CH2=C(CH3)CO2CH2CH2OH] to form poly(hydroxyethyl methacrylate) (poly-HEMA). Draw the structure of poly-HEMA. Because neither polymer allows oxygen from the air to pass through to the retina, newer contact lenses that are both comfortable and oxygen-permeable have now been developed.
Chapter 30 Solutions
ORGANIC CHEMISTRY
Ch. 30 - Prob. 30.1PCh. 30 - Prob. 30.2PCh. 30 - Prob. 30.3PCh. 30 - Draw the mechanism for the radical polymerization...Ch. 30 - Prob. 30.5PCh. 30 - Prob. 30.6PCh. 30 - Prob. 30.7PCh. 30 - Prob. 30.8PCh. 30 - Prob. 30.9PCh. 30 - Prob. 30.10P
Ch. 30 - Prob. 30.11PCh. 30 - Problem 30.12
What polymer is formed by anionic...Ch. 30 - Prob. 30.13PCh. 30 - Prob. 30.14PCh. 30 - Problem 30.15
What polyamide is formed from each...Ch. 30 - Prob. 30.16PCh. 30 - Prob. 30.17PCh. 30 - Prob. 30.18PCh. 30 - Prob. 30.19PCh. 30 - Prob. 30.20PCh. 30 - Prob. 30.21PCh. 30 - Prob. 30.22PCh. 30 - Prob. 30.23PCh. 30 - Prob. 30.24PCh. 30 - Prob. 30.25PCh. 30 - 30.26 Draw the structure of the polymer formed by...Ch. 30 - Prob. 30.27PCh. 30 - Prob. 30.28PCh. 30 - Prob. 30.29PCh. 30 - 30.30 Draw each polymer in Problem 30.29 using the...Ch. 30 - Prob. 30.31PCh. 30 - Prob. 30.32PCh. 30 - Prob. 30.33PCh. 30 - Prob. 30.34PCh. 30 - Prob. 30.35PCh. 30 - Prob. 30.36PCh. 30 - Prob. 30.37PCh. 30 - Prob. 30.38PCh. 30 - 30.39 Draw a stepwise mechanism for the...Ch. 30 - 30.40 Cationic polymerization of 3-phenylpropene ...Ch. 30 - Prob. 30.41PCh. 30 - Prob. 30.42PCh. 30 - 30.43 Although styrene undergoes both cationic and...Ch. 30 - 30.44 Rank the following compounds in order of...Ch. 30 - Prob. 30.45PCh. 30 - Prob. 30.46PCh. 30 - 30.47 Draw a stepwise mechanism for the following...Ch. 30 - 30.48 Draw a stepwise mechanism for the reaction...Ch. 30 - 30.49 Draw the products of each reaction.
a. e....Ch. 30 - Prob. 30.50PCh. 30 - Prob. 30.51PCh. 30 - 30.52 (a) Explain why poly (vinyl alcohol) cannot...Ch. 30 - 30.53 Devise a synthesis of terephthalic acid and...Ch. 30 - Prob. 30.54PCh. 30 - Prob. 30.55PCh. 30 - 30.56 Compound A is a novel poly (ester amide)...Ch. 30 - 30.57 Researchers at Rutgers University have...Ch. 30 - 30.58 Melmac, a thermosetting polymer formed from...Ch. 30 - 30.59 Although chain branching in radical...Ch. 30 - Prob. 30.60P
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- (a) Hard contact lenses, which first became popular in the 1960s, were made by polymerizing methyl methacrylate [CH; =C(CH,)CO,CH3] to form poly(methyl methacrylate) (PMMA). Draw the structure of PMMA. (b) More comfortable softer contact lenses introduced in the 1970s were made by polymerizing hydroxyethyl methacrylate [CH2=C{CH)CO,CH,CH2OH] to form poly(hydroxyethyl methacrylate) (poly-HEMA). Draw the structure of poly-HEMA. Since neither polymer allows oxygen from the air to pass through to the retina, newer contact lenses that are both comfortable and oxygen-permeable have now been developed.arrow_forward(a) Draw the structure of polystyrene, which is formed by polymerizing the monomer styrene, C6H5CH=CH2.arrow_forward3. Dacron is the brand name for the polymer that is made from ethane-1,2-diol and benzene-1,4-dicarboxylic acid. (a) What type of polymer is Dacron? (b) When the two monomers combine, what type of reaction do they undergo and what molecule is eliminated? (c) What is the name for the linkages that join the monomers together?(d) Draw the monomers and the polymer of the reaction to create Dacron. (Use a condensed structural formula in your answer.) HC-C styrene H-O-C- ethane-1,2-diol I H OH НО. 206 H -C-0-H H benzene-1.4-dicarboxylic acid.arrow_forward
- (a) Describe the polymerization of a blend of maleic anhydride and 2-methyl-1,3- propanediol in the presence of an acid catalyst. Draw a chemical reaction scheme showing the intermediate and final products that are formed. Describe the reaction conditions that you would use to maximize the yield of polymer. (b) Draw the structure of the polymer, showing the repeat unit and end groups, that is obtained when the mole ratio of maleic anhydride to diol is 0.95 (c) What is the number average molecular weight of the polymer of Part (b) when the extent of reaction of maleic anhydride is (i) 90% and (ii) 100%. (d) Describe how the structure of the polymer is altered when it is further reacted with styrene in the presence of peroxide.arrow_forwardA polymer closely related to PET is PBT, which is made from terephthalic acid and butane-1,4-diol.(a) Propose a structure for PBT and write the condensed formula for the structure.(b) What does PBT stand for? That is, what do you expect the trivial name of PBT to be?(c) Would you expect PBT to have a higher or lower melting point than PET? Justify your answer.(d) PBT, rather than PET, is used in molding because it crystallizes faster. Explain why PBT crystallizes more quickly than PET.arrow_forward(a) What is the empirical formula of cellulose? (b) Whatis the monomer that forms the basis of the cellulose polymer?(c) What bond connects the monomer units in cellulose:amide, acid, ether, ester, or alcohol?arrow_forward
- (4) Describe the synthesis of plastic especially polyethylene, 1,1- dichloroethane, and polyvinyl chloridearrow_forward1.Consider the polymerization of the following monomers: H2N- -NH2 CI (a) Draw the repeat unit of the resulting polymer. (b) Identify the two structural units comprising the repeat unit. Aramids are produced using the reaction of a benzene-1,4-diamine and a terephthaloyl dichloride.arrow_forwardPolymerization of vinyl acetate gives poly(vinyl acetate). Hydrolysis of this polymer in aqueous sodium hydroxide gives the useful water-soluble polymer poly(vinyl alcohol). Draw the repeat units of both poly(vinyl acetate) and poly(vinyl alcohol).arrow_forward
- Organic polymers can also be incinerated as a means of disposal. (a) What products are formed on combustion of polyethylene? (b) What products are formed on combustion of polyethylene terephthalate? (c) Are these reactions exothermic or endothermic? (See Sections 6.4 and 30.3 for related reactions.) (d) Propose a reason why HDPE and PET must be separated from poly(vinyl chloride) prior to incineration.arrow_forwardPoly(lactic acid) (PLA) has received much recent attention because the lactic acid monomer [CH3CH(OH)COOH] from which it is made can be obtained from carbohydrates rather than petroleum. This makes PLA a more “environmentally friendly” polyester. (A more in-depth discussion of green polymer synthesis is presented in Chapter 30.) Draw the structure of PLA.arrow_forward6. Dacron is the brand name for the polymer that is made from ethane-1,2-diol and benzene-1,4-dicarboxylic acid. (a) When the two monomers combine, what type of reaction do they undergo and what molecule is eliminated? [1] (b) What is the name for the linkages that join the monomers together? [1] (c) Draw the monomers and the polymer of the reaction to create Dacron. [3]arrow_forward
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