Polyisbutylene is neo the component of buy rubber wed for making ines bes. {@) Give the scare of pobynobuyee {@) iets an ation polymer oa condensation polymer? {@) What conditions eaten. anions feud would be most pprprate for polymerization of isobutylene? Explain your ser Polyhloopene conmonly kno a neoprene, is widely ied in wetsuits din uber ha parts that must withstand exposure to gasoline oro solves ( ) cy 1] {@)_ Is neoprene an addition polymer or a condensation polymer? C=C—CHy (by What monomer is usd to make tis synthetic rubber? palychloropren eoprene) PPolytimesbylene carbamate) is used in bigh-qualitysymthetic leather. I has the structure shown, HO 2) What ype of polymer is ply(imerylene carbamate)? if () Isthisa chaimgrowrh polymer ora step-growth polymer? CH,CH.CH,—N—C—OF (©) Draw the proshiets that would be formed ifthe polymer were completely hycirolyzed under cide or basie conditions poly(trimethylene carbamate) Fly opine) pcos pl mati Ce Sagas sae ° 9 Go) War ype ofpulymer plytwylen tephialae? LE CH,CH,CH,CH,—o— 4O)-!-0 (@) Js this an addition polymer or a condensation polymer? I canescens sane wirtnen ‘hitbalymer an how the plymerztion ag be potions rebate) comple, erica etarmtnttermtectertemice ‘UV Light and aqueous acid and base. Urylon has the structure shown. (a) What functional group is contained inthe Urylon structure? {(b) Is Urylon a chain-growth polymer ora step-growth polymer? (©) Draw the products that would be formed if the polymer were completely hydrolyzed under acidie or basic conditions Polyethylene glycol, of Carboweax® (—O—CH,—CH,— ‘packaging additive for foods. (a) What type of polymer is polyethylene glycol? (We have not scen tis type of polymer before.) (b) The systematic name for polyethylene glycol is polyethylene oxide). What monomer woul! you use to make polyethylene glycol? (©) What conditions ({ree-radical initiator, acid catalyst, basic catalyst, ee.) would you consider using in this polymerization? (@) Propose a polymerization mechanism as far asthe tetramer. Ring-opening metathesis polymerization (ROMP, sce Section 8-17) is a promising new technique for polymer cyclic olefins. In its simplest form, the reaction involves a cycloalkene (preferably with some ing srain vo drive the ‘eaction) whose double honds undergo metathesis (a trading of partners at the ends ofthe double bonds) 1 give a polymer containing both single and double bonds Op ste Aw monomer polymer" is widely used as a binder, thickening ageat, and ‘ring-opening metathesis polymerization (ROMP) ‘Show which monomers might have reacted to produce the following polymers: Polyoxymethylene (polyformaldchyde) is the tough, selfubricating Delrin® plastic used in gear wheels (@) Give the structure of polyformaldedyde. {(b) Formaldehyde is polymerized using an acidic catalyst Using HI asa catalyst, propose a mechanisea for the ‘polymerization as far asthe trimer. (©) Is Delrin an addition polymer or a condensation polymer?262s Reyne i ane cf te cemiponents of bay ier id or tng nner ne (2) Give te arts of pytenlee. (0) Isis an ation polymer o condensation polynes? {6} Whatcondtows cans son, rfc) would he ms pcp fr plynesztion of sb? Explain your arse eyehloprne,conuennly Ene epee, wily dn wt sein aber © urs hat must wtstand expose to gslieo ote sles (, ) 1 {@) Is negrene an aition pyre ora condensation polymer? Ciy-C=C— cy () Whot monomer is used to make ths sti rubber? paljclomprens (open) Polysimetylene carbamate is sedi hghqaitysyheticether I has the structure shown, no (a) What pe of polymer poly rimaylene erbamate)? 19 (©) Isthis a chaingrowth polymer or a tep-growth polymer? CHEK -N—C— OF (6) raw he product that would be formed if the polymer were completly hyelyzell under aie or has conditions. poly(vimey lene cabanate Poly(butyene erphalt) ia dopo plastic material SS TAY © Warpretpmerparooac eine — foLccHcH—o-e bo Win le pce conse (6) Suggest what monomers might be used syetiesize tyes ‘rept in fajaer auton plyncnen night petaene fetal) accomplised ‘Vr ies ae usd in pee miu sing ne because the polymers elavely sable to {UV Het and sq et and Uo bs he sare shown ( (@) What functional group x contained ia the Uyon suc? (0) Is Unlon chnerowth polymer a tp-gromth payer? (6) Draw te product tat woul before the polyer were completely hydrolyzed unde ardor basis conditions. Polyethylene gol, er Carhomae® [( O—CH,—CH,—)]. i widely use as abide, thickening agent and packaging ative for fonds (a) What type of poe is polyetylene glycol? (We have not sce this ype of plyine befor) (©) The systematic name for polyetylene geo is poly(ethylene oxide). What monomer woul! you us o make pulyetiyene gia? (6 What conions re-analysis aay et) would you consider using this polymerization? (a) Propoxe a plymeiation mechanism a faa the eae. Ring-openine mettbessplymerizaon (ROMP, sc Section 17) sa promising new ehnige For polymerizing cele olefins Ini simple frm, the ection valves a eyclalene (preferably with seme Hing rin oie the ‘Pacton) whose double nds undergo metatess (a trading of primers the end of he dole bons) o give polymer containing bah single and double bond 1 meme RA ‘ingopening metathesis polymerization (ROMP) ‘Show which monomers might have race to prdace the following polymer Palyoxyrethyene (polyormaldchy de) isthe tough, self ubricting Derin® plastic wad in gear hess (@) Give the sructre of poyformaliehyle () Formaldehyde is polymerized using un aii catalyet. Using H* as acta, propose a mechaism forthe polymerization as fara the einer (e) [Dakin an addition polyer or condensation polymer?2631 92633 6M "The 2000 Nobel Prize in Chemistry was awarded for work on polyacctylenes. Acetylene can be polymerized using ‘a Ziegler-Natta catalyst, The cs or tans stereochemistry ofthe products ean be controlled hy earefil selection and ‘reparation ofthe catalyst The resulting polyteetyene is an electrical semiconductor witha metalic appearance ‘isPolyacetylene as a copper cob, und rans-polyaceiyene is silver. (a) Draw the structure of it and irans-polyacetslene. {b) Use your structures to show why these polymers conduct electricity. {)_Iuspossile to prepare polyacetyene films whose electrical contvity is anisotrape. Thats the conductivity is hhgher in some directions than in others. Explain how this unusual behuvir is possible. Use chemical equations to show how the following accidents cause injury tothe clothing involved (nt to mention the skin under the clothing), (a) An industrial chemist spills aqueous H:S0, on her nylon stockings but fils o wash 4b) An organic laboratory student spills queo’s NaOH om his polyester slacks. Poly(vinyl alcohol), a hydrophilic polymer used in aqueous adhesives, is made by polymerizing vinyl acetate and then hydrolyzing the ester linkages. (a) Give the suctues of poly(vinyl acetate) and poly(vinyl aleebo). 4b) Vinyl acetate is an ester. Is poly(inyl acetate) therefore a polyester? Explain, (©) Wehave seen that basic hydrolysis destroys the Dacron polymer. Poly(vinyl acetate is converted to poly(vinyl alcohol by a basic hydrolysis of the ester atoups. Why doesnt the hydrolysis destroy the polyinyl alcohol) polymer? (a) Why is poly(viny! alcohol) made by this circuitous route? Why not just polymerize vinyl alcool? Inference to cloth or fiber, the term acetate usually means cellulose acetate, a semisyatbetc polymer made by treating cclulose with acetic anhydride. Cellulose oeetate is spun into yarm by dissolving tin acetone of methylene ehloride and oreng the solntion though spinnerets into warm ai, where the solvent evaporates. (2) Dea the suture of cellulowe sect (b) Explain why cellulose acetate is soluble in organic solvents, eventhough cellulose is mot. {@) (Atm sory) An organic chemistry student wore a long-sleeved acetate blouse tothe laboratory. She was rinsing a ‘warm separatory funnel with acetone when the pressure ose and blew out the stopper. Hee right arm was drenched ‘vith acetone, but she wat unconcerned because accone is ot Very toxic. About ten mites ler, the right aa the studem's blouse disintegrated int a pile of white lf leaving her with a ragged short sleeve and the tatters of a cut ‘remaining around her wrist. Explain how a substance as innocuous a acetone ruined the students blouse (@) Predict what usually happens when students wear polyvinyl chloride shoes othe organi laboratory ‘One of te earliest commercial plastics was Bakeli®, formed by the reaction of phenol witha ile more than one ‘equivalent of formaldehyde under acidic oc basi conditions. acyer first discovered this eaction in 1872, and practical tmethods for casting and molding Bakelite were developed around 1909. Phens-formaldehyde plastics and resins (aso led phenolics) ae highly cros-inked because each phenol rng hs hee sites (two ono and one para that can be linked by condensation with formaldehyde. Suggest a general srcture fra phenol-formaldehyde resin, and propese a ‘mechani for its formation under acidic conditions. (Hint: Condensation of phenol with formaldehyde resembles the condensation of phenol with acetoae, sed ia Problem 26-17, 10 make bisphenol A.) Plywood and particleboard ar often glued wit cheap, waterproof uea-fomaldehyde resins, Two to three males of formaldehyde ae mixed with one mole of urea and. ite ammonia ass basic catalyst. The reaction is allowed to proceed uni he mixture becomes syrupy. and then itis aplied wo the woud surface. The wood surfaces are held together under heat and presse, while polymerization continues and erss-inking takes ple. Propose a mechanism forthe ‘pas-catalyzed condensation of urea with formaldchyde to give a linea polymer, and then show how further condensation Jeals to cross-linking. (int: The carbonyl group lends aidty tothe NH protons of urea. A first condensation with fermaldshyde leas to an imine, which is weak electrophilic nd reacts with anolerdeprotonaled urea.) “The polyester named Lactomer® isan alternating copolymer of lactic acid and glycolic acid Lactomer is used for absorbable suture material because stitches of Latomer hydrolyze slowly over a two-week period and do n0t have the eemoved. The hydrolysis products, lactic acid and glycolic acd, ae normal metabolites and do not provoke an inflanmstory response. Draw the srctur of the Lactomer polymer mA wo ou soe ws off immesitly ‘Compare the molecular structures of coon and polypropylene, the two major components of thermal underwear. One of these gets wet easily and holds the water in contact withthe skin. The other ane does nt get wet, but wicks the water auay from the skin and foes relatvely dry to the ouch Explain the difference in how these to labrics respond to moist