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- Draw a stepwise mechanism for the following polymerization reaction.Propylene forms only oligomer under normal free radical conditions, yet the monomer forms high-molecular-weight polymer if it is polymerized while trapped in the channels of a crystalline host substance such as urea or thiourea. Explain [G. Di Silvestro, P. Sozzani, and M. Farina, Polym. Preprints, 27(1), 92, 1986].Although chain branching in radical polymerizations can occur by intermolecular H abstraction as shown in Mechanism 30.2, chain branching can also occur by intramolecular H abstraction to form branched polyethylene that contains butyl groups as branches.a. Draw a stepwise mechanism that illustrates which H must be intramolecularly abstracted to form butyl substituents.b. Suggest a reason why the abstraction of this H is more facile than the abstraction of other H’s.
- Consider monomers A–C. (a) Rank the monomers in order of increasingreactivity in cationic polymerization. (b) Rank the monomers in order ofincreasing reactivity in anionic polymerization.Cationic polymerization of 3-phenylpropene (CH2=CHCH2Ph) affords Aas the major product rather than B. Draw a stepwise mechanism toaccount for this observation.Although chain branching in radical polymerizations can occur by intermolecular H abstraction as shown in Mechanism 28.2, chain branching can also occur by intramolecular H abstraction to form branched polyethylene that contains butyl groups as branches.a. Draw a stepwise mechanism that illustrates which H must be intramolecularly abstracted to form butyl substituents. b. Suggest a reason why the abstraction of this H is more facile than the abstraction of other H's.
- Rank the following monomers in order of increasing reactivity toward anionic polymerization (least reactive to most reactive).Poly(vinyl alcohol) is a polymer used to make fibers and adhesives. It is synthesized by hydrolysis or alcoholysis of the polymer obtained from polymerization of vinyl acetate as shown below. a. Why is poly(vinyl alcohol) not prepared by polymerizing vinyl alcohol? b. Is poly(vinyl acetate) a polyester?Rank the following monomers in order of increasing reactivity toward cationic polymerization (least reactive to most reactive).
- Draw the starting structure that would lead to this polymer under radical cond(a) Explain why poly(vinyl alcohol) cannot be prepared by the radical polymerization of vinyl alcohol (CH2=CHOH). (b) Devise a stepwise synthesis of poly(vinyl alcohol) from vinyl acetate (CH2=CHOCOCH3). (c) How can poly(vinyl alcohol) be converted to poly(vinyl butyral), a polymer used in windshield safety glass?(a) Show how poly(propylene oxide) can be synthesized via anionic ring-opening polymerization. (b) Draw the mechanism for the initiation and first two propagation steps.