Chapter 26: Q5P (page 1328)

Short Answer
(a) Vinyl chloride polymerizes well.
(b) Vinyl acetate does not polymerize well.
(c) does not possible polymerize well.
Chapter 26: Q5P (page 1328)

(a) Vinyl chloride polymerizes well.
(b) Vinyl acetate does not polymerize well.
(c) does not possible polymerize well.
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Plywood and particle board are often glued with cheap, waterproof urea-formaldehyde resins. Two to three moles of formaldehyde are mixed with one mole of urea and a little ammonia as a basic catalyst. The reaction is allowed to proceed until the mixture becomes syrupy, and then it is applied to the wood surface. The wood surfaces are held together under heat and pressure, while polymerization continues and cross-linking takes place. Propose a mechanism for the base-catalyzed condensation of urea with formaldehyde to give a linear polymer, and then show how further condensation leads to cross-linking. (Hint: The carbonyl group lends acidity to the N - Hprotons of urea. A first condensation with formaldehyde leads to an imine, which is weakly electrophilic and reacts with another deprotonated urea.)
. (a) Draw the structure of gutta-percha, a natural rubber with all its double bonds in the trans configuration.
(b) Suggest why gutta-percha is not very elastic, even after it is vulcanized.
Glyptal®resin makes a strong, solid polymer matrix for electronic parts. Glyptal is made from terephthalic acid and glycerol. Draw the structure of Glyptal and explain its remarkable strength and rigidity.
Polychloroprene, commonly known as neoprene, is widely used in wetsuits and in rubber parts that must withstand exposure to gasoline or other solvents.
(a) Is neoprene an addition polymer or a condensation polymer?
(b) What monomer is used to make this synthetic rubber?

(a) Isobutylene and isoprene coplymerize to give “butyl rubber”. Draw the structure of the repeating unit in butyl rubber, assuming that the two monomers alternate.
(b) Styrene and butadiene copolymerize to form styrene-butadiene rubber (SBR) for automobile tires. Draw the structure of the repeating unit in SBR, assuming that the two monomers alternate.
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