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Chapter 26: Q2P (page 1326)

Propose a mechanism for reaction of the first three propylene units in the polymerization of propylene in the presence of benzoyl peroxide.

Short Answer

Expert verified

This type of polymerization results when a suitable alkene is heated with a radical initiator.

Step by step solution

01

Free-radical polymerization

This type of polymerization results when a suitable alkene is heated with a radical initiator.

02

Mechanism

In the initiation step, the initiator forms a radical that reacts with the monomer to start the chain.

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Most popular questions from this chapter

(a) Nomex®, a strong fire-resistant fabric, is a polyamide made from meta-phthalic acid and meta-diaminobenzene. Draw the structure of Nomex.

(b) Kevlar®, made from terephthalic acid (para-phthalic acid) and para-diaminobenzene, is used in making tire cord and bulletproof vests. Draw the structure of Kevlar.

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) 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.

Give the structure of the polyurethane formed by the reaction of toluene diisocyanate

with bisphenol A.

In reference to cloth or fiber, the term acetate usually means cellulose acetate, a semisynthetic polymer made by treating cellulose with acetic anhydride. Cellulose acetate is spun into yarn by dissolving it in acetone or methylene chloride and forcing the solution through spinnerets into warm air, where the solvent evaporates.

(a) Draw the structure of cellulose acetate.

(b) Explain why cellulose acetate is soluble in organic solvents, even though cellulose is not.

(c) (A true story) An organic chemistry student wore a long-sleeved blouse to the laboratory. She was rinsing a warm separatory funnel with acetone when the pressure rose and blew out the stopper. Her right arm was drenched with acetone, but she was unconcerned because acetone is not very toxic. About ten minutes later, the right arm of the student’s blouse disintegrated into a pile of white fluff, leaving her with a ragged short sleeve and the tatters of a cuff remaining around her wrist. Explain how a substance as innocuous as acetone ruined the student’s blouse.

(d) Predict what usually happens when students wear polyvinyl chloride shoes to the organic laboratory.
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