Organic Chemistry

(Dana P.) #1
Problems 099


  1. Draw short segments of the polymers obtained from the following compounds under the given reaction conditions:


a. d.

b. e.

c. f.


  1. Quiana®is a synthetic fabric that feels very much like silk.
    a. Is Quiana®a nylon or a polyester?
    b. What monomers are used to synthesize Quiana®?

  2. Explain why a random copolymer is obtained when 3,3-dimethyl-1-butene undergoes cationic polymerization.

  3. Polly Propylene has started two polymerization reactions. One flask contains a monomer that polymerizes by a chain-growth
    mechanism, and the other flask contains a monomer that polymerizes by a step-growth mechanism. When the reactions are
    terminated and the contents of the flasks analyzed, one flask contains a high-molecular-weight polymer and some monomer, but
    very little material of intermediate molecular weight. The other flask contains mainly material of intermediate molecular weight
    and very little monomer or high-molecular-weight material. Which flask contains which product? Explain.

  4. 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.
    a. Why is poly(vinyl alcohol) not prepared by polymerizing vinyl alcohol?
    b. Is poly(vinyl acetate) a polyester?

  5. Five different repeating units are found in the polymer obtained by cationic polymerization of 4-methyl-1-pentene. Identify these
    repeating units.

  6. If a peroxide is added to styrene, the polymer known as polystyrene is formed. If a small amount of 1,4-divinylbenzene is added to
    the reaction mixture, a stronger and more rigid polymer is formed. Draw a short section of this more rigid polymer.

  7. A particularly strong and rigid polyester used for electronic parts is marketed under the trade name Glyptal®. It is a polymer of
    terephthalic acid and glycerol. Draw a segment of the polymer, and explain why it is so strong.


1,4-divinylbenzene

CH 2 CH CH CH 2

CH 2 CH CH 2 CH CH 2 CH

OCCH 3

O

OCCH 3

O

OCCH 3

CH 2 CH CH 2 CH CH 2 CH

OH OH OH

O

H 2 O

poly(vinyl alcohol)

poly(vinyl acetate)


CH 2 CH C CH 3 CH 2 CH CH 2 CH

CH 3

CH 3

C

CH 3

CH 3 CH 3

CH 2 CH C

CH 3

CH 3 CH 3

CH 2 CH

CH 3 CCH 3

CH 3

CH 3 CCH 3

CH 3

O

Quiana

NH CH 2 C (CH 2 ) 6

O

NH CNH CH 2 NH

CH 2 CHCH 2 CH 2 CH 3

BF 3
CH 2 C NCH 3

CH 3
peroxide

a Ziegler–Natta catalyst
CH 2 C C CH 2

CH 3 CH 3

CH 2 CHCl

CH 3 CH 2 CH 2 CH 2 Li

O

NH H+, H 2 O

H 2 C

O
CHCH 3

CH 3 O−

AU: OK as changed?


AU: OK as changed?

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