Organic Chemistry

098 CHAPTER 28 Synthetic Polymers

Problems

22. Draw short segments of the polymers obtained from the following monomers:

a. d.

b. e.

c.

For each polymer, indicate whether the polymerization is a chain-growth or a step-growth polymerization.

23. Draw the repeating unit of the step-growth polymer that will be formed from each of the following reactions:

a.

b.

c.

d.

24. Draw the structure of the monomer or monomers used to synthesize the following polymers:

a. e.

b. f.

c. g.

d. h.

For each polymer, indicate whether it is a chain-growth polymer or a step-growth polymer.

25. Explain why the configuration of a polymer of isobutylene is not isotactic, syndiotactic, or atactic.

O O

CH 2 CH C COCH 2 CH 2 O

N

CH 2 C

CH 3

SO 2 SO 2 NH(CH 2 ) 6 NH

CH 2 CH 2 CH 2 CH 2 CO

O

CH 3

CH 2 CHO

CH 2 C CHCH 2

CH 3

CH 2 CH 3

CH 2 CH

OO+ (C 6 H 5 ) 3 P CH CH P(C 6 H 5 ) 3

O O

H 2 N OCH 2 CH 2 CH 2 ONH 2 + HC CH

CH 3

CH 3

C

CH 3

CH 3

Cl CCl+ HO CH 2 OH

BF 3

ClCH 2 CH 2 OCH 2 CH 2 Cl + HN NH

O

HO(CH 2 ) 5 COH

CH 3

OCN

CH 2 “CHCO 2 H NCO + HOCH 2 CH 2 OH

O O

CH 2 “CHF ClC(CH 2 ) 5 CCl + H 2 N(CH 2 ) 5 NH 2