Chapter 17 Organic Polymer Chemistry

Multiple Choice

1. Which of the following are polymer architectures? (Sec. 17.2)

I) linear
II) tetrahedral
III) star
IV) ladder
V) forked

a) II, III, IV
b) III, IV, V
c) I, III, IV
d) I, II, IV

2. Which terms are correctly matched to their definitions? (Sec. 17.2)

I) Plastic – a long chain molecule synthesized by linking together many single parts.
II) Polymer – can be molded when hot and retains its shape when cooled.
III) Thermoplastic - can be molded when hot and retains its shape when cooled.
IV) Thermosetting plastic – can be molded when first prepared, but hardens irreversibly when
cooled.

a) III, IV
b) II, III
c) I, II
d) I, IV

3. Determine the repeat unit for the following polymer. (Sec. 17.1, 17.5, 17.6)

CH3 CH3 CH3

CH2CH O CH2CH O CH2CH O

CH3 CH3 CH3

a) CH2CH O b) CH2CH O CH2CH O
n n
CH3 CH3
c) CH O d) CH2CH
n n

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4. Determine the repeat unit for the following polymer. (Sec. 17.1, 17.5, 17.6)

CH2CH2 O O CH2CH2 O O CH2CH2 O O CH2CH2

a) O CH2CH2 O b) O CH2CH2 O
n n

c) O O CH2CH2 O O d) CH2CH2 O O CH2CH2

n n

5. Which characteristics are found in polymers with high degrees of crystallinity? (Sec. 17.4)

I) regular, compact structures

II) high Tm
III) weak intermolecular forces
IV) elasticity

a) I, III
b) I, II
c) III, IV
d) II, IV

6. Which characteristics are found in polymers with low degrees of crystallinity? (Sec. 17.4)

I) large molecular side groups

II) high Tm
III) strong intermolecular forces
IV) elasticity

a) I, III
b) II, III
c) III, IV
d) I, IV

7. Which terms are matched correctly with their definitions? (Sec. 17.4)

I) Crystalline domain – order regions in the solid state of a polymer.

II) Amorphous domain – disordered regions in the solid state of a polymer.
III) Melt transition temperature – temperature at which a polymer undergoes the transition from
hard to rubbery state.
IV) Glass transition temperature – temperature at which glass polymers melt.

a) II, III
b) III, IV
c) I, IV
d) I, II

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8. Which polymers are correctly classified? (Sec. 17.5)

O O
I CCH2CH2CH2CH2CNCH2CH2CH2CH2CH2CH2N
n
H H
polyamide
O
O CH3
C
II NCH2CH2CH2CH2CH2C III O O C
n n
H CH3
polycarbonate polyurethane
O O

IV C COCH2CH2O
n
polyester

a) II, III
b) III, IV
c) I, IV
d) I, II

9. Which polymers are correctly classified? (Sec. 17.5)

O O O
I NCH2CH2CH2CH2CH2C II CCH2CH2CH2CH2COCH2CH2O
n n
H polyether
polycarbonyl
O
O CH3 O
C
III CN NCOCH2CH2CH2O IV O O CH2
n
H H

polyurethane polycarbonate
a) I, III
b) II, III
c) III, IV
d) II, IV

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10. Which pair of compounds would react to form the polymer shown? (Sec. 17.5)

O O
CCH2CH2CH2CH2CNCH2CH2CH2CH2CH2CH2N
H H
O O
a) HOCCH2CH2CH2CH2COH + HOCH2CH2OH

O
b) H2NCH2CH2CH2CH2CH2CH2NH2 + C
Cl Cl
O O
c) HOCCH2CH2CH2CH2COH + H2NCH2CH2CH2CH2CH2CH2NH2

CH3 O
d) Na O C O Na + H2C C H + H2NCH2CH2NH2
CH3 CH2Cl

11. Which pair of compounds would react to form the polymer shown? (Sec. 17.5)
O
CH3
C
O O C
CH3

O O
a) HO C C OH + HOCH2CH2OH

CH3 O
b) Na O C O Na + C
Cl Cl
CH3
O O
c) HOCCH2CH2CH2CH2COH + H2NCH2CH2CH2CH2CH2CH2NH2

CH3 O
d) Na O C O Na + H2C C H + H2NCH2CH2NH2
CH3 CH2Cl

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12. Which pair of compounds would react to form the polymer shown? (Sec. 17.5)

OH CH3 OH H
O C O N
N
CH3 n
H

O O
a) HO C C OH + HOCH2CH2OH

CH3 O
b) Na O C O Na + C
Cl Cl
CH3
O O
c) HOCCH2CH2CH2CH2COH + H2NCH2CH2CH2CH2CH2CH2NH2

CH3 O
d) Na O C O Na + H2C C H + H2NCH2CH2NH2
CH3 CH2Cl
13. Which compound would react to form the polymer shown? (Sec. 17.6)

a) O
b) c) Cl OH d)

14. Which is not a step in the mechanism of a chain growth polymerization? (Sec. 17.6)

a) initiation
b) propagation
c) proliferation
d) termination

15. Which classification best describes the mechanism of step growth polymerization? (Sec. 17.5)

a) nucleophilic acyl addition

b) nucleophilic acyl substitution
c) electrophilic addition
d) radical substitution

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16. Which statements are true describing the Ziegler-Natta process? (Sec. 17.6)

I) the process yields low density polyethylene

II) the process involves radicals
III) the process uses an alkytitanium catalyst
IV) the process yields polyethylene 3 to 10 times stronger than other methods

a) I, II
b) II, IV
c) II, III
d) III, IV

17. Which polymers will be brittle at 0° C? (Sec. 17.4)

I) PVC, Tg = 83° C
II) PVA, Tg = 200° C
III) teflon, Tg = -80° C
IV) polypropylene, Tg = -100° C

a) III, IV
b) II, III
c) I, II
d) II, IV

18. Which polymers will be elastic at 0° C? (Sec. 17.4)

I) PVC, Tg = 83° C
II) PVA, Tg = 200° C
III) teflon, Tg = -80° C
IV) polypropylene, Tg = -100° C

a) III, IV
b) II, III
c) I, II
d) II, IV

19. Which polymers will be strongest? (Sec. 17.4)

a) PET 0% crystallinity
b) PET 20% crystallinity
c) PET 35% crystallinity
d) PET 55% crystallinity

20. Which polymers will be the most elastic? (Sec. 17.4)

a) PET 0% crystallinity
b) PET 20% crystallinity
c) PET 35% crystallinity
d) PET 55% crystallinity

21. Which polymers are step-growth polymers? (Sec. 17.5)

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I) nylon
II) HDPE
III) Teflon
IV) PET

a) I, II
b) II, III
c) I, IV
d) III, IV

22. Which polymers are chain-growth polymers? (Sec. 17.6)

I) nylon
II) HDPE
III) Teflon
IV) PET

a) I, II
b) II, III
c) I, IV
d) III, IV

23. Which polymers are step-growth polymers? (Sec. 17.5)

I) Kevlar
II) Mylar
III) PVC
IV) Lucite

a) I, II
b) II, III
c) I, IV
d) III, IV

24. Which polymers are chain-growth polymers? (Sec. 17.6)

I) Kevlar
II) Mylar
III) PVC
IV) Lucite

a) I, II
b) II, III
c) I, IV
d) III, IV

25. Which polymers are correctly matched to their primary use? (Sec. 17.5, 17.6)

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I) Kevlar and containers

II) Polymethylmethacrylate and Plexiglas
III) Polytetrafluoroethylene and nonstick coatings
IV) PET and bulletproof vests

a) I, III
b) II, III
c) II, IV
d) III, IV

Fill in the Blank

1. The repeat unit of polyacrylonitrile is,

H H H H
CH2 C CH2 C CH2 C CH2 C n
CN CN CN CN (Sec. 17.6)

2. The repeat unit of polymethylacrylate is,

H H H H
CH2 C CH2 C CH2 C CH2 C n

O O O O
OCH3 OCH3 OCH3 OCH3
(Sec. 17.6)

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3. The polymer (Nylon 612) synthesized from the following monomers is,

H2N CH2 CH2 CH2

CH2 CH2 CH2 NH2
and
O
C CH2 CH2 CH2 CH2 CH2
HO OH
CH2 CH2 CH2 CH2 CH2 C
O (Sec. 17.5)

4. The polymer (PEN) synthesized from the following monomer is

O
CH3O C O
C OCH3
HO CH2 CH2 OH
and (Sec. 17.5)

5. The monomers used to synthesize Nomex are,

O O
N N n
H H
(Sec. 17.5)

and

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6. The monomers used to synthesize the following polyurethane are,

O O
N CH2 N O CH2 CH2 O n
H H
(Sec. 17.5)

and

7. Complete the mechanism for radical chain propagation begun below. (Sec. 17.6)

. .
Cl
In Cl Cl In Cl

8. The label of the following step of radical chain polymerization is __________________________.

. .
Cl Cl
Cl Cl
Cl Cl
R Cl Cl R (Sec. 17.6)

9. A carbonate, which forms the backbone of polycarbonates, has the following structure,

(Sec. 17.5)

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10. A diepoxide, which forms the backbone of epoxy resins, has the following structure,

(Sec. 17.5)
True-False

1. The glass transition temperature (Tg) must be low for an elastomer to maintain its properties. (Sec. 17.4)

2. The opaquety of a crystalline polymer correlates to the Tm. (Sec. 17.4)

3. The polymer synthesized from the following monomer is,

Cl Cl Cl Cl Cl
Cl
n

Cl Cl Cl Cl Cl Cl (Sec. 17.6)

4. A polymer synthesized from the following monomers could have the form,

H2C CH2 and H2C CH

CH2 CH2
HC CH3
H3 C
(Sec. 17.6)

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5. A polymer synthesized from the following monomers could have the form,

H CH3
H 2C C and H 2C
CN O
O CH3
(Sec. 17.6)

H H H H
CH2 C CH2 C CH2 C CH2 C n
CN O CN O
OCH3 OCH3

6. Radical chain growth polymers tend to form head to head bonds between carbon one of one monomer and
carbon one of another monomer. (Sec. 17.6)

7. Branching of polyethylene, due to a chain transfer reaction, produces low density polyethylene (LDPE).
(Sec. 17.6)

8. The Zeigler-Natta process yields low density polyethylene (LDPE). (Sec. 17.6)

9. A polymer with a melt transition temperature (Tm) of 200° C is stronger than a polymer with a Tm of 150° C.
(Sec. 17.4)

10. An elastomer with a glass transition temperature (Tg) of 25° C will lose its elasticity below 25° C. (Sec. 17.4)

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Answers

Multiple Choice

1. c
2. a
3. a
4. b
5. b
6. d
7. d
8. c
9. c
10. c
11. b
12. d
13. a
14. c
15. b
16. d
17. c
18. a
19. d
20. a
21. c
22. b
23. a
24. d
25. b

Fill in the Blank

1.

CN
2.

O
CH3O
3.
O
H
N *
* N n
H
O
4.
O
* O
O *
O n

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5.
O O
H2N NH2
HO OH
and

6.

O C N CH2 N C O HO OH
and
7.

. Cl
In Cl Cl In Cl

8. Termination
9.
O

RO OR

10.
O O
R

True-False

1. T
2. T
3. F
4. T
5. F
6. F
7. T
8. F
9. T
10. T

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