Organic Chemistry, 8e (Bruice)

Chapter 27 Synthetic Polymers

1) List the two major classes of synthetic polymers and give one example of each.
Answer:
a) Addition polymers, also known as chain-growth polymers; polystyrene for example.
b) Condensation polymers, also known as step-growth polymers; nylon for example.
Section: 27-1

2) Draw the structure of the polymer and by-product that result when the two monomers below
are heated together.

Answer:

Section: 27-1
MCAT: 20.7

3) What is the structure of the monomer from which the following polymer is made?

A) CH3CH3
B) CH2 CH2
C) CH3CH CH2
D) CH2 CHCH CH2
E) CH3CH CHCH3
Answer: E
Section: 27-3
GLO: G2

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4) What is the structure of the monomer from which the following polymer is made?

A) I
B) II
C) III
D) IV
E) V
Answer: B
Section: 27-3
GLO: G2

5) Which of the following addition polymers results from the reaction below?
nCF2 CF2 ?
A) [ CF-CF ]n
B) [CF3-CF3]n
C) [-CF2-CH CHCF2-]n
D) [-CF2-CF2-]n
E) [-CF2 CF2-]n
Answer: D
Section: 27-3

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6) Which of the following statements best describes what alpha olefins are?
A) polysubstituted ethylenes
B) monosubstituted ethylenes
C) disubstituted ethylenes
D) ethylenes
E) isoprenes
Answer: B
Section: 27-3

7) The choice of mechanism in chain-growth polymerization depends on which of the following?

A) structure of the monomer and initiator used
B) structure of the polymer and initiator used
C) temperature and pressure of the reaction
D) A and B
E) A, B, and C
Answer: A
Section: 27-2

8) Chain-growth polymerization proceeds by which of the following mechanisms?

A) radical polymerization
B) cationic polymerization
C) anionic polymerization
D) A and B
E) A, B, and C
Answer: E
Section: 27-2

9) Which of the following species can best serve as a radical initiator for radical polymerization?
A) ROH
B) ROR
C) ROOR
D) RCOOR
E) RCOOH
Answer: C
Section: 27-3

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10) Which of the following is the first chain propagating step in the radical polymerization of
ethylene?
A) ROOR + CH2 CH2 → ROCH2CH2OR
B) ∙
RO∙ + CH2 CH2 → ROCH2CH2
C) RO∙ + CH2 CH2 → ROCH CH2 + H∙
D) ∙ ∙
ROOR + CH2 CH2 → 2 ROH + CH CH
E) ∙ ∙
2RO∙ + CH2 CH2 → 2 ROH + CH CH
Answer: B
Section: 27-3

11) Which of the following is a possible step to terminate a chain in the radical polymerization of
ethylene?
A) ROOR + CH2 CH2 → ROCH2CH2OR
B) CH2 CH2 + CH2 CH2 → CH3CH CHCH3
C) ∙
RO∙ + CH2 CH2 → ROCH2 CH2
D) ∙ ∙
ROCH2CH2 + CH2 CH2 → ROCH2CH2CH2CH2
E) ∙
2 RO—[CH2CH2]n—CH2CH2 →
RO—[CH2CH2]n—CH2CH2CH2CH2—[CH2CH2]n—OR
Answer: E
Section: 27-3

12) Which of the following statements best explains the process known as chain transfer?
A) a process that can control the rate of production of the polymer
B) a process that can control the molecular weight of the polymer
C) a process that can control the reactivity of the monomer
D) a process that can slow down the polymerization reaction
E) a process that can inhibit the polymerization reaction
Answer: B
Section: 27-3

13) Chain-growth polymerization exhibits a marked preference for

A) tail-to-tail addition
B) head-to-head addition
C) head-to-tail addition
D) head-to-middle addition
E) middle-to-tail addition
Answer: C
Section: 27-3
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14) Which of the following are characteristic of linear polyethylene?
A) They are branched polymers.
B) They are known as high-density polyethylene.
C) They are soft and flexible polymers.
D) A and B
E) A and C
Answer: B
Section: 27-3

15) Which of the following species can best serve as an initiator for cationic polymerization?
A) ROOR
B) ROH
C) ROR
D) AlCl3
E) RCOOR
Answer: D
Section: 27-4

16) Which of the following is the chain-initiating step in the cationic polymerization of propene?

A) I
B) II
C) III
D) IV
E) V
Answer: E
Section: 27-4
MCAT: 1.4
GLO: G2

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17) Which of the following is more likely to undergo both radical and cationic polymerization?

A) I
B) II
C) III
D) IV
E) V
Answer: B
Section: 27-4

18) Which of the following monomers has the greatest ability to undergo cationic
polymerization?

A) I
B) II
C) III
D) IV
E) V
Answer: C
Section: 27-4
GLO: G2

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19) Which of the following monomers has the greatest ability to undergo anionic
polymerization?

A) I
B) II
C) III
D) IV
E) V
Answer: E
Section: 27-5
GLO: G2

20) Which of the following species can best serve as an initiator for anionic polymerization?
A) CH3CH2CH2CH2Li
B) BF3
C) HOOH
D) CH3CH2CH2CH2OH
E) CH3CH2CH2CH2OCH2CH2CH2CH3
Answer: A
Section: 27-5

21) Which of the following is more likely to form non-terminated polymeric chains called living
polymers?
A) cationic polymerization
B) free radical polymerization
C) anionic polymerization
D) A and B
E) A and C
Answer: C
Section: 27-5

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22) From which of the following compounds is Lucite or poly(methyl methacrylate) prepared?
A) CH2 CHCH3
B) CH2 C(CH3)O2CCH3
C) CH2 CHO2CCH3
D) CH2 C(CH3)CO2CH3
E) CH2 CHCO2CH3
Answer: D
Section: 27-2

23) Which of the following can result in chain termination in cationic polymerization?
A) loss of H+
B) addition of a nucleophile that reacts with the propagating site
C) a chain transfer reaction with the solvent
D) a 1,2-hydride shift.
E) A, B, and C
Answer: E
Section: 27-4

24) Which of the following monomers is least likely to undergo cationic polymerization?
A) propylene
B) isobutylene
C) styrene
D) methyl acrylate
E) vinyl acetate
Answer: D
Section: 27-4

25) Which is not typically made through radical polymerization?

A) poly(styrene)
B) PVC
C) Dacron
D) poly(vinyl acetate)
E) Lucite
Answer: C
Section: 27-3
GLO: G5

26) Provide the structure of the monomer from which Orlon [poly(acrylonitrile)] is prepared.
Answer: CH2 CHC N
Section: 27-2
GLO: G5

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27) What structural characteristic is shared by compounds used as radical initiators?
Answer: Such compounds possess a relatively weak bond that readily undergoes homolytic
cleavage.
Section: 27-3
GLO: G8

28) In a recycling symbol, the ________ the number in the middle of the symbol, the more easily
the compound can be recycled.
Answer: lower
Section: 27-13

29) List the three phases in the mechanism of chain-growth polymerization.

Answer:
1. Initiation
2. Propagation
3. Termination
Section: 27-3

30) Show the three methods by which the following radical can be terminated.

Answer:
a)

b)

c)

Section: 27-3

31) Explain why some monomers are better able to undergo chain-growth polymerization by a
radical mechanism.
Answer: A monomer with a substituent (X) that is able to stabilize the growing radical species
by resonance will undergo chain-growth polymerization by a free radical mechanism.
Section: 27-3
GLO: G8

32) What are common factors that enter into the choice of radical initiators for chain-growth
polymerization?
Answer:
1. A relatively weak bond like the oxygen-oxygen single bond
2. Desired solubility of the initiator
3. Temperature of the polymerization reaction
Section: 27-3

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33) Show the mechanism for the formation of a segment of polystyrene containing two
molecules of styrene and initiated by hydrogen peroxide.
Answer:

Section: 27-3
GLO: G2

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34) When 3-methyl-1-butene

CH2 CHCH(CH3)2

undergoes cationic polymerization, the following expected carbocation is formed.

⊕
X—CH2—CH—CH(CH3)2

However, the following carbocation is also found in the reaction.

⊕
X—CH2—CH2—C(CH3)2

Explain.
Answer: The expected carbocation is a 2° carbocation which may rearrange to a 3° carbocation,
a more stable carbocation. This is a classic 1,2-hydride shift.
Section: 27-4
MCAT: 15.2
GLO: G2, G8

35) When 2,2-dimethyloxirane (see figure below) undergoes anionic polymerization, the
nucleophile attacks the least substituted carbon of the epoxide, but when it undergoes cationic
polymerization, the nucleophile attacks the most substituted carbon of the epoxide. Explain why
this is so.

Answer: In anionic polymerization, the nucleophile will seek the least hindered carbon similar
to an SN2 reaction. However, in cationic polymerization, the reaction involves a partial
carbocation and the attack is on the most hindered (most stable) carbocation.
Section: 27-5
MCAT: 15.2
GLO: G2

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36) Show the reaction which occurs when benzoyl peroxide is heated.
Answer:

Section: 27-3

37) Show how branching could occur during the free-radical polymerization of styrene.
Answer:

Section: 27-3

38) Provide a mechanism to show how H2C C(CH3)2 is polymerized using BF3 as the initiator.
Answer:

Section: 27-4
MCAT: 1.4

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39) Propose a synthesis of poly(vinyl alcohol) from H2C CHO2CCH3.
Answer:
1. (PhCO2)2
2. NaOH, H2O
Section: 27-3

40) Provide a mechanism to show how H2C CHCO2CH3 is polymerized using butyllithium as
the initiator.
Answer:

Section: 27-5
GLO: G2

41) Why is chain branching less common in anionic polymerization than in cationic
polymerization?
Answer: The intermediate which leads to chain branching is a more substituted carbon ion.
Greater substitution stabilizes carbocations but destabilizes carbanions.
Section: 27-5
GLO: G2, G8

42) What is the main structural difference between high-density and low-density polyethylene,
and how does this structural difference affect the properties and uses of these polymers?
Answer: High-density polyethylene is linear while low-density polyethylene is branched.
Linear, unbranched chains can pack together more closely than branched ones. Thus, high-
density polyethylene is a relatively hard plastic and is used for the production of things like
artificial hip joints. Low-density polyethylene is a much more flexible polymer which is used to
make trash bags and dry cleaning bags.
Section: 27-12
GLO: G5, G8

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43) What advantage does a Lewis acid like BF3 have over a proton-donating acid like HCl as a
initiator in cationic polymerization?
Answer: The advantage of a Lewis acid initiator like BF3 is that it does not have an
accompanying nucleophile that could act as a chain terminator.
Section: 27-4
MCAT: 1.4
GLO: G2, G8

44) Is acrylonitrile more likely to undergo anionic or cationic polymerization? Explain your
answer.
Answer: Acrylonitrile is more likely to undergo anionic polymerization. The cyano group is an
electron-withdrawing group that can stabilize an anion.
Section: 27-4
GLO: G2, G8

45) Draw the structure of the polymer that results when methyl α-cyanoacrylate undergoes
polymerization. By what name is this polymer commonly known?
Answer: This polymer is commonly known as Super Glue.

Section: 27-5
GLO: G5

46) Give the monomer for the polymer teflon.

A) propylene
B) acrylonitrile
C) tetrafluoroethylene
D) poly(vinyl acetate)
E) styrene
Answer: C
Section: 27-3

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47) Draw the monomer for poly(vinyl acetate).
A)

B)

C)

D)

E)

Answer: D
Section: 27-3
GLO: G5

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48) Draw a short segment of plexiglass, using five monomers.
Answer:

Section: 27-3
GLO: G5

49) Identify the monomer(s) that undergo radical polymerization. You may choose more than
one answer.
A) styrene
B) methyl methacrylate
C) vinyl chloride
D) methyl vinyl ether
E) acrylamide
Answer: A, B, C
Section: 27-3

50) Identify the monomer(s) that undergo cationic polymerization. You may choose more than
one answer.
A) styrene
B) methyl methacrylate
C) vinyl chloride
D) methyl vinyl ether
E) acrylamide
Answer: A, D
Section: 27-4

51) Identify the monomer(s) that undergo anionic polymerization. You may choose more than
one answer.
A) styrene
B) methyl methacrylate
C) vinyl chloride
D) methyl vinyl ether
E) acrylamide
Answer: A, B, E
Section: 27-5

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52) Identify the initiator in a radical polymerization.
A) KOH
B) BuLi
C) CH3OOCH3
D) BF3, H2O
E) HCl
Answer: C
Section: 27-3

53) Identify the initiator in a cationic polymerization.

A) KOH
B) BuLi
C) CH3OOCH3
D) BF3, H2O
E) HCl
Answer: D
Section: 27-4

54) Identify the initiator in an anionic polymerization.

A) KOH
B) BuLi
C) CH3OOCH3
D) BF3, H2O
E) HCl
Answer: B
Section: 27-5

55) Identify the monomer for superglue.

A) acrylamide
B) methyl a-cyanoacrylate
C) acrolein
D) methyl vinyl ether
E) styrene
Answer: B
Section: 27-5
GLO: G5

56) Draw a short segment of neoprene, using four monomers.

Answer:

Section: 27-8

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57) What is the mass of each repeating unit in poly(ethylene)?
Answer: 28 g/mol
Section: 27-3

58) Provide the structure of poly(vinyl chloride).

Answer:

Section: 27-3

59) Provide the structure of poly(propylene).

Answer:

Section: 27-3

60) Provide the structure of poly(acrylonitrile).

Answer:

Section: 27-3

61) Provide the structure of poly(tetrafluoroethylene).

Answer:

Section: 27-3

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62) A substituted ethylene polymer in which the substituents are randomly oriented is called
A) a ditactic polymer.
B) an eutatic polymer.
C) an isotactic polymer.
D) a syndiotatic polymer.
E) an atactic polymer.
Answer: E
Section: 27-7

63) Which of the following polymers is arranged in an isotactic configuration?

A) I
B) II
C) III
D) IV
E) V
Answer: D
Section: 27-7

64) Which of the following initiators are known as Ziegler-Natta catalysts, which were
discovered in 1953 in order to control the stereochemistry of polymers?
A) Al/Ti initiators
B) Ni/Cd initiators
C) Zn/Hg initiators
D) Pb/C initiators
E) Pb/PbO2 initiators
Answer: A
Section: 27-7

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65) Which of the following statements concerning the stereochemistry of polymerization is
correct?
A) Polymers in the atactic configuration are more likely to be crystalline solids because regular
packing of the polymer chains is easier.
B) Polymers in the isotactic configuration tend to be softer and more flexible than atactic
polymers.
C) In general, radical polymerization leads primarily to branched polymers in the syndiotactic
configuration.
D) The percentage of chains in the isotactic or syndiotactic configuration decreases as the
polymerization temperature decreases.
E) none of the above
Answer: E
Section: 27-7

66) What is the difference between natural rubber and Gutta-percha rubber?
A) Natural rubber is hard and brittle while gutta-percha is soft and rubbery.
B) Natural rubber is natural while gutta-percha is synthetic rubber.
C) Natural rubber has a cis configuration while gutta-percha has a trans configuration.
D) Natural rubber and gutta-percha rubber are enantiomers.
E) The monomer for natural rubber is isoprene while the monomer for gutta-percha is 1,3-
butadiene.
Answer: C
Section: 27-7

67) Which of the following statements best describes what vulcanization means?
A) a process by which rigid and non-sticky rubber can be made soft and sticky
B) a chemical process discovered by Charles Schultz in 1944
C) the heating of rubber with sulfur
D) a chemical process that destroys cross-linking in rubber
E) all of the above
Answer: C
Section: 27-7

68) Natural rubber is a

A) polyamide.
B) polyester.
C) polycarbonate.
D) polyurethane.
E) none of the above.
Answer: E
Section: 27-7

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69) From which of the following monomers is neoprene synthesized?
A) (Z)-2-chloro-2-butene
B) (E)-2-chloro-2-butene
C) (E)-1-chloro-1,3-butadiene
D) 2-chloro-1,3-butadiene
E) 2,3-dichloro-1,3-butadiene
Answer: D
Section: 27-7

70) Draw the structure of the polymer produced in the following reaction.

Answer:

Section: 27-7

71) Name the monomer used in the production of neoprene.

Answer: 2-chloro-1,3-butadiene or chloroprene
Section: 27-7

72) The pattern below is found in what type of polymer?

AAAABBBBAAAABBBB
A) an alternating copolymer
B) a block copolymer
C) a random copolymer
D) a graft copolymer
E) a homopolymer
Answer: B
Section: 27-9

73) The pattern below is found in what type of polymer?

AABBBABAABABBAAB
A) an alternating copolymer
B) a block copolymer
C) a random copolymer
D) a graft copolymer
E) a homopolymer
Answer: C
Section: 27-9

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74) Provide the structure of Saran, an alternating copolymer of H2C CHCl and H2C CCl2.
Answer:

Section: 27-9

75) ABS is a copolymer of what three monomers?

Answer: acrylonitrile, 1,3-butadiene, and styrene
Section: 27-9

76) Identify the type of polymer for poly(vinyl chloride).

A) homopolymer
B) graft copolymer
C) random copolymer
D) block copolymer
E) alternating copolymer
Answer: A
Section: 27-9

77) Identify the type of polymer for nylon 66.

A) homopolymer
B) graft copolymer
C) random copolymer
D) block copolymer
E) alternating copolymer
Answer: E
Section: 27-11

78) Kevlar is an example of

A) a polyester.
B) an aramide.
C) a polyurethane.
D) a epoxy resin.
E) a plasticizer.
Answer: B
Section: 27-11

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79) Which of the following is a step-growth polymer?
A) polyethylene
B) polyester
C) polypropylene
D) polystyrene
E) Plexiglass
Answer: B
Section: 27-11

80) What are aramides?

A) aromatic polyester polymers
B) aromatic amine polymers
C) alkyl halide polymers
D) aromatic polyamide polymers
E) aliphatic polyamide polymers
Answer: D
Section: 27-11

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81) What monomers formed the following polymer?

A) I
B) II
C) III
D) IV
E) V
Answer: A
Section: 27-11

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82) Which dimer (step-growth dimerization) will form from the following monomer?

A)

B)

C)

D)

E)

Answer: C
Section: 27-11

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83) What kind of polymer is produced in the following reaction?

A) a polycarbonate
B) a polyurethane
C) a polyester
D) a synthetic rubber
E) a poly (acrylonitrile)
Answer: B
Section: 27-11
GLO: G5

84) Propose a mechanism for the following polymerization reaction:

Answer:

Section: 27-6
GLO: G2

85) Draw the structure of the polymer produced in the following reaction.

Answer:

Section: 27-11
MCAT: 21.5

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86) Draw the products which would result if poly(ethylene terephthalate) were hydrolyzed in hot
aqueous NaOH.
Answer:

Section: 27-11
MCAT: 21.4

87) Draw the structure of Nylon 66.

Answer:

Section: 27-11
GLO: G5

88) Identify the product of the following reaction.

A) nylon 44
B) nylon 6
C) nylon 4
D) nylon 66
E) nylon 55
Answer: D
Section: 27-11
GLO: G5

89) Give the product of the following polymerization.

Answer:

Section: 27-11

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90) Draw a segment of the polymer, using four monomers.

Answer:

Section: 27-11

91) Give the monomers for lexan.

Answer:

Section: 27-11

92) Give the purpose of the amine in the formation of the epoxy resin.
A) a softener
B) hardener
C) a monomer in the reaction
D) to dehydrate the monomer
E) to chill the polymer
Answer: B
Section: 27-11

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93) Give the product for an diisocyanate reacting with a diol.
A) an epoxy resin
B) a polyester
C) a polycarbonate
D) a polyamide
E) a polyurethane
Answer: E
Section: 27-11

94) Give the product for the following reaction.

Answer:

Section: 27-11

95) Which of the following are characteristics of thermosetting polymers?

A) strong and rigid
B) high degree of cross-linking
C) can be remelted by heating
D) A and B
E) A, B, and C
Answer: D
Section: 27-12

96) What are elastomers?

A) elastic organic molecules that are added to polymers to make them harder
B) plastics that stretch and then revert to their original shape
C) polymers that are soft and sticky
D) plastics that are hard and brittle
E) elastic molecules that are added to polymers to make them stretch more
Answer: B
Section: 27-12

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97) Which of the following is characteristic of oriented polymers?
A) weaker than steel
B) chains are arranged in parallel fashion
C) chains are arranged in perpendicular fashion
D) polymer chains are made from sulfur atoms
E) all of the above
Answer: B
Section: 27-12

98) What are crystallites?

Answer: The regions of polymers in which the chains are highly ordered with respect to one
another.
Section: 27-12

99) Describe what thermoplastic polymers are.

Answer: Polymers that have both ordered crystalline regions and amorphous, non-crystalline
regions. The polymers are hard at room temperature but can be remelted and remolded by
heating. Thermoplastic polymers are the plastics that we most often encounter in our daily lives.
Section: 27-12

100) Describe what plasticizers are and give an example.

Answer: An organic compound that dissolves in the polymer and allows the polymer chains to
slide by each other.
Ex. Dibutyl phthalate,

Section: 27-13

101) What are biodegradable polymers? Give an example.

Answer: Polymers that can be broken into smaller segments by enzyme-catalyzed reaction using
enzymes produced by microorganisms.
Ex. Inserting hydrolyzable esters into polymers can cause weak links in the polymer which are
hydrolyzable by enzyme-catalyzed reactions.
Section: 27-14

102) What are thermosetting polymers?

Answer: Thermosetting polymers cannot be remelted after they have hardened because the
cross-links present are covalent bonds and not intermolecular van der Waals forces.
Section: 27-12

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103) As the % crystallinity of polyethylene increases, its density ________ and its melting point
________.
Answer: increases; increases
Section: 27-12

104) The joining together of many monomers to form a very large molecule is called
A) polymerization.
B) monomerization.
C) dimerization.
D) hydroxylation.
E) homogenization.
Answer: A
Section: 27-0

105) The first polymer, invented by A. Parke in 1856, was

A) Polyethlene.
B) Polyester.
C) Polystyrene.
D) Celluloid.
E) Teflon.
Answer: D
Section: 27-0

106) List the two main groups of polymers and give one example of each.
Answer: Polymers are divided into two main groups:
a) Biopolymers; for example DNA
b) Synthetic polymers; for example a polyester
Section: 27-0

107) Which of the following polymers can be recycled?

A) poly(ethylene terephthalate)
B) high density polyethylene
C) poly(vinyl chloride)
D) A and B
E) all of the above
Answer: D
Section: 27-13

108) Isoprene is the monomer present in

A) natural rubber.
B) synthetic rubber.
C) gutta percha.
D) A and B.
E) A and C.
Answer: E
Section: 27-8

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109) Which of the following polymers is being used in medical applications such as sutures,
stents etc.
A) poly(ethylene terephthalate)
B) poly(vinylchloride)
C) polylactides
D) polyhydroxyalkanoates
E) NyloN 66
Answer: C
Section: 27-14

110) Vulcanization involves crosslinking of polymer chains through

A) disulfide bonds
B) amide bonds
C) ester bonds
D) double bonds
E) manual twisting
Answer: A
Section: 27-8

111) Which of the following polymers is used in bullet-proof vests?

A) Nylon 66
B) Kevlar
C) Mylar
D) Lexan
E) Teflon
Answer: B
Section: 27-11

112) Kevlar is one of the hardest polymer known. The exceptional strength of Kevlar is
attributed to
A) amide bonds between the chains that form a sheet-like structure.
B) ester bonds between the chains that form a sheet-like structure.
C) disulfide bonds between the chains that form a sheet-like structure.
D) hydrogen bonds between the chains that form a sheet-like structure.
E) none of the above
Answer: D
Section: 27-11

113) Epoxy resin is a copolymer of

A) bisphenol A and epichlorohydrin.
B) bisphenol A and diphenyl carbonate.
C) bisphenol A and dimethylterephthalate.
D) bisphenol A and ethylene glycol.
E) bisphenol A and 1,4-diaminobenzene.
Answer: A
Section: 27-11

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114) What is most widely used plasticizer?
A) epichlorohydrin
B) diphenyl carbonate
C) dimethylterephthalate
D) ethylene glycol
E) di-2-ethylhexylphthalate
Answer: E
Section: 27-3
GLO: G5

115) Which of the following is not a step-growth polymer?

A) Nylon 66
B) Kevlar
C) Mylar
D) Lexan
E) Teflon
Answer: E
Section: 27-3

116) Saran wrap is a copolymer of

A) vinyl chloride and vinylidene chloride.
B) styrene and vinyl chloride.
C) acrylonitrile and styrene.
D) acrylonitrile and vinyl chloride.
E) vinyl chloride and isoprene.
Answer: A
Section: 27-9
GLO: G5

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