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Organic Chemistry, 6e (Smith)

Chapter 28 Synthetic Polymers

1) Which of the following monomers yields the polymer shown below?

A) A
B) B
C) C
D) D

Answer: B
Difficulty: 1 Easy
Section: 28.01
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

2) Which of the following is the repeating unit in polyvinyl chloride (PVC)?

A) A
B) B
C) C
D) D

Answer: A
Difficulty: 1 Easy
Section: 28.01
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

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written consent of McGraw-Hill Education.
3) Which of the following is (are) addition polymer(s)?

I. polypropylene
II. Teflon
III. nylon

A) Only I
B) Only II
C) Only III
D) Both I and II

Answer: D
Difficulty: 1 Easy
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28
Accessibility: Keyboard Navigation

4) Which of the following is (are) condensation polymer(s)?

I. polypropylene
II. Teflon
III. nylon

A) Only I
B) Only II
C) Only III
D) Both II and III

Answer: C
Difficulty: 1 Easy
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28
Accessibility: Keyboard Navigation

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written consent of McGraw-Hill Education.
5) Which one of the following monomers undergoes cationic polymerization most readily?
A) H2C=CH2
B) H2C=CHCH3
C) H2C=C(CH3)2
D) H2C=CHCN

Answer: C
Difficulty: 1 Easy
Section: 28.03
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28
Accessibility: Keyboard Navigation

6) Which one of the following monomers undergoes anionic polymerization most readily?
A) H2C=CH2
B) H2C=CHCH3
C) H2C=C(CH3)2
D) H2C=CHCN

Answer: D
Difficulty: 1 Easy
Section: 28.03
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28
Accessibility: Keyboard Navigation

7) In which type of polymer are the chains packed less tightly together, resulting in lower
melting points and a softer texture?
A) Isotactic polymers
B) Syndiotactic polymers
C) Atactic polymers
D) Cross-linked polymers

Answer: C
Difficulty: 1 Easy
Section: 28.03
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28
Accessibility: Keyboard Navigation

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written consent of McGraw-Hill Education.
8) Which of the following best describes the polymer chain shown below?

A) Atactic polypropylene
B) Isotactic polypropylene
C) Syndiotactic polypropylene
D) Cross-linked polypropylene

Answer: B
Difficulty: 1 Easy
Section: 28.04
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

9) Which of the following is used to make Teflon?


A) Fluoroethene
B) 1,1,4,4-Tetrafluorobutadiene
C) 1,2-Difluoroethene
D) Tetrafluoroethylene

Answer: D
Difficulty: 1 Easy
Section: 28.05
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28
Accessibility: Keyboard Navigation

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written consent of McGraw-Hill Education.
10) Which of the following best describes the polymer chain shown below?

A) Atactic polypropylene
B) Isotactic polypropylene
C) Syndiotactic polypropylene
D) Cross-linked polypropylene

Answer: C
Difficulty: 2 Medium
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

11) The monomer used to make superglue is shown below. Which of the following methods of
polymerization is most suitable for this type of monomer?

A) Free-radical chain-growth
B) Cationic chain-growth
C) Anionic chain-growth
D) Acid-catalyzed step-growth

Answer: C
Difficulty: 1 Easy
Section: 28.04
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

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written consent of McGraw-Hill Education.
12) Which type of polymerization process uses benzoyl peroxide (or other peroxides) as an
initiator?
A) Free-radical chain-growth
B) Cationic chain-growth
C) Anionic chain-growth
D) Acid-catalyzed step-growth

Answer: A
Difficulty: 1 Easy
Section: 28.04
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28
Accessibility: Keyboard Navigation

13) Which of the following is the monomer that gives the polymer shown below?

A) A
B) B
C) C
D) D

Answer: D
Difficulty: 1 Easy
Section: 28.06
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

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written consent of McGraw-Hill Education.
14) What modification occurs when a small amount of p-divinylbenzene is added to the
polymerization reaction of styrene to form polystyrene? (Recall that the vinyl group is —
CH=CH2.)
A) Cross-linking of the polystyrene
B) Isotactic stereochemistry of the polystyrene
C) Syndiotactic stereochemistry of the polystyrene
D) "Softening" of the polystyrene by a plasticizer

Answer: A
Difficulty: 2 Medium
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28
Accessibility: Keyboard Navigation

15) Identify the repeating unit in the polymer formed from the following reaction sequence.

A) A
B) B
C) C
D) D

Answer: B
Difficulty: 1 Easy
Section: 28.03
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

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written consent of McGraw-Hill Education.
16) The acid-catalyzed dimerization of isobutylene gives a mixture of two isomeric alkenes, A
and B. Hydrogenation of this mixture gives a single C8H18 hydrocarbon. What is the structure of
this hydrocarbon?

A) 2,2,4-Trimethylpentane
B) 2,3,4-Trimethylpentane
C) 2,4-Dimethylhexane
D) 2,5-Dimethyhexane

Answer: A
Difficulty: 1 Easy
Section: 28.03
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

17) The repeating unit of poly(methyl methacrylate) is shown below. Which one of the following
is the monomer used to make poly(methyl methacrylate)?

A) A
B) B
C) C
D) D

Answer: B
Difficulty: 1 Easy
Section: 28.03
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

8
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written consent of McGraw-Hill Education.
18) Which of the following monomers is used to make the polymer carbowax, shown below?

A) A
B) B
C) C
D) D

Answer: D
Difficulty: 1 Easy
Section: 28.03
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

19) Which of the following initiators can be used for anionic chain-growth polymerization?
A) Benzoyl peroxide
B) CH3CH2CH2CH2Li
C) BF3
D) Al(CH2CH3)3, TiCl4

Answer: B
Difficulty: 1 Easy
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 2. Understand
Chapter: 28
Accessibility: Keyboard Navigation

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written consent of McGraw-Hill Education.
20) Which of the following initiators can be used for free radical chain-growth polymerization?
A) Benzoyl peroxide
B) CH3CH2CH2CH2Li
C) BF3
D) Al(CH2CH3)3, TiCl4

Answer: A
Difficulty: 1 Easy
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 2. Understand
Chapter: 28
Accessibility: Keyboard Navigation

21) Which of the following initiators is used to make isotactic polypropylene?


A) Benzoyl peroxide
B) CH3CH2CH2CH2Li
C) BF3
D) Al(CH2CH3)3, TiCl4

Answer: D
Difficulty: 2 Medium
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 2. Understand
Chapter: 28
Accessibility: Keyboard Navigation

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written consent of McGraw-Hill Education.
22) The repeating unit of a polymer is shown below. This polymer is formed by

A) addition of ethylene.
B) addition of trans-2-butene.
C) 1,2 addition of butadiene.
D) 1,4 addition of butadiene.

Answer: D
Difficulty: 2 Medium
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

23) Vulcanization is the process of cross-linking polymer chains in rubber using what chemical?
A) Sulfur
B) Formaldehyde
C) Benzoyl peroxide
D) Ethylene glycol

Answer: A
Difficulty: 1 Easy
Section: 28.05
Topic: Synthetic Polymers
Bloom's: 1. Remember
Chapter: 28
Accessibility: Keyboard Navigation

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written consent of McGraw-Hill Education.
24) What monomer(s) would be used to make the polyester shown below?

A) Butanedioic acid
B) 4-Hydroxybutanal
C) 4-Hydroxybutanoic acid
D) Butanedioic acid and 1,4-butanediol

Answer: C
Difficulty: 2 Medium
Section: 28.06
Topic: Synthetic Polymers
Bloom's: 2. Understand
Chapter: 28

25) Which of the following is the repeating unit of the polymer formed in the polymerization of
p-hydroxybenzoic acid?

A) A
B) B
C) C
D) D

Answer: A
Difficulty: 1 Easy
Section: 28.06
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

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written consent of McGraw-Hill Education.
26) Identify the monomer(s) needed to make the following polyester.

A) 3-Hydroxybutanoic acid
B) Butanedioic acid
C) Butanedioic acid and ethylene glycol
D) Butanedioic acid and ethanol

Answer: C
Difficulty: 2 Medium
Section: 28.06
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

27) Which of the following is (are) repeating unit(s) of step-growth polymers?

A) Only I
B) Only II
C) Only III
D) I and II

Answer: D
Difficulty: 2 Medium
Section: 28.06
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

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written consent of McGraw-Hill Education.
28) Bakelite is formed by the acid-catalyzed polymerization of phenol with formaldehyde. What
is (are) the product(s) of the first step in this polymerization, shown below? (Note: in the answers
below the hydroxymethyl group is -CH2OH.)

A) Ortho and para-hydroxybenzaldehyde


B) Meta-hydroxybenzaldehyde
C) Ortho and para-(hydroxymethyl)phenol
D) Meta-(hydroxymethyl)phenol

Answer: C
Difficulty: 2 Medium
Section: 28.07
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

29) What is the purpose of plasticizers?


A) To harden plastics
B) To soften plastics
C) To initiate polymerizations
D) To cross-link polymer chains

Answer: B
Difficulty: 1 Easy
Section: 28.07
Topic: Synthetic Polymers
Bloom's: 1. Remember
Chapter: 28
Accessibility: Keyboard Navigation

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written consent of McGraw-Hill Education.
30) Which of the following is the repeating unit of the polymer formed in the polymerization
reaction shown below?

A) A
B) B
C) C
D) D

Answer: B
Difficulty: 2 Medium
Section: 28.03
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

31) What is the name given to polymers that soften when heated and harden when cooled?
A) Cross-linked polymers
B) Copolymers
C) Thermosetting polymers
D) Thermoplastics

Answer: D
Difficulty: 1 Easy
Section: 28.07
Topic: Synthetic Polymers
Bloom's: 1. Remember
Chapter: 28
Accessibility: Keyboard Navigation

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written consent of McGraw-Hill Education.
32) What is the structure of the polymer which results when styrene is reacted with BF3 and
H2O?

A) A
B) B
C) C
D) D

Answer: B
Difficulty: 2 Medium
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

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written consent of McGraw-Hill Education.
33) Rank the following monomers (X, Y and Z) in order of increasing ability to undergo anionic
polymerization, starting with the least reactive monomer.

A) Y< X < Z
B) Z < Y < X
C) X < Y < Z
D) Y < Z < X

Answer: D
Difficulty: 2 Medium
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

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written consent of McGraw-Hill Education.
34) Melamine and formaldehyde combine to form the polymer, Melmac®. How is Melmac®
classified, and what physical characteristics are consistent with its structure?

A) Polycarbonate, transparent
B) Polyurethane, elastic
C) Thermosetting, rigid
D) Thermoplastic, can be melted and molded into new shapes

Answer: C
Difficulty: 2 Medium
Section: 28.07
Topic: Synthetic Polymers
Bloom's: 4. Analyze
Chapter: 28

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written consent of McGraw-Hill Education.
35) Which monomer and which type of initiator would you use to synthesize the following
polymer?

A) A
B) B
C) C
D) D
E) E

Answer: A
Difficulty: 2 Medium
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

19
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written consent of McGraw-Hill Education.
36) Which of the following sets of products results if nylon 66 is treated with sulfuric acid?

A) A
B) B
C) C
D) D

Answer: D
Difficulty: 2 Medium
Section: 28.06
Topic: Synthetic Polymers
Bloom's: 3. Apply
Chapter: 28

20
Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior
written consent of McGraw-Hill Education.
37) What is the classification of the following polymer in which X and Y represent repeating
units?

A) Block copolymer
B) Homopolymer
C) Alternating copolymer
D) Random copolymer

Answer: A
Difficulty: 1 Easy
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 2. Understand
Chapter: 28

38) What is the classification of the following polymer in which X and Y represent repeating
units?

A) Block copolymer
B) Homopolymer
C) Alternating copolymer
D) Random copolymer

Answer: C
Difficulty: 1 Easy
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 2. Understand
Chapter: 28

21
Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior
written consent of McGraw-Hill Education.
39) What is the classification of the following polymer in which X and Y represent repeating
units?

A) Block copolymer
B) Homopolymer
C) Alternating copolymer
D) Random copolymer

Answer: D
Difficulty: 1 Easy
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 2. Understand
Chapter: 28

40) What is the name given to polymers with single monomers?


A) Homopolymers
B) Copolymers
C) Block polymers
D) Random polymers

Answer: A
Difficulty: 1 Easy
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 1. Remember
Chapter: 28
Accessibility: Keyboard Navigation

41) What is the name given to polymers with two or more different monomers?
A) Homopolymers
B) Copolymers
C) Block polymers
D) Random polymers

Answer: B
Difficulty: 1 Easy
Section: 28.02
Topic: Synthetic Polymers
Bloom's: 1. Remember
Chapter: 28
Accessibility: Keyboard Navigation

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written consent of McGraw-Hill Education.
42) What are the structures of the three monomers needed to synthesize the following polymer?

A) I
B) II
C) III
D) IV

Answer: A
Difficulty: 3 Hard
Section: 28.06
Topic: Synthetic Polymers
Bloom's: 4. Analyze
Chapter: 28

43) What type of polymer is Lexan?


A) Epoxy
B) Polyurethane
C) Polycarbonate
D) Polyamide

Answer: C
Difficulty: 1 Easy
Section: 28.06
Topic: Synthetic Polymers
Bloom's: 1. Remember
Chapter: 28
Accessibility: Keyboard Navigation

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written consent of McGraw-Hill Education.
44) What type of polymer is Nylon?
A) Epoxy
B) Polyurethane
C) Polycarbonate
D) Polyamide

Answer: D
Section: 28.06
Topic: Synthetic Polymers
Bloom's: 1. Remember
Chapter: 28
Accessibility: Keyboard Navigation

45) What type of polymer is Spandex?


A) HDPE
B) Polyurethane
C) Polycarbonate
D) Polyamide

Answer: B
Difficulty: 1 Easy
Section: 28.06
Topic: Synthetic Polymers
Bloom's: 1. Remember
Chapter: 28
Accessibility: Keyboard Navigation

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written consent of McGraw-Hill Education.

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