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Mastering Chemistry: A Molecular Approach Chapter 10

Total questions: 60

Worksheet time: 30mins

Name
Class
Date
1.

Identify the likely major product(s) of the reaction shown.

a)

I and III

b)

I and IV

c)

I

d)

III

e)

II

2.

Which of the following are possible termination steps in the chlorination of methane?

a)

III and IV

b)

II and IV

c)

I and III

d)

I and II

3.

Rank the following radicals in order of decreasing stability (most stable to least stable).

a)

III > II > I > IV

b)

III > I > II > IV

c)

II > III > I > IV

d)

III > IV > II > I

e)

IV > I > II > III

4.

In the molecule shown below, determine which of the highlighted C-H bonds (from a to e) is expected to have the lowest bond dissociation energy.

a)

C-Hd

b)

C-Ha

c)

C-Hc

d)

C-Hb

e)

C-He

5.

What reagents would best accomplish the following synthesis?

a)

Br2

b)

PBr3

c)

NBS, heat

d)

CH3Br

6.

Which of the following is expected to function as an antioxidant?

a)

II

b)

I

c)

III

d)

I, II, III, and IV

e)

IV

7.

Which term most accurately describes the process shown below?

a)

coupling

b)

hydrogen abstraction

c)

halogen abstraction

d)

elimination

e)

homolytic cleavage

8.

Which of the following would you expect to function as an initiator at the lowest temperature?

a)

III

b)

II

c)

IV

d)

I

9.

Which term most accurately describes the process shown below?

a)

halogen abstraction

b)

hydrogen abstraction

c)

coupling

d)

elimination

e)

homolytic cleavage

10.

Which of the following is expected to be a major product for the reaction shown below?

a)

I

b)

II

c)

IV

d)

III

11.

Rank the following radicals in order of decreasing stability (most stable to least stable).

a)

III > I > II > IV

b)

IV > I > II > III

c)

III > IV > II > I

d)

III > II > I > IV

e)

II > I > III > IV

12.

Predict the product(s) of the following reaction.

a)

III

b)

II

c)

I, II, III, IV

d)

I, II

e)

I

13.

Predict the major product(s) of the following reaction.

a)

II and IV

b)

III and V

c)

V

d)

I and IV

e)

I

14.

Which of the following are the products of a homolytic cleavage of a C-C bond of ethane?

a)

II

b)

IV

c)

III

d)

I

15.

Identify the intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide and hydrogen peroxide.

a)

II

b)

III

c)

I

d)

IV

16.

Which of the following is an example of initiation?

a)

I

b)

II

c)

III

d)

IV

e)

None of the above

17.

Which of the following correctly describes the nature of the transition state of the rate-determining step of the free-radical bromination of methane?

a)

the transition state resembles the reactants more than the products

b)

the transition state equally resembles products and reactants

c)

the transition state resembles the products more than the reactants

18.

Which term best describes the process shown below?

a)

elimination

b)

initiation

c)

termination

d)

neutralization

e)

propagation

19.

Determine the repeat unit for the polymer produced in the following reaction.

a)

II

b)

I

c)

III

d)

IV

20.

Poly(methyl methacrylate) (PMMA) is a light, shatter-resistant plastic prepared by the free-radical polymerization of methyl methacrylate (shown below). What is the repeat unit of PMMA?

a)

III

b)

IV

c)

II

d)

I

21.

Of the four choices shown, which is likely to be a major product of the reaction below?

a)

I

b)

II

c)

III

d)

IV

22.

Which term most accurately describes the process shown below?

a)

homolytic cleavage

b)

hydrogen abstraction

c)

proton transfer

d)

coupling

e)

halogen abstraction

23.

Which of the following is the correct name for the major product of the following reaction?

a)

(S)-3-bromo-3-ethylbutane

b)

(R)-3-bromo-3-ethylbutane

c)

(R)-3-bromo-3-methylpentane

d)

(S)-3-bromo-3-methylpentane

e)

3-bromo-3-methylpentane

24.

Predict the major product obtained upon radical bromination of t-butylcyclohexane.

a)

1-bromo-1-tert-butylcyclohexane

b)

2-bromo-1-tert-butylcyclohexane

c)

3-bromo-1-tert-butylcyclohexane

d)

4-bromo-1-tert-butylcyclohexane

e)

1-bromo-1,1-dimethylethylcyclohexane

25.

Identify an example of initiation.

a)

homolytic cleavage

b)

heterolytic cleavage

c)

hydrogen addition

d)

hydrogen abstraction

e)

coupling

26.

Which of the following are possible product(s) of the reaction shown?

a)

I, III, IV, V

b)

I, II, III, IV, IV

c)

I, II

d)

I

e)

I, II, IV, V

27.

Identify an example of propagation.

a)

hydrogen addition

b)

hydrogen abstraction

c)

heterolytic cleavage

d)

coupling

e)

homolytic cleavage

28.

Predict the major product(s) of the reaction shown below.

a)

II and III

b)

II

c)

III

d)

IV

e)

I

29.

Which of the following is most reactive towards chlorination?

a)

ethane

b)

chloroform

c)

dichloromethane

d)

methane

e)

chloromethane

30.

Which of the following shows the correct products initially formed when ozone absorbs ultraviolet light?

a)

II

b)

IV

c)

III

d)

I

31.

Identify an example of termination.

a)

homolytic cleavage

b)

hydrogen abstraction

c)

heterolytic cleavage

d)

hydrogen addition

e)

coupling

32.

Which of the following is the most stable radical?

a)

I

b)

V

c)

IV

d)

II

e)

III

33.

Which monomer is used for the synthesis of poly(vinyl chloride)?

a)

1,2-dichloroethene

b)

1-chloroethene

c)

1-chloro-1-propene

d)

1-chloroethane

34.

Which of the labeled C-H bonds is the weakest?

a)

C-Hd

b)

C-He

c)

C-Ha

d)

C-Hc

e)

C-Hb

35.

Which term best describes the process shown below?

a)

neutralization

b)

propagation

c)

termination

d)

elimination

e)

initiation

36.

Which of the following is expected to function as an antioxidant?

a)

II

b)

I

c)

I, II, III, and IV

d)

III

e)

IV

37.

What reagents would best accomplish the following synthesis?

a)

PBr3

b)

CH3Br

c)

NBS, heat

d)

Br2

38.

Which monomer is used for the synthesis of Teflon?

a)

tetrafluoromethane

b)

1,1,2,2-tetrafluoroethene

c)

1,1,2,2-tetrafluoropropene

d)

1,1-difluoroethene

39.

Poly(methyl methacrylate) (PMMA) is a light, shatter-resistant plastic prepared by the free-radical polymerization of methyl methacrylate (shown below). What is the repeat unit of PMMA?

a)

III

b)

IV

c)

II

d)

I

40.

Free radical chlorination of ethane can produce higher halogenation products such as dichloroethane, trichloroethane, tetrachloroethane, pentachloroethane, and hexachloroethane. How could the production of higher halogenated products be minimized?

a)

use equimolar chlorine and ethane

b)

use an excess of ethane

c)

use an excess of chlorine

d)

it is not possible to minimize the production of higher halogenated products

41.

Rank the following radicals in order of decreasing stability (most stable to least stable).

a)

III > II > I > IV

b)

III > IV > II > I

c)

IV > I > II > III

d)

III > I > II > IV

e)

II > I > III > IV

42.

Compound A has molecular formula C9H20. Compound A produces exactly three constitutional isomers upon monochlorination, and one major constitutional isomer upon monobromination. Which of the following are possible structures of compound A?

a)

V

b)

IV

c)

I

d)

III

e)

II

43.

Identify the intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide in the presence of peroxide.

a)

II

b)

I

c)

IV

d)

III

44.

Which term best describes the process shown below?

a)

initiation

b)

neutralization

c)

elimination

d)

propagation

e)

termination

45.

Which term most accurately describes the process shown below?

a)

elimination

b)

homolytic cleavage

c)

hydrogen abstraction

d)

coupling

e)

halogen abstraction

46.

Which of the following is the most stable radical?

a)

II

b)

V

c)

IV

d)

I

e)

III

47.

Which term most accurately describes the process shown below?

a)

hydrogen abstraction

b)

halogen abstraction

c)

proton transfer

d)

coupling

e)

homolytic cleavage

48.

Identify the intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide and hydrogen peroxide.

a)

III

b)

I

c)

II

d)

IV

49.

Which of the following shows the initiation step of monochlorination of methane?

a)

I

b)

III

c)

I and II

d)

IV

e)

II

50.

Predict the major product(s) of the reaction shown below.

a)

I

b)

II

c)

IV

d)

II and III

e)

III

51.

Which of the following are possible termination steps in the chlorination of methane?

a)

II and IV

b)

I and II

c)

I and III

d)

III and IV

52.

Identify an example of initiation.

a)

heterolytic cleavage

b)

hydrogen abstraction

c)

hydrogen addition

d)

coupling

e)

homolytic cleavage

53.

Predict the major product obtained upon radical bromination of t-butylcyclohexane.

a)

1-bromo-1,1-dimethylethylcyclohexane

b)

4-bromo-1-tert-butylcyclohexane

c)

3-bromo-1-tert-butylcyclohexane

d)

2-bromo-1-tert-butylcyclohexane

e)

1-bromo-1-tert-butylcyclohexane

54.

Which of the following is expected to be a major product for the reaction shown below?

a)

I

b)

IV

c)

III

d)

II

55.

Which of the following is an example of termination?

a)

I

b)

II

c)

III

d)

IV

e)

None of the above

56.

Identify the likely major product(s) of the reaction shown.

a)

I and III

b)

I and IV

c)

III

d)

II

e)

I

57.

Which of the following shows the correct products initially formed when ozone absorbs ultraviolet light?I

a)

I

b)

II

c)

III

d)

IV

58.

Which term most accurately describes the process shown below?

a)

elimination

b)

halogen abstraction

c)

hydrogen abstraction

d)

coupling

e)

homolytic cleavage

59.

Which of the labeled C-H bonds is the weakest?

a)

C-Hd

b)

C-Hb

c)

C-He

d)

C-Ha

e)

C-Hc

60.

Predict the major product(s) of the following reaction.

a)

IV

b)

I and II

c)

II

d)

III

e)

I

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