chapter 15 test bank chem 200

Answer: D Topic: Synthesis Section: 15.6 Difficulty Level: Easy 27 Which of the following reactions could be used to synthesize tert-butylbenzene?. Topic: Synthesis Section: 15.6 Difficu

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Package Title: Solomons Test Bank

Course Title: Solomons 11e

Chapter Number: 15

Question Type: Multiple Choice

1) Which of these is the rate-determining step in the nitration of benzene?

a) Protonation of nitric acid by sulfuric acid

b) Protonation of sulfuric acid by nitric acid

c) Loss of a water molecule by the protonated species to produce the nitronium ion d) Addition of the nitronium to benzene to produce the arenium ion

e) Loss of a proton by the arenium ion to form nitrobenzene

Answer: D

Topic: Mechanisms and Intermediates

Section: 15.2

Difficulty Level: Medium

2) Which of these is the rate-determining step in the sulfonation of benzene?

a) Formation of SO3 from sulfuric acid

b) Protonation of SO3 sulfuric acid

c) Addition of SO3H+ to benzene to form the arenium ion

d) Loss of a proton from the arenium ion to form benzenesulfonic acid

e) None of these choices

Answer: C

Section: 15.2

3) Which of these is the rate-determining step in the bromination of benzene? a) Complexation of bromine with the iron(III) bromide catalyst

b) Formation of Br+ ion

c) Addition of Br+ to benzene to form the arenium ion

d) Loss of a proton from the arenium ion to form bromobenzene

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Answer: C

Section: 15.2

4) Which of the following structures contribute(s) to the resonance hybrid of the intermediate for ed when bromobenzene undergoes para-chlorination? m

5) Which of the following structures contribute(s) to the resonance hybrid of the intermediate formed when chlorobenzene undergoes para-chlorination?

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Section: 15.11

6) Which of the following structures contribute(s) to the resonance hybrid of the intermediate formed when acetanilide undergoes para-bromination?

7) Which of the following contributors to the resonance stabilized hybrid formed when aniline undergoes para-chlorination would be exceptionally stable?

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8) Consider the structures given below Which of them would be a relatively stable contributor

to the hybrid formed when toluene undergoes para bromination?

9) Which of the following structures does not contribute to the resonance hybrid of the

intermediate formed when nitrobenzene undergoes meta-chlorination?

+

: :

: : : : : : :

a) I

b) II

c) III

d) None of these contribute

e) All of these contribute

Answer: E

Section: 15.11

10) Consider the resonance forms shown for the arenium ionformed from the bromination of acetanilide Which resonance form contributes most to the overall resonance hybrid?

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11) Consider the resonance forms shown for the arenium ionformed from the bromination of acetanilide Which resonance form contributes most to the overall resonance hybrid?

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Section: 15.11

12) The electrophilic bromination or chlorination of benzene requires, in addition to the halogen:

Difficulty Level: Easy

13) In electrophilic aromatic substitution, the attacking species (the electrophile) necessarily is a: a) neutral species

b) positively charged species

14) Which of these liquids would be unsuitable as an inert solvent for a Friedel-Crafts reaction?

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Topic: Other EAS Considerations

Section: 15.8

15) Undesired polysubstitution of an aromatic nucleus is most likely to be encountered in the case of:

16) This substituent deactivates the benzene ring towards electrophilic substitution but directs the incoming group chiefly to the ortho and para positions

17) This molecule does not normally participate as a reactant in a Friedel-Crafts reaction

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Topic: Other EAS Considerations

Section: 15.8

18) Which one of these molecules can be a reactant in a Friedel-Crafts reaction?

19) Which one of these molecules can be a reactant in a Friedel-Crafts reaction?

20) Which reagent would you use as the basis for a simple chemical test that would distinguish between toluene and vinylbenzene (C6H5CH=CH2)?

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Topic: Functional Group Tests

Sections: 14.2, 14.3 and 15.3

21) Which reagent or test could you use to distinguish between phenylacetylene and

22) What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and HF? a) butylbenzene

Difficulty Level: Hard

23) What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and AlCl3?

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Answer: B

Topic: Nomenclature, Reaction Products

Section: 14.2 and 15.6

24) A mixture of chlorobenzene (1 mol) and acetanilide (1mol) is allowed to react with Br2 (0.5 mol) in the presence of trace amounts of FeBr3 What is the principal product of the competing reactions?

25) A mixture of chlorobenzene (1 mol) and anisole (1mol) is allowed to react with Br2 (0.5 mol)

in the presence of trace amounts of FeBr3 What is the principal product of the competing

26) Which of the following reactions could be used to synthesize tert-butylbenzene?

a)

H2SO4

C6H6 + CH2=C(CH3)2

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d) All of these choices

Answer: D

Topic: Synthesis

Section: 15.6

Answer: D

Topic: Synthesis

Section: 15.6

Answer: D

Topic: Synthesis

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Section: 15.6

29) Consider the following reaction: what is the expected product?

30) Which of the following reactions would yield isopropylbenzene as the major product?

b)

Benzene

H2SO4

CH3CHCH3OH

c)

Benzene

AlCl3

CH3CHCH3Cl

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c)

Benzene

AlCl3

CH3CHCH3Cl

a)

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33) Which of the following reactions would produce isopropylbenzene?

a)

Cl

AlCl3Benzene

d)

Br

AlCl3Benzene

e) All of these choices

Answer: E

Topic: Synthesis

Section: 15.6

34) Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?

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35) Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?

36) Which of the following reactions would produce cumene?

a)

Cl

AlCl3Benzene

d)

Br

AlCl3Benzene

e) All of these choices

Answer: E

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Topic: Synthesis

Section: 15.6

37) Which of the following reactions would yield cumene as the major product?

c)

Benzene

AlCl3

CH3CHCH3Cl

38) Which of the following reactions would give the product(s) indicated in substantial amounts (i.e., in greater than 50% yield)?

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a) I

b) II

c) III

Answer: E

Topic: Reaction Products

39) What would you expect to be the major product obtained from the following reaction?

HN O

III

HN O

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41) The major product(s) of the following reaction,

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42) What might be predicted to happen when the following substance undergoes Friedel-Crafts acylation?

CH2

O2N

a) Substitution occurs in ring B, p- to the methylene group

b) Substitution occurs in ring A, o- to the nitro group

c) Substitution occurs in ring A, o- to the methylene group

d) Substitution occurs in ring B, m- to the methylene group

e) None of these choices No reaction will occur

Answer: A

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43) What would be the product of the following reaction sequence?

IV

OH O

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OH O

IV

OH O

?

a) I

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i) SOCl2ii) C6H6, AlCl3iii) Zn(Hg), HCl, heat

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49) Which would be the product of the following reaction sequence?

IV

OH O

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OH O

a) I

b) II

c) III

d) IV

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e) V

Answer: C

53) Which would be the product, X, of the following reaction sequence?

i) benzene, AlCl3

O Ph

Ph

O O

54) Which would be the product, X, of the following reaction sequence?

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55) The major product(s), D, of the following reaction,

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56) The major product, D, of the following reaction,

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D

H2SO4SO3

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SO 3 H COOH

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O O

Br

O O

Br

O O

Br

III

O O Br

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HN O

Cl

HN O

Cl

HN O

Cl

III

HN O Cl

?

Cl2, FeCl3

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O Br

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64) What would you expect to be the major product obtained from the monobromination of dichlorobenzene?

Cl

Cl Br

a) I

b) II

c) III

d) Equal amounts of I and II

e) Equal amounts of I, II and III

Answer: B

65) Which would be the major product(s) of the following reaction?

d) I and II in roughly equal amounts

e) I and III in roughly equal amounts

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HN O

O2N

HN O

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O O

O2N

O O

NO2

O O

NO2

III

O O

68) What would be the major product(s) of the following reaction?

HNO3

H2SO4, heat ?

a) I

b) II

c) III

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71) What would you expect to be the major product(s) obtained from the mononitration of dichlorobenzene?

d) Equal amounts of I and II

e) Equal amounts of I, II and III

Answer: B

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72) What would you expect to be the major product(s) obtained from the following reaction?

73) The major product(s), D, of the following reaction

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O O

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Answer: A

d) I and II in roughly equal amounts

Answer: A

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IV

?

H2SO4

a) I

b) II

c) III

d) Equal amounts of I and IV

e) Equal amounts of II and IV

Answer: C

NO2O

NO2SO3H

b) II

c) III

d) Equal amounts of I and IV

e) Equal amounts of II and IV

Answer: C

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78) The major product(s), C, of the following reaction,

d) Approximately equal amounts of I and II

e) Approximately equal amounts of I and III

Answer: B

79) The major product(s), A, of the following reaction,

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Cl

Cl Cl

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Br

Br Br

Br

Br Br

excess NBS ROOR

82) The major product(s), A, of the following reaction,

?

Br Br

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83) What would be the major product of the following reaction?

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Br Br

?

Br Br

Br Br Br

Br

Br Br

I

excess NBS ROOR

Br Br

IV

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) I

a

b) II

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Br CCl3

opic: Reaction Products

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N N

N

N N

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Br2FeBr3

92) The reaction of benzene with (CH3)3CCH2Cl in the presence of anhydrous aluminum chloride produces principally which of these?

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93) The reaction of benzene with Clin the presence of anhydrous aluminum chloride produces principally which of these?

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94) The reaction of benzene with in the presence of anhydrous aluminum chloride produces principally which of these?

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