Test Bank For Organic Chemistry Mechanistic Patterns 1st Edition by Ogilvie

Test Bank for Organic Chemistry Mechanistic Patterns 1st Edition by Ogilvie
Test Bank for Organic Chemistry Mechanistic

Patterns 1st Edition by Ogilvie
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Name: Class: Date:
CHAPTER 10 - Synthesis Using Aromatic Materials: Electrophilic Aromatic Substitution and Directed
Ortho Metalation
1. Which of the following compounds will the reaction below lead to?
a.
b.
c.
d.
ANSWER: b
2. Which of the following best describes the substituent on the molecule shown below?
a. It is ortho/para directing and electron donating by electron-delocalization.

b. It is meta directing and electron withdrawing by electron-delocalization.
c. It is ortho/para directing and electron donating by electron-delocalization.
d. It is meta directing and electron withdrawing by electron-delocalization.
ANSWER: a
3. Which of the following best describes the substituent on the molecule shown below?
a. It is ortho/para directing by electron-delocalization.

b. It is meta directing by electron-delocalization.
c. It is ortho/para directing by induction.
d. It is meta directing by induction.
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Name: Class: Date:
Ortho Metalation
ANSWER: b
4. Compared to benzene, what best describes the reactivity of nitrobenzene (shown below) to SEAr reactions?
a. It is more reactive than benzene.

b. It is less reactive than benzene.
c. It is similarly reactive as benzene.
d. There is not enough information to determine reactivity.
ANSWER: b
5. Which of the following best describes the two molecules shown below?
a. A is more reactive to SEAr than B and is meta directing.

b. A is less reactive to SEAr than B and is meta directing.
c. A is more reactive to SEAr than B and is para/ortho directing.
d. A is less reactive to SEAr than B and is para/ortho directing.
ANSWER: c
6. Which of the following is an intermediate in the reaction shown below?
a.
b.

Name: Class: Date:
Ortho Metalation
c.
d.
ANSWER: d
7. What is the role of FeBr3 in the following reaction?
a. It activates bromine and makes it more nucleophilic.

b. It activates bromine and makes it more electrophilic.
c. It activates toluene and makes it more nucleophilic.
d. It activates toluene and makes it more electrophilic.
ANSWER: b
8. What is the role of sulfuric acid in the following reaction scheme?
a. to protonate the aromatic ring and make it a better electrophile

b. to form dipole interactions with the developing positive charge in the aromatic ring
c. to protonate nitric acid to form the nitronium ion
d. to regenerate nitric acid
ANSWER: c
9. Which of the following would be the product of the reaction shown below?
a.

Name: Class: Date:
Ortho Metalation
b.
c.
d.
ANSWER: d
10. Which of the following would be the product of the reaction shown below?
a.
b.
c.
d. No reaction would occur.

ANSWER: d
11. What set of reagents would most effectively produce ethylbenzene from benzene shown below?
a. AlCl3, EtCl

Name: Class: Date:
Ortho Metalation
b.
1) AlCl3, 2) Zn/HCl
c. 1) MgBrEt, ether 2) H3O+
d. 1) EtBr
ANSWER: b
12. As substituents on aromatic rings, which of the following best describes halides?
a. meta directing and activating
b. meta directing and deactivating
c. ortho/para directing and activating
d. ortho/para directing and deactivating
ANSWER: d
13. What sequence of reagents would best achieve the transformation shown below?
a. 1) Br2, FeBr3 2) HNO3, H2SO4 3) Fe, HCL

b. 1) Br2, FeBr3 2) Fe, HCL 3) HNO3, H2SO4
c. 1) HNO3, H2SO4 2) Br2, FeBr3 3) Fe, HCL
d. 1) HNO3, H2SO4 2) Fe, HCL 3) Br2, FeBr3
ANSWER: c
14. Why is aniline NOT compatible with Friedel-Crafts alkylation?

a. because the amino group is too electron withdrawing to undergo Friedel-Crafts alkylation
b. because the nitrogen acts as a Lewis base and reacts with AlCl3 instead
c. because the amino group is too electron donating to undergo Friedel-Crafts alkylation
d. because the nitrogen group acts as a Lewis acid and reacts with AlCl3 instead
ANSWER: b
15. Why is nitrobenzene NOT compatible with Friedel-Crafts alkylation?

a. because the nitro group is too electron withdrawing to undergo Friedel-Crafts alkylation
b. because the nitrogen acts as a Lewis base and reacts with AlCl3 instead
c. because the nitro group is too electron donating to undergo Friedel-Crafts alkylation
d. because the nitrogen group acts as a Lewis acid and reacts with AlCl3 instead
ANSWER: a
16. What would be the expected product of the following reaction?

Name: Class: Date:
Ortho Metalation
a.
b.
c.
d. No product would form.

ANSWER: a
17. What route would work best for the synthesis of the following aromatic molecule from benzene shown
below?
a.
1)AlCl3, 2) HNO3, H2SO4
b.
1)HNO3, H2SO4 2) AlCl3,
c.
1)HNO3,
d. This product cannot be formed since Friedel-Crafts reactions are incompatible with nitrobenzene.
ANSWER: a
18. Which of the following statements best describes the set of aromatic molecules show below?

Name: Class: Date:
Ortho Metalation
a. A is the most activated and B is the least activated towards SEAr reactions.
b. C is the most activated and B is the least activated towards SEAr reactions.
c. A is the most activated and C is the least activated towards SEAr reactions.
d. B is the most activated and A is the least activated towards SEAr reactions.
ANSWER: c
19. Which of the following statements best describes the set of aromatic molecules, show below?
a. A is the most activated and B is the least activated towards SEAr reactions.
b. C is the most activated and B is the least activated towards SEAr reactions.
c. A is the most activated and C is the least activated towards SEAr reactions.
d. B is the most activated and C is the least activated towards SEAr reactions.
ANSWER: d
20. Which of the following best describes the carboxylic acid substituent in benzoic acid shown below?
a. It is ortho/para directing and electron donating by electron-delocalization.

b. It is meta directing and electron withdrawing by electron-delocalization.
c. It is ortho/para directing and electron donating by electron-delocalization.
d. It is meta directing and electron withdrawing by electron-delocalization.
ANSWER: b
21. Predict the product of the following reaction shown below.

Name: Class: Date:
Ortho Metalation
a.
b.
c.
d.
ANSWER: d
22. Which molecule will react faster with Br2 in the presence of iron bromide and why?
a. A because the amino group makes the ring more negative through charge delocalization
b. B because the nitro group makes the ring more negative through charge delocalization
c. A because the amino group makes the ring less negative through charge delocalization
d. B because the nitro group makes the ring less negative through charge delocalization
ANSWER: a
a.

Name: Class: Date:
Ortho Metalation
b.
c.
d.
ANSWER: a
24. Which of the following aromatic molecules would NOT be suitable for directed ortho metalation?
a.
b.
c.
d.
ANSWER: b
25. Which of the following molecules would be required as a reacting to form the product in the reaction
scheme shown below?

Name: Class: Date:
Ortho Metalation
a.
b.
c.
d. The transformation shown above is not possible.

ANSWER: a
26. Which of the following molecules would be required as a reacting to form the product in the reaction
scheme shown below?
a.
b.
c.
d. The transformation shown above is not possible.

ANSWER: c
27. Which of the following best describes FeBr3 in the reaction shown below?
a. Lewis acid
b. Lewis base
c. solvent
d. nucleophile
ANSWER: a

Name: Class: Date:
Ortho Metalation
28. Which of the following statements best describes the reaction shown below?
a. Benzene is the nucleophile; HNO3 is the electrophile.

b. Benzene is the electrophile; HNO3 is the nucleophile.
c. Benzene is the nucleophile; NO2 is the electrophile.
d. Benzene is the electrophile; NO2 is the nucleophile.
ANSWER: c
29. What is the IUPAC name for m-xylene?

a. 1,2-dimethylbenzene
b. 1,3-dimethylbenzene
c. 2-methylphenol
d. 3-methylphenol
ANSWER: b
30. What is the common name for methoxybenzene?

a. analine
b. anisole
c. phenol
d. toluene
ANSWER: b
a.

Name: Class: Date:
Ortho Metalation
b.
c.
d.
ANSWER: c
a.
b.
c.

Name: Class: Date:
Ortho Metalation
d.
ANSWER: c
33. Which of the following best describes the role of aluminum chloride in a Friedel-Crafts reaction?
a. It is a Lewis base and is used to activate the alkyl halide.
b. It is a Lewis acid and is used to activate the alkyl halide.
c. It is a Lewis base and is used to activate the aromatic ring.
d. It is a Lewis acid and is used to activate the aromatic ring.
ANSWER: b
34. In an SEAr reaction, how would you describe an amino group on an aromatic ring?
a. strongly deactivating
b. weakly deactivating
c. weakly activating
d. strongly activating
ANSWER: d
35. In an SEAr reaction, how would you describe an alkyl group on an aromatic ring?
a. strongly deactivating
b. weakly deactivating
c. weakly activating
d. strongly activating
ANSWER: c
36. In an SEAr reaction, how would you describe a halogen group on an aromatic ring?
a. ortho/para directing and deactivating
b. ortho/para directing and activating
c. meta directing and deactivating
d. meta directing and activating
ANSWER: a
37. Which of the following best describes an activating group in an SEAr reaction?
a. electron rich with a smaller ÄG of reaction relative to benzene
b. electron poor with a smaller ÄG of reaction relative to benzene
c. electron rich with a larger ÄG of reaction relative to benzene
d. electron poor with a larger ÄG of reaction relative to benzene
Name: Class: Date:
Ortho Metalation
ANSWER: a
38. Which of the following best describes a deactivating group in an SEAr reaction?
a. electron rich with a smaller ÄG of reaction relative to benzene
b. electron poor with a smaller ÄG of reaction relative to benzene
c. electron rich with a larger ÄG of reaction relative to benzene
d. electron poor with a larger ÄG of reaction relative to benzene
ANSWER: d
a.
b.
c.
d.
ANSWER: a

Name: Class: Date:
Ortho Metalation
a.
b.
c.
d.
ANSWER: c
a.

Name: Class: Date:
Ortho Metalation
b.
c.
d.
ANSWER: d
42. What is the driving force for the last step in an SEAr mechanism?
a. stabilization of charge
b. loss of an acidic proton
c. gain of a double bond
d. restoration of aromaticity
ANSWER: d
43. What is the expected product of the reaction shown below?
a.
b.
c.

Name: Class: Date:
Ortho Metalation
d.
A mixture of and
ANSWER: d
44. What is the expected product of the reaction shown below?
a.
b.
c.
d.
A mixture of and
ANSWER: c
45. The role of FeBr3 in the bromination of benzene is to make bromine more nucleophilic.
a. True
b. False
ANSWER: False
Name: Class: Date:
Ortho Metalation
46. Friedel-Crafts acylation reactions run the risk of carbocation rearrangements.

a. True
b. False
ANSWER: False
47. Sulfate groups are meta directing substituents in SEAr reactions.

a. True
b. False
ANSWER: True
48. Nitro groups are activating substituents in SEAr reactions.

a. True
b. False
ANSWER: False
49. Alkyl groups are meta directing substituents in SEAr reactions.

a. True
b. False
ANSWER: False
50. Amino groups are ortho/para directing substituents in SEAr reactions.

a. True
b. False
ANSWER: True
51. Alcohol groups are activating substituents in SEAr reactions.

a. True
b. False
ANSWER: True
52. The aromatic ð electrons act as the nucleophile in SEAr reactions.

a. True
b. False
ANSWER: True
53. Sterics plays a role in whether a group adds ortho or para on an aromatic ring.
a. True
b. False
ANSWER: True
54. A secondary carbocation will undergo rearrangement to become a primary carbocation.

Name: Class: Date:
Ortho Metalation
a. True
b. False
ANSWER: False
55. In a Friedel-Crafts reaction, aluminum chloride acts as a Lewis acid.

a. True
b. False
ANSWER: True
56. Meta directing groups tend to be deactivating groups in SEAr reactions.

a. True
b. False
ANSWER: True
57. Aromatic ð bonds are more nucleophilic then non-aromatic ð bonds.

a. True
b. False
ANSWER: False
58. During an electrophilic aromatic substitution reaction, the aromatic ring becomes positively charged.
a. True
b. False
ANSWER: True
59. Carbocation rearrangements can involve either the movements of hydrides or alkyl groups.
a. True
b. False
ANSWER: True
60. Electron donating groups stabilize the arenium ion during SEAr reactions.
a. True
b. False
ANSWER: True
61. Acylation of an amine to an amide increases its activation potential in SEAr reactions.
a. True
b. False
ANSWER: False
62. Protonation of an amino group plays no role in its directing influence in SEAr reactions.
a. True
b. False
Name: Class: Date:
Ortho Metalation
ANSWER: False
63. Fluorination of an aromatic ring through a SEAr mechanism requires no catalyst.

a. True
b. False
ANSWER: True
64. Acyl groups are meta directing substituents in SEAr reactions.

a. True
b. False
ANSWER: True
65. SO3 is the nucleophile in the sulfation of aromatic rings.

a. True
b. False
ANSWER: False
66. Sulfate groups are considered deactivating groups in SEAr reactions.

a. True
b. False
ANSWER: True
67. Sulfate groups are considered para/ortho directors in SEAr reactions.

a. True
b. False
ANSWER: False
68. Iron filings in the presence of hydrochloric acid can reduce a nitro group into an amino group.
a. True
b. False
ANSWER: True
69. Iron filings in the presence of hydrochloric acid can reduce an aromatic ketone into an alkyl group.
a. True
b. False
ANSWER: False
70. Electron-donating substituents on aromatic rings act as _______________ directors in SEAr reactions.
ANSWER: ortho/para
71. Nitro groups are strongly _______________ substituents in SEAr reactions.

ANSWER: deactivating
Name: Class: Date:
Ortho Metalation
72. In an electrophilic aromatic substitution reaction, the aromatic group acts as a(n) _______________.
ANSWER: nucleophile
73. An alternative to electrophilic aromatic substitution reactions are DOM reactions, which stands for _______________.
ANSWER: directed ortho metalation
74. Friedel-Crafts acylation often results in a(n) _______________ functional group.

ANSWER: ketone
75. Friedel-Crafts alkylations cannot be performed in the presence of a(n) ________ or a(n) _______ group.
ANSWER: nitro, amino
76. Nitro groups on aromatic rings act as _______________ directors in SEAr reactions.
ANSWER: meta
77. The IUPAC name for anisole is _______________ .

ANSWER: methoxybenzene
78. The common name for aminobenzene is _______________ .

ANSWER: analine
79. _______________ is a Lewis acid required for Friedel-Crafts reactions

ANSWER: AlCl3
80. Design a reaction pathway to generate the following aromatic molecule from benzene. Show each intermediate.
ANSWER: The scheme is as follows. Note: steps 3 and 4 can be swapped.
81. Draw the mechanism for the following reaction. Show a resonance state that demonstrates the substituents effect on
regiochemistry.

Name: Class: Date:
Ortho Metalation
ANSWER: The mechanism is as follows:
82. Design a reaction pathway to generate the following aromatic molecule from benzene. Show each intermediate.
ANSWER: The scheme is as follows. Note: steps 3 and 4 can be swapped.
83. A chemist runs the following nitration reactions on benzofuran and indole shown below and gets the following
molecules as major products. Draw out the intermediate of each reaction and justify why each major product is obtained.
ANSWER: The intermediates are shown below. 1c is more stabilized than 2c since nitrogen is less electronegative than
oxygen and can better carry the positive charge, promoting that pathway for nitrogen over oxygen. Secondly,
Name: Class: Date:
Ortho Metalation
since oxygen is more electronegative, it destabilizes 2b more then nitrogen would destabilize 1b. Thus
benzofuran would prefer the top pathway and indole follows the bottom pathway.
84. Draw a mechanism to explain the following transformation.
ANSWER: The reaction mechanism is as follows. Note that a carbocation rearrangement occurs to turn a 1° carbocation
into a 2° carbocation.

Name: Class: Date:
Ortho Metalation
85. Predict the produce for the following reaction, draw a mechanism show a resonance state that influences the resulting
regiochemistry.
ANSWER: There are two possible answers—ortho or para addition. Para is shown below.
86. Draw the product of the reaction scheme shown below.
ANSWER: The product to the reaction is as follows:
87. Draw the mechanism for the DOM reaction shown below.
ANSWER: The reaction mechanism is as follows:

Test Bank for Organic Chemistry Mechanistic Patterns 1st Edition by Ogilvie
Name: Class: Date:
Ortho Metalation
88. List the reagents required to transform benzene into the product shown below.
ANSWER: The reaction conditions required are as follows:
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a. It is ortho/para directing and electron donating by electron-delocalization.

a. It is ortho/para directing by electron-delocalization.

a. It is more reactive than benzene.

a. A is more reactive to SEAr than B and is meta directing.

6. Which of the following is an intermediate in the reaction shown below?

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7. What is the role of FeBr3 in the following reaction?

a. It activates bromine and makes it more nucleophilic.

8. What is the role of sulfuric acid in the following reaction scheme?

a. to protonate the aromatic ring and make it a better electrophile

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d. No reaction would occur.

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a. 1) Br2, FeBr3 2) HNO3, H2SO4 3) Fe, HCL

14. Why is aniline NOT compatible with Friedel-Crafts alkylation?

15. Why is nitrobenzene NOT compatible with Friedel-Crafts alkylation?

16. What would be the expected product of the following reaction?

d. No product would form.

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a. It is ortho/para directing and electron donating by electron-delocalization.

21. Predict the product of the following reaction shown below.

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d. The transformation shown above is not possible.

d. The transformation shown above is not possible.

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a. Benzene is the nucleophile; HNO3 is the electrophile.

29. What is the IUPAC name for m-xylene?

30. What is the common name for methoxybenzene?

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43. What is the expected product of the reaction shown below?

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44. What is the expected product of the reaction shown below?

46. Friedel-Crafts acylation reactions run the risk of carbocation rearrangements.

47. Sulfate groups are meta directing substituents in SEAr reactions.

48. Nitro groups are activating substituents in SEAr reactions.

49. Alkyl groups are meta directing substituents in SEAr reactions.

50. Amino groups are ortho/para directing substituents in SEAr reactions.

51. Alcohol groups are activating substituents in SEAr reactions.

52. The aromatic ð electrons act as the nucleophile in SEAr reactions.

54. A secondary carbocation will undergo rearrangement to become a primary carbocation.

55. In a Friedel-Crafts reaction, aluminum chloride acts as a Lewis acid.

56. Meta directing groups tend to be deactivating groups in SEAr reactions.

57. Aromatic ð bonds are more nucleophilic then non-aromatic ð bonds.

63. Fluorination of an aromatic ring through a SEAr mechanism requires no catalyst.

64. Acyl groups are meta directing substituents in SEAr reactions.

65. SO3 is the nucleophile in the sulfation of aromatic rings.

66. Sulfate groups are considered deactivating groups in SEAr reactions.

67. Sulfate groups are considered para/ortho directors in SEAr reactions.

71. Nitro groups are strongly _______________ substituents in SEAr reactions.

74. Friedel-Crafts acylation often results in a(n) _______________ functional group.

77. The IUPAC name for anisole is _______________ .

78. The common name for aminobenzene is _______________ .

79. _______________ is a Lewis acid required for Friedel-Crafts reactions

ANSWER: The scheme is as follows. Note: steps 3 and 4 can be swapped.