Multiple Choice

Section: 9.1 and 9.2
Difficulty Level: Medium 1. How many Kekule structures are possible for benzene, naphthalene, and anthracene ?

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a) I: 3, II: 4, III: 4 b) I: 2, II:3, III: 4 c) I: 2, II: 4, III: 4 d) I: 3, II: 3, III: 4

Section: 9.2
Difficulty Level: Medium
2. Which structures are aromatic?

a) II, III b) III, IV c) I, III d) II, IV

Section: 9.2
Difficulty Level: Hard
3. How many π-orbital electrons are in the following molecule?

[pic] a) imidazole: 5, adenine: 10, caffeine: 5 b) imidazole: 6, adenine: 9, caffeine: 6 c) imidazole: 6, adenine: 10, caffeine: 6 d) imidazole; 4, adenine, 9, caffeine, 5

Section: 9.3
Difficulty Level: Easy
4. Which structures have the correct IUPAC names?

[pic] a) I, II b) III, IV c) I, IV d) II, III

Section: 9.3
Difficulty Level: Easy
5. Which of the named compounds have correct structures?

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a) I, II, IV b) I, III, IV c) I, IV, V d) II, III, V

Section: 9.2 and 9.3
Difficulty Level: Easy
6. How many mono-bromobenzenes are possible?

a) 1 b) 2 c) 3 d) 4

Section: 9.2 and 9.3
Difficulty Level: Medium
7. How many bromo-naphthalenes are possible?

a) 1
b) 2
c) 3
d) 4

Section: 9.2 and 9.3
Difficulty Level: Medium
8. How many mono-bromoanthracenes are possible?

a) 1
b) 2
c) 3
d) 4

Section: 9.6
Difficulty Level: Medium
9. Which is the electrophile in the nitration of benzene?

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a) I
b) II
c) III
d) IV

Section: 9.6
Difficulty Level: Medium
10. Arrange the compounds in order of decreasing reactivity towards the aromatic nitration reaction?

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a) I > III > IV > II b) III > II > I > IV c) II > I > III > IV d) IV > II > III > I

Section: 9.6
Difficulty Level: Medium
11. Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution (lowest first).

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a) III < I < IV < II
b) I < III < II < IV
c) II < I < IV < III
d) IV < II < I < III

Section: 9.6
Difficulty Level: Medium
12. Which electrophiles are formed – at different stages of the reaction, by the reaction of phenol and acetone in the presence of phosphoric acid (a strong mineral acid)?

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a) I and IV b) II and III c) III and IV d) II and IV

Section: 9.6
Difficulty Level: Medium
13. Which is the electrophile in the following reaction?

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a) I
b) II
c) III
d) IV

Section: 9.6
Difficulty Level: Hard
14. Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution (lowest first).

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a) III, II, I, IV b) IV, II, I, III c) III, I, II, IV d) I, II, III, IV

Section: 9.6
Difficulty Level: Hard
15. Which are the major reaction products of the following reaction, which is carried out in an inert solvent?

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a) I and II b) II and III c) III and IV d) II and IV

16. Which are the major reaction products of the following reaction, which is carried out in an inert solvent? (HINT: add the lone pairs to the line-angle formula first.)

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a) I and II
b) III and IV
c) I and IV
d) II and III

Section: 9.4, 9.5, 9.6
Difficulty Level: Hard
17. Which are the final reaction products (2), which are formed by the following sequence of reactions.? (HINT: assume an excess of K2Cr2O7 in step 2)

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a) I and II b) II and III c) II and IV d) I and IV

Section: 9.7
Difficulty Level: Medium
18. What is the major contributing structure to the cation intermediate of the bromination of anisole?

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a) I
b) II
c) III
d) IV

Section: 9.4, 9.5, 9.7
Difficulty Level: Hard
19. Which is the major product of the following reactions?

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a) para-chlorobenzoic acid b) meta-chlorobenzoic acid c) a mixture of para- and meta-chlorobenzoic acid d) a mixture of ortho- and para-chlorobenzoic acid

Section: 9.5 and 9.7
Difficulty Level: Hard
20. Which is the major product of the following reaction?

a) 1-chloro-4-nitrobenzene b) 1-chloro-3-nitrobenzene c) 1-chloro-2-nitrobenzene d) a mixture of 1-chloro-4-nitrobenzene and 1-chloro-2-nitrobenzene

Section: 9.5 and 9.7
Difficulty Level: Hard
21. Which is one possible product from the following consecutive reactions?

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a) I b) II c) III d) IV

Section: 9.6 and 9.7
Difficulty Level: Medium
22. Which is the best reaction sequence for preparing the following compound from benzene? (HINT: consider only the reaction product from electrophilic addition in the ortho position).

[pic] a) I b) II c) III d) IV

Section: 9.6 and 9.7
Difficulty Level: Medium
23. Which is the best reaction sequence for preparing the following compound from benzene?

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a) I b) II c) III d) IV

Section: 9.6 and 9.7
Difficulty Level: Medium
24. Which is the major product of the following reaction?

[pic]

[pic]

a) I
b) II
c) III
d) IV

Section: 9.6 and 9.7
Difficulty Level: Medium
25. Which is the product in the following reaction?

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a) I a) II b) III c) IV

Section: 9.8
Difficulty Level: Easy
26. Arrange the compounds in order of increasing acidity (least first).

a) I, II, III, IV b) III, II, IV, I c) I, IV, III, II d) II, III, IV, I

Section: 9.8
Difficulty Level: Medium
27. Arrange the compounds in order of increasing acidity (least first).

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a) I, II, III, IV b) III, IV, II, I c) I, II, IV, III d) II, I, III, IV

Section: 9.8
Difficulty Level: Medium
28. How can phenol be distinguished from cyclohexanol?

a) solubility in water b) solubility in aqueous hydrochloric acid solution c) solubility in aqueous sodium bicarbonate solution d) solubility in aqueous sodium hydroxide solution

Section: 9.9
Difficulty Level: Hard
29. Arrange the compounds in order of increasing acidity (least first).

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d) I, II, III, IV b) II, IV, I, III c) III, II, IV, I d) II, III, I, IV

Fill in the Blank Questions

Section: 9.4
Difficulty Level: Hard
1. The major product of the following reaction is,

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Section: 9.6
Difficulty Level: Medium
2. The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,

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Section: 9.5 and 9.7
Difficulty Level: Medium
3. The major products of the following reaction are?

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Section: 9.5, 9.6, 9.7
Difficulty Level: Medium
4. The reagent that completes the following reaction is

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Section: 9.5, 9.6, 9.7
Difficulty Level: Hard
5. The reagents that complete the following reactions are

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Section: 9.5, 9.6, 9.7
Difficulty Level: Hard
6. Your choice of starting material and reagent that complete the following reaction are?

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Section: 9.5, 9.6, 9.7
Difficulty Level: Hard
7. Your choice of starting material, intermediate and reagents that complete the following reaction are?

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Section: 9.5 and 9.7
Difficulty Level: Medium
8. The major product of the following reaction is
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Section: 9.8
Difficulty Level: Medium
9. The major products of the following reaction are

[pic]

Section: 9.8
Difficulty Level: Medium
10. The major products of the following reaction are

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True-False Questions

Section: 9.1
Difficulty Level: Easy
1. The name of the following structure is 2,4-diethylnitrobenzene.

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Section: 9.1
Difficulty Level: Easy
2. The name of the following structure is 3,5-dibromobenzoic acid.

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Section: 9.2
Difficulty Level: Easy
3. The following compound is aromatic.

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Section: 9.2
Difficulty Level: Medium
4. The following compound is aromatic

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Section: 9.4
Difficulty Level: Medium
5. The product of the reaction of isopropylbenzene with chromic acid is methylphenyl ketone.

Section: 9.4, 9.5, 9.7
Difficulty Level: Hard
6. The following reaction scheme will synthesize the product shown.

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Section: 9.5 and 9.7
Difficulty Level: Medium
7. The following reaction scheme will synthesize the product shown.

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Section: 9.6
Difficulty Level: Medium
8. The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic substitution.

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Section: 9.6
Difficulty Level: Medium
9. The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic substitution.

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Section: 9.5, 9.6, 9.7
Difficulty Level: Medium
10. The product of the reaction of toluene with concentrated nitric and sulfuric acid is m-nitrotoluene.

Section: 9.5, 9.6, 9.7
Difficulty Level: Medium
11. The product of the reaction of methyl benzoate and chlorine/AlCl3 is methyl 3-chlorobenzoate.

Answers

Multiple Choice

1. b
2. c
3. c
4. c
5. c
6. a
7. b
8. c
9. b
10. c
11. a
12. a
13. b
14. b
15. c
16. c
17. c
18. d
19. d
20. b
21. c
22. d
23. a
24. d
25. a
26. a
27. c
28. d
29. b

Fill in the Blank Questions

1.
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2.
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3.

4. HNO3, H2SO4

5.
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6.
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7.
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8.
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9.
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10.
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True-False Questions

1. T
2. T
3. F
4. T
5. F
6. F
7. T
8. T
9. F
10. F
11. T

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