Ch15 Reactions Of Aromatic Compounds Verified Test Bank - Organic Chemistry 13e | Test Bank by Solomons by Graham Solomons. DOCX document preview.
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
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.
Topic: Mechanisms and Intermediates
Section: 15.2
Difficulty Level: Medium
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
e) None of these choices.
Topic: Mechanisms and Intermediates
Section: 15.2
Difficulty Level: Medium
4) Which of the following structures contribute(s) to the resonance hybrid of the intermediate formed when bromobenzene undergoes para-chlorination?
a) I
b) II
c) III
d) IV
e) All of these choices.
Topic: Mechanisms and Intermediates
Section: 15.8
Difficulty Level: Medium
5) Which of the following structures contribute(s) to the resonance hybrid of the intermediate formed when chlorobenzene undergoes para-chlorination?
a) I
b) II
c) III
d) IV
e) All of these choices.
Topic: Mechanisms and Intermediates
Section: 15.8
Difficulty Level: Medium
6) Which of the following structures contribute(s) to the resonance hybrid of the intermediate formed when acetanilide undergoes para-bromination?
a) I
b) II
c) III
d) IV
e) All of these choices.
Topic: Mechanisms and Intermediates
Section: 15.8
Difficulty Level: Medium
7) Which of the following contributors to the resonance stabilized hybrid formed when aniline undergoes para-chlorination would be exceptionally stable?
a) I
b) II
c) III
d) IV
e) None of these choices.
Topic: Mechanisms and Intermediates
Section: 15.8
Difficulty Level: Medium
8) Consider the structures given below. Which of them would be a relatively stable contributor to the hybrid formed when toluene undergoes para bromination?
a) I
b) II
c) III
d) IV
e) V
Topic: Mechanisms and Intermediates
Section: 15.8
Difficulty Level: Medium
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.
Topic: Mechanisms and Intermediates
Section: 15.8
Difficulty Level: Medium
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?
a) I
b) II
c) III
d) IV
e) All contribute equally.
Topic: Mechanisms and Intermediates
Section: 15.8
Difficulty Level: Medium
11) Consider the resonance forms shown for the arenium ion formed from the bromination of acetanilide. Which resonance form contributes most to the overall resonance hybrid?
a) I
b) II
c) III
d) IV
e) All contribute equally.
Topic: Mechanisms and Intermediates
Section: 15.8
Difficulty Level: Medium
12) The electrophilic bromination or chlorination of benzene requires, in addition to the halogen:
a) a hydroxide ion.
b) a Lewis base.
c) a Lewis acid.
d) peroxide.
e) ultraviolet light.
Topic: Other EAS Considerations
Section: 15.3
Difficulty Level: Easy
13) In electrophilic aromatic substitution, the attacking species (the electrophile) necessarily is a:
a) neutral species.
b) positively charged species.
c) lewis acid.
d) proton.
e) carbocation.
Topic: Other EAS Considerations
Section: 15.2
Difficulty Level: Medium
14) Which of these liquids would be unsuitable as an inert solvent for a Friedel-Crafts reaction?
a) Chlorobenzene
b) Nitrobenzene
c) Acetophenone
d) (Trifluoromethyl) benzene
e) All of these choices could be used.
Topic: Other EAS Considerations
Section: 15.6
Difficulty Level: Medium
15) Undesired polysubstitution of an aromatic nucleus is most likely to be encountered in the case of:
a) Friedel-Crafts alkylation
b) Friedel-Crafts acylation
c) Nitration
d) Sulfonation
e) Chlorination
Topic: Other EAS Considerations
Section: 15.6
Difficulty Level: Medium
16) This substituent deactivates the benzene ring towards electrophilic substitution but directs the incoming group chiefly to the ortho and para positions.
a) -OCH2CH3
b) -NO2
c) -F
d) -CF3
e) -NHCOCH3
Topic: Other EAS Considerations
Section: 15.8 and 15.9
Difficulty Level: Medium
17) This molecule does not normally participate as a reactant in a Friedel-Crafts reaction.
a) Benzene
b) Chlorobenzene
c) Nitrobenzene
d) Toluene
e) tert-Butylbenzene
Topic: Other EAS Considerations
Section: 15.6
Difficulty Level: Medium
18) Which one of these molecules can be a reactant in a Friedel-Crafts reaction?
a) Aniline
b) Nitrobenzene
c) Chloroethene
d) Bromobenzene
e) p-Bromonitrobenzene
Topic: Other EAS Considerations
Section: 15.6
Difficulty Level: Medium
19) Which one of these molecules can be a reactant in a Friedel-Crafts reaction?
a) Aniline
b) Benzenesulfonic acid
c) Chloroethene
d) Bromobenzene
e) p-Bromonitrobenzene
Topic: Other EAS Considerations
Section: 15.6
Difficulty Level: Medium
20) Which reagent would you use as the basis for a simple chemical test that would distinguish between toluene and vinylbenzene (C6H5CH=CH2)?
a) NaOH/H2O
b) Br2
c) NaBH4
d) HCl/H2O
e) NaI in acetone
Topic: Functional Group Tests
Sections: 14.2, 14.3 and 15.3
Difficulty Level: Medium
21) Which reagent or test could you use to distinguish between phenylacetylene and vinylbenzene?
a) NaOH/H2O
b) Br2
c) IR Spectroscopy
d) CrO3/H2SO4
e) Concd. H2SO4
Topic: Nomenclature, Functional Group Tests
Section: 14.2, 14.11 and 15.3
Difficulty Level: Medium
22) What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and HF?
a) butylbenzene
b) 2-phenylbutane
c) 2-methyl-1-phenylpropane
d) t-butylbenzene
e) 2,2-diphenylbutane
Topic: Nomenclature, Reaction Products
Section: 14.2 and 15.6
Difficulty Level: Hard
23) What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and AlCl3?
a) butylbenzene
b) 2-phenylbutane
c) 2-methyl-1-phenylpropane
d) t-butylbenzene
e) 2,2-diphenylbutane
Topic: Nomenclature, Reaction Products
Section: 14.2 and 15.6
Difficulty Level: Hard
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?
a) 1-bromo-4-chlorobenzene
b) 1-bromo-2-chlorobenzene
c) 1-bromo-3-chlorobenzene
d) 4-bromoacetanilide
e) 3-bromoacetanilide
Topic: Nomenclature, Reaction Products
Section: 14.2, 15.3, and 15.6
Difficulty Level: Hard
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 reactions?
a) 1-bromo-4-chlorobenzene
b) 1-bromo-2-chlorobenzene
c) 1-bromo-3-chlorobenzene
d) 4-bromoanisole
e) 3-bromoanisole
Topic: Nomenclature, Reaction Products
Section: 14.2, 15.3, and 15.6
Difficulty Level: Hard
26) Which of the following reactions could be used to synthesize tert-butylbenzene?
a) 
b) 
c) 
d) All of these choices.
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
27) Which of the following reactions could be used to synthesize tert-butylbenzene?
a) 
b) 
c) 
d) All of these choices.
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
28) Which of the following reactions could be used to synthesize tert-butylbenzene?
a) 
b)
c) 
d) All of these choices.
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
29) Consider the following reaction: what is the expected product?
a) I
b) II
c) III
d) IV
e) V
Topic: Synthesis
Section: 15.3
Difficulty Level: Easy
30) Which of the following reactions would yield isopropylbenzene as the major product?
a) 
b) 
c) 
d) All of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
31) Which of the following reactions would yield isopropylbenzene as the major product?
a) 
b) 
c) 
d) 
e) All of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
32) Which of the following reactions would yield isopropylbenzene as the major product?
a)
b) 
c) 
d) 
e) All of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
33) Which of the following reactions would produce isopropylbenzene?
a) 
b) 
c) 
d) 
e) All of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
34) Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?
a) C6H5CH2CH3 + Cl2, Fe
b) C6H5CH2CH3 + Cl2, 400C
c) C6H5CH2CH2OH + SOCl2
d) C6H5CH=CH2 + HCl, peroxide
e) C6H6 + CH3CH2Cl, AlCl3
Topic: Synthesis
Sections: 11.9 and 15.6
Difficulty Level: Medium
35) Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?
a) C6H5CH2CH3 + Cl2, Fe
b) C6H5CH2CH3 + Cl2, 400C
c) C6H5CH2CH2OH + PCl5
d) C6H5CH=CH2 + HCl, peroxide
e) C6H6 + CH3CH2Cl, AlCl3
Topic: Synthesis
Sections: 11.9 and 15.6
Difficulty Level: Medium
36) Which of the following reactions would produce cumene?
a)
b)
c)
d)
e) All of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Hard
37) Which of the following reactions would yield cumene as the major product?
a) 
b) 
c) 
d) 
e) All of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Hard
38) Which of the following reactions would give the product(s) indicated in substantial amounts (i.e., in greater than 50% yield)?
a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Topic: Reaction Products
Section: 15.6
Difficulty Level: Easy
39) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6
Difficulty Level: Medium
40) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6
Difficulty Level: Medium
41) The major product(s) of the following reaction,
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6
Difficulty Level: Medium
42) What might be predicted to happen when the following substance undergoes Friedel-Crafts acylation?
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.
Topic: Reaction Products
Section: 15.6
Difficulty Level: Medium
43) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
44) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
45) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
46) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
47) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
48) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
49) Which would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
50) Which would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
51) Which would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
52) Which would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
53) Which would be the product, X, of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
54) Which would be the product, X, of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.7
Difficulty Level: Medium
55) The major product(s), D, of the following reaction,
would be:
a) I
b) II
c) III
d) IV
e) Approximately equal amounts of I and II.
Topic: Reaction Products
Section: 15.3 and 15.8
Difficulty Level: Medium
56) The major product, D, of the following reaction,
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.3 and 15.8
Difficulty Level: Medium
57) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) Equal amounts of II and IV.
Topic: Reaction Products
Section: 15.3 and 15.8
Difficulty Level: Medium
58) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) Equal amounts of II and IV.
Topic: Reaction Products
Section: 15.3 and 15.8
Difficulty Level: Medium
59) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.3 and 15.8
Difficulty Level: Medium
60) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.3 and 15.8
Difficulty Level: Medium
61) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.3 and 15.8
Difficulty Level: Medium
62) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.3 and 15.8
Difficulty Level: Medium
63) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.3 and 15.8
Difficulty Level: Medium
64) What would you expect to be the major product obtained from the monobromination of m-dichlorobenzene?
a) I
b) II
c) III
d) Equal amounts of I and II.
e) Equal amounts of I, II and III.
Topic: Reaction Products
Section: 15.3 and 15.8
Difficulty Level: Medium
65) Which would be the major product(s) of the following reaction?
a) I
b) II
c) III
d) I and II in roughly equal amounts.
e) I and III in roughly equal amounts.
Topic: Reaction Products
Section: 15.3 and 15.8
Difficulty Level: Medium
66) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Medium
67) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Medium
68) What would be the major product(s) of the following reaction?
a) I
b) II
c) III
d) IV
e) Approximately equal amounts of II and IV.
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Medium
69) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Medium
70) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Medium
71) What would you expect to be the major product(s) obtained from the mononitration of m-dichlorobenzene?
a) I
b) II
c) III
d) Equal amounts of I and II.
e) Equal amounts of I, II and III.
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Medium
72) What would you expect to be the major product(s) obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) Equal amounts of I and II.
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Medium
73) The major product(s), D, of the following reaction
would be:
a) I
b) II
c) III
d) IV
e) Equal amounts of I and II.
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Medium
74) Which would be the major product(s) of the following reaction?
a) I
b) II
c) III
d) I and II in roughly equal amounts.
e) I and III in roughly equal amounts.
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Medium
75) Which would be the major product(s) of the following reaction?
a) I
b) II
c) III
d) I and II in roughly equal amounts.
e) I and III in roughly equal amounts.
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Medium
76) What would be the major product(s) of the following reaction?
a) I
b) II
c) III
d) Equal amounts of I and IV.
e) Equal amounts of II and IV.
Topic: Reaction Products
Section: 15.5 and 15.8
Difficulty Level: Medium
77) What would be the major product(s) of the following reaction?
a) I
b) II
c) III
d) Equal amounts of I and IV.
e) Equal amounts of II and IV.
Topic: Reaction Products
Section: 15.5 and 15.8
Difficulty Level: Medium
78) The major product(s), C, of the following reaction,
would be:
a) I
b) II
c) III
d) Approximately equal amounts of I and II.
e) Approximately equal amounts of I and III.
Topic: Reaction Products
Section: 15.5 and 15.8
Difficulty Level: Medium
79) The major product(s), A, of the following reaction,
would be:
a) I
b) II
c) A mixture of I and II.
d) III
e) IV
Topic: Reaction Products
Section: 15.11
Difficulty Level: Medium
80) The major product(s) of the following reaction,
a) I
b) II
c) A mixture of I and II.
d) III
e) IV
Topic: Reaction Products
Section: 15.11
Difficulty Level: Medium
81) The major product(s) of the following reaction,
a) I
b) II
c) A mixture of I and II.
d) III
e) IV
Topic: Reaction Products
Section: 15.11
Difficulty Level: Medium
82) The major product(s), A, of the following reaction,
would be:
a) I
b) II
c) A mixture of I and II.
d) III
e) IV
Topic: Reaction Products
Section: 15.11
Difficulty Level: Medium
83) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.11
Difficulty Level: Medium
84) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.11
Difficulty Level: Medium
85) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.11
Difficulty Level: Medium
86) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.11
Difficulty Level: Medium
87) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.11
Difficulty Level: Medium
88) What would be the major product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.11
Difficulty Level: Medium
89) When toluene is reacted in turn with 1) Cl2 (large excess), heat, and light and 2) Br2,FeBr3, the chief product is:
a) I
b) II
c) III
d) IV
e) A mixture of III and IV.
Topic: Reaction Products
Section: 15.3 and 15.11
Difficulty Level: Medium
90) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Hard
91) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) A mixture of II and III.
Topic: Reaction Products
Section: 15.4 and 15.8
Difficulty Level: Hard
92) The reaction of benzene with (CH3)3CCH2Cl in the presence of anhydrous aluminum chloride produces principally which of these?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.6
Difficulty Level: Hard
93) The reaction of benzene with 
in the presence of anhydrous aluminum chloride produces principally which of these?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6 and 15.6
Difficulty Level: Hard
94) The reaction of benzene with 
in the presence of anhydrous aluminum chloride produces principally which of these?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6
Difficulty Level: Hard
95) The reaction of benzene with 
in the presence of anhydrous aluminum chloride produces principally which of these?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6
Difficulty Level: Hard
96) The reaction of benzene with 
in the presence of anhydrous aluminum chloride produces principally which of these?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6
Difficulty Level: Hard
97) Toluene is subjected to the action of the following reagents in the order given: (1) KMnO4,OH-, heat; then H3O+ (2) HNO3, H2SO4 (3) Br2, FeBr3
What is the final product of this sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.3, 15.4, 15.8, and 15.11
Difficulty Level: Hard
98) Toluene is subjected to the action of the following reagents in the order given: (1) KMnO4,OH-, heat; then H3O+ (2) HNO3, H2SO4 (3) Cl2, FeCl3
What is the final product of this sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.3, 15.4, 15.8, and 15.11
Difficulty Level: Hard
99) What product would result from the following series of reactions,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction products
Section: 15.6, 15.11
Difficulty Level: Hard
100) What product would result from the following series of reactions,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6, 15.11
Difficulty Level: Hard
101) What product would result from the following series of reactions,
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.6, 15.11
Difficulty Level: Hard
102) Which of the following is not a meta-directing substituent when present on the benzene ring?
a) -NHCOCH3
b) -NO2
c) -N(CH3)3+
d) -CN
e) -CO2H
Topic: Directing Effects
Section: 15.8
Difficulty Level: Easy
103) Which of the following is not a meta-directing substituent when present on the benzene ring?
a) -N=O
b) -NO2
c) -N(CH3)3+
d) -CN
e) -CO2H
Topic: Directing Effects
Section: 15.8
Difficulty Level: Easy
104) Each of the five disubstituted benzenes shown below is nitrated. In which of these cases does the arrow not indicate the chief position of nitration.
a) I
b) II
c) III
d) IV
e) V
Topic: Directing Effects
Section: 15.12
Difficulty Level: Easy
105) Which of the following compounds would yield the greatest amount of meta product when subjected to ring nitration?
a) I
b) II
c) III
d) IV
e) V
Topic: Directing Effects
Section: 15.8
Difficulty Level: Easy
106) Which of the following is not an ortho-para director in electrophilic aromatic substitution?
a) -CF3
b) -OCH3
c) -CH3
d) -F
e) -NH2
Topic: Directing Effects
Section: 15.8
Difficulty Level: Easy
107) Which of the following is not an ortho-para director in electrophilic aromatic substitution?
a) -CCl3
b) -OCH3
c) -CH3
d) -F
e) -NH2
Topic: Directing Effects
Section: 15.8
Difficulty Level: Easy
108) Which of the following is not an ortho-para director in electrophilic aromatic substitution?
a) -SO3H
b) -OCH3
c) -CH3
d) -F
e) -NH2
Topic: Directing Effects
Section: 15.8
Difficulty Level: Easy
109) Which of the following is not an ortho-para director in electrophilic aromatic substitution?
a) 
b) -OCH3
c) -CH3
d) -F
e) -NH2
Topic: Directing Effects
Section: 15.8
Difficulty Level: Easy
110) Which is the best prediction of the site(s) of substitution when 3-methylphenol is nitrated?
a) C-2
b) C-4
c) C-5
d) C-6
e) C-4 and C-6
Topic: Directing Effects
Section: 15.8
Difficulty Level: Easy
111) (Trifluoromethyl)benzene, C6H5CF3, will
a) nitrate rapidly in the ortho-para positions.
b) nitrate slowly in the ortho-para positions.
c) nitrate rapidly in the meta position.
d) nitrate slowly in the meta position.
e) fail to nitrate under any conditions.
Topic: Directing Effects
Section: 15.8
Difficulty Level: Easy
112) What feature is common to all meta-directing groups?
a) The atom directly attached to the ring has a full or well-developed partial positive charge.
b) The atom directly attached to the ring is doubly bonded to oxygen.
c) One or more halogen atoms are present in the group.
d) One or more oxygen atoms are present in the group.
e) The group is attached to the ring through a carbon atom.
Topic: Directing Effects
Section: 15.8 and 15.9
Difficulty Level: Easy
113) Which of these compounds gives essentially a single product on electrophilic substitution of a third group?
a) p-chlorotoluene
b) m-ethylanisole
c) 1-bromo-2-chlorobenzene
d) m-xylene
e) 3-hydroxybenzoic acid
Topic: Directing Effects
Section: 15.8
Difficulty Level: Medium
114) Arrange the following compounds in order of decreasing reactivity in electrophilic substitution:
a) V > II > I > III > IV
b) II > V > III > I > IV
c) IV > I > III > V > II
d) III > II > I > IV > V
e) IV > V > II > I > III
Topic: Directing Effects
Section: 15.8
Difficulty Level: Medium
115) What is a feature found in all ortho-para directing groups?
a) An oxygen atom is directly attached to the aromatic ring.
b) The atom attached to the aromatic ring must possess an unshared pair of electrons.
c) The group has the ability to delocalize the positive charge of the arenium ion.
d) The atom directly attached to the aromatic ring is more electronegative than carbon.
e) The group contains a multiple bond.
Topic: Directing Effects
Section: 15.9
Difficulty Level: Medium
116) The ortho/para product ratio is expected to be the smallest for the bromination of which of these?
a) Toluene
b) Isopropylbenzene
c) Butylbenzene
d) sec-Butylbenzene
e) tert-Butylbenzene
Topic: Directing Effects
Section: 15.8 and 15.13
Difficulty Level: Medium
117) Which reagent(s) would you use to carry out the following transformation?
isopropylbenzene 2- and 4-chloro-1-isopropylbenzene
a) Cl2, light, and heat
b) Cl2, FeCl3
c) SOCl2
d) C2H5Cl, AlCl3
e) HCl, peroxides
Topic: Reagents
Section: 15.3 and 15.8
Difficulty Level: Medium
118) Which reagent(s) would you use to carry out the following transformation?
ethylbenzene 2- and 4-chloro-1-ethylbenzene
a) Cl2, light, and heat
b) Cl2, FeCl3
c) SOCl2
d) C2H5Cl, AlCl3
e) None of these choices.
Topic: Reagents
Section: 15.3 and 15.8
Difficulty Level: Medium
119) Which reagent(s) would you use to carry out the following transformation?
t-butylbenzene p-chloro substitution product
a) Cl2, light, and heat
b) Cl2, FeCl3
c) SOCl2
d) C2H5Cl, AlCl3
e) HCl, peroxide
Topic: Reagents
Section: 15.3 and 15.8
Difficulty Level: Medium
120) Which reagent(s) would you use to carry out the following transformation?
ethylbenzene 1-chloro-1-phenylethane
a) Cl2, light, or heat
b) Cl2, FeCl3
c) SOCl2
d) C2H5Cl, AlCl3
e) HCl, O2
Topic: Reagents
Section: 15.11
Difficulty Level: Medium
121) Which reagent(s) would you use to synthesize 2- and 4-bromo-1-cyclopentylbenzene from cyclopentylbenzene?
a) N-Bromosuccinimide (NBS), CCl4, light
b) PBr3
c) Br2, FeBr3
d) CH3CH2Br, AlBr3
e) HBr, ROOR
Topic: Reagents
Section: 15.3 and 15.8
Difficulty Level: Medium
122) Which reagent would you use to carry out the following transformation?
tert-butylbenzene p-tert-butylbenzenesulfonic acid
+
o-tert-butylbenzenesulfonic acid
a) HNO3/H2SO4
b) tert-C4H9Cl/AlCl3
c) H2SO3/peroxides
d) SO3/H2SO4
e) SO2/H2SO3
Topic: Reagents
Section: 15.5 and 15.8
Difficulty Level: Medium
123) Which reagent(s) would you use to carry out the following transformation?
toluene benzoic acid
a) Br2, heat, and light
b) Cl2, FeCl3
c) KMnO4, OH-, heat (then H3O+)
d) HNO3/H2SO4
e) SO3/H2SO4
Topic: Reagents
Section: 15.11
Difficulty Level: Medium
124) Which reagent(s) would you use to carry out the following transformation?
ethylbenzene benzoic acid
a) Cl2, light, and heat
b) Cl2, FeCl3
c) KMnO4, OH-, heat (then H3O+)
d) HNO3/H2SO4
e) SO3/H2SO4
Topic: Reagents
Section: 15.11
Difficulty Level: Medium
125) Which reagent(s) would you use to carry out the following transformation?
cumene 2- and 4-chlorocumene
a) Cl2, light, and heat
b) Cl2, FeCl3
c) SOCl2
d) C2H5Cl, AlCl3
e) HCl, peroxides
Topic: Reagents
Section: 15.3 and 15.8
Difficulty Level: Hard
126) Which reagent(s) would you use to carry out the following transformation?
toluene benzyl bromide
a) Br2, FeBr3
b) N-Bromosuccinimide, ROOR, h
c) HBr
d) Br2
e) NaBr, H2SO4
Topic: Reagents
Section: 15.11
Difficulty Level: Hard
127) The compound 4-bromo-1-propylbenzene is best made from benzene by the application of these reagents in the order shown:
a) (1) Br2,Fe (2) CH3CH2CH2Cl, AlCl3
b) (1) CH3CH2CH2Cl, AlCl3 (2) Br2,Fe
c) 
d) 
e) (1) (CH3)2CHCl, AlCl3 (2) Br2,Fe
Topic: Reagents
Section: 15.12
Difficulty Level: Hard
128) The compound 4-bromo-1-propylbenzene is best made from benzene by the application of these reagents in the order shown:
a) (1) Br2,Fe (2) CH3CH2CH2Cl, AlCl3
b) (1) CH3CH2CH2Cl, AlCl3 (2) Br2,Fe
c) 
d) 
e) (1) (CH3)2CHCl, AlCl3 (2) Br2,Fe
Topic: Reagents
Section: 15.12
Difficulty Level: Hard
129) Which of the following compounds would be most reactive toward electrophilic substitution?
a) I
b) II
c) III
d) IV
e) V
Topic: Relative Reactivities
Section: 15.9
Difficulty Level: Easy
130) Which of the following compounds would be least reactive toward electrophilic substitution?
a) I
b) II
c) III
d) IV
e) V
Topic: Relative Reactivities
Section: 15.9
Difficulty Level: Easy
131) Which of the following compounds would be most reactive to ring bromination?
a) I
b) II
c) III
d) IV
e) V
Topic: Relative Reactivities
Section: 15.9
Difficulty Level: Easy
132) Which of the following compounds would be least reactive toward electrophilic substitution?
a) I
b) II
c) III
d) IV
e) V
Topic: Relative Reactivities
Section: 15.9
Difficulty Level: Easy
133) Which of the following compounds would be most reactive toward electrophilic substitution?
a) I
b) II
c) III
d) IV
e) V
Topic: Relative Reactivities
Section: 15.9
Difficulty Level: Easy
134) Which of the following compounds would be most reactive toward ring nitration?
a) I
b) II
c) III
d) IV
e) V
Topic: Relative Reactivities
Section: 15.9
Difficulty Level: Easy
135) Which of the compounds listed below would you expect to give the greatest amount of meta-product when subjected to ring bromination?
a) I
b) II
c) III
d) IV
e) V
Topic: Relative Reactivities
Section: 15.9
Difficulty Level: Easy
136) Which of the following compounds would be most reactive toward ring bromination?
a) I
b) II
c) III
d) IV
e) V
Topic: Relative Reactivities
Section: 15.9
Difficulty Level: Easy
137) Which of the compounds listed below would you expect to give the greatest amount of meta-product when subjected to ring nitration?
a) I
b) II
c) III
d) IV
e) V
Topic: Relative Reactivities
Section: 15.9
Difficulty Level: Easy
138) Which of the following compounds would you expect to be most reactive toward ring nitration?
a) Benzene
b) Toluene
c) m-Xylene
d) p-Xylene
e) Benzoic acid
Topic: Relative Reactivities
Section: 15.9
Difficulty Level: Medium
139) Which of the following compounds would you expect to be most reactive toward ring nitration?
a) Benzene
b) Toluene
c) m-Xylene
d) o-Xylene
e) Benzoic acid
Topic: Relative Reactivities
Section: 15.9
Difficulty Level: Medium
140.)Which of the following structures would not be a contributor to the resonance hybrid of the benzyl cation?
a) I
b) II
c) III
d) IV
e) V
Topic: Non-EAS Relative Rates and Intermediates
Section: 15.11
Difficulty Level: Medium
141) Which of the following carbocations would be most stable?
a) 
b) 
c) 
d) 
e) 
Topic: Non-EAS Relative Rates and Intermediates
Section: 15.11
Difficulty Level: Medium
142) Which alkyl halide would be most reactive in an SN2 reaction?
a) C6H5CH2CH2CH2Br
b) 
c) 
d) 
e) 
Topic: Non-EAS Relative Rates and Intermediates
Section: 15.13
Difficulty Level: Medium
143) Which alkyl halide would be most reactive in an SN1 reaction?
a) C6H5CH2CH2CH2Br
b) 
c) 
d) 
e) 
Topic: Non-EAS Relative Rates and Intermediates
Section: 15.13
Difficulty Level: Medium
144) The rate of solvolysis in ethanol is least for which of these compounds?
a) C6H5CH2Cl
b) 
c) (C6H5)2CHCl
d) 
e) (C6H5)3CCl
Topic: Non-EAS Relative Rates and Intermediates
Section: 15.13
Difficulty Level: Medium
145) Which of these species is/are proposed as intermediate(s) in the mechanism for the Birch reduction?
a) Radical
b) Carbanion
c) Radical anion
d) Both A) and B)
e) All of A), B) and C)
Topic: Non-EAS Relative Rates and Intermediates
Section: 15.15
Difficulty Level: Hard
146) Benzoic acid can be prepared by the oxidation of all of the following compounds except this one:
a) C6H5CH=CH2
b) C6H5CCH
c) C6H5COCH3
d) C6H5CH2CH2CH3
e) C6H5C(CH3)3
Topic: Synthesis
Section: 15.11
Difficulty Level: Easy
147) Benzoic acid can be prepared by the oxidation of which of the following compounds:
a) C6H5CH=CH2
b) C6H5CCH
c) C6H5COCH3
d) C6H5CH2CH2CH3
e) All of these choices.
Topic: Synthesis
Section: 15.11
Difficulty Level: Easy
148) Benzoic acid can be prepared by the oxidation of which of the following compounds:
a) C6H5CH=CH2
b) C6H5CCH
c) C6H5COCH3
d) C6H5CH(CH3)2
e) All of these choices.
Topic: Synthesis
Section: 15.11
Difficulty Level: Easy
149) Which of these is a satisfactory synthesis of 1-bromo-2-phenylethane?
a) C6H5CH2CH3 + Br2, Fe3+
b) C6H5CH2CH3 + Br2, 400C
c) C6H5CH2CH2OH + Br2, CCl4
d) C6H5CH=CH2 + HBr, ROOR
e) C6H5CH2CH3 + NBS, ROOR
Topic: Synthesis
Section: 15.11
Difficulty Level: Medium
150) What reagent can effect the following transformation?
a) CO2; then H3O+
b) H3O+, heat
c) Mg; then CO2; then H3O+
d) H2O2, heat
e) KMnO4, OH-, heat; then H3O+
Topic: Synthesis
Section: 15.11
Difficulty Level: Medium
151) A good synthesis of
would be:
a) 
b) 
c) 
d) More than one of these choices.
e) None of these choices.
Topic: Synthesis
Section: 15.12
Difficulty Level: Medium
152) Which would be a good synthesis of m-nitrobenzoic acid?
a) 
b) 
c) 
d) More than one of these choices.
e) None of these choices.
Topic: Synthesis
Section: 15.12
Difficulty Level: Medium
153) Which of the following would be the best synthesis of 1,4-dimethyl-2-nitrobenzene?
a) 
b) 
c) 
d) 
e) All of these choices are equally good.
Topic: Nomenclature, Synthesis
Section: 15.12
Difficulty Level: Hard
154) Starting with benzene, the best method for preparing p-nitrobenzoic acid is:
a) HNO3/H2SO4; then CH3Cl/AlCl3; then separation of isomers; then KMnO4/
-OH/heat, followed by H3O+.
b) CH3Cl/AlCl3; then HNO3/H2SO4; then separation of isomers; then KMnO4/
-OH/heat, followed by H3O+.
c) CH3Cl/AlCl3; then KMnO4/-OH/heat, followed by H3O+; then HNO3/H2SO4.
d) HNO3/H2SO4; then KMnO4/-OH/heat, followed by H3O+; then CH3Cl/AlCl3.
e) HNO3/H2SO4; then CO2, followed by H3O+.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
155) Starting with benzene, the best method for preparing m-nitrobenzoic acid is:
a) HNO3/H2SO4; then CH3Cl/AlCl3; then separation of isomers; then KMnO4/
-OH/heat, followed by H3O+.
b) CH3Cl/AlCl3; then HNO3/H2SO4; then separation of isomers; then KMnO4/
-OH/heat, followed by H3O+.
c) CH3Cl/AlCl3; then KMnO4/-OH/heat, followed by H3O+; then HNO3/H2SO4.
d) HNO3/H2SO4; then KMnO4/-OH/heat, followed by H3O+; then CH3Cl/AlCl3.
e) HNO3/H2SO4; then CO2, followed by H3O+.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
156) How might the following synthesis be carried out:
a) 
b) 
c) 
d) 
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
157) How might the following synthesis be carried out:
a) 
b) 
c) 
d) 
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
158) How might the following synthesis be carried out:
a) 
b) 
c) 
d) 
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
159) How might the following synthesis be carried out:
a) 
b) 
c) 
d) 
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
160) How might the following synthesis be carried out:
a) 
b) 
c)
d)
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
161) Which is the best sequence of reactions for the preparation of p-bromostyrene from ethylbenzene?
a) 
b) 
c) 
d) 
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
162) Which is the best sequence of reactions for the following transformation?
a) i) HNO3, H2SO4; ii) CH3MgBr, Et2O; iii) H3O+, heat
b) i) CH3MgBr, Et2O; ii) H3O+, heat; iii) HNO3, H2SO4
c) i) HNO3, H2SO4; ii) NaBH4, H2O; iii) H3O+, heat
d) i) HNO3, H2SO4; ii) LiAlH4, H2O; iii) H3O+, heat
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
163) Which is the best sequence of reactions for the following transformation?
a) i) HNO3, H2SO4; ii) CH3MgBr, Et2O; iii) H2O, NH4Cl
b) i) CH3MgBr, Et2O; ii) H3O+, heat; iii) HNO3, H2SO4
c) i) HNO3, H2SO4; ii) NaBH4, H2O; iii) H3O+, heat
d) i) HNO3, H2SO4; ii) LiAlH4, H2O; iii) H3O+, heat
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
164) Which is the best sequence of reactions for the following transformation?
a) i) HNO3, H2SO4; ii) CH3MgBr, Et2O; iii) H2O, NH4Cl
b) i) CH3MgBr, Et2O; ii) H3O+, heat; iii) HNO3, H2SO4
c) i) HNO3, H2SO4; ii) NaBH4, H2O; iii) H3O+, heat
d) i) HNO3, H2SO4; ii) LiAlH4, H2O; iii) H3O+, heat
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
165) Which is the best sequence of reactions for the following transformation?
a) i) HNO3, H2SO4; ii) CH3MgBr, Et2O; iii) H3O+, heat
b) i) CH3MgBr, Et2O; ii) H3O+, heat; iii) HNO3, H2SO4
c) i) HNO3, H2SO4; ii) NaBH4, H2O; iii) H3O+, heat
d) i)HNO3, H2SO4; ii) LiAlH4, H2O; iii) H3O+, heat
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
166) Which is the best sequence of reactions for the following transformation?
a) i) HNO3, H2SO4; ii) 2EtMgBr, Et2O; iii) NH4Cl
b) i) 2EtMgBr, Et2O; ii) H3O+; iii) HNO3, H2SO4
c) i) HNO3, H2SO4; ii) NaBH4, H2O; iii) 2EtMgBr, Et2O
d) i) LAH; ii) 2EtLi, Et2O; iii) HNO3, H2SO4, heat
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
167) Which is the best sequence of reactions for the following transformation?
a) i) HNO3, H2SO4; ii) 2EtMgBr, Et2O; iii) NH4Cl
b) i) 2EtMgBr, Et2O; ii) H3O+; iii) HNO3, H2SO4
c) i) HNO3, H2SO4; ii) NaBH4, H2O; iii) 2EtMgBr, Et2O
d) i) LAH; ii) 2EtLi, Et2O; iii) HNO3, H2SO4, heat
e) None of these syntheses is satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
168) Which is the best sequence of reactions for the following transformation?
a) i) SOCl2; ii) C6H6, AlCl3; iii) Zn(Hg),HCl; iv) HNO3, H2SO4
b) i) SOCl2; ii) HNO3, H2SO4; iii) C6H6, AlCl3; iv) H2, Ni
c) i) HNO3, H2SO4; ii) SOCl2; iii) C6H6, AlCl3; iv) Zn(Hg),HCl
d) i) PBr3; ii) HNO3, H2SO4; iii) C6H6, AlCl3; iv) NaBH4, H2O
e) Two of these syntheses are satisfactory.
Topic: Synthesis
Section: 15.12
Difficulty Level: Hard
169) What is the Birch reduction product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Topic: Non-EAS Reactions
Section: 15.15
Difficulty Level: Medium
170) The major product(s), A, of the following reaction,
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Non-EAS Reactions
Section: 15.15
Difficulty Level: Medium
171) The major product(s), A, of the following reaction,
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Non-EAS Reactions
Section: 15.15
Difficulty Level: Medium
172) The major product(s) of the following reaction,
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Non-EAS Reactions
Section: 15.15
Difficulty Level: Medium
173) The major product(s) of the following reaction,
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Non-EAS Reactions
Section: 15.13
Difficulty Level: Medium
174) SN1 solvolysis of C6H5CH=CHCH2Cl in water produces:
a) C6H5CH2C(OH)=CH2
b) C6H5CH=CHCH2OH
c) C6H5CHOHCH=CH2
d) A mixture of B) and C)
e) A mixture of A), B) and C)
Topic: Non-EAS Reactions
Section: 15.13
Difficulty Level: Medium
175) Which compound is capable of undergoing both SN1 and SN2 reactions in ordinary nonacidic solvents?
a) I
b) II
c) III
d) IV
e) V
Topic: Non-EAS Reactions
Section: 15.13
Difficulty Level: Medium
176) Which alkyl halide can undergo both SN1 and SN2 reactions in nonacidic solvents?
a) CH3Br
b) CH3CH2CH2Br
c) 
d) C6H5CH2CH2CH2Br
e) 
Topic: Non-EAS Reactions
Section: 15.13
Difficulty Level: Medium
Question type: fill-in-the-blank
177) In general, there are three steps to an electrophilic aromatic substitution reaction. These are:
a) formation of an ___;
b) reaction with an aromatic ring to form an ___; and
c) loss of a ___ to reform the aromatic system.
Topic: EAS Mechanism
Section: 15.2
Difficulty Level: Easy
Question type: Molecular Drawing
178) Draw a mechanism that explains the formation of the following product in this Friedel-Crafts alkylation:
Topic: Mechanism, Carbocation Stability
Section: 15.6
Difficulty Level: Hard
Question type: fill-in-the-blank
179) When two different groups are present on a benzene ring, the ___ generally determines the outcome of an EAS reaction.
Topic: General EAS Reactivity
Section: 15.12
Difficulty Level: Easy
180) Substituent groups affect both ___ and ___ in electrophilic aromatic substitution reactions.
Topic: General EAS Reactivity
Section: 15.8
Difficulty Level: Easy
181) Electron-donating groups increase the electron density on the aromatic ring, causing it to be more reactive than benzene itself towards EAS. These types of groups are called ___ groups.
Topic: General EAS Reactivity
Section: 15.8
Difficulty Level: Easy
182) Electron-withdrawing groups decrease the electron density on the aromatic ring, causing it to be less reactive than benzene itself towards EAS. These types of groups are called ___ groups.
Topic: General EAS Reactivity
Section: 15.8
Difficulty Level: Easy
183) With the exception of halogens, activating groups are ___ directors and deactivating groups are ___ directors.
Topic: General EAS Reactivity
Section: 15.8
Difficulty Level: Easy
Question type: Essay
184) When the following substance is treated with Br2/FeBr3, the major product is obtained in good yield, and only very small amounts of minor products are found. What is this major product and why are the minor products not formed to any significant degree? Explain clearly.
Topic: General EAS Reactivity
Section: 15.3, 15.8 and 15.9
Difficulty Level: Medium
185) Based on your knowledge of electrophilic aromatic substitution, predict the preferential position of attack of an electrophile on furan, i.e., does the electrophile E+ attack carbon 2, or 3? Explain your answer.
Which substitution product forms preferentially and why?
Topic: General EAS Reactivity
Section: 15.2 and 15.9
Difficulty Level: Hard
186) Based on your knowledge of electrophilic aromatic substitution, predict the preferential position of attack of an electrophile on pyrrole, i.e., does the electrophile E+ attack carbon 2, or 3? Explain your answer.
Which substitution product forms preferentially and why?
Topic: General EAS Reactivity
Section: 15.2 and 15.9
Difficulty Level: Hard
187) Based on your knowledge of electrophilic aromatic substitution, predict the preferential position of attack of an electrophile on thiophene, i.e., does the electrophile E+ attack carbon 2, or 3? Explain your answer.
Which substitution product forms preferentially and why?
Topic: General EAS Reactivity
Section: 15.2 and 15.9
Difficulty Level: Hard
188) Based on your knowledge of electrophilic aromatic substitution, predict the position of attack of an electrophile on pyridine, i.e., does the electrophile E+ attack carbon 2, 3, or 4? Explain your answer.
Which substitution product(s) forms and why?
Topic: General EAS Reactivity
Section: 15.2 and 15.9
Difficulty Level: Hard
189) Based on your knowledge of electrophilic aromatic substitution, predict the preferential position of nitration of naphthalene, i.e., does the NO2+ attack carbon 1, or 2? Explain your answer.
Which substitution product forms preferentially and why?
Topic: General EAS Reactivity
Section: 15.2 and 15.9
Difficulty Level: Hard
190) Using a potential energy diagram, explain/illustrate the preferential formation of the 3 substituted product instead of the 2 or 4 product in the electrophilic aromatic substitution of pyridine.
P.E.
Reaction Progress
‡
‡
Ea
Ea
Topic: General EAS Reactivity, Mechanisms, Energy Diagrams
Section: 15.2 and 15.9
Difficulty Level: Hard
191) Using a potential energy diagram, explain/illustrate the preferential formation of the 1 nitrated product instead of the 2 nitrated product in the electrophilic aromatic nitration of naphthalene.
Topic: General EAS Reactivity, Mechanisms, Energy Diagrams
Section: 15.2 and 15.9
Difficulty Level: Hard
192) Using a potential energy diagram, explain/illustrate the preferential formation of the 2 substituted product instead of the 3 product in the electrophilic aromatic substitution of furan.
Topic: General EAS Reactivity, Mechanisms, Energy Diagrams
Section: 15.2 and 15.9
Difficulty Level: Hard
193) Using a potential energy diagram, explain/illustrate the preferential formation of the 2 substituted product instead of the 3 product in the electrophilic aromatic substitution of pyrrole.
Topic: General EAS Reactivity, Mechanisms, Energy Diagrams
Section: 15.2 and 15.9
Difficulty Level: Hard
194) Using a potential energy diagram, explain/illustrate the preferential formation of the 2 substituted product instead of the 3 product in the electrophilic aromatic substitution of thiophene.
Topic: General EAS Reactivity, Mechanisms, Energy Diagrams
Section: 15.2 and 15.9
Difficulty Level: Hard
195) Based on your knowledge of electrophilic aromatic substitution, and assuming the pyrrole ring of indole (shown) is activated toward electrophilic aromatic substituted more so than the benzenoid ring, predict the preferential position of attack of an electrophile, i.e., does the electrophile E+ attack carbon 2, or 3? Explain your answer.
Which substitution product forms preferentially and why?
Topic: General EAS Reactivity, Mechanisms, Energy Diagrams
Section: 15.2 and 15.9
Difficulty Level: Hard
196) Based on your knowledge of electrophilic aromatic substitution, and assuming the furan ring of benzo[b]furan (shown) is activated toward electrophilic aromatic substituted more so than the benzenoid ring, predict the preferential position of attack of an electrophile, i.e., does the electrophile E+ attack carbon 2, or 3? Explain your answer.
Which substitution product forms preferentially and why?
Topic: General EAS Reactivity, Mechanisms, Energy Diagrams
Section: 15.2 and 15.9
Difficulty Level: Hard
197) Based on your knowledge of electrophilic aromatic substitution, and assuming the thiophene ring of benzo[b]thiophene (shown) is activated toward electrophilic aromatic substituted more so than the benzenoid ring, predict the preferential position of attack of an electrophile, i.e., does the electrophile E+ attack carbon 2, or 3? Explain your answer.
Which substitution product forms preferentially and why?
Topic: General EAS Reactivity, Mechanisms, Energy Diagrams
Section: 15.2 and 15.9
Difficulty Level: Hard
198) Using a potential energy diagram, explain/illustrate the preferential formation of the 3 substituted product instead of the 2 product in the electrophilic aromatic substitution of benzo[b] thiophene (shown).
P.E.
Reaction Progress
‡
‡
Ea
Ea
Topic: General EAS Reactivity, Mechanisms, Energy Diagrams
Section: 15.2 and 15.9
Difficulty Level: Hard
199) Using a potential energy diagram, explain/illustrate the preferential formation of the 3 substituted product instead of the 2 product in the electrophilic aromatic substitution of benzo[b] furane (shown).
P.E.
Reaction Progress
‡
‡
Ea
Ea
Topic: General EAS Reactivity, Mechanisms, Energy Diagrams
Section: 15.2 and 15.9
Difficulty Level: Hard
200) Using a potential energy diagram, explain/illustrate the preferential formation of the 3 substituted product instead of the 2 product in the electrophilic aromatic substitution of indole (shown).
P.E.
Reaction Progress
‡
‡
Ea
Ea
Topic: General EAS Reactivity, Mechanisms, Energy Diagrams
Section: 15.2 and 15.9
Difficulty Level: Hard
201) Acid-catalyzed hydration of 1-phenyl-1-pentene gives 1-phenyl-1-pentanol almost exclusively; the other possible hydration product, 1-phenyl-2-pentanol, is not detected at all. Explain clearly.
Topic: Mechanism, Carbocation Stability
Section: 15.11
Difficulty Level: Hard
202) When toluene reacts with Cl2, the identity of the major product(s) obtained depends on whether the reaction is carried out in the presence of catalytic amounts of FeCl3, or without catalyst, at high temp. Explain clearly.
Topic: EAS/non-EAS Reactivity
Section: 15.3 and 15.11
Difficulty Level: Medium
203) Suggest a reasonable synthetic strategy for the synthesis of 3,5-dinitrobenzyl alcohol from benzaldehyde.
Topic: Synthetic Strategy
Section: 15.12
Difficulty Level: Medium
204) Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1-phenyl-1-pentanol from 4-methylpentanoyl chloride, (CH3)2CHCH2CH2COCl
Topic: Synthetic Strategy
Section: 15.6
Difficulty Level: Medium
205) Suggest a reasonable synthetic strategy for the synthesis of 6-methyl-3-phenyl-3-heptanol from 4-methylpentanoyl chloride, (CH3)2CHCH2CH2COCl
Topic: Synthetic Strategy
Section: 15.12
Difficulty Level: Hard
206) What product would result from the following series of reactions,
Topic: Synthetic Strategy
Section: 15.12
Difficulty Level: Hard
207) Propose a reasonable synthesis of the following compound from benzene.
Topic: Synthetic Strategy
Section: 15.12
Difficulty Level: Hard
208) What product would result from the following series of reactions:
Topic: Synthetic Strategy
Section: 15.12
Difficulty Level: Hard
209) What is the reactant in the Friedel-Crafts alkylation of benzene in HF to produce 2-phenylbutane?
a) cis-2-butene
b) 1-butene
c) isobutylene
d) trans-2-butene
e) n-butane
Topic: Nomenclature, Reaction Products
Section: 14.2 and 15.6
Difficulty Level: Hard
210) What is the reactant in the Friedel-Crafts alkylation of benzene in H2SO4 to produce 2-phenylbutane?
a) cis-2-butene
b) n-butane
c) trans-2-butene
d) 1-butene
e) isobutylene
Topic: Nomenclature, Reaction Products
Section: 14.2 and 15.6
Difficulty Level: Hard
211) What is the product of the following reaction?
a) n-butylbenzene
b) 1-methyl-2-propylbenzene
c) 1-methyl-3-propylbenzene
d) tert-butylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
212) What is the product of the following reaction?
a) n-butylbenzene
b) 1-methyl-2-isopropylbenzene
c) 1-methyl-3-isopropylbenzene
d) tert-butylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
213) What is the product of the following reaction?
a) n-butylbenzene
b) 1-methyl-2-propylbenzene
c) 1-methyl-3-propylbenzene
d) tert-butylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
214) What is the product of the following reaction?
a) n-butylbenzene
b) 1-methyl-2-isopropylbenzene
c) 1-methyl-3-isopropylbenzene
d) tert-butylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
215) What is the product of the following reaction?
a) n-butylbenzene
b) 1-methyl-2-isopropylbenzene
c) 1-methyl-3-isopropylbenzene
d) tert-butylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
216) What is the product of the following reaction?
a) n-butylbenzene
b) 1-methyl-2-isopropylbenzene
c) 1-methyl-3-isopropylbenzene
d) tert-butylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
217) What is the product of the following reaction?
a) n-butylbenzene
b) 1-methyl-2-isopropylbenzene
c) 1-methyl-3-isopropylbenzene
d) tert-butylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
218) What is the product of the following reaction?
a) n-butylbenzene
b) 1-methyl-2-isopropylbenzene
c) 1-methyl-3-isopropylbenzene
d) tert-butylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
219) What is the product of the following reaction?
a) n-butylbenzene
b) 1-methyl-2-isopropylbenzene
c) 1-methyl-3-isopropylbenzene
d) tert-butylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy
220) Consider the following reaction: what is the starting material?
a) p-chloroaniline
b) p-chloroanisole
c) 2,6-dibromoaniline
d) 2,4-dribromo-4-chloroacetanilide
e) 1,3-dribromo-5-chlorobenzene
Topic: Synthesis
Section: 15.3
Difficulty Level: Easy
221) What is the product of the following reaction?
a) n-propylbenzene
b) 1-methyl-2-ethylbenzene
c) 1-methyl-3-ethylbenzene
d) iso-propylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
222) What is the product of the following reaction?
a) iso-propylbenzene
b) n-propylbenzene
c) 1-methyl-2-ethylbenzene
d) 1-methyl-3-ethylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
223) What is the product of the following reaction?
a) iso-propylbenzene
b) n-propylbenzene
c) 1-methyl-2-ethylbenzene
d) 1-methyl-3-ethylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
224) What is the product of the following reaction?
a) iso-propylbenzene
b) n-propylbenzene
c) 1-methyl-2-ethylbenzene
d) 1-methyl-3-ethylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
225) What is the product of the following reaction?
a) iso-propylbenzene
b) n-propylbenzene
c) 1-methyl-2-ethylbenzene
d) 1-methyl-3-ethylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
226) What is the product of the following reaction?
a) iso-propylbenzene
b) n-propylbenzene
c) 1-methyl-2-ethylbenzene
d) 1-methyl-3-ethylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
227) What is the product of the following reaction?
a) iso-propylbenzene
b) n-propylbenzene
c) 1-methyl-2-ethylbenzene
d) 1-methyl-3-ethylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
228) What is the product of the following reaction?
a) iso-propylbenzene
b) n-propylbenzene
c) 1-methyl-2-ethylbenzene
d) 1-methyl-3-ethylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
229) What is the product of the following reaction?
a) iso-propylbenzene
b) n-propylbenzene
c) 1-methyl-2-ethylbenzene
d) 1-methyl-3-ethylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
230) What is the product of the following reaction?
a) iso-propylbenzene
b) n-propylbenzene
c) 1-methyl-2-ethylbenzene
d) 1-methyl-3-ethylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium
231) What is the product of the following reaction?
a) iso-propylbenzene
b) n-propylbenzene
c) 1-methyl-2-ethylbenzene
d) 1-methyl-3-ethylbenzene
e) None of these choices.
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium