Aromatic Compounds and Electrophilic Substitution - Numerical Applications
Q. In the nitration of toluene, which product is formed predominantly?
A.
Nitrotoluene (ortho)
B.
Nitrotoluene (para)
C.
Dinitrotoluene
D.
Benzyl nitrite
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Solution
The para-nitrotoluene is formed predominantly due to steric hindrance at the ortho position.
Correct Answer: B — Nitrotoluene (para)
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Q. In the nitration of toluene, which product is predominantly formed?
A.
Nitrotoluene
B.
Dinitrotoluene
C.
Benzyl alcohol
D.
Toluene sulfonic acid
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Solution
The predominant product is nitrotoluene, specifically ortho- and para-nitrotoluene due to the activating effect of the methyl group.
Correct Answer: A — Nitrotoluene
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Q. In the presence of a strong electrophile, which aromatic compound will undergo substitution the fastest?
A.
Benzene
B.
Phenol
C.
Aniline
D.
Toluene
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Solution
Aniline will undergo substitution the fastest due to the strong activating effect of the amino group, which donates electron density to the ring.
Correct Answer: C — Aniline
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Q. In the presence of sulfuric acid, what is the product of the electrophilic substitution of benzene with sulfur trioxide?
A.
Benzene sulfonic acid
B.
Benzene thiosulfate
C.
Benzene sulfide
D.
Benzene disulfide
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Solution
The product is benzene sulfonic acid, formed by the electrophilic substitution of sulfur trioxide on benzene.
Correct Answer: A — Benzene sulfonic acid
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Q. What is the expected product when phenol is treated with bromine water?
A.
Bromobenzene
B.
2,4,6-Tribromophenol
C.
Benzene
D.
Bromophenol
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Solution
The expected product is 2,4,6-tribromophenol, as phenol is highly reactive towards electrophilic substitution due to the hydroxyl group.
Correct Answer: B — 2,4,6-Tribromophenol
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Q. What is the IUPAC name of the compound formed when benzene undergoes sulfonation with sulfuric acid?
A.
Benzene sulfonic acid
B.
Benzene thiosulfate
C.
Benzene sulfate
D.
Benzene disulfide
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Solution
The product is benzene sulfonic acid, formed by the addition of a sulfonyl group to the benzene ring.
Correct Answer: A — Benzene sulfonic acid
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Q. Which of the following compounds is a stronger electrophile in electrophilic aromatic substitution?
A.
Benzene
B.
Nitrobenzene
C.
Toluene
D.
Chlorobenzene
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Solution
Toluene is a stronger electrophile due to the electron-donating effect of the methyl group.
Correct Answer: C — Toluene
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Q. Which of the following compounds is the most reactive towards electrophilic substitution?
A.
Benzene
B.
Toluene
C.
Chlorobenzene
D.
Nitrobenzene
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Solution
Toluene is the most reactive due to the electron-donating effect of the methyl group, which activates the ring towards electrophilic substitution.
Correct Answer: B — Toluene
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Q. Which of the following compounds will not undergo electrophilic substitution?
A.
Benzene
B.
Toluene
C.
Nitrobenzene
D.
Phenol
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Solution
Nitrobenzene will not undergo electrophilic substitution readily because the nitro group is a strong deactivator and meta-director.
Correct Answer: C — Nitrobenzene
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Q. Which of the following compounds will undergo electrophilic substitution the fastest?
A.
Benzene
B.
Ethylbenzene
C.
Chlorobenzene
D.
Nitrobenzene
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Solution
Ethylbenzene will undergo electrophilic substitution the fastest due to the electron-donating effect of the ethyl group.
Correct Answer: B — Ethylbenzene
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Q. Which position on a disubstituted benzene ring will a new substituent most likely attach if one substituent is a strong electron-donating group and the other is a weak electron-withdrawing group?
A.
Ortho
B.
Meta
C.
Para
D.
None
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Solution
The new substituent will most likely attach at the ortho position due to the activating effect of the electron-donating group.
Correct Answer: A — Ortho
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Q. Which position on the benzene ring does a nitro group preferentially substitute when starting from nitrobenzene?
A.
Ortho
B.
Meta
C.
Para
D.
All positions equally
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Solution
The nitro group is a deactivating and meta-directing group, so the substitution occurs predominantly at the meta position.
Correct Answer: B — Meta
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