Aromatic Compounds and Electrophilic Substitution - Higher Difficulty Problems
Q. In the nitration of benzene, what is the role of sulfuric acid?
A.
Nucleophile
B.
Electrophile
C.
Catalyst
D.
Solvent
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Solution
Sulfuric acid acts as a catalyst in the generation of the nitronium ion (NO2+), the active electrophile in the nitration reaction.
Correct Answer: C — Catalyst
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Q. In the presence of a strong electrophile, which position on a disubstituted benzene ring will a third substituent most likely attach?
A.
Ortho
B.
Meta
C.
Para
D.
Random
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Solution
The position of the third substituent depends on the nature of the existing substituents; however, ortho and para positions are generally favored for activating groups.
Correct Answer: A — Ortho
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Q. What is the effect of a strong electron-donating group on the rate of electrophilic aromatic substitution?
A.
Decreases the rate
B.
Increases the rate
C.
No effect
D.
Reverses the reaction
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Solution
Strong electron-donating groups increase the electron density of the aromatic ring, enhancing its reactivity towards electrophiles.
Correct Answer: B — Increases the rate
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Q. What is the expected product when anisole is treated with chlorosulfonic acid?
A.
Anisole sulfonic acid
B.
p-Anisole sulfonic acid
C.
o-Anisole sulfonic acid
D.
No reaction
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Solution
Chlorosulfonic acid introduces a sulfonyl group at the para position due to the activating effect of the methoxy group.
Correct Answer: B — p-Anisole sulfonic acid
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Q. What is the IUPAC name of the compound formed when phenol undergoes bromination?
A.
Bromophenol
B.
2-Bromophenol
C.
4-Bromophenol
D.
Bromobenzene
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Solution
Bromination of phenol typically occurs at the ortho or para positions, with 2-bromophenol being one of the major products.
Correct Answer: B — 2-Bromophenol
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Q. What is the major product of the electrophilic substitution of toluene with bromine in the presence of FeBr3?
A.
Bromotoluene
B.
Bromobenzene
C.
Benzyl bromide
D.
No reaction
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Solution
Toluene is more reactive than benzene due to the electron-donating methyl group, leading to bromotoluene as the major product.
Correct Answer: A — Bromotoluene
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Q. Which mechanism is primarily involved in the electrophilic substitution of aromatic compounds?
A.
SN1
B.
SN2
C.
E1
D.
E2
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Solution
Electrophilic aromatic substitution primarily follows a mechanism similar to SN1, involving the formation of a carbocation intermediate.
Correct Answer: A — SN1
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Q. Which of the following substituents is a deactivating group in electrophilic aromatic substitution?
A.
Methyl
B.
Hydroxyl
C.
Nitro
D.
Ethyl
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Solution
The nitro group (-NO2) is a strong deactivating group due to its electron-withdrawing nature, making the aromatic ring less reactive.
Correct Answer: C — Nitro
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