Aromatic Compounds and Electrophilic Substitution - Case Studies
Q. In the nitration of toluene, what is the major product formed?
A.
Ortho-nitrotoluene
B.
Para-nitrotoluene
C.
Meta-nitrotoluene
D.
Toluene
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Solution
The major product is para-nitrotoluene due to steric hindrance at the ortho position, making the para position more favorable for substitution.
Correct Answer: B — Para-nitrotoluene
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Q. What is the expected product when anisole undergoes bromination?
A.
Bromobenzene
B.
Ortho-bromoanisole
C.
Para-bromoanisole
D.
No reaction
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Solution
The expected product is para-bromoanisole, as the methoxy group is an electron-donating group that directs electrophilic substitution to the para position.
Correct Answer: C — Para-bromoanisole
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Q. What is the IUPAC name of the compound formed when phenol is treated with acetic anhydride?
A.
Acetophenone
B.
Phenyl acetate
C.
Benzyl acetate
D.
Phenyl acetic acid
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Solution
The compound formed is acetophenone, which results from the acetylation of phenol.
Correct Answer: A — Acetophenone
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Q. What is the IUPAC name of the compound with the structure of a benzene ring with a nitro group and a methyl group at the 1 and 2 positions respectively?
A.
2-Nitrotoluene
B.
1-Nitrotoluene
C.
2-Methyl-1-nitrobenzene
D.
1-Methyl-2-nitrobenzene
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Solution
The correct IUPAC name is 1-Methyl-2-nitrobenzene, indicating the positions of the substituents on the benzene ring.
Correct Answer: D — 1-Methyl-2-nitrobenzene
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Q. What is the product of the Friedel-Crafts acylation of benzene with acetyl chloride in the presence of AlCl3?
A.
Acetophenone
B.
Benzophenone
C.
Benzyl acetate
D.
Phenyl acetate
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Solution
The product is acetophenone, formed by the acylation of benzene with acetyl chloride.
Correct Answer: A — Acetophenone
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Q. What is the product of the Friedel-Crafts alkylation of benzene with 1-bromopropane in the presence of AlCl3?
A.
Propylbenzene
B.
Isopropylbenzene
C.
Benzyl bromide
D.
Benzene
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Solution
The product is propylbenzene, formed when benzene reacts with 1-bromopropane in the presence of AlCl3, which generates a propyl cation.
Correct Answer: A — Propylbenzene
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Q. What is the product of the sulfonation of benzene using sulfur trioxide (SO3)?
A.
Benzene sulfonic acid
B.
Benzene thiol
C.
Benzene sulfonate
D.
Benzene disulfonic acid
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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 role of sulfuric acid in the nitration of benzene?
A.
Electrophile
B.
Nucleophile
C.
Catalyst
D.
Solvent
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Solution
Sulfuric acid acts as a catalyst in the nitration of benzene, facilitating the generation of the nitronium ion (NO2+) from nitric acid.
Correct Answer: C — Catalyst
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Q. What is the stereochemical outcome of the electrophilic substitution of a chiral benzene derivative?
A.
Racemic mixture
B.
Enantiomerically pure product
C.
Diastereomers
D.
No stereochemical change
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Solution
Electrophilic substitution on a chiral benzene derivative typically leads to a racemic mixture due to the planar nature of the benzene ring.
Correct Answer: A — Racemic mixture
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Q. Which of the following compounds is an example of a phenolic compound?
A.
Benzene
B.
Phenol
C.
Toluene
D.
Aniline
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Solution
Phenol is a classic example of a phenolic compound, characterized by a hydroxyl group (-OH) attached to a benzene ring.
Correct Answer: B — Phenol
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Q. Which of the following compounds undergoes electrophilic substitution more readily?
A.
Toluene
B.
Benzene
C.
Chlorobenzene
D.
Nitrobenzene
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Solution
Toluene undergoes electrophilic substitution more readily than benzene due to the electron-donating effect of the methyl group, which stabilizes the carbocation intermediate.
Correct Answer: A — Toluene
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Q. Which of the following compounds will undergo electrophilic substitution more readily than benzene?
A.
Phenol
B.
Benzaldehyde
C.
Benzonitrile
D.
Benzyl alcohol
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Solution
Phenol will undergo electrophilic substitution more readily than benzene due to the electron-donating effect of the hydroxyl group.
Correct Answer: A — Phenol
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Q. Which substituent on a benzene ring is a strong deactivator and meta-director in electrophilic substitution?
A.
Hydroxyl group (-OH)
B.
Methyl group (-CH3)
C.
Nitro group (-NO2)
D.
Ethyl group (-C2H5)
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Solution
The nitro group (-NO2) is a strong deactivator and directs incoming electrophiles to the meta position.
Correct Answer: C — Nitro group (-NO2)
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Q. Which substituent on a benzene ring is a strong deactivator and meta-director?
A.
Methyl
B.
Nitro
C.
Hydroxyl
D.
Ethyl
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Solution
The nitro group is a strong deactivator and directs incoming electrophiles to the meta position due to its electron-withdrawing nature.
Correct Answer: B — Nitro
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