Aromatic Compounds and Electrophilic Substitution - Advanced Concepts
Q. In the nitration of toluene, which position is most likely to be attacked by the electrophile?
A.
Ortho position
B.
Meta position
C.
Para position
D.
All positions equally
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Solution
The para position is favored in the nitration of toluene due to the electron-donating effect of the methyl group, which stabilizes the carbocation intermediate.
Correct Answer: C — Para position
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Q. What is the effect of a -CF3 group on the reactivity of an aromatic ring in electrophilic substitution?
A.
Activating
B.
Deactivating
C.
No effect
D.
Reversible
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Solution
The -CF3 group is a strong electron-withdrawing group, making the aromatic ring less reactive in electrophilic substitution.
Correct Answer: B — Deactivating
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Q. What is the IUPAC name of the compound with the formula C6H5-CO-CH3?
A.
Acetophenone
B.
Benzophenone
C.
Phenylacetone
D.
Benzylacetone
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Solution
The compound is acetophenone, which consists of a phenyl group attached to a carbonyl group and a methyl group.
Correct Answer: A — Acetophenone
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Q. What is the IUPAC name of the compound with the structure C6H5-CH2-COOH?
A.
Benzyl acetic acid
B.
Phenylacetic acid
C.
Benzenepropanoic acid
D.
Benzeneacetic acid
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Solution
The correct IUPAC name is phenylacetic acid, as it consists of a phenyl group attached to an acetic acid moiety.
Correct Answer: B — Phenylacetic acid
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Q. What is the major product when anisole (methoxybenzene) undergoes nitration?
A.
Nitroanisole (ortho)
B.
Nitroanisole (para)
C.
Dinitroanisole
D.
Anisole
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Solution
The major product is para-nitroanisole due to the electron-donating effect of the methoxy group, which directs the electrophile to the para position.
Correct Answer: B — Nitroanisole (para)
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Q. What is the product of the reaction of phenol with acetic anhydride?
A.
Phenyl acetate
B.
Acetophenone
C.
Benzyl acetate
D.
Phenyl acetic acid
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Solution
The reaction of phenol with acetic anhydride produces phenyl acetate through an acetylation reaction.
Correct Answer: A — Phenyl acetate
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Q. What is the product of the reaction of phenol with excess bromine?
A.
Bromobenzene
B.
2,4,6-Tribromophenol
C.
Bromophenol
D.
Benzene
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Solution
The product is 2,4,6-tribromophenol, as phenol is highly reactive towards electrophilic substitution and can undergo multiple brominations.
Correct Answer: B — 2,4,6-Tribromophenol
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Q. What is the stereochemical outcome of the electrophilic substitution of 1,2-dimethylbenzene (o-xylene) at the 5-position?
A.
Only one product
B.
Two diastereomers
C.
A racemic mixture
D.
No reaction
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Solution
Electrophilic substitution at the 5-position of o-xylene leads to two diastereomers due to the presence of two chiral centers.
Correct Answer: B — Two diastereomers
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Q. Which of the following compounds is a meta-directing group in electrophilic aromatic substitution?
A.
Amino group (-NH2)
B.
Methyl group (-CH3)
C.
Nitro group (-NO2)
D.
Hydroxyl group (-OH)
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Solution
The nitro group (-NO2) is a meta-directing group because it withdraws electrons from the aromatic ring, making the ortho and para positions less favorable for electrophilic attack.
Correct Answer: C — Nitro group (-NO2)
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Q. Which of the following compounds is a strong activating group for electrophilic aromatic substitution?
A.
-NO2
B.
-CN
C.
-OH
D.
-COOH
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Solution
The -OH group is a strong activating group due to its ability to donate electron density to the aromatic ring.
Correct Answer: C — -OH
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Q. Which of the following compounds is an example of a polycyclic aromatic hydrocarbon?
A.
Naphthalene
B.
Benzaldehyde
C.
Toluene
D.
Phenol
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Solution
Naphthalene is a polycyclic aromatic hydrocarbon, consisting of two fused benzene rings.
Correct Answer: A — Naphthalene
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Q. Which of the following reactions involves a Friedel-Crafts acylation?
A.
Benzene + CH3Cl
B.
Benzene + CH3COCl
C.
Benzene + HNO3
D.
Benzene + H2SO4
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Solution
Friedel-Crafts acylation involves the reaction of benzene with an acyl chloride (like CH3COCl) in the presence of a Lewis acid.
Correct Answer: B — Benzene + CH3COCl
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Q. Which of the following reactions is an example of Friedel-Crafts acylation?
A.
Benzene + CH3Cl in AlCl3
B.
Benzene + CH3COCl in AlCl3
C.
Benzene + HNO3 in H2SO4
D.
Benzene + Br2 in FeBr3
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Solution
Benzene + CH3COCl in AlCl3 is an example of Friedel-Crafts acylation, where an acyl group is introduced to the aromatic ring.
Correct Answer: B — Benzene + CH3COCl in AlCl3
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Q. Which of the following statements about electrophilic aromatic substitution is true?
A.
The aromatic ring acts as a nucleophile.
B.
The electrophile is generated in situ.
C.
Both ortho and para products are formed equally.
D.
The reaction requires a strong base.
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Solution
In electrophilic aromatic substitution, the aromatic ring acts as a nucleophile, attacking the electrophile to form a sigma complex.
Correct Answer: A — The aromatic ring acts as a nucleophile.
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Q. Which of the following substituents on a benzene ring is a strong electron-donating group?
A.
Nitro group (-NO2)
B.
Hydroxyl group (-OH)
C.
Carboxyl group (-COOH)
D.
Methyl group (-CH3)
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Solution
The hydroxyl group (-OH) is a strong electron-donating group due to resonance, enhancing the nucleophilicity of the benzene ring.
Correct Answer: B — Hydroxyl group (-OH)
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