Aromatic Compounds and Electrophilic Substitution
Q. In the Friedel-Crafts alkylation of benzene, which of the following is a potential problem?
A.
Polyalkylation
B.
Dealkylation
C.
Hydrogenation
D.
Oxidation
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Solution
Polyalkylation can occur in Friedel-Crafts alkylation, leading to multiple alkyl groups being added to the benzene ring.
Correct Answer: A — Polyalkylation
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Q. What is the IUPAC name of the compound with the formula C6H5CH2OH?
A.
Benzyl alcohol
B.
Phenol
C.
Benzene-1-ol
D.
Benzeneethanol
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Solution
The IUPAC name of C6H5CH2OH is benzyl alcohol, which consists of a benzene ring attached to a -CH2OH group.
Correct Answer: A — Benzyl alcohol
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Q. What is the major product of the electrophilic substitution of benzene with bromine in the presence of FeBr3?
A.
Bromobenzene
B.
Benzyl bromide
C.
Bromobenzyl
D.
Benzene
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Solution
The major product is bromobenzene, formed when bromine reacts with benzene in the presence of a Lewis acid catalyst like FeBr3.
Correct Answer: A — Bromobenzene
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Q. What is the mechanism of the nitration of benzene?
A.
Electrophilic addition
B.
Nucleophilic substitution
C.
Electrophilic substitution
D.
Radical substitution
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Solution
The mechanism of nitration of benzene is electrophilic substitution, where the nitronium ion acts as the electrophile.
Correct Answer: C — Electrophilic substitution
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Q. What is the product of the electrophilic substitution of toluene with sulfuric acid?
A.
Toluene sulfonic acid
B.
Benzene sulfonic acid
C.
Methyl sulfonic acid
D.
Phenol
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Solution
The product is toluene sulfonic acid, formed when toluene reacts with sulfuric acid in an electrophilic substitution reaction.
Correct Answer: A — Toluene sulfonic acid
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Q. What is the product of the Friedel-Crafts acylation of benzene with acetyl chloride (CH3COCl) in the presence of AlCl3?
A.
Acetophenone
B.
Benzophenone
C.
Benzyl acetate
D.
Phenyl acetate
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Solution
The product of the Friedel-Crafts acylation of benzene with acetyl chloride is acetophenone, formed by the introduction of the acetyl group onto the benzene ring.
Correct Answer: A — Acetophenone
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Q. What is the stereochemical outcome of the electrophilic substitution of 1,2-dimethylbenzene (o-xylene) at the 4-position?
A.
Only one product is formed.
B.
Two products are formed, one being a racemic mixture.
C.
Only one enantiomer is formed.
D.
No reaction occurs.
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Solution
Only one product is formed when 1,2-dimethylbenzene is substituted at the 4-position, as the two methyl groups are in positions that do not create stereoisomers.
Correct Answer: A — Only one product is formed.
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Q. Which of the following compounds is least reactive towards electrophilic substitution?
A.
Benzene
B.
Toluene
C.
Nitrobenzene
D.
Anisole
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Solution
Nitrobenzene is least reactive towards electrophilic substitution due to the strong electron-withdrawing effect of the nitro group, which deactivates the ring.
Correct Answer: C — Nitrobenzene
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Q. Which of the following compounds will undergo electrophilic aromatic substitution most readily?
A.
Benzene
B.
Toluene
C.
Chlorobenzene
D.
Nitrobenzene
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Solution
Toluene will undergo electrophilic aromatic substitution most readily due to the electron-donating effect of the methyl group.
Correct Answer: B — Toluene
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Q. Which of the following is a characteristic feature of electrophilic aromatic substitution reactions?
A.
Formation of a carbocation
B.
Formation of a sigma complex
C.
Formation of a free radical
D.
Formation of a carbanion
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Solution
A characteristic feature of electrophilic aromatic substitution reactions is the formation of a sigma complex (arenium ion) during the reaction.
Correct Answer: B — Formation of a sigma complex
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Q. Which of the following is a common electrophile used in the nitration of benzene?
A.
Nitronium ion (NO2+)
B.
Nitrate ion (NO3-)
C.
Nitric acid (HNO3)
D.
Ammonium ion (NH4+)
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Solution
The nitronium ion (NO2+) is the active electrophile in the nitration of benzene, generated from nitric acid and sulfuric acid.
Correct Answer: A — Nitronium ion (NO2+)
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Q. Which of the following is a meta-directing group in electrophilic aromatic substitution?
A.
–NO2
B.
–OH
C.
–CH3
D.
–Cl
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Solution
The –NO2 group is a meta-directing group because it withdraws electrons from the aromatic ring, directing incoming electrophiles to the meta position.
Correct Answer: A — –NO2
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Q. Which of the following substituents is a strong electron-donating group that activates the benzene ring towards electrophilic substitution?
A.
Nitro group (-NO2)
B.
Hydroxyl group (-OH)
C.
Carboxylic acid (-COOH)
D.
Halogens (-X)
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Solution
The hydroxyl group (-OH) is a strong electron-donating group that activates the benzene ring towards electrophilic substitution.
Correct Answer: B — Hydroxyl group (-OH)
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