Reaction Mechanisms: Substitution, Addition, Elimination - Applications
Q. In an electrophilic addition reaction of HBr to propene, what is the major product formed?
A.
1-bromopropane
B.
2-bromopropane
C.
Propyl bromide
D.
Bromopropane
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Solution
The major product is 2-bromopropane due to Markovnikov's rule, where the bromine adds to the more substituted carbon.
Correct Answer: B — 2-bromopropane
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Q. What is the IUPAC name of the compound with the formula CH3-CH2-CH(CH3)-CH2-Br?
A.
1-bromo-3-methylbutane
B.
2-bromo-3-methylbutane
C.
3-bromo-2-methylbutane
D.
2-bromo-4-methylbutane
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Solution
The longest carbon chain has four carbons, and the bromine is on the first carbon, making it 1-bromo-3-methylbutane.
Correct Answer: B — 2-bromo-3-methylbutane
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Q. What is the main mechanism of the reaction between an alkyl halide and a nucleophile in a bimolecular nucleophilic substitution (SN2) reaction?
A.
Formation of a carbocation
B.
Direct attack of the nucleophile
C.
Formation of a cyclic intermediate
D.
Elimination of a leaving group
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Solution
In an SN2 reaction, the nucleophile directly attacks the electrophilic carbon, leading to the simultaneous displacement of the leaving group.
Correct Answer: B — Direct attack of the nucleophile
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Q. What is the major product of the reaction of 1-chloropropane with sodium hydroxide in an SN2 mechanism?
A.
1-propanol
B.
2-propanol
C.
Propyl chloride
D.
Sodium chloride
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Solution
The reaction of 1-chloropropane with sodium hydroxide in an SN2 mechanism results in the formation of 1-propanol through nucleophilic substitution.
Correct Answer: A — 1-propanol
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Q. What is the major product of the reaction of 2-methylpropene with H2 in the presence of a platinum catalyst?
A.
2-methylpropane
B.
2-methylpropene
C.
Cyclopropane
D.
No reaction
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Solution
The reaction of 2-methylpropene with H2 in the presence of a platinum catalyst results in the hydrogenation of the alkene to form 2-methylpropane.
Correct Answer: A — 2-methylpropane
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Q. What is the product of the reaction of benzene with bromine in the presence of a Lewis acid catalyst?
A.
Bromobenzene
B.
Benzyl bromide
C.
Bromobenzyl
D.
Benzene dibromide
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Solution
The reaction of benzene with bromine in the presence of a Lewis acid catalyst leads to the substitution of a hydrogen atom with a bromine atom, forming bromobenzene.
Correct Answer: A — Bromobenzene
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Q. What type of stereochemistry is observed in the product of the reaction between 2-bromobutane and a strong base in an E2 elimination?
A.
R configuration
B.
S configuration
C.
Trans configuration
D.
Cis configuration
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Solution
E2 elimination typically leads to the formation of alkenes with trans stereochemistry due to the anti-periplanar requirement.
Correct Answer: C — Trans configuration
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Q. Which of the following compounds can undergo an SN1 reaction?
A.
1-bromopropane
B.
2-bromopropane
C.
3-bromopropane
D.
Bromobenzene
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Solution
3-bromopropane can undergo an SN1 reaction due to the stability of the tertiary carbocation that forms during the reaction.
Correct Answer: C — 3-bromopropane
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Q. Which of the following compounds undergoes elimination to form an alkene most readily?
A.
1-bromopropane
B.
2-bromopropane
C.
3-bromopropane
D.
1-bromo-2-methylpropane
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Solution
3-bromopropane undergoes elimination more readily due to the stability of the tertiary carbocation formed during the reaction.
Correct Answer: C — 3-bromopropane
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Q. Which of the following is a characteristic feature of nucleophilic substitution reactions?
A.
Formation of a stable intermediate
B.
Involvement of a leaving group
C.
Formation of a radical
D.
No change in hybridization
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Solution
Nucleophilic substitution reactions involve the displacement of a leaving group by a nucleophile, which is a defining characteristic of these reactions.
Correct Answer: B — Involvement of a leaving group
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Q. Which of the following statements about the E1 elimination mechanism is true?
A.
It involves a concerted mechanism.
B.
It forms a carbocation intermediate.
C.
It is favored by strong bases.
D.
It occurs in a single step.
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Solution
E1 elimination involves the formation of a carbocation intermediate, making it a two-step process.
Correct Answer: B — It forms a carbocation intermediate.
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Q. Which of the following statements about the E2 elimination mechanism is true?
A.
It involves a carbocation intermediate.
B.
It requires a strong base.
C.
It is a unimolecular process.
D.
It occurs in a stepwise manner.
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Solution
E2 elimination requires a strong base to abstract a proton while the leaving group departs, and it occurs in a single concerted step.
Correct Answer: B — It requires a strong base.
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