Reaction Mechanisms: Substitution, Addition, Elimination - Advanced Concepts
Q. In the reaction of benzyl chloride with a strong nucleophile, which mechanism is favored?
A.
SN1
B.
SN2
C.
E1
D.
E2
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Solution
Benzyl chloride can stabilize a carbocation, thus the SN1 mechanism is favored when reacting with a strong nucleophile.
Correct Answer: A — SN1
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Q. What is the IUPAC name for the compound with the structure CH3-CH2-CH(CH3)-CH2-Br?
A.
1-bromo-3-methylbutane
B.
2-bromo-3-methylbutane
C.
3-bromo-2-methylbutane
D.
2-bromo-2-methylbutane
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Solution
The longest carbon chain has four carbons, and the bromine is on the second carbon, making the correct IUPAC name 2-bromo-3-methylbutane.
Correct Answer: B — 2-bromo-3-methylbutane
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Q. What is the main mechanism for the reaction of 1-bromobutane with sodium hydroxide in ethanol?
A.
SN1
B.
SN2
C.
E1
D.
E2
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Solution
The reaction of 1-bromobutane with sodium hydroxide in ethanol proceeds via the SN2 mechanism due to the primary nature of the substrate, allowing for a backside attack.
Correct Answer: B — SN2
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Q. What is the main mechanism for the reaction of 2-bromobutane with sodium hydroxide in ethanol?
A.
SN1
B.
SN2
C.
E1
D.
E2
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Solution
The reaction proceeds via an SN2 mechanism due to the primary nature of the substrate and the strong nucleophile (OH-).
Correct Answer: B — SN2
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Q. What is the major product of the reaction between propene and HBr?
A.
1-bromopropane
B.
2-bromopropane
C.
Bromopropane mixture
D.
No reaction
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Solution
The major product is 2-bromopropane due to Markovnikov's rule, where H adds to the less substituted carbon.
Correct Answer: B — 2-bromopropane
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Q. What is the major product of the reaction of 2-bromo-2-methylpropane with a strong base?
A.
2-methylpropene
B.
2-bromo-2-methylpropane
C.
Isobutylene
D.
No reaction
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Solution
The strong base induces an E2 elimination reaction, leading to the formation of 2-methylpropene as the major product.
Correct Answer: A — 2-methylpropene
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Q. What is the product of the E1 elimination of 2-bromo-2-methylpropane?
A.
Isobutylene
B.
Butane
C.
2-methylpropene
D.
Cyclobutane
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Solution
E1 elimination of 2-bromo-2-methylpropane leads to the formation of 2-methylpropene as the major product.
Correct Answer: C — 2-methylpropene
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Q. What is the product of the reaction between propene and HBr?
A.
1-bromopropane
B.
2-bromopropane
C.
Propyl bromide
D.
Bromopropane
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Solution
The addition of HBr to propene follows Markovnikov's rule, leading to the formation of 2-bromopropane as the major product.
Correct Answer: B — 2-bromopropane
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Q. What type of stereochemistry is observed in the product of an SN2 reaction?
A.
Retention of configuration
B.
Inversion of configuration
C.
Racemization
D.
No stereochemistry change
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Solution
SN2 reactions result in inversion of configuration at the chiral center due to the backside attack of the nucleophile.
Correct Answer: B — Inversion of configuration
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Q. Which of the following compounds undergoes elimination via an E2 mechanism?
A.
2-bromopentane
B.
2-bromo-2-methylpropane
C.
1-bromobutane
D.
3-bromopropanol
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Solution
2-bromopentane can undergo E2 elimination because it has a beta-hydrogen available for elimination, while the others either do not or favor different mechanisms.
Correct Answer: A — 2-bromopentane
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Q. Which of the following is a characteristic of an SN1 reaction?
A.
Involves a concerted mechanism
B.
Forms a carbocation intermediate
C.
Requires a strong nucleophile
D.
Occurs in a single step
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Solution
SN1 reactions involve the formation of a carbocation intermediate, which is a key characteristic of this two-step mechanism.
Correct Answer: B — Forms a carbocation intermediate
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Q. Which of the following statements is true regarding E1 reactions?
A.
They are stereospecific
B.
They involve a carbocation intermediate
C.
They require a strong base
D.
They occur in a single step
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Solution
E1 reactions involve the formation of a carbocation intermediate, making them a two-step process.
Correct Answer: B — They involve a carbocation intermediate
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Q. Which of the following statements is true regarding the E2 mechanism?
A.
It requires a strong base
B.
It can occur with tertiary substrates only
C.
It involves a carbocation intermediate
D.
It is a unimolecular reaction
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Solution
E2 mechanisms require a strong base to abstract a proton while the leaving group departs in a concerted manner.
Correct Answer: A — It requires a strong base
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