Reaction Mechanisms: Substitution, Addition, Elimination - Problem Set
Q. In a nucleophilic substitution reaction, what is the role of the nucleophile?
A.
To donate a proton
B.
To accept electrons
C.
To attack the electrophile
D.
To stabilize the leaving group
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Solution
The nucleophile attacks the electrophile, which is typically a carbon atom bonded to a leaving group, facilitating the substitution.
Correct Answer: C — To attack the electrophile
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Q. In an S_N2 reaction, what is the stereochemical outcome when the substrate is a chiral center?
A.
Retention of configuration
B.
Inversion of configuration
C.
Racemization
D.
No stereochemical change
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Solution
S_N2 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. In the context of reaction mechanisms, what does the term 'rate-determining step' refer to?
A.
The fastest step in a reaction
B.
The step with the highest energy barrier
C.
The step that produces the final product
D.
The step that involves the most reactants
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Solution
The rate-determining step is the slowest step in a reaction mechanism, which controls the overall reaction rate.
Correct Answer: B — The step with the highest energy barrier
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Q. What is the major product of the addition of HBr to 2-pentene?
A.
1-bromopentane
B.
2-bromopentane
C.
3-bromopentane
D.
No reaction
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Solution
The addition of HBr follows Markovnikov's rule, leading to the formation of 2-bromopentane as the major product.
Correct Answer: B — 2-bromopentane
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Q. What is the stereochemical configuration of the product formed from the reaction of (R)-2-bromobutane with a strong nucleophile in an S_N2 reaction?
A.
R
B.
S
C.
R and S
D.
No stereochemical change
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Solution
The S_N2 reaction will invert the configuration, resulting in the (S) configuration for the product.
Correct Answer: B — S
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Q. What type of reaction mechanism is involved when an alkyl halide reacts with a nucleophile to form an alcohol?
A.
Elimination
B.
Substitution
C.
Addition
D.
Rearrangement
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Solution
This reaction is a substitution mechanism (S_N2 or S_N1) where the nucleophile replaces the halide.
Correct Answer: B — Substitution
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Q. Which functional group is formed when an alcohol undergoes dehydration?
A.
Ether
B.
Alkene
C.
Alkyne
D.
Aldehyde
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Solution
Dehydration of an alcohol results in the formation of an alkene by the elimination of water.
Correct Answer: B — Alkene
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Q. Which of the following compounds can undergo an E2 elimination reaction?
A.
Tertiary alkyl halides
B.
Primary alkyl halides
C.
Vinyl halides
D.
All of the above
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Solution
Tertiary alkyl halides are most favorable for E2 reactions, but primary and vinyl halides can also undergo E2 under certain conditions.
Correct Answer: A — Tertiary alkyl halides
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Q. Which of the following compounds undergoes an S_N1 reaction mechanism?
A.
1-bromopropane
B.
2-bromopropane
C.
3-bromopropane
D.
Bromobenzene
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Solution
S_N1 reactions are favored by tertiary substrates due to the stability of the carbocation intermediate formed.
Correct Answer: C — 3-bromopropane
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Q. Which of the following is a characteristic of an S_N2 reaction?
A.
Involves a carbocation intermediate
B.
Bimolecular reaction rate
C.
Involves a strong base
D.
Occurs in a polar protic solvent
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Solution
S_N2 reactions are bimolecular and involve a direct attack by the nucleophile, leading to a concerted mechanism without a carbocation.
Correct Answer: B — Bimolecular reaction rate
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Q. Which of the following is a characteristic of E2 elimination reactions?
A.
Requires a strong nucleophile
B.
Involves a carbocation intermediate
C.
Occurs in a single concerted step
D.
Produces a racemic mixture
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Solution
E2 reactions occur in a single concerted step where the base abstracts a proton while the leaving group departs.
Correct Answer: C — Occurs in a single concerted step
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Q. Which of the following statements about stereochemistry is true for E2 reactions?
A.
They require a strong nucleophile
B.
They can lead to both E and Z isomers
C.
They require anti-periplanar geometry
D.
They always produce a racemic mixture
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Solution
E2 reactions require the leaving group and the hydrogen to be anti-periplanar for the elimination to occur.
Correct Answer: C — They require anti-periplanar geometry
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Q. Which of the following statements is true regarding E1 elimination reactions?
A.
They require a strong base
B.
They proceed through a carbocation intermediate
C.
They are stereospecific
D.
They occur in a single step
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Solution
E1 reactions proceed through a carbocation intermediate and are not stereospecific, unlike E2 reactions.
Correct Answer: B — They proceed through a carbocation intermediate
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