Reaction Mechanisms: Substitution, Addition, Elimination - Higher Difficulty Problems
Q. In a nucleophilic substitution reaction, what is the role of the solvent?
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A.
To stabilize the nucleophile
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B.
To stabilize the leaving group
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C.
To provide a medium for the reaction
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D.
To increase the reaction rate
Solution
The solvent can influence the reaction rate by stabilizing the transition state and the reactants involved in the nucleophilic substitution.
Correct Answer: D — To increase the reaction rate
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Q. In an E2 elimination reaction, which of the following is a requirement for the reaction to occur?
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A.
A strong nucleophile
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B.
A good leaving group
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C.
A polar protic solvent
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D.
A tertiary substrate
Solution
E2 reactions require a good leaving group to facilitate the elimination of the leaving group and the formation of a double bond.
Correct Answer: B — A good leaving group
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Q. In the reaction of 2-bromobutane with KOH in ethanol, what type of mechanism is primarily involved?
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A.
SN1
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B.
SN2
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C.
E1
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D.
E2
Solution
The reaction proceeds via an E2 mechanism due to the strong base (KOH) and the presence of a good leaving group (Br).
Correct Answer: D — E2
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Q. What is the IUPAC name of the compound with the formula CH3-CH2-CH(CH3)-CH2-CH3?
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A.
2-pentyl
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B.
3-methylpentane
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C.
2-methylpentane
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D.
3-pentyl
Solution
The longest carbon chain has five carbons, and the methyl group is on the third carbon, making it 3-methylpentane.
Correct Answer: B — 3-methylpentane
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Q. What is the IUPAC name of the compound with the structure CH3-CH(CH3)-C(=O)-OH?
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A.
2-methylbutanoic acid
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B.
3-methylbutanoic acid
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C.
2-methylpropanoic acid
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D.
3-methylpropanoic acid
Solution
The compound is a carboxylic acid with a methyl group on the second carbon, making it 2-methylbutanoic acid.
Correct Answer: A — 2-methylbutanoic acid
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Q. What is the major product of the following reaction: CH3Br + NaOH (ethanol)?
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A.
CH3OH
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B.
CH3O-Na+
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C.
CH3-NaBr
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D.
CH3-CH2-OH
Solution
The reaction is an SN2 substitution where the nucleophile (OH-) attacks the carbon bonded to Br, resulting in the formation of CH3OH.
Correct Answer: A — CH3OH
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Q. What is the major product of the reaction of 2-methyl-2-bromopropane with KOH?
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A.
2-methylpropene
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B.
2-bromopropene
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C.
2-methyl-2-propanol
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D.
No reaction
Solution
The reaction favors elimination due to the bulky substrate, leading to the formation of 2-methylpropene.
Correct Answer: A — 2-methylpropene
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Q. What is the product of the elimination reaction of 2-bromobutane with KOH in ethanol?
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A.
But-1-ene
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B.
But-2-ene
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C.
But-3-ene
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D.
Butane
Solution
The major product is but-2-ene due to the formation of the more stable alkene through elimination.
Correct Answer: B — But-2-ene
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Q. What is the product of the reaction between 1-pentene and HBr?
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A.
1-bromopentane
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B.
2-bromopentane
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C.
3-bromopentane
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D.
4-bromopentane
Solution
The reaction 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 outcome of the reaction of (R)-2-bromobutane with NaOH in a polar aprotic solvent?
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A.
Retention of configuration
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B.
Inversion of configuration
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C.
Racemization
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D.
No reaction
Solution
The reaction proceeds via an SN2 mechanism, leading to inversion of configuration at the chiral center.
Correct Answer: B — Inversion of configuration
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Q. What type of reaction occurs when 1-hexene reacts with HBr?
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A.
Addition
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B.
Substitution
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C.
Elimination
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D.
Oxidation
Solution
The reaction is an electrophilic addition where HBr adds across the double bond of 1-hexene.
Correct Answer: A — Addition
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Q. Which of the following compounds undergoes an SN1 reaction mechanism?
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A.
1-bromopropane
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B.
2-bromopropane
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C.
3-bromopropane
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D.
Bromobenzene
Solution
3-bromopropane is a tertiary alkyl halide, which favors the SN1 mechanism due to the stability of the carbocation formed.
Correct Answer: C — 3-bromopropane
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Q. Which of the following is a characteristic of an SN2 reaction?
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A.
Involves a carbocation intermediate
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B.
Bimolecular reaction rate
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C.
Involves a strong base
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D.
Occurs with tertiary substrates
Solution
SN2 reactions are bimolecular, meaning the rate depends on the concentration of both the substrate and the nucleophile.
Correct Answer: B — Bimolecular reaction rate
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Q. Which of the following reactions is an example of an SN1 mechanism?
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A.
Tertiary alkyl halide with water
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B.
Primary alkyl halide with NaOH
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C.
Secondary alkyl halide with KCN
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D.
Tertiary alkyl halide with NaOEt
Solution
The reaction of a tertiary alkyl halide with water is an SN1 mechanism due to the formation of a stable carbocation.
Correct Answer: A — Tertiary alkyl halide with water
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Q. Which of the following statements about stereochemistry is true for the reaction of 2-bromobutane with NaOH?
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A.
Only R isomer is formed
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B.
Only S isomer is formed
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C.
Both R and S isomers are formed
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D.
No stereoisomers are formed
Solution
The reaction can lead to both R and S isomers due to the nature of the nucleophilic substitution mechanism.
Correct Answer: C — Both R and S isomers are formed
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