Reaction Mechanisms: Substitution, Addition, Elimination - Numerical Applications
Q. In an SN2 reaction, which of the following substrates would react the fastest with a nucleophile?
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A.
tert-butyl chloride
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B.
isopropyl bromide
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C.
ethyl chloride
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D.
methyl iodide
Solution
Methyl iodide reacts the fastest in an SN2 reaction due to minimal steric hindrance and the good leaving ability of iodide.
Correct Answer: D — methyl iodide
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Q. In the reaction of benzene with bromine in the presence of FeBr3, what type of reaction occurs?
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A.
Electrophilic substitution
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B.
Nucleophilic substitution
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C.
Addition
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D.
Elimination
Solution
This reaction is an electrophilic aromatic substitution where bromine acts as an electrophile.
Correct Answer: A — Electrophilic substitution
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Q. What is the expected product when 2-bromo-2-methylpropane reacts with a strong base in a bimolecular elimination reaction?
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A.
2-methylpropene
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B.
2-bromopropane
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C.
2-methyl-2-bromopropane
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D.
Propane
Solution
The strong base facilitates the E2 elimination, resulting in the formation of 2-methylpropene.
Correct Answer: A — 2-methylpropene
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Q. What is the IUPAC name for the compound with the formula CH3-CH2-CH(Cl)-CH3?
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A.
1-chlorobutane
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B.
2-chlorobutane
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C.
3-chlorobutane
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D.
butyl chloride
Solution
The compound is a four-carbon chain with a chlorine substituent on the second carbon, making it 2-chlorobutane.
Correct Answer: B — 2-chlorobutane
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Q. What is the IUPAC name of the compound with the formula C4H9Br?
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A.
1-bromobutane
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B.
2-bromobutane
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C.
1-bromo-2-methylpropane
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D.
2-bromo-2-methylpropane
Solution
The compound with the formula C4H9Br is 1-bromobutane, as it is a straight-chain brominated alkane.
Correct Answer: A — 1-bromobutane
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Q. What is the major product of the reaction of 1-pentene with H2 in the presence of a palladium catalyst?
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A.
Pentane
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B.
1-pentanol
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C.
2-pentanol
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D.
Cyclopentane
Solution
The reaction is a hydrogenation that converts 1-pentene to pentane, a saturated hydrocarbon.
Correct Answer: A — Pentane
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Q. What is the product of the reaction between ethene and HBr?
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A.
Bromoethane
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B.
Ethyl bromide
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C.
1-bromopropane
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D.
2-bromopropane
Solution
The addition of HBr to ethene results in the formation of bromoethane through an electrophilic addition mechanism.
Correct Answer: A — Bromoethane
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Q. What is the product of the reaction of 1-chloropropane with potassium thiocyanate?
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A.
propyl thiocyanate
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B.
propyl isothiocyanate
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C.
1-thiocyanatopropane
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D.
no reaction
Solution
The reaction produces propyl thiocyanate through an SN2 mechanism, where the thiocyanate ion acts as a nucleophile.
Correct Answer: A — propyl thiocyanate
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Q. What is the stereochemical outcome of the SN2 reaction of (R)-2-bromobutane with sodium iodide?
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A.
(R)-2-iodobutane
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B.
(S)-2-iodobutane
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C.
(R)-2-bromobutane
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D.
(S)-2-bromobutane
Solution
The SN2 mechanism inverts the configuration at the chiral center, resulting in (S)-2-iodobutane.
Correct Answer: B — (S)-2-iodobutane
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Q. What type of reaction occurs when 2-bromobutane reacts with sodium ethoxide?
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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 of 2-bromobutane with sodium ethoxide is an E2 elimination reaction, leading to the formation of an alkene.
Correct Answer: D — E2
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Q. Which mechanism is likely to occur when 2-bromo-2-methylpropane reacts with a strong nucleophile?
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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 will proceed via the SN1 mechanism due to the tertiary carbon, which stabilizes the carbocation intermediate.
Correct Answer: A — SN1
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Q. Which of the following compounds is most likely to undergo an E1 reaction?
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A.
1-bromobutane
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B.
2-bromobutane
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C.
3-bromobutane
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D.
1-bromo-2-methylpropane
Solution
3-bromobutane is most likely to undergo an E1 reaction due to the stability of the tertiary carbocation formed during the reaction.
Correct Answer: C — 3-bromobutane
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Q. Which of the following compounds undergoes elimination more readily?
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A.
1-bromopropane
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B.
2-bromobutane
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C.
3-bromopentane
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D.
1-bromo-2-methylpropane
Solution
3-bromopentane undergoes elimination more readily due to the stability of the tertiary carbocation formed during the reaction.
Correct Answer: C — 3-bromopentane
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Q. Which of the following compounds undergoes elimination to form an alkene when treated with a strong base?
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A.
1-bromobutane
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B.
2-bromobutane
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C.
1-bromo-2-methylpropane
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D.
2-bromo-2-methylpropane
Solution
2-bromobutane undergoes elimination (E2) to form an alkene, while 2-bromo-2-methylpropane does not due to steric hindrance.
Correct Answer: B — 2-bromobutane
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