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Substitution Comparison
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Problem 1
Problem 2
Problem 3
Problem 4
Problem 5
Problem 6
Problem 7
Substitution Comparison
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7. Substitution Reactions / Substitution Comparison / Problem 5
Problem 5
The given benzylic iodide is inert toward S
N
1 and S
N
2 reactions. Explain why.
A
The S
N
1 reaction is not possible because a bridgehead carbocation can not be formed due to high angle and ring strains.
The S
N
2 reaction is not possible because of the high steric hindrance for the backside attack of the nucleophile.
B
The S
N
1 reaction is not possible because tertiary benzylic carbocations are not stable.
The S
N
2 reaction is not possible because of the high steric hindrance for the backside attack of the nucleophile.
C
The S
N
1 reaction is not possible because the resulting carbocation would be in conjugation with the ring.
The S
N
2 reaction is not possible because the incoming nucleophile would attack the benzene ring instead.
D
The S
N
1 and S
N
2 reactions are not possible because iodide is a poor leaving group.
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