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7. Substitution Reactions
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Problem 1
Problem 2
Problem 3
Problem 4
Problem 5
Problem 6
Problem 7
Problem 8
Problem 9
Problem 10
Problem 11
Problem 12
Problem 13
Problem 14
Problem 15
7. Substitution Reactions
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7. Substitution Reactions / Substitution Comparison / Problem 14
Problem 14
Explain why, regardless of the base utilized, the following alkyl halide does not undergo a substitution reaction.
A
It does not undergo the S
N
1 reaction because of steric hindrance preventing it from being attacked by a nucleophile. It does not undergo the S
N
2 reaction because the multi-ring structure prevents the sp
2
carbon in the carbocation formed from having a 120° bond angle making the carbocation unstable.
B
It does not undergo the S
N
2 reaction because of steric hindrance preventing it from being attacked by a nucleophile. It does not undergo the S
N
1 reaction because the multi-ring structure prevents the sp
2
carbon in the carbocation formed from having a 120° bond angle making the carbocation unstable.
C
It does not undergo the S
N
1 reaction because of steric hindrance preventing it from being attacked by the leaving group. It does not undergo the S
N
2 reaction because the multi-ring structure permits the sp
2
carbon in the carbocation formed having a 120° bond angle making the carbocation unstable.
D
It does not undergo the S
N
2 reaction because of steric hindrance preventing it from being attacked by an electrophile. It does not undergo the S
N
1 reaction because the multi-ring structure prevents the sp
2
carbon in the carbocation formed from having a 180° bond angle making the carbocation stable.
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