18. Reactions of Aromatics:EAS and Beyond
Benzyne
18. Reactions of Aromatics:EAS and Beyond
Benzyne
Benzene can also undergo Nucleophilic Aromatic Substitution via an Elimination-Addition pathway to make aniline. This mechanism requires the formation of a highly unstable aryne (C6H4) intermediate.Â
1
concept
General Mechanism
6m
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What happens in we have an asymmetrical benzyne and has substituents? How do we know which side is going to get attacked?
2
concept
Regiospecificity
3m
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3
example
Activating and deactivating groups
3m
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4
Problem
ProblemWhich is the major product for the following reaction?
A
B
C
D
No reaction
5
Problem
ProblemWhich is the major product for the following reaction?
A
B
C
D
No reaction
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