During electrophilic aromatic substitution, a resonance-stabilized cation intermediate is formed. Groups, already present on the benzene ring, that direct ortho/para further stabilize this intermediate by participating in the resonance delocalization of the positive charge. Assume that the following group is present on a benzene ring at position 1 and that you are brominating the ring at positon 4. In the box below draw the structure of the resonance contributor that shows this group actively participating in the charge delocalization. -NH2 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 36E
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During electrophilic aromatic substitution, a resonance-stabilized cation intermediate is formed. Groups, already present on the benzene ring, that direct ortho/para
further stabilize this intermediate by participating in the resonance delocalization of the positive charge.
Assume that the following group is present on a benzene ring at position 1 and that you are brominating the ring at positon 4. In the box below draw the structure
of the resonance contributor that shows this group actively participating in the charge delocalization.
-NH2
You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
C P
opy aste
ChemDoodle
Transcribed Image Text:During electrophilic aromatic substitution, a resonance-stabilized cation intermediate is formed. Groups, already present on the benzene ring, that direct ortho/para further stabilize this intermediate by participating in the resonance delocalization of the positive charge. Assume that the following group is present on a benzene ring at position 1 and that you are brominating the ring at positon 4. In the box below draw the structure of the resonance contributor that shows this group actively participating in the charge delocalization. -NH2 You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. C P opy aste ChemDoodle
Expert Solution
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An electrophile attacks at more nucleophilic site. In case of electron donating group, ortho and para positions are the one carrying negative charge in resonating structure and therefore they are ortho para directing.

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