Draw resonance structures for the intermediate carbocations in the bromination of this structure by...

Question

Draw resonance structures for the intermediate carbocations in the bromination of this structure by electrophilic aromatic substitution. Is this compound a para/ortho or meta director? Why?

David · Accepted Answer

Solution081112_49058_3
H
H
intermediate for ortho- substitution
CH3
intermediate for para-substitution
CH3
H
H
intermediate for ortho- substitution
CH3
intermediate for para-substitution
CH3

The alkene group attached to the benzene ring is ortho- and para-directing as it 
stabilizes the intermediate arises out of ortho- and para- substitutions by 
resonance effect through electron donation.
H
H
ortho- substitution
para-substitution
CH3
CH3
H
H
CH3
CH3
H
H
ortho- substitution
para-substitution
CH3
CH3
H
H
CH3
CH3

Draw resonance structures for the intermediate carbocations in the bromination of this structure by electrophilic aromatic substitution. Is this compound a para/ortho or meta director? Why?

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