Textbook Question
Predict the product of the following Friedel–Crafts acylation reactions.
(b)
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19. Reactions of Aromatics: EAS and Beyond
Electron Withdrawing Groups
Multiple Choice
Predict the major productof the following EAS reaction.
A
B
C
D
10 Comments
Verified step by step guidance1
Identify the type of reaction: The reaction is an Electrophilic Aromatic Substitution (EAS) involving chlorination, catalyzed by FeCl3.
Determine the directing effects: The amide group (NHCO) is a moderately activating, ortho/para-directing group. It will direct the incoming chlorine to the ortho or para position relative to itself on the benzene ring it is attached to.
Consider steric and electronic effects: The para position is often favored over the ortho position due to less steric hindrance, unless the ortho position is significantly more activated or the para position is blocked.
Predict the major product: Based on the directing effects and steric considerations, the chlorine will most likely substitute at the para position relative to the amide group on the benzene ring it is attached to.
Verify the structure: Ensure that the predicted major product is consistent with the expected regioselectivity of the EAS reaction, considering the influence of the amide group.
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