A limitation of the Friedel-Crafts alkylation reaction is that the presence of moderately/strongly deactivating groups results in poor yields. Consider aniline, which is not very reactive towards Friedel-Crafts alkylation. NH2 -NH2 group deactivating relative to H? a. Page I of 3 b. Why does this substituted benzene derivative not give good yields of alkylated product when subjected to Friedel Crafts alkylation using an alkyl halide and AICI3 Lewis acid?

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
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Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 17E
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2. A limitation of the Friedel-Crafts alkylation reaction is that the presence of
moderately/strongly deactivating groups results in poor yields. Consider aniline,
which is not very reactive towards Friedel-Crafts alkylation.
NH2
a. Is the -NH2 group deactivating relative to H?
Page 1 of 3
b. Why does this substituted benzene derivative not give good yields of
alkylated product when subjected to Friedel Crafts alkylation using an alkyl
halide and AICI, Lewis acid?
Transcribed Image Text:2. A limitation of the Friedel-Crafts alkylation reaction is that the presence of moderately/strongly deactivating groups results in poor yields. Consider aniline, which is not very reactive towards Friedel-Crafts alkylation. NH2 a. Is the -NH2 group deactivating relative to H? Page 1 of 3 b. Why does this substituted benzene derivative not give good yields of alkylated product when subjected to Friedel Crafts alkylation using an alkyl halide and AICI, Lewis acid?
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