1. Why does aniline not undergo freidel crafts alkylation, though phenol does? 2. what is the use of AlCl3 in freidel crafts acylation? Is it a catalyst? If so, how does it catalyze?

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Grade 12Organic Chemistry

1. Why does aniline not undergo freidel crafts alkylation, though phenol does?

2. what is the use of AlCl₃in freidel crafts acylation? Is it a catalyst? If so, how does it catalyze?

jee king king

16 Years agoGrade 12

5 Answers

Sahil Kochar

16 Years ago

1.Aniline doesnt undergo friedel craft rxn because the reagent AlCl3,being e- deficient acts as lewis base and attacks on the lone pair of nitrogen present in aniline to form an insoluble complex which precipitates out and the rxn doesnt proceed.

2.AlCl3 is the reagent which was used by Friedel Craft in alkylation and acylation,actually any other lewis acid can also be used because these are just catalysing reagents which increase the probability and feasibility of the aromatic substitution.....

Srikant Mahapatra

16 Years ago

Listen jee king, who told you that phenol undergoes Friedel-Crafts alkylation; even it does not facilitate the reaction because the Lewis acid catalyst coordinates with one of the lone pairs of electrons present on oxygen of -OH group.

abhishek

9 Years ago

because of aniline is an very good nucleophile...so at the of giving pair of e to Alcl3 aniline does in place of alkyl halide...,

abhishek

9 Years ago

because of aniline is an very good nucleophile...so at the time of giving pair of e to Alcl3 aniline does in place of alkyl halide...,

Harish

8 Years ago

Because aniline form salt with AlCl3 which deactivates benzene ring by decreasing electron density and AlCl3 do not form electrophile for electrophilic substitution reaction