arylamines

anniline doesnot undergoes friedel crafts alkylation and acylation . Can anybody give me the reason

11 Answers

11
Anirudh Narayanan ·

Because of basic nature, aniline reacts with the Lewis Acid.

11
Sunil Kumar ·

Aniline doesn't undergo Friedal-Craft(alkylation and acylation) reaction because of the salt formation with the aluminium chloride(which act as the catalyst). As a result, nitrogen of aniline acquires the positive charge and hence acts as a strong deactivating group for further reaction......

1
greatvishal swami ·

yup sankar above two resons r correct

also phenol doent undergo friedel craft reactions due to this very reason

1
voldy ·

that's only if use u use the amount of catalyst used normally . if used in excess , the reaction proceeds . Interestingly , the meta product is obtained. I'd like one of you to give the probable mechanism .

33
Abhishek Priyam ·

Well may be....I think -OH reacts with lewis acid and becomes ring deactivator.. well may be

1
chinmay ·

b'cos of the lone pair on nitrogen,anniline
reacts with AlCl3(a lewis acid)to form a salt.Due to this the nitrogen acquires positive charge and deactivates the benzene ring.

1
greatvishal swami ·

@srinath,priyam,chinmay

deactived ring doesnt undergo friedel craft reactions

1
voldy ·

it does dear.

1
voldy ·

I'm sure of this. pucca . no q's here. and the planr prob is still a Q . I'll try to give the best answer. I'll only try mind u .and answer the synthesis problems no? U said Organic was ur fav ???

1
greatvishal swami ·

yup bro i will ans them dat day i lost intrest sry fr dat

and also i m also pakka dat deactivated rings dont undergo dis reaction

i m givin sm lines in my support frm my reference book

"Aromatic compounds containing m-directing groups do not undergo Friedel-Crafts alkylation.This is because in such cases the ring is deactivated and the attaking carbocation(electrophile) is less reactive to bring about the reaction.On the other hand , electrophiles NO+2,SO3 and positive hydrogen, etc. are reacive enough to bring about the substitution even on deactivated aromatic rings."

bt they can undergo acylation bt yield is too poor

1
voldy ·

yup , the yield is poor . I agree da.

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