Then remove sulfonic acid group by desulfonation and you will obtain your ortho-bromoaniline. But we need only one bromine atom to connect to the para position of aniline. Acid/alkaline hydrolysis gives p-bromoaniline. In the above reaction when aniline comes in the vicinity of bromine water, then the bromine molecule develops a polarity within itself and bromine with a slightly positive charge acts as an electrophile (electron seeking) and attacks the electron rich ortho and para positions of aniline. Aniline is a ortho para activator. React Aniline with acetic anhydride and then Bromination (para major product is formed and ortho minor product is formed) diavinad8 and 164 … In this case both substituents will direct the electrophilic substitution in ortho- position with respect to amino group. Therefore we reduce the activity of aniline by the reaction of aniline and ethanoyl chloride (CH 3 COCl). Aniline is heated with acetic anhydride to form acetanilide. Treatment with bromine/acetic acid gives p-bromoacetanilide. When liquid bromine (Br 2(l)) is added to the aniline, it gives 2,4,6-bromoaniline.

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