[orgoclear]

what is the product of the following synthesis?

aniline --> (conc. H2SO4)  --> (Br2/H2O)  --> product

[Rishi]

Since the temperature of reaction is not specified, I take the liberty to assume.Aniline reacting with sulfuric acid at 180 degrees to form sulfanilic acid. This sulfanilic acid if reacted with Bromine to give 2,6-Dibromosulfanilic acid which is hydrolysed in water containing some acid catalyst to give 2,6-Dibromo aniline.

This is the best possibility i can arrive at looking at your data.

[pacifyer]

Since the temperature of reaction is not specified, I take the liberty to assume.Aniline reacting with sulfuric acid at 180 degrees to form sulfanilic acid. This sulfanilic acid if reacted with Bromine to give 2,6-Dibromosulfanilic acid which is hydrolysed in water containing some acid catalyst to give 2,6-Dibromo aniline.

This is the best possibility i can arrive at looking at your data.

Alternatively, the acid could protonate the amino group, to form an anilinium ion, which would be brominated at the m-position.

[orgoclear]

replying to the last two posts:

the book states the answer to be 2,4,6 tribromo aniline (presuming that Br2/H2O is in excess)

while i feel that the aniline will get protonated leading to bromination at m-position (as it happens in nitration)

So, which would be correct ?

[Schrödinger]

Both are correct. The reaction mixture will contain all of them, but in different quantities.

[orgoclear]

major/minor will be which ones ?