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Topic: reaction of aniline  (Read 8126 times)

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Offline orgoclear

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reaction of aniline
« on: April 05, 2010, 07:57:05 AM »
what is the product of the following synthesis?

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

Offline Rishi

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Re: reaction of aniline
« Reply #1 on: April 05, 2010, 01:17:33 PM »
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.

Offline pacifyer

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Re: reaction of aniline
« Reply #2 on: April 06, 2010, 02:07:04 PM »
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.

Offline orgoclear

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Re: reaction of aniline
« Reply #3 on: April 07, 2010, 01:53:00 AM »
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 ?

Offline Schrödinger

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Re: reaction of aniline
« Reply #4 on: April 07, 2010, 02:02:50 AM »
Both are correct. The reaction mixture will contain all of them, but in different quantities.
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Offline orgoclear

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Re: reaction of aniline
« Reply #5 on: April 07, 2010, 02:07:39 AM »
major/minor will be which ones ?

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