Does p-Toluidine Hydrochloride Dissolve in HCl?

[jnimagine]

chemical reactions with hydrochloric acid

does p-toluidine hydrochloride dissolve in HCl?? When it combines with HCl, what would it produce?

 

[GCT]

Where is the work?

 

[chemisttree]

Are you sure that p-toluidine is an ether?

 

[jnimagine]

Are you sure that p-toluidine is an ether?

I changed the question... so it's supposed to be "chemical reaction with hydrchloric acid" i don't know why it only got changed in my post and not on the others...
anyways...

my idea is that p-toluidinehydrochloride will dissolve in hydrochloric acid, producing p-toluidine and HCl?
I'm very confused about this question...:(

 

[Borek]

Do you know how ammonia reacts with hydrochloric acid? Toluidine (as all amines) is not that different.

 

[jnimagine]

Do you know how ammonia reacts with hydrochloric acid? Toluidine (as all amines) is not that different.

but this one's p-toluidine hydrochloride... so it has another Cl attached to it... how would this react with hydrochloric acid?

 

[Borek]

but this one's p-toluidine hydrochloride... so it has another Cl attached to it... how would this react with hydrochloric acid?

One vs two.

 

[jnimagine]

One vs two.

huh?

 

[Borek]

Take a look at the molecule - and think.

 

[jnimagine]

Take a look at the molecule - and think.

Well...
the hydrogen from the HCl would be donated to the p-touidinehydrochloride... and then the chlorine molecule... joins up with the Cl from HCl??
and since there is a reaction p-toluidinehydrochloride dissolves in HCl??

 

[Borek]

Not bad, although not perfect either. Hydrochlroides are usually 100% dissociated - these are salts. So while you are right that one may expect H⁺ to protonate free -NH₂ group, Cl^- will be just left in the solution.

And I suppose hydrochloride to be already soluble, after all it is an ionic substance. But further protonation should increase solubility.

 

[jnimagine]

Not bad, although not perfect either. Hydrochlroides are usually 100% dissociated - these are salts. So while you are right that one may expect H⁺ to protonate free -NH₂ group, Cl^- will be just left in the solution.

And I suppose hydrochloride to be already soluble, after all it is an ionic substance. But further protonation should increase solubility.

so, the products will just be p-toluidine and Cl-?

 

[Borek]

Not p-toluidine, but protonated (twice) p-toluidine.

 

[jnimagine]

Not p-toluidine, but protonated (twice) p-toluidine.

so would it be p-toluidine with NH3+?

 

[Borek]

Toluidine has two groups that can be protonated. One was protonated from the very beginning, that's why the substance was called toluidine hydrochloride. You put it into acidic solution, it can get protonated for the second time.

Enough spoonfeeding, you are on your own now.

 

[chemisttree]

does p-toluidine hydrochloride dissolve in HCl?? When it combines with HCl, what would it produce?

These are two questions. The first asks about solubility. As you now know, p-toluidine is a hydrochloride salt of an amine. Will that dissolve in acid? (think "like dissolves like")

The second sentence assumes it may need to combine with HCl before it dissolves. Is that true?