Does p-Toluidine Hydrochloride Dissolve in HCl?

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Discussion Overview

The discussion centers around the solubility of p-toluidine hydrochloride in hydrochloric acid (HCl) and the chemical reactions that may occur upon mixing. Participants explore the nature of p-toluidine hydrochloride as a hydrochloride salt of an amine and its behavior in acidic solutions.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant questions whether p-toluidine is an ether, indicating confusion about its chemical classification.
  • Another participant suggests that p-toluidine hydrochloride will dissolve in HCl, producing p-toluidine and HCl, expressing confusion about the reaction.
  • Some participants draw parallels between the reaction of p-toluidine hydrochloride and ammonia with hydrochloric acid, noting similarities in behavior.
  • There is a discussion about the dissociation of hydrochlorides, with one participant stating that hydrochlorides are usually 100% dissociated and suggesting that Cl- will remain in solution while H+ may protonate the free -NH2 group.
  • Another participant clarifies that the product of the reaction would be protonated p-toluidine, not free p-toluidine, and discusses the potential for further protonation in an acidic solution.
  • One participant emphasizes that toluidine has two groups that can be protonated, indicating that one group is already protonated in the hydrochloride form.
  • A later reply distinguishes between the two questions posed about solubility and the need for p-toluidine hydrochloride to combine with HCl before dissolving.

Areas of Agreement / Disagreement

Participants express uncertainty and differing views on the nature of the reaction and the products formed. There is no consensus on whether p-toluidine hydrochloride dissolves in HCl or what the exact products of the reaction would be.

Contextual Notes

Participants rely on assumptions about the behavior of hydrochloride salts and their solubility in acidic solutions, which may not be universally applicable. The discussion includes unresolved questions about the specifics of the chemical reactions involved.

jnimagine
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chemical reactions with hydrochloric acid

does p-toluidine hydrochloride dissolve in HCl?? When it combines with HCl, what would it produce?
 
Last edited:
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Where is the work?
 
Are you sure that p-toluidine is an ether?
 
chemisttree said:
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...:(
 
Do you know how ammonia reacts with hydrochloric acid? Toluidine (as all amines) is not that different.
 
Borek said:
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?
 
jnimagine said:
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.
 
Borek said:
One vs two.

huh?
 
Take a look at the molecule - and think.
 
  • #10
Borek said:
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??
 
  • #11
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.
 
  • #12
Borek said:
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-?
 
  • #13
Not p-toluidine, but protonated (twice) p-toluidine.
 
  • #14
Borek said:
Not p-toluidine, but protonated (twice) p-toluidine.

so would it be p-toluidine with NH3+?
 
  • #15
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.
 
  • #16


jnimagine said:
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?
 

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