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Chemical reactions with ether?

  1. Sep 27, 2008 #1
    chemical reactions with hydrochloric acid

    does p-toluidine hydrochloride dissolve in HCl?? When it combines with HCl, what would it produce???
     
    Last edited: Sep 27, 2008
  2. jcsd
  3. Sep 27, 2008 #2

    GCT

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    Where is the work?
     
  4. Sep 28, 2008 #3

    chemisttree

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    Are you sure that p-toluidine is an ether?
     
  5. Sep 28, 2008 #4
    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.....:(
     
  6. Sep 29, 2008 #5

    Borek

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    Do you know how ammonia reacts with hydrochloric acid? Toluidine (as all amines) is not that different.
     
  7. Sep 29, 2008 #6
    but this one's p-toluidine hydrochloride... so it has another Cl attached to it... how would this react with hydrochloric acid?
     
  8. Sep 29, 2008 #7

    Borek

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    One vs two.
     
  9. Sep 29, 2008 #8
    huh???
     
  10. Sep 29, 2008 #9

    Borek

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    Take a look at the molecule - and think.
     
  11. Sep 29, 2008 #10
    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??
     
  12. Sep 29, 2008 #11

    Borek

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    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.
     
  13. Sep 29, 2008 #12
    so, the products will just be p-toluidine and Cl-?
     
  14. Sep 29, 2008 #13

    Borek

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    Not p-toluidine, but protonated (twice) p-toluidine.
     
  15. Sep 29, 2008 #14
    so would it be p-toluidine with NH3+?
     
  16. Sep 29, 2008 #15

    Borek

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    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.
     
  17. Sep 30, 2008 #16

    chemisttree

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    Re: chemical reactions with hydrochloric acid

    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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