April 24, 2024, 09:27:25 PM
Forum Rules: Read This Before Posting


Topic: Why use AlCl3?  (Read 3360 times)

0 Members and 1 Guest are viewing this topic.

Offline zsinger

  • Full Member
  • ****
  • Posts: 374
  • Mole Snacks: +18/-60
  • Gender: Male
  • Graduate Chemist
Why use AlCl3?
« on: March 16, 2014, 01:15:09 PM »
All,
I am about to perform a Reduction by iron metal and hydrochloric acid.  I am wondering what the point of the Ferrous Chloride, which the paper calls for, is?  I see no need for it, as FeCl2 is generated in situ……I have examined several suggested mechanisms, drawn them all out by hand, and STILL cannot find where the 1g of FeCl3 comes into play….Any help appreciated.  I know it is prob. a Lewis Acid catalyst to kickstart things, however I just do not see what it coordinates with? 
                -Zack
« Last Edit: March 16, 2014, 01:28:03 PM by zsinger »
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

Offline zsinger

  • Full Member
  • ****
  • Posts: 374
  • Mole Snacks: +18/-60
  • Gender: Male
  • Graduate Chemist
Re: Why use AlCl3?
« Reply #1 on: March 19, 2014, 08:34:37 PM »
Any help appreciated?  I cannot find it after checking literature.
         -Zack
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

Offline zsinger

  • Full Member
  • ****
  • Posts: 374
  • Mole Snacks: +18/-60
  • Gender: Male
  • Graduate Chemist
Re: Why use AlCl3?
« Reply #2 on: March 22, 2014, 12:57:05 PM »
OK……This is what I have come to figure, so somebody please correct me if I am wrong.  I believe that this is a catalyst.
I have reviewed the most advanced literature I can on this reaction, and it is lacking on that last explanation.  Anyways, Im going to use it, as I have it at hand and the paper calls for it, so why mess with what is said to work like a charm :).

FeCl3 is a Lewis Acid Catalyst in FCA, and Ring reactions, however I see nothing that this LA accepts extra electrons from?  In Fact, the extra electrons are contained in the reactive metal itself and need NO LA to donate them, but can rather donate them directly to a Nitro Group for instance.
           -Zack
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
Re: Why use AlCl3?
« Reply #3 on: March 22, 2014, 01:15:10 PM »
This may well be a redox system where the Fe complexes to the nitro group and electrons start jumping about, eventually reducing it to the amine.
It usually works well.
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline zsinger

  • Full Member
  • ****
  • Posts: 374
  • Mole Snacks: +18/-60
  • Gender: Male
  • Graduate Chemist
Re: Why use AlCl3?
« Reply #4 on: March 22, 2014, 03:21:25 PM »
That is precisely what it is.  Just can't see where the FeCl3 fits it :).  Im running the reduction tonight, so I will post conditions, and results.
       -Z
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

Offline zsinger

  • Full Member
  • ****
  • Posts: 374
  • Mole Snacks: +18/-60
  • Gender: Male
  • Graduate Chemist
Re: Why use AlCl3?
« Reply #5 on: March 22, 2014, 03:24:23 PM »
GOT IT!  How about this:  I'll bet it is a catalyst by keeping the [HCl] higher than it normally would be by shifting the equation to the left (I.E. making HCl for reductive purposes).  :)
         -Z
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Why use AlCl3?
« Reply #6 on: March 23, 2014, 11:18:32 PM »
GOT IT!  How about this:  I'll bet it is a catalyst by keeping the [HCl] higher than it normally would be by shifting the equation to the left (I.E. making HCl for reductive purposes).  :)
         -Z

This is unlikely as HCl is consumed in the reaction to form FeCl3 and H2O.

This is a difficult post to answer as it is confusing. The title is, "Why use AlCl3", but nothing in the post refers to AlCl3. The post refers to ferrous chloride, a reductant, but also the addition of one gram of ferric chloride. Okay, I'm confused.

We don't know the scale or anything further about the reaction, but I can imagine ferrous chloride being added because it would be soluble while metallic iron is not. For the purposes of increasing the initial rate, I can see why this might be added. Indeed, the iron will react and dissolve, including forming ferrous chloride. An addition of ferrous chloride may speed up that process.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline zsinger

  • Full Member
  • ****
  • Posts: 374
  • Mole Snacks: +18/-60
  • Gender: Male
  • Graduate Chemist
Re: Why use FeCl3?
« Reply #7 on: March 24, 2014, 01:28:45 AM »
I know, I could not change it.  I figured it out.
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

Sponsored Links