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Eugenol and Eugenol acetate reaction questions

  1. Nov 14, 2012 #1
    1. The problem statement, all variables and given/known data
    Complete the following reactions, giving the correct structure for each organic product:
    eugenol + FeCl_3 ->

    eugenol acetate + FeCl_3 ->


    2. Relevant equations



    3. The attempt at a solution

    When I did this lab, my partner and I didn't notice a reaction when we added FeCl_3 to our eugenol product, but that seems too easy; why would they ask what the product is if there wasn't a reaction.

    However, both eugenol and eugenol acetate have an alkene. I learned in lecture that when an alkene reacts with a halogen in the presence of a catalyst (Cl_2 and FeCl_3, respectfully) the double bond becomes a single bond and each side takes one of the halogen atoms. So does the alkene end simply become CClH-2-CClH_2 for both eugenol and eugenol acetate?

    Any help is greatly appreciated.
     
  2. jcsd
  3. Nov 14, 2012 #2

    Borek

    User Avatar

    Staff: Mentor

    Not good, in theory you should observe a color change.

    And you added a halogen?
     
  4. Nov 14, 2012 #3
    Well, the solution with the eugenol products was clear, and the FeCl_3 was yellow, and when we mixed the two, the solution was yellow. I just assumed that it was because of the FeCl_3.



    Yeah, this was why I was confused, because we didn't explicitly add a halogen.

    I did some more reading, and I found something about Fe reacting and creating complexes with OH groups. Would the product for for Eugenol + FeCl_3 essentially be six pointed star with Fe at the center, bonded with the O from the OH group from the eugenol? And then, because eugenol acetate doesn't have any OH groups, it doesn't react with the FeCl_3?
     
  5. Nov 14, 2012 #4

    Borek

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    Staff: Mentor

    So if you didn't add the halogen, it couldn't react with a double bond.

    You are on the right track. Fe(III) should react with phenolic -OH creating a color complex. From what I read, in the case of eugenol color doesn't have to be stable.
     
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