Eugenol and Eugenol acetate reaction questions

[TeenieBopper]

Homework Statement

Complete the following reactions, giving the correct structure for each organic product:
eugenol + FeCl_3 ->

eugenol acetate + FeCl_3 ->

Homework Equations

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.

 

[Borek]

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.

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

I learned in lecture that when an alkene reacts with a halogen in the presence of a catalyst (Cl_2 and FeCl_3, respectfully)

And you added a halogen?

 

[TeenieBopper]

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

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.

And you added a halogen?

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?

 

[Borek]

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

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

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?

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.