[KatS603]

Equimolar amounts of the aldehyde (4-chlorobenzaldehyde) and ketone (4-bromoacetophenone) were used, coupled with excess of NaOH. Crude product obtained had a gummy consistency, green-grey colour and a slight minty smell. Recrystallization via hot Ethanol yielded a white crystal powder (odourless). Melting point has not yet been determined.

I know it is not Perilla, Menthofurane, nor pulegon. Any ideas what it might be...

Molecular formula: C15H10ClBrO.

[KritikalMass]

Equimolar amounts of the aldehyde (4-chlorobenzaldehyde) and ketone (4-bromoacetophenone) were used, coupled with excess of NaOH. Crude product obtained had a gummy consistency, green-grey colour and a slight minty smell.

Hi Kat,
I am not going to attempt to answer this question right now since I was out all day repairing my vehicle and my mind is not in Ochem gear right now. But one real quick question- under the conditions you described is the aldehyde going to react with the ketone? If so, how?

[KatS603]

The 4-bromoacetophenone would react with the NaOh creating an Enolate molecule. The 4-Chlorobenzaldehyde would then react with the alpha carbon of the enolate severing the C-C double bond and attaching itself to the alpha carbon, causing the electron transfer from the C=O double bond onto the O causing it to be O-. At this point the reaction is quenched with excess water and the O- deprotonates the water resulting in the compound + OH-. In the last step the OH- and the residual Na+ from the Enolate step would each deprotonate the compound. One would deprotonate the original alpha carbon while the other would deprotonate the OH which is on what was formerly the aldehyde. What results is my mystery ketone.

Here's a rough equation:

....O
.||
4-Br-C6H4-C-CH3

...+

4-Cl-C6H4-CH=O

.||
.||
.\/
....O
...||
4-Br-C6H4-C-CH=CH-C6H4-Cl

[KritikalMass]

I think you formed some sort of enone in the first step- don't have the software to draw it out since I am using Linux 

I am mainly replying so that your thread is getting bumped and maybe someone more experienced will see it and come in with some much better advice than what I have to offer. That way we both learn!

[nj_bartel]

Your reasoning sounds good to me.  The product you drew should be your major product.

[KritikalMass]

Ok, one more small step in what I think is the right direction. It looks like you are dealing with a halogenated chalcone

I have no idea how to name these things, but maybe it will give you something to work with.

The pic I posted is not of the halogenated chalcone you produced but think the structure and process is the exact same minus the bromine and chlorine. Maybe it will help you figure out a name so you can look it up since nj_bartel said it should be your major product.

Hope that helped!

[nj_bartel]

That is the right product (+ p-halogens), and it is a chalcone 

[KatS603]

Thanks everyone for the *delete me* 

[KritikalMass]

yea, please let me know if it was of any help- hope you do good!