[Fragment_Error]

Hey, I have to find out what the major chemical component that constitutes the volatile oils from dill seeds, and I've found out that it's carvone: C₁₀H₁₄O

And now I have to write equations for the reaction of carvone with 2,4-DNP and Br₂\CCl₄

Ok 2,4-DNP is C₆H₄N₂O₅ but how will the two react? I know that the bond joining the two will be a C=O bond, but where will it occur? And I think a product will be water?

[sjb]

Hey, I have to find out what the major chemical component that constitutes the volatile oils from dill seeds, and I've found out that it's carvone: C₁₀H₁₄O

And now I have to write equations for the reaction of carvone with 2,4-DNP and Br₂\CCl₄

Ok 2,4-DNP is C₆H₄N₂O₅ but how will the two react? I know that the bond joining the two will be a C=O bond, but where will it occur? And I think a product will be water?

Do you know the actual structual formulae of carvone and 2,4-DNP - perhaps that may help?

S

[Fragment_Error]

Ok, I found the structural formula, and yeah it did make it a little easier.

Does this look ok?




Also, what is a major advantage of using steam distillation as a way of separating volatile components from plant material opposed to solvent extraction?

[sjb]

Ok, I found the structural formula, and yeah it did make it a little easier.

Does this look ok?

Hmm, it helps a little To be honest, the second structure's not what I had in my mind when I saw 2,4-DNP, though I can see where the confusion's arisen. What does your question actually say?

[Fragment_Error]

It simply says,

"write the equation for the reactions of this compound (carvone) with:

i) 2,4-DNP


ii) Br₂\CCl₄"

[sjb]

OK,

To me, the reagent 2,4-DNP (especially with a carbonyl as the other half) would refer to 2,4-dinitrophenylhydrazine - Brady's reagent, and not the phenol.

I think if the phenol did add to carvone, it may end up with something with a cyclic diene - I'll try and get an image together, or perhaps a pair of diastereomeric 1,4-adducts - controlled by the isopropenyl group??

(just noticed image upload is not working, have to think of some names now )

S

[sjb]

(just noticed image upload is not working, have to think of some names now )

S

I think upload should be working now, from what I've seen in other parts of the forum, so here's what I think the main product will be:

I think 1,4 addition would be less favoured, as the phenol is a harder acid, if you had the thiophenol then perhaps 1,4 might be more favoured...

[Panoramix]

2,4-DNP is very likely to be 2,4-Dinitrophenyl hydrazine and not 2,4-Dinitrophenol.

If you ask google about "2,4-DNP" you will get an answer immediately about what is going to happen with your ketone.

About Br2/CCl4: think about first year chemistry, double bonds, etc. and again asking google "bromine carvone" might give more ideas

[sjb]

2,4-DNP is very likely to be 2,4-Dinitrophenyl hydrazine and not 2,4-Dinitrophenol.

If you ask google about "2,4-DNP" you will get an answer immediately about what is going to happen with your ketone.

Indeed, though the very first hit *I* get is http://ptcl.chem.ox.ac.uk/MSDS/DN/2,4-DNP.html , which refers to the phenol. Google is not the be-all and end-all.

S

[Panoramix]

2,4-DNP is very likely to be 2,4-Dinitrophenyl hydrazine and not 2,4-Dinitrophenol.

If you ask google about "2,4-DNP" you will get an answer immediately about what is going to happen with your ketone.

Indeed, though the very first hit *I* get is http://ptcl.chem.ox.ac.uk/MSDS/DN/2,4-DNP.html , which refers to the phenol. Google is not the be-all and end-all.

S

Google is a tool, common sense is a usefull tool, too. The first result is 2,4-dinitrophenol, the second is about 2,4-dinitro phenyl hydrazine and the heading of the third is "addition-elimination reactions of aldehydes and ketones".