Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: leynasolomon on May 11, 2021, 11:03:40 AM
-
I'm trying to produce a compound with the chemical formula C10H13N from cyclohexanone by reacting it with a primary amine. However my primary amine has an aldehyde group and I don't know how to remove this oxygen to get the formula C10H13N. I'm using H3O+ as a reagent so perhaps this can dehydrate the aldehyde group?
Can anyone help with this!
-
I'm trying to produce a compound with the chemical formula C10H13N from cyclohexanone by reacting it with a primary amine. However my primary amine has an aldehyde group and I don't know how to remove this oxygen to get the formula C10H13N. I'm using H3O+ as a reagent so perhaps this can dehydrate the aldehyde group?
Can anyone help with this!
This is vague. Please draw the molecules you are referring to.
-
Sorry for being vague. I'm basically reacting cyclohexanone with 3-Amino-2-methylacrylaldehyde and a hydronium ion. Do you know what structure this would form?
-
Sorry for being vague. I'm basically reacting cyclohexanone with 3-Amino-2-methylacrylaldehyde and a hydronium ion. Do you know what structure this would form?
So that molecule is actually an enamine. Reacting a ketone with a primary amine under acidic conditions would result in an imine, but I'm not sure it's that simple with primary enamines. And in this molecule, the lone pair on the nitrogen is already delocalized, so it is not clear feasible that reaction would be.
Might wanna wait around for someone more experienced to give you a more fulfilling answer.
-
Hey thanks for the quick reply. Are you sure its an examine?
I've attached an image below of the reaction I am looking at. I just cannot determine what the product would be from this.
-
No, I got my wires crossed. Sorry.
However, the double bond next to the nitrogen allows for various resonance forms that might affect its nucleophilicity. Otherwise, I think you would just get an imine since that's the characteristic product between a primary amine and a ketone under acidic conditions.
-
Yes I thought it would be an imine do u know which imine I would get?
-
Yes I thought it would be an imine do u know which imine I would get?
The one where the nitrogen forms a C=N bond with the carbonyl on cyclohexanone. Cyclization is not possible with this molecule, i.e. it will not intramolecularly react with the aldehyde.
-
Yes I thought it would be an imine do u know which imine I would get?
The one where the nitrogen forms a C=N bond with the carbonyl on cyclohexanone. Cyclization is not possible with this molecule, i.e. it will not intramolecularly react with the aldehyde.
-
Thanks. I've made an imine with the C=N bond where the C=O bond once was however this still doesn't match with the formula as there is still an aldehyde group and too many hydrogens.
-
The amino aldehyde you draw is completely impossible in several ways. You need to check out the properties of enamines, imines, ketones and aldehydes. You lack basic skills in organic chemistry and need to study more before attempting reactions on this level. Also its a good thing to do literature search first before doing any thing practical in the lab (accept cleaning equipment).
Good luck!
-
The amino aldehyde you draw is completely impossible in several ways. You need to check out the properties of enamines, imines, ketones and aldehydes. You lack basic skills in organic chemistry and need to study more before attempting reactions on this level. Also its a good thing to do literature search first before doing any thing practical in the lab (accept cleaning equipment).
Good luck!
Isn't that enamine a vinylogous amide, and therefore unusually stable compared to other enamines? I'm not an expert on this topic, but I can see it is not a traditional enamine or aldehyde. At least some molecules like this are stable enough to isolate.
-
I just sketched something out that seems reasonable. But I'm not supposed to just give you the answer. Perhaps a hint: Imine formation followed by intramolecular aldol process to make an aromatic ring. Enamines can be a nucleophile for aldol...
Just to edit: I don't know for sure whether the aldol or imine formation happens first. But either way, you get the same answer.