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Topic: cyclohexanone and amino aldehyde reaction  (Read 673 times)

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Offline leynasolomon

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cyclohexanone and amino aldehyde reaction
« 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!

Offline Meter

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Re: cyclohexanone and amino aldehyde reaction
« Reply #1 on: May 11, 2021, 11:08:54 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!
This is vague. Please draw the molecules you are referring to.

Offline leynasolomon

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Re: cyclohexanone and amino aldehyde reaction
« Reply #2 on: May 11, 2021, 11:15:33 AM »
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?

Offline Meter

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Re: cyclohexanone and amino aldehyde reaction
« Reply #3 on: May 11, 2021, 11:34:35 AM »
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.

Offline leynasolomon

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Re: cyclohexanone and amino aldehyde reaction
« Reply #4 on: May 11, 2021, 11:45:54 AM »
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.


Offline Meter

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Re: cyclohexanone and amino aldehyde reaction
« Reply #5 on: May 11, 2021, 12:09:56 PM »
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.

Offline leynasolomon

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Re: cyclohexanone and amino aldehyde reaction
« Reply #6 on: May 11, 2021, 12:12:52 PM »
Yes I thought it would be an imine do u know which imine I would get?

Offline Meter

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Re: cyclohexanone and amino aldehyde reaction
« Reply #7 on: May 11, 2021, 12:15:53 PM »
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.

Offline Meter

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Re: cyclohexanone and amino aldehyde reaction
« Reply #8 on: May 11, 2021, 12:16:01 PM »
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.

Offline leynasolomon

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Re: cyclohexanone and amino aldehyde reaction
« Reply #9 on: May 11, 2021, 12:27:12 PM »
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.

Offline rolnor

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Re: cyclohexanone and amino aldehyde reaction
« Reply #10 on: May 11, 2021, 01:45:31 PM »
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!

Offline OrganicH2O

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Re: cyclohexanone and amino aldehyde reaction
« Reply #11 on: May 15, 2021, 03:04:40 PM »
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 have a Master's in organic chemistry and I am exposed to a LOT of different introductory organic chem classes in the course of my work, ranging from very basic to Harvard. I am here to refine my knowledge and consult with other organic chemistry nerds.

Offline OrganicH2O

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Re: cyclohexanone and amino aldehyde reaction
« Reply #12 on: May 15, 2021, 03:11:46 PM »
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.
I have a Master's in organic chemistry and I am exposed to a LOT of different introductory organic chem classes in the course of my work, ranging from very basic to Harvard. I am here to refine my knowledge and consult with other organic chemistry nerds.

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