Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Ayushmaan on October 31, 2017, 02:22:58 PM
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What's the reaction mechanism when formaldehyde reacts with hydroxylamine??
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Please read the forum rules (http://www.chemicalforums.com/index.php?topic=65859.0). You have to show your attempts at answering the question to receive help.
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Alright, now can you please help me Figure out the mechanism???
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Can you say which one is electrophile and nucleophile Ayushmaan?
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I predicted the mechanism like this.
Lone pair on in formaldehyde double bond with oxygen is rearranged as lone pair shifts on oxygen and oxygen acquires negative charge.
Then the nitrogen on H3NO attacks the positively charged carbon of formaldehyde.
This is how i attempted it.
If it's incorrect please let me know what's the correct one.
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Well i am not sure rolnor but i do know that final product is oxime :P
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I predicted the mechanism like this.
Lone pair on in formaldehyde double bond with oxygen is rearranged as lone pair shifts on oxygen and oxygen acquires negative charge.
Then the nitrogen on H3NO attacks the positively charged carbon of formaldehyde.
This is how i attempted it.
If it's incorrect please let me know what's the correct one.
What about a concerted attack on C=O, by the lone pair on N? If your final product is an oxime, how will you encourage the oxygen atom from formaldehyde to leave?
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I agree with you babcock_hall
So what should be the final mechanism?
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You are required by the forum rules to show your attempt before we can help you. I think that the next step might involve proton transfer. Try drawing as much of the mechanism as you can.
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I tried but it im still confused about the last step
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Please show what you have, and we can help you from there.
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I figured it out
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Never mind