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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: sharbeldam on June 18, 2020, 02:53:47 PM

Title: Wolff Kishner?
Post by: sharbeldam on June 18, 2020, 02:53:47 PM

Can it reduce ketones that have functional groups in their chain? for instance if there is an amine involvled.
let's say 4-amino-2-pentanone.

are there specific rules for this reaction?

Thank you

Title: Re: Wolff Kishner?
Post by: rolnor on June 19, 2020, 06:59:32 AM

What would you say about amino groups and ketone-carbonyl groups, can they react with each other in some way?

Title: Re: Wolff Kishner?
Post by: sharbeldam on June 19, 2020, 09:14:53 AM

Yes to produce amines and enamines, but in general if there was a functional group that doesnt react with the ketone, can we do the wolff kishner or does it have to be alkyl?

Title: Re: Wolff Kishner?
Post by: rolnor on June 20, 2020, 03:27:36 AM

You use hydrazine fot this, a very strong nucleophile so this will be difficult with electrophilic groups on the molecule.
You can also make a dithioacetal from the ketone/aldehyde and use Raney-Ni to de-sulphurize it, this will give the same result as Wold-Kischner and you avoid strong nucleophile. https://en.wikipedia.org/wiki/Thioacetal
https://en.wikipedia.org/wiki/Raney_nickel