Wollf-Kishner

[SaintJude]

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Ok, looked at the AAMC topic orgo list and saw that they were testing for Wolf-Kishner and I just find this rx weird.

It reduced a carbonyl to a CH2 group. If there was a discrete asking for the intermediate, would not have realized that it is a hydrazone

Kaplan says: Note rx is useful only when the product is stable under basic conditions. Doesn't the product always forms an alkane? What's the big concern?

 

[chiddler]

Ok, looked at the AAMC topic orgo list and saw that they were testing for Wolf-Kishner and I just find this rx weird.

It reduced a carbonyl to a CH2 group. If there was a discrete asking for the intermediate, would not have realized that it is a hydrazone

Kaplan says: Note rx is useful only when the product is stable under basic conditions. Doesn't the product always forms an alkane? What's the big concern?

pretty much all carbonyl + amines (hydrazines resemble amines, anyway) ends up with a hydrozone. except if the amine is secondary.

i'm not sure about your specific question, though. perhaps if it contains some other funtional group that is reactive in base, like an iodine somewhere? then you'll get elim and the wrong product.

 

[hellocubed]

Kaplan says: Note rx is useful only when the product is stable under basic conditions. Doesn't the product always forms an alkane? What's the big concern?

I am not sure about this, so any additional input would be appreciated.

Amine in an acidic reaction becomes protonated, and hence no longer have the nucleophilic strength to perform the reaction.