Addition of Grignard reagents to nitriles to give ketones (after hydrolysis)

by James

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{ 11 comments… read them below or add one }

Rajarshi Banerjee October 29, 2012 at 12:07 pm

If I do not add acid will the reaction stop at imines


Emm May 9, 2013 at 5:21 am

It can especially if the R is aromatic.


Jared Hensley February 21, 2014 at 3:57 pm

why can you not attack a second time with another equiv of grignard? thanks!


James February 25, 2014 at 2:04 pm

The problem is that you’d essentially have a nitrogen with two negative charges on it – very unstable. So it tends to simply do mono-addition.


Alanckrit May 23, 2014 at 12:13 pm

no i think JARED is asking about why not the ketone formed further react with grignard reagent to give 3 degree alcohol….if it does is it a negative aspect of this reaction?? (if we wanted to get ketone)


James May 26, 2014 at 3:37 pm

The ketone isn’t formed until adding water, which would destroy any Grignard that is present.


Gauri May 30, 2014 at 8:59 pm

In case of HCN will the same reaction happen or will the H be removed and we will get CH4 and NCMgBr?


Gauri May 30, 2014 at 9:56 pm

Will the same reactin happen with HCN or will we get CH4 and CH3MgBr like an alkane reaction?


Manjoorahmed September 19, 2014 at 5:45 am

Is that possible that alkyl cynide react with two moles of grignard reagent to give alkyl amine?


Alyssa November 11, 2015 at 12:20 am

I thought N don’t usually leave?


James November 20, 2015 at 1:26 am

If it’s protonated, it will.


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