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

by James

Content available for Reactionguide members only. Not a member? Get access for about 30 cents / day!

{ 9 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

Reply

Emm May 9, 2013 at 5:21 am

It can especially if the R is aromatic.

Reply

Jared Hensley February 21, 2014 at 3:57 pm

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

Reply

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.

Reply

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)

Reply

James May 26, 2014 at 3:37 pm

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

Reply

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?

Reply

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?

Reply

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?

Reply

Leave a Comment