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

by James

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{ 12 comments… read them below or add one }

Rajarshi Banerjee

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

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Emm

It can especially if the R is aromatic.

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Jared Hensley

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

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James

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.

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Alanckrit

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)

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James

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

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Jerry

I remember that imine salt will generate after nitrile reacts with grignard reagent. Is it possible two equiv of grignard and one equiv of nitrile form the imine salt like R2C-N(MgX)2 ?? Could the negative charges on nitrogen be stabilized by magnesium cation ??

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Gauri

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

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Gauri

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

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Manjoorahmed

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

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Alyssa

I thought N don’t usually leave?

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James

If it’s protonated, it will.

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