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chemistry organic a level help

Draw the structure of a primary amine with four carbon atoms that cannot be formed from a nitrile.

i dont know how to work this out
I don’t want to give you the answer straight away so.....what have you come up with so far & I’ll try to help!
Original post by Ensoetre
I don’t want to give you the answer straight away so.....what have you come up with so far & I’ll try to help!

basically i understand that nitriles can be reduced to primary amines with nickel and hydrogen catalyst but i have no idea when this wouldn't be possible, normally i can work it out but this has me clueless
Original post by onedance1
basically i understand that nitriles can be reduced to primary amines with nickel and hydrogen catalyst but i have no idea when this wouldn't be possible, normally i can work it out but this has me clueless

It’s quite difficult to explain without a diagram but it’s simple! Basically you need to have a primary amine that contains a methyl group on C1 ( C-NH2 ). These can’t be formed from a nitrile because CN is reduced to ( RCH2NH2 ). If you have a methyl on the C1 in the primary amine it can’t be formed from a nitrile. Try to draw out what I’m saying it will make sense.
Work backwards. Draw the amine first & then try to draw the nitrile and you’ll see you can’t do it

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