… Found it in Carboxylic acids and nitriles chapter. The book says we should 2 eq. of ch3mgbr and h30+ to benzonitrile.
I would have treated the nitrile with HCl and ethanol to go directly to an ester. Addition of two equivalents of Grignard will result in a tertiary alcohol after neutralization. In my book, I have the addition to a nitrile stopping at the imine, hydrolysis give a ketone. If repeated, the product is as indicated. If the reaction were to go as described, the product should be an amine.
The reason this reaction doesn't add twice is that the second addition places a very high charge density on the nitrogen with a formal minus 2 charge. Neutralization should leave an amine as product (no C-N bond cleavage).
Can someone give me a reference for this double addition?