[science123]

I need help on getting started on this reaction.

[Arctic-Nation]

I'm not sure what is meant with the arrow-square thingy, but this reaction has two steps: introduction of the methyl groups and hydrolysis of the nitrile function. I'll let you work out what comes first.

[science123]

I'm not sure what is meant with the arrow-square thingy, but this reaction has two steps: introduction of the methyl groups and hydrolysis of the nitrile function. I'll let you work out what comes first.

The square box is to write the reagents/steps for the reaction. I was looking for this reaction in aromatics section but couldn't find it. Found it in Carboxylic acids and nitriles chapter. The book says we should 2 eq. of ch3mgbr and h30+ to benzonitrile.

[Arctic-Nation]

Exactly what I had in mind. Good search.

[orgopete]

… 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?

[Arctic-Nation]

Ah, crud. I'm really out of shape. Of course you're right. Sorry.

Of course, a two-step route (from nitrile to ketone to alcohol) is also possible, though probably not better than the ester route.