[hobobot]

I know you can convert an R-CN group to an acid using H+, H2O and heat. But, what happens when you try to do that reaction in a base?  I got as far as having a R-C(OH)NH group. Not sure if it can go farther than that.

[408]

You have an acidic proton in your basic reaction... It can go further...

[AC Prabakar]

Yes u r right.Hydrolysis"-CN" in basic medium proceeds via amide intermediate.You can find this in any basic organic chemistry book.
Hydrolysis sequence is as follows.
"-CN"----(fast)--->amide--(slow)----->acid.

In order to make "-NH2" of amide intermediate as leaving group,we should use strong base such as KOH/NaOH etc.
If u r continuing the reaction you can end up in acid.(After acidification only u will get acid!in basic medium it will be as carboxylate anion.)

[hobobot]

thanks! that does make sense. I didn't know that the amide->acid was the slow step. That's really helpful.