[Cooper]

Hi,

In my screenshot below I was wondering what the mechanism is for the last step when the complex is hydrolyzed. I am thinking that the hydronium ion donates a proton to the nitrogen, then water attacks the carbon of the nitrile, moving a lone pair to the nitrogen. But then what happens?

Thanks

[discodermolide]

How about this pathway?

[Cooper]

How about this pathway?

So the nitrogen gets all 3 protons from hydronium one after another?

[discodermolide]

Looks like it, certainly ammonia is released during this process.
Anyway that is my suggestion for the formation of the ketone.

[Cooper]

Great thanks That's along the lines that I was thinking but I wasn't sure.

[Dan]

See also:

http://www.curvedarrowpress.com/partd/iminehydrolysis.html

[Cooper]

See also:

http://www.curvedarrowpress.com/partd/iminehydrolysis.html

Wonderful, thanks