[amanda]

My question is about deuterium exchange at the alpha hydrogen of the ester. From what I know about the hydrolysis mechanism using HCl and D20 as the acid catalyzed hydrolysis this would exchange all of the ester functions with a carboxylic acid but it would be C00D instead of C00H. My issue is that if you have alpha hydrogens in the ester wouldnt they be exchanged with the deuterium as well?

[movies]

They would exchange eventually, but the rate is probably a lot slower.

[FeLiXe]

in alkaline conditions you could probably exchange the alpha protons