[Unco]

If I want to monitor the formation of the enolate after adding a strong base to the alpha saturated ketone, is there a way to visualize it on TLC? As in a way such that the enol form won't get turn back to its keto form on the TLC since silica is acidic. If not, is there another way to tell if I am forming the enolate quantitatively in the reaction vessel?

[discodermolide]

Well TLC won't work here. The best way is to remove a sample and add D₂O or some other deuteration agent. Work it up and get an NMR of your deuterated starting material. You should see only a 2H signal corresponding to alpha protons instead of a 3H integral, if its gone 100%.

[Unco]

cool, maybe i will try that