What happens when the above compound is subjected to DCl in MeOD? As a result of tautomerism, I'd expect at least 7H atoms, two alpha to carbonyl carbon (right side), and five at gamma position (two on one position and three on the other); to be replaced with deuterium.
However, I'm not clear about the mechanism that'd be followed to achieve the same. And at the same time I'm not sure if there will be an 8'th replacement at alpha position to the carbonyl carbon (left side).
I know that the hydrogens on the right alpha position is replaced due to enolization and I think I got the mechanism for this, but the rest is a blank for me at the moment.
If someone could please help provide a detailed mechanism, it'd be really helpful. Thanks a lot.