Due to the acidic nature of α hydrogens they can be exchanged with deuterium by reaction with D2O (heavy water). The process is accelerated by the addition of an acid or base; an excess of D2O is required. The end result is the complete exchange of all α hydrogens with deuterium.
Mechanism in basic conditions
Step 1: Enolate Formation
Step 2: Deuteration
Please draw the product for the following reactions.