[a confused chiral girl]

I'm wondering how I can draw the steps for these 2 compounds (sorry for my ugly drawings  ) from cyclopentanone , D₂O, using any organic/inorganic reagents....and how many steps would it take?

thank you SO MUCH!! 

[Custos]

This is a question about keto-enol tautomerism, reduction of carbonyls and hydrogenation.
a) Because of the tautomerism you can easily get duteriums in the positions next to the carbonyl using just D2O and a trace of base (eg. potassium carbonate). Then reduce the carbonyl with sodium borohydride - locking the H into position (no more keto-enol tautomerism). Finally treat with D2O again to convert the alcohol to -OD.

For the second question you need to reduce the carbonyl from part (a) using sodium boroduteride (not hydride) to put deuteriums everywhere - then eliminate water (strictly you're eliminating D2O) using base. The to put in the final two hydrogens you can use hydrogenation of the double bond with hydrogen gas and a catalyst like palladium...

Here, a picture might help