[Urbanium]

How likely it is a H/D exchange will take place in a basic aqueous solution if the dissolved deuterated compound contains deuteriums only at alkyl groups (i.e. -CD₃, -CD₂-, -CD--)? I'm familiar with exchange at -OH and -NH groups, but does that occur with deuterated alkyl groups?

[Babcock_Hall]

Is there a functional group next to the carbon in question?

[Urbanium]

Is there a functional group next to the carbon in question?

There are hydroxyl groups only, more precisely a --CD-OH  and also one -CD₂-OH further away.

[Babcock_Hall]

When a ketone group is in the alpha position relative to a -CH_x group of some kind, basic exchange is expected.  Do you think that a hydroxyl group would have the same effect?  Why or why not?

[hollytara]

Carbonyls can undergo acid catalyzed exchange too. 

What is the pKa of the protons next to a hydroxyl?