Sodium metal reduction of chloroform In discussing how best to deuterate chloroform, it occurred to me that we could use sodium metal to reduce hydrogen into hydrogen gas. If this could actually happen, this would be a great thing - we wouldn't have much if any residual hydrogen in the liquid phase of the system after treatment. 

Is this possible? I had a possible mechanism in mind.



The problems I foresee are:

1) Won't reduction of chlorine to chlorine gas be a competitive, side reaction? From this page (http://en.wikipedia.org/wiki/Standard_electrode_potential_(data_page)) I see that the reduction potential for chloride ion to to chlorine gas is -1.36 V (unfavorable) and reduction of hydride ion to hydrogen gas is a +2.23 V (favorable). Am I interpreting and applying the data correctly? 

2) What happens to the $\ce{CCl_3}$ radicals after hydrogen is reduced? Is dimerization going to occur to a large extent? 

3) How then do we introduce deuterium and effectively incorporate it with $\ce{CCl_3}$ radicals?
Sodium + Chloroform:
https://www.youtube.com/watch?v=du3ksrfnCcg

To prepare deuterochloroform I'd recommend the haloform reaction.