organic chemistry problem

[Sourabh N]

1. The problem statement, all variables and given/known data
What is the product when 1,1,4,4-tetra D cyclohexane
is treated with SO2Cl2






3. The attempt at a solution

I'm confused whether Cl will replace D or H (it must replace any one of them)

[chemisttree]

What are the conditions. Heat, light or peroxide?

[Sourabh N]

Sorry for that. Peroxide is present.

[chemisttree]

free radical chlorination is a well known reaction with SOCl2. There are 12 positions that can be chlorinated, 4 of them are deuterated. What effect would doubling the mass of the hydrogen have on the reaction? What effect would doubling the mass of a hydrogen have on the stability of a 2nd degree radical?