Organic chemistry problem

  • #1

Sourabh N

631
0

Homework Statement


What is the product when 1,1,4,4-tetra D cyclohexane
is treated with SO2Cl2






The Attempt at a Solution



I'm confused whether Cl will replace D or H (it must replace anyone of them)
 
  • #2
What are the conditions. Heat, light or peroxide?
 
  • #3
Sorry for that. Peroxide is present.
 
  • #4
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?
 

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