What Is the Product of Treating 1,1,4,4-Tetra D Cyclohexane with SO2Cl2?

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SUMMARY

The reaction of 1,1,4,4-tetra D cyclohexane with SO2Cl2 results in chlorination, where chlorine replaces either deuterium (D) or hydrogen (H) atoms. The presence of peroxide facilitates free radical chlorination, which is a well-established reaction mechanism with SOCl2. The discussion highlights that there are 12 potential chlorination sites, with 4 being deuterated, and raises questions about the impact of hydrogen mass on radical stability. Understanding these factors is crucial for predicting the reaction outcomes.

PREREQUISITES
  • Knowledge of free radical chlorination mechanisms
  • Understanding of deuterated compounds and their reactivity
  • Familiarity with SO2Cl2 (thionyl chloride) as a chlorinating agent
  • Basic principles of radical stability and reaction conditions
NEXT STEPS
  • Study the mechanism of free radical chlorination in detail
  • Research the effects of isotopic substitution on reaction pathways
  • Explore the stability of secondary radicals in organic chemistry
  • Investigate the role of peroxide in radical reactions
USEFUL FOR

Chemistry students, organic chemists, and researchers interested in reaction mechanisms and chlorination processes.

Sourabh N
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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)
 
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What are the conditions. Heat, light or peroxide?
 
Sorry for that. Peroxide is present.
 
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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