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

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Discussion Overview

The discussion revolves around the chemical reaction of 1,1,4,4-tetra D cyclohexane when treated with SO2Cl2, focusing on the potential products and the mechanisms involved in the chlorination process.

Discussion Character

  • Homework-related
  • Exploratory
  • Technical explanation

Main Points Raised

  • One participant expresses confusion about whether chlorine will replace deuterium (D) or hydrogen (H) in the reaction.
  • Another participant inquires about the conditions necessary for the reaction, specifically asking if heat, light, or peroxide is required.
  • A subsequent post clarifies that peroxide is present in the reaction conditions.
  • Another participant notes that free radical chlorination is a known reaction with SOCl2 and mentions that there are 12 positions available for chlorination, including 4 that are deuterated.
  • This participant questions the implications of doubling the mass of hydrogen on the reaction and the stability of a second-degree radical.

Areas of Agreement / Disagreement

Participants do not reach a consensus on the specifics of the reaction outcomes, and multiple viewpoints regarding the chlorination process and its implications remain present.

Contextual Notes

There are unresolved aspects regarding the assumptions about the reaction mechanisms and the effects of substituents on the stability of radicals. The discussion does not clarify the impact of the presence of deuterium versus hydrogen in the chlorination process.

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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