Cycloalkene Chlorination w/ Dichloromethane?

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SUMMARY

The discussion centers on the chlorination of cyclopentane using chlorine in the presence of dichloromethane (DCM). It concludes that no significant reaction occurs because DCM serves only as a solvent and lacks a radical initiator necessary for the chlorination of alkanes. The participants reference prior knowledge of alkane chlorination requiring heat or light and the halogenation of alkenes, but confirm that cycloalkanes do not react under these conditions without additional energy input.

PREREQUISITES
  • Understanding of alkane chlorination mechanisms
  • Familiarity with radical initiators in organic reactions
  • Knowledge of dichloromethane as a solvent
  • Basic principles of halogenation reactions
NEXT STEPS
  • Research the role of radical initiators in alkane chlorination
  • Study the mechanisms of halogenation reactions involving alkenes and alkynes
  • Explore alternative methods for converting alkanes to alkenes
  • Investigate the properties and applications of dichloromethane in organic synthesis
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Chemistry students, organic chemists, and anyone studying reaction mechanisms involving alkanes and halogenation processes.

tycon69
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Homework Statement



I am currently working on a homework assignment in Bruice Organic Chemistry and have ran across a problem that I can't find an answer to anywhere. It is simply a reaction between cyclopentane and chlorine in the presence of dichloromethane.

Homework Equations



This is in the same chapter that we are looking at reactions such as alkane chlorination with heat or light, and NBS reactions to alkenes. The book doesn't, however, say anything about this reaction between chlorine and a cycloalkane in the presence of DCM. We have, in previous chapters, looked at halogenation of alkene and alkynes in the presence of DCM, but never an alkane or cycloalkane.
I checked all over the internet and cannot find anything except a few things saying alkanes will only react through halogenation with energy, and combustion, although I myself remember seeing a reaction or two that made alkenes from alkanes.

The Attempt at a Solution



If I had to guess, I would say that It would break the chain and add Cl to each side, although this is merely a guess and is not supported by any evidence. It could also behave similar to hydrogenation with energy present.

Anyways thanks for your help,
Tycon69
 
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I'm fairly sure there is no reaction. Dichloromethane simply acts as a solvent here, and nothing else is present to act as a radical initiator.
 

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