Cycloalkene Chlorination w/ Dichloromethane?

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In summary, the conversation discusses a homework problem involving a reaction between cyclopentane and chlorine in the presence of dichloromethane. The equations and attempts at a solution are also mentioned, with the conclusion that there is most likely no reaction due to the lack of a radical initiator.
  • #1
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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  • #2
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.
 

1. What is the purpose of using dichloromethane in cycloalkene chlorination?

Dichloromethane, also known as methylene chloride, is commonly used as a solvent in organic chemistry reactions because it is a nonpolar solvent that can dissolve a wide variety of organic compounds. In cycloalkene chlorination reactions, it is used to dissolve the cycloalkene and the chlorine gas, allowing them to react more easily.

2. How does dichloromethane facilitate the cycloalkene chlorination reaction?

Dichloromethane has a higher boiling point than most other common organic solvents, making it easier to maintain the reaction at a specific temperature. Additionally, it is less reactive than other chlorinated solvents, reducing the chance of side reactions occurring during the chlorination process.

3. Is dichloromethane safe to use in cycloalkene chlorination?

Like any chemical, dichloromethane can be hazardous if not handled properly. It is important to follow proper safety precautions, such as using gloves and safety glasses, when working with this solvent. It is also important to dispose of it properly after use.

4. Can other solvents be used in cycloalkene chlorination instead of dichloromethane?

Yes, other solvents such as chloroform or carbon tetrachloride can also be used in cycloalkene chlorination reactions. However, they may have different effects on the reaction and may not be as effective as dichloromethane.

5. Are there any limitations to using dichloromethane in cycloalkene chlorination?

Dichloromethane may not be suitable for all cycloalkene chlorination reactions. For example, if the cycloalkene contains a double bond, it may react with dichloromethane instead of the chlorine gas, leading to undesired products. In these cases, a different solvent or method may need to be used.

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