How do you knock off a halogen from a hydrocarbon chain?

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SUMMARY

The discussion focuses on the process of removing a halogen from a hydrocarbon chain without introducing other atoms or double bonds. The method involves dehydrohalogenation, which eliminates the halogen and forms a double bond between adjacent carbon atoms. This double bond can then be reduced to a single bond through catalytic hydrogenation using high-pressure hydrogen (H2) and a transition metal catalyst such as nickel (Ni), palladium (Pd), platinum (Pt), or rhodium (Rh). An alternative method involves treating the compound with sodium (Na), potassium (K), or lithium (Li) followed by a workup with water.

PREREQUISITES
  • Understanding of dehydrohalogenation reactions
  • Knowledge of catalytic hydrogenation techniques
  • Familiarity with transition metals used as catalysts
  • Basic principles of hydrocarbon chemistry
NEXT STEPS
  • Research the mechanisms of dehydrohalogenation reactions
  • Learn about catalytic hydrogenation and the role of transition metals
  • Explore alternative methods for reducing double bonds in hydrocarbons
  • Investigate the use of sodium, potassium, or lithium in organic synthesis
USEFUL FOR

Chemists, organic synthesis researchers, and students studying hydrocarbon reactions will benefit from this discussion, particularly those interested in halogen removal techniques and hydrogenation processes.

Simfish
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Without introducing any other atoms or double bonds into the chain? (just replace the halogen with a hydrogen atom). Assume for now that the halogen was introduced in the middle of the carbon chain.
 
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Okay I think I solved it.

Dehydrohalogenation removes the halogen and the attached carbon forms a double bond with another carbon. But then hydrogenation of this double bond into a single bond is spontaneous (it just needs a catalyst to speed up).
 
Last edited:
Pretty much. Yes, it's going to be two separate reactions. Next, you need to reduce the double bond somehow, as by catalytic hydrogenation: i.e., high pressure H2 + a suitable transition metal (Ni, Pd, Pt, Rh, etc).
 
That's one way. Another is to treat with Na or K or Li and work up with water. Your way is better for large quantities.
 

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