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

  • Thread starter Simfish
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  • #1
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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Answers and Replies

  • #2
Simfish
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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).
 
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  • #3
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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).
 
  • #4
chemisttree
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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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