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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: hpl912 on November 10, 2009, 09:18:16 PM

Title: brominations at both ends of a 6 carbon chain ?
Post by: hpl912 on November 10, 2009, 09:18:16 PM

I don't get by which method i can successfully obtain Br-(CH2)6-Br from CH3-(CH2)4-CH3

I was thinking by using Br2 with heat but that doesn't seem to double brominate the chain at both ends but i think it only brominates at one end and still it's a minor product (tends to attach only to the most substituted carbon)

i'm out of ideas now  :-\

Title: Re: brominations at both ends of a 6 carbon chain ?
Post by: darkness1102 on November 10, 2009, 10:03:41 PM

You should start from phenol (C₆H₅OH)
C₆H₅OH + H₂/Ni --> C₆H₁₁OH  --t^o--> C₆H₁₀ --( O₃/H₂O)--> OHC-(CH₂)₄-CHO -( LiAlH₄)--> HO-CH₂-(CH₂)₄-CH₂-OH --(HBr)-->
Br-(CH₂)₆-Br

Title: Re: brominations at both ends of a 6 carbon chain ?
Post by: hpl912 on November 11, 2009, 08:41:50 PM

thanks but the starting material has to be CH3-(CH2)4-CH3  :-\