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Topic: brominations at both ends of a 6 carbon chain ?  (Read 2731 times)

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Offline hpl912

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brominations at both ends of a 6 carbon chain ?
« 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  :-\
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Offline darkness1102

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Re: brominations at both ends of a 6 carbon chain ?
« Reply #1 on: November 10, 2009, 10:03:41 PM »
You should start from phenol (C6H5OH)
C6H5OH + H2/Ni --> C6H11OH  --to--> C6H10 --( O3/H2O)--> OHC-(CH2)4-CHO -( LiAlH4)--> HO-CH2-(CH2)4-CH2-OH --(HBr)-->
Br-(CH2)6-Br
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Offline hpl912

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Re: brominations at both ends of a 6 carbon chain ?
« Reply #2 on: November 11, 2009, 08:41:50 PM »
thanks but the starting material has to be CH3-(CH2)4-CH3  :-\
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