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Topic: Synthesis of 2-butene-1-ol from 1-bromopropane  (Read 4045 times)

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Offline scotchtape21

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Synthesis of 2-butene-1-ol from 1-bromopropane
« on: December 09, 2012, 09:03:25 PM »
How can you synthesize 2-butene-1-ol from 1-bromopropane?
Please show all reagents used and molecules made along the way.
How do you get from 3 carbons to 4?

Offline orgopete

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #1 on: December 10, 2012, 01:35:00 AM »
This looks like acetylene chemistry and formaldehyde as a one carbon fragment.
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Offline Dan

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #2 on: December 10, 2012, 03:21:05 AM »
How can you synthesize 2-butene-1-ol from 1-bromopropane?
Please show all reagents used and molecules made along the way.
How do you get from 3 carbons to 4?

You must demonstrate that you have attempted the question, this is a forum rule - please read them.
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Offline scotchtape21

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #3 on: December 10, 2012, 11:51:59 AM »
So far I have:
1-bromopropane (/\Br) +Mg---> /\MgBr + epoxide + h2/h2o ---> OH/\/\/ + PBr3---> /\/\/Br
/\/\/Br + t-butyl---> /\/\\ +O3/DMS ---> /\/\\O

I don't know where to go from there. I think I have to make an allene?

Offline discodermolide

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #4 on: December 10, 2012, 11:59:04 AM »
What is the structure of that last compound in the chain?
You reaction scheme is very difficult to follow. Which epoxide are you using?
It would be better if you drew the actual molecules out.
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Offline Borek

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #5 on: December 10, 2012, 12:15:34 PM »
1-bromopropane (/\Br) +Mg---> /\MgBr + epoxide + h2/h2o ---> OH/\/\/ + PBr3---> /\/\/Br
/\/\/Br + t-butyl---> /\/\\ +O3/DMS ---> /\/\\O

Note you can use SMILES for structural formulas, as described here:

CCCBr.[Mg]>>CCC[Mg]Br
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Offline scotchtape21

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #6 on: December 10, 2012, 01:23:59 PM »
I attached an image.

Offline discodermolide

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #7 on: December 10, 2012, 01:45:12 PM »
Two questions, 1, what is tButyl?, 2, how are you going to get the C=C into that aldehyde? Any ideas?
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Offline scotchtape21

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #8 on: December 10, 2012, 04:23:32 PM »
T-butyl is tert-butyl or really any tertiarty butyl molecule. And you get an aldehyde through ozonolysis using O3/dimethylsulfide.

Offline discodermolide

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #9 on: December 11, 2012, 01:38:10 AM »
T-butyl is tert-butyl or really any tertiarty butyl molecule. And you get an aldehyde through ozonolysis using O3/dimethylsulfide.


Any tertiary butyl molecule? You will have to be more specific.
I know you get an aldehyde that way. I was referring to the C=C you need to generate to get your desired molecule.
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