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Author Topic: Synthesis of 2-butene-1-ol from 1-bromopropane  (Read 759 times)

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scotchtape21

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Synthesis of 2-butene-1-ol from 1-bromopropane
« on: December 09, 2012, 03:03:25 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?
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orgopete

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #1 on: December 09, 2012, 07:35:00 PM »

This looks like acetylene chemistry and formaldehyde as a one carbon fragment.
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Dan

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #2 on: December 09, 2012, 09:21:05 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?

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

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #3 on: December 10, 2012, 05:51:59 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?
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discodermolide

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #4 on: December 10, 2012, 05:59:04 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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Borek

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #5 on: December 10, 2012, 06:15:34 AM »

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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scotchtape21

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #6 on: December 10, 2012, 07:23:59 AM »

I attached an image.
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discodermolide

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #7 on: December 10, 2012, 07:45:12 AM »

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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scotchtape21

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #8 on: December 10, 2012, 10:23:32 AM »

T-butyl is tert-butyl or really any tertiarty butyl molecule. And you get an aldehyde through ozonolysis using O3/dimethylsulfide.
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discodermolide

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Re: Synthesis of 2-butene-1-ol from 1-bromopropane
« Reply #9 on: December 10, 2012, 07:38:10 PM »

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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