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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: scotchtape21 on December 09, 2012, 09:03:25 PM

Title: Synthesis of 2-butene-1-ol from 1-bromopropane
Post by: scotchtape21 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?
Title: Re: Synthesis of 2-butene-1-ol from 1-bromopropane
Post by: orgopete on December 10, 2012, 01:35:00 AM
This looks like acetylene chemistry and formaldehyde as a one carbon fragment.
Title: Re: Synthesis of 2-butene-1-ol from 1-bromopropane
Post by: Dan 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.
Title: Re: Synthesis of 2-butene-1-ol from 1-bromopropane
Post by: scotchtape21 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?
Title: Re: Synthesis of 2-butene-1-ol from 1-bromopropane
Post by: discodermolide 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.
Title: Re: Synthesis of 2-butene-1-ol from 1-bromopropane
Post by: Borek 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 (http://www.chemicalforums.com/index.php?topic=59314.msg230001#msg230001):

CCCBr.[Mg]>>CCC[Mg]Br
Title: Re: Synthesis of 2-butene-1-ol from 1-bromopropane
Post by: scotchtape21 on December 10, 2012, 01:23:59 PM
I attached an image.
Title: Re: Synthesis of 2-butene-1-ol from 1-bromopropane
Post by: discodermolide 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?
Title: Re: Synthesis of 2-butene-1-ol from 1-bromopropane
Post by: scotchtape21 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.
Title: Re: Synthesis of 2-butene-1-ol from 1-bromopropane
Post by: discodermolide 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.