March 28, 2024, 11:24:09 AM
Forum Rules: Read This Before Posting


Topic: Synthesis of 2-butene-1-ol from 1-bromopropane  (Read 3717 times)

0 Members and 1 Guest are viewing this topic.

Offline scotchtape21

  • New Member
  • **
  • Posts: 4
  • Mole Snacks: +0/-0
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

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
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.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline Dan

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 4716
  • Mole Snacks: +469/-72
  • Gender: Male
  • Organic Chemist
    • My research
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.
My research: Google Scholar and Researchgate

Offline scotchtape21

  • New Member
  • **
  • Posts: 4
  • Mole Snacks: +0/-0
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

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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.
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline Borek

  • Mr. pH
  • Administrator
  • Deity Member
  • *
  • Posts: 27637
  • Mole Snacks: +1799/-410
  • Gender: Male
  • I am known to be occasionally wrong.
    • Chembuddy
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
ChemBuddy chemical calculators - stoichiometry, pH, concentration, buffer preparation, titrations.info

Offline scotchtape21

  • New Member
  • **
  • Posts: 4
  • Mole Snacks: +0/-0
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

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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?
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline scotchtape21

  • New Member
  • **
  • Posts: 4
  • Mole Snacks: +0/-0
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

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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.
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Sponsored Links