Conversion to Diol

  • Thread starter kanki
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  • #1
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Main Question or Discussion Point

Are there 2 ways to convert [itex]CH_2 = CH_2[/itex] into a diol?
Can i use the alkaline KMnO4 and water at room temperature(mild oxidation) to convert it into a diol instead of this reaction:
[itex]CH_2 = CH_2 (g) + Br_2(l) \xrightarrow {room temperature} CH_2BrCH_2Br(l)[/itex]
[itex]CH_2BrCH_2Br + 2 NaOH(aq) \xrightarrow {reflux} CH_2OHCH_2OH(l) + 2 NaBR(aq)[/itex]
Where it requires to convert ethene to 1,2-dibromoethane first.
 

Answers and Replies

  • #2
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Science Advisor
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In principle, yes. The KMnO4 oxidation of alkenes to diols is used industrially. You could also use OsO4. Working with ethene can be a little difficult, however, since it is a gas at STP.
 
  • #3
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Therefore to prepare ethane-1,2-diol in lab, we have to pass through bromine liquid and then reflux the product with alkaline, is that right?
 
  • #4
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Science Advisor
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Not necessarily. You could probably get one of the dihydroxylation reactions to work, it's just a pain to deal with gasses in the lab. If you really had to make it in the lab then there are probably better ways. Of course, you could always just buy the stuff. It's dirt cheap.
 
  • #5
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lol, the way I see it is, these types of questions aren't things people really know. This is book information....it is meant to be referred to in a BOOK. :tongue2: But maybe that's just because I hated ochem.

I don't know how organic chemists can remember all of this stuff. :tongue2: Crazy bastards.
 
  • #6
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leright said:
lol, the way I see it is, these types of questions aren't things people really know. This is book information....it is meant to be referred to in a BOOK.
But somebody has to know this stuff to write the book!
 
  • #7
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movies said:
But somebody has to know this stuff to write the book!
They got it out of another book!
:tongue:
 

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