Convert CH_2 = CH_2 to Diol - 2 Ways?

  • Thread starter Thread starter kanki
  • Start date Start date
Click For Summary

Discussion Overview

The discussion centers on methods to convert ethene (CH2=CH2) into a diol, specifically exploring two potential pathways: one involving mild oxidation with alkaline KMnO4 and another involving bromination followed by hydrolysis. The scope includes theoretical approaches and practical considerations in organic chemistry.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant asks if KMnO4 and water at room temperature can be used for mild oxidation to convert ethene directly into a diol, suggesting it as an alternative to bromination.
  • Another participant confirms that KMnO4 oxidation of alkenes to diols is used industrially and mentions OsO4 as another option, while noting the challenges of working with ethene as a gas.
  • A participant seeks clarification on whether the bromination followed by refluxing with alkaline is necessary to prepare ethane-1,2-diol.
  • Another participant suggests that dihydroxylation reactions could work but acknowledges the difficulties of handling gases in the lab, proposing that there may be simpler methods available.
  • Several participants express a humorous view on the complexity of organic chemistry, indicating that such questions are often seen as theoretical or book knowledge rather than practical knowledge.

Areas of Agreement / Disagreement

Participants express differing opinions on the necessity of bromination for the conversion to a diol, with some suggesting alternative methods while others affirm the traditional approach. The discussion remains unresolved regarding the best method to use.

Contextual Notes

Participants note the practical challenges of working with ethene as a gas and the potential for alternative methods, but do not reach a consensus on the most effective approach for laboratory preparation.

kanki
Messages
29
Reaction score
0
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.
 
Chemistry news on Phys.org
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.
 
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?
 
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.
 
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. :-p But maybe that's just because I hated ochem.

I don't know how organic chemists can remember all of this stuff. :-p Crazy bastards.
 
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!
 
movies said:
But somebody has to know this stuff to write the book!

They got it out of another book!
:-p
 

Similar threads

  • · Replies 3 ·
Replies
3
Views
3K
  • · Replies 3 ·
Replies
3
Views
2K
Replies
7
Views
3K
  • · Replies 9 ·
Replies
9
Views
5K
  • · Replies 19 ·
Replies
19
Views
11K
  • · Replies 1 ·
Replies
1
Views
2K
  • · Replies 6 ·
Replies
6
Views
7K
  • · Replies 28 ·
Replies
28
Views
5K
Replies
1
Views
3K
  • · Replies 10 ·
Replies
10
Views
18K