MSN Home  |  My MSN  |  Hotmail
Sign in to Windows Live ID Web Search:   
go to MSNGroups 
Free Forum Hosting
 
Important Announcement Important Announcement
The MSN Groups service will close in February 2009. You can move your group to Multiply, MSN’s partner for online groups. Learn More
Chemistry Corner[email protected] 
  
What's New
  
  Welcome Page  
  About This Site  
  Message Boards  
  General  
  Inorganic  
  Organic  
  Pictures  
  Random  
  FOR ALL  
  Handy Symbols  
  Chemistry Humor  
    
  Documents  
  Chemistry Sites I  
  Chemistry Sites II  
  Chemistry Sites III  
  Organic Sites I  
  Organic Sites II  
  Analytical Sites I  
  Analytical Sites II  
  Lesson Plan Sites  
  Online Problems  
  Names & Formulas  
  Naming Exercises  
  Equations I  
  Equations II  
  Eq. Exercises I  
  Eq. Exercises II  
  The Mole I  
  The Mole II  
  Mole Exercises  
  Stoichiometry  
  Stoich. Exercises  
  More Communities  
  School's Out!  
  _________________  
  Site Map  
  
  
  Tools  
 
Organic : Oxidation of Ethyne + Iodine
Choose another message board
 
     
Reply
 Message 1 of 4 in Discussion 
From: MSN Nicknamestrike101  (Original Message)Sent: 11/2/2006 12:17 AM
hello

i have a question about the oxidation of ethyne with diluted KMno4. i have no idea if its cold or hot all i know is that the ethyne is being produced by calcium carbide at room temp, in water. Will it be formic acid or will it be oxalic acid,,,


And how about if iodine water is added to the ethyne sample? its 10 drops so i think its considered excess amount.

Thank you.


First  Previous  2-4 of 4  Next  Last 
Reply
 Message 2 of 4 in Discussion 
From: MSN Nickname·Steve·Sent: 11/2/2006 6:42 AM
Hi, that's a good question regarding the oxidation of ethyne.  This question was asked before (see the message thread here) but unfortunately I have not learned any more about this reaction.  Here are a few statements on the Internet that you may have seen:

http://mattson.creighton.edu/C2H2/index.html
Ethyne and permanganate react with cleavage of the carbon-carbon triple bond and formation of the formate ion and the carbonate ion.  The stoichiometry for the oxidation by permanganate under neutral or slightly acidic conditions is:

3 C2H2 (g)  +  8 MnO4�?/SUP> (aq)  +  8 H+ (aq)   ––�?gt;   3 HCOOH (aq)  +  3 CO2 (g)  +  8 MnO2 (s)  +  4 H2O (l)

If the conditions are neutral or acidic, the formate ion is converted to formic acid and the carbonate ion forms carbon dioxide.  Indeed, as the reaction proceeds, tiny bubbles are observed in the aqueous phase.
 
http://www.ucc.ie/academic/chem/dolchem/html/dict/alkynes.html
Ethyne is oxidised by a dilute aqueous solution of potassium permanganate to form oxalic acid. Thus, if ethyne is bubbled through a solution of potassium permanganate the solution is decolourised. This is Baeyer's test for unsaturated organic compounds.
 
http://wwwscience.murdoch.edu.au/teach/m114/Organic2.htm
Acidified permanganate oxidises acetylene to CO2/H2O.  The observation is decolourisation of the permanganate.
 
 
No doubt the reaction outcome heavily depends on the conditions used:  hot vs. cold; acidic vs. basic vs. neutral; concentrated vs. dilute.  Concentrated, hot, acidic permanganate would favor complete oxidation to CO2 and H2O, while milder conditions could give formic acid and/or oxalic acid.
 
A Review of Chemical Oxidation Technology (informative, includes permanganate oxidation of alkenes, but not alkynes) is at
http://2the4.net/html/chemoxwp.htm
 

>>  And how about if iodine water is added to the ethyne sample?  Its 10 drops so I think its considered excess amount.  <<

Since alkenes do not generally undergo addition reactions with I2, and since alkynes are considerably less reactive towards addition of halogens, ethyne may not react at all with a dilute solution of iodine in water.  The difficulty is the unfavorable formation of the alkene halonium ion intermediate, the first step in the reaction.
 

Steve

Reply
 Message 3 of 4 in Discussion 
From: MSN Nickname·Steve·Sent: 11/2/2006 7:09 AM
That first reference about ethyne oxidation (http://mattson.creighton.edu/C2H2/index.html) strikes me as the most reliable.  I wish they stated whether they analyzed the reaction mixture to confirm that formic acid is formed, rather than oxalic acid.
 

Reply
 Message 4 of 4 in Discussion 
From: MSN Nickname·Steve·Sent: 11/5/2006 8:41 PM
William Reusch notes in his Virtual Textbook of Organic Chemistry that the reaction of ethyne with I2 is slow, giving trans-1,2-diiodoethene which apparently does not react further with I2.  See http://www.cem.msu.edu/~reusch/VirtualText/addyne1.htm#add1.  That's all I've been able to find out about this reaction so far.  In an aqueous environment we would expect to form the enol trans-2-iodoethen-1-ol which should tautomerize to 2-iodoethanal (iodoacetaldehyde).

Steve

First  Previous  2-4 of 4  Next  Last 
Return to Organic