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Author: Subject: TCCA for the haloform reaction and ethanol question
Gui316
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[*] posted on 7-4-2012 at 10:50
TCCA for the haloform reaction and ethanol question


I was wandering if trichloroisocyanuric acid would work for the haloform reaction, as a substitue to the sodium hypochlorite, with is normaly used in this case.

I heard that the haloform reaction can be peformed with ethanol...Is that true? Well, I have always thought that the haloform reaction could only be peformed with methyl ketones, or secondary alcohols, which would turn into methyl ketone on the process...Ethanol would turn into acetaldehyde, right? So I wonder if the reaction would proceed in this case...
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woelen
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[*] posted on 7-4-2012 at 10:57


Have a look at this thread.

http://www.sciencemadness.org/talk/viewthread.php?tid=5686

TCCA can be used to make chloroform.




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Gui316
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[*] posted on 8-4-2012 at 07:30


Great thread, thank you for leading me there. But what about the ethanol? I'm not sure if ethanol can be used in the haloform reaction. I've done some research, and I couldn't find anything related to the oxidation of ethanol to the acetaldehyde using hypochlorite (as bleach or formed from the TCCA). But I found one website that said that ethanol can be used in the haloform reaction, but no details were given.
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[*] posted on 8-4-2012 at 09:12


Yes, ethanol can be used for the haloform reaction, just like acetone.



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[*] posted on 8-4-2012 at 15:17


Well, looks like acetone doens't need the base to react. I got really lost here. Having both ethanol and calcium hypochlorite mix together did not yield any chloroform at all. But when a solution of sodium hydroxide was added, it readily formed the chloroform, which was noticed by the sudden change of smell. So, I still lacking the knowledge about the mechanisms of this reaction...The base is actually to react with the halogen and form the hypohalite, is that correct? But in this case, the hypohalite was already there...
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