Xellos
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Acetone+NaOH
I mixed 40 ml of acetone (p.a.) and 2 g of NaOH powder, hoping to get aldol condensation to diacetone alcohol, possibly also mesithyl oxide and even
to isophorone. However, the rection mixture turned red-brown in 30 mins, and 3-4 hrs later, yellow precipitate started to form. Reaction has been done
at room temperature (20 °C now), without any solvent. I wonder what it is...
Xellos
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ScienceSquirrel
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Gunge
http://onlinelibrary.wiley.com/doi/10.1002/apmc.1996.0523601...
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Nicodem
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Thread Moved
6-3-2012 at 07:37 |
Xellos
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I see... damn, I hoped for it to be something nicer... more like at most 2 products... oh well
Xellos
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AirCowPeaCock
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That's the nature of aldol condensations, I believe...
[Edited on 3-6-2012 by AirCowPeaCock]
BOLD
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Xellos
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Hm... I did a few aldol reactions and didn't get any polymer or ugly mixture of many products in small yields (although these were more like
benzaldehyde+acetone, with finite products, and while trying to minimize the self-aldol reactions). I did this one for curiosity - what and how fast
will happen.
Getting multiple products is fine for me - as long as these are all products of aldol reactions to the same degree with normal yields (and if they can
be separated, it's great). This is just a polymer - not a mixture of specific compounds, way too big molecules for me to like, etc.
Xellos
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bfesser
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This article is now available in the reference section, for those with access:
http://www.sciencemadness.org/talk/viewthread.php?tid=19098#...
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AndersHoveland
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Yes, acetone will condense with itself in the presence of a strong base.
Something like HOC(CH3)2CH2COCH3 will be the initial condensation product, but there will be further condensation.
Remember the acetone has an enol tautomer. Yet acetone can also condense in another way, such as the reaction of chloroform with acetone to form
chlorobutanol.
I made a detailed post about acetone reacting with base on one of these science forums but it is not appearing in a search now.
[Edited on 9-3-2012 by AndersHoveland]
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Adas
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This experiment yields the same compounds as acid + acetone. I have done this few days ago, and I got a dark red solution. I believe the terribly
(pesticide?) smelling substance is phorone or isophorone (isophorone is used in some pesticides, I smelled it everytime when one of my relatives was
spraying garden against insects IIRC).
Rest In Pieces!
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