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Topic: Aldehyde with H2O/H+  (Read 7723 times)

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Offline Dkona

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Aldehyde with H2O/H+
« on: January 26, 2009, 12:47:51 PM »
I have the following reaction:

http://img89.imageshack.us/my.php?image=rxnck1.jpg


At first, I thought since they are aldehydes, they would form geminal diols in the presence of water.  But geminal diols are unstable, so I don't think that's correct.  There isn't a large electron withdrawing group like a trichloromethyl which would make it a stable product.  Of I had a reagent like LiAlH4, or NaBH4 along with H3O+, I could make a primary alcohol from the aldehyde, but that's not the case here.  So I am not sure what it could do, I'm tempted to say that there would be no reaction.
« Last Edit: January 26, 2009, 01:11:40 PM by Dkona »

Offline azmanam

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Re: Aldehyde with H2O/H+
« Reply #1 on: January 26, 2009, 01:02:36 PM »
The aldehyde hydrate (the geminal diol) is the correct answer here.  The reaction is an equilibrium reaction.  If you apply some external stress to remove water from the reaction (mol sieves, distillative removal of water if applicable, etc), you can favor the hydrate.  To show your instructor you know what's going on, draw the equilibrium arrows, with the arrow pointing to the aldehyde and water as the longer arrow.
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