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Topic: Reduction of carboxylic acids to aldehydes with CaH2  (Read 40325 times)

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Offline orgopete

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #45 on: May 20, 2011, 03:41:43 PM »
Was the complex formed to solubilize calcium hydride or to modify its reactivity? Does it matter? Could we exclude acetate from complexation? Before, calcium hydride was too hard to be a reductant, and now if it is a complex it can, but it isn't calcium hydride.

Let me repeat. I don't know whether calcium hydride could perform reductions or not. It doesn't seem so far fetched as many have argued. (I certainly didn't know that calcium hydride complexes could be used as reductants.) Someone could end this, does anyone have acetic acid and calcium hydride in their labs? Throw some calcium hydride (excess) into a small test tube, add a drop of acetic acid and heat it up. After the hydrogen stops coming off, if it bubbles after heating it, smell it. Does it smell like acetaldehyde?
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Offline karbon

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #46 on: May 20, 2011, 04:51:12 PM »
It doesn't seem far fetched since we call it calcium hydride and we know sodium borohydride can reduce. But thats about it, the name.

But it doesn't react like a hydride nucleophile. It acts as a base only. If any reduction were to happen it would probably be because you had some Pd/C in for the hydrogen gas to work with :)

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