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teqeishajohnso teqeishajohnso
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11 years ago
I'm really struggling to understand my organic chemistry lab!!

In the lab, I reduced 4-methylacetophenone with sodium borohydride (NaBH4).  I was to find my own protocol online.  The protocol I chose was a microwave procedure in which the ketone was merely added to a alumina/sodium borohydride mixture.  The resulting product was an alcohol.

I am struggling to understand the mechanism of the reaction.  Unlike most similar reductions I am finding online, there was no water present in the reaction (just nabh4, the acetophenone, and dry alumina).  how does the reaction mechanism proceed, then?
What nucleophile attacks the carbon to release the OBH3- leaving group?

thank you!
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wrote...
11 years ago
The product is an alcohol so no C-O bond is broken. I suggest you write the mechanism in the same way the solution reaction is written. If no water or OH bonds were present, the product would be the borate ester of the alcohol. Since alumina contains Al(OH) bonds, they can act as proton sources. Even dry alumina may still contains measurable amounts of water unless it has been recently calcined.  Since I am unfamiliar with this procedure, I don't know what possible proton sources may be present.
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