JefferyH - 16-8-2014 at 01:28
I read borohydride reduces carbonyls to alcohols, but also is known to produce hydrogen when in methanol as it decomposes. What is happening here?
Does this happen to all alcohols, and is the alcohol consumed in this reaction?
I basically have trace amounts of a primary alcohol mixed with a reactant I hope to reduce, and I want to predict whether or not the reaction will be
effected by this trace alcohol. The trace alcohol is less than 1-3%
forgottenpassword - 16-8-2014 at 08:58
It won't be affected. Even assuming that your alcohol destroyed all of the borohydride that it came in contact with, the worse that would happen is
you would have 1-3% less borohydride than you added. Or a quarter of that amount. Anyway, negligible. But it won't, because of the primary alcohols,
only methanol decomposes borohydride at an appreciable rate, especially at room temperature, and by that time your carbonyl will have used up the
borohydride anyway.
[Edited on 16-8-2014 by forgottenpassword]