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NaBH4 vs LiAlH4


The Law

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I seem to recall there is a very important difference between these two in terms of reductive-strength. It doesn't mention this in the TPR book, so I might have made it up - but wanted to see if I was right, and if so, what this difference was! Gosh, been too long since I did orgo!

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I seem to recall there is a very important difference between these two in terms of reductive-strength. It doesn't mention this in the TPR book, so I might have made it up - but wanted to see if I was right, and if so, what this difference was! Gosh, been too long since I did orgo!

 

Lithium aluminium hydride is widely used in organic chemistry as a reducing agent. It is more powerful than the related reagent sodium borohydride due to the weaker Al-H bond compared to the B-H bond.

 

Unlike the powerful reducing agent lithium aluminium hydride, sodium borohydride typically will not reduce esters, amides, or carboxylic acids. (This is the important distinction you need to be aware of for the MCAT.)

 

Sources: http://en.wikipedia.org/wiki/Lithium_aluminium_hydride http://en.wikipedia.org/wiki/Sodium_borohydride

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