Orgo question regarding LAH

[LebLlama]

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Sometimes LAH completey eradicates a ketone, while other times it reduces it down to an alcohol. Why is this? What am I missing.

 

[PiBond]

Sometimes LAH completey eradicates a ketone, while other times it reduces it down to an alcohol. Why is this? What am I missing.

i've never seen LiAlH4 completely eradicate a ketone on the MCAT. we usually just observe them turning carbonyls into alcohols. if i had to guess, it would be the fact that LiAlH4 is a more reactive reducing agent (compared to NaBH4), but again..i've never observed this. are you sure you're not confusing LAH with Wolff-kishner (which takes carbonyls down to alkanes)?

 

[orgohacks]

Sometimes LAH completey eradicates a ketone, while other times it reduces it down to an alcohol. Why is this? What am I missing.

I'm not certain if you see this in Org1/Org2 but LAH will reduce an alkyl halide down to an alkane.

I can't think of any examples you'd see in Org1/Org2 where LAH would take a ketone all the way down to an alkane however. If you can find an example that would be helpful.