O Chem Question- alpha-beta unsaturated carbonyl reaction

[Gbrando2]

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.So if I have 6 carbon chain, with C2 double bonded to an oxygen and a double bond from C3-C4 and I throw it in with NaBH4 and CH3OH, will I get H's added at the carbonyl carbon and the oxygen to make a secondary alcohol? Or will it add at C3 and C4 to get rid of that double bond? Or is NaBH4 not strong enough for a reaction? Any help would be great, thanks .

 

[9000]

Reduction of a ketone leads to a 2o alcohol.

 

[Gbrando2]

That's what I thought, I just wasn't sure if the conjugated double bond would throw it off. It's not always a secondary alcohol though. If it's a ketone like the one I described above and you reduce it with 1 equiv. H2 and Pd, it will only reduce the c-c double bond and won't touch the carbonyl. And if you use 2 equiv. H2 and Pd, it will reduce both double bonds. But I think that only applies for H2, so yes it would be a secondary alcohol.