H2, Pd @ 45 psi Whats is the reduction Limits here

[MobiusStrip]

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H2, Pd @ 45 psi... Can this reduce the c=o bond of a carbony group?

Is there anyway that this could in fact do this ? How about any variations of this... like H2 pd, CaCO3 or H2 Pd Raney? Thanks for the help guys!!!​

 

[loveoforganic]

Increasing the pressure will increase the reducing power. You'd have to check the literature for exact conditions.

 

[MobiusStrip]

Thanks for the reply. I got this marked wrong on an orgo test but I believe with a catalyst and pressure or heat that this will get the job done. Currently taking orgo with different prof which dislikes first sem orgo instructer who taught that this could indeed work. Trying to sift through google books but not having a whole lota luck.

 

[DQLEUCD]

Thanks for the reply. I got this marked wrong on an orgo test but I believe with a catalyst and pressure or heat that this will get the job done. Currently taking orgo with different prof which dislikes first sem orgo instructer who taught that this could indeed work. Trying to sift through google books but not having a whole lota luck.

This will reduce any pi bonds in the system except for benzene rings I believe. But answering the question, it'll reduce the carbonyl group easily.

 

[MobiusStrip]

If you know of anywhere that shows this I would be more than willing to hook you up with any study material needs, tbanks whatever. Mechanistic image on the web would be money.

 

[loveoforganic]

Why not ask first sem prof for a lit example? Probably depends on solvent system though. Pretty sure you the enol tautomer is the reactive moiety

 

[MobiusStrip]

Chad from chads videos was able to give me a reason that I was able to understand (helpful guy) so I thought I would post up what I found out...

Ah yes, this is a selective reduction. It only works for benzylic (adjacent to a benzene ring) ketones and aldehydes but they will be completely reduced to a hydrocarbon. My earlier response was only with regard to ketones and aldehydes in general. Following a Friedel-Crafts acylation we will commonly reduce the resulting ketone to a hydrocarbon using the Clemmensen Reduction (Zn(Hg)/HCl) or the Wolff-Kishner Reduction (N2H4/KOH/heat) but this catalytic hydrogenation you sited will accomplish the same thing since the ketone product of the Friedel-Crafts acylation is benzylic.