Reducing Ketones on Benzene Rings with H2, Pd/C, 45 psi

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SUMMARY

The discussion focuses on the reduction of ketones on benzene rings using hydrogen (H2) and palladium on carbon (Pd/C) at 45 psi. While catalytic hydrogenation can reduce carbonyls on aromatic rings to alcohols, fully reducing them to hydrocarbons is challenging and may require extended reaction times. Alternatives such as nickel or Raney catalysts, as well as variations in pressure or temperature, were suggested. Additionally, methods like Wolff-Kishner reduction or Clemmensen reduction are recommended for converting aromatic ketones to alkanes.

PREREQUISITES
  • Understanding of catalytic hydrogenation techniques
  • Familiarity with palladium on carbon (Pd/C) as a catalyst
  • Knowledge of Wolff-Kishner and Clemmensen reduction methods
  • Basic principles of reaction conditions, including pressure and temperature
NEXT STEPS
  • Research the mechanism of catalytic hydrogenation with H2 and Pd/C
  • Learn about the Wolff-Kishner reduction process for ketones
  • Investigate the Clemmensen reduction and its applications in organic synthesis
  • Explore the use of nickel and Raney catalysts in hydrogenation reactions
USEFUL FOR

Chemists, organic synthesis researchers, and students studying reaction mechanisms in organic chemistry will benefit from this discussion.

smithrg8
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Is there anyway that a Ketone on a benzene ring could be reduced to a hydrocarbon with the use of H2, Pd/C, 45 psi ? I know that carbonyls on aromatic rings are able to be reduced to alcohols via this method but would be interested in if it is possible (more so then practical) to fully reduce to a hydrocarbon w/ the listed reagents. I did some searching and may have found some articles which stated that it may be possible with quite a long reaction period. If this method won't would any variations of it suffice? Suppose H2 Nickel or Raney? Maybe increase in psi or temp?

Thanks for the help guys!
 

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A ketone on a benzene ring will be reduced with catalytic hydrogenation under pressure. However, in reference to the title of this thread, I'd also point out that a nitro group will be reduced to an amine under the same reaction conditions. So instead of going from m-nitrophenone to 3-ethylnitrobenzene, you'd most likely get 3-ethylaniline as your product instead. (EDIT: it's also possible to reduce the benzene ring to a cyclohexane under exposure to these types of conditions. It's better to look into something like a Wolff-Kischner reduction or a Clemmensen reduction to get an aromatic ketone to an alkane.)
 

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