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Date: 15-10-2019
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Date: 2-10-2018
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Date: 31-10-2019
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Catalytic hydrogenation of aromatic rings requires forcing conditions (high heat and hydrogen pressure).
Under milder conditions it is possible to reduce the double-bond of an alkene without reducing the aromatic ring.
Notice in the above equation that H2/Pd does not reduce the keto-carbonyl group. Remember, however, that H2/Pd will reduce a keto-carbonyl group when it is directly attached to an aromatic ring (see equations 4 and 5 under Carbonyl Reductions).
This reduction of the C=O group next to an aromatic ring is an important synthetic tool. Recall the Friedel-Crafts alkylation from Section 16.3. When attaching larger alkyl groups to arenes there is a possibility of rearrangement of the alkyl group structure.
To generate the target compound (in this case n‑propylbenzene) in a more controlled fashion, one can simply use the equivalent Friedel-Crafts acylation and then reduce the keto-carbonyl group next to the ring as a final step.
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