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The chemical structure of phenobarbital is:

The aromatic ring and methyl group will be more favorable for organic solvent, while the NH in the ring and O attachments favor aqueous solvents.

One gram is soluble in approximately 1000 ml of water, and 10 ml of alcohol. Compared to other barbiturates it has a lowlipid solubility. It is very soluble in water, soluble in alcohol, and freely solu­ble in propylene glycol. In other words, the question makes an incorrect assumption - phenobarbital is MORE soluble in aqueous solvents than in organic solvents.

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Q: Why phenobarbital soluble in organic solvent more than aqueous solvent?
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