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Would acetanilide be more soluble in water at 25 degrees Celsius because it has an $\ce{N-H}$ and an oxygen that can participate in hydrogen bonding, whereas diethyl ether only has an oxygen?

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    $\begingroup$ Your argument would be good if you'd talk about acetamide, but that's N-phenylacetamide. Phenyl group changes things quite a bit if attached to a smaller molecule. $\endgroup$ – Mithoron Apr 23 at 20:42
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    $\begingroup$ What are you comparing? Acetanilide in water with acetanilide in diethyl ether? Or acetanilide in water with diethyl ether in water? $\endgroup$ – Karsten Theis Apr 23 at 20:53
  • $\begingroup$ I have a question on an organic chemistry assignment asking me to choose the least and most soluble molecules in water at 25 degrees celsius. Acetanilide and diethyl ether are the choices for the least soluble and i don't know how to choose which one is more soluble in water. I realize that the phenyl group weakens the H-bonding capabilities of acetanilide, but does that make it less soluble than diethyl ether? $\endgroup$ – JG-3014 Apr 23 at 21:54
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Acetanilide is approximately 10x more soluble in diethyl ether (1g dissolves in18ml) than in water (1g dissolves in 185ml). Source here

As @Mithoron said in the comments, that phenyl group has a big effect.

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I believe you are asking solubility of diethyl ether and acetanilide in water. If that the case, then diethyl ether is is more soluble in water than acetanilide at $\pu{25 ^{\circ}C}$:

Solubility of diethyl ether in water at $\pu{25 ^{\circ}C}$: $6.05\% (w/v)$ (Wikipedia)

Solubility of acetanilide in water at $\pu{25 ^{\circ}C}$: $\lt 0.56\% (w/v)$ (Wikipedia)

Here, as a novice to organic chemistry, you may concern mainly on number of carbons in each molecule (aside other factors such as presence of $\ce{N}$ and $\ce{O}$) to decide the solubility. But in future, you may learn the importance of that single $\ce{O}$ atom in ether molecule when you learn subjects like Grignard reagents.

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