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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: midas44 on October 04, 2020, 08:56:26 PM

Title: Why are acetanilide and phenacetin soluble in dichloromethane?
Post by: midas44 on October 04, 2020, 08:56:26 PM: In my Panacetin lab I understand that sucrose is insoluble in dichloromethane. I also understand that dichloromethane is technically polar but can be considered nonpolar. If it is technically polar why can it not dissolve glucose but can dissolve acetanilide and phenacetin, which are both polar molecules?

I only ask because I have to explain their intermolecular forces. If phenacetin and acetanilide are polar, then they have dipole-dipole forces at play and also hydrogen bonds. But if they are polar why does sucrose not dissolve in DCM but acetanilide and phenacetin can?
Title: Re: Why are acetanilide and phenacetin soluble in dichloromethane?
Post by: chenbeier on October 05, 2020, 01:18:22 AM: Sugar has to many OH groups and these make Hydrogen bonds so it's way to dissolve in water.DCM is even it has the 2 chlorine a more or less non polar compound. It make. No hydrogen bonds. So sugar is insoluble.
Title: Re: Why are acetanilide and phenacetin soluble in dichloromethane?
Post by: Babcock_Hall on October 05, 2020, 10:02:29 AM: One thing to keep in mind in assessing overall polarity is the relative sizes of the polar and non-polar portions of a molecule.
Title: Re: Why are acetanilide and phenacetin soluble in dichloromethane?
Post by: midas44 on October 06, 2020, 10:42:46 AM: Quote from: Babcock_Hall on October 05, 2020, 10:02:29 AM
One thing to keep in mind in assessing overall polarity is the relative sizes of the polar and non-polar portions of a molecule.

So how does this make it soluble in DCM but sucrose is insoluble?
Title: Re: Why are acetanilide and phenacetin soluble in dichloromethane?
Post by: midas44 on October 06, 2020, 10:43:03 AM: Quote from: chenbeier on October 05, 2020, 01:18:22 AM
Sugar has to many OH groups and these make Hydrogen bonds so it's way to dissolve in water.DCM is even it has the 2 chlorine a more or less non polar compound. It make. No hydrogen bonds. So sugar is insoluble.

I'm sorry, what?
Title: Re: Why are acetanilide and phenacetin soluble in dichloromethane?
Post by: Babcock_Hall on October 06, 2020, 11:06:50 AM: Quote from: midas44 on October 06, 2020, 10:42:46 AM
Quote from: Babcock_Hall on October 05, 2020, 10:02:29 AM
One thing to keep in mind in assessing overall polarity is the relative sizes of the polar and non-polar portions of a molecule.

So how does this make it soluble in DCM but sucrose is insoluble?
Sucrose has many -OH groups and no hydrocarbon portions; therefore, it has no non-polar regions. What about phenacetin?
Title: Re: Why are acetanilide and phenacetin soluble in dichloromethane?
Post by: GabrielTojo on October 23, 2020, 08:02:53 PM: Dichloromethane is very non polar.