[rhyang]

Okay, so I'm having trouble with a question on a Pre-Lab assignment.

The question is,

"Acetanilide is more soluble in etyhl acetate than in hexane. Why? Draw the structures of etyl acetate and hexane in your explanation."

So I know Acetandilide is polar, and hexane is a solvent for nonpolar substances right? But how do I use the structures to answer this question? Kind of confused of what he wants to know?

Can anyone help? Thanks!

[Borek]

Why is acetanilide polar?

[rhyang]

Why is acetanilide polar?

Oh is it not? I have no clue I thought I read it somewhere. If I'm wrong let me know so I can change it, don't wanna look totally stupid now.

[nj_bartel]

It is polar.  He's just asking why.  Looks at electronegativities of varying atoms, what they're connected to, etc.

[rhyang]

It is polar.  He's just asking why.  Looks at electronegativities of varying atoms, what they're connected to, etc.

Oh so does this have to do with why Acetanilide is more soluble in etyhl acetate than in hexane? Something with polarity?

[rhyang]

I think I've got the answer now. Acetandilide and ethyl acetate are both esters correct? so since "like dissolves like" it becomes more soluble in ethyl acetate than hexane? Correct me if I'm wrong?

[nj_bartel]

Acetanilide is not an ester.  At any rate, that is not the meaning of 'like dissolves like' exactly.  'Like dissolves like' means that polar molecules dissolve polar molecules, nonpolar => nonpolar, etc.  While functional groups themselves will have similar polarity, this polarity does not necessarily translate into defining the polarity of the molecule.  For example, C-Cl bond is a highly polarized bond, but CCl₄ is completely nonpolar.  To determine the polarity of a molecule, you must sum the vectors arrising from each dipole moment of every bond (with time/practice, you can begin to judge polarity by just looking at a molecule, without actually summing vectors).

[cundi]