Organic Lab Acetanilide Crystallization

[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!

 

[chemisttree]

Think more in terms of 'like dissolves like'. Are there any structural similarities between ethyl acetate and acetanilide? Hexane and acetanilide?

 

[rhyang]

Think more in terms of 'like dissolves like'. Are there any structural similarities between ethyl acetate and acetanilide? Hexane and acetanilide?

THANK YOU! Just what I needed. I understand now. Ethyl acetate and Acetanilide both have the double bond O, which I think is an ester group correct? And hexane doesn't, so that is why it is more soluble in ethyl acetate than in hexane?

 

[chemisttree]

Hey, you said it, not me!

 

[rhyang]

Haha, well thanks for the help! It really does feel better to have help and figure it out, rather than having someone just tell you the answer. =]

 

[Borek]

Judging from what you posted at chemicalforums I am not entirely sure you got it right...

 

[chemisttree]

RHYANG's pretty close. You just have to clean up your terminology. Amide is not ester and carbonyl group is not an ester.

Your question specifically asked to draw the structures of both hexane and ethyl acetate in your explanation. Therefore, you are absolutely correct to look for structural similiarities beween them and acetanilide rather than rely entirely on a discussion about polarity. Water is polar as well but will water dissolve acetanilide? Well, yes if 1 g/185 mL is considered soluble...

Don't be confused with someone's intrepretation that "like dissolves like" means polar dissolves polar.

You are on the right track.