Organic Lab Acetanilide Crystallization

In summary: Hexane and acetanilide are both nonpolar solvents, which is why acetanilide is more soluble in ethyl acetate.
  • #1
rhyang
3
0
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!
 
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  • #2
Think more in terms of 'like dissolves like'. Are there any structural similarities between ethyl acetate and acetanilide? Hexane and acetanilide?
 
  • #3
chemisttree said:
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?
 
  • #4
Hey, you said it, not me!
 
  • #5
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. =]
 
  • #6
Judging from what you posted at chemicalforums I am not entirely sure you got it right...
 
  • #7
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.
 

What is the purpose of acetanilide crystallization in organic lab?

The purpose of acetanilide crystallization is to purify the compound by removing impurities and obtaining a highly concentrated and pure sample for further analysis.

What is the process of acetanilide crystallization?

The process of acetanilide crystallization involves dissolving the compound in a solvent, heating the solution to dissolve the compound completely, and then allowing the solution to cool down slowly. This results in the formation of pure acetanilide crystals as the solution cools.

What are some common solvents used for acetanilide crystallization?

Some common solvents used for acetanilide crystallization include water, ethanol, and ethyl acetate. The choice of solvent depends on the solubility of the compound and its impurities.

What factors can affect the success of acetanilide crystallization?

The success of acetanilide crystallization can be affected by various factors such as the choice of solvent, the rate of cooling, the size of the crystals, and the presence of impurities. It is important to carefully control these factors to obtain pure and well-formed crystals.

What is the role of vacuum filtration in acetanilide crystallization?

Vacuum filtration is used in acetanilide crystallization to separate the pure crystals from the solvent and any remaining impurities. It is a quick and efficient method of obtaining a solid product and is often used in organic lab experiments.

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