Organic Lab Acetanilide Crystallization

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Discussion Overview

The discussion revolves around the solubility of acetanilide in different solvents, specifically ethyl acetate and hexane. Participants explore the reasons behind the differing solubility based on molecular structure and polarity, as well as the implications of the phrase "like dissolves like." The context includes pre-lab assignment questions related to organic chemistry concepts.

Discussion Character

  • Conceptual clarification
  • Debate/contested
  • Homework-related

Main Points Raised

  • One participant notes that acetanilide is polar and suggests that hexane is a solvent for nonpolar substances.
  • Another participant emphasizes the concept of "like dissolves like" and prompts consideration of structural similarities between ethyl acetate and acetanilide, as well as between hexane and acetanilide.
  • A later reply indicates that both ethyl acetate and acetanilide contain a carbonyl group, which the participant identifies as an ester group, while hexane does not, suggesting this as a reason for the greater solubility in ethyl acetate.
  • One participant corrects the terminology used by another, clarifying that acetanilide is an amide, not an ester, and questions the reliance on polarity alone to explain solubility.
  • There is a mention of water's polarity and its limited solubility of acetanilide, indicating that the relationship between polarity and solubility may not be straightforward.

Areas of Agreement / Disagreement

Participants express differing views on the terminology and the implications of polarity in solubility. While some agree on the structural similarities being relevant, there is no consensus on the terminology and the extent to which polarity explains solubility.

Contextual Notes

There are unresolved issues regarding the correct terminology for functional groups and the complexity of solubility beyond the simple "like dissolves like" principle. The discussion also highlights the need for careful consideration of structural characteristics in relation to solubility.

rhyang
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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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Think more in terms of 'like dissolves like'. Are there any structural similarities between ethyl acetate and acetanilide? Hexane and acetanilide?
 
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?
 
Hey, you said it, not me!
 
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. =]
 
Judging from what you posted at chemicalforums I am not entirely sure you got it right...
 
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.
 

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