Organic Chemistry Recrystallization

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Discussion Overview

The discussion revolves around the suitability of ethanol as a solvent for the recrystallization of phthalic acid, focusing on solubility characteristics and the miscibility of solvents. Participants explore the criteria for selecting appropriate solvents in recrystallization processes.

Discussion Character

  • Homework-related
  • Debate/contested
  • Conceptual clarification

Main Points Raised

  • One participant states that phthalic acid is very soluble in water, suggesting it as a good candidate for recrystallization, while expressing uncertainty about ethanol's properties.
  • Another participant asserts that water and ethanol are miscible, prompting confusion among others.
  • A different participant claims that phthalic acid must be highly soluble in ethanol but not in water at room temperature, arguing that this makes ethanol a poor choice for recrystallization.
  • One participant acknowledges a misunderstanding regarding the miscibility of water and ethanol after reviewing their chemistry book.
  • Another participant reiterates that a solvent should not react with the compounds, mentioning that alcohols can react with acids to form esters, which could also be a reason for ethanol's unsuitability.

Areas of Agreement / Disagreement

There is disagreement regarding the miscibility of water and ethanol, with some participants asserting they are not miscible while others claim they are. The discussion remains unresolved regarding the overall suitability of ethanol for recrystallization of phthalic acid.

Contextual Notes

Participants express uncertainty about the solubility criteria for recrystallization and the implications of solvent miscibility. There are also references to the reactivity of solvents with the compounds being recrystallized, which may affect their suitability.

Who May Find This Useful

Students studying organic chemistry, particularly those learning about recrystallization techniques and solvent properties.

CMATT
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Homework Statement


Why is ethanol a bad choice for recrystallization of phthalic acid?

2. The attempt at a solution

I know phthalic acid is very soluble in water, so water is a great candidate to recrystallize phthalic acid. I also know water and ethanol are not miscible. But I don't know how to properly answer this question. Please help.
 
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CMATT said:
I also know water and ethanol are not miscible.
Say what?
 
Water and ethanol are miscible!

Phthalic acid must be highly soluble in ethanol but not in water at room temp and therefore is a bad solvent for recrystallization. In order to have properly recrystallization the compound must be insoluble or only partially soluble in the solvent at room temperature but highly soluble in the solvent at or near its boiling point.
 
Bystander said:
Say what?
Sorry my chemistry book is confusing! I misread
 
alchemistf9 said:
Water and ethanol are miscible!

Phthalic acid must be highly soluble in ethanol but not in water at room temp and therefore is a bad solvent for recrystallization. In order to have properly recrystallization the compound must be insoluble or only partially soluble in the solvent at room temperature but highly soluble in the solvent at or near its boiling point.

Thank you so much! This makes more sense. My book had some description about solubility and pure compounds when recrystallizing, but I just couldn't grasp the concept. Thanks again!
 
CMATT said:

Homework Statement


Why is ethanol a bad choice for recrystallization of phthalic acid?

2. The attempt at a solution

I know phthalic acid is very soluble in water, so water is a great candidate to recrystallize phthalic acid. I also know water and ethanol are not miscible. But I don't know how to properly answer this question. Please help.
A solvent should also not react with the compounds ...
Alcohols react with acids to form esters ...that can also be one of the reason.
 

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