Organic Chemistry Recrystallization

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SUMMARY

Ethanol is a poor choice for recrystallization of phthalic acid due to its high solubility in the solvent at room temperature, which contradicts the requirements for effective recrystallization. A suitable recrystallization solvent must allow the compound to be insoluble or only partially soluble at room temperature while being highly soluble at or near the boiling point. Additionally, ethanol's reactivity with acids, forming esters, further complicates its use in this context. Water is identified as a better solvent for recrystallizing phthalic acid due to its properties.

PREREQUISITES
  • Understanding of solubility principles in organic chemistry
  • Knowledge of recrystallization techniques
  • Familiarity with the properties of phthalic acid
  • Basic concepts of solvent interactions and miscibility
NEXT STEPS
  • Research the solubility characteristics of phthalic acid in various solvents
  • Study the recrystallization process and its requirements
  • Learn about the reactivity of alcohols with acids and the implications for solvent choice
  • Explore alternative solvents for recrystallization of organic compounds
USEFUL FOR

Chemistry students, organic chemists, and anyone involved in laboratory techniques related to recrystallization and solvent selection.

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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