To Sheryl: polarity

posted by .

The exact question is: Benzyl alcohol (bp 205 degree C) was selected by a student to crystallize fluorenol (mp 153-154 degrees C) because the solubility characteristics of this solvent are appropriate. However, this solvent is not a good choice. Explain.

So the melting point looks okay and both would seem to be nonpolar, according to your researches. What else could it be?

Sheryl
I talked to my friend at lunch. He has a Ph. D. in organic chemistry. The OH on the fluorene (to become fluorenol) is somewhat acidic making it somewhat polar. But the REAL problem is that benzyl alcohol (which isn't very polar either)is just too good a solvent; i.e. the same reasoning we went through on the biphenyl/benzene crystallization. The fluorenol is so soluble in benzyl alcohol that very little can be removed after solution so it is a poor solvent for purposes of recrystallization. I hope this information is useful. BTW, I thought some more about the Buchner funnel/saturated solution question we were discussing. We know, of course, that cooling will take place and that some of the solute probably will ppt which makes solute appear as a solid on th funnel as well as in the liquid that goes through the funnel. Therefore, a good separation is not obtained BETWEEN THE SOLUTE AND THE SOLVENT. But that may not be the real question. Why did we filter the saturated solution in the first place. If because we want to seaparate some solid impurities from the solute in the saturated solution, we will have the solid impurities along with some of the crystallized solute in the Buchner funnel. Again, if the solute is what we are interesting in collecting, then the yield suffers because some of the product has been removed from the solvent and is mixed in with the solid impurities.



Thanks for the extra effort. Just got back from lab.

Hope you had a nice lunch with your friend.

Sheryl

  • To Sheryl: polarity -

    No, it's because the BP (205C) is too high for fluorenol's MP. So you boil your solution and it's still all dissolved, but you start cooling it and instead of the fluorenol crystallizing it will start "oiling" out, as in becoming a miscible liquid in the benzyl alcohol, so you won't get crystals.

Respond to this Question

First Name
School Subject
Your Answer

Similar Questions

  1. Best solvent?

    What is the best solvent for impure fluorene?
  2. Polarity

    Benzyl alcohol is not a good sovent with which to crystallize fluorenol. The melting point looks okay so I'm assuming that polarity is the problem. Benzyl alcohol looks polar to me because it has an OH but it is only partly soluble …
  3. Low recovery

    The question is: A student performs a crystallization on an impure sample of biphenyl. The sample weighs 0.5g and contains about 5% impurity. Using his knowledge of solubility, he decides to use benzene as a solvent. The final weight …
  4. Rf values

    Question: Consider a sample that is a mixture composed of biphenyl, benzoic acid and benzyl alcohol. The sample is spotted on a TLC plate and developed in a dichloromethane-cyclobutane solvent mixture. Predict the relative Rf values …
  5. Solvent

    Question: A sample was placed on a chromatography column. Methylene chloride was used as the eluting solvent. All of the components eluted off the column but no separation was observed. What must have been happening during this experiment:?
  6. Chemistry

    Benzyl alcohol (boiling point: 205 degrees C) was selected by a student to crystallize fluorenol (melting point: 153-154 degrees C) because the solubility characteristics of this solvent are appropriate. However, this solvent is not …
  7. Chemistry

    Benzyl alcohol (boiling point: 205 degrees C) was selected by a student to crystallize fluorenol (melting point: 153-154 degrees C) because the solubility characteristics of this solvent are appropriate. However, this solvent is not …
  8. Organic Chemistry

    Referring to solvent mixtures, which statements are TRUE ?
  9. Chemistry

    For the Following sets of compounds determine the best solvent, by looking at structure, also by looking at solubility vs. temp. Which is the best solvent for crystalization, in which the compound is too soluble, and in which solvent …
  10. bc

    Benzyl alcohol (b.p. 205 °C) was selected by a student to crystallize fluorenol (m.p. 153-154 °C), because the solubility characteristics of this solvent are appropriate. H

More Similar Questions