Travis Curtis

Orgo I Lab

Experiment 6: Recrystallization and Melting Points

Discussion:
How did your group decide on the solvent to use for the recrystallization of the
unknown?
We attempted to dissolve our unknown into 5 different solvents, both at room
temperature, and at boiling temperature. An ideal solvent in this experiment would allow
the unknown compound to dissolve into solution at boiling temperature, but not at room
temperature. Two solvents possessed this quality; Water and Ethanol. Our TA was
consulted on which of these two solvents would be best for recrystallization, and we
were advised to use water.
How did your group decide on the identity of the unknown after recrystallization?
After we recrystallized Unknown X, we determined its identity by finding its melting
point. We found the melting point of our recrystallized unknown to be 188oC. The only
potential unknown with a melting point in this range was Hippuric acid, with a melting
point range of 187-188oC.
Was the solubility information helpful in narrowing down the possibilities?
Solubility of Unknown X
Solvent

Solubility at 21 C

Solubility at BP

Hexane

Insoluble

Insoluble

Ether

Insoluble

Insoluble

EtOH

Insoluble

Soluble

Acetone

Soluble

Soluble

Water

Insoluble

Soluble

The solubility information was not particularly helpful. We could assume that we had a
somewhat polar compound, because the compound was soluble in Acetone and Water,
and both are polar.

Provide a short discussion about the decolorization of brown sugar using activated
charcoal.
Charcoal was added to a solution with dissolved brown sugar. It was boiled for 5
minutes and then passed through a paper filter. The solution was significantly lighter
than before the addition of charcoal. Charcoal readily absorbs non-polar molecules. The
fact that much of the brown color disappeared after charcoal was added to the solution
suggests that the organic compounds responsible for the brown color of the sugar were
non-polar and were absorbed into the charcoal.
Questions:
1 - The easiest way to determine that all of the sugar wasnt absorbed into the charcoal
would be to taste the solution. Charcoal isnt toxic, and the solution would be sweet if
only the color and not the sugar were absorbed. But since were not supposed to put
things in our mouth in lab you could evaporate the water out of the solution, test the
melting point of the remaining solid, and compare it to sugars known melting point.
2 - I assume that charcoal has a limit in its ability to absorb impurities, and after this limit
is reached, adding additional charcoal will not remove additional colored impurities.
Also, adding an excessive amount of charcoal might in fact add dark color to the
solution, and filter paper might not remove all of this.
3 - The student likely had an overhydrated sample. If the crystals are not completely
dried, they will weigh more and have a lower melting point.
4 - The student lost 73mg of their unknown solid somewhere in the experiment. It's
possible that some of the unknown remained in solution after boiling because it was not
sufficiently cooled. It is also possible that portions of the recrystallized solid were stuck
to the sides of the test tube and were therefore unable to be weighed.