Recrystallization lab, Study notes of Chemistry

Purpose: The purpose of this experiment is to purify organic compounds which are solid at room temperature through the recrystallization process. Pre-Lab: Leave ...

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Name: Ryan D’Alleva Unknown Number(s): 9
Experiment Title: Recrystallization
Section Day/Time: Thursday/1:30-5:25 If Make-Up, lab performed on:_______________
Teaching Assistant: Enes Buz
Lab Technique: Leave this section blank in your report. But, make sure to tell Gradescope
it is on page one of your lab report. Your TA will assign the technique points when they
grade the post-lab. Do not delete this text.
Purpose: The purpose of this experiment is to purify organic compounds which are solid at room
temperature through the recrystallization process.
Pre-Lab: Leave this section blank in your post-lab report. But, make sure to tell Gradescope it
is on the appropriate page. Your TA should have graded the prelab before you began the
experiment. They will assign the awarded points for the prelab with the report. Do not delete
this text.
In-Lab Entries and Observations: The recrystallization experiment was performed on
September 19, 2019. Unknown #9 was assigned in the laboratory. The first step in the
experiment required conducting solvent tests to determine the best solvent for recrystallizing the
unknown compound––a solvent that has high solubility at high temperatures and low solubility
at low temperatures. This was done by adding 0.25 milliliters of each solvent to (different) test
tubes with 10 milligrams of the unknown compound, and then bringing the solution to near or at
a boil. Then, if the compound dissolved, it was allowed to cool to begin crystallization. Just two
of the given solvents were found to be unsuitable for the unknown compound, as the hexane
solution was insoluble at all temperatures and the 70% ethanol solution was soluble at all
temperatures. Therefore, these two solvents were not considered for use. Water, toluene, ethanol,
and methanol all dissolved the compound whilst boiling and allowed for the formation of crystals
upon cooling. Toluene notably produced large crystals very quickly, whereas ethanol and
methanol formed crystals very slowly. Once the solvents were tested, the experiment moved
towards the macro scale recrystallization of phthalic acid.
0.254 grams* of phthalic acid were weighed out and placed into an Erlenmeyer flask.
Through pipet drops, boiling water was added while simultaneously heating the flask. This was
done until complete dissolution had taken place, which took approximately 5 minutes. Once this
occurred, the flask was allowed to cool to room temperature, and then placed into an ice bath to
further induce crystallization. The crystals were separated from the solution via suction filtration,
and then stored away to dry.
*The procedure required 0.325 +/- .01 grams to be used, but this was misread and 0.254 grams
were used instead.
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Name: Ryan D’Alleva Unknown Number(s): 9 Experiment Title: Recrystallization Section Day/Time: Thursday/1:30-5:25 If Make-Up , lab performed on:_______________ Teaching Assistant: Enes Buz Lab Technique: Leave this section blank in your report. But, make sure to tell Gradescope it is on page one of your lab report. Your TA will assign the technique points when they grade the post-lab. Do not delete this text. Purpose : The purpose of this experiment is to purify organic compounds which are solid at room temperature through the recrystallization process. Pre-Lab : Leave this section blank in your post-lab report. But, make sure to tell Gradescope it is on the appropriate page. Your TA should have graded the prelab before you began the experiment. They will assign the awarded points for the prelab with the report. Do not delete this text. In-Lab Entries and Observations : The recrystallization experiment was performed on September 19, 2019. Unknown #9 was assigned in the laboratory. The first step in the experiment required conducting solvent tests to determine the best solvent for recrystallizing the unknown compound––a solvent that has high solubility at high temperatures and low solubility at low temperatures. This was done by adding 0.25 milliliters of each solvent to (different) test tubes with 10 milligrams of the unknown compound, and then bringing the solution to near or at a boil. Then, if the compound dissolved, it was allowed to cool to begin crystallization. Just two of the given solvents were found to be unsuitable for the unknown compound, as the hexane solution was insoluble at all temperatures and the 70% ethanol solution was soluble at all temperatures. Therefore, these two solvents were not considered for use. Water, toluene, ethanol, and methanol all dissolved the compound whilst boiling and allowed for the formation of crystals upon cooling. Toluene notably produced large crystals very quickly, whereas ethanol and methanol formed crystals very slowly. Once the solvents were tested, the experiment moved towards the macro scale recrystallization of phthalic acid. 0.254 grams* of phthalic acid were weighed out and placed into an Erlenmeyer flask. Through pipet drops, boiling water was added while simultaneously heating the flask. This was done until complete dissolution had taken place, which took approximately 5 minutes. Once this occurred, the flask was allowed to cool to room temperature, and then placed into an ice bath to further induce crystallization. The crystals were separated from the solution via suction filtration, and then stored away to dry. *The procedure required 0.325 +/- .01 grams to be used, but this was misread and 0.254 grams were used instead.

Once the phthalic acid had recrystallized, the experiment shifted back to recrystallizing the unknown compound. Toluene was used in the recrystallization of 0.254 grams (coincidentally the same amount as phthalic acid) of unknown #9. Drops of boiling toluene were added to the solution as it was heated. Once again, the compound was dissolved in the boiling solvent, and, once again, crystals formed very quickly and largely upon cooling. Once they had formed in the flask, suction filtration was used to separate them from the solution, and they were allowed to dry. At the end of the experiment, the melting point of the impure compound was determined twice; the first trial led to a range of 83-86ºC and the second to a range of 83-87ºC. Table 1: Solubility Using 0.25 mL Solvent Results: Table 2: Analysis of both Acid Recrystallizations Solvent Cold Hot Observations Water Insoluble Soluble Precipitates on cooling Hexanes Insoluble Insoluble N/A Toluene Insoluble Soluble Precipitates on cooling (fast) Ethanol Insoluble Soluble Precipitates on cooling (slow) Methanol Insoluble Soluble Precipitates on cooling (very slow) 70% Ethanol Soluble Soluble Did not precipitate upon cooling

Identity a -methyladipic acid (Unk.9) Phthalic acid

% Recovery (mass recovered/ mass used) *

Melting Point (pure) 85ºC 207ºC

Melting Point (impure) 83-87ºC N/A

removing the crystals from the solution also rids the impurities from them. Lastly, the crystals are rinsed with ice-cold solvent, cleaning off any remaining impurities.

  1. The information on the page states that 180 milligrams of phthalic acid will dissolve in 1 milliliter of (boiling) water. 4.2 grams (or 4200 milligrams) of phthalic acid will thus require about 23.33 milliliters of (boiling) water to dissolve (4200 mg / 180 mg).
  2. The information on the page also states that 5.4 milligrams (or 0.0054 grams) of phthalic acid will be recovered in crystal form per 1 milliliter of (cold) water. Multiplying this number by the 23.33 milliliters of water determined from question 3 will provide the amount lost in solution, about 0.126 grams. Subtracting this number from the original 4.2 grams of phthalic acid started with will provide the amount of phthalic acid that will recrystallize, 4.074 grams.
  3. The structural property of sodium 4-amino-1-naphthalenesulfonate that makes it very soluble in water is the fact that it is a salt. It therefore holds the ability to form hydrogen bonds with the polar bonds of a water molecule.