Recrystallization Activity

Name _______________________________ Lab Partner ____________________________
Recrystallization Activity
In today’s activity, you will be working with a partner to recrystallize an impure sample of acetanilide.
1. Begin by filling out your title and purpose in your lab notebook.
2. What are the characteristics of a good recrystallizing solvent?
3. Now you will be performing tests to choose your recrystallizing solvent. Prepare a boiling water bath in a medium-
sized beaker for use in part (c) below. Then, follow this procedure: (Make sure you record this procedure and your
observations into your notebook)
a. Take three reaction tubes and weigh out 20 mg of acetanilide into each tube.
b. Add 0.5 mL (use the markings on your reaction tube to measure this) of the first potential recrystallizing solvent,
methanol, to a reaction tube. Stir the solution and record whether the solid dissolves.
c. If the solid does not dissolve, place it in a boiling water bath to heat it up (don’t forget to put a boiling stick in the
tube). Stir and observe the solubility in the hot solution. Then cool to make sure your solid reforms as crystals.
d. Repeat this process for each of the other potential recrystallizing solvents. You should be testing water and
petroleum ether.
4. Based upon these tests you just performed and your observations, what will you use as your recrystallizing solvent?
Explain why you chose it.
5. Use the Merck index to find the melting point of acetanilide and its’ solubility in your chosen solvent under hot
conditions. Use this solubility to calculate the approximate volume of solvent you will need to use to recrystallize
200. mg of acetanilide. Show your calculation below.
6. You and your partner now need to develop a procedure to recrystallize 200 mg of acetanilide. Discuss your
procedure and write a rough draft on a scrap sheet of paper.
7. Have your procedure checked by the instructor. When the instructor approves your procedure, perform your
recrystallization. Make sure you record your procedure and your observations in your lab notebook.
8. Upon completion of your recrystallization, determine the percent recovery of acetanilide. Show your calculation
below.
9. Analysis. (One person should perform TLC while other performs m.p.)
a) Determine the melting point of the purified and of the impure acetanilide. Record below.
b) Perform TLC analysis of the impure acetanilide and the purified acetanilide samples using a
silica plate. Dissolve a small amount of each sample in a small amount of ethyl
acetate to use as your spotting solutions. Ethyl acetate is also the TLC developing solvent.
After the plate is run, allow solvent to dry completely. Check for spots by first using UV light,
and then dip plate in the bromocresol dye chamber. Circle the spots and calculate
Rf values. Fill in the blank plate on this sheet with your results, labeling R f values. Sketch the
plate in your notebook as well.
10. Given all of your data, how can you tell that your recrystallization was successful in purifying the acetanilide? You
should discuss at least two different types of data to support answer for full credit.
Questions
1. A student attempted to perform a recrystallization but after dissolving his acetanilide in an appropriate hot solvent,
the sample did not form crystals when it was cooled in an ice bath. What is the most likely thing that the student did
incorrectly and how can he correct this error (without starting over)? What should he do in the future to try to
avoid this error?
2. Another student chose a recrystallizing solvent in the following way: He performed the same tests as you did above.
He then chose a solvent that he observed caused the solid to dissolve right away at room temperature. After
attempting to perform the recrystallization, he failed to recover any solid product. What did this student do wrong?
How can he correct his error (without starting over because this is a valuable solid and he doesn’t have any more)?
3. A student performs a recrystallization. She has cooled the solution, but her crystals are very powdery and not well-
formed when they should be more needle-like. She has not yet collected them by vacuum filtration. What was the
most likely mistake the student made? How can the student correct this error (without starting over)?
4. A student finishes her recrystallization and finds that she has 110% recovery and the melting point is very low.
Assuming that she performed her calculation and melting point correctly, what is the most likely error the student
made? How can she correct this?
Submit this document as your report using the Report Submission link on Canvas. Submit your notebook pages using
the Notebook Submission link on Canvas.

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Name ___ Lab Partner

2. What are the characteristics of a good recrystallizing solvent?

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