Chemistry 2510 Introduction to Experimental Organic Chemistry Spring 2017

Experiment #1
Recrystallization and Melting Points

Laboratory Notebook: You need to summarize your experimental plan in your lab notebook. Be sure
to include a table of all reagents and compounds that will be used in this experiment, including safety
hazards, physical constants, and other important properties for each.

Laboratory Observations: Be sure to record any observations during the laboratory. You must record
exactly how much of the starting materials you started with and the weight of the isolated product. You
will also want to note the color, shape, and general appearance of the crystals from both methods that
you attempt.

Results and Conclusions: Calculate a % recovery for all methods of recrystallization. You will also
determine the melting points for crystals obtained from both methods. Compare your results and
observations to other students in your lab that have used other methods.

Relevant Reading: Filtration, pp 26-30, Crystallization, pp 121-129 and Melting Points, pp 49-53.

Procedure:
You will be given about 1 g sample of benzoic acid that is contaminated with approximately 5%
salicylic acid. You should record an accurate mass of the starting mixture you are given.

O O

OH OH

OH
Benzoic Acid Salicylic Acid

Part A:
Recrystallize the benzoic acid following the steps outlined below:

a) Dissolve the compound in a minimum of boiling water.

b) Gravity filter the hot liquid (skip if no insoluble impurities are present).
c) Allow the solution to slowly cool to room temperature (at least 20 minutes).
d) Cool the solution in ice for 20 minutes.
e) Collect the crystals by vacuum filtration.
f) Place your crystals in an oven at 90oC on a watch glass to dry for at least 20 minutes.
g) Obtain the mass of your final sample.
h) Determine the melting point of the sample.

Part B:
Repeat the recrystallization on a second sample 1 g of benzoic acid (again recording the mass),
making one of the following modifications.

i. Repeat the procedure exactly as it was done above (repeat steps a-g exactly as above).
ii. Dissolve the compound in 100 mL of water (in place of (a) above).
iii. Dissolve the compound in a minimum of boiling water and then boil the solution long
enough to reduce its original volume to half (insert this after (a) above and skip the
gravity filtration step (step (b) above).
iv. Allow the solution to cool to room temperature for only one minute and then to cool in ice
for 20 minutes (in place of (c) above).

Allow your second set of crystals to dry in an oven at 90oC for at least 20 minutes and then
determine the melting point of the sample.

Questions:

1) Which method produces the highest quantity of crystals?

2) Which method produces the highest quality (taking into account melting point range,
appearance, color, etc.) of crystals?
3) Which method produces the most pure product (as measured by melting point range)?

WASTE DISPOSAL:

Filter Paper: Rinse with water, wring dry, and put in trash.

Water from Recrystallizations: Wash down the sink.

Recovered Benzoic Acid: Wash into Organic Waste bottle.

Used melting point capillaries: Place in the glass waste box.