Aleks Glod

Organic Chem 2211L

January 28, 2017
TA: Lauren Pepi
I.Title: Using Recrystallization and Melting Point Determination to Isolate and Identify an
Unknown Compound from an Impure Mixture
II. Introduction: Students will apply the techniques of recrystallization, filtration and melting
point determination in order to purify an unknown substance and identify it. The unknown
substance will undergo recrystallization, which removes impurities from the solid, in this case to
remove sand from the unknown. Following recrystallization, the compound will be dried by
suction filtration. This is important because trace liquid solvent may be left over after
recrystallization. Melting point determination is used to identify the unknown substance after it is
dried. By comparing the value found in literature, to the value determined from melting the
unknown substance, it can be then properly identified.
III. Table of Reagents:

Compound Name Structure Molecular Weight Melting Point ( C )

(g/mole)

Acetanilide

Benzamide

Benzoic Acid

Ethyl 3,5-
dinitrobenzoate
Compound Name Structure Molecular Weight Melting Point
(g/mole) (C )

m-nitrobenzoic acid

o-Toulic acid

Salicylic acid

Vanilin

IV. Safety Information: This experiment involves boiling water, potentially dangerous
chemicals, and hot glassware. Safety glasses and lab gloves should be worn during
experimentation.
Hot glassware: Never heat a closed vessel, pain and burning will occur
without proper protection. Always test temperature before handling
glassware.
Boiling liquids: Add boiling chips to any liquid before heating, pain and
burning will occur if handled without protection, always test temperature
before handling and watch to ensure liquids do not boil over.
Use thick rubber hose not thing latex tubing when using the Buchner
funnel. Make sure to securely attach the filter flask with the ring stand prior
to connecting to the vacuum hose and add the neoprene adaptor.
 Mel-Temp Apparatus: Do not place a new sample into the apparatus if it is
already hot. Never touch the Mel-Temp heating block while being used or
cooling off.
Chemical Safety:
Acetanilide: Hazardous if it comes in contact with eyes, if ingested or inhaled can cause skin
irritation.
Benzamide: Ingestion can cause diarrhea, vomiting and nausea; contact with eyes may cause
tearing or redness; contact with skin may cause redness, itching or pain; inhaling benzamide may
cause coughing or shortness of breath.
Benzoic acid: Severe eye irritation if comes in contact with eyes, inhalation of gas may cause
tearing, contact with skin or absorption may cause an allergic reaction and labored breathing.
Ethyl 3,5-dinitrobenzoate: Serious irritation and redness if come in contact with eyes; if ingested
orally may cause intense irritation of digestive tract.
m-Nitrobenzoic acid: Unconsciousness and convulsions due to ingestion; inhalation causes
wheezing, coughing and burning of mouth and throat; skin may become red and irritated.
o-Toluic acid: Harmful if swallowed, leading to digestive tract irritation causing diarrhea; the
respiratory tract may become irritated upon inhalation.
Salicylic acid: High concentrations can lead to moderate degree chemical burns; if ingested, can
induce transient hearing loss
Vanilin: May trigger migraine headaches in certain individuals; dust may cause mechanical
irritation in the eyes and skin.
V. Experimental Procedure:
1. Obtain one gram of the impure, unknown solid. Record your specific alphanumeric code in
your data section.
2. Stir the mixture before measuring out the sample.
3. Add about 20-25 ml of water, along with a few boiling chips to a 125 ml Erlenmeyer flask.
4. Gently boil the water using a hotplate, do not overheat because too much water may evaporate
from the flask.
5. Put a 125 ml Erlenmeyer flask on another hotplate containing one gram of the unknown
substance and some boiling chips.
6. Pour boiling water into the flask, the amount can be estimated between 5-10ml but does not
need to be measured.
7. Keep the flask on the hotplate while swirling the mixture for about one minute. If the solid is
not dissolving, about 3-5 ml of boiling water can be added until it completely dissolves. Upon
each addition, the mixture needs to be stirred another minute.
8. Any clumps during the process should be broken down using a stirring rod or a spatula.
9. Next, construct a gravity filtration system (Figure 1). This consists of a short stem funnel line
with folded filter paper (Figure 2), covered with a watch glass and is placed on top of a 125 ml
Erlenmeyer flask containing a few ml of boiling water. The temperature of the water needs to be
maintained with the help of a hotplate.

Figure 1: Gravity Filtration System

Figure 2: Proper filter folding technique

10. Moisten the folded filter paper before filtration with a small amount of water. Rinse with 2-3
ml of boiling water after filtering.
11. After removing the flask from the hotplate, let the filtrate slowly cool to room temperature.
12. Upon reaching room temperature, inspect for crystal formation. If no crystals are found, use a
stirring rod to carefully scratch the inner flask wall. Leave to flask to rest until crystals are
formed.
13. Let the flask with the newly formed crystals sit in an ice bath for 5-10 minutes to finish
precipitating. Ensure the temperature drops consistently by submerging the entire portion of the
flask. If no more crystals appear, the water volume needs to be reduced, once again by heating it
up with a hotplate. Then attempt to recrystallize the solution again.
14. Next, assemble a suction filtration system (Figure 3). Place a moistened filter paper in the
bottom of the Buchner funnel. With the neoprene adapter seal the funnel to the 250 ml flask
placed underneath. Attach the filtration flask using a ring stand and clamp. Using a rubber, thick
vacuum hose attach the flask to the water aspirator.

Figure 3: Suction Filtration System

15. Being careful not to overfill the funnel, slowly pour the sample down the funnel. Wait for
each pour to be filtered before adding more. Continue until all has been filtered.
16. Remove final impurities by washing the remaining crystals with 2-3 ml of cold water.
17. Dry the crystals for 10-15 minutes using the vacuum.
18. Scrape the crystals from the filter paper onto a watch glass. Use a heating lamp for several
minutes if the sample has not dried yet. Then measure the mass of the sample.
19. Prepare a melting point sample to be placed into the Mel-Temp
20. Place some fine powder sample onto the watch glass. Then load into the capillary tube, close
it, then place in the condenser. Allow to bounce until the sample has settled to the closed end.
21. Watch for the first drop of liquid to from in your sample, the again for when it completely
becomes liquid. Record the data for those temperatures.
22. Insert a thermometer and ample capillary into the Mel-Temp Apparatus.
23. Heat the sample at 6-8 C per minute to approximate the melting point range.
24. Lower your heat setting to 1-2 C per minute and perform a second trial with a different
sample. Heat the sample to within 20 C of the original melting point.
25. Identify the two substances listed on the table of reagents with similar melting points,
approximate temperatures to the sample.
26. Conduct a mixed melting point experiment by melting a 50:50 mixture of your unknown and
the standard sample you think your unknown may be. Put into the Mel-Temp and determine their
melting point ranges.
27. If the melting point variance is 5 C or greater, repeat the mixed melting point experiment
using the standard sample with next closest melting point. Record your data.