Lab 3: Recrystallization (Exp.
3105-3)
Nate Hall (w/Kevin Guerra), Chem 3105
T.A.: Wei Ma
Purpose: To find out the identity of the unknown compounds from last lab using melting points.
Physical Properties Table (no reactions):
Compound MW Amount mp (C) bp (C) density
Naphthalene 128.17 78-80
Biphenyl 154.21 68-70
Benzoic Acid 122.12 120-122
o-Chlorobenzoic 156.57 140-142
Acid
Ethanol 46.07 78 0.789
Safety Information:
Naphthalene
- Flammable
Biphenyl
- Acutely toxic, skin and eye irritant, and skin sensitive
- Acutely and chronically hazardous to the environment
Benzoic Acid
- Acutely toxic, skin and eye irritant, and skin sensitive
- Corrosive to metals and skin, serious eye damage
o-Chlorobenzoic Acid
- Acutely toxic, skin and eye irritant, and skin sensitive
Ethanol
- Very Flammable
Procedure:
1. Weigh the crude hydrocarbon and crude acid solids from last lab
2. Start recrystallization process for the hydrocarbon by putting 50 mg of it into a shell vial
3. Add 1 ml ethanol to the vial and heat to boiling
4. Once the material is entirely dissolved, add drops of water, but stop before reaching a
persistent cloudiness
5. Cool the solution (possibly with an ice bath) to room temperature
6. Collect the crystals using filtration (vacuum or gravity) then dry the crystals and take their
melting points
7. With the crude acid, use water with heating
8. Add ethanol just enough to dissolve the solid, then cool and collect crystals, take melting
points, etc.
9. Dry the crystals by blotting on filter paper before taking melting points
10. Make sure to take melting point ranges of the following: your unknown mixture, the crude
hydrocarbon and acid, the recrystallized hydrocarbon and acid, and mixed melting points
with an authentic sample of the hydrocarbon and acid identified.
Data Table:
Compound Melting Point Range
Unknown Mixture (#5) 68-69
Crude Hydrocarbon 69-70
Crude Acid 141-143
Recrystallized Hydrocarbon 67.6-69.3
Recrystallized Acid 139.5-141.3
Mixture of Recrys. Hydrocarbon and Pure 69-72
Sample
Mixture of Recrys. Acid and Pure Sample 140.7-143.1
Conclusion:
The identification of the two unknown components of the unknown sample (#5) was successfully
confirmed with little doubt from the experimental data. The recrystallization of the hydrocarbon
was made more difficult by how hard it was to know when enough water had been added (i.e.
when the solution had just about reached persistent cloudiness), but both recrystallizations
yielded a good amount of pure crystals to use in determining melting point ranges. The ranges
measured indicated that the components in question were o-Chlorobenzoic acid and Biphenyl
(the acid and hydrocarbon, respectively), and this theory was further confirmed with the
measured melting point ranges from the pure substance mixtures. Measuring the melting point
ranges also was a possible source of error, since the viewer had to record a data point right
when the substance started melting, which was sometimes unclear, and altered by the rate of
temperature increase on the measuring equipment.
Post-Lab Questions:
1. The components of the unknown were biphenyl and o-chlorobenzoic acid, based on
comparing the data for the melting point ranges to the table at the beginning of the lab
report.
2. Impurities will lower the melting point, and expand the melting point range. The range
measured for the unknown sample was indeed lower than the actual melting points of
the components. However, the range was not at all larger than the later recorded
ranges, probably due to human error (i.e. not being able to identify the starting or ending
of the melting of the substances in time, etc.).