Lab 9: Qualitative Identification of Organic Compounds Preparation of Derivatives

(3106-9)
Nate Hall (w/Olivia Harris)
T.A.: Shikha Sharma
Purpose: To figure out what two unknown compounds are using classical chemical methods,
like functional group identification and derivative preparation. The derivative tests will confirm
the final identity of the unknowns from the blue notebook and melting point results.
Procedure:
Solid Unknown
1. Put 10 mg of the unknown in a conical vial.
2. Add two drops of methanol and 2 drops of water.
3. Under the hood, add 3 drops of the brominating agent.
4. Keep adding the agent until the reddish-brown color persists
5. Add 4 drops of water, cap the vial, shake, vent, and let it stand for 10 minutes
6. Get the crystals with vacuum filtration in a Hirsch funnel.
7. Wash the filter cake with 0.5 mL of 5% aqueous sodium bisulfate
8. Recrystallize the solid, derivative from ethanol, and dissolve in ethanol and water until it
becomes cloudy.
9. Cool in an ice bath and collect the crystals
10. Dry and collect the melting point
Liquid Unknown
*the process for ketone derivative collection isnt in the book, so Ill ask the T.A. about it at the
lab*

Data:
Melting Points

Solid Unknown*
64.8-69.0

Liquid Unknown Deriv.

242.4-245

*The derivative results were not sufficient to provide data, difficulties described in conclusion
Possible Compounds (in order of likelihood)
Liquid Unknown
Benzalacetophenone
m.p. 58 C
Benzoin
m.p. 133 C
Benzophenone
m.p. 48 C
Solid Unknown
4-bromo phenol
m.p. 66 C

Derivative mp (C)
245
245
239
Derivative mp (C)
95

Conclusion:
The final part of the qualitative identification experiment was difficult for the solid
unknown, but yielded proper results for the liquid unknown. When dealing with the solid
derivative procedure, the crystals left after the first filtration were very little. This made
recrystallization very difficult, and even with a sufficient amount of raw crystal (according to the
T.A.) recrystallization could not be achieved. Thus, another process was done to find melting
points of merely the crystals after vacuum filtration, of which very little were produced. The
crystals melted instantaneously however at 55 C, indicating that they were not dried enough
and that other compounds had melted instead of the crystals needed. After consulting with the
T.A., it was decided that just the melting point from part one of the experiment would have to be
enough. As such, the solid was identified as 4-bromo phenol, since 66 was in the right melting
point range that was recorded from before. The liquid derivative was produced according to
plan, and an accurate melting point range was recorded. The most likely compound was the
benzalacetophenone, since it had a low melting point, and the derivative number was exactly in
the melting point range. The benzoin was second due to its higher regular melting point. Lastly,
the benzophenone could also be an option, though the derivative melting point is technically out
of the recorded range for the experimentally prepared derivative.