Thin Layer Chromatography

By:
Richard M DeCola, decolar@go.stockton.edu
CHEM 2125 008
9/26/18
Abstract:
Identification of an unknown solid was determined by using a mixture melting point in a
Thomas‐Hoover apparatus. The melting point (mp) range for the pure unknown #7 (94‐97°C) was
observed and then compared to a set of known chemicals with similar mp. The known solids
(m-toluamide, 94‐96°C; Methyl-4-nitrobenzoate, 94‐96°C) were each mixed with the unknown and a
mixture mp taken. The unknown has been determined as m-toluamide due to the similar 94‐96°C mp
observed when an unknown/m-toluamide mp sample was tested.

Purpose/Theory:
The melting point of a substance is a physical property which can be used to provide information about
the identity and the purity of a solid. A solid usually melts over a range of temperatures rather than at one
specific temperature. A narrow melting range (4°) typically implies an impure compound. In this
experiment, the identity of an unknown organic compound will be determined using a mixture melting
point methodology. The melting points of a mixture of the unknown with different known compounds
will be taken using a Thomas‐Hoover apparatus. If the melting point of the mixture is the same as that of
the known compound, then the known and the unknown are most likely identical. A decrease in melting
point of the mixture and a broadening of the melting point range indicates that the compounds are
different.

Results and Discussion:

 The above data supports unknown #24 to be m-toluamide. When m-toluamide is mixed with the
unknown the mp was 94-96°C. The pure unknown had a similar 94-97°C mp. Both of these results are
very similar to the literature reported value of 94-96°C for pure m-toluamide.

The unknown #7 could not be Methyl-4-nitrobenzoate due to the disparity with observed mp.
Although the literature value for Methyl-4-nitrobenzoate (94-96°C) is close to the pure unknown mp (94-
97°C), when they are mixed the observed mp is significantly lower at 73-76°C. This proves the sample to
be a mixture and not a pure sample.

Conclusion:
The unknown #24 is m-toluamide. Mixture melting point observations support this statement.
When a known compound is mixed with the exact same compound in unknown form, the resulting mp
should be exact to the literature value as it is in this case. Here it is observed that an unknown #24 and m-
toluamide mixture results in a mp of 94-96°C which is the same as m-toluamide’s reported 94-96°C
value.
References:

Zubrick, James. The Organic Chem Lab Survival Manual, 9th ed.; Wiley: NJ, 2014.

Griffiths, J.; Overley, K.; Broughton, S. Introductory Organic Laboratory – Techniques and
Transformations, 6th ed.; Rajaraman, R. Ed.