Results and Calculations
Rf values
Rf=(Distance moved by the spot (cm))/(Distance moved by the solvent front (cm))
Toluene:
Rf=2 cm/3.8 cm=0.53 (Fluorenone)
Rf=1.1 cm/3.8 cm=0.29 (Fluorene)
Hexane:
Rf=1.8 cm/2.2 cm=0.82 (Fluorene)
Rf=0 cm/2.2 cm=0 (Fluorene
Table 1: Experimental IR peaks compared to literature IR peaks for fluorenone
Functional group
Experimental peak (cm-1)
Literature peak (cm-1)
C-H
3010.5
3013
C=O
1715.2
1715
C=C
1599.6
1600
Table 2: Experimental IR peaks compared to literature IR peaks for fluorene
Functional group
Experimental peak (cm−1)
Literature peak (cm−1)
C-H
2956
Not present
C=C
1477
Not present
Discussion
As indicated by the diagrams above, both TLC plate tests went as expected and showed that the separation went very well. For the TLC plate in toluene, both the fluorene and fluorenone shifted, but the fluorenone shifted farther. This is expected since the polarity of toluene and fluorenone are more similar. However, since fluorene shifted to some degree as well, this indicates that fluorene is slightly soluble in toluene. Since the Rf values are 0.53 for fluorenone and 0.29, the test went as expected since fluorenone is more soluble in toluene. For the TLC plate in hexane, the fluorene moved up while the fluorenone stayed on the line, which was expected. The Rf values were 0.82 for fluorene and 0 for fluorenone. Overall the purpose was fulfilled as the TLC plates indicate that the two substances were separated well and also the IR spectra indicate that the experimental IR is very similar to the literature value.
An IR spectra was obtained for fluorene. Unfortunately, the experimental IR spectra did not even remotely match the IR spectra from the literature values. For instance, in the literature IR, a peak at 2956 cm−1 and 1477 cm−1 represent the C-H and C=C bond, respectively. These peaks are not present on the experimental IR. Also,
References: http://sdbs.db.aist.go.jp (National Institute of Advanced Industrial Science and Technology) July 9th, 2014