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Autor: jordyng • February 29, 2012 • 381 Words (2 Pages) • 841 Views
Object: To reduce 9-flurenone to 9-fluorenol with the use of sodium borohydride, sulfuric acid to collect a precipitate and methanol and a reflux apparatus in order to purify a recrystallized product.
Reagents & Products:
Compound MW (g/mol) Used Moles Physical & Safety Data
9-fluorenol 182.22 - - mp. 153-154˚C. Irritant, white powder.
Ethanol 46.07 10mL 0.324 bp 78˚C, d 1.492g/mL. Flammable liquid, irritant, Dispose in non-halogenated waste bin.
Sulfuric acid 98.08 2mL 0.006 bp. 270-340˚C, d.1.84g/mL, corrosive irritant. Dispose of in non-halogenated waste bin. Concentration 3M.
Sodium borohydride 37.84 0.0946 0.0025 Solid flammable corrosive irritant dispose of in halogenated waste bin. No melting point it decomposes
9-fluorenone 180.21 0.901 0.0050 bp. 342˚C mp. 83.5˚C, irritant that may be combustible at high temperatures.
Methanol 32.04 10mL 0.247 bp. 64.7C, d. 0.791g/mL, Flammable liquid toxic, dispose of in non-halogenated waste bin.
Procedure Reference: Peter Marrs, Chem 232 Lab Manual, pp.53 (University of Victoria, BC). Spring2011.
Mass of 9-fluorenol product 2.07g
Melting range of 9-fluorenol product obtained 145-150˚C
Literature value for melting range of 9-fluorenol 153-154˚C
Ir Analysis of Nujol
Wavenumber (cm-1) Relative Intensity Assignment and Comment
2923,2853 Very strong sp3 C-H stretch
1456 Strong CH2,CH3 bending
1377 Medium CH3 symmetrical bending
In the Infrared spectrum obtained for the 9-fluorenol product there was a significant different from the 9-fluorenone spectrum in the fact that there was no sharp carbonyl peak around 1700 cm-1. Also there was a broad tongue shaped peak around 3550-3200cm-1 depicting an alcohol stretch in the 9-fluorenol spectrum. Also deep sharp peaks present around 3000cm-1 are in both spectra due to the Nujol reagent and should be disregarded.
The proton nmr spectra for 9-fluorenone and 9-fluorenol differ in the sense that 9-fluroenone has no chemical shifts other than a series of doublets 7-7.8ppm. 9-fluroenol however not only has proton shift activity between 7-7.8ppm but two separate doublets at 5.6 and 1.9. These doublets