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Ketone Reduction

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Autor:  jordyng  29 February 2012
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Ketone reduction

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.

Reaction:

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.

Observations Data:

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 indicate vinylic and allylic protons respectively. The vinylic shift could be caused by the alcohol group in the middle ring of 9-fluorenol whereas the allylic shift is likely due to the double bonds found in the two outer rings of 9-fluorenol. The activity between 7-7.8ppm for both of the spectra portray Aromati ...



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