Synthesis and Chemistry of Alkenes
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As the borate ester complex reaction proceeded in the experiment, the solution went from a bright yellow color to a light milky yellow color in the addition of sodium borohydride. When acid was added, it turned from a liquid yellow to a solid precipitate (solid ) yellow compound. It thickened as it was swirled.
In comparing the IR spectrum of the 9- fluorenone and 9- fluroenol, there were disappearance and appearance of certain peaks. For the fluorenone IR seen on the Chemistry 232 Lab website, the peak at around 1723 cm-1 for carbonyl (C=O) , had disappeared on the IR for 9-fluorenol. Also the appearance of a peak around 3400.92 cm-1 for hydroxide group stretch was found in 9-fluorenol. All other main peaks for the two compounds were very close in value. The disappearance of carbonyl bond tells us that this bond was broken during the reaction in order to form the hydroxide group: appeared on the 9- fluorenol IR. The comparison in peaks is presented In table 1. The observed melting point range for collected recrystallized 9-fluorenol was found to be 149-152 was lower and wider in range than the literature value of 153- 154; the different in values could have been to impurities in the sample .
In comparing the given nmr spectra of 9-fluorenone (reactant ) and 9- fluorenol ( product) , it was see that the chemical shift of the aromatic protons was caused by the change in function group on the middle aromatic ring. The appearance of a peak around 5.6 ppm on the 9-fluorenol nmr demonstrated the presence of a hydroxyl proton which ranges in literature from 1- 5 ppm. Also the presence of the a peak between 1.6 and 2.0 was seen on only the 9-fluorenol, which concluded an H proton on the carbon. Both these proton groups were not apparent in the 9- fluronone.