3-Nitroacetophenone Synthesis Lab Report

40 mL of concentrated hydrochloric acid was slowly added to 2.0g of m-nitroacetophenone and 4.0g granular tin. There were bubbles and foaming so the addition was done 2 mL at a time with a disposable plastic pipette. The solution was stirred with a magnetic stir bar on a stir plate set to medium intensity. After all the hydrochloric acid was added, the solution was heated and stirred on the hot plate for 30 minutes. The solution required a full 30 minutes because the tin needed to dissolve. The reaction mixture was cooled in an ice bath for 10 minutes and then 1 mL of 10M sodium hydroxide was added at a time until the pH was basic. In total, 15 mL of sodium hydroxide was added until the pH was about 10. A piece of pH paper was inserted into

For the metal/acid reduction of nitro compounds performed the first week, the known compounds of 3-aminoacetophenone, 3-(1-hydroxyethyl) nitrobenzene, 3-(1-hydroxyethyl)aniline, and ethanol were also dissolved in 2 mL DCM. The dissolved mixtures were placed onto a prepared TLC plate that had 1 cm lines from the top and bottom as well as 5 lanes marked, using a capillary action tube. A TLC chamber was prepared using about 10 mL 97% DMC/3% methanol solution, filter paper, and a watch glass. The DCM/methanol solution was poured into a 250 mL beaker, the filter paper placed on the side, and the watch glass placed upside down over the top. Then, when the filter paper was completely saturated with the solvent, the TLC plate was inserted vertically into the TLC chamber and the watch glass replaced over the top. The apparatus sat, untouched for about 15 minutes, until the solvent reached 1 cm from the top of the TLC plate. The same process was used for the TLC of the reduction of sodium borohydride except that the isolated product was compared to 3-1-hydroxyethylaniline, 3-nitroacetophenone, 3-aminoacetophenone, and 1-(3-nitrophenyl)ethanol. After the solvent had reached the top of the TLC plates, they were placed under a blacklight and the paths substances had traveled were circled and measured. The Rf values were recorded in the lab