CM2191 – Grignard Experiment

Product obtained is P-Toluic acid, based on its melting range of 176.1-177.7C. The purity of
the final product can be considered pure as it had a very narrow melting range of 1.6C and
corresponds to its literature values of 177-180C. However, we can further increase the purity
of the product by improving the recrystallization process. Recrystallization purifies the solid
product by a slow selective generation of crystals, mostly free of impurities. It is only
effective if done properly. Poor recrystallization technique includes rapid cooling, over
evaporation of solvent, bad choice of solvent, etc. Crystals have specific shaped units and
need time to pack in nicely with each other to form large and pure crystals. Hence, the faster
the crystals grow, the greater the chance of impurities getting trapped within the crystal
framework via the inclusion, occlusion and adsorption mechanism. My final product obtained
from recrystallization was in a form of fine powdery crystals as my solution was not totally
cooled to room temperature before placing it in an ice bath. Therefore, the crystals grew
rapidly, producing tiny powder-like crystals and in the process reducing the purity of the
crystals.

Furthermore, the experimental yield of 30.2% is lower than expected. This might be due to
too much ethanol added while dissolving the bigger pieces of crude product in the two
solvent system. Hence resulting in the loss of product in solution. One way to resolve this
issue is to gently heat the crude product and ethanol mixture while adding warmed ethanol
into the flask. This helps the bigger pieces of crude product to dissolve easily, reducing the
amount of ethanol added.

And as mentioned in the lecture notes, this reaction is best done in an inert gas system
because oxygen in the atmosphere might react with the grignard reagent by inserting an O
atom between the carbon base and the magnesium bromide group. This will decrease the
amount of Grignard reagent available to react with CO2.

In conclusion, the experiment was successful as far as purity is concerned. The yield can be
improved by taking more care in preparing and collecting the product.