Experiment 2 Scaffold, Unknown #48
1. The experiment which was conducted was a nucleophilic substitution of one of three
unknown compounds in reaction with benzyl bromide in the vicinity of sodium
hydroxide to synthesize a benzyl ether product. The purpose of the experiment was to
identify our unknown reagent and product.
2. The experiment involved an unknown reactant which could potentially be either one
of three different compounds.
3. The techniques implemented to purify and identify the products of the reaction were
recrystallization and melting point.
4. Pertaining to this experiment, the most significant aspects of nucleophilic substitution
is a leaving group which breaks off an alkyl halide, and a nucleophile which takes its
place through bonding to the alkyl halide. Therefore, one of the experiment’s
reactants must be the nucleophile which reacts with the benzyl bromide to form the
benzyl ether product. Once the product is identified, one can work to identify the
nucleophile responsible for the particular product.
5. In this experiment, melting point was utilized in order to compare the physical
properties of two potentially similar or same solid products. For two solid products,
one can compare the melting points as potential evidence as to whether the solids are
the same. If the melting points are the same, the products may undergo further testing
in order to finalize an identification of their similarities (in this case TLC). If one
product is slightly less than the other, this could potentially entail that there are
impurities in the lesser product which force it to melt quicker than the more pure
product. If the two products are generally not within melting ranges, than the products
are different.
6. The technique of recrystallization was used in this particular experiment to purify the
product from the previous reaction. It is being used because in order to identify the
product of the experiment conducted, it has to be compared to standards provided
from the stockroom. The standards are known and can assist in identifying the
unknown product, however, if the product generated from experimentation is not
pure, it could potentially lead to mixed results. Therefore, recrystallization aids in
purifying the product to be able to provide accurate melting points and TLC distances
for comparison with the stockroom products.
7. Thin Layer Chromatography (TLC) is being used to finalize an identification of the
experiment product and that of which is provided by the stockroom. It is also used to
identify the unknown nucleophile in the reactants. TLC can be used to identify
whether samples are the same compounds based on the polarities of the molecules.
The more polar substances in a TLC travel less distances. Therefore, based on the
distance traveled, or the samples’ polarities, one can tell if they are identical or not.
8. The product that was obtained was 4-tert-butylbenzyl phenyl ether. The unknown
identity of the nucleophile that this product leads to 4-tert-butylphenol.
9. The yield of the product obtained was 1.182g. Theoretically, the yield was 1.79g,
which when divided by the