Purpose

Extraction is a method used to separate or isolate a particular component of a mixture. This

process requires a solvent which allows the desired compound (or compounds) to separate from a solid
into a solvent or from a solution into another solvent. In this experiment three compounds were
separated; a neutral compound and two weak acids, these compounds are then measured before and
after the process in order to determine the efficacy of the separation technique.

Reactions

1. Reaction 1: the reaction of p-toluic acid with sodium bicarbonate

2. Reaction 2: the reaction of sodium bicarbonate with acid

3. Reaction 3: the reaction of the major organic product from reaction 1 with hydrochloric acid

4. Reaction 4: the reaction of p-t-butylphenol with sodium hydroxide

5. Reaction 5: the reaction of the major organic product of reaction 4 with hydrochloric acid
Calculations

1. The percent composition of the unknown mixture:

2. The percent recovery of the mixture:

Results

Recovered Mass Percent Composition

p-Toluic Acid 0.7 58.3
p-t-Butylphenol 0.5 41.7
Acetanilide

Discussion

The extraction of p-toluic acid was a result of two chemical reactions. To begin the procedure,
25 mL of t-butyl methyl ether was placed into a 100mL beaker. Approximately 1.5 grams of the
extraction mixture was added and allowed to dissolve; the resulting mixture was then poured into a 125
mL separatory funnel (Reaction 1). Next, 10 mL of 0.5M aqueous NaHCO 3 is added to the ether solution
and mixed and shaken until the mixture is gas-free (Reaction 2). The newly formed solution was allowed
to separate into two layers: an ether layer and an aqueous layer; the aqueous layer was drained, leaving
only the ether layer remaining within the funnel. This process was repeated twice, and two more
portions of 10 mL NaHCO3 were added, mixed, and shaken in order to remove any remaining p-toluic
acid within the ether layer. The addition of 3M HCl to the NaHCO 3 solution caused a reaction which led
to foaming, ultimately resulting in the precipitation of p-toluic acid (Reaction 3). 3M HCl was then
continuously added until no more solid is produced and the solution tests acidic (blue litmus paper turns
red). The mass of filter paper was recorded and then used to separate the crystals from the solution
using vacuum filtration with a Buchnel funnel. The crystals on the paper were placed on a watch glass
and allowed to air dry.

The remaining ether solution in the separatory funnel is then mixed and allowed to react with
10 mL of 0.5M NaOH (Reaction 4). Following this reaction, two layers are formed; drain the NaOH layer
from the separatory funnel into the 100 mL beaker containing the first NaOH extract. Repeat the
extraction of the ether layer by adding a second portion of 10 mL NaOH, and then drain the NaOH layer
from the funnel into the 100 mL beaker containing the first NaOH extract. After repeating this process
with a third 10 mL NaOH portion, the NaOH solution was then heated to about 60°C on a hot plate in a
fume hood. 3M HCl was added to the NaOH solution until it became acidic. Next, the mass of the filter
paper was measured, recorded and then used to separate the p-t-butylphenol crystals from the solution
by vacuum filtration with the Buchner funnel. The paper along with the crystals were placed on a watch
glass and allowed to air dry.
 The ether-acetanilide solution was supposed to be transferred into a clean 125 mL Erlenmeyer
flask and then mixed with approximately 1 gram of anhydrous Na2SO4. In the experiment, NaOH was
added to the mixture instead of Na2SO4 producing no visible reaction. As a result, acetanilide was
unable to be isolated ultimately ruining the experiment.

There are a few measures that should have been implemented to complete the extraction
process. During separation, the NaOH layer within the separatory funnel was not extracted carefully
and precisely, leaving a considerable amount within the funnel. Most importantly, human negligence
accounted for most of the shortcomings during the experiment. The inability to properly follow
directions resulted in the incompletion of the extraction process.

Conclusion

The extraction process was ultimately a failure. Human error was the predominant factor which
led to the incompletion of the extraction process. Consequently, the desired result was not achieved
and the experiment was deemed a failure. Since the experiment was a failure, the analysis of any
substitutes was impossible.