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Experiment 3: Resolution of ()--phenylethylamine

Presley Sylvester-Omorodion
Student Number: 215347057
Friday, March 17, 2017
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Results:

Reagents Used in Amounts Used and

Experiment Collected
()--phenylethylamine 9.4 g (10 mL)
(+)-tartaric acid 12.0 g
Methanol, CH3OH 165 mL, 10 mL, 10 mL
(-)--phenylethylamine-(+)- 6.37 g
tartrate salt
Dichloromethane, CH2Cl2 10 mL, 10 mL, 5 mL
2M Sodium Hydroxide, 30 mL
NaOH
Potassium Carbonate, Approx. 1.0 g
K2CO3
(-)--phenylethylamine 1.42 g
(isolated)
[]observed for (-)-- -37.23
phenylethylamine

Questions:
1. Draw the chemical structures of the two diastereomeric salts produced in Lab 1
using a proper line-angle representation.
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2. Based on the mass of ()--phenylethylamine you started with, calculate your

percentage yield of your final product after the extraction. Why would a product
yield of 100% be undesirable in this experiment?
The amount of 10 mL of ()--phenylethylamine was used in Lab 1. The density
was found to be 0.94 g/mL (REFERENCE) therefore the theoretical yield of ()--
phenylethylamine is:

Mass = Density x Volume

Mass = 0.94g/mL x 10mL
Mass = 9.4g of ()--phenylethylamine

The amount of percent yield of the (-)--phenylethylamine can calculate from the
()--phenylethylamine solution:

% Yield= (Actual Yield/Theoretical Yield) x 100%

% Yield= (1.42g/ 9.4g) x 100%
% Yield= 15.11 %

A product yield of 100% is undesirable in this experiment due to the fact that the
()--phenylethylamine is a racemic mixture consisting of both enantiomers (R and S).
Because only the (-)--phenylethylamine was crystallized with the tartaric acid and
isolated by filtration, the enantiomer of (+)--phenylethylamine salt solution is more
soluble therefore staying in solution and was disposed of, therefore losing most of the
original yield/mass. (-)--phenylethylamine yield is then compared to the ()--
phenylethylamine yield.

3. Calculate the optical purity (enantiomeric excess) of your final product

Optical Purity (%) = ([]observed / []D20) x 100%
Optical Purity (%) = (-37.23 / -40.4) x 100%
Optical Purity (%) = 92.15 %

4. What organic compound remains in the aqueous layer during the extraction?
Why does this compound dissolve easily in high pH solutions but not as much in low
pH solutions?
In the experiment the organic solvent dichloromethane is used to extract the
neutral (-)--phenylethylamine from the aqueous extract of NaOH-salt mixture because
the (-)--phenylethylamine is more soluble in dichloromethane than the former mixture.
Therefore, all that is left in the aqueous layer is the sodium tartrate. This compound easily
dissolves in high pH due to the fact that the tartrate compound is very acidic with it being
diprotic acid, therefore taking part in the chemical equilibrium and binds to the strong
base of sodium hydroxide.

5. If you wanted to isolate (+)--phenylethylamine, how could you change your

experimental procedure to accomplish this? Please note you must still use (+)-
tartaric acid in the initial step.
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12.0 g of tartaric acid solution will still be added to with the racemic ()--
phenylethylamine. Crystallization will occur as usual. Due to the fact that the (-)-amine-
(+)tartrate salt contains the (-)--phenylethylamine during the crystallization process, the
more soluble (+)--phenylethylamine will be left over in the mother liquor. This liquid
solution can be isolated again using a Buchner filtration funnel to remove crystals. The
Crystals are discarded because they contain the (-)-free amine. Add an aqueous solution
NaOH to remove the tartaric acid from the amine creating sodium tartrate. Extract the (+)
free amine by using a more soluble solution than NaOH solution.

6.a) What would be the outcome of this resolution experiment if (-)-tartaric acid was
used as the resolving agent? Please explain your answer.
b) What would be the outcome of this resolution experiment if meso-tartaric acid
was used as the resolving agent? Please explain your answer.
The outcome of this resolution experiment would be the same due to the fact that
(-)-tartaric acid is still a chiral acid. By using (-)-tartaric acid it will just give different
diastereomers of the amine-tartrate salt, instead of producing a RRR and SRR salt
complexes, RSS and SSS salt complexes will be formed. Isolation and extraction can be
performed to isolate (-)--phenylethylamine. A meso-compound of Tartaric acid is also
known a diastereomer of that compound. This molecule although has a plane of
symmetry, therefore it is an achiral molecule. It is known that in resolution of any ()-
amine, the resolving agent must be chiral compound; in the case of the experiment, a
chiral acid [(+) tartaric or (-) tartaric]. Enantiomers of a compound have identical
physical properties in an achiral environment. Therefore, using an achiral acid instead of
a chiral acid, separation of the racemic amine mixture into its enantiomers is impossible.

Reference
Wade, L. G. (2013). Organic Chemistry (custom edition for York University) (Vol. 2).