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Lab 2

Lab 2

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Introduction

The purpose oI this experiment is to separate enantiomers oI (_)-u-phenylethylamine
which contain equal amount oI both (¹) and (-) enantiomers. Both the (¹) and (-) enantiomers
possesses mostly identical physical and chemical properties and only distinguishable in the
behavior in a beam oI a polarized light. When a beam oI polarized light passed through (_)-u-
phenylethylamine, the polarization plane rotated in equally opposite direction which results in
zero speciIic rotation and (_)-u-phenylethylamine is optically inactive. In order to Iorm an
optically active enantiomer, this racemic mixture are reacted with one enantiomer oI a
dissymmetric acid such as tartaric acid (¹) which produces diastereomeric salts such as (¹)(¹)
salts and (-)(¹) salts. Reactions oI these diastereomeric salts with methanol results in the
diIIerence in the solubility between (¹)(¹) salts and (¹)(-) salts which turns out the (¹)(-) salts
less soluble in methanol than (¹)(¹) salts. Thus, this pure stereoisomeric (¹)(-) salt reacted with
NaOH which Iorms pure enantiomer oI u-phenylethylamine. Finally, the concentration and
speciIic rotation oI the pure enantiomer is determined (Wade 2010).







#08ult8
Table 1.1 : Mass oI amine




Table 1.2: Mass oI the enantiomeric salt and the ° yield oI the isolated amine obtained.
Mass oI (-)-amine-(¹)-hydrogen tartrate salt (g) 7.350
° Yield Ior () u- phenylethylamine salt 34.52
° Yield Ior the isolated (-)-u- phenylethylamine salt 23.29


Table 1.4: The observable reaction during the separation oI the enantiomeric amine.




Mass oI 50 mL ¹ 2 boiling chips (g) 28.95
Mass oI 50 mL ¹ 2 boiling chips ¹ amine (g) 31.41
Mass oI amine 2.48

AIter venting the Iunnel

Two distinct layer oI solution Iormed in a mixture.
An opaque layer which consists oI small portion
while another clear layer which consists oI lager
volume.

Addition oI water droplets

The opaque layer stays on top and the clear layer at
the bottom.
Addition oI methylene chloride Colour changes Irom colorless to cloudy

AIter boiling

The boiling only stops when there were only 5 mL oI
solution in the beaker which indicate all the
methylene chloride being removed.
Table 1.5: Polarimater reading and calculation oI the optical purity oI the isolated amine.





Polarimeter reading ( o
589
) -ŷŵ.źŴ°
SpeciIic rotation oI obtained enantiomer |o]
x
t
-ŷŷ.źŶ°
Optical purity oI isolated amine 83.21°
i8cu88ion8
First oI all, only 7.350g salt (-)-u-phenylethylamine obtained where there should have
been 21.294g oI that salt. This very low yield due to evaporation oI (-) salts Iorm the Ilask during
the heating oI the mixture oI (_)-u-phenylethylamine with tartaric acid in the steam bath.
Moreover, this low yield caused by less eIIicient handling oI crystals, some crystal lost when
transIer them to weighing paper to measure. Nevertheless, some crystals sticks with stirring rod
and dried up when the stirring rod is used to handle the crystals (Wade 2010).
AIter venting the separatory Iunnel, two distinct layers oI aqueous and organic align
themselves in two diIIerent positions. In order to identiIy the organic and aqueous, droplets oI
water were added. Since the water remained on the top oI the opaque layer (aqueous), then the
clear bottom part is assumed as organic layer because the organic repels the aqueous. Moreover,
this special aqueous-organic alignment due to density oI organic layer much higher than density
oI aqueous layer, thereIore, less dense aqueous layer Iloats above the organic layer (Wade 2010)
The observed optical rotation oI experimentally isolated amine is -31.60° which means
the isolated amine is levorotatory which rotates 31.60° in anti-clockwise direction. The length oI
the sample cell in the polarimeter is 1 decimeter and density oI the isolated amine is 0.94 g/mL,
the observed speciIic rotation under these speciIied condition is -33.62°. The calculated optical
purity oI the amine is 83.21° which means the (-)-enantiomer Iound in larger extend oI
concentration than the (¹)-enantiomer by 83.21°.. Thus, about 8.395° oI equal enantiomer (¹)
and enantiomer (-) present which will give about 91.605° oI (-)-enantiomer and 8.395° oI (¹)-
enantiomer. Hence, we can conclude that the racemic mixture was completed oI 91.605° (-)-u-
phenylethylamine and 8.395° oI (¹)-u-phenylethylamine (Harris 2010)
"u08tion8

1)

Mandelic acid Malic acid

The chemist can only use either mandelic acid or malic acid to resolve an anime. This is
because both mandelic acid and malic acid have an asymmetric carbon bonded to Iour diIIerent
groups which showed with arrows and moreover, both acids does have an internal plane oI
symmetry and Iinally, both acids` enantiomers are not superimposable. Hence, both mandelic
acid and malic acid have a chiral center and both are chiral molecules. Yet, mandelic acid would
be a good selection Ior resolution oI anime would be because asymmetric carbon which attached
on benzene ring has a very high electron density, thus the electrons are being pulled towards it.
This eventually weaken the OH bond Irom COOH, thereIore it`s easier Ior the cation Irom the
amine to react with mandelic acid. Since its easier, the reaction much more eIIiciently Iaster to
take place (Hegeman et. al 1970).


2) No, the speciIic rotation oI ¹123° not identical as -237° because speciIic rotation is a
characteristic which relative to the nature oI the particular compound. The enantiomer
present can be identiIied by using the biocatalyst. Biocatalyst such as chiral enzymes which
mostly made by L-amino acids. Formation oI enzyme-substrate complex will recognize the
availability oI chirality oI substrate because enzymes are chiral. Since the substrate were able
to change into optically active products. ThereIore, individual enantiomers oI the substrate
may have altered rates oI reaction (Wade 2010).

3) {]
1
÷ |(¹9.46) ¹ (¹9.56) ¹ (¹9.48)| ÷ ¹ 9.48 0.3
3

{o]
2
÷ |(¹9.54) ¹ (¹9.56) ¹ (¹9.50)|/3 ÷ ¹9.53 0.3
{o]
3
÷ |(¹9.54) ¹ ( ¹9.56) ¹ (¹9.50)|/3 ÷ ¹9.53 0.3













#010r0nc0

Harris, D. 2010. Quantitative Chemical Analysis . Edited by Fiorillo, J. W. H. and Company.,
New York. pp. 13-51.
Hegeman, D. G., Rosenberg, E. Y., Kenyon, L. G. 1970. Mandelic acid racemase Irom
Pseudomonas putida. PuriIication and properties oI the enzyme. J. Am. Chem. Soc. 9 (21): 4029-
4036.

Wade, G. L. 2010. Organic Chemistry: Alkyl Halides, Nucleophilic Substitution and
Elimination. Prentice Hall. New Jersey. pp. 225-250.



















Experiment 2: Resolution oI oI (_)-u-phenylethylamine




















Name: Sathyaraj Manmmadurai
Student # : 211043940
T.A : Mahmoud Sayah

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