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Organic Chemistry Ii Lab Report

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Submitted By luistorres1425
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Torres 1

Luis A. Torres
Group #11
USC Chemistry 322b
Formal Lab Report
6th November 2015

Enzymatic Resolution of 1-Phenylethanol and Diastereomer Analysis
Enzymatic transesterification reaction was performed to study the resolution of diastereomers using 1H-NMR analysis. The stereo-selectivity of acylase I, an enzyme, for a 50:50 racemic mixture of 1-phenylethanol was determined. In the first of a two-step reaction, 1-phenylethanol was reacted with vinyl acetate with the help of acylase I to form an ester, unreacted 1-phenylethanol, and vinyl alcohol. The unreacted 1phenylethanol was separated from the ester by column chromatography and confirmed by thin-layer chromatography (TLC). In the second reaction, the unreacted 1-phenylethanol was reacted with (R)-(-)-acetoxyphenylacetic acid to form a diastereomer ester. In the latter reaction, four different 1-phenylethanol samples were used in order to compare 1HNMR data of the resulting diastereomer esters and determine which enantiomer of the
50:50 racemic mixture was preferred by acylase I. Those four samples were: (1) racemic
1-phenylethanol, (2) unreacted 1-phenylethanol, (3) (R)-1-phenylethanol, and (4) (S)-1phenylethanol. After 1H-NMR analysis, it was found that the (S)-1-phenylethanol was preferred by acylase I.


Introduction and Background Information
Scheme 1: Reaction of 1-phenylethanol with vinyl acetate in the presence of the enzyme acylase I to produce 1-phenylethyl acetate (ester), 1-phenylethanol, and vinyl alcohol.
This reaction is called a transesterification reaction because it involves the transfere of an acyl group from an ester to an alcohol to produce a new ester (Moore, J.L., 2015).

Torres 2

Scheme 2: Reaction of unreacted phenylethanol from Reaction 1 and R-(-)acetoxyphenylacetic acid with EDC and 4-DMAP to form an ester,...

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