Lab # 3 - Experiment # 3 Resolution Of ( )-...

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Experiment # 3 – Resolution Of ( ± )- α -Phenylethylamine Name: Partner’s Name: Date:
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Introduction/Objective : The purpose of this lab is to isolate an enantiomer from a racemic mixture. In this case we are trying to isolate (-)- α phenylethylamine from its racemic mixture through a technique called resolution. This converts the enantiomers into diastereoisomers salts. Then taking advantage of the different physical properties of the diastereoisomers, like solubility, the enantiomer (-)- phenylethylamine can be isolated. The following reaction is going to take place in this experiment. Figure 1: Overall Reaction Of This Experiment (York Summer Organic Manual) COOH H CH 3                                        H        C       OH  Ph     C       NH 2                                               Ph      C      NH 2                +              HO     C         H  CH 3 H                                                    COOH (-)-amine                                           (+)-amine                                      (+)-tartaric acid                                                                 more soluble salt [(+)(+)] remains in solution H COO - CH 3                                                   COO   Ph     C       NH 3 +                  H      C       OH           Ph    C           NH 3 +              H         C    OH           CH 3                        HO       C      H                         H                         OH     C     H                                                      COOH                                                                  COOH  less soluble salt   [(-)(+)] slowly crystallizes COO  -   Na  2NaOH                                           H H OH +    2H 2 O Ph C      NH 2            +        OH            C H CH 3 COO  -   Na  +
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Procedure/Observations : The procedures stated in the York Organic Chemistry Summer Manual were followed.
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This note was uploaded on 06/06/2011 for the course CHEM 2020 taught by Professor Potvin during the Spring '09 term at York University.

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Lab # 3 - Experiment # 3 Resolution Of ( )-...

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