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lab 6

by: Gabriela Montalvo

lab 6 chm

Gabriela Montalvo
Organic Chemistry Lab 1
Lab TA

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lab 6 report
Organic Chemistry Lab 1
Lab TA
Study Guide
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This 0 page Study Guide was uploaded by Gabriela Montalvo on Friday December 4, 2015. The Study Guide belongs to chm at University of Miami taught by Lab TA in Fall 2015. Since its upload, it has received 104 views.


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Date Created: 12/04/15
Gabriela Montalvo C10596017 CHM 205 Atul Parab November 19 2015 Experiment 6 Resolution of Enm Introduction In this experiment the goal is to separate two enantiomers While separating two different compounds can normally be done using a variety of methods separating enantiomers is much more difficult because enantiomers have the same chemical and physical properties The only difference between enantiomers is that they rotate planepolarized light in opposite directions and they react with other chiral molecules at different rates So the best way to separate enantiomers in a racemic mixture is to convert the enantiomers to diastereomers which have different properties making them more easily separable The purity of the separation can be tested using polarimetry Because enantiomers rotate light in equal and opposite directions the optical purity of a sample of one enantiomer can be determined by dividing the measured angle of rotation by the angle of rotation of the pure enantiomer Data and Results In this lab we were trying to separate the two enantiomers for the RSil phenylethylamine using L tartaric acid to get the amine and find the specific rotation of the amine and optical purity of our sample Our prismatic crystals successfully formed from about 3 weeks ago Melting point of amine 1823 C 1845 C Amount of recovered amine 4278 g Percent Recovery 707 1 Concentration of sample 061 gmL Observed optical rotation 14597O Specific rotation 2393O Optical purity 5938 Enantiomer 7969 Enantiomer 2031 All calculations for this table can be found in the written prelab section Discussion Through our experiment we received the percent recovery of the amine from the original sample to be 7071 The theoretical yield found in the lab manual was 50 because there should be equal amounts of amine and amine in our sample racemic mixture The causes of this higher percentage might have been due to the inability to transfer all the amine from the separation process We received an optical rotation of 14597 the lab manual predicted to have an optical rotation from 10 to 11 This increase in the optical rotation could have due to the sample cell for polarimetry to not being clean enough particle of other molecules or air bubbles in the cell or maybe not having a pure sample of amine Because we had a slightly higher optical rotation than expected this gave us a slightly lower specific rotation than we were expecting which also coordinated lower optical purity of our amine All of these measurements were done doing the calculation from the equations in the lab manual As with every experiment there are sources of error that must be considered First of all the method of separation is not ideal Because it is impossible to ensure that all of one compound is in solution and all of the other is in crystal form some of the desired compound is lost and some of the other compound is kept during filtration introducing impurities into the result However this source of error is taken into account when the purity of the sample is found Also it is difficult to completely clean the polarimeter cells If any impurities were left over in the cell this could introduce impurities and cause an incorrect reading in the observed rotation However very little impurity would be left and therefore should have only had a minute effect on the results Conclusion In conclusion based on our measurementscalculation of specific rotation and optical purity we found that our initial same of RSi1phenylethylamine had 7969 enantiomer and 2031 enantiomer Although the sample was not completely pure the procedure still produced relatively good separation of the enantiomers Therefore we can conclude that this method is an effective way to produce a crude separation of two enantiomers Post lab questions 1 a Optical purity of the amine 353 403 X 100 876 b S or enantiomer 876 12 X 124 938 R or enantiomer 12 X 124 62 2 In order to isolate the enantiomer from the Rxphenylethylamine diastereomer we have to convert the diastereomer back to the enantiomer To do this we take our diastereomer and add NaOH to separate the disodium tartrate and the amine Then we warm the solution to activate the amine and then filter the solution through the separatory funnel Once we get our amine we add anhydrous potassium carbonate to take out any of the remaining NaOH After this process then we have isolated the enantiomer 3 The white compound formed is called Ncarboxyl amine derivative an amine salt and the equation for this formation is CNHZ HC H3C 02 gt R NH C 02 H 4 A pure Sxphenylethylamine has a boiling point of 186188 C and its enantiomer will have the same boiling point because enantiomers have the same physical properties Then the optical rotation of a racemic mixture of equal amounts of Samine and R amine Will be 0 because the optical rotations of each amine cancel each other out a Since iRCOOH is in the enantiomer form in order to separate them using RH N 2 you have to change the enantiomers into diastereomers and separate using physical methods and then convert the diastereomers back into enantiomers b Since these compounds are already diastereomers all you have to do to separate then is by physical methods no conversions are needed 6 Specific rotation on l X c 230 05 dm X 035 gmL 131430 7 Optically pure X 40O 075 I solving for X X 40 X 075 30 Observed rotation 30 x l X c x ldm X 25 gmL I solving for x x 30 X ldm X 25 gmL 750 8 CHM 205 December 10 from 91030pm in LC 140 MCAT Review Ouesti 9 D A solution containing 2 M R2butanol and 2 M S2 butanol


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