Chemistry 30A3 Fall 2011 Labs Dr. Troendle 35

Chemistry 30A3 Fall 2011 Labs Dr. Troendle 35 - In this...

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Chemical Biology 3OA3, September 2009 Page 35 H Me OH H Ph OH H O H H Me Ph OH H H Me H OH Ph OH H OH Me Ph OH H O H Me H Ph OH H H Me OH Ph OH Major conformer 1: OH and OH gauche H and H gauche 1 R , 2 S isomer: Major conformer 2: OH and OH gauche H and H gauche Minor conformer: OH and OH anti H and H anti Major conformer 1: OH and OH gauche H and H anti Major conformer 2: OH and OH gauche H and H gauche Minor conformer: OH and OH anti H and H gauche 1 R , 2 R isomer: At the end of this experiment, you should know the stereochemistry of the diol product 2 . Optical rotation: Optical activity is a property of chiral compounds. It can be used to determine which enantiomer of the diol has been obtained.
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Unformatted text preview: In this experiment, time and equipment permitting, you will combine several samples of diol, and the optical rotation will be measured by your TA on a polarimeter. You should convert the observed rotation, , into a specific rotation [ ] (see the 2OA3/2OB3 textbook for the procedure). The literature melting points and optical rotations for the stereoisomers of the diol are shown in the Table below: Isomer mp [ ] D (1 R ,2 S ) 89-91 o C -40 o (1 S ,2 R ) 89-91 o C +40 o (1 R ,2 R ) 51-53 o C -20 o (1 S ,2 S ) 51-53 o C +20 o...
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This note was uploaded on 01/08/2012 for the course CHM 30A3 taught by Professor Ricktroendle during the Fall '11 term at UNF.

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