Diastereomers For any molecule that has two or more stereogenic centers, it is possible to have stereoisomers that are not mirror images. Stereoisomers that are not related as enantiomers are called diastercomers. Click "Draw" under the "Load Models" tab and select the "White Rectangle" to crase any models currently in the whiteboard space. © Draw a model that looks like the following molecule. Remember to use the wedge/dash bonds H H HOLIC OH How many stercocenters does this molecule have? 2 O Is there a plane of symmetry within this molecule? DO o Click "Now" and draw a second model that looks like the following molecule. Remember to use the wedge/dash bonds CH KICI H H HO OH At the bottom of the whiteboard, click the "Load Model" button. This will prompt the conversion of your 2D drawing into a 3D ball and stick representation of the molecule, Is this new model a mirror image of the first model? Is each model chiral or achital? What is the relationship between these two model? Click the "Compare" button on the "Other Model Actions" tab on the right of the screen to verify your answer In both figures, substituent priority is assigned the same. Oxygen has the highest atomic number so it is the highest priority substituent. Nitrogen comes second, followed by carbon, and then hydrogen. We then view the molecule by looking at only the three highest priority groups. In figure A, the three highest priority groups are read in a clockwise array, and the lowest priority group (H) is facing away from us (dash bond). This means that the configuration for figure A is R. In figure B, the three highest priority groups are read in a clockwise array, however the lowest priority group (H) is coming towards us (wedge bond). This imeans that although the configuration looks to be R, it is really assigned as S. Now it is your tum to practice • 2-chlorobutane 0 Mark the stercogenic carbon with an asterisk. Assign priority to the groups from highest to lowest. Write the group in the space provided Group Group 2 Group 3 Group 4 Does the priority-order sequence proceed clockwise or counter clockwise? Is this the Ror Senantiomer? • 3-hexanol H OH Mark the stereogenic carbon with an asterisk Assign priority to the groups from highest to lowest. Write the group in space provided, Group Group 2 Group 3 Group 4 Does the priority-order sequence proceed clockwise or counter clockwiso? Is this the Ror Senantiomer?
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