Hi can I have guidance with this problem. Thank you. Joe Carbonhead successfully

Question

Hi can I have guidance with this problem. Thank you.

Joe Carbonhead successfully synthesized the chiral sulfonic acid derivative at the right with absolute stereospecificity to give the single enantiomer shown (way to go Joe!). He eagerly went to measure the specific rotation of his new compound. Much to his dismay, as the compound sat in the polarimeter he saw the specific rotation of the compound slowly drop to zero, where it remained What happened? Draw a mechanism to explain why Joe slowly lost all his optical activity. (Use the back)

Explanation / Answer

Sulfonic acid acts as a catalyst in the racemization of the chiral center by forming an enol of the ketone. The chiral center which has changed from an sp3 to an sp2 now have a planar geometry. Reformation of ketone leads to addition of a proton from both sides on the tertiary carbon center and thus racemization occurs as the compound sits for longer periods in solution while measuring the optical rotation in a polarimeter.

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