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Optical Isomer Question

Hello

I am having difficulty explaining this concept (please refer to the attached image) for the question. Can somebody please assist me with some help?

Thank you :smile:

Original post by Smoke_565

Hello

I am having difficulty explaining this concept (please refer to the attached image) for the question. Can somebody please assist me with some help?

Thank you :smile:

Are you familiar with keto - enol tautomerism?

Reply 2

Smoke_565

Hi charco,

I have a very vague understanding of it, but I'm not understanding how that ruins the chirality as the carbon with the methyl and H attached to it is the the chiral centre so if the ketone switches to an enol how would that affect the chiral centre??

Reply 3

charco

Study Forum Helper

Original post by Smoke_565

To switch to an enol the alpha carbon must become sp2 and lose the hydrogen to the oxygen. This means that reverse process gives a 50:50 chance of each enantiomer.