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- Sep 5, 2008
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- During the hemiketal/ acetal formation, why doesn't the carbonyl group reform like it does in ester synthesis by abstracting the proton.
I'm a little confused because when oxygen when carries a positive charge during an intermediate stage, it gets rid of the proton, so why doesn't the carbon do the same? I do know the distinction that in ester synthesis, water is the leaving group but why can't the hydroxyl group stay bonded to carbom and oxygen becomes protonated to form a hydroxyl group.
I'm a little confused because when oxygen when carries a positive charge during an intermediate stage, it gets rid of the proton, so why doesn't the carbon do the same? I do know the distinction that in ester synthesis, water is the leaving group but why can't the hydroxyl group stay bonded to carbom and oxygen becomes protonated to form a hydroxyl group.