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Reducing Sugars
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Angelo_2991
#1 Posted : Sunday, July 05, 2020 9:00:39 PM
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Hello,

I believe that I understand what reducing sugars are; they are either cyclic hemiacetals or the open chain aldeydes that can be oxided. My confusion comes from how ketones can act as reducing sugars, when we know that ketones cannot be further oxidized. The CC mentions how they must tautomerize to an aldehyde first, but i cannot wrap my head around how a ketone can tautomerize to an aldeyhde. Can anyone help explain how this works?
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INSTR_Katerina_102
#2 Posted : Monday, July 06, 2020 3:58:05 PM
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Hi,

Ketones tautomerizing to aldehydes is an overall process that you only really see for sugars as they need to have an alcohol alpha to the ketone for this to work.

I have drawn an example here, but essentially what you make is an enol that has two alcohols - this can tautomerize two ways, back to a ketone or to an aldehyde - in this way, you can shift where the aldhyde and ketone are.

https://ibb.co/Cnppcgb

Please let me know if this is unclear.
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