Understanding Fructose: The Role of Ketone in Reducing Sugar Reactions

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SUMMARY

Fructose, a reducing sugar, utilizes its ketone group as a reducing center, facilitating the reduction of Cu2+ to Cu+ during chemical reactions. The discussion highlights the oxidation of fructose to glucose and mannose via an enediol intermediate, which is relevant in the context of the Benedict's test. Additionally, the iodoform reaction is mentioned as a method to confirm the presence of certain ketones and alcohols. The conversation emphasizes the need for understanding the oxidation mechanisms of ketones, particularly in educational settings.

PREREQUISITES
  • Understanding of reducing sugars and their chemical properties
  • Knowledge of the Benedict's test for sugar detection
  • Familiarity with the iodoform reaction and its applications
  • Basic concepts of organic chemistry, specifically oxidation and reduction reactions
NEXT STEPS
  • Research the mechanism of the iodoform reaction in detail
  • Study the oxidation pathways of ketones and their derivatives
  • Explore the enediol mechanism in carbohydrate isomerization
  • Learn about carbonyl oxides and their role in organic reactions
USEFUL FOR

Chemistry students, educators, and researchers interested in organic chemistry, particularly those focusing on carbohydrate chemistry and oxidation-reduction reactions.

garytse86
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Fructose is a reducing sugar, and the ketone acts as a reducing centre, which reduces Cu2+ --> Cu+. Therefore fructose itself becomes oxidised.

However, how can a ketone group be oxidised?

I thought: aldehyde becomes oxidised to carboxylic acid
ketone: cannot be oxidised.
 
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Try looking up the iodoform reaction.
 
How does that help. I know the iodoform reaction confirms any 2-one, 2-ol, 2-al, ethanol or ethanal. i.e. CH3C=O, but no hydroxide / iodine for reducing sugar test?
 
Well, from what I remember, the ketone is reduced in this case to a carboxlic acid, although not completely sure. Try finding the mechanism, I just don't have the time right now.
 
Yeah, the fructose isomerizes to glucose and mannose via an enediol, which then oxidizes in the standard Benedict's test fashion.

My students happen to be doing that very experiment today.

If you want to oxidize an actual ketone, there's always carbonyl oxides...
 
ok, thank you very much :D
 

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