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What's the mechanism when Benedict's Test acts with monosaccharides and disaccharides?
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Ulex replies
 
I hope you don’t really mean the mechanism i.e. the individual steps by which the reaction takes place. If you do, then I must disappoint you because I do not know and have never seen such a full account. I can, however, try to explain what happens and, to some extent, why.
 
Benedict’s solution is a mixture containing copper(II) ions, a complexing agent (a salt of tartaric acid) and an alkaline substance (sodium carbonate). Normally if you make a solution of copper(II) ions alkaline, a precipitate of copper(II) hydroxide (and in this case carbonate) would result. The complexing agent is there to prevent this happening. When a suitable carbohydrate is boiled with Benedict’s solution, the copper(II) ions are reduced to copper(I) ions which are then precipitated as copper(I) oxide, a red solid.
 
Turning to the carbohydrate and what makes it ‘suitable’. You may already know that the monosaccharide glucose is an equilibrium mixture of two molecular forms, a ring form and a straight chain form. The straight chain form includes the group –CHO, an aldehyde group. This is easily oxidised to an acidic group, which means that glucose is a reducing agent which will reduce Benedict’s solution.
One little surprise, here, is that the straight chain form of fructose is not an aldehyde but a ketone which, you might think, would not be a reducing agent; yet fructose does, in fact reduce Benedict’s solution, presumably because it isomerises to an aldehyde.
 
Disaccharides, in general, do not reduce Benedict’s solution because the relevant carbon atoms are being used to join two monosaccharide units together. On boiling with the alkaline Benedict’s solution, hydrolysis to monosaccharides may occur so that some positive reaction may be seen.

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updated: 26 May 2009

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