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Which of the following glycosidic linkages between two monosaccharides results in a disaccharide that fails to give a reddish-brown precipitate with Fehling's solution?

Options

  1. AC₁ of an aldohexose linked to C₄ of another aldohexose
  2. BC₁ of an aldohexose linked to C₆ of another aldohexose
  3. CC₁ of an aldohexose linked to C₄ of a ketohexose
  4. DC₁ of an aldohexose linked to C₂ of a ketohexose

Correct answer

D. C₁ of an aldohexose linked to C₂ of a ketohexose

Step-by-step solution

A disaccharide fails to give a reddish-brown precipitate with Fehling's solution if it is a non-reducing sugar. This occurs when the anomeric carbons of both monosaccharide units are involved in the glycosidic linkage, leaving no free hemiacetal or hemiketal group. For an aldohexose, the anomeric carbon is C₁ . For a ketohexose, the anomeric carbon is C₂ . If C₁ of an aldohexose is linked to C₂ of a ketohexose, both anomeric carbons are locked in the glycosidic bond. Thus, it will not reduce Fehling's solution. In

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