Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Biomolecules

Question:

Monosaccharides are carbohydrates which cannot be hydrolyzed to simple molecules. They may contain 3-7 carbon atoms but monosaccharides containing five and six carbon atoms are more abundant in nature. Those containing an aldehyde group are called aldoses while those containing a keto group are called ketoses. The aldehyde group is always present at C1 while the keto group is usually present at C2.  All monosaccharides reduce Tollens reagent as well as Fehling's solution and hence are called reducing sugars. Pentoses ands hexoses have cyclic structures, furanose (five membered) and pyranose (six membered). Ribose in RNA and fructose in sucrose exist in the furanose form while glucose, mannose, galactose, etc. all exist in the pyranose form. During ring formation C1 in aldohexoses and C2 in fructose becomes chiral and hence all these monosaccharides exist in two stereoisomeric forms called the  α-anomer and the β-anomer while C1 and C2 are called glycosidic or anomeric carbon atoms and the bonds connected to glycosidic carbon are called glycosidic linkages. In contrast, stereoisomers, which differ in configuration at any other chiral carbon are called epimers. When two molecule of the same or different monosaccharide combine together through glycosidic linkage, a disaccharide is formed. All monosaccharides and reducing disaccharides react with excess of phenyl hydrazine to form osazones which are oftenly used for their characterization. 

Mutarotation does not occur in 

Options:

Sucrose 

Glucose 

Gulose 

Galactose 

Correct Answer:

Sucrose 

Explanation:

The correct answer is option 1. Sucrose.

Mutarotation is the change in the optical rotation because of the change in the equilibrium between two anomers when the corresponding stereocenters interconvert. 

Maltose is a reducing sugar because it has a hydroxyl group on the right-hand ring (like the orientation of simple carbohydrates as beta or alpha).

Sucrose is not a reducing sugar because it does not have an available hydroxyl group. The glycosidic bond that forms in sucrose occurs between the anomeric carbons on glucose and fructose which eliminates the availability of the hydroxyl group. The anomeric carbon is the carbon where the ring forms between the hydroxyl carbon and the carbonyl carbon. 

Without this hydroxyl group, the ring cannot open and close and therefore not undergo mutarotation. Reducing sugars can undergo mutarotation. Non-reducing sugars cannot undergo mutarotation.