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NCERT Exemplar · Q6

Q.In a disaccharide, if the reducing groups (the aldehydic or ketonic/anomeric carbons) of BOTH monosaccharide units are used up in the glycosidic bond, no free reducing group is left and the sugar is non-reducing; if one anomeric carbon stays free, the sugar is reducing. Four disaccharide structures are described in the options. Which one is a non-reducing sugar?

(i) Two six-membered (glucopyranose) rings joined by an oxygen bridge in which one ring still keeps a free hemiacetal OH at its anomeric carbon (a reducing disaccharide of the maltose type).
(ii) A six-membered glucopyranose ring joined to a five-membered fructofuranose ring through an oxygen that links BOTH of their anomeric carbons, leaving no free hemiacetal OH on either unit (the sucrose arrangement).
(iii) Two six-membered rings joined by an oxygen bridge that leaves a free anomeric OH on one ring (reducing).
(iv) Two six-membered rings joined by an oxygen bridge that leaves a free anomeric OH on one ring (reducing).
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A sugar is non-reducing only if it has no free hemiacetal/hemiketal (anomeric) OH that can open to a carbonyl. In three of the options one anomeric carbon is still free; only in sucrose (ii) are both anomeric carbons locked in the glycosidic bond.

Concept

The reducing power of a sugar comes from a free anomeric carbon that can open to a free -CHO (aldose) or reduce Tollens'/Fehling's reagent. In a disaccharide, a glycosidic bond forms between the anomeric OH of one unit and an OH of the other. If the second unit's OH is an ordinary (non-anomeric) hydroxyl, the second anomeric carbon stays free and the sugar remains reducing. If BOTH anomeric carbons are used to make the linkage, no free reducing group is left and the sugar is non-reducing.

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