Q.The disaccharide sucrose gives negative Tollens test while the disaccharide maltose gives positive Tollens test.
Step 1. A disaccharide gives a positive Tollens' test only if it still has a free hemiacetal/hemiketal group -- i.e. a 'potential aldehyde/ketone' -- somewhere in the molecule (section 14.2.7).
Step 2. In sucrose, the glycosidic linkage runs between C-1 of alpha-glucose AND C-2 of beta-fructose -- BOTH of these are the respective units' own anomeric carbons, so BOTH units' potential carbonyl groups are consumed forming the linkage; no free hemiacetal or hemiketal survives anywhere in the molecule (section 14.2.9a). With no oxidisable group left, sucrose gives a negative Tollens' test.
Step 3. In maltose, the glycosidic linkage runs between C-1 of ONE alpha-glucose unit and C-4 of the SECOND glucose unit. Only the first unit contributes its own anomeric carbon (C-1) to the bond; the second unit's own C-1 hemiacetal group plays no part in the linkage and is left completely free (section 14.2.9b).
Step 4. Because this one free hemiacetal group survives in maltose, it still behaves as a potential aldehyde and gives a positive Tollens' test -- maltose is a reducing sugar, unlike sucrose.
Sucrose is non-reducing (both anomeric -OH's consumed); maltose is reducing (one anomeric -OH stays free).
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