JEE Main · 2026 · 23 Jan 2026 · Shift 1 · Aldehydes Ketones and Carboxylic Acids

From the given following (A to D) cyclic structures, those which will not react with Tollen's reagent are :

(A)B and D
(B)A and D
(C)A and B
(D)B and C✓ Correct

Answer: (D)

Solution

Tollen's reagent is reduced only by a sugar that can open to a free aldehyde, which requires a free hemiacetal (anomeric) hydroxyl. Structures A and D each keep a free hydroxyl at the anomeric carbon and are reducing, so they give the silver mirror. In structures B and C the anomeric carbon is capped as a methyl acetal (a glycoside), which cannot open to the aldehyde form, so these are non-reducing and give no reaction. The compounds that will not react with Tollen's reagent are B and C.

JEE Main · 2026 · 23 Jan 2026 · Shift 1 · Single correct option

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