Which among the above compound/s does/do not form Silver mirror when treated with Tollen's reagent?
Which among the above compound/s does/do not form Silver mirror when treated with Tollen's reagent?
Show Hint
- (I), (III) and (IV) only
- Only (IV)
- Only (II)
- (III) and (IV) only
The Correct Option is C
Solution and Explanation
(II) is the enol \(\mathrm{CH_2=C(OH)CH_3}\) (propen-2-ol). It tautomerises to acetone \(\mathrm{CH_3COCH_3}\), a ketone, which does not reduce Tollens' reagent. No mirror.
(III) is an enol with the OH on the =CH carbon (cyclohexylidenemethanol). It tautomerises to cyclohexanecarbaldehyde, an aldehyde, so it gives the mirror.
(IV) is a cyclic hemiacetal (2-hydroxytetrahydropyran). It is in equilibrium with its open-chain form 5-hydroxypentanal, which has a free CHO group, so it gives the mirror.
Only (II) fails to give the silver mirror.
Answer: (3) Only (II)
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