Question:medium

L-isomer of a compound ‘A’ \((C_4H_8O_4)\) gives a positive test with \([Ag(NH_3)^2]^+\). Treatment of ‘A’ with acetic anhydride yields triacetate derivative. Compound ‘A’ produces an optically active compound (B) and an optically inactive compound (C) on treatment with bromine water and \(HNO_3\) respectively. Compound (A) is:

Updated On: Mar 25, 2026
  • Option a

  • Option b

  • Option c

  • Option d

Show Solution

The Correct Option is A

Solution and Explanation

To solve the given problem, let's analyze the information and conclude which compound 'A' it corresponds to from the given options:

  1. Compound Formula: The compound 'A' has the formula C_4H_8O_4.
  2. Positive Test with Tollen's Reagent: Compound 'A' gives a positive test with Tollen's reagent [Ag(NH_3)_2]^+, indicating that 'A' is a reducing sugar with a free aldehyde group.
  3. Triacetate Derivative Formation: On treatment with acetic anhydride, the compound forms a triacetate derivative, suggesting that 'A' is a triol, which typically happens with monosaccharides like erythrose.
  4. Reactions with Bromine Water and HNO3:
    • With bromine water, 'A' produces an optically active compound (B), suggesting that bromine doesn't break the optical activity (usually involves alcohol oxidation without disturbing the asymmetric center).
    • Treatment with nitric acid results in an optically inactive compound (C), indicating that 'C' is a meso compound, often associated with oxidation of triols like erythritol.
  5. L-isomer Consideration: Since the compound 'A' is an L-isomer and reduces Tollen’s, this indicates the presence of a free aldehyde group that maintains optical activity.

From the structure and properties discussed above, erythrose (Option A) fits as the correct candidate for 'A'. This sugar structure matches the given formula C_4H_8O_4, reacts positively with Tollen's reagent, forms a triacetate derivative, and undergoes the specified reactions.

Option a

Conclusion: Compound 'A' is the L-isomer of erythrose, which corresponds to the structure given in Option A. This option satisfies all the reaction conditions and the chemical properties described.

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