Question:medium

C₆H₁₂O₃ gives positive iodoform test on hydrolysis with dil. Acid. The hydrolysis product formed gives Tollens’ and iodoform test both. Find structure of C₆H₁₂O₃.

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Iodoform test indicates the presence of a –COCH₃ group, and Tollens' test indicates the presence of an aldehyde group (–CHO).
Updated On: Jan 27, 2026
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The Correct Option is A

Solution and Explanation

The question involves identifying the structure of \(C_6H_{12}O_3\) that satisfies specific chemical tests after hydrolysis.

Step-by-step Explanation:

Understanding the Iodoform Test: The iodoform test is used to identify compounds containing the group \(CH_3C=O\) or \(CH_3CH(OH)-\). A positive test indicates the presence of a methyl ketone or secondary alcohol adjacent to a methyl group.

Analyzing Hydrolysis Products: On hydrolysis with dilute acid, \(C_6H_{12}O_3\) should form a product that gives positive Tollens' and iodoform tests.

Tollens' Test: It tests for the presence of an aldehyde group.

Option Analysis:

  • Option 1: When it hydrolyzes, it can generate a structure containing both aldehyde (for Tollens' test) and methyl ketone or secondary alcohol (for iodoform test).
  • Options 2, 3, 4: These structures, upon hydrolysis, either do not give the needed functional groups for positive tests or form inappropriate combinations.

Hence, the correct structure which fits the requirements is Option 1.

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