Question

\(\mathrm{C_6H_{12}O_3}\) gives positive iodoform test. On hydrolysis with dilute acid, the product formed gives both Tollens' test and iodoform test. Find the correct structure of \(\mathrm{C_6H_{12}O_3}\).

• A. \( \mathrm{CH_3COCH_2CH_2CH(OH)OCH_3} \)
• B. \( \mathrm{CH_3CH_2COCH_2CH(OH)CH_3} \)
• C. \( \mathrm{CH_3CH(OH)CH_2CH_2COOCH_3} \)
• D. \( \mathrm{CH_3CH_2CH(OH)COCH_2CH_3} \)

Hint:

For qualitative organic analysis:
Tollens' test detects aldehydes
Iodoform test detects \(\mathrm{CH_3CO{-}}\) or \(\mathrm{CH_3CH(OH){-}}\)
Acid hydrolysis often reveals masked functional groups

Answer 1

The Correct Option is A

Step 1: A positive iodoform test indicates the presence of either: \[ \mathrm{CH_3CO{-}} \text{or} \mathrm{CH_3CH(OH){-}} \]
Step 2: On hydrolysis with dilute acid, the product gives:
Tollens' test \(\Rightarrow\) aldehyde group (\(\mathrm{-CHO}\))
Iodoform test \(\Rightarrow\) methyl ketone group
Step 3: Therefore, the hydrolysis product must contain both: \[ \mathrm{-CHO} \text{and} \mathrm{CH_3CO{-}} \]
Step 4: Option (A) is a hemiacetal. On acid hydrolysis, it yields: \[ \mathrm{CH_3COCH_2CH_2CHO} \] which contains:
Aldehyde group \(\Rightarrow\) Tollens' test positive
Methyl ketone group \(\Rightarrow\) Iodoform test positive Hence, option (A) is correct.