Question:
An organic compound X is oxidised by using acidified $K_{2}Cr_{2}O_{7}$. The product obtained reacts with phenylhydrazine but does not give silver mirror test. The possible structure of X is
An organic compound X is oxidised by using acidified $K_{2}Cr_{2}O_{7}$. The product obtained reacts with phenylhydrazine but does not give silver mirror test. The possible structure of X is
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Secondary alcohol $\xrightarrow{[O]}$ Ketone. Ketones do not give Tollen's (silver mirror) test.
Updated On: Apr 10, 2026
- $CH_{3}CH_{2}OH$
- $CH_{3}-C-CH_{3}$
- $(CH_{3})_{2}CHOH$
- $CH_{3}CHO$
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The Correct Option is C
Solution and Explanation
Step 1: Oxidation of X
Compound X is oxidized by $K_{2}Cr_{2}O_{7}$ to form a product that reacts with phenyl hydrazine. This indicates the product is a carbonyl compound (aldehyde or ketone).
Step 2: Negative Tollen's Test
The product fails the silver mirror test, meaning it is a ketone, not an aldehyde.
Step 3: Precursor Identification
Ketones are produced by the oxidation of secondary alcohols. Among the options, $(CH_{3})_{2}CHOH$ (isopropyl alcohol) is the secondary alcohol.
Final Answer: (c)
Compound X is oxidized by $K_{2}Cr_{2}O_{7}$ to form a product that reacts with phenyl hydrazine. This indicates the product is a carbonyl compound (aldehyde or ketone).
Step 2: Negative Tollen's Test
The product fails the silver mirror test, meaning it is a ketone, not an aldehyde.
Step 3: Precursor Identification
Ketones are produced by the oxidation of secondary alcohols. Among the options, $(CH_{3})_{2}CHOH$ (isopropyl alcohol) is the secondary alcohol.
Final Answer: (c)
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