Question:medium

An alcohol X ($\text{C}_5\text{H}_{12}\text{O}$) produces turbidity instantly with conc. $\text{HCl}/\text{ZnCl}_2$. Isomer (Y) of $\text{X}$ undergoes dehydration with conc. $\text{H}_2\text{SO}_4$ at $443 \text{ K}$. $\text{X}$ and $\text{Y}$ respectively are

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The Lucas test ($\text{HCl}/\text{ZnCl}_2$) is used to distinguish between primary, secondary, and tertiary alcohols. The reactivity order is $3^\circ$ (instant turbidity) $> 2^\circ$ (turbidity in 5-10 min) $>1^\circ$ (no turbidity). Dehydration temperature follows the reverse order ($1^\circ$ highest, $3^\circ$ lowest).
Updated On: Jun 14, 2026
  • $\text{Structure 1}, \text{Structure 2}$
  • $\text{Structure 2}, \text{Structure 1}$
  • $\text{Structure 3}, \text{Structure 4}$
  • $\text{Structure 4}, \text{Structure 3}$
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The Correct Option is B

Solution and Explanation

Step 1: Analyze the product $\text{X$ from Reaction (A).}
The reaction is: \[ \text{C}_6\text{H}_5\text{CN} \xrightarrow{\text{A}} \text{X} \] The product $\text{X}$ dissolves in dilute $\text{HCl}$, indicating that $\text{X}$ is a base ��� most likely a primary amine ($\text{R-NH}_2$). A nitrile ($\text{R-CN}$) converts to a primary amine ($\text{R-CH}_2\text{NH}_2$) by complete reduction: \[ \text{C}_6\text{H}_5\text{CN} \xrightarrow{\text{A}} \text{C}_6\text{H}_5\text{CH}_2\text{NH}_2 \quad (\text{X}) \] This full reduction can occur via $\text{LiAlH}_4/\text{H}_2\text{O}$, $\text{H}_2/\text{Ni}$, or $\text{Na}/\text{Hg}, \text{C}_2\text{H}_5\text{OH}$ (Mendius reduction). Hence, $\text{A}$ corresponds to $\text{Na}/\text{Hg}, \text{C}_2\text{H}_5\text{OH}$. Step 2: Analyze Reaction (B).
Reaction: \[ \text{C}_6\text{H}_5\text{CN} \xrightarrow{\text{B}} \text{Y} \] The product $\text{Y}$ reacts with $2,4$-DNP reagent, which detects aldehydes or ketones. Therefore, $\text{Y}$ must be an aldehyde ($\text{R-CHO}$). Partial reduction of a nitrile to an aldehyde is carried out by $\text{DIBAL-H}/\text{H}_2\text{O}$: \[ \text{C}_6\text{H}_5\text{CN} \xrightarrow{\text{DIBAL-H/H}_2\text{O}} \text{C}_6\text{H}_5\text{CHO} \quad (\text{Y}) \] Thus, $\text{B} = \text{DIBAL-H}/\text{H}_2\text{O}$. Step 3: Final Verification.
\[ \text{A} = \text{Na}/\text{Hg}, \text{C}_2\text{H}_5\text{OH} \quad (\text{Complete reduction to amine}) \] \[ \text{B} = \text{DIBAL-H}, \text{H}_2\text{O} \quad (\text{Partial reduction to aldehyde}) \] Therefore, the correct option is (B).
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