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Question #43962

Difficulty: 8/10 | 🟢 Free

The Question

Consider the organic compound $\textbf{X}$ : 2-(4-acetyl-2-nitrophenyl)-1,3-dioxolane. It is subjected to two different reduction protocols to yield the major products $\textbf{Y}$ and $\textbf{Z}$ :

Reaction I: $\textbf{X} \xrightarrow{Zn(Hg), \text{ conc. } HCl, \Delta} \textbf{Y}$

Reaction II: $\textbf{X} \xrightarrow{NH_2NH_2, KOH, \text{ ethylene glycol, } \Delta} \textbf{Z}$

Identify the major products $\textbf{Y}$ and $\textbf{Z}$ .

Options

A.
$\textbf{Y}$ : 5-ethyl-2-methylaniline ; $\textbf{Z}$ : 2-(4-ethyl-2-nitrophenyl)-1,3-dioxolane
B.
$\textbf{Y}$ : 2-(4-ethyl-2-aminophenyl)-1,3-dioxolane ; $\textbf{Z}$ : 5-ethyl-2-methylaniline
C.
$\textbf{Y}$ : 4-ethyl-2-aminobenzaldehyde ; $\textbf{Z}$ : 2-(4-ethyl-2-aminophenyl)-1,3-dioxolane
D.
$\textbf{Y}$ : 5-ethyl-2-methylaniline ; $\textbf{Z}$ : 4-ethyl-2-nitrobenzaldehyde

Check Your Answer

Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Mechanism_Trap

Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.

Concepts Behind This Question

Clemmensen vs. Wolff-Kishner|Reduction Selectivity (Sn/HCl vs LiAlH4)

Why This Question Is Tricky

Common Mistakes

This problem tests the orthogonal chemoselectivity of Clemmensen (acidic) vs.

Wolff-Kishner (basic) reductions.

The hidden trap is recognizing that Clemmensen conditions not only reduce the ketone and nitro groups but also hydrolyze the acetal, subsequently reducing the revealed aldehyde.

Students often forget that dissolving metals in acid reduce nitro groups, or they fail to account for the acid-catalyzed deprotection of the acetal.

Conversely, Wolff-Kishner preserves both the base-stable acetal and the nitro group.

Quick Facts About This Question

Question Information

Subject	Chemistry
Chapter	Aldehydes, Ketones, and Carboxylic Acids - Class 12
Concept	Clemmensen vs. Wolff-Kishner
Difficulty	8
Cognitive Load	7
Target Solve Time	160 sec
Access	Free