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Question #44919

Difficulty: 8/10 | 🟢 Free

The Question

Consider the following reaction sequence starting with ethyl 3-methyl-4-nitrobenzoate:

$\text{Ethyl 3-methyl-4-nitrobenzoate} \xrightarrow[ \text{2. } NaOH(aq) ]{ \text{1. } Sn / HCl, \Delta } \mathbf{P}$

$\mathbf{P} \xrightarrow{ NaNO_2 / HCl, H_2O, 298\text{ K} } \mathbf{Q}$

$\mathbf{Q} \xrightarrow[ \text{2. } H_3O^+ ]{ \text{1. Excess } LiAlH_4, \text{ dry ether} } \mathbf{R}$

Identify the major organic product $\mathbf{R}$ .

Options

A.
4-(hydroxymethyl)-2-methylphenol
B.
(4-amino-3-methylphenyl)methanol
C.
(4-hydrazinyl-3-methylphenyl)methanol
D.
Ethyl 4-hydroxy-3-methylbenzoate

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

Diazotization Temperature Sensitivity|Reduction Selectivity (Sn/HCl vs LiAlH4)

Why This Question Is Tricky

Common Mistakes

This problem tests the chemoselectivity of reducing agents and the thermal stability of diazonium intermediates.

The first trap is recognizing that $Sn/HCl$ selectively reduces the nitro group, leaving the ester intact (unlike $LiAlH_4$ , which would reduce both).

The critical 'Hidden Variable' is the temperature in Step 2 ( $298\text{ K}$ instead of $0-5^\circ\text{C}$ ).

Students mechanically form the diazonium salt but overlook its rapid decomposition into a phenol at room temperature.

Failing to account for this thermal exception leads to incorrect assumptions in the final $LiAlH_4$ reduction step, such as predicting a hydrazine or an amine derivative.

Quick Facts About This Question

Question Information

Subject	Chemistry
Chapter	Amines - Class 12
Concept	Diazotization Temperature Sensitivity
Difficulty	8
Cognitive Load	7
Target Solve Time	160 sec
Access	Free