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Question #43986

Difficulty: 8/10 | 🟢 Free

The Question

Consider the organic compound $\textbf{P}$ , 2-acetylbenzamide. $\textbf{P}$ is subjected to the following reaction sequence:

Excess $I_2$ , $NaOH_{(aq)}$ , $298\text{ K}$
$Na_2S_2O_3{(aq)}$ , then dilute $HCl_{(aq)}$ , $298\text{ K}$

Identify the major organic product $\textbf{Q}$ .

Options

A.
2-carbamoylbenzoic acid
B.
2-aminobenzoic acid
C.
2-aminoacetophenone
D.
Phthalimide

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

Haloform Reaction Logic|Hoffmann Bromamide Rearrangement

Why This Question Is Tricky

Common Mistakes

The problem tests the student's ability to differentiate between the kinetic requirements of the Haloform reaction and the Hoffmann bromamide/iodoamide rearrangement.

Both reactions utilize halogen in aqueous base.

However, the enolization step in the Haloform reaction has a low activation energy and proceeds rapidly at $298\text{ K}$ .

In contrast, the Hoffmann rearrangement involves a high-activation-energy aryl migration from carbon to an electron-deficient nitrogen, requiring significant thermal input.

Students falling for the trap will assume both functional groups react, leading to 2-aminobenzoic acid, or that the amide is more reactive, leading to 2-aminoacetophenone.

Quick Facts About This Question

Question Information

Subject	Chemistry
Chapter	Aldehydes, Ketones, and Carboxylic Acids - Class 12
Concept	Haloform Reaction Logic
Difficulty	8
Cognitive Load	7
Target Solve Time	160 sec
Access	Free