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Question

The major product formed in the following reaction is

The correct answer is

The given reaction involves the nitration of a benzene derivative. In this reaction, concentrated nitric acid (HNO3) is used as the nitrating agent, usually in the presence of a catalyst such as sulfuric acid, under moderate temperature (30°C).

The starting compound is a benzene ring with two carboxylic acid groups (COOH) in the meta positions relative to each other. In electrophilic aromatic substitution reactions, such as nitration, carboxyl groups are deactivating and meta-directing due to their electron-withdrawing nature.

Let's analyze the positions where the nitro group (NO2) might add:

  1. The carboxyl groups direct incoming substituents to the meta positions relative to themselves.
  2. Considering the deactivating nature of COOH, the most feasible position for the incoming NO2 would be at the position adjacent to one of the COOH groups, but still meta to both.

Based on these points, the major product will most likely have a nitro group added to the position which is para to one COOH and ortho/meta to the other COOH, respecting the meta-directing effect of the COOH groups.

The correct structure according to the given options is:

This product aligns with the prediction given the meta-directing influence of the carboxylic acid groups.

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Important Questions from Organic Structure Stability

  1. The compound, which upon mono-nitration using a mixture of HNO$_3$ and H$_2$SO$_4$, does NOT give the meta-isomer as the major product, is

  2. The mass spectrum of benzoic acid will generate the fragment as a base peak (100% relative abundance) of $m/z$ (mass to charge ratio) at ________ (correct to integer number).
  3. Identify the CORRECT product in the following reaction:

  4. Which one among the following structures is the most stable conformer of (Z)-pent-2-ene?
  5. The total number of tautomers for the following molecule (including the structure provided below) is ____________

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