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JEE Main 2025 Jan 29 Shift 1, Chemistry Q9: Preparation of Alkyl Halides (Halo Alkanes) & Aryl Halides (Halo Arenes)

JEE Main2025Jan 29, Shift 1Chemistry
Q.

In the following substitution reaction :

Product 'P' formed is :

  1. A
  2. B
  3. C
  4. D
Solution

The substrate undergoes nucleophilic aromatic substitution () via the addition-elimination (Meisenheimer) pathway. Ethoxide attacks a ring carbon bearing , and the intermediate carbanion is stabilised only if the negative charge can be delocalised onto the group at ortho or para to the leaving Br.

Of the two C-Br positions, only the one para to has this stabilisation, so that Br is displaced. The remaining Br (ortho to in the original numbering, now ortho to the new ) stays intact.

Hence product P is 2-bromo-1-ethoxy-4-nitrobenzene, i.e. option (1).

Concept behind this question

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