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GATE 2025 CY – Question 26

Organic Chemistry · Types of Reactions: Nucleophilic and electrophilic substitution reactions (both aromatic and aliphatic). Addition reactions to carbon-carbon and carbon-heteroatom (N and O) multiple bonds. Elimination reactions. Reactive intermediates – carbocation, carbanion, carbenes, nitrenes, arynes and free radicals. Molecular rearrangements. Barton decarboxylation and Barton-McCombie reaction, Hunsdiecker reaction. · 1 mark · Multiple select

Among the given options, the possible product(s) that can be obtained from the following reaction is/are

2-Methoxynaphthalene reacts with chloroform and aqueous sodium hydroxide at 70 °C.
  1. Option A in the figure
  2. Option B in the figure
  3. Option C in the figure
  4. Option D in the figure

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Show answer and explanation

Correct answer: (A) Option A in the figure

Explanation

Only product A is accepted. The CHCl₃/aqueous NaOH conditions generate dichlorocarbene, but naming additional conceivable carbene pathways does not establish that the products drawn in those options form from this substrate under the stated conditions.

Official GATE 2025 answer key: https://gate2026.iitg.ac.in/doc/download/2025_Key/CY_Keys.pdf