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GATE 2026 CY – Question 49

Organic Chemistry · Pericyclic Reactions and Photochemistry: Electrocyclic, cycloaddition and sigmatropic reactions. Diels-Alder reaction, Claisen and Cope rearrangements and their applications in organic synthesis. FMO method of analysis. Woodward-Hoffmann rules. Photochemistry of alkenes, arenes and carbonyl compounds. Photo-oxidation and photo-reduction. Di-π-methane rearrangements, Norrish type-I and II reactions. Paternό-Büchi reaction, Photo- Curtius and Wolff rearrangements. Barton and Hofmann-Lӧffler-Freytag reactions. · 2 marks · Multiple select

The reaction(s) that produce(s) the following compound is(are)

Norbornenone target and four proposed cyclopentadiene reactions.
  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: (B) Option B in the figure; (C) Option C in the figure

Explanation

B and C are accepted. B uses a nitroalkene cycloaddition followed by conversion of the nitro group to a carbonyl, while C supplies an appropriate masked carbonyl route. The proposed route D does not give the drawn target connectivity; it must not be grouped with C solely because both contain hydrolyzable groups.

Official GATE 2026 answer key: https://gate2026.iitg.ac.in/doc/download/2026/Keys/CY_Keys.pdf