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GATE 2022 CY – Question 37

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 choice

The major product Q in the given reaction is

Diagram for GATE 2022 CY question 37
  1. Diagram A
  2. Diagram B
  3. Diagram C
  4. Diagram D

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Show answer and explanation

Correct answer: (A) Diagram A

Explanation

Lewis-acid ionization of the trifluoroacetate generates an allylic cation stabilized by silicon. Cyclopentadiene captures this three-carbon component in a formal[4+3] cycloaddition, forming the bridged seven-membered ring. Desilylation leaves the exocyclic methylene shown in **A**. B/D correspond to other connectivity or unreleased groups.