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GATE 2021 CY – Question 42

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 formed in the following reaction is:

Diagram for GATE 2021 CY question 42
  1. Diagram A
  2. Diagram B
  3. Diagram C
  4. Diagram D

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Correct answer: (D) Diagram D

Explanation

Heating opens the four-membered ring by the thermally allowed conrotatory electrocyclic pathway, generating an ortho-quinodimethane. The starting trans phenyl relationship is converted into the diene geometry that gives cis phenyl groups in the subsequent Diels–Alder adduct. Endo-selective trapping by methyl acrylate fixes the ester relationship. The resulting stereochemistry is the all-dashed arrangement in **D**.