The GATE Grind

GATE 2024 CY – Question 54

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

Consider the following reaction sequence where M and N are the major products. The correct option(s) is (are)

Ruthenium-catalyzed ring-opening metathesis and thermal rearrangement, with four candidate structures.
  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; (C) Option C in the figure

Explanation

Ethylene-assisted ring-opening metathesis converts the strained cyclobutene to a cis-divinylcyclobutane M. Heating induces a divinylcyclobutane–cyclooctadiene rearrangement, producing N in C.