The GATE Grind

GATE 2021 CY – Question 13

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. · 1 mark · Multiple choice

The major product formed in the following reaction is:

Diagram for GATE 2021 CY question 13
  1. Diagram A
  2. Diagram B
  3. Diagram C
  4. Diagram D

Practise this question in The GATE Grind →

Show answer and explanation

Correct answer: (C) Diagram C

Explanation

The electron-rich methoxy/silyloxy diene undergoes a thermal Diels–Alder reaction with electron-poor acrylonitrile. The regioselective cycloaddition places CN in the relationship shown in C. Aqueous acid hydrolyses the silyl enol ether and eliminates methanol, converting the initial cyclohexene into a cyclohexenone. The resulting **CN-substituted enone is C**; the nitrile is retained rather than lost as in B.