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GATE 2023 CY – Question 14

Organic Chemistry · Types of Reactions: Nucleophilic and electrophilic substitution reactions (both aromatic and aliphatic). Addition reactions to carbon-carbon and carbon-heteroatom (N and O) multiple bonds. Elimination reactions. Reactive intermediates – carbocation, carbanion, carbenes, nitrenes, arynes and free radicals. Molecular rearrangements. Barton decarboxylation and Barton-McCombie reaction, Hunsdiecker reaction. · 1 mark · Multiple choice

The major product formed in the given reaction is

Diagram for GATE 2023 CY question 14
  1. Structure A
  2. Structure B
  3. Structure C
  4. Structure D

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Show answer and explanation

Correct answer: (A) Structure A

Explanation

Fluoride removes the trimethylsilyl group and the adjacent triflate to generate benzyne. Itsene reaction with the cyclohexene forms a new aryl–carbon bond, transfers an allylic hydrogen and shifts the cyclic double bond. The newly introduced phenyl group and the original phenyl group occupy adjacent saturated positions as drawn in **A**.