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GATE 2023 CY – Question 18

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 following reaction is

Diagram for GATE 2023 CY question 18
  1. Structure A
  2. Structure B
  3. Structure C
  4. Structure D

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Show answer and explanation

Correct answer: (B) Structure B

Explanation

Tin radical abstracts iodide to give a carbon radical, which undergoes favoured 5-exo-trig cyclization onto the tethered alkene. Hydrogen atom transfer then quenches the resulting external radical. The five-membered ring, cis ring-junction relationship and externalCH2R group select **B**; A/C instead require6-endo closure.