Q17 · CSIR NET Chemistry, December 2015
Paper: CSIR NET December 2015 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Marks: 2 · Difficulty: Medium
The major product formed in the following reaction sequence is:


(a)

(b)

(c)

(d)

Answer
Answer: B ✓ checked by 4AB · confidence medium
Explanation
Intramolecular Heck: oxidative addition of the vinyl iodide, 5-exo syn-carbopalladation onto the ring alkene and β-hydride elimination give the cis-fused hydrindene with the nitrile at the ring junction (b).
Study loop for Reagents, Reaction Mechanisms & Named Reactions