Q19 · CSIR-NET Chemistry, December 2014
Paper: CSIR-NET December 2014 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Named Reactions · Marks: 2 · Difficulty: Medium
The major product of the following reaction is: 
(a)
(b)
(c)
(d)
Answer
Answer: D ✓ checked by 4AB · confidence high
Explanation
Propionylation, then LDA/TMSCl forms the silyl ketene acetal; Ireland–Claisen [3,3] shifts the ring alkene and forges the new C–C bond at the far carbon, giving the 2,5-disubstituted 2,5-dihydrofuran bearing CH(Me)CO₂Me after hydrolysis and CH₂N₂ (d).
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