Q9 · 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: C ✓ checked by 4AB · confidence medium
Explanation
KH/diglyme at 110 °C drives an anionic oxy-Cope ([3,3]) through a chair TS. Tautomerisation gives the cyclohexanone bearing the side chain with the relative stereochemistry and the (E)-enol-ether geometry shown in (c).
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