The major product P of the given reaction is · ABC26OR0554

Subject: Organic Chemistry · Chapter: Pericyclic Reactions · Topic: Pericyclic Reactions – General · Exam: GATE 2000-2022 · Marks: 2 · Difficulty: Easy

The major product P of the given reaction is Question structure 1 of 2, ABC26OR0554 Question structure 2 of 2, ABC26OR0554
(a)Option (a) structure, ABC26OR0554
(b)Option (b) structure, ABC26OR0554
(c)Option (c) structure, ABC26OR0554
(d)Option (d) structure, ABC26OR0554
Answer
Answer (as printed): D
Explanation
KH gives the potassium alkoxide, which undergoes an anionic oxy-Cope [3,3] shift. The vinyl C=C and the ring C=C of the bicyclo[2.2.2]octene form the 1,5-diene. The C(O⁻)–bridgehead σ-bond breaks and a new C–C bond forms between the vinyl terminus and the ring alkene carbon. This opens the bicycle into a fused 6/6 system: a cyclohexene ring plus a ring that carries the enolate, which becomes the ketone on work-up. The rigid bicyclic frame forces a boat-like transition state, so the two ring-fusion H atoms end up on the same face, giving a cis-fused octalone. In (d) the ketone sits β to the non-allylic ring-fusion carbon and both junction H are hashed (cis). Answer (d).

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