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Question

The major product formed in the following reaction is

Vinyl ether of an octahydronaphthalenol heated at 195 degrees C

This question was previously asked in
MH SET 2026 Paper 1 Question Paper (25-Oct-2026)
The correct answer is
Bicyclic alkene with an angular CH2CHO group

An allyl vinyl ether undergoes the Claisen rearrangement on heating: a concerted [3,3]-sigmatropic shift through a chair-like six-membered transition state that breaks the allylic C–O bond and forms a new C–C bond, giving a γ,δ-unsaturated carbonyl compound.

Here the vinyl ether oxygen is attached to an allylic ring carbon whose neighbouring ring double bond runs to the ring-fusion carbon. Numbering O as atom 3, the vinyl terminus (atom 1) bonds to the far end of the allyl unit, which is the ring-fusion carbon. The ring double bond shifts one position, and the vinyl group becomes a CH2CHO chain. The product is the angular aldehyde, an octahydronaphthalene bearing CH2CHO at the ring junction with the double bond moved into the ring.

A simple isomeric enol ether merely migrates the double bond and is not a rearrangement product at 195 °C. An angular vinyl ether would need the C–O bond to move, which does not happen in a [3,3] shift. A bridged bicyclic ketone would require a different, intramolecular cyclisation not supported by these conditions.

the angular aldehyde with a CH2CHO group at the ring-fusion carbon option is correct.

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