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Question

The cation which is the least likely to be an intermediate in the following reaction is

1,1'-Bi(cyclopropyl)-1,1'-diol with pTSA over the reaction arrow
Product 2-ethyl-2-hydroxycyclobutanone

This question was previously asked in
MH SET 2026 Paper 1 Question Paper (25-Oct-2026)
The correct answer is
Spiro cyclopropane cyclobutyl hydroxy carbocation

Cyclopropanols are protonated readily on the strained ring, and the resulting cations undergo cyclopropylcarbinyl-to-cyclobutyl ring expansion (a semipinacol-type shift) to relieve strain.

Step 1 — Protonation of one cyclopropane ring opens it to an ethyl group, giving the hydroxy-stabilised carbocation on the carbinol carbon; this is the open-chain cation attached to the 1-hydroxycyclopropyl group, and its resonance form is the protonated ketone (O-protonated carbonyl).

Step 2 — The neighbouring 1-hydroxycyclopropyl group expands: a ring C–C bond migrates to the cationic carbon, producing the cyclobutyl cation that carries OH on the cationic carbon and OH plus ethyl on the adjacent quaternary carbon.

Step 3 — Loss of a proton from that hydroxy-substituted cation (an oxocarbenium ion) gives 2-ethyl-2-hydroxycyclobutanone. The spiro cation, in which a cyclobutyl cation still bears an intact cyclopropane, would require ionisation of a cyclopropanol C–O bond to a very unstable cyclopropyl cation before any ring opening; it also cannot lead to the ethyl-substituted product, so it is not on the pathway.

the spiro cyclopropane cyclobutyl hydroxy cation option is correct.

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