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The reaction is as follows, with (i) being my answer, and (ii) being the correct answer in the book.

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My question is why is the product (ii) formed here and elimination not favoured here? I think that the first structure is more stable(has extended conjugation) whereas the latter is relatively unstable. I do understand that the carbocation formed during the formation of (ii) is highly stable (cyclopropyl carbocation and has extended conjugation with phenyl), but is this the reason why (ii) is the major product?

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    $\begingroup$ The first structure has a less strained ring???!! Who told you that? $\endgroup$ – Waylander Jun 23 '20 at 20:44
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    $\begingroup$ Likely the rearrangement to the more stable cation is the driving force. In addition to the stability of the rearranged ion, the rearrangement itself is likely to be kinetically facile as it involves a simple electron-pair move and forms the new bond between atoms that are already relatively close together (1,3 in a four-member ring). $\endgroup$ – Oscar Lanzi Jun 23 '20 at 22:12
  • $\begingroup$ @Waylander I get it now, 1st is more strained because of 2 sp2 carbons in a ring. But isn't it more stable because of extended conjugation. Will edit the question now $\endgroup$ – TheQuestioner Jun 24 '20 at 5:29
  • $\begingroup$ @OscarLanzi But if a lot of heat is provided can it form (i)? Is (i) more stable than (ii) at all? $\endgroup$ – TheQuestioner Jun 24 '20 at 5:35
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    $\begingroup$ I would guess heating would only promote the rearrangement. $\endgroup$ – Oscar Lanzi Jun 24 '20 at 9:38

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