3
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While comparing the stability, as the $\ce{CH3}$ group is electron donating, the first structure should be more stable due to this reason. But apparently the second one is more stable. Is there another phenomenon taking place here?

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  • $\begingroup$ Isn't your conclusion contradictory? $\endgroup$ – Alchimista Mar 4 at 16:08
  • $\begingroup$ I do not understand $\endgroup$ – user638473 Mar 4 at 16:12
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    $\begingroup$ As formulated one should expect 2 to be more stable. Point is eventually why is the ethyl fragment not stabilising more than a methyl, as usually found and as resumed here chemistry.stackexchange.com/questions/47008/… $\endgroup$ – Alchimista Mar 4 at 16:15
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    $\begingroup$ This is getting absurd. I quite wonder how detached from reality these textbook exercises would get. For all practical purposes there no difference here. You can argue about "inductive effect" vs "hyperconjugation" however long you wish... $\endgroup$ – Mithoron Mar 4 at 17:43
  • $\begingroup$ On the same line of @Mithoron though the example might be of interest in a proper contest (e.g. computational approach) it seems to stretched simple rules to the limit. $\endgroup$ – Alchimista Mar 5 at 8:36

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