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I couldn’t figure out how to turn the five membered ring into 6 membered ring. Pls help

  • 2
    $\begingroup$ Where is your attempt? $\endgroup$
    – cngzz1
    Commented Jan 2, 2021 at 13:45
  • $\begingroup$ Protonate -OH, after which water leaves, generating a carbocation, which rearranges, and then an elimination occurs. You should have a look at E1 mechanism. $\endgroup$ Commented Jan 2, 2021 at 15:48
  • $\begingroup$ I would like to see a solution to this, it looks less than straightforward. $\endgroup$
    – Waylander
    Commented Jan 2, 2021 at 15:58
  • 2
    $\begingroup$ Looks like an acid treatment of tetrahydrofurfuryl alcohol leads to 2,3-dihydropyran. That's all good. But I'm not sure how the inclusion of a methyl in the reactant molecule as above leads to the resulting molecule above instead of 6-Methyl-3,4-dihydro-2H-pyran. I'd like to see the solution as well indeed. $\endgroup$
    – z1273
    Commented Jan 2, 2021 at 16:40

1 Answer 1


Despite the OP having made no effort to answer this, I was intrigued and wanted to see a solution.

The secondary alcohol is protonated by the strong acid, water leaves to generate a secondary cation. With assistance from the ring oxygen, a methylene shift occurs to generate a more stable cation centred on the oxygen. Solvent removes the methine proton to generate the observed dihydropyran product. This only works because of the presence of the oxygen.

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  • $\begingroup$ Please explain how the 'oxygen-centred' cation is more stable? I have very basic knowlege regarding this and I've learnt that positive charge on less electronegative atom would be much more stable than on a more electronegative one. Here, oxygen should be the least stable place the positive charge could be put on, right? $\endgroup$
    – Desai
    Commented Jan 2, 2021 at 19:57
  • 1
    $\begingroup$ Oxygen has electron pairs that it can donate, enough to make this process viable $\endgroup$
    – Waylander
    Commented Jan 2, 2021 at 20:39

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