Compare the nucleophilic strengths of the following two compounds:

According to me it should be the second one, that is, (2R,6R)-2,6-dimethyltetrahydropyran because the methyl groups would exert +I effect which would increase the electron density on the oxygen atom and hence it would become more nucleophilic, but the answer in my book is given as the first one. I don't understand why is it so. Is it because the effects of the methyl groups would cancel as they are connected in trans manner? But then I don't understand why would the first one still have a higher nucleophilicity.

  • 2
    $\begingroup$ The steric hindrance is a much more significant factor here than the inductive effect $\endgroup$
    – Waylander
    May 16, 2021 at 6:53
  • $\begingroup$ It's similar to SIP effect. Search for SIP, there are many reputable sources with information on it. $\endgroup$ May 16, 2021 at 8:11


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