Question

Shown below are a series of monosubstituted tetrahydropyrans, in which the
equatorial versus axial preference of C-1 substituents in chloroform is listed. Use structure and a few
words to rationalize the differential preference as observed.

CH2CH3 NHCH3 in CHCl3 ÖCH3 22:78 1:99 92:8 eq./ax. >99:1

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