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Katharine Wilkinson

Which ethanol derivatives display the gauche effect?

Ahmed Ali  Follow

As per this source, there is evidence for the gauche effect for most of these groups on basis of intramolecular hydrogen bonding:

enter image description here

I tried looking for a similar evidence for 2-nitroethanol, and found this paper on the same:

enter image description here Figure 4. OCCN gauche structures with an intramolecular H-bond for 2-aminoethanol (7) and 2-nitroethanol (9); Conformations 8 and 10 indicate disrupted H-bonds after rotations by approximately 120º about the O-C axes

So it seems like all the groups shown here can show the gauche effect on the grounds of intramolecular hydrogen bonding,and so your answer should be 8

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