How can the gauche conformation of ethylene glycol be more stable than the anti conformation?

Aren't the bulk groups furthest apart in the anti conformation? Even if hydrogen bonding occurs from gauche conformation which leads to increased stability and lower energy, wouldn't hydrogen bonding occur nonetheless in the ethylene glycol solution with other molecules floating around.

1 Answer
Apr 29, 2017

I think you have answered this question yourself.........

Explanation:

The gauche conformation offers the possibility of intramolecular hydrogen bonding, and the formation of a 5-membered ring stabilized by intramolecular hydrogen bonding. Have a play with a model set in order to satisfy yourself that such an interaction is a possibility.