Hydrogen bonding in staggered vs eclipsed conformations?

Question

In my first semester of organic chemistry, we learned that staggered conformations have lower energy/higher stability. However, my thought is that if you have interacting OH groups, the hydrogen bonding would make the eclipsed conformations more stable than the staggered conformation. Is this be the case? Why or why not? For example, a small molecule containing two carbons, each with an alcohol group (or more attached). -- Related question: In a 1,3-diaxial interaction, would multiple OH groups (or anything that exhibits hydrogen bonding) lend to stability?

Answer 1

Staggered will still be a better confirmation eclipsed due to the steric effects. A better question is in the staggered form, how does the gauche interaction compare to the anti? In the case of ethylene glycol the gauche interaction is more stable due to the hydrogen bonding being stronger than the steric repulsion. The eclipsed form would still be too energetically unstable even with the hydrogen bonding.

In the second case of a 1,3-diaxial interaction: a single hydroxy group would still have steric effects. 2 hydroxides in a 1,3 diaxial position would be more favorable only in a nonpolar solvent. In more polar solvents there is competition for hydrogen bonding interactions, which means sterics wins over H bonding.