These are three newman projections of propylene glycol. The newman projection on

Question

These are three newman projections of propylene glycol.  The newman projection on the left is the least stable.  The newman projection in the middle is the most stable.  

Can anyone tell me why this is?  I would have thought that the newman projection on the right is the most stable, because its hydroxy groups (which contain contain oxygen, the largest and most electronegative element present in the molecule) are anti to each other.

These are three newman projections of propylene glycol. The newman projection on the left is the least stable. The newman projection in the middle is the most stable. Can anyone tell me why this is? I would have thought that the newman projection on the right is the most stable, because its hydroxy groups (which contain contain oxygen, the largest and most electronegative element present in the molecule) are anti to each other.

Explanation / Answer

Hydroxy groups together lead to hydrogen bonding and increase the stability.

In the leftmost projection, hydroxy and methyl group cause static hindrance, thus least stable

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