# Polarity and stability

Why is cis-1,2-cyclohexadiol less polar than trans-1,2-cyclohexadiol? I know it has something to do with stability and chair conformations, but I'm not sure how it relates to polarity. I know cis-1,2-cyclohexadiol has a more stable chair conformation than trans.

• Does the cis compound have an internal hydrogen bond which decreases the polarity of the molecule? – user1945827 Apr 13 '17 at 7:31
• Could you indicate what the difference in dipole is, and perhaps add pics of the structures? – porphyrin Apr 13 '17 at 12:38

From the later picture, taking into account i) the relative orientation of the two hydroxyl groups towards each other as well in respect to the cyclohexane moiety and ii) the (assumed) conformational preference for this form over the conformer with two axial oriented hydroxyl groups, I would assume the two individual vectorial contributions along $$\ce{C -> O}$$ are better lined up than in the instance of the (cis)-configuration to yield a larger (global) dipolar moment.