# Is cyclohexanol or hexanol more acidic?

If we had a hexane ring with an $$\ce{OH}$$ substituent vs. a hexane chain with an $$\ce{OH}$$ substituent, which of the two, if any, would result in a weaker conjugate base?

My confusion: The ring appears to be a bulky shape, but the chain would have one more hydrogen in it...

What do you think and do you have a source reference? There isn't anything in the books I have on structures and their influence on acidity.

• It's not a "forum" but Q&A site (yes there's a difference ;) As far as your question is concerned, you need to specify which hexanol isomer you want to consider. Another thing is does it matter much which will be more acidic? I think that difference should be negligible for most purposes. – Mithoron Sep 20 '18 at 21:33
• It's just for something silly like ranking acidity. Generally, in the text books i'm reading, there is not a way to distinguish from two very similar alkane molecules. I was more curious if there was a way I wasn't exposed to. (Probably no practicality, i'm just being picky?) I guess structure is more important, but I was hoping to find a generic "rule of thumb" similar to the "ARIO" or "CARDIO" pneumonic. Since Charge, Resonance, Induction, and Orbitals are all similar, the only thing I could think that would affect acidity would be its geometry?... In a normal case I would just check pka. – Ron Wilson Sep 21 '18 at 0:42
• Well, simple picking the isomer and editing your question would do more good. BTW pKa values of such weak acids are quite uncertain. – Mithoron Sep 21 '18 at 19:45