What is more acidic: 1-naphthol or 2-naphthol?

[@VictortheOrganicChemistryTutor]

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[@varunarora1256]

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[@VictortheOrganicChemistryTutor]

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[@sambitmukhopadhyay3025]

Hey there, I would like to point out something here - the greater acidic strength of 1-naphthol can be explained by resonance itself. If you draw all the possible canonical structures of the anion (you have missed a few here), you will see that 1-naphthol has 10 canonical structures, while 2-naphthol has only 9 canonical structures, thereby explaining the greater stability of the anion derived from 1-naphthol.

[@VictortheOrganicChemistryTutor]

Thank you for your comment, Sambit! What you’re referring to here as the “canonical” structures is, unfortunately, a flawed approach (although it works in this particular example). Let me explain. It’s not the number but the quality of the resonance that matters. I didn’t miss any meaningful contributors. What you refer to as “canonical” structures where you’re flipping the bonds around in the aromatic ring essentially doubling the number of resonance structures is an extremely outdated take on resonance. It doesn’t really help you explain anything. It’s a meaningless and artificial increase in the number of contributors. Any structure with an intact aromatic ring should be drawn with a “donut” instead of the double bonds to begin with. But we don’t do it as it would be even more confusing to the students. So, it’s prudent to focus on the meaningful differences between the structures, rather than just tally them all up. Some school systems are stuck with the “old ways” and are very resilient to any changes. So, we still see some vestiges of old inefficient chemistry or bad explanations resurface again and again. But you will not find any applications of this so called “canonical” approach anywhere in the modern literature b/c it’s just a bad approach. For instance, based on the “canonical” view of resonance, phenol should be more acidic than benzoic acid, and yet, the evidence is to the contrary.

[@sambitmukhopadhyay3025]

Oh, I didn't know that. I am a high school student, and we are taught this at our level, so I applied this method. Anyways, thanks for the information. 🙂🙂🙂