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When comparing o,m,p-toluidine basicities, the ortho effect is believed to explain why o-toluidine is weaker. But when comparing o,m,p-toluic acid basicities, the ortho effect is stated as a reason why o-toluic acid is stronger acid. I was told that the ortho effect is a phenomenon in which an ortho- group causes steric hindrance, forcing the $\ce{-COOH}$, $\ce{-NH2}$ or some other bulky group to move out of the plane, inhibiting resonance. Then, if the ortho effect inhibits resonance, why is o-toluic acid the strongest and o-toluidine the weakest?

Where am I going wrong in my understanding of the ortho effect?

When comparing o,m,p-toluidine basicities, the ortho effect is believed to explain why o-toluidine is weaker. But when comparing o,m,p-toluic acid basicities, the ortho effect is stated as a reason why o-toluic acid is stronger acid. I was told that the ortho effect is a phenomenon in which an ortho- group causes steric hindrance, forcing the $\ce{-COOH}$, $\ce{-NH2}$ or some other bulky group to move out of the plane, inhibiting resonance. Then, if the ortho effect inhibits resonance, why is o-toluic acid the strongest and o-toluidine the weakest?

Where am I going wrong in my understanding of the ortho effect?

When comparing o,m,p-toluidine basicities, the ortho effect is believed to explain why o-toluidine is weaker. But when comparing o,m,p-toluic acid basicities, the ortho effect is stated as a reason why o-toluic acid is stronger acid. I was told that the ortho effect is a phenomenon in which an ortho- group causes steric hindrance, forcing the $\ce{-COOH}$, $\ce{-NH2}$ or some other bulky group to move out of the plane, inhibiting resonance. Then, if the ortho effect inhibits resonance, why is o-toluic acid the strongest and o-toluidine the weakest?

Where am I going wrong in my understanding of the ortho effect?

When comparing o,m,p-toluidine basicities, the ortho effect is believed to explain why o-toluidine is weaker. But when comparing o,m,p-toluic acid basicities, the ortho effect is stated as a reason why o-toluic acid is stronger acid. I was told that the ortho effect is a phenomenon in which an ortho- group causes steric hindrance, forcing the $\ce{-COOH}$, $\ce{-NH2}$ or some other bulky group to move out of the plane, inhibiting resonance. Then, if the ortho effect inhibits resonance, why is o-toluic acid the strongest and o-toluidine the weakest?

Where am I going wrong in my understanding of the ortho effect?

When comparing o,m,p-toluidine, basicities, ortho effect is stated as a reason why o-toluidine is weaker But, When comparing o,m,p-toluic ccid basicities, ortho effect is stated as a reason why o-toluic acid is stronger acid. Further, I was given the definition that ortho effect is an effect in which an ortho- group causes steric hindrance, forcing the $\ce{-COOH}$ or $\ce{-NH2}$ or some other bulky group to move out of the plane, inhibiting resonance. Then, if ortho effect inhibits resonance, why is o-toluic acid the strongest and o-toluidine the weakest?

Where am I going wrong in my understanding of the ortho effect?

When comparing o,m,p-toluidine basicities, the ortho effect is believed to explain why o-toluidine is weaker. But when comparing o,m,p-toluic acid basicities, the ortho effect is stated as a reason why o-toluic acid is stronger acid. I was told that the ortho effect is a phenomenon in which an ortho- group causes steric hindrance, forcing the $\ce{-COOH}$, $\ce{-NH2}$ or some other bulky group to move out of the plane, inhibiting resonance. Then, if the ortho effect inhibits resonance, why is o-toluic acid the strongest and o-toluidine the weakest?

Where am I going wrong in my understanding of the ortho effect?