Which is the stronger acid in the case of o-Toluic acid and p-Toluic acid?

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In summary, the conversation is discussing the relative acidity of o-Toluic acid and p-Toluic acid. The person believes that o-Toluic acid is less acidic due to the electron-donating effect of the CH3 group, but it is also suggested that o-Toluic acid has a resonance structure that can stabilize the conjugate base anion and make it more acidic. This is known as the "ortho effect."
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Homework Statement


Which one is a stronger acid- o- Toluic acid or p- Toluic acid?


The Attempt at a Solution



I think o-Toluic acid will be less acidic because CH3 - group is nearer to the O-H bond and it will exert more +I effect compared to that in para- position. But at the same time o - Toluic acid increases the electron density of -COOH group by a greater amount than p - Toluic acid.

What is the correct answer and why?
 
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This is an example of what is known as the "ortho effect," and it occurs because of the existence of a somewhat bizarre resonance structure: the carboxyl group can form a weak hydrogen bond-like interaction with the methyl group ortho to it, stabilizing the conjugate base anion and therefore making the molecule more acidic. This interaction is absent when the methyl is para to the carboxyl. Here's a picture, along with a reasonable QTAIM analysis:
https://chemistry.stackexchange.com...ffect-in-substituted-aromatic-acids-and-bases
 
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1. What is the definition of a strong acid?

A strong acid is a substance that completely dissociates into ions when dissolved in water. This means that all of the acid molecules break apart into their component ions, resulting in a high concentration of hydrogen ions (H+) in the solution.

2. How is the strength of an acid determined?

The strength of an acid is determined by its ability to donate hydrogen ions. The more easily an acid can donate hydrogen ions, the stronger it is. This can be measured by the acid's dissociation constant (Ka) or its pH value. A lower pH or a higher Ka value indicates a stronger acid.

3. Is a strong acid dangerous or corrosive?

While some strong acids can be dangerous or corrosive, it ultimately depends on the specific acid and its concentration. For example, hydrochloric acid (HCl) is a strong acid but is also naturally occurring in our stomachs and is not considered dangerous at low concentrations. However, concentrated sulfuric acid (H2SO4) is highly corrosive and can cause severe burns.

4. What are some common examples of strong acids?

Some common examples of strong acids include hydrochloric acid (HCl), sulfuric acid (H2SO4), nitric acid (HNO3), and hydrobromic acid (HBr). These acids are commonly found in industrial and laboratory settings, and some are also used in household cleaning products.

5. Are there any factors that can affect the strength of an acid?

Yes, there are several factors that can affect the strength of an acid. Temperature, concentration, and the presence of other substances in the solution can all impact the strength of an acid. For example, increasing the concentration of an acid will result in a stronger acid, while diluting it will make it weaker.

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