Practicing Success
What is the correct order of increasing acidic strength of the given compounds? |
(III) < (IV) < (II) < (I) (IV) < (III)< (II) < (I) (I) < (IV) < (II) < (III) (IV) < (II) < (III) < (I) |
(III) < (IV) < (II) < (I) |
The correct answer is option 1. (III) < (IV) < (II) < (I). To explain the correct order of increasing acidic strength for the given compounds, let's delve into how substituents affect the acidity of carboxylic acids. Key Concepts: Acidic Strength and Conjugate Base Stability: The strength of a carboxylic acid depends on the stability of its conjugate base. The more stable the conjugate base, the stronger the acid. Effect of Substituents: Electron-Withdrawing Groups (EWGs): Increase acidity by stabilizing the negative charge on the conjugate base. Examples include bromine (-Br) in carboxylic acids. Electron-Donating Groups (EDGs): Decrease acidity by destabilizing the negative charge on the conjugate base. Examples include methyl groups (-CH₃). The name sof the given structures are: 1. 2-Bromobutanoic Acid : 2. 3-Bromobutanoic Acid: Bromine is still an EWG, but its effect is less pronounced because it's further from the carboxyl group (at the 3rd position). The electron-withdrawing effect is weaker compared to 2-bromobutanoic acid. Thus, 3-bromobutanoic acid is less acidic than 2-bromobutanoic acid but more acidic than compounds with EDGs. 3. 2-Methylpropanoic Acid: No strong substituent effects here. This is the baseline acidity of a carboxylic acid with no additional groups affecting the carboxyl group. 4. Butanoic Acid: The methyl group is an EDG. It donates electron density towards the carboxyl group, destabilizing the negative charge on the conjugate base (2-methylpropanoate) and thus decreasing the acidity of the acid. Therefore, 2-methylpropanoic acid is the least acidic among the given compounds. Conclusion: Based on the effects of the substituents on the acidity: Least acidic: 2-Methylpropanoic Acid (III) due to the EDG effect. Intermediate acidity: Butanoic Acid (IV) with no significant substituent effects. More acidic: 3-Bromobutanoic Acid (II) due to the weaker EWG effect. Most acidic: 2-Bromobutanoic Acid (I) due to the strong EWG effect of bromine. Thus, the correct order of increasing acidic strength is: (III) < (IV) < (II) < (I) |