Questions: Highest Kₐ value Lowest Kₐ value Answer Bank CH₃CH₂COOH ClCH₂COOH Cl₂CHCOOH ClCH₂CH₂COOH

Highest Kₐ value Lowest Kₐ value Answer Bank CH₃CH₂COOH ClCH₂COOH Cl₂CHCOOH ClCH₂CH₂COOH
Transcript text: Highest $K_{\mathrm{a}}$ value $\square$ Lowest $K_{\mathrm{a}}$ value Answer Bank $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}$ $\mathrm{ClCH}_{2} \mathrm{COOH}$ $\mathrm{Cl}_{2} \mathrm{CHCOOH}$ $\mathrm{ClCH}_{2} \mathrm{CH}_{2} \mathrm{COOH}$
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Solution

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Solution Steps

Step 1: Understanding the Problem

The problem asks us to identify which compound has the highest and lowest acid dissociation constant (\(K_{\mathrm{a}}\)) from a given list of carboxylic acids. The \(K_{\mathrm{a}}\) value is a measure of the strength of an acid in solution; a higher \(K_{\mathrm{a}}\) value indicates a stronger acid.

Step 2: Analyzing the Compounds

The compounds given are:

  1. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}\) (Propanoic acid)
  2. \(\mathrm{ClCH}_{2} \mathrm{COOH}\) (Chloroacetic acid)
  3. \(\mathrm{Cl}_{2} \mathrm{CHCOOH}\) (Dichloroacetic acid)
  4. \(\mathrm{ClCH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) (2-Chloropropanoic acid)
Step 3: Evaluating the Effect of Substituents

The presence of electronegative substituents like chlorine increases the acidity of carboxylic acids by stabilizing the negative charge on the conjugate base through inductive effects. More chlorine atoms or closer proximity to the carboxyl group generally increase the acid strength.

  • \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}\) has no electronegative substituents, so it is the weakest acid.
  • \(\mathrm{ClCH}_{2} \mathrm{COOH}\) has one chlorine atom directly attached to the carbon adjacent to the carboxyl group, increasing its acidity.
  • \(\mathrm{Cl}_{2} \mathrm{CHCOOH}\) has two chlorine atoms, making it the strongest acid due to the increased electron-withdrawing effect.
  • \(\mathrm{ClCH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) has a chlorine atom further away from the carboxyl group, making it less acidic than \(\mathrm{ClCH}_{2} \mathrm{COOH}\).

Final Answer

  • The compound with the highest \(K_{\mathrm{a}}\) value is \(\mathrm{Cl}_{2} \mathrm{CHCOOH}\).
  • The compound with the lowest \(K_{\mathrm{a}}\) value is \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}\).

\[ \boxed{\text{Highest } K_{\mathrm{a}}: \mathrm{Cl}_{2} \mathrm{CHCOOH}} \] \[ \boxed{\text{Lowest } K_{\mathrm{a}}: \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}} \]

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