Question:
Why is \( pK_a \) of ClCH2COOH lower than the \( pK_a \) of CH3COOH?
Why is \( pK_a \) of ClCH2COOH lower than the \( pK_a \) of CH3COOH?
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Lower \( pK_a \) means stronger acid — more electron-withdrawing groups lead to stronger acids.
Updated On: Jul 8, 2025
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Solution and Explanation
Step 1: Chlorine is an electron-withdrawing group (–I effect).
Step 2: In ClCH2COOH, the –Cl group stabilizes the conjugate base by dispersing the negative charge.
Step 3: Greater stability of the conjugate base increases acidity and hence lowers the \( pK_a \) value.
Step 2: In ClCH2COOH, the –Cl group stabilizes the conjugate base by dispersing the negative charge.
Step 3: Greater stability of the conjugate base increases acidity and hence lowers the \( pK_a \) value.
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