Chemistry Carboxylic Acids ETEA 2016
PMDC Verified Question 79 of 94
Select the correct order of the acids strength?
A
\( \text{CH}_3\text{COOH} > \text{CHCl}_2\text{COOH} > \text{CH}_2\text{ClCOOH} \)
B
\( \text{CHCl}_2\text{COOH} > \text{CH}_2\text{ClCOOH} > \text{CH}_3\text{COOH} \)
C
\( \text{CH}_2\text{ClCOOH} > \text{CHCl}_2\text{COOH} > \text{CH}_3\text{COOH} \)
D
\( \text{CHCl}_2\text{COOH} > \text{CH}_2\text{COOH} > \text{CH}_2\text{ClCOOH} \)
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option B: \( \text{CHCl}_2\text{COOH} > \text{CH}_2\text{ClCOOH} > \text{CH}_3\text{COOH} \)
Concept:

Acidic strength is magnified by the presence of electron-withdrawing groups (EWG), which operate via the Inductive (\( -I \)) effect to disperse the negative charge of the conjugate base.

Solution:

  • Acetic acid (\( \text{CH}_3\text{COOH} \)) has zero electron-withdrawing halogens.


  • Chloroacetic acid (\( \text{CH}_2\text{ClCOOH} \)) has 1 chlorine atom pulling electron density.


  • Dichloroacetic acid (\( \text{CHCl}_2\text{COOH} \)) has 2 chlorine atoms, exerting a double \( -I \) pull, making it the strongest.


  • The correct decreasing order is therefore: Dichloroacetic > Chloroacetic > Acetic.


Why other options are incorrect:

Options A and C incorrectly list acetic acid as the strongest. Option D has typos (\( \text{CH}_2\text{COOH} \) is not a complete molecule) and incorrect ordering.

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