Chemistry Carboxylic Acids MDCAT 2011
PMDC Verified Question 90 of 94
\( \text{CH}_3\text{COOH} + \text{PCl}_5 \longrightarrow \) the products of the above reaction are:
A
\( \text{CH}_3\text{COCl} + \text{POCl}_2 + \text{HCl} \)
B
\( \text{CH}_3\text{Cl} + \text{POCl}_3 + \text{HCl} \)
C
\( \text{CH}_3\text{COCl} + \text{POCl}_3 + \text{HCl} \)
D
\( \text{CH}_3\text{COCl} + \text{POCl}_3 + \text{H}_2 \)
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option C: \( \text{CH}_3\text{COCl} + \text{POCl}_3 + \text{HCl} \)
Concept:

Phosphorus pentachloride (\( \text{PCl}_5 \)) is a strong chlorinating agent that substitutes the hydroxyl (\(-\text{OH}\)) group of a carboxylic acid with a chlorine atom to form an acid chloride.

Formula:

$$ \text{CH}_3\text{COOH} + \text{PCl}_5 \longrightarrow \text{CH}_3\text{COCl} + \text{POCl}_3 + \text{HCl} $$

Solution:

  • The \(-\text{OH}\) group in acetic acid is replaced by \(-\text{Cl}\), yielding acetyl chloride (\( \text{CH}_3\text{COCl} \)).


  • The byproducts of this substitution are phosphorus oxychloride (\( \text{POCl}_3 \)) and hydrogen chloride (\( \text{HCl} \)).


Why other options are incorrect:

Option A has an incorrect byproduct (\(\text{POCl}_2\)). Option B suggests cleavage of the C-C bond (forming methyl chloride), which does not happen. Option D lists \(\text{H}_2\) gas instead of \(\text{HCl}\).

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