Chemistry Carboxylic Acids ETEA 2023
PMDC Verified Question 28 of 94
In conversion of acid halides to ester, pyridine is used to:
A
Stabilize acid halides
B
Consume \( \text{HCl} \) formed in the reaction
C
Dehydrate alcohol
D
Dehydrogenate acid halides
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option B: Consume \( \text{HCl} \) formed in the reaction
Concept:

When synthesizing an ester from an acid chloride and an alcohol, hydrogen chloride (\( \text{HCl} \)) gas is produced as a byproduct. Pyridine acts as a mild base/scavenger.

Formula:

$$ \text{R-COCl} + \text{R}'-\text{OH} + \text{Pyridine} \longrightarrow \text{R-COOR}' + \text{Pyridine}\cdot\text{HCl} $$

Solution:

  • Acid chlorides are incredibly reactive, and their reaction with alcohols yields \( \text{HCl} \).


  • If left unchecked, \( \text{HCl} \) can cause unwanted side reactions or reverse equilibria in complex syntheses.


  • Pyridine (a weak organic base) is added specifically to neutralize and consume the \( \text{HCl} \), forming a harmless pyridinium chloride precipitate.


Why other options are incorrect:

Pyridine does not act as a dehydrating or dehydrogenating agent, nor does it stabilize the already hyper-reactive acid halide.

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