Chemistry Alcohols & Phenols SZABMU 2024
PMDC Verified Question 10 of 95
Which solvent is used when alcohol reacts with thionyl chloride to form alkyl halide?
A
Zinc chloride
B
Carbon tetrachloride
C
Pyridine
D
Sulphuric acid
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option C: Pyridine
Concept:

The Darzens halogenation utilizes thionyl chloride (\(\text{SOCl}_2\)) to convert alcohols to alkyl chlorides. Managing the acidic byproducts is crucial for the reaction's equilibrium and mechanism.

Formula:

$$ \text{R-OH} + \text{SOCl}_2 \xrightarrow{\text{Pyridine}} \text{R-Cl} + \text{SO}_2\uparrow + \text{HCl}\uparrow $$

Solution:

  • The reaction produces gaseous sulfur dioxide and hydrogen chloride.


  • To neutralize the corrosive HCl gas and prevent unwanted side reactions, a mild organic base is used as the solvent.


  • Pyridine acts as both the solvent and an acid scavenger, forming pyridinium chloride and shifting the equilibrium to the right.


Why other options are incorrect:

Zinc chloride is the catalyst for the Lucas test (using HCl), not Darzens. Sulphuric acid is a strong acid (counterproductive when trying to neutralize HCl). Carbon tetrachloride provides no acid-scavenging benefits.

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