Question

Identify product ‘C’ in following reaction
\[ \mathrm{C_2H_5OH \xrightarrow[\text{Pyridine}]{SOCl_2} A \xrightarrow{C_2H_5ONa} B \xrightarrow[\Delta,\ Pressure]{dil.\ H_2SO_4} C} \]

• A. Ethyl ethanoate
• B. Ethanol
• C. Ethanoic acid
• D. But-2-ene

Hint:

Williamson ether synthesis followed by acidic cleavage can regenerate alcohols.

Answer 1

The Correct Option is B

Step 1: First reaction with $SOCl_2$.
Ethanol reacts with thionyl chloride in presence of pyridine to form ethyl chloride (A).

Step 2: Reaction with sodium ethoxide.
Ethyl chloride reacts with sodium ethoxide to form diethyl ether (B) via Williamson ether synthesis.

Step 3: Acidic hydrolysis under heat and pressure.
Diethyl ether on treatment with dilute sulphuric acid under heat and pressure undergoes cleavage to form ethanol.

Step 4: Conclusion.
Hence, the final product (C) formed is Ethanol.