Question

Toluene when reacted with \( \text{Cl}_2 \) gas at 385 K forms a product X which undergoes further reaction with Sodium ethoxide to yield product Y. The structure of Y is ............

• A. A
• B. B
• C. C
• D. D

Hint:

Electrophilic substitution on the benzylic position of toluene with chlorine leads to benzyl chloride. Sodium ethoxide then replaces the chlorine atom with an ethoxy group to form ethylbenzene.

Answer 1

The Correct Option is A

Step 1: React toluene with chlorine gas.
Toluene (\( \text{C}_6\text{H}_5\text{CH}_3 \)) reacts with chlorine gas (\( \text{Cl}_2 \)) at 385 K. In this reaction, chlorine undergoes an electrophilic substitution reaction at the benzylic position, i.e., the methyl group (\( \text{CH}_3 \)) in toluene is substituted by a chlorine atom to form the product X, benzyl chloride (\( \text{C}_6\text{H}_5\text{CH}_2\text{Cl} \)).
\[ \text{C}_6\text{H}_5\text{CH}_3 + \text{Cl}_2 \xrightarrow{385K} \text{C}_6\text{H}_5\text{CH}_2\text{Cl} \]

Step 2: React product X with sodium ethoxide.
The product X, benzyl chloride (\( \text{C}_6\text{H}_5\text{CH}_2\text{Cl} \)), undergoes nucleophilic substitution with sodium ethoxide (\( \text{NaOEt} \)) to replace the chlorine atom with the ethoxy group (\( \text{C}_2\text{H}_5\text{O} \)) to form the product Y, ethylbenzene (\( \text{C}_6\text{H}_5\text{CH}_2\text{O} - \text{C}_2\text{H}_5 \)).
\[ \text{C}_6\text{H}_5\text{CH}_2\text{Cl} + \text{NaOEt} \rightarrow \text{C}_6\text{H}_5\text{CH}_2\text{O} - \text{C}_2\text{H}_5 \]

Step 3: Conclusion.
The structure of Y is an ethoxy-substituted benzene, which corresponds to the product in option (A).