Question

Identify the final product formed when Toluene undergoes a series of reactions with reagents given in the order: 
(i) \( \text{Cl}_2 / \text{Sunlight} \)
(ii) \( \text{H}_2\text{O}/373 \, \text{K} \)
(iii) Acetophenone / \( \text{OH}^- \) at 293 K

• A. 1, 3-Diphenylprop-2-en-1-one
• B. 4-Chloro-2-hydroxyacetophenone
• C. 2, 4-Dichloroacetophenone
• D. p-Hydroxyacetophenone

Hint:

In organic reactions, the sequence of reactions and understanding the nature of each reagent can help predict the final product. Free radical chlorination followed by hydrolysis and nucleophilic substitution leads to the formation of enones in this case.

Answer 1

The Correct Option is A

The given reactions are: 
1. Reaction with \( \text{Cl}_2 \) / Sunlight: Toluene (\( \text{C}_6\text{H}_5\text{CH}_3 \)) undergoes a free radical substitution reaction with chlorine in the presence of sunlight. This results in the formation of chlorotoluene (where a hydrogen atom is replaced by chlorine in the methyl group, forming a benzyl chloride). The methyl group (\( \text{CH}_3 \)) gets chlorinated to form a benzyl chloride intermediate (\( \text{C}_6\text{H}_4\text{CH}_2\text{Cl} \)). 
2. Reaction with \( \text{H}_2\text{O}/373K \): In this step, the benzyl chloride undergoes a hydrolysis reaction, resulting in the formation of the corresponding alcohol. The benzyl chloride is converted to a benzyl alcohol. 
3. Reaction with Acetophenone / \( \text{OH}^- \) at 293 K: In the final step, the product reacts with acetophenone in the presence of a base (\( \text{OH}^- \)) at 293 K. This leads to the formation of a conjugated enone structure, where the product is 1, 3-Diphenylprop-2-en-1-one. 
Thus, the final product is 1, 3-Diphenylprop-2-en-1-one. Hence, the correct answer is \( (A) \).