Question

Which one of the following reactions is NOT possible?

• A.
• B.
• C.
• D.

Answer 1

The Correct Option is B

Step 1: Reaction Analysis
1. Reaction (1):
Ether bond (\(\text{C} - \text{OCH}_3\)) cleavage by \(\text{HBr}\) produces phenol (\(\text{C}_6\text{H}_5 - \text{OH}\)) via nucleophilic substitution.
2. Reaction (2):
Phenol (\(\text{C}_6\text{H}_5 - \text{OH}\)) to chlorobenzene (\(\text{C}_6\text{H}_5 - \text{Cl}\)) conversion by \(\text{HCl}\) is \textbf{NOT} possible. The hydroxyl group on the benzene ring is resistant to nucleophilic substitution by \(\text{HCl}\) due to its lone pair.
3. Reaction (3): 
Hydrolysis of chlorobenzene (\(\text{C}_6\text{H}_5 - \text{Cl}\)) with \(\text{NaOH}\) under high temperature and pressure via nucleophilic aromatic substitution yields phenol (\(\text{C}_6\text{H}_5 - \text{OH}\)).
4. Reaction (4):
Electrophilic substitution of anisole (\(\text{C}_6\text{H}_5 - \text{OCH}_3\)) with chlorine in the presence of \(\text{AlCl}_3\) yields ortho and para substituted products.
Step 2: Conclusion
Reaction (2) is impossible because phenol does not undergo nucleophilic substitution with \(\text{HCl}\) to form chlorobenzene.
Final Answer: (2).