Question

Two reactions I and II are given below:

Correct statement regarding the reactions is

• A. Both reactions I and II are feasible
• B. Both reactions I and II are not feasible
• C. Reaction I feasible, but Reaction II not feasible
• D. Reaction I not feasible, but Reaction II feasible

Hint:

Phenols $\neq$ Alcohols. Phenolic C-O bond doesn't break easily (No $S_N1/S_N2$).

Answer 1

The Correct Option is D

Step 1: Analyze Reaction I:
Reactant: Phenol (or substituted phenol). Reagent: $SOCl_2$. The $C-O$ bond in phenol has partial double bond character due to resonance with the benzene ring. It is very strong and difficult to break. Therefore, phenols do not react with thionyl chloride ($SOCl_2$) or hydrogen halides to form aryl halides under normal conditions (unlike alcohols). Conclusion: Reaction I is not feasible.
Step 2: Analyze Reaction II:
Reactant: Benzyl Alcohol derivative (p-Nitrophenylmethanol). Reagent: $HCl$ (with or without catalyst). The $C-O$ bond here is a purely single bond attached to an $sp^3$ carbon. Benzyl alcohols react readily with halogen acids because the intermediate benzylic carbocation is resonance stabilized (though $NO_2$ destabilizes it, the reaction is still characteristic of alcohols, not phenols). Alternatively, primary alcohols react via $S_N2$. Standard reaction: $R-CH_2-OH + HCl \rightarrow R-CH_2-Cl$. Conclusion: Reaction II is feasible.
Step 3: Final Answer:
I is not feasible, II is feasible. Option (D).