Matching Major Products of Oxime Reactions in List I to List II

To determine the correct matching between List-I and List-II, we analyze the reaction mechanisms for each transformation step-by-step:

1. Reaction (P):

   • Substrate: $(E/Z)$-2-bromo-5-nitrobenzaldehyde oxime.
   • Reagent: Aqueous $\text{NaOH}$.
   • Mechanism:
     1. Aqueous $\text{NaOH}$ deprotonates the hydroxyl group of the aldoxime to form an oximate anion: $\text{Ar}-\text{CH}=\text{N}-\text{OH} + \text{OH}^- \longrightarrow \text{Ar}-\text{CH}=\text{N}-\text{O}^- + \text{H}_2\text{O}$
     2. The oximate oxygen acts as an nucleophile and undergoes an intramolecular nucleophilic aromatic substitution ($S_N\text{Ar}$) by attacking the ortho-position, displacing the bromide ion ($\text{Br}^-$) which is strongly activated by the $para\text{-NO}_2$ group. This forms a 5-nitro-1,2-benzisoxazole intermediate.
     3. Because 1,2-benzisoxazole contains a acidic proton at C-3, the strongly basic medium ($\text{NaOH}$) abstracts this proton, triggering ring-opening elimination to yield the 2-hydroxy-5-nitrobenzonitrile.
   • Matching: $\text{P} \rightarrow 1$

2. Reaction (Q):

   • Substrate: 2-bromo-5-nitrobenzaldehyde oxime.
   • Reagents: 1. $(\text{CH}_3\text{CO})_2\text{O}$, 2. $\text{Na}_2\text{CO}_3$.
   • Mechanism:
     1. Acetic anhydride acetylates the oxime hydroxyl group to form an $O$-acetyl aldoxime intermediate: $\text{Ar}-\text{CH}=\text{N}-\text{OH} + (\text{CH}_3\text{CO})_2\text{O} \longrightarrow \text{Ar}-\text{CH}=\text{N}-\text{O-COCH}_3 + \text{CH}_3\text{COOH}$
     2. Subsequent treatment with a mild base ($\text{Na}_2\text{CO}_3$) facilitates $E2$ elimination of acetic acid to yield the 2-bromo-5-nitrobenzonitrile, leaving the aromatic ring bromine atom intact.
   • Matching: $\text{Q} \rightarrow 2$

3. Reaction (R):

   • Substrate: 1-(2-bromo-5-nitrophenyl)ethan-1-one oxime (a ketoxime).
   • Reagent: Aqueous $\text{NaOH}$.
   • Mechanism:
     1. Deprotonation by $\text{NaOH}$ produces the ketoximate anion.
     2. Intramolecular $S_N\text{Ar}$ displacement of the ortho-bromo substituent forms 3-methyl-5-nitro-1,2-benzisoxazole.
     3. Unlike the aldoxime in reaction (P), the C-3 position of this benzisoxazole ring bears a methyl group ($\text{CH}_3$) instead of a hydrogen atom. Lacking an acidic C-3 hydrogen, base-catalyzed ring opening cannot occur, and the 3-methyl-5-nitro-1,2-benzisoxazole remains as the stable final product.
   • Matching: $\text{R} \rightarrow 4$

4. Reaction (S):

   • Substrate: 1-(2-bromo-5-nitrophenyl)ethan-1-one $O$-acetyl oxime.
   • Reagent: Aqueous $\text{Na}_2\text{CO}_3$.
   • Mechanism:
     1. Aqueous $\text{Na}_2\text{CO}_3$ provides mild basic conditions that selectively hydrolyze the acetate ester bond ($-\text{O-COCH}_3$) without causing nucleophilic displacement on the aromatic ring.
     2. Hydrolysis regenerates the parent ketoxime, 1-(2-bromo-5-nitrophenyl)ethan-1-one oxime.
   • Matching: $\text{S} \rightarrow 5$

Comparing the derived matches: $P \rightarrow 1; \quad Q \rightarrow 2; \quad R \rightarrow 4; \quad S \rightarrow 5$

This set of matches corresponds to Option (B).