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JEE Advanced 2026Paper 1
Exam
JEE Advanced
Year
2026
Paper
Paper 1
Subject
Chemistry
Chapter
Amines

JEE Advanced 2026 · Paper 1 · Chemistry · Amines

Match the major products obtained in the reactions given in List-I...

Match the major products obtained in the reactions given in List-I with the corresponding structures in List-II and choose the correct option.
List-IList-II
(P) Match the major products obtained in the reactions given in List-I with the corresponding structures in List-II and(1) Match the major products obtained in the reactions given in List-I with the corresponding structures in List-II and
(Q) Match the major products obtained in the reactions given in List-I with the corresponding structures in List-II and(2) Match the major products obtained in the reactions given in List-I with the corresponding structures in List-II and
(R) Match the major products obtained in the reactions given in List-I with the corresponding structures in List-II and(3) Match the major products obtained in the reactions given in List-I with the corresponding structures in List-II and
(S) Match the major products obtained in the reactions given in List-I with the corresponding structures in List-II and(4) Match the major products obtained in the reactions given in List-I with the corresponding structures in List-II and
(5) Match the major products obtained in the reactions given in List-I with the corresponding structures in List-II and

Options

  1. AP →\rightarrow 2; Q ⟶\longrightarrow 1; R →\rightarrow 5; S ⟶\longrightarrow 4
  2. BP →\rightarrow 1; Q ⟶\longrightarrow 2; R →\rightarrow 4; S ⟶\longrightarrow 5
  3. CP →\rightarrow 1; Q ⟶\longrightarrow 2; R →\rightarrow 3; S ⟶\longrightarrow 4
  4. DP →\rightarrow 2; Q ⟶\longrightarrow 1; R →\rightarrow 3; S ⟶\longrightarrow 5

Correct answer

B. P →\rightarrow 1; Q ⟶\longrightarrow 2; R →\rightarrow 4; S ⟶\longrightarrow 5

Step-by-step solution

For the reaction in (P), 2-bromo-5-nitrobenzaldehyde oxime reacts with aqueous NaOH. The strong base deprotonates the oxime group. The resulting oximate anion undergoes intramolecular nucleophilic aromatic substitution (SNArS_NAr), attacking the ortho-carbon and displacing the bromide ion to form a 1,2-benzisoxazole intermediate. Since it is derived from an aldoxime, this intermediate has a hydrogen atom at the C3 position. In the presence of NaOH, it undergoes base-catalyzed Kemp elimination (ring opening) to form 2-hydroxy-5-nitrobenzonitrile, which corresponds to structure (1). Thus, P →\rightarrow 1.

In reaction (Q), the aldoxime is treated with acetic anhydride, which acetylates the oxime group to form an O-acetate. Subsequent treatment with the mild base Na2CO3Na_2CO_3 causes the elimination of acetic acid, converting the aldoxime acetate into a nitrile. The bromide is not displaced under these mild conditions. The product is 2-bromo-5-nitrobenzonitrile, which corresponds to structure (2). Thus, Q →\rightarrow 2.

For the reaction in (R), 2-bromo-5-nitroacetophenone oxime reacts with aqueous NaOH. Similar to (P), the oximate anion is formed and displaces the ortho-bromide via SNArS_NAr to form a 1,2-benzisoxazole ring. However, because it is derived from a ketoxime, there is a methyl group at the C3 position instead of a hydrogen. Therefore, Kemp elimination cannot occur, and the reaction stops at the stable 3-methyl-5-nitro-1,2-benzisoxazole, which corresponds to structure (4). Thus, R →\rightarrow 4.

In reaction (S), the O-acetate of the ketoxime is treated with aqueous Na2CO3Na_2CO_3. Since it is a ketoxime derivative, it cannot undergo elimination to form a nitrile. The mild base simply hydrolyzes the acetate group back to the oxime. The base is not strong enough to promote the subsequent SNArS_NAr ring closure. The product is 2-bromo-5-nitroacetophenone oxime, which corresponds to structure (5). Thus, S →\rightarrow 5.

Combining these results gives the sequence P →\rightarrow 1, Q →\rightarrow 2, R →\rightarrow 4, S →\rightarrow 5.

Answer: P →\rightarrow 1; Q ⟶\longrightarrow 2; R →\rightarrow 4; S ⟶\longrightarrow 5
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