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JEE Advanced2026Paper 1CHEM-IV
Q.

Match the major products obtained in the reactions given in List-I with the corresponding structures in List-II and choose the correct option.

  1. A

    P 2; Q 1; R 5; S 4

  2. B

    P 1; Q 2; R 4; S 5

  3. C

    P 1; Q 2; R 3; S 4

  4. D

    P 2; Q 1; R 3; S 5

Solution

(P) Aryl aldoxime + aq NaOH (no acetylation). Deprotonation of the oxime OH and subsequent E2-like loss of water with intramolecular displacement of the ortho-Br by the resulting phenoxide gives 5-nitro-2-hydroxybenzonitrile (an aryl cyanide with an ortho-OH). The –Br is replaced by –OH and the CH=NOH is dehydrated to –CN. P 1.

(Q) Same aldoxime, first acetylated (AcO) then treated with NaCO. The mild base only performs E2 elimination of OAc to give the aryl nitrile, but does not have enough hydroxide character to displace the ortho-Br. The product retains the bromide: 2-bromo-5-nitrobenzonitrile. Q 2.

(R) Aryl methyl ketoxime + aq NaOH. With a methyl group on the oxime carbon (no -H suitable for elimination as a nitrile), the ortho-Br is displaced by the deprotonated oxime oxygen via intramolecular SAr, forming a five-membered O–N ring fused to the benzene ring: 3-methyl-5-nitro-1,2-benzisoxazole. R 4.

(S) O-Acetyl ketoxime + aq NaCO. Mild base hydrolyses the O-acetyl group, regenerating the free oxime (E/Z tautomer of the starting material). No further cyclisation or Beckmann rearrangement occurs under these mild conditions. S 5.

Mapping P 1, Q 2, R 4, S 5 corresponds to option (B).

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