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GATE 2026 CY – Question 37

Organic Chemistry · Experimental Techniques in Organic Chemistry: Optical rotation (polarimetry). Application of various chromatographic techniques such as thin-layer, column, HPLC and GC. Applications of UV-visible, IR, NMR spectroscopy and Mass spectrometry in the structural determination of organic molecules. · 2 marks · Multiple choice

Match protons in compound X (Column M) with chemical shifts (Column N).

Column MColumn N
P: HaI: 7.00 (ddd, J = 8.4, 7.3, 1.4 Hz, 1H)
Q: HbII: 7.17 (dd, J = 8.4, 1.4 Hz, 1H)
R: HcIII: 7.59 (ddd, J = 8.4, 7.3, 1.4 Hz, 1H)
S: HdIV: 8.12 (dd, J = 8.4, 1.4 Hz, 1H)
Ortho-nitrophenol with proton labels Ha–Hd and a chemical-shift matching table.
  1. P → II; Q → III; R → I; S → IV
  2. P → I; Q → IV; R → II; S → III
  3. P → II; Q → IV; R → I; S → III
  4. P → I; Q → III; R → II; S → IV

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Correct answer: (A) P → II; Q → III; R → I; S → IV

Explanation

The proton next to nitro (Hd) is most downfield at 8.12 ppm; Ha beside hydroxyl is 7.17 ppm. Hb is para to nitro and Hc para to hydroxyl, giving 7.59 and 7.00 ppm respectively.