Q85 · CSIR-NET Chemistry, December 2015
Paper: CSIR-NET December 2015 · Subject: Organic Chemistry · Chapter: Organic Spectroscopy · Topic: Combined Structure Elucidation · Marks: 2 · Difficulty: Hard
The structure of the compounds that matches the $\mathrm{1H ~ NMR}$ data given below is ${ }^{\mathrm{1}} \mathrm{H ~ NMR ~ DMSO}-\mathrm{d}_{\mathrm{6}}: \delta 7.75 \mathrm{dd}, \mathrm{J}=8 . 8 , 2 . 4 \mathrm{Hz}, \mathrm{1H}, \mathrm{7 . 58}(\mathrm{d}, \mathrm{J}=\mathrm{2 . 4} ~ H z, \mathrm{1H}), \mathrm{6 . 70}(\mathrm{d}, \mathrm{J}=\mathrm{8 . 8}$ Hz, 1H), 6.50 (broad s, 2H), 3.80 (s, 3H).
(a)
(b)
(c)
(d)
Answer
Answer: B ✓ checked by 4AB · confidence high
Explanation
There are three aromatic H (dd 8.8/2.4, d 2.4, d 8.8): a 1,2,4-pattern. NH₂ is broad (2H) and OMe at 3.80. The H ortho to NH₂ is the most shielded (6.70): 2-methoxy-4-nitroaniline (b).
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