Q47 · CSIR-NET Chemistry, June 2017

Paper: CSIR-NET June 2017 · Subject: Organic Chemistry · Chapter: Organic Spectroscopy · Topic: Combined Structure Elucidation · Marks: 2 · Difficulty: Medium

The correct structure of the compound based on the following characteristic spectral data is IR: $\mathrm{1736} ~ c m^{-\mathrm{1}}$ ${ }^{\mathrm{1}} \mathrm{H ~ NMR}: \delta 3.59(\mathrm{s}, 3 \mathrm{H}), 3.32(\mathrm{t}, \mathrm{2H}), 2.25(\mathrm{t}, \mathrm{2H}), \mathrm{1 . 85}-\mathrm{1 . 75}(\mathrm{m}, \mathrm{2H}), \mathrm{1 . 73}-\mathrm{1 . 62}(\mathrm{m}, \mathrm{2H})$ ${ }^{13}$ C NMR: $\delta$ 174.0, 51.0, 32.9, 32.9, 32.8, 31.0, 23.0
(a)Option (a) structure, ABC26OR0987
(b)Option (b) structure, ABC26OR0987
(c)Option (c) structure, ABC26OR0987
(d)Option (d) structure, ABC26OR0987
Answer
Answer: B ✓ checked by 4AB · confidence high
Explanation
Ester at 1736 cm⁻¹ with OCH₃ singlet 3.59 (δC 51), CH₂Br triplet 3.32, CH₂CO triplet 2.25 and two middle CH₂: methyl 5-bromopentanoate (b).

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