(Solution) - Propose a structure for compound C which has M 86 in its -(2025 Original AI-Free Solution)

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Academic Level: Undergrad. (yrs 3-4)

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Propose a structure for compound C, which has M+ = 86 in its mass spectrum, an IR absorption at 3400 cm?1, and the following 13C NMR spectral data:
Compound C
Broadband-decoupled 13C NMR: 30.2, 31.9, 61.8, 114.7, 138.4?
DF.PT-90: 138.4?
DEPT-135: positive peak at 138.4 ?; negative peaks at 30.2, 31.9, 61.8, 114.7?