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Compound D, a hydrocarbon with M + = 96 in its mass spectrum, has the 13 C spectral data given below. On reaction with BH

Compound D, a hydrocarbon with M+ = 96 in its mass spectrum, has the 13C spectral data given below. On reaction with BH3, followed by treatment with basic H2O2, D is converted into E, whose 13C spectral data are also given below. Propose structures for D and E.

Compound D

Broadband-decoupled 13C NMR: 26.8, 28.7, 35.7, 106.9, 149.7 δ

DEPT-90: no peaks

DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 δ

Compound E

Broadband-decoupled 13C NMR: 26.1, 26.9, 29.9, 40.5, 68.2 δ

DEPT-90: 40.5 δ

DEPT-135: positive peak at 40.5 δ; negative peaks at 26.1, 26.9, 29.9, 68.2 δ

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