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

Compound A

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

DEPT-90: no peaks

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

Compound B

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

DEPT-90: 40.5 δ

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

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100 80 E 60 40 D 20 0 10 20 40 60 80 100 120 140 TMS 180 160 140 120 80 Chemical shift (8) 200 100 60 40 20 0 ppm