Chapter 13.SE, Problem 60GP

Compound A, 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. A is converted into B, whose, ¹³C spectral data are also given below. Propose structures for A and B.

Compound A

Broadband-decoupled ^l3C 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 B

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