Compound A, a hydrocarbon with M + = 96 in its mass spectrum, has the 13 C
Question:
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
Transcribed Image Text:
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
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