15. 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 compound B, whose ¹³℃ spectral data are also given below. Propose structures for A and B. Compound A Broadband-decoupled ¹³C NMR: 26.8; 28.7; 35.7; 106.9; 149.7 8 DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at: 26.8; 28.7; 35.7; 106.9 8 Compound B Broadband-decoupled ¹³C NMR: 26.1; 26.9; 29.9; 40.5; 68.2 8 DEPT-90: 40.5 8 DEPT-135: positive peaks at 40.5 8; negative peaks at: 26.1; 26.9; 29.9; 68.2 8

15. 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 compound B, whose ¹³℃ spectral data are also given below. Propose structures for A and B. Compound A Broadband-decoupled ¹³C NMR: 26.8; 28.7; 35.7; 106.9; 149.7 8 DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at: 26.8; 28.7; 35.7; 106.9 8 Compound B Broadband-decoupled ¹³C NMR: 26.1; 26.9; 29.9; 40.5; 68.2 8 DEPT-90: 40.5 8 DEPT-135: positive peaks at 40.5 8; negative peaks at: 26.1; 26.9; 29.9; 68.2 8

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Section13.SE: Something Extra

Problem 60GP: Compound A, a hydrocarbon with M+=96 in its mass spectrum, has the 13C spectral data given below. On...

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The mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.
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